ORGANIC COMPOUND, COMPOSITION, ORGANIC PHOTOELECTRONIC DEVICE AND DISPLAY DEVICE

Hereinafter, one embodiment of the present invention detailed the on-sensors other. But, this is by way of example number so that when, the range of the present invention is defined by the present invention refers to one category number 802.11a packets not [...] claimed only disclosed.

The "substituted" in the definition of a specification without separate RM, substituent or at least one of hydrogen is deuterium, to halogen, hydroxy, amino group, a C1 to C30 substituted or unsubstituted amine, nitro, a C1 to C40 substituted or unsubstituted silyl group, C1 to C30 alkyl, C1 to C10 alkyl silyl group, C3 to C30 cycloalkyl, C3 to C30 hetero cycloalkyl, C6 to C30 aryl group, C3 to C30 hetero [...], C1 to C20 alkoxy, fluoro, C1 to C10 alkyl group such as trifluoromethyl trifluoromethyl, substituted cyano group or combinations thereof meaning that the other.

In one example of the present invention, "substituted" RM substituent or at least one of hydrogen is deuterium, amino group, a C1 to C30 substituted or unsubstituted amine, a C1 to C10 substituted or unsubstituted silyl group, C1 to C10 alkyl, C6 to C30 aryl, C3 to C30 hetero [...], meaning that the substituted cyano group or a combination of them to each other.

In one example of the present invention, "substituted" RM substituent or at least one of hydrogen is deuterium, C1 to C10 alkyl, C6 to C18 aryl group, C3 to C18 substituted hetero [...] or a combination of them meaning that the other. In addition said substituted for halogen, hydroxy, amino group, a C1 to C20 substituted or unsubstituted amine, nitro, substituted or substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl, C1 to C10 alkyl silyl group, C3 to C30 cycloalkyl, C3 to C30 hetero cycloalkyl, C6 to C30 aryl, C6 to C30 hetero [...], C1 to C20 alkoxy, fluoro group, C1 to C10 fluoroalkyl group such as trifluoromethyl or cyano group tree adjoining two substituent forms a ring fused to disapproval. For example, C6 to C30 substituted C6 to C30 adjacent another said substituted aryl group fused to a fluorene forms a ring can be substituted or unsubstituted.

The specification in the definition of "hetero" implies a separate free, one functional group in N, O, S, P and containing at least one hetero atoms selected from the group consisting of Si, the remainder being carbon may be used meaning that the other.

The specification is "aryl group (aryl group)" hydrocarbon group having at least one aromatic moiety in which broadly means aromatic moieties are single types and hydrocarbon aromatic moieties are hydrocarbon which is connected directly or indirectly fused non-aromatic fused ring in addition comprises. Active metal aryl, polycyclic or fused polycyclic (i.e., having carbon atoms of adjacent pairs formed between the ring) comprises functional groups.

The specification "hetero [...] (heterocyclic group)" in which the heteroaryl group including general outline, in addition to the aryl group, a cycloalkyl, a fusion of these ring or combinations thereof in cyclic compound such as carbon (C) instead of N, O, S, P and Si containing heteroatoms selected from at least one which means that the other. Said hetero ring giga when fused rings, each ring comprising one or more hetero [...] said all or each heteroatom can be.

More specifically, a substituted or unsubstituted C2 to C30 substituted or unsubstituted C6 to C30 aryl and/or a heterocyclic ring, a substituted or unsubstituted phenyl, a substituted or unsubstituted me [phu, a [...] substituted or unsubstituted, a substituted or unsubstituted lung difficulty [thu reel, cracked naphtha three neel substituted or unsubstituted, a substituted or unsubstituted neel blood [ley, bi-substituted or unsubstituted phenyl, a substituted or unsubstituted p - [...], m - [...] a substituted or unsubstituted, a substituted or unsubstituted three neel dirt, substituted or unsubstituted tree [...], substituted or a substituted or unsubstituted vinyl [ley neel, neel is a substituted or unsubstituted, a substituted or unsubstituted [...], abnormal substituted or unsubstituted phenyl, a substituted or unsubstituted pyrrole [...], substituted or unsubstituted [...] antagonist activity, a substituted or unsubstituted imidazole group, a substituted or unsubstituted triazole diary, substituted or a substituted or unsubstituted oxazole group, a substituted or unsubstituted thiazole group, a substituted or unsubstituted oxadiazole group, a substituted or unsubstituted thiadiazole group, substituted or unsubstituted [...] sealed, a pyrimido [...] substituted or unsubstituted, a substituted or unsubstituted [...] antagonist activity, triazoles [...] substituted or unsubstituted, a substituted or unsubstituted benzo [...], benzo [...] substituted or unsubstituted, a substituted or unsubstituted benzimidazole diary, a substituted or unsubstituted indole group, a substituted or unsubstituted [...], [...] isocyanate groups substituted or unsubstituted, a substituted or unsubstituted quinacridone-based neel it will doze, the [khwi stipend neel it will live a substituted or unsubstituted, a substituted or unsubstituted [...], substituted or nonsubstituted jade photograph substituted benzazepines diary, substituted or nonsubstituted substituted benzazepines benzothiazine diary, arc [...] substituted or unsubstituted, a substituted or unsubstituted lung najin diary, a substituted or unsubstituted phenothiazine diary, a diary lung stipendiary photograph substituted or unsubstituted, a substituted or unsubstituted five [ley neel and process for preparation thereof, substituted or nonsubstituted substituted dibenzo furan diary, a dibenzo [...] substituted or unsubstituted, a substituted or unsubstituted [...] cover, combinations thereof or combinations thereof can be a fused form, the 802.11a packets not one number.

In the specification, it will be biting, [leyn it will be biting, [leyn or a substituted or unsubstituted heteroaryl or a substituted or a substituted or unsubstituted 2 is a substituted or unsubstituted ring a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic inhibitors of coincidence in the meaning that the two heteroatoms [...] 2 connectors which, e.g., a substituted or unsubstituted phenylene, substituted or substituted or unsubstituted naphthalene, do not sprout three neel [leyn a substituted or unsubstituted, a substituted or unsubstituted lung difficulty [thu reel [leyn, cracked naphtha [...] substituted or unsubstituted, a substituted or unsubstituted neel [leyn blood [ley, substituted or unsubstituted back phenyl [leyn, a [...] substituted or unsubstituted, a substituted or unsubstituted phenyl [leyn quarter, regularly [...] substituted or unsubstituted, substituted or nonsubstituted substituted tri phenyl [ley neel [leyn, substituted or a substituted or unsubstituted vinyl [...], a [...] substituted or unsubstituted, a substituted or unsubstituted [...], a substituted or unsubstituted phenyl [leyn thio, substituted or unsubstituted pyrrole reel [leyn, substituted or unsubstituted [...] antagonist activity, one [leyn imidazole substituted or unsubstituted, a substituted or unsubstituted [...] triazoles, substituted or nonsubstituted substituted oxa [...], motors [...] substituted or unsubstituted, substituted in a substituted or unsubstituted oxadiazole one [leyn, motors [...] substituted or unsubstituted, substituted or unsubstituted sealed neel d [leyn, a substituted or unsubstituted pyrimidone neel d [leyn, a substituted or unsubstituted [...] antagonist activity, a substituted or unsubstituted triazoles [...], benzo [...] substituted or unsubstituted, a substituted or unsubstituted benzo-mote five phenyl [leyn, substituted or nonsubstituted [...] substituted benzazepines, one [leyn substituted or unsubstituted indolyl, substituted or nonsubstituted substituted [...], [...] isocyanate groups substituted or unsubstituted, a substituted or unsubstituted quinacridone-based [...], a [...] substituted or unsubstituted, a substituted or unsubstituted [...], substituted or nonsubstituted substituted benzazepines it will be a jade photograph, [leyn, substituted or nonsubstituted mote oh position one [leyn substituted benzazepines, arc neel d [leyn substituted or unsubstituted, a substituted or unsubstituted lung najin one [leyn, substituted or nonsubstituted substituted lung looking old oh position one [leyn, it will be a lung stipendiary photograph, [leyn a substituted or unsubstituted, a substituted or unsubstituted [...] and process for preparation thereof, substituted or nonsubstituted substituted dibenzo [...], a dibenzo mote five phenyl [leyn substituted or unsubstituted, a substituted or unsubstituted it will doze, [leyn cover, combinations thereof or combinations thereof can be a fused form, the number 802.11a packets not one.

In one example of the present invention, it will be biting, [leyn or a substituted or unsubstituted heteroaryl or a substituted or it will be biting, [leyn is a substituted or unsubstituted ring to a variety of substituted or unsubstituted 2 substituted or unsubstituted phenylene, substituted or unsubstituted back phenyl [leyn, a [...] substituted or unsubstituted, a substituted or unsubstituted phenyl [leyn quarter, substituted or substituted or unsubstituted naphthalene, a substituted or unsubstituted pyrimidine in range can be either or a combination of these. In the specification, provide the means by which carbon or heteroatom compound single bond connecting does not pass through coupling means which, for example, the meanings that substituents at the L L connected to a single coupling connected directly to the central core which means that the other. I.e., the specification is obtained via methylene carbon single bond in a will tastes.

In the specification, hole is obtained, applying the electric field (electric field) when a donor hole formed in saying that can be electronic, HOMO level formed in the light emitting layer has a hole injection anode along conductive properties, light emitting layer is formed anode movement and light emitting layer hereinafter for movement hole completely sealed by big.

In addition, electronic is obtained, the user can receive the characteristics when electrons in speaking therefore, LUMO level having conductive properties along the cathode formed in electronic light emitting layer injection, light emitting layer is formed of electrons cathode movement hereinafter for movement and a light emitting layer of thickness by big.

Hereinafter in one implementation according to organic compounds are described as follows.

In one implementation according to organic opto-electronic devices for compound that is represented by formula 1.

[Formula 1]

In said formula 1,

Ar¹ And Ar² Are each independently, a substituted or unsubstituted C1 to C20 alkyl, a C3 to C30 substituted or unsubstituted cycloalkyl, a substituted or unsubstituted C6 to C30 aryl group, or combinations thereof and,

R¹ Hydrogen, deuterium, a substituted or unsubstituted C6 to C30 alkoxy group,

R² To R⁵ Are each independently, hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl group, a C3 to C30 substituted or unsubstituted cycloalkyl, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 [...], a C1 to C30 substituted or unsubstituted alkoxy group, a substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 thread reel jade time, a C1 to C30 substituted or unsubstituted molecular weight alkyl, a substituted or unsubstituted C6 to C30 mote this year it will be biting, to halogen, cyano group, hydroxyl groups, amino, nitro, or combinations thereof and,

Substituted or unsubstituted [...] ET is sealed, will be and it will keep sealed by a substituted or unsubstituted, a substituted or unsubstituted pyrimidone [...], substituted or unsubstituted or a substituted or non-substituted triazoles the strangeness which it will keep [...] antagonist activity,

L is single bond, a substituted or unsubstituted C6 to C30 it will be biting, [leyn, substituted or substituted or unsubstituted C3 to C30 hetero it will be biting, [leyn or combinations thereof are disclosed.

In one example of the present invention, in said formula 1,

Ar¹ And Ar² Are each independently, a C1 to C10 substituted or unsubstituted alkyl, a substituted or unsubstituted C6 to C30 aryl group a, and or a combination of these,

R¹ Hydrogen, deuterium, a substituted or unsubstituted C6 to C30 alkoxy group,

R² To R⁵ Are each independently, hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl, a substituted or unsubstituted C6 to C18 aryl group, a substituted or unsubstituted C2 to C18 heteroaryl group, cyano group, or a combination of these and,

Substituted or unsubstituted [...] ET is sealed, will be and it will keep sealed by a substituted or unsubstituted, a substituted or unsubstituted pyrimidone [...], substituted or unsubstituted or a substituted or non-substituted triazoles the strangeness which it will keep [...] antagonist activity,

L is single bond, a substituted or unsubstituted C6 to C30 it will be biting, [leyn, substituted or substituted or unsubstituted C3 to C30 hetero it will be biting, [leyn or combinations thereof are disclosed.

In one example, said Ar¹ And Ar² Are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted phenyl-o -, m - a-substituted or unsubstituted phenyl, a substituted or unsubstituted p - biphenyl group, a substituted or unsubstituted phenyl fixed date be.

In one example, said Ar¹ , Ar² And R¹ Hydrogen, deuterium, a substituted or unsubstituted phenyl, substituted or unsubstituted back phenyl, substituted or substituted or unsubstituted naphthalene implementation being.

In one example, said L for a single bond or a substituted or unsubstituted phenylene, substituted or unsubstituted back phenyl [leyn, be a substituted or unsubstituted phenyl fixed date.

Organic compounds containing at least one nitrogen said formula 1 represented by including aromatic hexagonal [...], susceptible can be electrons upon applying an electric field to the electrode, the second electrode of said organic compounds and organic opto-electronic devices can be.

In addition, the indole roca it will doze said organic compounds are susceptible susceptible nitrogenated aromatic hexagonal hole portion together with [...] by electrons, bipolar (bipolar) and an insulating layer is of holes and electrons and properly balance and to flow, the organic compound and organic opto-electronic devices can be improves the efficiency of.

In addition, organic compounds by having said substantially linear in structure and which can enhance the process stability self aligned (self-a arrange) deposition film uniformity can be increase.

Said organic compound is for example, to formula 2 to 4 can be represented either.

[Formula 2]

[Formula 3]

[Formula 4]

In said formula 2 to 4, Ar¹ And Ar² , R¹ To R⁵ , ET, and aforementioned L efined.

For example, in one implementation according to said formula 2 to 4 in, Ar¹ And Ar² Are each independently, a substituted or unsubstituted phenyl, a substituted or unsubstituted phenyl or substituted or nonsubstituted bi-substituted triphenyl actuator disclosed.

For example, in one implementation in according to said formula 2 to 4, L to a substituted or unsubstituted phenylene, substituted or unsubstituted back phenyl [leyn or a substituted or unsubstituted triphenylene actuator disclosed.

For example, in one implementation in according to said formula 2 to 4, said ET is a substituted or unsubstituted pyridinyl, substituted or nonsubstituted substituted pyridazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted and substituted or unsubstituted antagonist activity or it will keep it will be neel triazoles, e.g., phenyl, phenyl-o -, m - bi-phenyl, and at least one substituted triazoles be phenyl-p - neel fixed date.

For example, in one implementation in according to said formula 2 to 4, said ET is a substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted or a substituted or non-substituted triazoles it will be neel be it will keep antagonist activity.

For example, in one implementation in according to said formula 2 to 4, said ET is substituted or unsubstituted pyrimidinyl, or it will be neel triazoles be substituted or unsubstituted.

Said formula 2 compounds represented by formula 2 - 1 to 2 - 4 can be represented as one.

[Formula 2 - 1]

[Formula 2 - 2]

[Formula 2 - 3]

[Formula 2 - 4]

In said formula 2 - 1 to 2 - 4, Ar¹ And Ar² , R¹ To R⁵ , ET, and L above are useful as aforementioned,

R⁶ And R⁷ Are each independently, hydrogen, deuterium, a C1 to C30 substituted or unsubstituted alkyl group, a C3 to C30 substituted or unsubstituted cycloalkyl, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 [...], a C1 to C30 substituted or unsubstituted alkoxy group, a substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 thread reel jade time, a C1 to C30 substituted or unsubstituted molecular weight alkyl, a substituted or unsubstituted C6 to C30 mote this year it will be biting, to halogen, cyano group, hydroxyl groups, amino, nitro, or combinations thereof can be.

In one example, said R⁶ And R⁷ Are each independently, hydrogen, deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted phenyl or substituted or nonsubstituted bi-substituted triphenyl actuator disclosed.

In addition, compounds represented by said formula 3 can be represented as one formula 3 - 1 to 3 - 4.

[Formula 3 - 1]

[Formula 3 - 2]

[Formula 3 - 3]

[Formula 3 - 4]

In said formula 3 - 1 to 3 - 4, Ar¹ And Ar² , R¹ To R⁷ , ET, and aforementioned L efined.

In addition, compounds represented by the following formula 4 - 1 to 4 - 4 can be represented by said formula 4.

[Formula 4 - 1]

[Formula 4 - 2]

[Formula 4 - 3]

[Formula 4 - 4]

In said formula 4 - 1 to 4 - 4, Ar¹ And Ar² , R¹ To R⁷ , ET, and aforementioned L efined.

In one example, said ET is represented by the formula 5 can be.

[Formula 5]

In said formula 5,

Z¹ To Z⁹ Are each independently N or CR^a And,

Z¹ To Z⁹ N and at least one of the,

R⁸ To R¹¹ And R^a Are each independently, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a heteroaryl group and a substituted or unsubstituted C3 to C12 or a combination of these,

N1 n2 are each independently 0 or 1 and and,

Neighboring atoms * binding site are disclosed.

In one example, Z of said formula 5¹ To Z³ At least one of the implementation being N.

In one example, Z of said formula 5¹ To Z³ At least two of the implementation being N.

In one example, Z of said formula 5¹ To Z³ N each implementation being.

For example, a substituted or unsubstituted group 1 to said ET is listed in one of the functional groups can be a, limited to are not correct.

[Group 1] (to, both in the heteroatom [group 1] is "N")

In one example, said L is single bond, a substituted or unsubstituted phenylene, substituted or unsubstituted back phenyl [leyn, a [...] substituted or unsubstituted, a substituted or unsubstituted phenyl [leyn quarter, the pen neel the [ley which burns [leyn a substituted or unsubstituted, a substituted or unsubstituted [...], a [...] substituted or unsubstituted, a substituted or unsubstituted lung day [ley neel [leyn, a [...] substituted or unsubstituted, a substituted or unsubstituted do not sprout three neel [leyn, five column [thu neel [leyn process for preparation thereof, substituted or nonsubstituted substituted tri phenyl [ley neel [leyn, fine [...] substituted or unsubstituted, a substituted or unsubstituted [...] cryo, substituted or unsubstituted pyrrole one [leyn, one [leyn imidazole substituted or unsubstituted, a substituted or unsubstituted [...] antagonist activity, neel d [leyn sealed by a substituted or unsubstituted, a substituted or unsubstituted [...] antagonist activity, a neel d [leyn pyrimido substituted or unsubstituted, a substituted or unsubstituted [...] triazoles, substituted or unsubstituted [...] sealed, a [...] substituted or unsubstituted, a substituted or unsubstituted isocyanate [...], substituted or nonsubstituted substituted oxa [...], [...] substituted or unsubstituted triazoles, polybutadiene [...] substituted or unsubstituted, a substituted or unsubstituted oxadiazole one [leyn, or combinations thereof can be.

In one example, said L is single bond, a substituted or unsubstituted phenylene, substituted or unsubstituted back phenyl [leyn, a substituted or unsubstituted or a substituted or substituted or unsubstituted [...][...] implementation being. In one example, said L is single bond, a substituted or unsubstituted phenylene, substituted or unsubstituted or a substituted or unsubstituted phenyl [leyn bi-implementation being [...].

For example, chosen from a group listed in said L is a substituted or unsubstituted 2 but, limited to are not correct.

[Group 2]

* A neighbor atomic binding site are disclosed.

Represented by said formula 1 compounds listed in group 3 as one organic compounds which can be a one, limited to are not correct.

[Group 3] ("N" both in the heteroatom to [group 3] are disclosed.)

5 6 7 8

The aforementioned organic compounds can be applied to organic opto-electronic devices.

The aforementioned organic compounds are organic compounds with at least one above-mentioned above be used alone or 2 or can be used with organic compounds other organic compounds. The aforementioned organic compounds other organic together with a compound when used, can be form of composition applied.

Hereinafter, organic opto-electronic devices according to other embodiments composition for one example is described as follows.

Said composition for in one embodiment the organic opto-electronic devices, including at least one organic compound having the above-described organic compounds and carbazole moiety sprayable compositions disclosed.

In hereinafter, the aforementioned organic compounds' number 1 organic compounds' and referred to, carbazole moiety having at least one organic compound is' number 2 organic compounds' is combined with a load.

In one implementation according to said number 2 organic compounds are compounds represented by formula I to be a.

[Formula I]

In said formula I,

Y₁ Is single bond, a substituted or unsubstituted C6 to C30 it will be biting, [leyn, substituted or a substituted or unsubstituted C2 to C30 hetero and it will be biting, [leyn or a combination of these,

Ar₃ A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetero [...] and or a combination of these,

R¹² To R¹⁵ Are each independently a hydrogen, deuterium, a C1 to C20 substituted or unsubstituted alkyl, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 hetero [...] and or a combination of these,

R¹² To R¹⁵ And Ar₃ At least one of the substituted or unsubstituted or a substituted or unsubstituted phenyl [leyn dozing, tree cover without using a tool.

Example number 2 organic compound represented by said formula I, I-a 3 to formula I-a 1 to representation at least one can be.

[Formula I-a 1]

[Formula I-a 2]

[Formula I-a 3]

In said formula I-a 1 to I-a 3,

Y₁ , Y₄ And Y₅ Are each independently single bond, a substituted or unsubstituted C6 to C30 it will be biting, [leyn, substituted or a substituted or unsubstituted C2 to C30 hetero and it will be biting, [leyn or a combination of these,

Ar₃ And Ar₆ Or a substituted or unsubstituted C6 to C30 aryl group each independently, a substituted or unsubstituted C2 to C30 hetero [...] and or a combination of these,

R¹² To R¹⁵ And R is²⁰ To R³¹ theAre independently hydrogen, deuterium, a C1 to C20 substituted or unsubstituted alkyl, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 hetero [...] and or a combination of these,

M is an integer of 0 to 4 one are disclosed.

For example, to I-a 3 Ar of said formula I-a 1₃ And Ar₆ Are each independently, a substituted or unsubstituted phenyl, substituted or unsubstituted back phenyl, a substituted or unsubstituted [...], substituted or nonsubstituted substituted me [phu, a [...] substituted or unsubstituted, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzo [...], benzo [...] substituted or unsubstituted, a substituted or unsubstituted five [ley neel and process for preparation thereof, substituted or nonsubstituted substituted dibenzo furan diary, a substituted or unsubstituted dibenzothiophene diary, substituted or unsubstituted [...] sealed, can be or a combination of these.

Said formula I compounds represented by the following organic compound that is listed in group I can be a number 2, limited to are not correct.

[Group I]

In addition, in one embodiment according to said number 2 organic compounds represented by the following formula II to formula III compound combination moieties to an aromatic moiety can be represented.

[Formula II] [Formula III]

In said formula II and III,

Y₂ And Y₃ Are each independently single bond, a substituted or unsubstituted C6 to C30 it will be biting, [leyn, it will be biting, [leyn a C2 to C30 substituted or unsubstituted heterocyclic, or combinations thereof and,

Ar₄ And Ar₅ Or a substituted or unsubstituted C6 to C30 aryl group each independently, a substituted or unsubstituted C2 to C30 hetero [...], and or a combination of these,

R¹⁶ To R¹⁹ Are each independently a hydrogen, deuterium, a C1 to C20 substituted or unsubstituted alkyl, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 hetero [...] and or a combination of these,

Said formula II includes two adjacent two said formula III ** by being coupled fused ring is formed, said formula II * are each independently CR not fused in a forms a ring^b And,

R^b Is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 hetero [...], or combinations thereof are disclosed.

In one example, said Ar₄ And Ar₅ Are each independently, a substituted or unsubstituted phenyl, substituted or unsubstituted back phenyl, a substituted or unsubstituted [...], or combinations thereof can be.

In one example, said Ar₄ And Ar₅ A cover can be at least one of the substituted or unsubstituted dozing,.

Said formula II an aromatic moiety represented by said formula III represented moieties consisting of a combination number 2 organic compounds according to formula IV-a 1 binding site can be represented either as one IV-a 5.

[Formula IV-a 1] [Formula IV-a 2]

[Formula IV-a 3] [Formula IV-a 4]

[Formula IV-a 5]

In said formula IV-a 1 to IV-a 5,

Y₂ And Y₃ Are each independently single bond, a substituted or unsubstituted C6 to C30 it will be biting, [leyn, substituted or a substituted or unsubstituted C2 to C30 hetero and it will be biting, [leyn or a combination of these,

Ar₄ And Ar₅ Or a substituted or unsubstituted C6 to C30 aryl group each independently, a substituted or unsubstituted C2 to C30 hetero [...] and or a combination of these,

R¹⁶ To R¹⁹ Are each independently a hydrogen, deuterium, a C1 to C20 substituted or unsubstituted alkyl, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 hetero [...] or combinations thereof are disclosed.

In one example, IV-a 5 Ar of said formula IV-a 1 to₄ And Ar₅ Characteristics and at least one of the hole may be a substituent, for example, a cover can be a substituted or unsubstituted dozing,. Said formula II an aromatic moiety represented by said formula III represented moieties listed as one group consisting of a combination number 2 organic compounds are compounds II can be a, limited to are not correct.

[Group II] (for [group II] a compounds or combinations of these embodiments, the heteroatom "N" both are disclosed.)

Said formula I compounds represented by said formula II and said number 2 organic compounds represented by said formula III compounds consisting of a combination comprising at least one aromatic moiety represented moieties can.

In the embodiment of the present invention various combinations of said number 1 organic compounds and said number 2 is one organic compound can be prepared by the mouldable composition.

In the embodiment according to one composition comprises an organic opto-electronic devices can be a dye, such as an organic optoelectronic element can be a dye, said number 1 organic compounds and organic compounds can act as host (host) said number 2. The, relatively strong electrical characteristic is said number 1 organic compounds are compounds having bipolar characteristics may be said number 2 organic compound hole properties relatively strong compound bipolar properties, be used with other organic compounds and said number 1 by increasing light emitting electron charge mobility and stability to further refine the capable of.

In one example, one in the embodiment according to said formula 2 - 3 composition, formula 3 - 3, at least one of organic compounds represented by the following formula 4 - 3 or host including a number 1 number 1, number 2 organic compound represented by said formula I-a 1 or formula IV-a 3 as a host can be at least one of number 2.

A light emitting layer material biased in one electron or hole properties by first introducing the electron or hole while exciton recombination occurs at the interface acts as an electron carrier case is equal to [...] formation occurs. As a result in the emissive layer molecules produced and transport layer interface charge interaction with the roll - off (roll-a off) is more than the movement of the so in a more efficient life characteristics in addition the movement of the to be coated. In order to solve such a host compound number 1 and number 2 door number by introducing organic compounds serve as both a light emitting layer and the other side thereof in the emissive layer to electronic or hole carrier balance transformed light emission region by interpolating element capable of remarkable improvement in the number of small roll - off and life characteristics in addition.

Said organic opto-electronic devices about 1:10 to 10:1 weight ratio composition for said number 1 organic compounds and said number 2 can be an organic compound. For example, 2:8 to 8:2, 7:3 to 3:7, 4:6 to 6:4, and can be in the range of 5:5 comprising, e.g. 7:3, or can be included in the range of 5:5. Included in said range by bipolar characteristics can be effectively implemented efficiency and life improvement.

Said composition in addition to the aforementioned number 1 number 2 organic compounds and organic compound 1 can be at least one organic compound.

Said composition further includes a dopant can be. Said dopant red, green or blue dopant may be, for example, be a phosphorescent dopant.

Said dopant said number 1 host compound working fluid material mixed precipitation said number 2 host compound, generally triplet state or multiple terms exciting excitation (multiple excitation) of a substance such as a light-emitting metal complexes (metal complex) can be used. Said dopant such as inorganic, organic, can be for the presence or absence of compound, 1 species or 2 comprising at least one can be.

Examples of said phosphorescent dopant Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof including organometallic compound is cited. For example it can be represented by the following formula Z said phosphorescent dopant compounds, limited to are not correct.

[Formula Z]

L₂ MX

In said formula Z, metal and M, L and X are each or different ligands and M and complexes are disclosed.

Example said M Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof may be, said L and X be a bidentate ligand example.

Said composition can be dry film forming method or solution such as chemical vapor deposition process is performed.

Hereinafter, the above-mentioned composition and organic opto-electronic devices or organic compounds are described as follows.

Said organic optoelectronic element has an electric energy and light energy if not specifically defined interaction with each other, such as an organic photoelectric device, organic light-emitting device, organic solar cells and organic photosensitive drum or the like is cited.

Organic optoelectronic device opposing said anode and a cathode, said anode and said cathode positioned between the organic material layer can be at least 1, said organic layer comprising the aforementioned organic compound or the foregoing composition can be.

Here organic light emitting organic opto-electronic devices with reference to a drawing of towed through a browser substrate.

Figure 2 shows a cross-section and 1 06 organic light emitting device according to implementation are also also are disclosed.

With reference to the 1 also, in one implementation according to organic light emitting device (100) facing each other anode (120) and a cathode (110), the positive (120) and a cathode (110) positioned between the organic layer (105) comprises.

Anode (120) hole injection ring so that high work function for example can be made of a conductor, such as metals, metal oxides and/or a conductive polymer can be made. Anode (120) for example nickel, platinum, vanadium, chromium, copper, zinc, flexible or alloys thereof; zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) such as metal oxide; ZnO or SnO Al on₂ A combination of metal oxide such as on Sb; poly (3 - methyl thiophene), poly (3, 4 - (ethylene - 1, 2 - dioxy) thiophene) (polyehtylenedioxythiophene: PEDOT), but as to the conductive polymer such as polypyrrole and preparation, limited to are not correct.

Cathode (110) for smooth electron injection for example conductor can be made of low work function, such as metals, metal oxides and/or a conductive polymer can be made. Cathode (110) for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, is, tin, lead, cesium, barium metal or alloys thereof such as; LiF/Al, LiO₂ /Al, LiF/Ca, LiF/Al and BaF₂ Such as multilayer structure including but material/Ca, limited to are not correct.

Organic layer (105) is layer 2 can be 1 or more, the aforementioned organic compound or the foregoing composition including light emitting layer (130) comprises.

Light emitting layer (130) comprising the aforementioned example the aforementioned organic compound alone may be organic compounds including at least two of the aforementioned coating composition type mixing may be disapproval.

The reference 2 also, organic light-emitting device (200) is a light-emitting layer (130) in addition to the hole auxiliary layer (140) results are. Hole auxiliary layer (140) has an anode (120) and a light-emitting layer (130) between the hole injection and/or hole mobility can be blocking and results in electrons. Hole auxiliary layer (140) hole transport layer for example, hole injection layer and/or electron blocking seed layer, can be at least 1 layer.

In addition, in one implementation of the present invention also organic layer 1 or in Figure 2 (105) further as an electron transport layer, with an, hole injection further comprising an organic light emitting device may be disclosed.

Organic light emitting device (100, 200) is formed on the sidewall of the anode or cathode, preferably (evaporation), sputtering (sputtering), plasma plating and ion plating such as dry film forming method or the like after organic layer, cathode or anode thereon number can be formed high pressure liquid coolant.

The aforementioned organic light emitting device can be applied to an organic light emitting device.

In the embodiment of the present invention hereinafter are etched in the specific number. But, for the present invention are described in the embodiment to explain the example specifically or to which only, since the present invention is number one other WD immediately after being turned off.

(Synthesis of compound organic number 1)

Synthesis example 1: Synthesis of compound 41

Number 1 step: Synthesis of intermediates a-a 2

[Compound 1]

5L cap starting materials a-a 1, 36. 4 G (0. 098 Mol), 2, 5 - dichloro - 1 - nitro benzene 22. 7 G (0. 118 Mol), potassium carbonate 27. 2 G (0. 197 Mol) tetrakis (triphenyl phosphine) palladium (0) 5. 69 G (0. 005 Mol) 1, 4 - dioxan a 400 ml, 100 ml water to be driven with a repulsion, 16 hours was heated under nitrogen stream 90 °C. A number after the reaction solvent alone, dichloro methane to by silica gel/filtering which is excellent in 2000, a stand-alone number after chemical microreactor organic solvent, methanol is recrystallised intermediates a-a 2 to a yellow solid (24 g, 61% yield) was obtained.

C₂₄ H₁₅ ClN₂ O₂ : C, 72. 27; H, 3. 79; Cl, 8. 89; N, 7. 02; O, 8. 02; Found: C, 72. 25; H, 3. 77; Cl, 8. 90; N, 7. 00; O, 8. 03

Step number 2: Synthesis of intermediates a-a 3

[Compound 2]

500 Ml cap to intermediates a-a 2 (23. 9 G, 0. 06 Mol), triphenyl phosphine(78. 6 G, 0. 3 Mol) 230 ml dichloro benzene and time-gate 160 °C 12 into a nitrogen substitution with agitation. After reaction, a stand-alone number column chromatography solvent to a positive number (Hexane) as well as intermediates a-a 3 of a yellow solid (17. 7 G, 80% yield) was obtained.

C₂₄ H₁₅ ClN₂ : C, 78. 58; H, 4. 12; Cl, 9. 66; N, 7. 64; Found: C, 78. 56; H, 4. 14; Cl, 9. 64; N, 7. 63

Step number 3: Synthesis of intermediates a-a 4

[Compound 3]

500 Ml cap to intermediates a-a 3 17. 7 G (48. 17 Mmol), [...] 20. 0 G (96. 33Mmol), sodium t - father [thok side (NaOtBu) 9. 3 G (96. 33 Mmol), Pd (dba)₂ 1. 4 G (2. 4 Mmol), tree t - butyl phosphine (P (tBu)₃ ) 9. 3 G (50% in toluene) was placed in 200 ml xylene under refluxing by heating nitrogen stream 12. After number xylene alone, 200 ml methanol mixture obtained therefrom in terms of fifth after filtering, dichloro methane to by silica gel/filtering which is excellent in 2000, a stand-alone number after chemical microreactor organic solvent, acetone is recrystallised to step 3, a-a 4 compound (15. 0 G, 70% yield) is obtained.

C₃₀ H₁₉ ClN₂ : C, 81. 35; H, 4. 32; Cl, 8. 00; N, 6. 32; Found: C, 81. 33; H, 4. 30; Cl, 8. 02; N, 6. 31

Step number 4 : Synthesis of compound 41

[Compound 4]

On nitrogen environment intermediates in the a-a 4 2 a-boronic acid-a 4, 6 a-diphenyl-a 1, 3, 5 a-triazine (23. 3 G, 65. 9 Mmol) after melting a THF 1 L, herein a-a 4 (24. 3 G, 55 mmol) and tetrakis (triphenylphosphine) palladium (0. 88 G, 0. 76 Mmol) with concave chains. Purification of water saturated potassium (potassuim carbonate) (15 g, 110 mmol) in 80 °C 12 with respect to the frame and by heating at reflux. Reaction completion the reaction liquid into the dichloro methane (dichloromethane, DCM) then water extraction of anhydrous MgSO₄ The water to the number after a stand-alone, was cream and filter. The thus obtained residue by flash column chromatography separation positive number said compound 41 (20 g, 51%) are obtained.

C₅₁ H₃₃ N₅ : C, . 85. 57; H, 4. 65; N, 9. 78; Found: C, 85. 55; H, 4. 67; N, 9. 77

Synthesis example 2: Synthesis of compound 1

Number 1 step: Synthesis of intermediates a-a 5

[Compound 5]

Example 1 synthesis of 2, 5 - dichloro - 1 - a-a 1 number 1 in the second intermediates using 2, 4 - dichloro - 1 - nitrobenzene instead made identical intermediate synthesis example 1 except that the human keratinous fibres using the same method a-a 5 component (25. 0 G, yield of 64%) and copiers.

C₂₄ H₁₅ ClN₂ O₂ : C, 72. 27; H, 3. 79; Cl, 8. 89; N, 7. 02; O, 8. 02; Found: C, 72. 25; H, 3. 77; Cl, 8. 91; N, 7. 01; O, 8. 04

Step number 2: Synthesis of intermediates a-a 6

[Compound 5]

Synthesis example 1 number 2 instead of using intermediates in synthesis example 1 except that a non-2 intermediates a-a 5 a-a 6 component in the same method (15. 0 G, 68% yield) of copiers.

C₂₄ H₁₅ ClN₂ : C, 78. 58; H, 4. 12; Cl, 9. 66; N, 7. 64; Found: C, 78. 57; H, 4. 14; Cl, 9. 64; N, 7. 66

Step number 3: Synthesis of intermediates a-a 7

[Compound 7]

Synthesis example 1 of number 3 except that instead of using a non-3 intermediates in synthesis intermediates a-a 6 the same method example 1 component in an a-a 7 (15. 0 G, 70% yield) of copiers.

C₃₀ H₁₉ ClN₂ : C, 81. 35; H, 4. 32; Cl, 8. 00; N, 6. 32; Found: C, 81. 33; H, 4. 33; Cl, 8. 01; N, 6. 30

Step number 4: Synthesis of compound 1

[Compound 8]

Example 1 synthesis of intermediates in a-a 4 number 4 is used instead of intermediates a-a 7 2 a-boronic acid-a 4, 6 a-diphenyl-a 1, 3, 5 a-triazine instead of 2, 4 a-diphenyl-a 6 - (4, 4, 5, 5 a-tetramethyl-a 1, 3, 2 a-dioxaborolan provided 2 a-yl) - 1, 3, 5 a-triazine synthesis example 1 using the same method except that the component 1 (21. 0 G, yield of 60%) for copiers.

C₅₁ H₃₃ N₅ : C, . 84. 48; H, 4. 57; N, 10. 95; Found: C, 84. 45; H, 4. 55; N, 10. 99

Synthesis example 3: Synthesis of compound 9

[Compound 9]

Synthesis example 1 number 4 of intermediates in synthesis example 1 except that instead of using a non-4 intermediates a-a 7 9 component in the same method (22. 0 G, 56% yield) and copiers.

C₅₁ H₃₃ N₅ : C, 85. 57; H, 4. 65; N, 9. 78; Found: C, 85. 56; H, 4. 66; N, 9. 79

Synthesis example 4: Synthesis of compound 73

Number 1 step: Synthesis of intermediates a-a 8

[Compound 10]

Synthesis example 1 is the same as the use of intermediates in a-a 1 number 1, 2, 5 - dichloro - 1 - 2, 3 - dichloro - 1 - nitrobenzene instead of intermediates for dyeing human keratinous fibres using the same method except that the synthesis example 1 component in an a-a 8 (20. 0 G, 51% yield) of copiers.

C₂₄ H₁₅ ClN₂ O₂ : C, 72. 27; H, 3. 79; Cl, 8. 89; N, 7. 02; O, 8. 02; Found: C, 72. 25; H, 3. 78; Cl, 8. 90; N, 7. 01; O, 8. 03

Step number 2: Synthesis of intermediates a-a 9

[Compound 11]

Synthesis example number 2 instead of 1 in a-a 2 intermediates using the same method except that the synthesis intermediates a-a 8 example 1 component in an a-a 9 (12. 0 G, 55% yield) of copiers.

C₂₄ H₁₅ ClN₂ : C, 78. 58; H, 4. 12; Cl, 9. 66; N, 7. 64; Found: C, 78. 57; H, 4. 14; Cl, 9. 65; N, 7. 66

Step number 3: Intermediates a-a 10 synthesis of compound

[Compound 12]

Synthesis example 1 of number 3 except that instead of using a non-3 intermediates in synthesis intermediates a-a 9 the same method example 1 component in an a-a 10 (10. 0 G, 47% yield) of copiers.

C₃₀ H₁₉ ClN₂ : C, 81. 35; H, 4. 32; Cl, 8. 00; N, 6. 32; Found: C, 81. 37; H, 4. 33; Cl, 8. 01; N, 6. 30

Step number 4: Synthesis of compound 73

[Reactive 13]

Synthesis example 1 number 4 of intermediates in synthesis example 1 except that instead of using a non-4 intermediates a-a 10 73 component in the same method (23. 0 G, 56% yield) of copiers.

C₅₁ H₃₃ N₅ : C, 85. 57; H, 4. 65; N, 9. 78; Found: C, 85. 55; H, 4. 64; N, 9. 80

Evaluation 1

Synthesis example 1 to 4 obtained in compound (IBA power 6) GATA supercomputer energy level of CBP compound and DOW provided 28 using Gaussian 09 method was calculated.

The result table 1 such as disclosed.

With reference to the table 1, relatively low LUMO energy level 1 to 4 obtained in synthetic example compounds having can be confirmed. Speaker-light emitting layer of organic light-emitting compound obtained in example 1 to 4 when it is applied to electron transfer can be easily predicted, the first and second said low driving voltage, high luminous efficiency and good life characteristics can be predicted.

In addition, synthetic example 1 to 4 according to compounds are triplet energy level (T₁ ) Leads to a phosphorescent light-emitting layer or a phosphorescent organic hole transporting material host may have properties suitable for use in electroluminescent devices.

While, in the case of CBP to relatively too high LUMO energy level of compounds and DOW provided 28 fixed driving voltage becoming a electron transfer, T₁ Organic small low are expected.

(Number of organic light-emitting small: Light emitting layer Element 1)

In the embodiment 1

9 Compound obtained in synthetic example 3 to an host, with a dopant tris (2 - biphenyl pyridine) iridium (III) [Ir (ph provided ppy)₃ ] Using small organic light emitting-gate number.

(Indium tin oxide) to a thickness of 1500 Å ITO positive deflection, as well as a pack and aluminum (Al) has a thickness of 1200 Å. Specifically, distilled water ultrasonic washing with the ITO coated glass substrate was made thinner. The method for cleaning the distilled isopropyl alcohol, acetone, methanol and dried after plasma cleaner to convey a number of ultrasonic washing for oxygen plasma cleaning said substrate after 10 minutes then using vacuum deposition substrate into his.

The ITO transparent electrode ITO substrate prepared using positive hole injection layer is formed by vacuum deposition of compound A 700 Å thickness on said injection layer has a thickness of 50 Å deposited B compound a, compound C 1020 Å by depositing a thickness of a chemical formula weight percent. Hole transporting layer 3 by combining said compound obtained in example 9 to an host, phosphorescent dopant tris (2 - biphenyl pyridine) iridium (III) [Ir (ph provided ppy)₃ ] 7 Wt % weight percent of a luminescent layer doped with a vacuum deposition a 400 Å thickness.

Then 1:1 ratio on said light emitting layer is simultaneously transporting bed thickness 300 Å by vacuum deposition of compound D Liq weight percent. Alkali metal-containing fullerene said top-gate organic light emitting element and a negative vacuum deposition Al 1200 Å Liq 15 Å sequentially smaller number.

Said 5 layer organic thin film layer structure of ITO/organic light emitting compound A (700 Å)/compound B (50 Å)/compound C (1020 Å)/EML [compound 9: Ir (ph provided ppy) 3 (7 wt %) (400 Å)/compound D: Liq (300 Å)/Liq (15 Å)/Al-gate structure of small number (1200 Å).

Compound A: N4, N4 '- diphenyl-a N4, N4' - bis (9 a-phenyl-a 9H-a carbazol provided 3 a-yl) biphenyl-a 4, 4' - diamine

Compound B: 1, 4, 5, 8, 9, 11 provided hexaazatriphenylene provided hexacarbonitrile (HAT provided CN),

Compound C: N - (biphenyl-a 4 a-yl) - 9, 9 a-dimethyl-a N - (4 - (9 a-phenyl-a 9H-a carbazol provided 3 a-yl) phenyl) - 9H non-fluoren provided 2 a-amine

Compound D: 8 - (4 - (4, 6 a-di (naphthalen-a 2 a-yl) - 1, 3, 5 a-triazin-a 2 a-yl) phenyl) quinoline

In the embodiment 2

Synthesis example 3 synthesis example 9 1 41 instead compounds of a number in the range of 0.1 in the embodiment 1 and the same method [...] compounds of the organic light-emitting element number was high pressure liquid coolant.

In the embodiment 3

Synthesis example 3 synthesis example 9 4 73 instead compounds of compounds of the same method in the embodiment 1 and a number in the range of 0.1 [...] organic light-emitting element number was high pressure liquid coolant.

Comparison example 1

Synthesis example 9 a number in the range of 0.1 in the embodiment 1 and 3 instead of CBP compounds of the organic light-emitting element number [...] same method was high pressure liquid coolant.

Evaluation 2

1 According to example 3 in the embodiment 1 was assessed electron transfer compared to organic light emitting element. Particularly useful as is a measurement method, the result is 2 to table such as disclosed.

(1) Measuring the voltage of driving

In the embodiment 1 to 3, and comparison example 1 organic light-emitting device prepared by the number according to, voltage from 0V - 10V (Keithley 2400) to digital current plasma display panel using the same luminance (750 cd/m² ) Measuring an voltage at are obtained.

(2) Voltage change according to the current density

Number prepared by the organic light emitting elements, voltage from 0V - 10V to digital auto (Keithley 2400) to the current using the current flowing through the electrodes is measured, the measured current value area is formed between the result obtained.

(3) Voltage according to luminance change measurement

Number prepared by the organic light emitting elements, raised up from 0V voltage 10V (Minolta Cs provided 1000A) is formed with a tube-based measurement when ports are obtained.

(4) Light emitting efficiency measuring

Said (1) and (2) measured from luminance with unamended current density and voltage equal current density (10 mA/cm2) of current efficiency (cd/A) was calculated.

(5) Estimating the characteristic life

Number prepared by the organic light emitting elements, luminance (cd/m² ) A 6000 cd/m² By keeping the current efficiency was assessed by measuring (cd/A) 97% is achieved.

(6) External quantum efficiency (EQE) measurement

Number prepared by the organic light emitting elements, when the evaluating sealing with all the elements in the resulting number, using IPCE measurement system were measured.

the reference table 2, organic light-emitting device in the embodiment 1 to 3 according to comparison example 1 according to organic light-emitting device as well as good as compared to lower drive voltages having a luminescent, life characteristics is improved can be confirmed.

In addition, in the embodiment 1 to 3 according to external of organic light-emitting quantum efficiency (External Quantum Efficiency, EQE) evaluation result, about 19% or more can confirm receipt of external quantum efficiency.

(Synthesis of compound organic number 2)

Synthesis example 5: Synthesis of compound E provided 84

Step number 1: synthesis of intermediates C-a 1

[Compound 14]

5L cap to 4 - bromo - 9H - carbazole 200 intermediates. 0 G (0. 8 Mol), eye coordinate of the benzene 248. 7 G (1. 2 Mol), potassium carbonate 168. 5 G (1. 2 Mol), copper iodide (I) 31. 0 G (0. 2 Mol), 1, 10 - phenanthroline 29. 3 G (0. 2 Mol) a N, N - methyl-formaldehyde amide 2. 5 L to be driven with a repulsion, in refluxing nitrogen airflow was 24 hours. The resulting mixture is applied to the fifth crystallized 4 L distilled water therefrom after filtering, water and methanol, hexane wash me. Dichloro methane obtained solid with water using an organic layer obtained by extraction and concentrated sulfuric acid from magnesium number water by a stand-alone, as well as intermediates C-a 1 positive number column chromatography a white solid (216. 2 G, 83% yield) was obtained.

C₂₇ H₁₈ ClN₃ : C, 67. 10; H, 3. 75; Br, 24. 80; N, 4. 35; Found: C C, 67. 12; H, 3. 77; Br, 24. 78; N, 4. 33

Step number 2: synthesis of intermediates C-a 2

[Compound 15]

5 L cap to intermediates C-a 1 (216. 0 G, 0. 7 Mol), 4, 4, 4 ', 4', 5, 5, 5 ', 5' - preparation of methyl - 2, 2' - bi (1, 3, 2 - die [...] (212. 8 G, 0. 8 Mol), potassium acetate (KOAc, 197. 4 G, 2. 0 Mol) and 1, 1' - bis (die [...]) - ferrocene palladium (II) Die chloride (21. 9 G, 0. 03 Mol), tree gap claw [heyk thread gun spin (45. 1 G, 0. 2 Mol) a N, N - methyl amide 3 L after placed in formaldehyde, in stirring time-gate 130 °C 12. After completion of the reaction, a reaction solution obtained by extracting an organic layer from water and EA magnesium sulfate and concentrated number water by using a stand-alone, as well as intermediates C-a 2 positive number column chromatography a white solid (205. 5 G, 83% yield) was obtained.

C₂₆ H₂₅ BN₂ O₂ : C, 78. 06; H, 6. 55; B, 2. 93; N, 3. 79; O, 8. 67; Found: C, 78. 08; H, 6. 57; B, 2. 91; N, 3. 77; O, 8. 67

Step number 3 : Synthesis of intermediates C provided 3

[Compound 16]

5 L cap to intermediates C-a 2 150. 0 G (0. 4 Mol), 1 - bromo - 2 - nitro benzene intermediates 164. 1 G (0. 8 Mol), potassium carbonate 278. 1 G (2. 01 Mol) tetrakis (triphenyl phosphine) palladium (0) 23. 5 G (0. 02 Mol) 1, 4 - dioxan a 2 L, 1 L water to be driven with a repulsion, 16 hours was heated under nitrogen stream 90 °C. A number after the reaction solvent alone, dichloro methane to by silica gel/filtering which is excellent in 2000, a stand-alone number after chemical microreactor organic solvent, methanol is recrystallised intermediates C-a 3 to a yellow solid (86. 3 G, 58% yield) was obtained.

C₁₈ H₁₂ N₂ O₂ : C, 79. 11; H, 4. 43; N, 7. 69; O, 8. 78; Found: C, 79. 13; H, 4. 45; N, 7. 67; O, 8. 76

Step number 4: Synthesis of intermediates C

[Reactive 17]

C-a 2 1000 ml cap to intermediates (86. 0 G, 0. 23 Mol), triphenyl phosphine(309. 5 G, 1. 18 Mol) placed in a 600 ml dichloro benzene nitrogen substitution-gate 160 °C and 12 hours with agitation. After reaction, a stand-alone number column chromatography solvent to a positive number as well as intermediates C (Hexane) of a yellow solid (57. 3 G, 73% yield) was obtained.

C₁₈ H₁₂ N₂ : C, 86. 72; H, 4. 85; N, 8. 43; Found: C, 86. 70; H, 4. 83; N, 8. 47

Number 5 step: Synthesis of compound E provided 84

[Reactive 18]

C 10 500 ml cap to intermediates. 0 G (30. 2 Mmol), 3 - (4 - bromo phenyl) - 9 - phenyl - 9H carbazole 14. 4 G (36. 2 Mmol), sodium t - father [thok side (NaOtBu) 4. 3 G (45. 3 Mmol), Pd (dba)₂ 1. 0 G (1. 8 Mmol), tree t - butyl phosphine (P (tBu)₃ ) 2. 2 G (50% in toluene) in 150 ml xylene 12 by heating at reflux was placed nitrogen airflow. After number xylene alone, 200 ml methanol mixture obtained therefrom in terms of fifth after filtering, dichloro methane to by silica gel/filtering which is excellent in 2000, a stand-alone number after chemical microreactor organic solvent, acetone is recrystallised compound E-a 84 (15. 0 G, yield of 77%) obtained a.

C₄₇ H₃ 0N₄ S: C, 88. 72; H, 4. 81; N, 6. 47; Found: C, 88. 74; H, 4. 82; N, 6. 44

(Number of organic light-emitting small: Light emitting layer Element 2)

In the embodiment 4

ITO (Indium tin oxide) glass substrate coated with a thin film coating thickness of 1500 Å was ultrasonic washing with the distilled water. The method for cleaning the distilled isopropyl alcohol, acetone, methanol and dried after plasma cleaner to convey a number of ultrasonic washing for oxygen plasma cleaning said substrate after 10 minutes then using vacuum deposition substrate into his.

The ITO transparent electrode ITO substrate prepared using positive hole injection layer is formed by vacuum deposition of compound A 700 Å thickness on said injection layer has a thickness of 50 Å deposited B compound a, compound C 1020 Å hole transporting layer has a thickness of a deposited weight percent.

Said hole transporting layer 3 by combining compounds of example 9 and number 2 host compound compounds simultaneously using host B provided 111 dopant tris (2 - biphenyl pyridine) iridium (III) [Ir (ph provided ppy)₃ ] 7 Wt % weight percent of a luminescent layer doped with a vacuum deposition a 400 Å thickness. The compound 9 has been used as the weight ratio 5:5 to compound B provided 111, in the case of separately to have discovered a ratio in the embodiment.

Then 1:1 ratio on said light emitting layer is 300 Å thickness by vacuum deposition of compound D Liq simultaneously transporting bed Al 1200 Å is formed on said metal-containing fullerene Liq 15 Å and sequentially vacuum deposition by forming organic light emitting small cathode-gate number.

Said first and second organic thin film layer consisting of a 5 layer having such a structure, specifically as follows.

ITO/compound A (700 Å)/compound B (50 Å)/compound C (1020 Å)/EML [compound 9: compound B provided 111: Ir (ph provided ppy) 3=46. 5 Wt %: 46. 5 Wt %: 7 wt %] (400 Å)/compound D: Liq (300 Å)/Liq (15 Å)/Al-gate structure of small number (1200 Å).

Compound A: N4, N4 '- diphenyl-a N4, N4' - bis (9 a-phenyl-a 9H-a carbazol provided 3 a-yl) biphenyl-a 4, 4' - diamine

Compound B: 1, 4, 5, 8, 9, 11 provided hexaazatriphenylene provided hexacarbonitrile (HAT provided CN),

Compound C: N - (biphenyl-a 4 a-yl) - 9, 9 a-dimethyl-a N - (4 - (9 a-phenyl-a 9H-a carbazol provided 3 a-yl) phenyl) - 9H non-fluoren provided 2 a-amine

Compound D: 8 - (4 - (4, 6 a-di (naphthalen-a 2 a-yl) - 1, 3, 5 a-triazin-a 2 a-yl) phenyl) quinoline

In the embodiment 5

Compound 9 to compound a number in the range of 0.1 in the embodiment 4 in the weight ratio of 7:3 E provided 66 [...] method identical to the organic light-emitting element and a smaller number-gate.

In the embodiment 6

Compound 41 a number in the range of 0.1 in the embodiment 4 in the weight ratio of compound B provided 111 5:5 [...] method identical to the organic light-emitting element and a smaller number-gate.

In the embodiment 7

Compound 41 a 1:1 weight ratio in the range of 0.1 and compound E provided 66 the method identical to the organic light-emitting element in the embodiment 4 number [...] small number-gate.

In the embodiment 8

Compound 73 a number in the range of 0.1 in the embodiment 4 in the weight ratio of the compound B provided 111 5:5 [...] small organic light-emitting element number method identical to the and-gate.

In the embodiment 9

Compound 73 7:3 [...] a number in the range of 0.1 in the embodiment 8 in the weight ratio of the compound E provided 66 and small organic light-emitting element number-gate the same method.

Reference example 1

Compound 9 alone a number in the range of 0.1 [...] method identical to the host organic light-emitting element in the embodiment 4 and small number-gate.

Comparison example 2

Host a number in the range of 0.1 in the embodiment 4 [...] B provided 111 alone and method identical to the small number-gate organic light-emitting element.

Comparison example 3

Host a number in the range of 0.1 and E provided 66 alone [...] method identical to the organic light-emitting element in the embodiment 4 small number-gate.

Evaluation 3

Reference example 1 and comparison example 1 to 3 according to properties of organic light-emitting on in the embodiment 4 to 9 was assessed. The result is 3 to table such as disclosed.

* 6000 Cd/m brightness² Hereinafter cannot be parts of an element of an

With reference to the table 3, in the embodiment 4 in the embodiment 9 according to the present invention host host light emitting layer using an organic light emitting device of number 1 to number 2 mixing comparison materials either alone using the reference example 1, and comparison example 1 to 3 according to comparison example as compared to organic light-emitting device, driving voltage, efficiency, external quantum efficiency (EQE) equal to or significantly improved life and can be confirmed. In addition, compounds according to the present invention alone than when used with host number 2 of the slop T easy vector capable of life.

The present invention refers to said in the embodiment are different but limited to number tank can be in various forms, in the present invention is technical idea of the present invention is provided to essential features or person with skill in the art without changing other specific embodiment can form can be understand are disclosed. In the embodiment described above the exemplary non-limiting all sides are understood to which must substrate.