COMPOUND AND PHOTOELECTRIC DEVICE, IMAGE SENSOR AND ELECTRONIC DEVICE INCLUDING SAME

Hereinafter, embodiment for the embodiment detailed hereinafter in the art searched if the person with skill in the art is to 2000. However chamber include a number can be embodied in the form of applied several different embodiment taught herein is not limited.

Drawing the different layers in order by increasing a thickness and area unambiguously shown. The portion throughout a drawing code is configured to receive a specification similar are identical. Layer, film, region, such as when that plate parts which are "on", "directly on" as well as any other portion when intermediate if another portion comprises a unit. Some parts which are "directly on" when it opposite intermediate free portion and a portion of motor vehicle is started substrate.

Clearly one embodiment described in the drawing to describe the media content that is independent when the dispensed portion, through the entire specification same or similar component as well as a drawing code are identical.

The definition of a specification is installed at one free, "substituted" RM, compound (F, Br, Cl or I) halogen atom hydrogen atoms, hydroxy, nitro, cyano group, amino group, to azido, amino [...], [...], [...], carbonyl, carboxylic [...], molecular weight, ester, carboxylic luck practical technique or salt thereof, sulfonic labor pains or salt thereof, phosphoric acid or a salt thereof, C1 to C20 alkyl, C1 to C20 alkoxy, C2 to C20 between the light-emitting, C2 to C20 alkynyl to, C6 to C30 aryl, C7 to C30 aryl-alkyl, C2 to C20 heteroaryl group, C3 to C20 hetero aryl-alkyl, C3 to C30 cycloalkyl, C3 to C15 between the light-emitting cycle, C6 to C15 1 height neel it will know, selected from C2 to C20 substituted [...] and combinations thereof [hey reel Х meaning that the other.

In addition, the definition of which is installed at one specification, "hetero" implies, N, O, S, P and Si containing 1 to 3 heteroatoms selected from two meaning that the other.

In the specification the alkyl group e.g. methyl, ethyl, pro writing, ISO pro writing, for n - butyl, [...][...], for t - butyl, [...], [...] group or the like is cited.

The "cycloalkyl" in the specification, a cyclopropyl group, cyclo [...], [...] cycloalkyl, cycloalkyl group [...] etc. disclosed.

The specification "aryl (aryl) for" all substituents in the annular element has a p - fuel combustion, these p - orbital is conjugated (conjugation) substituent is formed components, active metal, polycyclic or fused ring polycyclic (i.e., having carbon atoms of adjacent pairs formed between the ring) comprises functional groups.

The definition of a specification is installed at one free, C1 to C30 "to cyano containing" includes alkyl, C2 to C30 C2 to C30 alkynyl is substituted with cyano group or the light-emitting of the at least one hydrogen means 1 can be functional groups. The cyano containing in addition said=CR^{X '} - (CR^x R^y )_p - CR^{Y '} (CN)₂ Where R can be represented by the following functional groups^x , R^y , R^x' And R^y' C1 to C10 alkyl group to each independently a hydrogen or hereinafter same or on an integer and p is 0 to 10. Said cyano containing examples of specific dicyano methyl (dicyanomethyl group), DC oh travel money neel (dicyanovinyl group), cyano in roh mote neel etc. (cyanoethynyl group).

The definition of a specification is installed at one free, "heterocyclic" ring including components includes at least one heteroatom, wherein the heteroatom N, O, S, Si and P can be selected, aliphatic ring, aromatic ring or fused ring having a predetermined wavelength.

The definition of a specification is installed at one free, a process is provided "combination" RM one substituent is other substituted, or fuse-present, C1 to C10 alkyl [leyn in a carboxylic acid substituted connected to each other by single bond or big.

The specification "5 won aromatic ring" is in the number 5 won [...] conjugated structure (e.g. C5 aryl group) or conjugated structure [...] hetero gap click the number to the hydraulic (e.g. C2 to C4 a heteroaryl group) 5 won big. The specification "6 won aromatic ring" is in the number 6 won [...] conjugated structure (e.g. C6 aryl group) or conjugated structure 6 won the hetero gap click number to the hydraulic [...] (e.g. C2 to C5 a heteroaryl group) can be comprising, limited to are not correct. In addition the 5 won 6 won can be an aromatic ring or an aromatic ring aromatic ring, limited to are not correct.

Hereinafter compounds according to implementation are described substrate.

In one embodiment represented by compounds according to formula 1.

[Formula 1]

In said formula 1,

L¹ 2 Is a substituted or unsubstituted heterocyclic or substituted or unsubstituted heterocyclic and condensation is a 2,

Ar¹ To Ar³ Hereinafter independently or a substituted or unsubstituted C6 to same or on each other it will be biting, [leyn C30, a substituted or unsubstituted C6 to C30 oh [leyn, substituted or substituted or unsubstituted C3 to C30 hetero [...] and two or more of fused ring selected from,

R³ Is hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, a cyano group, cyano containing selected and combinations thereof,

G is single bond, - O -, - S -, - Se -, - N=, - (CR^f R^g )_k -, - NR^h -, - SiRⁱ R^j -, - GeR^k R^l -, - (C (R^m )=C (Rⁿ )) - SnR and^o R^p Selected, wherein R^f , R^g , R^h , Rⁱ , R^j , R^k , R^l , R^m , Rⁿ ,R^o And R^p Hereinafter identical to or different from each other is independently hydrogen, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group and a substituted or unsubstituted C1 to C10 alkoxy selected from a, Rⁱ andR^j ,R^k andR^l , R^m And Rⁿ andR^o andR^p Or each independently existing forms a ring and are connected to each other, and k is 1 or 2,

Z¹ Is O or CR^b R^c And, wherein R^b And R^c Hereinafter same or on each other independently a hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group or a cyano containing bottom, R^b And R^c A cyano group or a cyano containing at least one of the residue.

Formula 1 compounds represented a specified wavelength region absorbing light absorbing material, linker (L¹ - CR³ ) About an electron donor moieties (electron donor moiety) (electron acceptor moiety) has a structure including a electromagnetic receptor moieties.

In one example, L¹ A substituted or unsubstituted heterocyclic or 5 won example 5 won a heterocyclic ring 5 won or 6 won can be one or more of the fusion ring.

In one example, L¹ One of group 1 is a connector can be listed.

[Group 1]

In said group 1,

X¹ The - Se -, - Te -, - O -, - S (=O) -, - S (=O)₂ -, - NR^a -, - SiR^b R^c - And - GeR^d R^e Selected -,

X² X and³ Hereinafter same or on each other independently - S -, - Se -, - Te -, - O -, - S (=O) -, - S (=O)₂ -, - NR^a -, - SiR^b R^c - And - GeR^d R^e Selected -,

R^a To R^e Same or C1 to C10 alkyl group is independently hydrogen or a substituted or unsubstituted on to each other and a hereinafter,

R¹ , R² , R⁴ And R⁵ Hereinafter same or on each other is independently hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, a cyano group, cyano containing selected and combinations thereof,

* Includes connection points are disclosed.

In one example, L¹ X located within¹ To X³ Oxygen (O) in the molecule moiety present on the subbands comprises an electronic receptor interaction (intramolecular interaction) carbonyl groups increase the absorption strength specified wavelength can be.

In one example, R³ Is hydrogen, C1 to C30 alkyl group may be substituted or unsubstituted or a substituted or deuterium, for example hydrogen, deuterium can be H or methyl.

Formula 1 of an electron donor moiety maybe at least three ring can be a fused ring fusion, Ar¹ And Ar² And a nitrogen-containing ring is fused disclosed.

In Ar formula 1¹ And Ar² G is nitrogen (N) and connected by and is one conjugated structure number [...] compounds can be improve thermal stability. 5 Won two fused aromatic ring atoms is 3 or 6 won such conjugated structure formed but not the limited to 4.

In one example, Ar¹ And Ar² Are each independently a substituted or unsubstituted phenylene, substituted or nonsubstituted substituted [...], substituted or nonsubstituted substituted do not sprout three neel [leyn or nitrogen (N), sulfur (S), selenium (Se) and combinations thereof including at least one hetero atoms selected from heterocyclic (oh [leyn or hetero-aryl) it will be biting, [leyn implementation being. Wherein hetero reel [leyn it will be biting and [leyn it crawls e.g. pyrrole, pyrazole [...], imidazole reel [leyn, oxa [...], the jade company it will become sleepy, [leyn isocyanate, [...] thiazole, the mote oh it will become sleepy, [leyn isocyanate, neel d [leyn pyridyl, pyridyl [...], neel d [leyn pyrimido, [...] antagonist activity, one [leyn indole, [...], ISO [...], [...], [...], quinacridone-based [...], [...] phthalides, benzo tree oh it will keep, [leyn, evasion it will keep, [leyn pyridyl, pyridyl neel evasion midi [leyn, it will be evasion and it will keep, [leyn pyridyl, [...], benzo [...], the leno phenyl which it will count [leyn and benzo the leno phenyl which it will count [leyn can be selected.

In one example, Ar¹ And Ar² Are each independently a substituted or unsubstituted phenylene, a substituted or unsubstituted or a substituted or unsubstituted [...] do not sprout three neel [leyn fixed date be.

In one example, Ar¹ And Ar² At least one of the nitrogen (N), sulfur (S), selenium (Se) and combinations thereof including at least one hetero atoms selected from heterocyclic (oh [leyn or hetero-aryl) it will be biting, [leyn implementation being.

In one example, Ar¹ And Ar² For either represents a substituted or a substituted or unsubstituted phenylene, a substituted or unsubstituted and substituted or unsubstituted or a substituted or [...] do not sprout three neel [leyn fixed date, Ar¹ And Ar² Another one nitrogen (N), sulfur (S), selenium (Se) and combinations thereof including at least one hetero atoms selected from heterocyclic (oh [leyn or hetero-aryl) it will be biting, [leyn implementation being.

In one example, Ar¹ And Ar² For either represents a substituted or a substituted or unsubstituted phenylene, a substituted or unsubstituted and substituted or unsubstituted or a substituted or [...] do not sprout three neel [leyn fixed date, Ar¹ And Ar² A heterocyclic nitrogen (N) (or heteroaryl oh [leyn) including another one it will be biting, [leyn implementation being.

In one example, Ar¹ And Ar² For either represents a substituted or a substituted or unsubstituted phenylene, a substituted or unsubstituted and substituted or unsubstituted or a substituted or [...] do not sprout three neel [leyn fixed date, Ar¹ And Ar² Sulfur (S) or selenium (Se) to another one (or hetero-oh [leyn) including hetero it will be biting, [leyn implementation being.

In one example, Ar¹ And Ar² Nitrogen is used in (N), sulfur (S), selenium (Se) and combinations thereof including at least one hetero atoms selected from heterocyclic (oh [leyn or hetero-aryl) it will be biting, [leyn implementation being.

In one example, Ar¹ And Ar² It will be biting, [leyn including a heterocyclic nitrogen (N) (or hetero-oh [leyn) is used in implementation being.

In one example, Ar¹ And Ar² Are each independently sulfur (S) or selenium (Se) (or hetero-oh [leyn) including a hetero it will be biting, [leyn implementation being.

In one example, Ar¹ And Ar² G 3 position and/or 5 position on at least one of the sulfur (S), selenium (Se), germanium (Ge) and tellurium (Te) comprising heteroatoms can be selected.

In one example, Ar¹ And Ar² On at least one of the position and/or 9 G 1 located at nitrogen (N), sulfur (S) and selenium (Se) comprising heteroatoms can be selected. The, Ar¹ And Ar² Included in at least one heteroatoms, L¹ X located within¹ To X³ The subbands oxygen (O) and electronic receptor moiety present in a molecular interaction (intramolecular interaction) carbonyl groups increase the absorption strength specified wavelength can be.

In one example, an electron donor moiety to one representation formula A to I can be.

[Formula A] [Formula B]

[Formula C] [Formula D]

[Formula E] [Formula F]

[Formula G] [Formula H]

[Formula I]

In said formula A to I,

G is single bond, - O -, - S -, - Se -, - N=, - (CR^f R^g )_k -, - NR^h -, - SiRⁱ R^j -, - GeR^k R^l - And - (C (R^m )=C (Rⁿ )) - Selected, wherein R^f , R^g , R^h , Rⁱ , R^j , R^k , R^l , R^m And Rⁿ Hereinafter identical to or different from each other is independently hydrogen, halogen, a C1 to C10 alkyl group and a substituted or unsubstituted aryl group selected from a substituted or unsubstituted C6 to C12, R^m And Rⁿ Are each independently existing fusion ring is formed or connected to one another, and k is 1 or 2,

G¹¹ G and¹² Hereinafter same or on each other independently - S -, - Se -, - Te -, - GeR^x R^y - And - CR^z R^w Selected -, wherein R^x , R^y , R^z And R^w Hereinafter same or on each other is independently hydrogen, halogen, a C1 to C10 alkyl group and a substituted or unsubstituted C6 to C10 aryl group selected from a substituted or unsubstituted,

R^6A To R^6D And R^7A To R^7D Hereinafter same or on each other independently a hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, a cyano group, cyano containing selected and combinations thereof,

R^6A To R^6D Are each independently existing adjacent 2 the dog or fusion ring is formed are connected to each other,

R^7A To R^7D Are each independently existing adjacent 2 the dog or fusion ring are connected to each other formed on the substrate.

Represented by said formula 1 compounds an electron donor moiety can be represented by either formula 1 a-A unit is inputted to 1 a-D4 to 2000.

[Formula 1 a-A]

[Formula 1 a-B1]

[Formula 1 a-B2]

[Formula 1 a-C1]

[Formula 1 a-C2]

[Formula 1 a-D1]

[Formula 1 a-D2]

[Formula 1 a-D3]

[Formula 1 a-D4]

In said formula 1 a-A to 1 a-D4, L¹ , Ar³ , R³ , Z¹ , G, G¹¹ , G¹² , R^6A To R^6D And R^7A To R^7D The interspace is efined.

Formula 1 (methane group) of azomethine moiety maybe receptor coupled to and cyclic group, at least one cyclic group is a carbonyl group substituted cyclohexane Ar pen [thil roof tile (C=O)³ Of fused ring having a predetermined wavelength.

In one example, a carbonyl group of formula 1 receptor moiety maybe two cycles (C=O) substituted Ar pen [thil roof tile³ Can be fusion of ring.

In one example, a cyano group or a carbonyl group of formula 1 receptor moiety maybe one (C=O) cyano-containing group substituted Ar pen [thil roof tile and one³ Can be fusion of ring.

In one example, of formula 1 to formula E-a 1 receptor moiety can be represented either to E provided 3.

[Formula E-a 1]

[Formula E-a 2]

[Formula E provided 3]

In said formula E-a 1 to E provided 3,

Z¹ Is O or CR^b R^c And, wherein R^b And R^c Hereinafter same or on each other independently a hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a cyano group or a cyano containing bottom, R^b And R^c A cyano group or a cyano containing at least one of the bottom,

Y¹ To Y⁵ N CR hereinafter independently to each other and on the same or^d Selected, where R^d C1 to C10 alkyl group selected from a hydrogen and a substituted or unsubstituted,

R¹¹ To R¹³ Hereinafter identical to or different from each other independently a hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, halogen, a cyano group (- CN), and combinations thereof containing selected from cyano,

N is 0 or 1 and,

G²¹ G and²² Are each independently - S -, - Se -, - GeR^x R^y Selected - and - Te -, wherein R^x And R^y Hereinafter identical to or different from each other is independently hydrogen, halogen, a C1 to C10 alkyl group and a substituted or unsubstituted C6 to C10 aryl group a substituted or unsubstituted in a selected.

As one example, in said formula E provided 1, Y¹ To Y⁴ At least one of the implementation being N.

Compounds represented by said formula 1 to formula 1 a-E electronic receptor moiety unit is inputted can be represented either to 1 a-G.

[Formula 1 a-E]

[Formula 1 a-F]

[Formula 1 a-G]

In said formula 1 a-E to 1 a-G, L¹ , Ar¹ , Ar² , G, R³ , Z¹ , Y¹ To Y⁵ , G²¹ , G²² , R¹¹ To R¹³ Efined aforementioned.

As one example, in said formula 1 a-E, Y¹ To Y⁴ At least one of the implementation being N.

Said formula 1 compounds an electron donor moiety represented by formula 1 a-H to 1 a-S4 to e.g. an electronic receptor analytes subbands moiety can be represented either.

[Formula 1 a-H]

[Formula 1 a-I]

[Formula 1 a-J]

[Formula 1 a-K1]

[Formula 1 a-L1]

[Formula 1 a-M1]

[Formula 1 a-K2]

[Formula 1 a-L2]

[Formula 1 a-M2]

[Formula 1 a-N1]

[Formula 1 a-O1]

[Formula 1 a-P1]

[Formula 1 a-N2]

[Formula 1 a-O2]

[Formula 1 a-P2]

[Formula 1 a-Q1]

[Formula 1 a-R1]

[Formula 1 a-S1]

[Formula 1 a-Q2]

[Formula 1 a-R2]

[Formula 1 a-S2]

[Formula 1 a-Q3]

[Formula 1 a-R3]

[Formula 1 a-S3]

[Formula 1 a-Q4]

[Formula 1 a-R4]

[Formula 1 a-S4]

In said formula 1 a-H to 1 a-S4, L¹ , R³ , G, G¹¹ , G¹² , R^6A To R^6D , R^7A To R^7D , Z¹ , Y¹ To Y⁵ , R¹¹ To R¹³ , N, G²¹ G and²² The interspace is efined.

In one example, said formula 1 compounds represented by the following formula 1 a-T can be represented.

[Formula 1 a-T]

In said formula 1 a-T,

X¹ The - Se -, - Te -, - O -, - S (=O) -, - S (=O)₂ -, - NR^a -, - SiR^b R^c - And - GeR^d R^e Selected -, wherein R^a , R^b , R^c , R^d And R^e To each other on a same or a substituted or unsubstituted C1 to C10 alkyl hydrogen and hereinafter independently selected from,

Ar³ It will be biting, [leyn C6 to C30 is substituted or unsubstituted, a substituted or unsubstituted C6 to C30 oh [leyn, S, Se, Te, Ge, N and combinations thereof at least one heteroatom selected from a substituted or unsubstituted heterocycle containing two or more of [...] and fused ring selected from,

R¹ To R³ Hereinafter same or on each other is independently hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, a cyano group, cyano containing selected and combinations thereof,

Ar¹ And Ar² Hereinafter independently or a substituted or unsubstituted C6 to same or on each other it will be biting, [leyn C30, a C6 to C30 substituted or unsubstituted C3 to C30 [...] oh [leyn and a selected from a substituted or unsubstituted heterocyclic,

G is single bond, - O -, - S -, - Se -, - N=, - (CR^f R^g )_k -, - NR^h -, - SiRⁱ R^j -, - GeR^k R^l -, - (C (R^m )=C (Rⁿ )) - SnR and^o R^p Selected, wherein R^f , R^g , R^h , Rⁱ , R^j , R^k , R^l , R^m , Rⁿ ,R^o And R^p Hereinafter identical to or different from each other is independently hydrogen, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group and a substituted or unsubstituted C1 to C10 alkoxy selected from a, Rⁱ andR^j ,R^k andR^l , R^m And Rⁿ andR^o andR^p Or each independently existing forms a ring and are connected to each other, k is 1 or 2 are disclosed.

2 Compounds represented by said formula 1 a-T one of compounds can be listed as one group.

[Group 2]

In one example, said formula 1 compounds represented by the following formula 1 a-U can be represented.

[Formula 1 a-U]

In said formula 1 a-U,

X² X and³ Hereinafter same or on each other independently - S -, - Se -, - Te -, - O -, - S (=O) -, - S (=O)₂ -, - NR^a -, - SiR^b R^c - And - GeR^d R^e Selected -, wherein R^a , R^b , R^c , R^d And R^e To each other on a same or a substituted or unsubstituted C1 to C10 alkyl hydrogen and hereinafter independently selected from,

Ar¹ To Ar³ Hereinafter independently or a substituted or unsubstituted C6 to same or on each other it will be biting, [leyn C30, a substituted or unsubstituted C6 to C30 oh [leyn, substituted or substituted or unsubstituted C3 to C30 hetero [...] and two or more of fused ring selected from,

R¹ To R³ Hereinafter same or on each other is independently hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, a cyano group, cyano containing selected and combinations thereof,

G is single bond, - O -, - S -, - Se -, - N=, - (CR^f R^g )_k -, - NR^h -, - SiRⁱ R^j -, - GeR^k R^l -, - (C (R^m )=C (Rⁿ )) - SnR and^o R^p Selected, wherein R^f , R^g , R^h , Rⁱ , R^j , R^k , R^l , R^m , Rⁿ ,R^o And R^p Hereinafter identical to or different from each other is independently hydrogen, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group and a substituted or unsubstituted C1 to C10 alkoxy selected from a, Rⁱ andR^j ,R^k andR^l , R^m And Rⁿ andR^o andR^p Or each independently existing forms a ring and are connected to each other, k is 1 or 2 are disclosed.

Compounds represented by said formula 1 a-U 3 compounds can be listed as one group one.

[3 Group]

In one example, said formula 1 compounds represented by the following formula 1 a-V can be represented.

[Formula 1 a-V]

In said formula 1 a-V,

X¹ The - Se -, - Te -, - O -, - S (=O) -, - S (=O)₂ -, - NR^a -, - SiR^b R^c - And - GeR^d R^e Selected -, wherein R^a , R^b , R^c , R^d And R^e To each other on a same or a substituted or unsubstituted C1 to C10 alkyl hydrogen and hereinafter independently selected from,

D is deuterium and,

Ar¹ To Ar³ Hereinafter independently or a substituted or unsubstituted C6 to same or on each other it will be biting, [leyn C30, a substituted or unsubstituted C6 to C30 oh [leyn, substituted or substituted or unsubstituted C3 to C30 hetero [...] and two or more of fused ring selected from,

R¹ And R² Hereinafter same or on each other is independently hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, a cyano group, cyano containing selected and combinations thereof,

G is single bond, - O -, - S -, - Se -, - N=, - (CR^f R^g )_k -, - NR^h -, - SiRⁱ R^j -, - GeR^k R^l -, - (C (R^m )=C (Rⁿ )) - SnR and^o R^p Selected, wherein R^f , R^g , R^h , Rⁱ , R^j , R^k , R^l , R^m , Rⁿ ,R^o And R^p Hereinafter identical to or different from each other is independently hydrogen, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group and a substituted or unsubstituted C1 to C10 alkoxy selected from a, Rⁱ andR^j ,R^k andR^l , R^m And Rⁿ andR^o andR^p Or each independently existing forms a ring and are connected to each other, k is 1 or 2 are disclosed.

In one example, compounds represented by said formula 1 a-V is a compound substituted with deuterium an electron donor such as A - linker compound (1) can be achieved by reacting compound electronic receptor.

[Reactive A]

In one example, such as linker compounds represented by said formula 1 a-V is a compound of hydrogen is replaced by deuterium B obtainable by disapproval.

[Reactive B]

Compounds represented by said formula 1 a-V to be a group 4 compounds listed in example one.

[4 Group]

In one example, said formula 1 compounds represented by the following formula 1 a-W can be represented.

[Formula 1 a-W]

In said formula 1 a-W,

X¹ The - Se -, - Te -, - O -, - S (=O) -, - S (=O)₂ -, - NR^a -, - SiR^b R^c - And - GeR^d R^e Selected -, wherein R^a , R^b , R^c , R^d And R^e To each other on a same or a substituted or unsubstituted C1 to C10 alkyl hydrogen and hereinafter independently selected from,

Ar³ It will be biting, [leyn C6 to C30 is substituted or unsubstituted, a substituted or unsubstituted C6 to C30 oh [leyn, substituted or substituted or unsubstituted C3 to C30 hetero [...] and two or more of fused ring selected from,

R¹ To R³ Hereinafter same or on each other is independently hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, a cyano group, cyano containing selected and combinations thereof,

G is single bond, - O -, - S -, - Se -, - N=, - (CR^f R^g )_k -, - NR^h -, - SiRⁱ R^j -, - GeR^k R^l -, - (C (R^m )=C (Rⁿ )) - SnR and^o R^p Selected, wherein R^f , R^g , R^h , Rⁱ , R^j , R^k , R^l , R^m , Rⁿ ,R^o And R^p Hereinafter identical to or different from each other is independently hydrogen, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group and a substituted or unsubstituted C1 to C10 alkoxy selected from a, Rⁱ andR^j ,R^k andR^l , R^m And Rⁿ andR^o andR^p Or each independently existing forms a ring and are connected to each other, k is 1 or 2 are disclosed.

G¹¹ G and¹² Hereinafter same or on each other independently - S -, - Se -, - Te -, - GeR^x R^y - And - CR^z R^w Selected -, wherein R^x , R^y , R^z And R^w Hereinafter same or on each other is independently hydrogen, halogen, a C1 to C10 alkyl group and a substituted or unsubstituted C6 to C10 aryl group selected from a substituted or unsubstituted,

R^6A And R^6B And R^7A And R^7B Hereinafter same or on each other independently a hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, a cyano group, cyano containing selected and combinations thereof,

R^6A And R^6B Are each independently existing adjacent 2 the dog or fusion ring is formed are connected to each other,

R^7A And R^7B Are each independently existing adjacent 2 the dog or fusion ring are connected to each other formed on the substrate.

Compounds represented by said formula 1 a-W as one group can be listed in one of compounds 5.

[5 Group]

About 510 nm or more in the above-mentioned compounds are thin film state about 565 nm hereinafter maximum absorption wavelength (λ_Max ) May have a. For example about 520 nm to about 560 nm in maximum absorption wavelength within said (λ_Max ) And may have, for example within the range said 565 nm to about 520 nm in maximum absorption wavelength (λ_Max ) May have a. Said thin film may be a thin film deposited in vacuum conditions.

Anti-face width of about 50 nm to about 120 nm in the above-mentioned compounds are thin film may have. The maximum width of the half (half) [...] absorbing point such as liquid crystal (width), if it is less narrow wavelength light range for selectively absorbing anti-face width by removing selectivity is big. By having said green wavelength region can be height to the wavelenght anti-face width range of selectivity. Said thin film may be a thin film deposited in vacuum conditions.

In the periphery of the above-mentioned compounds have a relatively high melting point (melting point, Tm), thin film by vapor deposition can be effectively formed. A uniform deposition is enabled and the impurity is measured but the likelihood of incorporating glass deposition temperature below the melting point compounds are compounds contained in waste water can be deposited together when the elements can be inhibiting. Preferably compounds having a melting point of higher than the deposition temperature. In this regard the aforementioned deposition temperature may have a higher melting point than the compound, for example the melting point of the compound referred to as a high deposition temperature is assumed to be the melting point of Ts Tm Tm provided Ts≥ °C 10 can be satisfying.

The more detailed, the aforementioned compound is an electron donor moiety including electronic receptor moiety (donor a-acceptor) material wherein analytes with donor - [...], donor - [...] material charge-transfer characteristics generally applied thermal deposition aspect glass but easily pyrolysis 1308. When such a compound weak thermal properties, are fed to the gate when the compounds during deposition as well as micro-lens array (MLA) may cause a decrease in transfer conveyor in subsequent processing such as when exposed to further reduce leakage current from performance deterioration again (about 160 °C degree) and a thin film of wool polo lichen can be causes a change.

The aforementioned compound having a structure while improving thermal donor - [...] material by thermal stability can be height. The above-mentioned compounds when applied to charge-transfer characteristics and thermal characteristics can be element unit line.

P type semiconductor or n-type semiconductor when applied to the above-mentioned compounds are for example can be used. In one example, the above-mentioned compounds are p-type semiconductor can be used. The above-mentioned compounds are a fullerene or fullerene derivatives can be used with for example, fullerenes of LUMO energy level of about 4. 2EV since the aforementioned compound provides a 4. 2EV may have higher LUMO energy level. Of a compound HOMO energy levels are above about 5. 0 To 5. 8EV may be, LUMO energy levels are about 2 of a compound described above. 7 To 3. 9EV may be, energy band gap of a compound above about 1. 9 To 2. 3EV implementation being. Said energy level range of HOMO, LUMO level and energy band gap effectively absorbing green wavelengths by having photoresist can be applied p or n-type semiconductor and therefore a high external quantum efficiency (external quantum efficiency, EQE) can improve the efficiency of charges obtained may have.

In one example, about 300 to about 1500 g/mol may have a molecular weight of above-mentioned compounds, having a molecular weight ranging said by thermal chemical vapor deposition process can be more stable. In addition to the above-mentioned compounds are deposition method step may be deposited solution however.

The aforementioned compounds are thin film are formed of different and electronic device can be applied to.

In one example, the above-mentioned compounds are photoelectric device can be applied.

Hereinafter with reference to a photoelectric device according to implementation for drawing through a browser substrate.

Figure 1 shows a cross-section shown also in one implementation according to photoelectric element are disclosed.

With reference to the 1 also, in one implementation according to photoelectric device (100) facing each other number 1 electrode (10) and number 2 electrode (20), the number 1 electrode (10) and number 2 electrode (20) positioned between the organic substrate. The organic layer active layer (30) comprises.

Number 1 electrode (10) and number 2 electrode (20) and the other one of either the cathode (cathode) one anode (anode) are disclosed. Number 1 electrode (10) and number 2 electrode (20) may be at least one of the transparent electrode, said light transmitting electrode (indium tin oxide, ITO) or indium zinc oxide of indium tin oxide for example (indium zinc oxide, IZO) transparent conductors such as, or thin metal thin film can be a single layer or multiple layers made of. Number 1 electrode (10) and number 2 electrode (20) when the one of the fire [thwu storehouse electrode such as for example aluminum (Al) opaque conductor can be made.

Active layer (30) is p type semiconductor compound layer forming the n-type semiconductor compounds pn junction (pn junction), OLEDs (exciton) receives external light and the electrons exciton generated followed for separating layer are disclosed.

Active layer (30) comprising compounds described above can be, for example p type semiconductor or n-type semiconductor can be used. In one example, the above-mentioned compounds are p-type semiconductor can be used.

The aforementioned compounds are green wavelength range of light selectively absorbing compound, compounds including the above-mentioned active layer (30) is about 500 nm to about 600 nm, particularly at about 520 nm to about 565 nm within a wavelength range of maximum absorption wavelength (λ_Max ) Having green wavelengths of light can be selectively absorbing.

Said active layer (30) is about 50 nm to about 120 nm, about 50 nm to about 100 nm (FWHM) specifically with relatively small at the lenslet absorbing curve can exhibit. The active layer (30) may have high selectivity green wavelength range of light.

In one example, active layer (30) is n-type semiconductor can be a fullerene or fullerene derivative, a compound containing a fullerene or fullerene derivative mentioned about 0. 9:1 To about 1. 1:1, E.g. 1:1 volume ratio of about 5. 5 X 10⁴ Cm^-1 Or more, for example about 5. 8 X 10⁴ Cm^-1 To about 2 X 10⁵ Cm^-1 Or about 7. 0 X 10⁴ Cm^-1 To about 2 X 10⁵ Cm^-1 Of absorption coefficient may have.

Examples of said fullerenes C60, C70, C76, C78, C80, C82, C84, C90, C96, C240, C540, mixtures thereof, etc. fullerene nanotubes. Said compound having said fullerene derivatives fullerene substituents means other. Said fullerene derivatives alkyl group, aryl group, hetero [...] substituents such as can be. Said group hetero ring include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, triphenylene ring, naphtacenediones ring, biphenyl ring, pyrrole ring, (furan) furan ring, thiophene ring, imidazole ring, oxazole ring, thiazole ring, pyridine ring, pyrazole group, pyrimidine ring, pyridazine ring, indole triazines (indolizine) ring, indole ring, benzofuran ring, benzothiophene ring, it cuts trillion [phyu column isocyanate (isobenzofuran) ring, benzimidazole ring, imidazopyridine (imidazopyridine) ring, quinolizine (quinolizidine) ring, quinoline ring, segmented ring (phthalazine) phthalides, my petit position (naphthyridine) ring, quinoxaline (quinoxaline) ring, the [khwi the stipendiary company it became sleepy (quinoxazoline) ring, isoquinoline (isoquinoline) ring, carbazole ring (carbazole), etofenamate tree [tin (phenanthridine) ring, acridine (acridine) ring, phenanthroline (phenanthroline) ring, thiazole ring [...] (thianthrene), chromen (chromene) ring, cup [theyn (xanthene) ring, lung stipendiary company cystine (phenoxathin) ring, phenothiazine (phenothiazine) ring or lung najin (phenazine) lock device of disclosed.

In one example, active layer (30) is n type semiconductor as subphthalocyanine or sub phthalocyanine derivative, comprising thiophene or thiophene derivatives or a combination thereof can be.

Said subphthalocyanine or sub phthalocyanine derivative represented formula X can be represented.

[Formula X]

In said formula X,

R³¹ To R³³ Are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, halogen, selected from halogen-containing and combinations thereof,

A, b and c is integer number of 1 to 3,

Z is substituted 1 is multiplexed.

In one example, Z is halogen or halogen-containing group, e.g. F, Cl, Cl or F containing containing actuator disclosed.

Said halogen is F, Cl, I or Br which means the at least one of a halogen-containing alkyl hydrogen can be F, Cl, I or Br meaning can be substituted.

For example formula Z or formula Y but said thiophene derivatives represented, limited to are not correct.

[Formula Y]

[Formula Z]

In said formula Y and Z,

T¹ , T² And T³ Is unsubstituted thiophene substituted or unsubstituted aromatic ring and having,

T¹ , T² And T³ Are each independently existing or fused in which,

X³ To X⁸ Are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 hetero [...], and cyano group or combinations thereof,

EWG¹ EWG and² (Electron withdrawing group) to electronic aspirator is used in implementation being.

As one example, in said formula Y, X³ To X⁸ At least one of the electronic aspirator, e.g. containing a cyano group or a cyano group be.

Active layer (30) is selectively absorbing green light of p type semiconductor compound number 2 can be. Said p type semiconductor compound can be a compound represented by the following formula W as one, limited to are not correct.

[Formula W]

In said formula W,

R⁴¹ To R⁴³ Are each independently a hydrogen, a C1 to C30 substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C1 to C30 aliphatic hetero [...], substituted or a substituted or unsubstituted C2 to C30 aromatic hetero [...], a C1 to C30 substituted or unsubstituted alkoxy group, a substituted or unsubstituted C6 to C30 [...], molecular weight, a C6 to C30 alkyl substituted or unsubstituted mote unyielding spirit, a substituted or unsubstituted C6 to C30 [...], cyano group, containing a cyano, a halogen, a halogen-containing compound, substituted or nonsubstituted substituted sulfonyl neel (e.g., a substituted or unsubstituted a C0 to C30 amino method is provided for obtaining, substituted or a substituted or unsubstituted C1 to C30 substituted or unsubstituted C6 to C30 opinion gun neel it will be biting or a substituted or alkylsulfonyl) or combinations thereof and, or R⁴¹ To R⁴³ Is a fused ring is coupled to the two adjacent form,

L¹ To L³ Are each independently single bond, a C1 to C30 substituted or unsubstituted alkylene, substituted or a substituted or unsubstituted C6 to C30 it will be biting, [leyn, 2 is a substituted or unsubstituted C3 to C30 and a hetero [...] of or a combination of these,

R⁵¹ To R⁵³ Are each independently a substituted or unsubstituted C1 to C30 alkyl group a, a C1 to C30 substituted or unsubstituted alkoxy group, a C6 to C30 substituted or unsubstituted aryl group, a substituted or unsubstituted C3 to C30 hetero [...], substituted or unsubstituted C1 to C30 alkoxy substituted or, a substituted or unsubstituted amine (e.g., a substituted or unsubstituted C1 to C30 alkyl or a substituted or a substituted or unsubstituted C6 to C30 a hydroxybutyrolactone [...]), a silyl group and a substituted or unsubstituted or a combination of these,

0 To 4 a to c are each independently an integer.

Said selectively absorbing green light of number 2 100 parts by weight of about 500 to about 1500 p type semiconductor compound the above compound parts by weight incorporated now.

Active layer (30) may be a single layer a plurality layer disapproval. Active layer (30) in the intrinsic layer (instrinsic layer, layer I) example, p/I-shaped layers layer, I layer/n-shaped layers, layer/n-shaped layers p/I-shaped layers, various combinations such as type/n be a p-shaped layers.

In the intrinsic layer (I layer) is about 1:100 to about 100:1 p type semiconductor and mixed-thickness of n-type semiconductor can comprise (or volume ratio). Said about 1:50 to 50:1 (or volume ratio) within the range of thickness can be comprising, within a range of about 1:10 to 10:1-thickness (or volume ratio) into said can, said-thickness can be within the range of about 1:1 comprising (or volume ratio). By having said effective range of composition ratio generating and pn junction OLEDs advantageously disclosed.

Said p-shaped layers and the above compound, comprising said n type layer is said n-type semiconductor can be.

Active layer (30) is about 1 nm to about 500 nm may have a thickness of. About 5 nm to 300 nm in thickness of said range may have. Said thickness range of the light by having the holes and the electrons absorb effectively separate and delivery by can be effectively improve photoelectric conversion efficiency. Photoelectric device (100) includes a number 1 electrode (10) and/or number 2 electrode (20) enter light from the active layer (30) can be generated in a predetermined wavelength region control part 1000 ppm in light absorbing. Exciton active layer (30) and the electrons in separated into, separate the holes pass number 1 electrode (10) and number 2 electrode (20) is moved the anode side one of electrons separated number 1 electrode (10) and number 2 electrode (20) on the cathode side is the other of the electric current to move the photoelectric device is equal to or higher.

2 Hereinafter refer to photoelectric device according to other embodiments also are disclosed therein.

Figure 2 shows a cross-section according to another embodiments shown photoelectric element are disclosed.

The reference 2 also, the embodiments according to photoelectric device (100) includes opposing coping implementation such as number 1 electrode (10) and number 2 electrode (20), and number 1 electrode (10) and number 2 electrode (20) positioned between the organic layer (30) comprises.

However the embodiments according to photoelectric device (100) includes the aforementioned coping implementation with number 1 electrode (10) and the active layer (30) and between the number 2 electrode (20) and the active layer (30) have a charge auxiliary layer (40, 45) results are. Charge auxiliary layer (40, 45) active layer (30) isolated from the holes and the electrons for the electron transfer can be width hereinafter.

Charge auxiliary layer (40, 45) hole injection hereinafter for the hole injection layer (hole injecting layer, HIL), a hole transport layer (hole transporting layer, HTL) hereinafter for electron and hole transport, electron under electron blocking layer (electron blocking layer, EBL), electronic injection hereinafter for an electronically controlled injection layer (electron injecting layer, EIL), for transport of electrons (electron transporting layer, ETL) hereinafter under electron transport layer and holes of the hole blocking layer (hole blocking layer, HBL) can be at least one.

Charge auxiliary layer (40, 45) for example organic, inorganic or whether comprising a fluoride resin film can be. Said hole or electronic characteristics may be organic with organic compounds, said inorganic material may be a e.g. molybdenum oxide, tungsten oxides, be a metal oxide such as nickel oxide.

the hole transporting layer (HTL) such as poly (3, 4 - ethylenedioxythiophene): poly (styrene sulfonate) (poly (3, 4 a-ethylenedioxythiophene): poly (styrenesulfonate), PEDOT: PSS), polyaryl amine, poly (vinyl N - car it will doze) (poly (N n-vinylcarbazole), polyaniline (polyaniline), polypyrrole (polypyrrole), N, N, N', N' - tetrakis (4 - methoxyphenyl) - benzidine (N, N, N', N' - tetrakis (4 a-methoxyphenyl) - benzidine, TPD), 4, 4 '- bis [N - (1 - naphthyl) - N - phenyl - amino] biphenyl (4, 4' - bis [N - (1 a-naphthyl) - N a-phenyl a-amino] biphenyl, α-a NPD), m a-MTDATA, 4, 4 '4 "- tris (N - cover nocathiacin) - triphenyl amine (4, 4', 4" - tris (N-a carbazolyl) - triphenylamine, TCTA) and combinations thereof but selected from one of, limited to are not correct.

Said electron blocking layer (EBL) is poly (3, 4 - ethylenedioxythiophene): poly (styrene sulfonate) (poly (3, 4 a-ethylenedioxythiophene): poly (styrenesulfonate), PEDOT: PSS), polyaryl amine, poly (vinyl N - car it will doze) (poly (N n-vinylcarbazole), polyaniline (polyaniline), polypyrrole (polypyrrole), N, N, N', N' - tetrakis (4 - methoxyphenyl) - benzidine (N, N, N', N' - tetrakis (4 a-methoxyphenyl) - benzidine, TPD), 4, 4 '- bis [N - (1 - naphthyl) - N - phenyl - amino] biphenyl (4, 4' - bis [N - (1 a-naphthyl) - N a-phenyl a-amino] biphenyl, α-a NPD), m a-MTDATA, 4, 4 ', 4 "- tris (N - cover nocathiacin) - triphenyl amine (4, 4', 4" - tris (N-a carbazolyl) - triphenylamine, TCTA) and combinations thereof but selected from one of, limited to are not correct.

Example 2 - 1, 4, 5, 8 - naphthalene electron transport layer (ETL) said solution used for car [lu luck thread [lik (1, 4, 5, 8 a-naphthalene-a tetracarboxylic dianhydride, NTCDA), lancet [...] (bathocuproine, BCP), LiF, Alq3, Gaq3, Inq3, Znq2, Zn (BTZ) 2, it can be selected from one BeBq2 and combinations thereof, limited to are not correct.

1, 4, 5, 8 - Naphthalene - said hole blocking layer (HBL) 2 solution used for example car [lu luck thread [lik (1, 4, 5, 8 a-naphthalene-a tetracarboxylic dianhydride, NTCDA), lancet [...] (BCP), LiF, Alq3, Gaq3, Inq3, Znq2, Zn (BTZ) 2, it can be selected from one BeBq2 and combinations thereof, limited to are not correct.

Said charge auxiliary layer (40, 45) one can be avoided.

Solar cells said photoelectric device, Image sensor, photodetector, optical sensor and organic light emitting diode applied to but, limited to are not correct.

Hereinafter said photoelectric device for applying one example of Image sensor with reference to a drawing through a browser substrate. One example of organic CMOS Image sensor to calibrate the Image sensor is described substrate.

Figure 3 shows a plane view and also in one implementation to determine the Image sensor according to organic CMOS shown, Figure 4 shows a cross-section of Figure 3 organic CMOS Image sensor are disclosed.

The reference 3 and 4 may also, in one implementation according to organic CMOS Image sensor (300) is light sensing elements (50B, 50R), transfer transistor (not shown) and charge reservoir (55) a semiconductor substrate having integrated (310), insulating layer (60), color filter layer (70), upper insulating layer (80) and photoelectric device (100) having a predetermined wavelength.

Semiconductor substrate (310) can be a silicon substrate includes, light sensing elements (50B, 50R), transfer transistor (not shown) and charge reservoir (55) integrated in the nanometer range. Light sensing elements (50R, 50B) can be a light diode.

Light sensing elements (50B, 50R), formed on the/or charge reservoir (55) every pixel can be without removing respective, in one embodiment the light sensing elements as in drawing (50B, 50R) is blue and red pixel charge reservoir can be included (55) includes a pixel can be included.

Light sensing elements (50B, 50R) has light can be delivered by sensing the sensed information is transistor, charge reservoir (55) is carry photoelectric device (100) electrically coupled to the charge reservoir (55) can be delivered by the information of the transfer transistor.

Drawing light sensing element (50B, 50R) structure is shown illustratively without limited to but arranged side by side and blue light sensing element (50B) on red light sensing elements (50R) stacked vertically may be disclosed.

Semiconductor substrate (310) in addition on metal wiring (not shown) and the pad (not shown) is formed in the nanometer range. In order to reduce signal delays which low resistivity metal interconnection and pad of metal, such as aluminum (Al), copper (Cu), but may be made of the (g) and alloys thereof, limited to are not correct. However said structure without limit, metal wire and pad on the light sensing elements (50B, 50R) to be located beneath disapproval.

Metal wiring on the pad insulating layer (60) formed in the nanometer range. Insulating layer (60) is silicon oxide and/or nitride insulating material or SiC, SiCOH, a low dielectric constant (low K) such as SiOF SiCO and can be made of a material. Insulating layer (60) charge reservoir (55) has a trench on the data line. The trenches are filled with a filler can be disclosed.

Lower insulation (60) on the color filter layer (70) formed in the nanometer range. Color filter layer (70) blue pixel light sensing elements (50B) selectively overlapping to form a blue light blue filter (70B) operates to emit light on a pixel light sensing elements (50R) overlapping the selectively permeable yellow light is formed on the red filter (70R) without using a tool. The implementations described but does not exist at the green filter for example, the green filter when disapproval.

Color filter layer (70) can then if can be omitted, in one embodiment the blue light sensing elements (50B) on red light sensing elements (50R) is connected a vertically stacked gate electrode is formed blue light sensing elements (50B) on red light sensing elements (50R) is deposited according to the depth respective wavelength regions can be sensed or detected for selectively absorbing and/color filter layer (70) not with disapproval.

Color filter layer (70) on the upper insulating layer (80) formed in the nanometer range. Upper insulating layer (80) color filter layer (70) is formed on a stand-alone number and planarized to each other. Upper insulating layer (80) and insulating layer (60) opening (not shown) on the color green pixel charge reservoir (55) having a large area through hole (85) have.

Upper insulating layer (80) is formed on the aforementioned photoelectric device (100) is formed in the nanometer range. Photoelectric device (100) is such a number 1 as electrode (10), active layer (30) and number 2 electrode (20) comprises.

Number 1 electrode (10) and number 2 electrode (20) transparent electrode may be all, active layer (30) efined aforementioned. Active layer (30) can be selectively absorbing and/or green wavelength range of light sensing pixel color filters can be replace.

Number 2 electrode (20) through the light incident from the active layer (30) green wavelengths light range is mainly absorbed in the remaining wavelength region can be photoelectric conversion light number 1 electrode (10) through the light sensing elements (50B, 50R) of the sensing 1308.

Such as green wavelength range of light sensed or detected said selectively absorbing and/halide is laminated by pollution can be implementing Image sensor of Image sensor size.

In addition, the above-mentioned p or n type semiconductor as a compound as aforementioned by deposition phase and/or succeeding stages prevents deterioration of stable compound in absorbing characteristics, electrical characteristics and thermal characteristics can be implementing. The second green wavelengths selectivity can be thereby eliminating absorbs green other than wavelength range of light and reduce crosstalk can be generated by the first magnet.

In Figure 4 of Figure 1 includes organic photoelectric device (100) including a limited example of Figure 2 but shown without organic photoelectric device (200) including a can even when force. Figure 5 shows a photoelectric device (200) for applying organic CMOS Image sensor (400) shown is a cross-sectional drawing of Figure 2.

Figure 6 shows a cross-section according to another embodiments shown to determine organic CMOS Image sensor also are disclosed.

With reference to the 6 also, the embodiments according to organic CMOS Image sensor (500) is coping implementation such as light sensing elements (50B, 50R), transfer transistor (not shown) and charge reservoir (55) a semiconductor substrate having integrated (310), insulating layer (80) and photoelectric device (100) having a predetermined wavelength.

However the embodiments according to organic CMOS Image sensor (500) is coping with such implementation, blue light sensing elements (50B) on red light sensing elements (50R) insulation film color difference and filter layer (70) can be avoided. Blue light sensing elements (50B) on red light sensing elements (50R) and electrically connected to the reservoir and the charge transfer transistor (not shown) can be delivered by. Blue light sensing elements (50B) on red light sensing elements (50R) is laminated according to the depth for selectively absorbing and/respective wavelength regions can be sensed or detected.

Such as green wavelength range of light sensed or detected said selectively absorbing and/halide laminated construction red light sensing elements and blue light sensitive device is laminated by implementing Image sensor of Image sensor size can be further reduced. In addition as the aforementioned organic photoelectric device (100) includes a SKT into the wavelength range of light other than green wavelengths by increasing selectivity green pixel data signal to the first absorption can be reduce.

In Figure 6 of Figure 1 is organic photoelectric device (100) including a limited example of Figure 2 but shown without organic photoelectric device (200) including a can even when force.

Figure 7 shows a CMOS Image sensor according to another embodiments shown in regards to determine organic also are disclosed.

With reference to the 7 also, the green wavelength range of light organic CMOS Image sensor according to embodiments for selectively absorbing and/sensed or detected a green photoelectric (G), blue wavelength range of light sensed or detected for selectively absorbing and/blue photoelectric element (B) and red wavelength range of light sensed or detected for selectively absorbing and/red photoelectric structure insulation film (R) are disclosed.

In photoelectric device drawing (R) red, blue and green component (G) (B) photoelectric device shown but in turn laminated structure, various stacking without limited to order can be varied.

Said photoelectric device is green (G) and such a photoelectric device (100) may be, said photoelectric device are selected from blue (B) interposed between facing electrodes 12 and blue wavelength range of light can be selectively absorbing organic matter including an active layer including, red (R) said photoelectric device is interposed between opposing electrodes 12 and red wavelength range of light including an active layer including organic matter can be selectively absorbing.

Such as said photoelectric device for selectively absorbing and/or green wavelength range of light sensing (G), and/or selectively absorbing blue wavelength range of light sensing (B) and red wavelength range of light photoelectric device selectively absorbing and/or sensing photoelectric device (R) is laminated by implementing Image sensor of Image sensor size can be further reduced to the first and can be reduce crosstalk.

Absorption of appropriate wavelength range by having said Image sensor sensitivity (YSNR10) (Δ E * ab) while having a stacked structure in which both can be on color reproducibility.

Here talking YSNR10 RM (Ogunquit Maine, USA) year 2007 and International Image Sensor Workshop numerical representation indicating sensitivity of Image sensor SUMMARY of a method of house "Image Sensors and Image Quality in Mobile Phones" Juha Alakarhu measured signal and noise ratio of 10 lux minimum roughness is represented in numerical or are disclosed. The smaller the value of the YSNR10 that can be highly sensitive.

While the color reproducibility (Δ E * ab) X-a Rite to some numerical representation indicating whether difference and standard color chart

CIE 1976 L * a * b * color space is Δ E * ab (station number lighting Committee) is the distance between the point on the year on 2 defining a numerical representation indicating are disclosed. E.g. [...] expressions can be calculated by said to 1.

[Mathematical equation 1]

Expressions in said 1,

Δ L^* Is at ordinary temperature (20 °C to 25 °C) color coordinate in L^* When compared to the color coordinate L^* And variation,

Δ a^* At ordinary temperature is in a color coordinate^* When compared to a color coordinate^* And variation,

Δ b^* At ordinary temperature is in color coordinate b^* When compared to the color coordinate b^* Exhibits a change.

In chromatic reproducibility and high Image sensor to obtain the highest sensitivity in at least one of compounds represented by said formula 1 to 4 one YSNR10 ≤ 100lux hereinafter Δ E * ab ≤ 3 needs when using Δ E * ab ≤ 3 YSNR10 ≤ 100lux in sensitivity of implementing function as can be.

Said Image sensor can be applied to various electronic device, e.g. mobile phone, digital camera applied to limited to but are not correct.

Hereinafter in the embodiment described above one embodiment through the corresponding business are provided as follows. In the embodiment just described is merely for purposes of relayed to form a number range which are not correct.

Synthesis example

Synthesis example 1

[Formula A provided 1]

[Reactive A provided 1]

(1 Provided i) compound (1) synthesis of

Tree butyl phosphine (tributylphosphine) 9. 74 G (48. 2 Mmol) and 1, 8 - 7 - diaryl java director claw fortune strongest (diazabicycloundec-a 7 a-ene) 0. 49 G (3. 2 Mmol) 10 ml methylene chloride (MC) thio snoop carboxaldehyde drying 10 to 2, 3 - (2, 3 a-thiophenedicarboxaldehyde) 4. 5 G (32. 1 Mmol) and dimethyl the [ley which it will carry on shoulder the [thu (dimethyl maleate) 4. 86 G (33. 7 Mmol) slowly to 1e14 ions in the other end drying MC 40 ml 0 °C. Silica gel column chromatography (developing solvent: MC) obtained product dimethyl benzo thiophene - 5, 6 - separated by the positive number (dimethyl benzo thiophene-a 5, 6 a-dicarboxylate) dicarboxylate 5. 2 G (yield 65%) obtain.

(1 A-ii) compound (2) synthesis of

NaH 60% in mineral oil 1. 66 G (41. 6 Mmol) and ethyl acetate (ethyl acetate) 4. 58 G (51. 9 Mmol) N - methyl - 2 - pyrrolidone (N a-methyl-a 2 a-pyrrolidone) a fully been rapidly, compound (1) 3. 0533G (1. 027 Mmol) slowly into the base 75 °C 6 decodes in a meat and mixing. 50 Ml 10 ml sulfate precipitated substances may melts back to line is determined in 10 minutes boiling substrate. Finally precipitated 5H - indeno [5, 6 a-b] thiophene filter material are separated from each other - 5, 7 (6H) - dione ([5, 6 a-b] thiophene-a 5, 7 - dione (6H) 5H non-indeno) 0. 23 G (yield 5%) to obtain.

(1 A-iii) compound (3) synthesis of

6. 8 Ml of N, N - dimethylformamide amide (N, N-a dimethylformamide) to 2. For the preparation of 1 (phosphoryl chloride) in a 2 ml -15 °C after gun [su gun reel is dripped at room temperature (24 °C) etched in 2 hours stirring. 180 Ml of dichloro methane (dichloromethane) 6 and same. 84 G of 10 - (the leno pen which it will count - 2 - yl) - 10H - -15 °C after 30 minutes stirring at room temperature slowly dripped in roh lung [ley najin which it will count which has hair cream or other. 100 Ml of water until the pH value 14 herein to add sodium hydroxide aqueous solution (aqueous sodium hydroxide) after adding at room temperature (24 °C) stirring time etched in 2. Ethyl acetate extraction of an aqueous sodium chloride (aqueous sodium chloride) (wash) (ethyl acetate) organic cleaning after magnesium sulfate anhydride (anhydrous magnesium sulfate) through the drying chamber. The resulting product can be separated by a silica gel column chromatography (hexane: at a volumetric ratio of methane to biocatalytic=3:2) to positive number 5 - (10H - roh lung [ley najin which it will count - 10 - yl) - 2 - cover the leno pen which it will count aldehyde (5 - (10H-a phenoselenazin provided 10 a-yl) selenophene provided 2 a-carbaldehyde) (compound (3)) 5. 16 G (yield 70%) obtain.

(1 A-iv) synthesis of compound represented by the following formula A provided 1

5 - (10H - roh lung [ley najin which it will count - 10 - yl) the leno pen which it will count car [pu it knows, the [tu - 2 - (5 - (10H-a phenoselenazin provided 10 a-yl) selenophene provided 2 a-carbaldehyde, compound (3)) 0. 31 G (0. 77 Mmol) suspending ethanol, excitation obtained compound (2) 0. 19 G (0. 94 Mmol) by adding, 50 °C reacting compounds represented by formula A-a 1 0 2 in time. 16 G (yield 90%) obtain. Sublimation positive number obtained compound with a purity 99. Positive number up to about 9%. Said formula A provided 1 represented by the following¹ Also 8 H NMR data shown in the other.

Synthesis example 2

[Formula A provided 2]

[Reactive A provided 2]

1. 2 A-Iodoselenophene (2 - iodine the leno pen which it will count)

2 - Five degree the leno pen which it will count (2 a-iodoselenophene) is Efficient Synthesis of 2 a-Iodo and 2 a-Dicyanomethyl Derivatives of Thiophene, Selenophene, Tellurophene, and Thieno [3, 2 a-b] thiophene, Takahashi, K. ; Tarutani, S. Heterocycles 1996, 43, 1927 - 1935 S. a synthesizing method.

2. 10H - roh lung [ley najin which it will count (10H provided phenoselenazine)

10H - triazines (purity 98% or more) for purchase in roh lung [ley najin which it will count mediator release from basophils (Medigen Inc.)

Reference document: Preparation and Some Reactions of Phenoxazine and Phenoselenazine, Paulette M?Ller, N. P. Buu a-H?I, and R. RIPS, J. Org. Chem. , 1959, 24 (1), Pp 37 - 39 t

3. 10 - (The leno pen which it will count - 2 - yl) - 10H - roh lung [ley najin which it will count (10 - (selenophen provided 2 a-yl) - 10H-a phenoselenazine) synthesis of

2 - Five degree the leno pen which it will count 13. 6G (52. 8 Mmol) and 10H - roh lung [ley najin which it will count 10. 0G (40. 6 Mmol) in 100 ml of anhydrous toluene 5mol % Pd (dba)₂ , 5Mol % of P (t provided Bu)₃ And 4. 29G (44. 7 Mmol) in the presence of NaOtBu, 120 °C 12 in refluxing time after cooled down to room temperature the substrate. The obtained product is subjected to silica gel column chromatography (toluene: hexane=1:4 volume ratio) separated by a positive number (the leno pen which it will count - 2 - yl) - 10H - roh lung [ley najin which it will count to 10 - (10 - (selenophen provided 2 a-yl) - 10H-a phenoselenazine) 6. 89 G (yield 45. 2%) Obtain.

4. 5 - (10H - roh lung [ley najin which it will count - 10 - yl) - 2 - cover the leno pen which it will count synthesis of aldehyde (5 - (10H-a phenoselenazin provided 10 a-yl) selenophene provided 2 a-carbaldehyde)

6. 8 Ml of N, N - dimethylformamide amide (N, N-a dimethylformamide) to 2. For the preparation of 1 (phosphoryl chloride) in a 2 ml -15 °C after gun [su gun reel is dripped at room temperature (24 °C) etched in 2 hours stirring. 180 Ml of dichloro methane (dichloromethane) 6 and same. 84 G of 10 - (the leno pen which it will count - 2 - yl) - 10H - -15 °C after 30 minutes stirring at room temperature slowly dripped in roh lung [ley najin which it will count which has hair cream or other. 100 Ml of water until the pH value 14 herein to add sodium hydroxide aqueous solution (aqueous sodium hydroxide) after adding at room temperature (24 °C) stirring time etched in 2. Ethyl acetate extraction of an aqueous sodium chloride (aqueous sodium chloride) (wash) (ethyl acetate) organic cleaning after magnesium sulfate anhydride (anhydrous magnesium sulfate) through the drying chamber. The resulting product can be separated by a silica gel column chromatography (hexane: at a volumetric ratio of methane to biocatalytic=3:2) to positive number 5 - (10H - roh lung [ley najin which it will count - 10 - yl) - 2 - cover the leno pen which it will count aldehyde (5 - (10H-a phenoselenazin provided 10 a-yl) selenophene provided 2 a-carbaldehyde) (compound (3)) 5. 16 G (yield 70%) obtain.

5. Synthesis of compound A provided 2

5 - (10H - roh lung [ley najin which it will count - 10 - yl) - 2 - aldehyde 2 cover the leno pen which it will count. 5G (6. 20Mmol) 5H - indeno [5, 6 a-b] and the leno pen which it will count - 5, 7 (6H) - ((6H) - dione [5, 6 a-b] 5H non-indeno selenophene-a 5, 7) won die 2. 00G (8. 06Mmol) stirring in a 250 ml ethanol 80 ml by adding 4 decodes 60 °C rounded cap less affected by time. Stirring at ambient temperature for 30 minutes then adding 150 ml n - hexane temperature reduce etched. Then obtain are cleaned crude n - hexane. A 450 ml chloroform and then placed into a heated agitating said crude 2L function cap less affected by 70 °C melting substrate. N - hexane added to 700 ml then beaded evaporants and obtain product and filter temperature is decreased down to the normal temperature. Purity 99. 9% Said positive number to the re-precipitation repeatedly transmitting the other. 2 Hours after completion of 150 °C positive number in a stand-alone (Z) the number remaining vacuum drying cyclohexane - 6 - ((5 - (10H-a phenoselenazin provided 10 a-yl) selenophen provided 2 a-yl) methylene) (6H) - dione - 5H-a indeno [5, 6 a-b] selenophene-a 5, 7 (compound A provided 2) 3. 02G obtain. Or sublimation in 2 hours baking when positive number 150 °C disapproval. The yield is 83%.

Said formula A provided 2 represented by the following¹ Also 9 H NMR data shown in the other.

Synthesis example 3

[Formula A provided 3]

1. 2 A-Iodoselenophene (2 - iodine the leno pen which it will count)

2 - Five degree the leno pen which it will count (2 a-iodoselenophene) is Efficient Synthesis of 2 a-Iodo and 2 a-Dicyanomethyl Derivatives of Thiophene, Selenophene, Tellurophene, and Thieno [3, 2 a-b] thiophene, Takahashi, K. ; Tarutani, S. Heterocycles 1996, 43, 1927 - 1935 S. a synthesizing method.

2. 5, 5 - Dimethyl - 5, 10 - [1, 8] naphthyridine [...] ([b] [1, 8] naphthyridine 5, 5 a-dimethyl-a 5, 10 a-dihydrobenzo)

5, 5 - Dimethyl - 5, 10 - [1, 8] [...] unicast (purity 98% or more) plus other stored in my petit [tin.

Reference document: Preparation and Some Reactions of Phenoxazine and Phenoselenazine, Paulette M?Ller, N. P. Buu a-H?I, and R. RIPS, J. Org. Chem. , 1959, 24 (1), Pp 37 - 39 t

3. 5, 5 - Dimethyl - 10 - [1, 8] naphthyridine (the leno pen which it will count - 2 - yl) - 5, 10 - [...] (5, 5 a-dimethyl-a 10 - (selenophen provided 2 a-yl) - [1, 8] naphthyridine 5, 10 a-dihydrobenzo)

2 - 5, 5 - Dimethyl - 5, 10 - [1, 8] using the leno pen which it will count and iodine - 10 - 5, 5 - dimethyl [...] my petit [tin [1, 8] (the leno pen which it will count - 2 - yl) - 5, 10 - [...] obtain my petit [tin.

4. 5 - (5, 5 A-dimethylbenzo [a b] [1,8] naphthyridin-a 10 (5H) - yl) selenophene provided 2 a-carbaldehyde

6. 8 Ml of N, N - dimethylformamide amide (N, N-a dimethylformamide) to 2. For the preparation of 1 (phosphoryl chloride) in a 2 ml -15 °C after gun [su gun reel is dripped at room temperature (24 °C) etched in 2 hours stirring. 180 Ml of dichloro methane (dichloromethane) 6 and same. 84 G of 10 - (the leno pen which it will count - 2 - yl) - 10H - -15 °C after 30 minutes stirring at room temperature slowly dripped in roh lung [ley najin which it will count which has hair cream or other. 100 Ml of water until the pH value 14 herein to add sodium hydroxide aqueous solution (aqueous sodium hydroxide) after adding at room temperature (24 °C) stirring time etched in 2. Ethyl acetate extraction of an aqueous sodium chloride (aqueous sodium chloride) (wash) (ethyl acetate) organic cleaning after magnesium sulfate anhydride (anhydrous magnesium sulfate) through the drying chamber. The resulting product can be separated by a silica gel column chromatography (hexane: at a volumetric ratio of methane to biocatalytic=3:2) to positive number 5 - ([1, 8] naphthyridin-a 10 5, 5 a-dimethylbenzo (5H) - yl) selenophene provided 2 a-carbaldehyde 5. 16 G (yield 70%) obtain.

5. (Z)- 6 - ((5 - (5, 5 a-dimethylbenzo [1, 8] naphthyridin-a 10 (5H) - yl) selenophen provided 2 a-yl) methylene) (6H) - dione - 5H-a indeno [5, 6 a-b] thiophene-a 5, 7 synthesis

5 - (10H-a phenoselenazin provided 10 a-yl) selenophene provided 2 a-carbaldehyde 2. 5G (6. 20Mmol) and 5H-a 5,6 indeno [a-b]thiophene-a 5, 7 (6H) - dione 1. 60G (8. 06 Mmol) in 250 ml ethanol 80 ml by adding 60 °C 4 decodes a rounded cap less affected by stirring time. Stirring at ambient temperature for 30 minutes then adding 150 ml n - hexane temperature reduce etched. Then the filtration of the crude n - hexane to obtain. In 450 ml 70 °C heated to melting and agitating said crude [...] 2L function cap less affected by a substrate. N a-Hexane 700 ml then added at ambient temperature and temperature of a drip-evaporants barrier film. Then filtering to obtain a product. Purity 99. 9% Said positive number to the re-precipitation repeatedly transmitting the other. 2 Hours after completion of positive number 150 °C cyclohexane compounds A provided 3 3 number remaining vacuum drying in a stand-alone. 02G obtain. Or sublimation in 2 hours baking when positive number 150 °C disapproval. The yield is 83%.

Said formula A provided 3 represented by the following¹ 10 Also H NMR data shown in the other.

Synthesis example 4

[Formula B provided 1]

[Reactive B-a 1]

(1 Provided i) compound (1) synthesis of

2 A-iodothieno [3, 2 a-b] thiophene (compound (1)) is Efficient Synthesis of 2 a-Iodo and 2 a-Dicyanomethyl Derivatives of Thiophene, Selenophene, Tellurophene, and Thieno [3, 2 a-b] thiophene, Takahashi, K. ; Tarutani, S. Heterocycles 1996, 43, 1927 - 1935 S. a synthesizing method.

(1 A-ii) compound (2) synthesis of

Compound (1) 13. 6G (52. 8 Mmol) and 10H provided phenoselenazine 10. 0G (40. 6 Mmol) in 100 ml of anhydrous toluene 5 mol % Pd (dba)₂ , 5 Mol % of P (tBu)₃ And 4. 29G (44. 7 Mmol) in the presence of NaOtBu, 2 time heating reflux to each other. The resulting product can be a silica gel column chromatography (toluene: hexane=1:4 volume ratio) separated by a positive number the compounds (2) 6. 89 G (yield 45. 2%) Obtain.

(1 A-iii) compound (3) synthesis of

6. 8 Ml of N, N - dimethylformamide amide (N, N-a dimethylformamide) to 2. For the preparation of 1 (phosphoryl chloride) in a 2 ml -15 °C after gun [su gun reel is dripped at room temperature (24 °C) etched in 2 hours stirring. 180 Ml of dichloro methane (dichloromethane) 6 on same. 84 G of compound (2) stirring at room temperature 30 minutes after mixing to -15 °C slowly dripped in the cream or other. 100 Ml of water until the pH value 14 herein to add sodium hydroxide aqueous solution (aqueous sodium hydroxide) after adding at room temperature (24 °C) stirring time etched in 2. Ethyl acetate extraction of an aqueous sodium chloride (aqueous sodium chloride) (ethyl acetate) after washing of the organic layer (wash) anhydrous magnesium sulfate (anhydrous magnesium sulfate) through the drying chamber. The resulting product can be separated by a silica gel column chromatography (hexane: at a volumetric ratio of methane to biocatalytic=3:2) positive number the compounds (3) 5. 16 G (yield 70. 4%) To obtain.

(1 A-iv) synthesis of compound represented by the following formula B provided 1

Obtained compound (3) 2. 00 G (4. 96 Mmol) suspending ethanol, 1H-a cyclopenta naphthalene-a 1, 3 herein (2H) - dione 1. 46 G (7. 44 Mmol) by adding, in time 2 50 °C reacting compounds represented by formula B provided 1 (4) 2. 62 G (yield 90%) obtain. Sublimation positive number obtained compound with a purity 99. Positive number up to about 9%.

Said formula B provided 1 represented by the following¹ Also 11 H NMR data shown in the other.

Synthesis example 5

[Formula C-a 1]

[Reactive C-a 1]

(1 Provided i) compound (1) synthesis of

2 - Five degree the leno pen which it will count (2 a-iodoselenophene) is Efficient Synthesis of 2 a-Iodo and 2 a-Dicyanomethyl Derivatives of Thiophene, Selenophene, Tellurophene, and Thieno [3, 2 a-b] thiophene, Takahashi, K. ; Tarutani, S. Heterocycles 1996, 43, 1927 - 1935 S. a synthesizing method.

(1 A-ii) compound (2) synthesis of

2 - Five degree the leno pen which it will count 13. 6G (52. 8 Mmol) and 10H provided phenoselenazine 10. 0G (40. 6 Mmol) in 100 ml of anhydrous toluene 5 mol % Pd (dba)₂ , 5 Mol % of P (tBu) 3 and 4. 29G (44. 7 Mmol) in the presence of NaOtBu, 2 time heating reflux to each other. The resulting product can be a silica gel column chromatography (toluene: hexane=1:4 volume ratio) separated by a positive number by 10 - (selenophen provided 2 a-yl) - 10H-a phenoselenazine 6. 89 G (yield 45. 2%) Obtain.

(1 A-iii) compound (3) synthesis of

6. 8 Ml of N, N - dimethylformamide amide - d7 (N, N-a dimethylformamide-a d7) to 2. For the preparation of 1 (phosphoryl chloride) in a 2 ml -15 °C after gun [su gun reel is dripped at room temperature (24 °C) etched in 2 hours stirring. 180 Ml of dichloro methane (dichloromethane) 6 and same. 84 G of compound (2) stirring at room temperature 30 minutes after mixing to -15 °C slowly dripped in the cream or other. 100 Ml of water until the pH value 14 herein to add sodium hydroxide aqueous solution (aqueous sodium hydroxide) after adding at room temperature (24 °C) stirring time etched in 2. Ethyl acetate extraction of an aqueous sodium chloride (aqueous sodium chloride) (ethyl acetate) after washing of the organic layer (wash) anhydrous magnesium sulfate (anhydrous magnesium sulfate) through the drying chamber. The resulting product can be separated by a silica gel column chromatography (hexane: at a volumetric ratio of methane to biocatalytic=3:2) positive number the compounds (3) 5. 16 G (yield 66%) obtain.

(1 A-iv) compound (4) synthesis of

Obtained compound (3) 2. 00 G (4. 96 Mmol) suspending ethanol, 1H-a cyclopenta naphthalene-a 1, 3 herein (2H) - dione 1. 46 G (7. 44 Mmol) added, reacting compounds represented by formula C-a 1 2 2 50 °C in time. 62 G (yield 66%) obtain. Sublimation positive number obtained compound with a purity 99. Positive number up to about 9%.

Said formula C-a 1 represented by the following¹ Also 12 H NMR data shown in the other.

¹ H NMR ppm (DMSO) 8. 33 - 8. 27 - 3H (m), 8. 24 - 8. 16 - 3H (m), 7. 98 - 2H (m), 7. 88 - 2H (m), 7. 71 (M) 2H, 7. 61 (T)- 2H, 7. 45 - 2H (t), 6. 61 (D)- 1H

Synthesis example 6

[Formula C-a 2]

In synthetic example 1 N, N - dimethylformamide instead of deuterium (deuterium) amide substituted N, N - dimethylformamide [...] a number in the range of 0.1 - d7 amide (N, N-a dimethylformamide-a d7) and, the same method synthesis example 1 synthesizing other.

Synthesis example 7

[Formula D-a 1]

[Reactive D-a 1]

In synthesis example 2, instead 10H - roh lung [ley najin which it will count 10H - phenothiazine (10H-a phenothiazine) synthetic example 2 identical to a number in the range of 0.1 [...] method according to obtain compounds represented by formula D-a 1.

Synthesis example 8

[Formula D-a 2]

[Reactive D-a 2]

In synthetic example 5, 2 - 5, 5 - dimethyl - 5, 10 - [1, 8] naphthyridine [...] instead of five degree the leno pen which it will count [2, 3 a-b] ([1, 8] naphthyridine [2, 3 a-b] 5, 5 a-dimethyl-a 5, 10 a-dihydropyrido) use N, N - dimethylformamide instead N - d7 amide, N - dimethylformamide the amide is in the range of 0.1 [...] number 5 identical to the method according to synthetic example obtain compounds represented by formula D-a 2.

Synthesis example 9

[Formula D provided 3]

[Reactive D provided 3]

Synthesis example 10

[Formula D-a 4]

[Reactive D-a 4]

Synthesis example 11

[Formula D provided 5]

[Reactive D provided 5]

(1 Provided i) [b, e] [1, 4] 10, 10 a-dimethyl-a 5, 10 a-dihydrodibenzo azasiline synthesis

Y. Kitamoto, T. Namikawa, T. Suzuki, Y. Miyata, H. Kita, T. Sato, S. Oi. Tetrahedron Letters 57 (2016) according to the method 4914 - 4917 disclosure of compounds (1) to synthesize other.

(1 A-ii) compound (1) synthesis of

I nitrogen atmosphere₂ 42. 6G (167. 89 Mmol) d ethyl ether anhydride (anhydrous diethyl ether) a reconstituted substrate. Then cedar 1L round bottom cap (3 a-neck round bottom flask) 250 ml dropping to the leno pen which it will count (selenophene) moving the atmosphere which it will peel and nitrogen atmosphere 20. 0G (152. 62 Mmol) after transferring d ethyl ether anhydride 400 ml reconstituted substrate. Then dropping in the atmosphere which it will peel n - butyl lithium (n a-butyllithium) (2. 5M in diethylether) transferring slowly after adding substrate. The temperature is maintained at 30 °C hereinafter added to control the rate of substrate. D ethyl ether then dropping the atmosphere which it will peel the wall surfaces of the washed the anhydride, etched in 30 minutes stirring 50 °C. I then melting in d ethyl ether₂ After stirring at room temperature in the atmosphere which it will peel -78 °C adding 12 decodes time slowly transferred in pitch. The layer which will bite into 400 ml distilled water then extracted 2 times 200 ml ethyl ether useful particularly as 3 difference. Then NaHSO₃ I main major portions remaining after the organic layer with an aqueous solution₂ The interval between a (quenching) each other. Then MgSO moisture organic layer₄ Eq (rotary evaporator) to a stand-alone number d ethyl ether and rotor using a number in a stand-alone compounds (1) 37. 3G obtain. The yield is 95%.

(1 A-iii) compound (2) synthesis of

A 250 ml round bottom cap to cedar (reflux condenser) is installed under nitrogen atmosphere anhydrous toluene (anhydrous toluene) ripple is brazed condenser 90 ml recoupled with the substrate. Toluene by substituting 3 times then vacuum and nitrogen state degassing etched. Then Pd (dba) here₂ 1. 17G (2. 03 Mmol) and t-a Bu₃ P (1. 0M in toluene) 2. 0 Ml (2. 03 Mmol) stirring after transferring etched. Then [b, e] [1, 4] 10, 10 a-dimethyl-a 5, 10 a-dihydrodibenzo azasiline 9. 15 G (40. 6 Mmol), 2 a-Iodoselenophene 13. 6 G (52. 8 Mmol) and NaOtBu 4. 29 G (44. 7 Mmol) in 5 time transferring 100 °C after refluxing the other. Then at ambient temperature for temperature (Celite) toluene in a stand-alone after rotation Eq number filter reduce light 2000 2000. Then toluene: n - hexane=1:9 (v/v) silica column chromatography through positive number ratio of the compounds (2) 10. 0G obtain (Rf: 0. 3). The yield is 76%.

NMR 1H NMR (300 MHz, CD2Cl 2): δ (ppm) 8. 12 (Dd, J=6. 0, 1. 2 Hz, 1H), 7. 55 (Dd, J=1. 5, 7. 2 Hz, 2H), 7. 33 (Dd, J=6. 0, 3. 6 Hz, 1H), 7. 2 - 7. 3 (M, 2H), 7. 12 (Dd, J=1. 2, 3. 6 Hz, 1H), 7. 01 (Dt, J=0. 9, 7. 2 Hz, 2H), 6. 93 (D, J=9. 7 Hz, 2H), 0. 48 (S, 6H)

(1 A-iv) compound (3) synthesis of

N 25 ml round bottom cap to nitrogen atmosphere, N-a dimethylformamide (DMF) of at least about 2. 0 Ml transferred to the substrate. Then -10 °C ice bath (ice bath, NaCl (use of KI) makes ice temperature by adding customized) in phosphorous oxychloride (phosphorus oxychloride, POCl₃ ) 0. 66 Ml (7. 10 Mmol) slowly at room temperature 1 hour or more syringe to adding agitating reagent 4700. Solution transparent yellow in color, red then vary in making sure that the other. Then 500 ml round bottom cap nitrogen atmosphere 10, 10 a-dimethyl-a 5 - [b, e] (selenophen provided 2 a-yl) - [1, 4] 5, 10 a-dihydrodibenzo azasiline 1. 93G (5. 46 Mmol) dichloro methane (dichloromethane, MC) a 180 ml reconstituted with substrate (yellow). Said solution by adding red brown color in said reagents prepared on ice bath slowly vary in making sure that the other. 3 Been rapidly adding distilled water 200 ml NaOH aqueous solution at room temperature then 1 time difference is added to pH 14 and n is an integer. 1 Dichloro methane extraction of saturated NaCl aqueous solution after stirring time and wash organic layer's desire. MgSO4 then dichloro methane organic layer after wetting ability in a stand-alone moisture number Eq rotation number 2000. Silica column chromatography then positive number to each other. In eluent (eluent) dichloro methane (MC) the positive column number: n - hexane=2:3 (n a-hexane) initiates a starting material at a rate of from impurities such as dichloro compound using the eluent methane after (3) 1. 56G obtain (Rf: 0. 3 (MC)). The yield is 75%.

NMR 1H NMR (300 MHz, CD2Cl 2): δ (ppm) 9. 45 (S, 1H), 7. 69 (D, J=7. 8 Hz, 2H), 7. 62 - 7. 75 (M, 3H), 7. 46 (Td, J=7. 8, 1. 8 Hz, 2H), 7. 33 (Td, J=7. 2, 1. 2 Hz, 2H), 6. 34 (D, J=4. 8 Hz, 1H), 0. 41 (S, 6H)

(1 A-v) final synthesis of compound

Compound (3) 1. 146G (2. 99 Mmol) compound (4) 0. 600G (3. 05 Mmol) cedar decodes a round bottom cap is placed N2 gas purge. Then 12 hours in 80 ml ethanol herein adding 75 provided 80 °C decodes ripple is brazed. The resulting product can be a room temperature (25 °C) water is added is formed as follows. Powder is generated when powder filtering substrate. Then by performing recrystallization using chloroform ethanol compounds represented by formula D-a 5 1. 205G obtain. The yield 71% are disclosed.

Synthesis example 12

[Formula D provided 6]

[Reactive D provided 6]

Compound (3) 1. 89G (4. 94 Mmol) compound (5) 1. 300G (5. 21 Mmol) cedar decodes a round bottom cap is placed N2 gas purge. Then 12 hours in 80 ml ethanol herein adding 75 provided 80 °C decodes ripple is brazed. The resulting product can be a room temperature (25 °C) water is added is formed as follows. Powder is generated when powder filtering substrate. Then chloroform ethanol by performing recrystallization using compound 2 represented by formula D provided 6. 2G obtain. The yield 72% are disclosed.

Synthesis example 13

[Formula D provided 7]

[Reactive D provided 7]

Compound (3) 1. 58G (4. 94 Mmol) compound (6) 0. 700G (4. 60 Mmol) cedar decodes a round bottom cap is placed N2 gas purge. Then 12 hours in 80 ml ethanol herein adding 75 provided 80 °C decodes ripple is brazed. The resulting product can be a room temperature (25 °C) water is added is formed as follows. Powder is generated when powder filtering substrate. Then by performing recrystallization using chloroform ethanol compounds represented by formula D-a 7 1. 65G obtain. The yield 77% are disclosed.

I evaluation

Synthesis example 1 to 13 according to compound thermal stability evaluation as follows.

10% Weight loss temperature (Ts, deposition temperature) in heat stability is 10Pa evaluates from, temperature higher than a melting point of compound (Tm) (Ts) deposited real good thin film deposition compound can be.

Said temperature loss weight analysis (thermal gravimetric analysis, TGA) method measuring substrate.

The result table 1 such as disclosed.

* Tm (°C): melting point of compound, compound decomposition temperature of

(°C)* Ts: deposition temperature, 10Pa reducing burn-in temperature of sublimation compound in 10% point

With reference to the table 1, the deposition compound having a melting point compounds are synthetic example 1 to 13 according to a thin film can be formed without disassembly of good can confirm it.

Film forming

Number attainments 1

Synthesis example 1 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 2

Synthesis example 2 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 3

Synthesis example 3 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 4

Synthesis example 4 according to a 1:1 compound C60-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 5

Synthesis example 5 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 6

Synthesis example 6 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 7

Synthesis example 7 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 8

Synthesis example 8 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 9

Synthesis example 9 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 10

Synthesis example 10 according to a 1:1 C60 compound to form a thin film of the type of time stamp-thickness (or volume ratio).

Number attainments 11

Synthesis example 11 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 12

Synthesis example 12 according to a 1:1 C60 compound-thickness to form a thin film of the type of time stamp (or volume ratio).

Number attainments 13

Synthesis example compound 13 according to a time stamp to form a thin film of the type of a 1:1 C60-thickness (or volume ratio).

Evaluation II

Attainments number 1 to 13 according to thin film of absorption characteristics other.

(Varian yarn number bath) - Cary 5000 UV spectroscopy using ultraviolet absorbing characteristic is visible (UV-a Vis) evaluated using each other.

Table 2 result such as disclosed.

Table 2 the reference, number 1 to 13 according to thin film is absorbing properties and good state is defined in the attainments green wavelengths is also used for selective wavelength can be.

Small number of photoelectric device

In the embodiment 1

An electrically conductive ITO thickness of about 150 nm on the glass substrate by laminating a sputtering method for producing synthetic example 1 according to compound C60 (n type semiconductor) 1:1 (p type semiconductor) and a second active layer-thickness to form a detachable time stamp (or volume ratio). Then the active layer in the thin film thickness 10 nm molybdenum oxide (MoOx, 0<x ≤ 3) charge auxiliary layer are laminated, ITO sputtering cathode 7 nm thickness formed thereon by laminating a small number photoelectric etched.

In the embodiment 2

Synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and 2 according to the same method instead of compound synthesis example number [...] decodes the photoelectric small number.

In the embodiment 3

Synthesis example 3 according to synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and the same method instead of compound number [...] decodes the photoelectric small number.

In the embodiment 4

Synthesis example 4 according to synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and the same method instead of compound number [...] decodes the photoelectric small number.

In the embodiment 5

Synthesis example 5 according to synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and the same method instead of compound number [...] decodes the photoelectric small number.

In the embodiment 6

Synthesis example 6 according to example 1 according to the range of 0.1 in the embodiment 1 and the same number [...] compound instead of compound synthesis method decodes the photoelectric small number.

In the embodiment 7

Synthesis example 7 according to synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and the same method instead of compound number [...] decodes the photoelectric small number.

In the embodiment 8

Synthesis example 8 according to synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and the same method instead of compound number [...] decodes the photoelectric small number.

In the embodiment 9

Synthesis example 9 according to synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and the same method instead of compound number [...] decodes the photoelectric small number.

In the embodiment 10

Synthesis example 1 according to compounds in the range of 0.1 and 10 according to the same method in the embodiment 1 instead of compound synthesis example number [...] decodes the photoelectric small number.

In the embodiment 11

Synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and 11 according to the same method instead of compound synthesis example number [...] decodes the photoelectric small number.

In the embodiment 12

Synthesis example 12 according to synthesis example 1 according to compounds in the range of 0.1 in the embodiment 1 and the same method instead of compound number [...] decodes the photoelectric small number.

In the embodiment 13

Synthesis example 1 according to compound 13 according to number in the range of 0.1 in the embodiment 1 and the same method instead of compound synthesis example [...] decodes the photoelectric small number.

Evaluation III

In the embodiment 1 to 13 according to photoelectric device of absorption and electrical characteristics other.

(Varian yarn number bath) - Cary 5000 UV spectroscopy using ultraviolet absorbing characteristic is visible (UV-a Vis) evaluated using each other.

The external quantum efficiency (EQE) IPCE measurement system (McScience yarn, Korean) equipment by using a substrate. First, Si photodiode (Hamamatsu yarn, Japan) using equipment (calibration) correcting after about 350 to about 750 nm wavelength range in the embodiment 1 to 6 according to photoelectric equipment is mounted on the external quantum efficiency (EQE) in measuring substrate. The external quantum efficiency of photovoltaic elements 170 °C 3 after leaving high temperature about 350 to about 750 nm wavelength range in solution in the same hardware by using a substrate.

The result table 3 such as disclosed.

With reference to the table 3, in the embodiment according to a photovoltaic device comprises external quantum efficiency is defined in exhibit green wavelengths thereby maintaining good optical catalyst at high temperatures can be left after T easy vector.

In the embodiment detailed above are implemented that are not limited to include a number of the SFC but chamber defined in the claims and then using one skilled general outline of an elementary form in addition various modified and improved in a range of rights are disclosed.