COMPOUND AND ORGANIC LIGHT EMITTING DEVICE INCLUDING SAME

Compound according to said one aspect of the present invention is represented by formula 1:

< 화학식 1>

During said formula 1,

Ar₁ to Ar₄ independently from each other of 60 to 6 carbon atoms substituted or a substituted aryl, 1 to 60 carbon atoms of a substituted or unsubstituted aryl heterocycle, substituted or unsubstituted carbon atoms of 6 to 60 exhibits multi aeration condensation, Ar₁ to Ar₄ at least one of the formula I-a exhibiting necessarily a,

< 화학식 1-a>

During 1-a and said formula 1 R₁ to R₅ independently from each other hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl silyl group, a substituted or unsubstituted carbon atoms of 6 to 30 will be biting and it will be recorded , a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms to 6 30 aryl, a substituted or unsubstituted aryl group of 1 to 30 carbon atoms, or a substituted or unsubstituted carbon atoms exhibits multi aeration condensation 30 to 6, * binding sites exhibits.

Contained in the present invention according to said formula 1 formula 1a and the silicon atoms fused ring compound as σ orbital and carbon atoms of the silicon atoms of π orbital superposition of output and input electrons through oxygens of is increased and the, chamber chemical structure formula 1a is 1 are bonded to nitrogen atoms on the center of fine structure molecular the [...] π electronic to more efficiently oxygens is calculation of the internal supply voltage is formed. Furthermore, said through the silicon atoms of a σ-π to the overlay molecules increases and a transition dipole moment causes an increase in the coefficient of absorption molecules is, the increased coefficient of absorbing such atm the biotransformation production of molecules having said formula 1 eventually the long holes for other compounds including publicly known other pyrene derivatives with improved luminous efficiency than may indicate. Therefore, compound of formula 1 according one implementation of the present invention organic light-emitting device and to more applied dopant light-emitting layer can cause characteristics of high efficiency.

Formula 2 refers to in particular removed from structure of excellent not connected to an external substrate may yield an efficiency lies in the potentiating effect exerted. Such compounds, according to some exemplary embodiments of the present invention organic light-emitting device using a, with high efficiency and low drive voltage and a long life can take the characterized.

Said formula 1 to substituents of the described more specifically.

Of the present invention according to an exemplary embodiment, Ar₁ to Ar₄ formula 1-a independently from each other, or a formula 2a to 2c coils respectively drive the actuator depending on:

Said formula 2a to 2c during, Q₁ the-C (R₃₁) (R₃₂)-, -S or-O-and; Z₁, R₃₁ and R₃₂, independently one of the other are, hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 20 alkyl, a substituted or unsubstituted carbon atoms to 6 20 aryl, a substituted or unsubstituted aryl of 1 to 20 carbon atoms, a substituted or unsubstituted 6 to 20 carbon atoms, as condensation multi aeration , -SiR₄₁ R₄₂ R₄₃, to halogen, cyano group, nitro, carboxyl or hydroxy group and;

R₄₁, R₄₂ and R₄₃, independently one of the other are, a substituted or unsubstituted carbon atoms 1 to 20 alkyl, or a substituted or unsubstituted carbon atoms 2are of 6 to 20;

P being integers, of the 1 to 7 ;* combined exhibits sites.

According to an exemplary embodiment of the present invention another, R₁ to R₅ independently from each other hydrogen, deuterium, methyl, isopropenyl-writing, -SiR₄₁ R₄₂ R₄₃, or a coils respectively drive the actuator depending on formula 3a:

Z₁, R₄₁, R₄₂ and R₄₃, independently one of the other are, hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 20 alkyl, a substituted or unsubstituted carbon atoms to 6 20 aryl, a substituted or unsubstituted aryl of 1 to 20 carbon atoms, a substituted or unsubstituted carbon atoms multi aeration condensation 6 to 20, to halogen, cyano group, nitro, carboxyl or hydroxy group and;

P being integers, of the 1 to 5 ;* combined exhibits sites.

Hereinafter, the present specification, at substituted used in representative be represented a longitude and equal (substituents defined a carbon the number, but not limited to, an it displaced as type limit the do not, the present specification in do not define the be represented according to a general.).

Of 1 to 60 carbon atoms, as unsubstituted a linear alkyl may be branched and, is for example, but not limited to methyl, ethyl, profile, isobutyl, sec-butyl, neopentyl, iso-amyl, cyclohexyl, [...] , octyl, roh or Neel , dodecyl as to the aromatic hydrocarbon and, said at least one deuterium atoms that hydrogen atoms in alkyl, halogen atom, hydroxy, nitro, cyano group, amino group, amino d anger , hydrazine, Phenylhcdrazones, carboxylic, R2, R3, R4 are salts thereof, sulfonamide labor pains or salts thereof, phosphoric acid or salts, of carbon number of 1 to 10 alkyl, 1 to 10 carbon atoms of alkoxy groups, 2 to 10 carbon atoms of alkenyl group, 2 to 10 carbon atoms of to alkynyl, aryl 16 to 6 carbon atoms, 4 to 16 carbon atoms of or a heteroaryl, or [...] can be substituted.

2 to 60 carbon atoms, as unsubstituted [...] of diffusibility of a movable ion unsubstituted said intermediate or next to an end of a mandrel at least one carbon double bonds contains.. One example of ethenyl, propenyl, butenyl such as. These non-substituted alkenyl group hydrogen atoms in at least more than one of said substituted the aforementioned similar when diffusibility of a movable ion. substituent.

Unsubstituted alkynyl of 2 to 60 carbon atoms, as the intermediate diffusibility of a movable ion as defined next to an end of a mandrel or at least one carbon triple bond: the casein solution contains an.. One example of acetylene, propylene, phenylacetylene, [...] , isopropyl acetylene, acetylene-butyl t, such as d phenyl acetylene. These alkynyl from one or more hydrogen atoms substituted the aforementioned similar when diffusibility of a movable ion. substituent.

3 to 60 carbon atoms, as unsubstituted alkyl of the carbon atoms of 3 to 60 mixture by the addition of an initiator alkyl in an annular manner, said cycle at least one alkyl hydrogen atoms in 1 to 60 carbon atoms, as the aforementioned substituted alkyl substituent the same..

1 to 60 carbon atoms-alkoxy groups of unsubstituted diphenylamine OA (wherein, A the provided as a word line unsubstituted carbon atoms, as of 1 to 60 fluoroalkyl silane is) as the group with the structure of, as non-limiting examples, a thereof, methoxy, ethoxy, propoxy, ISO Cyclopropyloxy, butoxy, [...] , as to the aromatic hydrocarbon. These alkoxy groups at least more than one of said foregoing hydrogen atoms in substituent similar when diffusibility of a movable ion..

Unsubstituted 6 to 60 carbon atoms, as at least one ring membered aromatic cycle system meaning including carbonate, when may have 2 or more cyclic, that is fused or conjugated each other, single, and the like may be connected to through. Hydroxyaryl herba is provided to obtain a tobacco term phenyl, naphthyl, do not sprout with three Neel such as aromatic system comprising a. Furthermore, at least one aryl said hydrogen atoms in 1 to 60 carbon atoms, as the aforementioned substituted alkyl substituent the same..

A substituted or unsubstituted carbon atoms of 6 to 60 allyl phenyl examples, 1 to 10 carbon atoms of alkyl phenyl (for example, ethyl phenyl), halo phenyl (for example, o-, phenyl -fluoro p and m, dichloro phenyl), roh phenyl cyano, DC oh Roh phenyl , triple [...] , ITO-glass substrate, halo ITO-glass substrate, travel money phenyl cyano, 1 to 10 carbon atoms of alkyl ITO-glass substrate, of 1 to 10 carbon atoms right and wrong phenyl alkoxy, o-, m-, and p- toe reel , o-, [...] -p and m, mesh trityl, lung stipendiary hour phenyl , (α, α-dimethylbenzene) phenyl, (N, N '-dimethyl) amino phenyl , (N, N' -diphenyl) amino phenyl , [...] , indenyl, [...] , halo [...] (for example, fluoro [...]), 1 to 10 carbon atoms of alkyl [...] (for example, methyl [...]), 8 880000488888 [...] alkoxy of 1 to 10 carbon atoms (for example, [...]), [...] cyano, do not sprout three Neel , [...] , [...] , [...] , [...] phenacy, flue [...] , [...] diary, methyl [...] , [...] , tree [...] , neel respirator, three Neel cleaning, ethyl- three Neel , blood three Neel , [...] perylene, chloro [...] , pen hit phenyl , pen hit three Neel , tetra [...] , hexa phenyl , hexa three Neel , ruby three Neel , four reel film type inductor, tree [...] , [...] , [...] , benzopyran [...] , as to the aromatic hydrocarbon [...].

1 to 60 carbon atoms N membered heterocycle of unsubstituted diphenylamine, O, P or S selected from 1, 2, 3, or 4 includes heteroatoms, when or more cyclic 2, that is fused or conjugated with one another, single, and the like may be connected to through. Of 1 to 60 carbon atoms, as unsubstituted hetero allyl examples, pyrazole diary, imidazole diary, oxazole diary, thiazole diary, triazole diary, tetrazole diary, oxadiazole diary, d Neel pyrido, will be and it will keep pyrido, pyrimido d Neel , neel triazine, diary carbazole, indole diary, [...] , [...] isocyanate, as to the aromatic hydrocarbon be enveloped pen light emitting phosphor. In addition said hetero aryl hydrogen atoms in at least one of the aforementioned 1 to 60 carbon atoms, as the same substituted alkyl substituent..

6 to 60 carbon atoms biting jade time column of unsubstituted diphenylamine-OA₁ represented by as a group, at this time A₁ the aryl group of 6 to 60 carbon atoms. Said as to the aromatic hydrocarbon biting jade time phenoxy examples. During group said one or more hydrogen atoms 1 to 60 carbon atoms, as the aforementioned substituted alkyl substituent the same..

6 to 60 carbon atoms it will be biting and be enveloped it crawls of unsubstituted diphenylamine-SA₁ represented by as a group, at this time A₁ the aryl group of 6 to 60 carbon atoms. Said be biting and be envelopedbe enveloped benzene examples, as to the aromatic hydrocarbon [...]. be biting and be enveloped hydrogen atoms in said at least one 1 to 60 carbon atoms, as the aforementioned substituted alkyl substituent the same..

Of 6 to 60 carbon atoms, as unsubstituted condensation multi aeration column , more aromatic rings and at least one non-aromatic ring fused each other including 2 or more cyclic to hydrogenate the olefinically unsaturated groups in the ring or substituted cyclic structures but having as meant a substituent not, said condensation and are differently oriented overall multi aeration in the confirmation of a fact that is distinguishable formula1 hetero an aryl group or.

Of the specific compounds represented by of the present invention said formula 1, as an example, in wrapping, a, including but compounds, are not limited to.

According to one aspect of the present invention other a first electrode and a second electrode, electrode number 1 ; number 2 electrode; and said number 1 number 2 electrode and two or more elements of Ag, an organic light emitting element as the organic layer, said organic layer which appears as the compound said formula 1.

Said organic layer hole injection layer, hole transport layer, hole injection function and hole transport layers functional layer be used as a solvent for the function (hereinafter, "H-functional layer (H-functional layer)" photolithography), buffer layer, electronic stop layer, light emitting layer, hole inhibiting layer, electron transport layer, electron injection layer and an electron transport function and an electron injection function be used as a solvent for the functional layer (hereinafter, "E-functional layer (E-functional layer)" photolithography) may comprise an at least one.

More particularly said second organic which can be, said fluorescent compound can be used with a dopant. For example, said compounds can be used with a dopant displaying an electrodes.

According to an exemplary embodiment of the present invention, organic said second layer, said to a luminescent layer may include a compounds of formula 2:

< 화학식 2>

During said formula 2, R₁₁ to R₂₆ are each independently hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl silyl group, a substituted or unsubstituted carbon atoms of 6 to 30 will be biting and it will be recorded , a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms to 6 30 aryl, a substituted or unsubstituted aryl group of 1 to 30 carbon atoms, or a substituted or unsubstituted carbon atoms exhibits multi aeration condensation 6 to 30.

According to an exemplary embodiment of the present invention, can be host the compounds of said formula 2.

According to an exemplary embodiment of the present invention, in said formula 2 R₁₁, R₁₃, R₂₁ to R₂₃ are each independently hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 20 alkyl, -SiR₄₁ R₄₂ R₄₃, formula 4a to 4c to or coils respectively drive the actuator depending on:

Said formula 4a to 4c during, Q₂ the-C (R₃₁) (R₃₂)-, -NR₃₃-, -S or-O-and;

Z₁, R₃₁ to R₃₃ and R₄₁ to R₄₃ are each independently, hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 20 alkyl, a substituted or unsubstituted carbon atoms to 6 20 aryl, a substituted or unsubstituted aryl of 1 to 20 carbon atoms, a substituted or unsubstituted multi aeration condensation 6 to 20 carbon atoms, a substituted or unsubstituted carbon atoms 1 to 20 alkyl silyl group, a substituted or unsubstituted carbon atoms of 6 to 20 will be biting and it will be recorded , to halogen, cyano group, nitro, carboxyl or hydroxy group and;

P being integers, of the 1 to 7 ;* combined exhibits sites.

According to an exemplary embodiment of the present invention, in said formula 2 R₁₂, R₁₄ to R₂₀, R₂₄ to R₂₆ are each independently hydrogen, can be or deuterium.

Of the specific compounds represented by of the present invention said formula 2, as an example, in wrapping, a, including but compounds, are not limited to.

According to an exemplary embodiment of the present invention, said electron injection layer is organic light emitting device, electron transport layer, light emitting layer, hole injection layer, hole transport layer, or hole injection and hole transport layers includes functional layers which functions simultaneously, said luminescent layer anthracene compound, biting amine orgin compound or styryl compound; may include a.

Other according to an exemplary embodiment of the present invention, said electron injection layer is organic light emitting device, electron transport layer, light emitting layer, hole injection layer, hole transport layer, or hole injection and hole transport layers includes functional layers which functions simultaneously, said light emitting layer for a red layer, green layer, blue layer is based on a either white layer or may include a polyamic acid ester, said hole injection layer, hole transport layer, or hole injection function and hole transport layers charge generation function layer be used as a solvent for the function may further include any material. While, p-dopant and said charge generation material, said p-a dopant quinone derivatives, metal oxide or cyano group-containing compounds can be.

Yet another according to an exemplary embodiment of the present invention, said organic layer includes electron transport layer, said electron transport layer may include metal complex. Li may tightly it will be a body said metal complexes.

The present specification "organic layer" organic the light emitting elements during number 1 number 2 electrode and two or more elements of Ag, single and/or plurality of layers is, which points to the terms.

Figure 1 shows a also pursuant to one implementation of the present invention a cross-sectional drawing of organic light-emitting device having a. timing outlines. Hereinafter, also 1 pursuant to one implementation of the present invention reference to a of organic light emitting device having improved structure and. off at the first and the second manufacturing method.

Substrate (not shown) at, conventional for a substrate used in an organic light emitting device can be used for, mechanical strength, thermal stability, transparency, surface smoothness, easy-to-clean, and handling water-resistant substrate or transparent on glass, use can be made of, plastic substrate.

Said number 1 number 1 on top electrodes are formed upon a substrate by deposition substance electrode the method or a sputtering method can be formed by providing. it will be a child node electrode when said number 1, hole injection to facilitate high substance electrode number 1 with work material is can be selected. In reflective electrode or said number 1 electrode can be transmission electrodes. Number 1 electrode layer is transparent and highly conductive indium tin oxide (ITO), zinc indium oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO) or the like can be used.. Or, magnesium (mg), aluminum (Al), al-li (Al-Li), calcium (Ca), magnesium-indium (mg-In), magnesium-silver (mg-Ag) of utilizing the novel peptide or the surface, said number 1 formed in reflective electrode electrode may be loaded with.

Said number 1 2 a single or electrode material may have a multi-layer structures or more. For example, said number 1 of ITO/Ag/ITO electrode 3 layer structure but may have, limited to not.

Said number 1 constitution: with organic layer include electrode.

Said organic layer hole injection layer, hole transport layer, buffer layer (not shown), light emitting layer, electron transport layer or electron injection layer, or the like may include a.

Hole injection layer (HIL) the number 1 adjacent to vacuum deposition method, spin-coating, Multicast method, device includes an organic membrane comprising such method lb method can be formed by using a.

By a vacuum deposition method in the case of forming the hole injection layer, hole injection conditions its deposition compounds using the layer where, a hole injecting intended to structure and thermal layer according to the characteristics to accomplish different but, for example, about 100 to about 500 °C deposition temperatures, vacuum about 10^-8 to about 10^-3 torr, deposition rate in a range of about 0.01 to about 100 Å / sec can be selected, limited to not.

Spin-coating by in the case of forming the hole injection layer, a hole coating condition thereof as material implantation layer compounds using the, desired a hole injecting layer but depending on the structure and thermal characteristics hereinafter, about 2000rpm to about 5000rpm coating speed, after coating solvent removal temperature to a heat treatment for about 80 °C to 200 °C can be selected at a temperature range of, limited to not.

Publicly known hole injection layer is a first electrode; a hole injection material can be used for, a first electrode; a hole injection layer is publicly known, for example, N, N '-diphenyl-N, N' -bis-[ 4-(phenyl-m-toll-amino)-phenyl]-biphenyl -4, 4 '-diamine (N, N' -diphenyl-N, N '-bis-[ 4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4, 4' -diamine: DNTPD), phthalocyanine compound such as copper phthalocyanine, m-MTDATA [4, 4 ', 4' '-tris (3-methylphenylphenylamino) triphenylamine], NPB (N, N' -di (1-naphthyl)-N, N '- [...] (N, N' -di (1-naphthyl)-N, N '-diphenylbenzidine)), TDATA, 2-TNATA, Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: polyaniline/use of Saccharomyces cerevisiae the thread benzene alcoholic beverage phone it buys), PEDOT/PSS (Poly (3, 4-ethylenedioxythiophene)/ Poly (4-styrenesulfonate): poly (3, 4-ethylenedioxythiophene) / (4-styrene sulfonate)), (Polyaniline/Camphor sulfonicacid: polyaniline/ the cam ladling alcoholic beverage phone it buys) or PANI/PSS Pani/CSA (Polyaniline)/ Poly (4-styrenesulfonate): polyaniline) / (4-styrene sulfonate)) but fixing, not limited to:

Said hole injection layer and a thickness of from about 100 Å to about 10000 Å, for example, can be about 100 Å to about 1000 Å. Said hole injection layer has a thickness of aforementioned range met, , without substantial rise in drive voltage and to duplicate the level of is satisfactory can cause hole injection characteristics.

Next said hole injection layer vacuum deposition method, spin-coating, Multicast method, lb device includes an organic membrane comprising such method using method capable of forming a hole transport layer (HTL).. By [...] and spindle vacuum deposition method in the case of forming the hole transport layer, the coating condition condition and its deposition compounds using the according to to accomplish different but, generally hole injection layer formation substantially equivalent to that of the can be selected in range of terms.

Hole transport layer is is publicly known hole transporting material, use can be made of,. Is publicly known hole transporting material is, for example, fortified-phenyl N, poly vinyl car it will doze such as carbazole derivatives, N, N '-bis (3-methyl phenyl)-N, N' -diphenyl-[ 1, 1-biphenyl]-4, 4 '-diamine (TPD), TCTA (4, 4' , 4 "-tris (N-thiazolly) triphenyl amine (4, 4 ', 4"-tris (N-carbazolyl) triphenylamine)), NPB (N, N' -di (1-naphthyl)-N, N '- [...] (N, N' -di (1-naphthyl)-N, N '-diphenylbenzidine)) as to the aromatic hydrocarbon but, limited to not.

Said hole transport layer and a thickness of from about 50 Å to about 2000 Å, like, for example, about 100 Å to about 1500 Å can be. Said hole transport layer has a thickness of aforementioned range met, , the driving voltage substantial homogeneous to duplicate the level of is satisfactory can cause hole transportation properties.

Said H-functional (hole transport function be used as a solvent for the functional layer) provided as a word line the hole injection layer material and hole transport layer material is 1 or more material can be included, said H-functional layer and a thickness of from about 100 Å to about 10000 Å, for example, can be about 100 Å to about 1000 Å. Said H-functional layer has a thickness of aforementioned range met, , without substantial rise in drive voltage and and aqueous hole injection to duplicate the level of is satisfactory can cause characteristics.

On the other hand, said hole injection layer, hole transport layer and H-functional at least one layer is based on a a compounds represented by general formula 300 and at least one of compounds represented by general formula 350 may include a:

< 화학식 300>

< 화학식 350>

Said formula 300 and 350 during, Ar₁₁, Ar₁₂, Ar₂₁ and Ar₂₂ each independently a, a substituted or unsubstituted C₅-C₆₀ is 5 arylene groups. Said Ar₁₁, Ar₁₂, Ar₂₁ and Ar₂₂ a description the L₁ detailed. reference to the description.

During said formula 300, each independently a f said e and integer of 0 to 5, or 0, 1 or Wednesday 2. For example, 1 and the e, Wednesday 0 but the f, limited to not.

Said formula 300 and 350 during, R₅₁ to R₅₈, R₆₁ to R₆₉ and R₇₁ and R₇₂ each independently a, hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro, amino group, amino d anger , hydrazine, Phenylhcdrazones, carboxylic, R2, R3, R4 are salt thereof, sulfonamide labor pains or salt thereof, either alone, or phosphoric acid salts, a substituted or unsubstituted C₁-C₆₀ alkyl, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl to, a substituted or unsubstituted C₁-C₆₀ alkoxy groups, a substituted or unsubstituted C₃-C₆₀ group, a cycloalkyl group, an, a substituted or unsubstituted C₅-C₆₀ aryl group, a substituted or unsubstituted C₅-C₆₀biting jade time , or a substituted or unsubstituted C₅-C₆₀ may be biting and be enveloped fixed date. For example, said R₅₁ to R₅₈, R₆₁ to R₆₉ and R₇₁ and R₇₂, independently one of the other are, hydrogen; deuterium ; halogen atom; hydroxyl group; cyano group; nitro ; amino group; amino d anger ; hydrazine ; Phenylhcdrazones; carboxylic, R2, R3, R4 are salt thereof; sulfonamide labor pains or salt thereof; or phosphoric acid salts; C₁-C₁₀ alkyl (for example, methyl, ethyl, writing profile, butyl to, [...] , such as group [...]); C₁-C₁₀ alkoxy groups (for example, so2ch2ch2ox, [...] , width time profile, to butoxide, such as [...]); deuterium, halogen atom, hydroxyl group, cyano group, nitro, amino group, amino d anger , hydrazine, Phenylhcdrazones, carboxylic, R2, R3, R4 are salt thereof, either alone, or phosphoric acid to the salts thereof and to a labor pains or sulfonamide in the salts one or more dopants which substituted C₁-C₁₀ alkyl group and C₁-C₁₀ alkoxy groups; phenyl ; [...] ; [...] ; flue [...] ; fine methylenyl; deuterium, halogen atom, hydroxyl group, cyano group, nitro, amino group, amino d anger , hydrazine, Phenylhcdrazones, carboxylic, R2, R3, R4 are salt thereof, sulfonamide labor pains or salt thereof, either alone, or phosphoric acid salts, C₁-C₁₀ alkyl group and C₁-C₁₀ alkoxy groups one or more substituted phenyl, [...] , [...] , flue [...][...] and fine; can be one, limited to not.

During said formula 300, R₅₉ the, phenyl; [...] ; [...] ; bi phenyl ; [...] pyrido; and deuterium, halogen atom, hydroxyl group, cyano group, nitro, amino group, amino d anger , hydrazine, Phenylhcdrazones, carboxylic, R2, R3, R4 are salt thereof, sulfonamide labor pains or salt thereof, either alone, or phosphoric acid salts, a substituted or unsubstituted C₁-C₂₀ alkyl, and a substituted or unsubstituted C₁-C₂₀ alkoxy groups one or more substituted phenyl, [...] , [...] , bi phenyl and [...] ; can be one.

According to an exemplary embodiment, compound represented by said formula 300 can be described by formula 300A but, not limited to:

< 화학식 300A>

During said formula 300A, R₅₁, R₆₀, R₆₁ and R₅₉ detailed the description a reference a bar that makes described above.

For example, said hole injection layer, hole transport layer and H-functional at least one layer is based on a the compound 301 to 320 can be degraded and include one or more of, not limited to:

Said hole injection layer, hole transport layer and at least one of H-functional layer, provided as a word line a publicly known hole injection material selected, is publicly known hole transporting material and/or hole injection function and hole transport layers in addition to a material having functions simultaneously, film of conductive, a lamp, charge-producing material may further include any.

Said charge-generating substance for example, can be-dopant p. Said p-a dopant quinone derivatives, metal oxide and cyano group-containing compounds can be one, limited to not. For example, said p-dopant for example, but not limited to, tetra (TCNQ) and [...][...] benzo -1, 4-2, 3, 5, 6-tetrafluoro-tetra between Oh Roh (F4-TCNQ) such as quinone derivatives; tungsten oxides a metal oxide, such as and as and molybdenum; and compound 200 such as cyano group-containing compounds and the like, including but, not limited to.

< 화합물 200> <F4-TCNQ>

Said hole injection layer, hole transport layer or said H-functional layer said said charge-generating substance and can further comprise a when, said charge-generating substance the hole injection layer, said hole transport layer or said H-functional layer uniformly in decentralized or (homogeneous), or non-uniformly can be distributed, various modifications..

Said hole injection layer, hole transport layer and said H-functional layer with at least one of between said can be includes elastomer, and the buffer layer. Said buffer second layers the wavelength of the light according to optical resonance distance compensation efficiency may serve to increase the. A first electrode; a hole injection material publicly known said buffer layer, may comprise an hole transporting material. Or, a buffer layer is formed on a lower portion of said buffer layer said hole injection layer, hole transport layer and H-functional layer is equal to one of substances contained in the may include a material.

Furthermore, hole transport layer, H-functional layer or buffer layer vacuum deposition method, spin-coating, Multicast method, such as using lb method such as emitting layer capable of forming a (EML).. Vacuum deposition method emitted by spin-coating and in the case of forming the layer, its deposition according to compounds using the conditions to accomplish different but, formed generally in range of terms upon substantially equivalent to that of the can be selected.

Said luminescent layer may include a compound the present invention according to. For example, the with a dopant displaying an derivative is represented by the following formula 1, the derivative is represented by the following formula 2 can be from. In addition to a fullerene derivative is denoted by chemical said formula 1, 2, a variety of publicly known luminescent layer such that the light-generating substances may be is formed by an, display panel, a display using host and of publicly known is formed long by an extrusion forming. In the case of said dopant, of publicly known fluorescent dopant and publicly known, use can be made of, both the phosphorescent dopant.

For example, publicly known of as host, Alq₃, CBP (4, 4 '-N, N' -dicarboxylic carbozole-biphenyl), (poly (n-vinyl fortified)) PVK, 9, 10-di (naphthalene-2-one) anthracene (ADN), TCTA, TPBI (1, 3, 5-tris (N-phenylbenzimidazoles-2-one) benzene (1, 3, (N-phenylbenzimidazole-2-yl) benzene 5-tris)), TBADN (3-tert-butyl -9, 10-di ([...] -2-one) anthracene), E3, DSA (distyrylarylene), dmCBP (reference formula a), the compound 501 to 509 but fixing, limited to not.

PVK ADN

Or, said as host, represented by formula 401 a anthracene compound, use can be made of, :

< 화학식 401>

During said formula 401 Ar₁₂₂ to Ar₁₂₅ of said formula 400 as detailed Ar₁₁₃ a parameter reference a.

During said formula 401 Ar₁₂₆ and Ar₁₂₇, independently one of the other are, C₁-C₁₀ alkyl (for example, methyl, ethyl or writing) can be.

K and during said formula 401 l, independently one of the other are 0 to 4 may an integer. For example, the 0, 1 or Wednesday 2 l and said k.

For example, represented by said formula 401 anthracene-based compound can be compounds, either, limited to not:

Said organic light emitting device when the full color organic light emitting device, red light emitting layer emitting layer, green light emission layer 24 and a blue light emitting layer. may be patterned.

On the other hand, said red light emitting layer, green emitting layer 24 and a blue light emission at least one of one which is marked as a chemical dopant may comprise an (ppy = phenylpyridine)

For example, using compound the blue dopant as can be degraded and, limited to not.

DPAVBi

TBPe

For example, as red dopant can be degraded and using compound a, limited to not.

For example, using compound the green dopant as can be degraded and, limited to not.

On the other hand, said emitting layer refers to a dopant that can be included as a logical source, the logical source tightly it will be a body , not limited to:

Furthermore, said emitting layer refers to a dopant that can be included as a logical source, the logical source tightly it will be a body -Os, not limited to:

Said when dopant host and a luminescent layer, conventional content of dopant to the host about 100 parts by weight of dispersed in the base, from about 0.01 to about 15 parts by weight can be selected in a range of, limited to not.

Said light-emitting layer and a thickness of from about 100 Å to about 1000 Å, like, for example, about 200 Å to about 600 Å can be. Said light emitting layer has a thickness of aforementioned range met, , the driving voltage substantial homogeneous excellent luminescent properties can exhibit.

Next and a electron transport layer (ETL) for vacuum deposition method, or spin-coating, various such as Multicast method. is formed by an. By spin-coating and vacuum deposition method in the case of forming the electron transport layer, according to condition the compounds using the to accomplish different but, formed generally in range of terms upon substantially equivalent to that of the can be selected.

Said electron transport layer material is an electron injection electrode (Cathode) stably electrons injected from a, and that function to transport of publicly known as ID an electron transport material. Examples of of electron transport materials publicly known, quinoline derivatives, in particular tris (8- [...]) aluminum (Alq3), TAZ, Balq, beryllium bis (benzo [...] -10-octanoate) (beryllium bis (benzoquinolin-10-olate: Bebq₂), ADN, compound 201, 202 with the aid of side materials such as compounds may also be used but, limited to not.

< 화합물 201> < 화합물 202>

BCP

Said electronic transport layer and a thickness of from about 100 Å to about 1000 Å, like, for example, about 150 Å to about 500 Å can be. Said electron transport layer has a thickness of aforementioned range met, , the driving voltage substantial to duplicate the level of is satisfactory homogeneous may yield an electronic transportation properties.

Or, said electron transport layer in addition to publicly known electronic-transporting organic compound, metal-containing material may further include any.

Said metal-containing material is Li may include complex. For example, but not limited to said Li complexes, lithium [...] 203 compound or (LiQ) as to the aromatic hydrocarbon:

< 화합물 203>

In addition a negative upper electron transport layer that facilitate injection of electrons from the they are substances having function of (EIL) electron injection layer is which can be stacked is especially not limit the material.

Said electron injection layer formation material include LiF, NaCl, CsF, Li₂ O, BaO as a material for forming electron injection layer such as any publicly known can be character. Said electron injection layer compounds using the according to the deposition condition to accomplish different but, generally hole injection layer formation substantially equivalent to that of the can be selected in range of terms.

Said electron injection layer and a thickness of from about 1 Å to about 100 Å, can be about 3 Å to about 90 Å. Said electron injection layer has a thickness of aforementioned range met, , the driving voltage substantial homogeneous to duplicate the level of is satisfactory can cause electron injection characteristics.

An organic layer include constitution: number 2, and these are provided with electrodes. An electron injection electrode is a cathode (Cathode) said number 2 electrode which may be, at this time, said number 2 for electrode formation is formed on the metal metal, alloy, electrically conductive compounds and mixtures of these, use can be made of,. Lithium as in set (Li), magnesium (mg), aluminum (Al), al-li (Al-Li), calcium (Ca), magnesium-indium (mg-In), such as magnesium-silver (mg-Ag) formed with a foil can cause transmission electrodes. While, the device which can emit light from the entire ITO, IZO using capable of forming a transmission electrodes such as, various modifications..

Or more, also organic light-emitting device which said 1 but described reference to, limited to not.

Furthermore, emitting layer of a phosphorescent dopant has function triplet exciton or hole resides electron transport layer be a plasma state the, said hole transport layer and a light emitting layer or between H-functional layer and a light emitting layer between being sunken at a lower vacuum deposition method, spin-coating, Multicast method, such as such as lb using method capable of forming a hole inhibiting layer (HBL).. By spin-coating and vacuum deposition method in the case of forming the hole inhibiting layer, according to condition the compounds using the to accomplish different but, generally hole injection layer formation substantially equivalent to that of the can be in range of terms. Hole inhibiting of publicly known can be used for material, examples of is, oxadiazole derivatives or triazole derivatives, phenanthroline derivatives as to the aromatic hydrocarbon. For example, a BCP hole inhibiting layer a, use can be made of, material.

Said hole inhibiting layer and a thickness of from about 20 Å to about 1000 Å, like, for example, about 30 Å to about 300 Å can be. Said hole a thickness of the polishing is aforementioned range met, , the driving voltage substantial hole having excellent homogeneous can cause aparatus.

The present invention along the organic light emitting device with a variety of types of flat panel display device, for example passive matrix organic light emitting display device and active matrix organic light emitting display device can be equipped with.. In particular, active matrix organic light emitting display device when a, on the side with the circuit board with the pixel number 1, a drain electrode on the source electrode of thin film transistor as electrodes electrically may be connected to. Furthermore, a double-sided organic light emitting device in said can be displayed to be. can be equipped with flat panel display device.

In addition of the present invention, according to some exemplary embodiments of the present invention one implementation the aperture organic layer deposited using compound according can be formed with the method or, or solution according one implementation of the present invention produced by a wet coating compound can be formed even method.

In hereinafter, embodiment and positive examples synthesis thereby, the cold air flows example, pursuant to one implementation of the present invention relative to organic light emitting devices but specifically, , and positive examples synthesis of the present invention is embodiment to exemplify limited not.

[In the embodiment]

Representative synthetic example :

Of the present invention formula 1 corresponding to said representative nothing pyrene-diamine in the case of 1, 6-such as type and chemical reaction can be utilizing [...]. 1, 6-of the signals is converted into a hydroxy bromine one [...] palladium after amination by using the catalyst and cyclization where the progress of the reaction the amination through one-time after which the rate through a minimum compound. can be synthesized easily.

Furthermore, an asymmetrical 1, 6-3, 8-substituted [...] when the syngas such as type and reaction having chemical structure can be.

Hereinafter the present invention compounds thereby, the cold air flows in which the synthesis for a portion, of the invention formula 1 using the same capable of synthesizing compounds of structure..

Synthesis example 1: synthesis of compound 1

S-1 synthesis of intermediates

1-bromo-4-chloro-2-nitrobenzene 11.3 g (48.0 mmol), 2-bromo phenyl step theory it buys 8.0 g (40 mmol), Pd (PPh₃)₄ 2.3 g (2.0 mmol) and K₂ CO₃ 16.6 g (120.0 mmol) for THF/H2O (2/1) senses a rotation velocity of the disk to 100 ml mixed solution 80^o C in adaptation stirring time 5. After marked on the specific room temperature a reaction solution are said possible with conventional 60 ml 60 ml water extracted burn 3 to 30 parts by weight of diethyl ether. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating S-1 9.1 g (yield 72%)is obtained. The resulting compound is the LC-MS it is found out that through. C₁₂ H₇ BrClNO₂: M+1 311.8

S-2 synthesis of intermediates

Intermediates S-1 9.0 g (28.8 mmol) senses a rotation velocity of the disk for toluene/EtOH (2/1) 60 ml solution, SnCl₂. 2H₂ O 27.0 g (120.0 mmol) 1N HCl 30 ml of adding slowly solution senses a rotation velocity of the disk to heating at a reflux the 8. Marked on the specific room temperature a reaction solution are said ice water cold after pH 8-9 poured into the 100 ml NaOH aqueous solution is lowered to about 80 ml through tailoring of the extracted burn 3 to 30 parts by weight of diethyl ether. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating S-2 6.6 g (82% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₁₂ H₉ BrClN: M+1 282.0

S-3 synthesis of intermediates

Intermediates S-2 6.2 g (22.0 mmol) and NaNO₂ 3.0 g (22.0 mmol) for 1N HCl/CH₃ CN (10/1) senses a rotation velocity of the disk to 50 ml mixed solution 0^o C in 30 minutes stirring section. Said a reaction solution are KBr 9.5 g (80.0 mmol) for H₂ O 30 ml to 3 senses a rotation velocity of the disk at room temperature, are added to the solution the stirring time. Said reactive solution 10% Na₂ S₂ O₃ 60 ml to 30 ml aqueous solution of 30 parts by weight of diethyl after added at a water extracted burn 3. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating S-3 6.4 g (89% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₁₂ H₇ Br₂ Cl:M+1 344.9

S-4 synthesis of intermediates

Intermediates S-3 6.02 g (17.4 mmol) senses a rotation velocity of the disk to THF 50 ml of -78^o C by a n-BuLi 14.0 ml (2.5M in Hexane) 2 added slowly at a temperature a the stirring time. Said d methyl thread column dichloro solution 2.1 ml (17.4 mmol) is slowly added after 30 minutes stirring and temperature in, 3 time adaptation stirring at room temperature. Said reactive solution 40 ml 40 ml distilled after added at a water extracted burn 3 to 30 parts by weight of diethyl ether. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating S-4 2.6 g (59% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₁₄ H₁₃ ClSi: M+1 245.0

S-5 synthesis of intermediates

Intermediates S-4 2.45 g (10.0 mmol), aniline 1.4 g (15.0 mmol), Pd₂ (dba)₃ 0.18 g (0.2 mmol), P t Bu₃ 0.04 g (0.2 mmol) and NaO t Bu 1.9 g (20.0 mmol) in 85 °C is toluene 30 ml to adaptation stirring time senses a rotation velocity of the disk 4. After marked on the specific reaction solution down to the normal temperature, 30 ml to 30 parts by weight of diethyl ether and a 30 ml water extracted burn 3. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating S-5 2.7 g (91% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₂₀ H₁₉ NSi: M+1 302.1

I-1 synthesis of intermediates

1, 6- [...] 3.6 g (20.0 mmol), CuI 0.38 g (2.0 mmol) and KOH 6.7 g (120.0 mmol) to nitrogen in an atmosphere in Toluene/PEG400/H2O (5/4/1) mixed solution 100 ml is dibutyl phthalate or dimethyl 110^o C adaptation stirring time heated to 8. Marked on the specific down to the normal temperature after said solution, pH 2-3 1N HCl 10 ml by adding 60 ml ethyl acetate after fitted extracted three times. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-1 3.8 g (64% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₁₆ H₉ BrO: M+1 297.0

I-2 synthesis of intermediates

Intermediates I-1 2.97 g (10.0 mmol), intermediates S-5 3.3 g (11.0 mmol), Pd₂ (dba)₃ 0.18 g (0.2 mmol), P t Bu₃ 0.04 g (0.2 mmol) and NaO t Bu 1.9 g (20.0 mmol) in 85 °C is toluene 30 ml to adaptation stirring time senses a rotation velocity of the disk 4. After marked on the specific reaction solution down to the normal temperature, 30 ml to 30 parts by weight of diethyl ether and a 30 ml water extracted burn 3. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-2 4.6 g (89% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₃₆ H₂₇ NOSi: M+1 518.2

I-3 synthesis of intermediates

Intermediates I-2 4.6 g (8.9 mmol) and 1 g (15.0 mmol) pyridine in 20 ml medium of 0 oC senses a rotation velocity of the disk to triflic anhydride 3.0 g (10.7 mmol) is slowly added 2 oligo temperature a high temperature to the normal temperature after adaptation stirring time. Reactive solution 20 ml to 20 ml water added dichloro methane extracted burn 3. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-3 5.4 g (93% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₃₇ H₂₆ NO3SSi: M+1 650.1

Synthesis of compound 1

Intermediates I-3 5.4 g (8.3 mmol), diphenylamine 1.55 g (9.14 mmol), Pd₂ (dba)₃ 0.15 g (0.17 mmol), P t Bu₃ 0.03 g (0.17 mmol) and NaO t Bu 1.2 g (12.5 mmol) in 85 °C is toluene 30 ml to adaptation stirring time senses a rotation velocity of the disk 4. After marked on the specific reaction solution down to the normal temperature, 30 ml to 30 parts by weight of diethyl ether and a 30 ml water extracted burn 3. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by separating the compounds purification 1 4.7 g (84% yield) is obtained. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₄₈ H₃₆ N₂ Si:M+1 669.3

¹ H NMR (400MHz, CDCl₃) δ 7.90-7.87 (m, 2H), 7.77 (d, 1H), 7.65 (d, 1H), 7.57-7.45 (m, 6H), 7.39-7.35 (m, 2H), 7.31-7.27 (m, 1H), 7.17-7.06 (m, 8H), 7.02-6.98 (m, 3H), 6.83-6.78 (m, 6H), 0.4 (s, 6H)

Synthetic example 2: synthesis of compound 54

I-4 synthesis of intermediates

1, 6-7.2 g (20.0 mmol) [...] senses a rotation velocity of the disk to THF 60 ml of -78^o C n-BuLi 48.0 ml (2.5M in Hexane) by a slowly after added -30^o C it peels, elevated temperature by stirring section. 1 process has been completed a reaction solution are again -78^o C by a slowly added iodomethane 7.5 ml 4 in the normal temperature after adaptation stirring time. Said reactive solution 60 ml 60 ml distilled after added at a water extracted burn 3 to 30 parts by weight of diethyl ether. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-4 2.99 g (yield 65%)is obtained. The resulting compound is the LC-MS it is found out that through. C₁₈ H₁₄: M+1 231.1

I-5 synthesis of intermediates

Intermediates I-5 2.9 g (12.6 mmol) of 30 parts by weight of diethyl ether/methanol (2.5/1) mixed solution 30 ml is dibutyl phthalate or dimethyl 0^o C HBr 3.8 ml (33 wt % in AcOH) in slowly added after 30 minutes the stirring. Said reactive solution hydrogrnperoxide 1.73 ml (30 wt % in H₂ O) added slowly at a temperature the same time 8 in the normal temperature after stirring section. After complete reaction after 30 ml 30 ml distilled water added at a water extracted burn 3 to 30 parts by weight of diethyl ether. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-5 3.58 g (yield 92%)is obtained. The resulting compound is the LC-MS it is found out that through. C₁₈ H₁₃ Br:M+1 309.0

I-6 synthesis of intermediates

Intermediates I-5 3.5 g (11.3 mmol) is dibutyl phthalate or dimethyl 30 ml medium of, 0^o C in NaNO₂ 0.85 g (12.4 mmol) senses a rotation velocity of the disk to 10 ml of a trifluoroacetic acid solution slowly added after 30 minutes stirring section. Said reactive solution to terminate the -280 parts by weight of an triethylamine 10 ml, and the produced solid 40 ml distilled water after filtering the added dichloro methane extracted burn 3 to 30 ml. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-6 2.88 g (yield 72%)is obtained. The resulting compound is the LC-MS it is found out that through. C₁₈ H₁₂ BrNO₂: M+1 354.0

I-7 synthesis of intermediates

Intermediates I-6 2.86 g (8.1 mmol), intermediates S-5 2.93 g (9.72 mmol), Pd₂ (dba)₃ 0.15 g (0.17 mmol), P t Bu₃ 0.03 g (0.17 mmol) and NaO t Bu 1.2 g (12.5 mmol) in 85 °C is toluene 30 ml to adaptation stirring time senses a rotation velocity of the disk 4. After marked on the specific reaction solution down to the normal temperature, 30 ml to 30 parts by weight of diethyl ether and a 30 ml water extracted burn 3. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-7 3.4 g (yield 73%)is obtained. The resulting compound is the LC-MS it is found out that through. C₃₈ H₃₀ N₂ O₂ Si:M+1 575.2

I-8 intermediates

Intermediates I-7 3.4 g (5.91 mmol)/ methanol medium of (1/1) mixed solution adding an Pd/C 0.5 g senses a rotation velocity of the disk to 20 ml, reaction vessel 1, hydrogen gas pressure 3 state quasi washing liquid is supplied to the adaptation stirring time. After a complete reaction, a reaction solution are celite was are filtered. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-8 2.96 g (92% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₃₈ H₃₂ N₂ Si:M+1 545.2

I-9 synthesis of intermediates

2.9 g (5.32 mmol) intermediates senses a rotation velocity of the disk to 15 ml acetonitrile for 0^o C 1N HCl 16 ml in added slowly. Temperature in 30 minutes after NaNO₂ 0.92 g (13.3 mmol) 30 minutes is slowly adding further stirring section. KI 8 g (48 mmol) said reactive solution 2 is added to the stirring time. Saturation, a reaction mixture of said NaHCO₃ solution 20 ml after added at a water extracted three times 30 ml ethyl acetate. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-7 2.02 g (58% yield) is obtained. The resulting compound is the LC-MS it is found out that through. C₃₈ H₃₀ INSi: M+1 656.1

Synthesis of compound 54

Intermediates I-9 2.0 g (3.05 mmol), intermediates A-1 1.2 g (3.6 mmol), Pd₂ (dba)₃ 0.05 g (0.06 mmol), P t Bu₃ 0.01 g (0.06 mmol) and NaO t Bu 0.44 g (4.6 mmol) in 85 °C is toluene 20 ml to adaptation stirring time senses a rotation velocity of the disk 4. After marked on the specific reaction solution down to the normal temperature, 20 ml to 30 parts by weight of diethyl ether and a 20 ml water extracted burn 3. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to residue is obtained by separating the compounds purification car gel tube silica 54 2.26 g (yield 86%)is obtained. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₂ H₄₆ N₂ OSi: M+1 863.3

¹ H NMR (400MHz, CDCl₃) δ 8.06-8.00 (m, 2H), 7.87-7.81 (m, 2H), 7.77-7.64 (m, 4H), 7.62-7.55 (m, 5H), 7.51-7.38 (m, 4H), 7.32 (dd, 1H), 7.26-7.20 (m, 2H), 7.19 (d, 1H), 7.12-6.91 (m, 8H), 6.89-6.85 (m, 2H), 6.83 (dt, 1H), 6.78-6.74 (m, 2H), 2.57 (s, 6H), 0.33 (s, 6H)

Synthetic example 3: synthesis of compound 79

I-10 synthesis of intermediates

Intermediates I-4 2.3 g (10.0 mmol) senses a rotation velocity of the disk to 30 ml medium of N-bromo succinimide 4.4 g (25.0 mmol) is slowly added 6 time after stirring section. Reactive solution 30 ml 30 ml distilled water added dichloro methane extracted three times. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by purification intermediate that is separating I-10 2.95 g (yield 76%)is obtained. The resulting compound is the LC-MS it is found out that through. C18H₁₂ Br₂: M+1 386.9

Synthesis of compound 79

Intermediates I-10 2.9 g (12.5 mmol), intermediates S-6 10.3 g (27.5 mmol), Pd₂ (dba)₃ 0.55 g (0.6 mmol), P t Bu₃ 0.12 g (0.6 mmol) and NaO t Bu 3.6 g (37.5 mmol) in 85 °C is toluene 40 ml to adaptation stirring time senses a rotation velocity of the disk 4. After marked on the specific reaction solution down to the normal temperature, 40 ml to 30 parts by weight of diethyl ether and a 40 ml water extracted burn 3. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to residue is obtained by separating car gel tube silica which comprises purifying an compound 79 8.8 g (74% yield) is obtained. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₈ H₅₂ N₂ Si₂: M+1 953.4

¹ H NMR (400MHz, CDCl₃) δ 8.02 (d, 2H), 7.80 (d, 2H), 7.67 (d, 2H), 7.60-7.55 (m, 12H), 7.51-7.42 (m, 4H), 7.34-7.12 (m, 10H), 7.02 (dd, 2H), 6.94-6.90 (m, 4H), 6.84 (d, 2H), 0.30 (s, 12H)

Said intermediates S-5, 54 and compound 1 compound to similar examples of the synthesis of intermediates using which capable of synthesizing compounds of the present invention, some of compounds synthesized to described but these compounds of the present invention not limited to.

Synthesis of compound 6

Compound 1 synthesis and similarly intermediates I-1, intermediates using S-7 the compounds have been synthesised for 6. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₄₈ H₃₁ D₅ N₂ Si:M+1 674.3

¹ H NMR (400MHz, CDCl₃) δ 7.90-7.87 (m, 2H), 7.77 (d, 1H), 7.66 (d, 1H), 7.57-7.45 (m, 6H), 7.39-7.27 (m, 3H), 7.16-7.07 (m, 6H), 7.02-6.98 (m, 2H), 6.89-6.86 (m, 4H), 0.41 (s, 6H)

Synthesis of compound 11

Compound 1 synthesis and similarly intermediates I-1, intermediates of a compound using an A-2 S-5 and intermediates have been synthesised for 11. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₅₇ H₄₄ N₂ Si:M+1 785.3

¹ H NMR (400MHz, CDCl₃) δ 7.89 (d, 2H), 7.79-7.75 (m, 2H), 7.66 (d, 1H), 7.57-7.42 (m, 6H), 7.39-7.27 (m, 5H), 7.19-7.06 (m, 8H), 7.02-6.96 (m, 3H), 6.92 (d, 1H), 6.86-6.82 (m, 4H), 1.61 (s, 6H), 0.40 (s, 6H)

Synthesis of compound 14

Compound 1 synthesis and similarly intermediates I-1, intermediates using A-1 and intermediates S-5 the compounds have been synthesised a 14. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₀ H₄₂ N₂ OSi: M+1 835.3

¹ H NMR (400MHz, CDCl₃) δ 7.95 (d, 1H), 7.90 (d, 1H), 7.83-7.76 (m, 2H), 7.70-7.64 (m, 4H), 7.60-7.35 (m, 13H), 7.31-7.27 (m, 1H), 7.19-7.02 (m, 10H), 6.97-6.93 (m, 1H), 6.85-6.81 (m, 1H), 6.78-6.75 (m, 2H), 0.41 (s, 6H)

Synthesis of compound 16

Compound 1 synthesis and similarly intermediates I-1, intermediates using A-3 and intermediates S-5 the compounds have been synthesised for 16. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₀ H₄₃ FN₂ Si:M+1 839.3

¹ H NMR (400MHz, CDCl₃) δ 7.90-7.84 (m, 2H), 7.77 (d, 1H), 7.69-7.48 (m, 15H), 7.42-7.35 (m, 3H), 7.31-7.27 (m, 2H), 7.19-7.06 (m, 8H), 7.02-6.94 (m, 2H), 6.89-6.82 (m, 4H), 0.42 (s, 6H)

Synthesis of compound 22

Compound 1 synthesis and similarly intermediates I-1, intermediates using S-8 the compounds have been synthesised a 22. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C54H₃₈ N₂ OSi: M+1 759.3

¹ H NMR (400MHz, CDCl₃) δ 7.99 (d, 1H), 7.89-7.76 (m, 3H), 7.72-7.64 (m, 3H), 7.60-7.34 (m, 10H), 7.31-7.28 (m, 1H), 7.18-7.02 (m, 8H), 6.98-6.92 (m, 2H), 6.88-6.82 (m, 4H), 0.41 (s, 6H)

Synthesis of compound 24

Compound 1 synthesis and similarly intermediates I-1, intermediates of a compound using an A-4 S-5 and intermediates have been synthesised a 24. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₆ H₄₅ FN₂ OSi: M+1 929.3

¹ H NMR (400MHz, CDCl₃) δ 7.97 (d, 1H), 7.89 (d, 1H), 7.84-7.76 (m, 3H), 7.72-7.60 (m, 9H), 7.57-7.45 (m, 8H), 7.42-7.18 (m, 8H), 7.11-7.02 (m, 5H), 6.99-6.94 (m, 1H), 6.92-6.88 (m, 1H), 6.83-6.79 (m, 2H), 0.40 (s, 6H),

Synthesis of compound 25

Compound I-6 intermediates similarly synthesis and 54, of a compound using diphenylamine and S-5 intermediates have been synthesised a 25. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₅₀ H₄₀ N₂ Si:M+1 697.3

¹ H NMR (400MHz, CDCl₃) δ 8.01-7.98 (m, 2H), 7.87 (d, 2H), 7.77 (d, 1H), 7.67 (d, 1H), 7.49 (dd, 1H), 7.39-7.27 (m, 2H), 7.19-7.00 (m, 10H), 6.96-6.91 (m, 3H), 6.89-6.80 (m, 6H), 2.57 (s, 6H), 0.40 (s, 6H)

Synthesis of compound 29

Compound 1 synthesis and similarly intermediates I-1, intermediates of a compound using an A-5 S-5 and intermediates have been synthesised a 29. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₅₄ H₃₈ N₂ OSi: M+1 759.3

¹ H NMR (400MHz, CDCl₃) δ 8.01-7.96 (m, 2H), 7.82-7.80 (m, 2H), 7.71-7.55 (m, 8H), 7.52-7.20 (m, 7H), 7.12-6.98 (m, 6H), 6.94 (d, 1H), 6.89-6.84 (m, 2H), 6.80-6.76 (m, 2H), 6.72-6.68 (m, 2H), 0.36 (s, 6H)

Synthesis of compound 31

Compound 1 synthesis and similarly intermediates I-1, intermediates using A-1 and intermediates S-6 the compounds have been synthesised for 31. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₆ H₄₆ N₂ OSi: M+1 911.3

¹ H NMR (400MHz, CDCl₃) δ 8.00 (dd, 1H), 7.95 (d, 1H), 7.83-7.79 (m, 2H), 7.70-7.63 (m, 4H), 7.61-7.53 (m, 10H), 7.51-7.38 (m, 6H), 7.32 (t, 1H), 7.26-7.08 (m, 6H), 7.02-6.92 (m, 5H), 6.89-7.78 (m, 4H), 0.30 (s, 6H)

Synthesis of compound 42

Compound 1 synthesis and similarly intermediates I-1, intermediates using A-6 and intermediates S-5 the compounds have been synthesised a 42. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₃ H₅₁ FN₂ Si₂: M+1 911.4

¹ H NMR (400MHz, CDCl₃) δ 8.01 (d, 1H), 7.86-7.81 (m, 2H), 7.69-7.48 (m, 15H), 7.42-7.30 (m, 7H), 7.26-7.20 (m, 2H), 7.12-7.04 (m, 3H), 7.00 (d, 1H), 6.96-6.86 (m, 3H), 6.62-6.78 (m, 2H), 0.33 (s, 6H), 0.24 (s, 9H)

Synthesis of compound 44

Compound 1 synthesis and similarly intermediates I-1, intermediates using A-7 and intermediates S-9 the compounds have been synthesised a 44. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₅₉ H₄₅ N₃ OSi: M+1 840.3

¹ H NMR (400MHz, CDCl₃) δ 8.02-7.96 (m, 2H), 7.90 (d, 1H), 7.85-7.81 (m, 2H), 7.70-7.55 (m, 8H), 7.53-7.30 (m, 6H), 7.26-7.20 (m, 4H), 7.08-6.98 (m, 2H), 6.96-6.91 (m, 2H), 6.86 (d, 1H), 6.82-6.78 (m, 2H), 1.50 (s, 9H), 0.33 (s, 6H)

Synthesis of compound 59

Compound synthesis and 54 I-6 intermediates similarly, intermediates using A-1 and intermediates S-6 the compounds have been synthesised a 59. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₈ H₅₀ N₂ OSi: M+1 939.4

¹ H NMR (400MHz, CDCl₃) δ 8.07-8.00 (m, 2H), 7.86-7.74 (m, 4H), 7.70-7.64 (m, 2H), 7.62-7.38 (m, 14), 7.34-7.02 (m, 13H), 6.97-6.91 (m, 2H), 6.87-6.83 (m, 1H), 2.57 (s, 6H), 0.30 (s, 6H)

Synthesis of compound 63

Compound 1 synthesis and similarly intermediates I-1, intermediates of a compound using an A-5 S-10 and intermediates have been synthesised for 63. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₄ H₄₂ N₂ OSi: M+1 883.3

¹ H NMR (400MHz, CDCl₃) δ 7.98-7.92 (m, 2H), 7.83-7.77 (m, 3H), 7.72-7.38 (m, 13H), 7.32-7.10 (m, 11H), 7.06-6.88 (m, 6H), 6.86-6.76 (m, 3H), 6.72-6.66 (m, 4H),

Synthesis of compound 82

Compound 1 synthesis and similarly intermediates I-1, intermediates using S-11 and intermediates S-5 the compounds have been synthesised a 82. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₆₈ H₅₁ FN₂ Si₂: M+1 971.4

¹ H NMR (400MHz, CDCl₃) δ 8.01 (d, 2H), 7.83-7.79 (m, 2H), 7.72-7.47 (m, 17H), 7.42-7.20 (m, 10H), 7.13-7.08 (m, 2H), 7.03-6.94 (m, 3H), 6.92-6.86 (m, 1H), 6.82-6.76 (m, 2H), 0.33 (s, 6H), 0.24 (s, 6H)

Synthesis example 4: synthesis of H-9 compound

10-(1-naphthyl) anthracene-9- [...] arrangements 4.3 g (10.0 mmol), 1-(4-bromo phenyl) naphthalene 3.1 g (11.0 mmol), Pd (PPh₃)₄ 0.58 g (0.5 mmol) and K₂ CO₃ 4.1 g (30.0 mmol) for THF/H2O (2/1) senses a rotation velocity of the disk to 40 ml mixed solution 80^o C in adaptation stirring time 5. After marked on the specific room temperature a reaction solution are said possible with conventional 40 ml 40 ml water extracted burn 3 to 30 parts by weight of diethyl ether. Magnesium the organic layer collected bisulphate to dry vaporize solvent in preference to car gel tube silica residue is obtained by separating the compounds purification H-9 4.3 g (84% yield) is obtained. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₄₀ H₂₆: M+1 507.2

¹ H NMR (400MHz, CDCl₃) δ 8.26 (d, 1H), 8.07 (d, H), 8.04-7.93 (m, 7H), 7.87 (d, 2H), 7.74-7.70 (m, 2H), 7.67 (dd, 1H), 7.61-7.49 (m, 4H), 7.47 (d, 2H), 7.38-7.34 (m, 2H), 7.27-7.19 (m, 4H)

Synthesis of H-45 compound

Compound H-9 synthesis and the same method of a compound using intermediates in said formula in a H-9 have been synthesised at a yield of 86%. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₃₆ H₂₄: M+1 457.2

¹ H NMR (400MHz, CDCl₃) δ 8.08 (d, 1H), 7.75 (d, 2H), 7.68 (d, 2H), 7.65-7.52 (m, 11H), 7.42 (dt, 1H), 7.40 (dt, 1H), 7.31 (dd, 2H), 7.24-7.20 (m, 4)

Synthesis of H-60 compound

Compound H-9 synthesis and the same method of a compound using intermediates in said formula in a H-60 have been synthesised at a yield of 81%. The resulting compound is the LC-MS and¹ H NMR it is found out that through. C₄₅ H₃₂: M+1 573.3

¹ H NMR (400MHz, CDCl₃) d 8.05 (d, 2H), 7.76-7.55 (m, 12H), 7.45 (dt, 2H), 7.39-7.28 (m, 6H), 7.26-7.18 (m, 4H), 1.66 (s, 6H)

In the embodiment 1

Coning (corning) 15 Ω / cm2 (1200 °C) ITO anode sized 50 mm x 50 mm x 0.7 mm glass substrate is provided reduce the manufacturing time of increasing the and the pure isopropyl alcohol 5 minutes after cleaning the ultrasonic, ultraviolet rays are irradiated 30 minutes and exposed to ozone cleaning and vacuum deposition a dicing device is provided with a glass substrate the device.

Said substrate as hole injection layer to the data and publicly known material, 4, 4 '-Bis[N-phenyl-N-(9-phenylcarbazol-3-yl) amino]-1, 1' -biphenyl (compound 300) the vacuum deposition of formed to a thickness after 600 Å, then publicly known material, hole-transporting compound as N-[ 1, 1'-biphenyl]-4-yl-9, 9-dimethyl-N-[ 4-(9-phenyl-9H-carbazol-3-yl) phenyl] a thickness of 300 Å-9H-Fluoren-2-amine (compound 311) of the front/rear sides of the hole transporting layers the vacuum deposition.

Publicly known host fluorescent on said upper hole transport layer of blue fluorescent a host, and 1-9, naphthalene-2-yl-anthracene -10-di (hereinafter, ADN) and blue fluorescent with a dopant of the present invention formula I compounds of the deposition chamber is maintained at the 98:2 weight ratio in the 14 to simultaneously carry the front/rear sides of the light emitting layer to have thicknesses on the order of 300 Å.

Then the light takeout efficiency and said a Alq3 in the deposited thickness of 300 Å, alkali metal a halided upper the light takeout efficiency is LiF an electronic injection layer in a thickness of 10 Å is deposited on the, Al a vacuum deposition to have thicknesses on the order of 3000 Å (cathode electrode) the LiF/Al insulation layer is formed have been prepared organic electroluminescent device.

In the embodiment 2

In forming a layer of a light emitting compound instead using said compound 14 except for the host supplying 24, in the embodiment 1 and a second stage constructed with a organic EL device.

In the embodiment 3

In forming a layer of a light emitting compound instead using said compound 14 except for the host supplying 29, in the embodiment 1 and a second stage constructed with a organic EL device.

In the embodiment 4

In forming a layer of a light emitting compound instead using said compound 14 except for the host supplying 31, in the embodiment 1 and a second stage constructed with a organic EL device.

In the embodiment 5

In forming a layer of a light emitting compound instead using said compound 14 except for the host supplying 42, in the embodiment 1 and a second stage constructed with a organic EL device.

In the embodiment 6

In forming a layer of a light emitting compound instead using said compound 14 except for the host supplying 54, in the embodiment 1 and a second stage constructed with a organic EL device.

In the embodiment 7

In forming a layer of a light emitting compound instead using said compound 14 except for the host supplying 59, in the embodiment 1 and a second stage constructed with a organic EL device.

In the embodiment 8

In forming a layer of a light emitting compound instead using said compound 14 except for the host supplying 79, in the embodiment 1 and a second stage constructed with a organic EL device.

In the embodiment 9

In forming a layer of a light emitting compound instead using said compound 14 except for the host supplying 82, in the embodiment 1 and a second stage constructed with a organic EL device.

Compared example 1

Light emitting in forming a layer of a publicly known with a dopant N composition, N, N ', N' -tetraphenyl-pyrene-1, 6-diamine (TPD) except for the host supplying using, in the embodiment 1 and a second stage constructed with a organic EL device.

Embodiment 1 table result the first deoxygenator said compared and positive examples showed the clip to.

In the embodiment 10

Light emitting in forming a layer of a publicly known ADN removed from composition of the present invention formula II compounds of which is obtained by using a H9 instead, the present invention compound 29 as dopant paste using equal to in the embodiment 1 except for organic EL device constructed with a.

In the embodiment 11

Instead said compound 29 in forming a layer of a light emitting dopant in which an amount 42 in the embodiment 10 except for paste using organic equal to EL device constructed with a.

In the embodiment 12

Instead said compound 29 in forming a layer of a light emitting dopant in which an amount 54 in the embodiment 10 except for paste using organic equal to EL device constructed with a.

In the embodiment 13

In forming a layer of a light emitting dopant in which an amount said compound 29 79 instead in the embodiment 10 except for paste using organic equal to EL device constructed with a.

In the embodiment 14

In forming a layer of a light emitting dopant in which an amount said compound 29 82 instead in the embodiment 10 except for paste using organic equal to EL device constructed with a.

In the embodiment 15

In forming a layer of a light emitting compound said removed from H9 which is obtained by using a H45 instead, the present invention compound 24 as dopant paste using equal to in the embodiment 10 except for organic EL device constructed with a.

In the embodiment 16

In forming a layer of a light emitting dopant in which an amount said compound 24 29 instead paste using the same manner as the calculator and in the embodiment 15 except for organic EL device constructed with a.

In the embodiment 17

In forming a layer of a light emitting dopant in which an amount said compound 24 31 instead paste using the same manner as the calculator and in the embodiment 15 except for organic EL device constructed with a.

In the embodiment 18

In forming a layer of a light emitting dopant in which an amount 42 instead 24 compound said paste using the same manner as the calculator and in the embodiment 15 except for organic EL device constructed with a.

In the embodiment 19

In forming a layer of a light emitting dopant in which an amount 54 instead 24 compound said paste using the same manner as the calculator and in the embodiment 15 except for organic EL device constructed with a.

In the embodiment 20

In forming a layer of a light emitting dopant in which an amount said compound 24 59 instead paste using the same manner as the calculator and in the embodiment 15 except for organic EL device constructed with a.

In the embodiment 21

In forming a layer of a light emitting dopant in which an amount said compound 24 79 instead paste using the same manner as the calculator and in the embodiment 15 except for organic EL device constructed with a.

In the embodiment 22

Light emitting in forming a layer of a removed from H60 H9 instead the use of said compounds, as dopant 31 compound the present invention using the equal to in the embodiment 10 except for the host supplying organic EL device constructed with a.

In the embodiment 23

In forming a layer of a light emitting dopant in which an amount said compound 31 42 instead in the embodiment 22 except for paste using organic equal to EL device constructed with a.

In the embodiment 24

Instead said compound 31 in forming a layer of a light emitting dopant in which an amount 54 in the embodiment 22 except for paste using organic equal to EL device constructed with a.

In the embodiment 25

In forming a layer of a light emitting dopant in which an amount said compound 31 59 instead in the embodiment 22 except for paste using organic equal to EL device constructed with a.

In the embodiment 26

In forming a layer of a light emitting dopant in which an amount said compound 31 79 instead in the embodiment 22 except for paste using organic equal to EL device constructed with a.

In the embodiment 27

In forming a layer of a light emitting dopant in which an amount said compound 31 82 instead in the embodiment 22 except for paste using organic equal to EL device constructed with a.

Compared example 2

Light emitting in forming a layer of a publicly known ADN removed from composition of the present invention formula II compounds of which is obtained by using a H9 instead, TPD publicly known as dopant composition paste using equal to in the embodiment 1 except for organic EL device constructed with a.

Embodiment 2 table result the first deoxygenator said compared and positive examples showed the clip to.

Embodiment of the present invention bringing presence of a basic compound formula 1 by blue compounds dopant layer-type semiconductor layer, and publicly known signal transmitted from the video signal input rises effectiveness compounds of an electrode life, and may yield an.

Furthermore, formula 2 by bringing embodiment of the present invention compounds presence of a basic compound removed as both a is further enhanced and its effect is whether a network is..

Thereby, the cold air flows to the present invention said embodiment and positive examples synthesis but described by reference to, is an exemplary which purpose: to avoid a, belonging to the present invention conventional art having knowledge of various modifications therefrom grow for other and equalization embodiment styles are discussed that will understand. Thus the scope of protection of the present invention technical true a claim the idea is decided by the will should be.