KR20150031396A - New organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound represented by chemical formula 1 and an organic electroluminescent device comprising the same. The organic electroluminescent compound is able to be applied to an organic electroluminescent device as a phosphorescent host material and is able to increase luminance efficiency and device lifetime of the organic electroluminescent device.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same.

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same. More particularly, the present invention relates to a novel organic electroluminescent compound used as a phosphorescent host material and an organic electroluminescent device employing the same.

The most important factor determining the luminous efficiency in an OLED is a light emitting material. Fluorescent materials are widely used as luminescent materials to date, but the development of a phosphorescent material on the mechanism of electroluminescence is one of the best ways to improve the luminous efficiency up to 4 times theoretically. Until now, iridium (III) complexes have been widely known as phosphorescent materials. Materials such as (acac) Ir (btp) 2, Ir (ppy) 3 and Firpic are known for each RGB. Recently, many phosphorescent materials have been studied in Japan and Europe.

CBP is the most widely known host material for a phosphorescent light emitting material, and a high efficiency OLED using a hole blocking layer such as BCP and BAlq is known. In Pioneer Japan, a high performance OLED using a BAlq derivative as a host is known There is one.

However, existing materials have advantages in terms of luminescence properties, but they have disadvantages such as low glass transition temperature and very poor thermal stability, such as material changes when subjected to a high temperature deposition process under vacuum. Because OLEDs have power efficiency = (π / voltage) ㅧ current efficiency, the power efficiency is inversely proportional to the voltage. OLEDs using real phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials. However, when conventional materials such as BAlq and CBP are used as hosts for phosphorescent materials, OLEDs using fluorescent materials (Lm / w) since the driving voltage is high. In addition, since the lifetime of the OLED device is never satisfactory, development of a more stable and more excellent host material is required.

The present invention can be applied to a western electroluminescent device as a phosphorescent host material, an organic electroluminescent device capable of lowering a driving voltage when applied to an organic electroluminescent device, and an organic luminescent compound capable of improving luminous efficiency, brightness, thermal stability, The purpose is to provide.

It is another object of the present invention to provide an organic electroluminescence device using the above compound.

The present invention provides an organic electroluminescent compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In this formula,

X is hydrogen, deuterium, C ₁ ~ C ₁₀ straight or branched chain alkyl, C ₁ ~ alkoxy, halogen, nitrile of _{C 10, CF 3, Si (} CH 3) 3, phenyl, naphthyl, phenanthrenyl, fluorenyl Pyrimidinyl, pyridinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, An arylene group having 6 to 30 carbon atoms or a heteroarylene group having 3 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of pyrimidinyl and triazinyl groups;

Each Y is independently nitrogen or carbon, and at least one of the three Y's is nitrogen;

R 1, R 2, R 3 and R 4 are each independently selected from the group consisting of C ₁ -C ₁₀ linear or branched alkyl, C ₁ -C ₁₀ alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, naphthyl , Biphenyl, phenanthrenyl, fluorenyl, 9,9-dimethylfluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, An aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of halogen, pyridazinyl, pyridinyl, pyrimidinyl and triazinyl groups.

The organic electroluminescent compound according to the present invention can be applied to an organic electroluminescent device as a phosphorescent host material. When applied to an organic electroluminescent device, the electroluminescent compound lowers a driving voltage and improves luminous efficiency, brightness, thermal stability, and device life.

In addition, the organic electroluminescent device manufactured using the organic electroluminescent compound of the present invention has high efficiency and long life.

While the present invention has been described in connection with certain embodiments, it is obvious that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the invention. It is to be understood, however, that the invention is not intended to be limited to the particular forms disclosed, but on the contrary, is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the term " comprising " or " consisting of ", or the like, refers to the presence of a feature, a number, a step, an operation, an element, a component, But do not preclude the presence or addition of one or more other features, integers, steps, operations, components, parts, or combinations thereof.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.

The present invention relates to an organic electroluminescent compound, particularly a triphenylene triazine-based material, which is used as an electron transport layer (ETM), a light emitting layer (EML), a hole transport layer (HTM) We will present various materials that can be used in various ways, and develop materials that improve performance such as efficiency and drive voltage reduction and maximize their ability as OLED materials.

In the present specification, the term "organic photocompound" means a compound used in an organic photonic device. The scope of the present invention is not limited to the organic luminescent layer. The scope of the present invention is not limited to the organic luminescent layer. Can be used for any layer constituting the substrate.

In this specification, the terms 'optical compound' and 'optical device' are used to cover the case where the present invention is applied to both an organic light emitting device and a device for solar power generation regardless of a dictionary or conventional definition It is a selected term.

An organic photonic device according to a first aspect of the present invention includes: a first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode.

The organic photo-compound used in the organic photonic device of the present invention may have a structure of the following general formulas (1) to (85) (hereinafter, the chemical formulas are omitted and only numerals are shown)

The present invention relates to organic electroluminescent compounds represented by the following general formula (1)

[Chemical Formula 1]

In this formula,

X is hydrogen, deuterium, C ₁ ~ C ₁₀ straight or branched chain alkyl, C ₁ ~ alkoxy, halogen, nitrile of _{C 10, CF 3, Si (} CH 3) 3, phenyl, naphthyl, phenanthrenyl, fluorenyl Pyrimidinyl, pyridinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, An arylene group having 6 to 30 carbon atoms or a heteroarylene group having 3 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of pyrimidinyl and triazinyl groups;

Each Y is independently nitrogen or carbon, and at least one of the three Y's is nitrogen;

R 1, R 2, R 3 and R 4 are each independently selected from the group consisting of C ₁ -C ₁₀ linear or branched alkyl, C ₁ -C ₁₀ alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, naphthyl , Biphenyl, phenanthrenyl, fluorenyl, 9,9-dimethylfluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, An aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of halogen, pyridazinyl, pyridinyl, pyrimidinyl and triazinyl groups.

또는

이며, 여기에서, R5, R6, R7, R8, R9, R10, R11 및 R12는 각각 독립적으로, 수소, 중수소, C₁~C₁₀의 직쇄 또는 분지쇄 알킬, C₁~C₁₀의 알콕시, 할로겐, 니트릴, CF₃,Si(CH₃)₃,페닐, 나프틸, 페난트레닐, 플루오레닐, 9,9-디메틸플루오레닐, 피롤, 피라졸, 이미다졸, 트리아졸, 옥사졸, 옥사디아졸, 티오페닐, 티아졸, 티아디아졸, 피라지닐, 피리다지닐, 피리디닐, 피리미디닐 또는 트리아지닐기이며, 상기 R6 및 R7는 함께 옥소(= O)기일 수 있으며;Preferably, the above-mentioned arylene having 6 to 30 carbon atoms or the heteroarylene having 3 to 30 carbon atoms is at least one selected from the group consisting of phenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, pyrrolene, pyrazolene, imidazolene, A thiophene, a thiophene, a thienylene, a thienylene, a thienylene, a thienylene, an oxazole, an oxadiazolene, a thiophenylene, a thiazolene, a thiadiazolene, a pyridinylene, a pyrimidinylene, a pyrazinylene, Naphthylene, naphthylene, naphthylene, naphthylene, naphthylene, naphthylene, naphthylene, naphthylene,

or

And, in which, R5, R6, R7, R8, R9, R10, R11 and R12 are each independently, hydrogen, deuterium, C ₁ ~ C ₁₀ straight or branched chain alkyl, C ₁ ~ alkyl, halogen, C ₁₀ , _{nitrile, CF 3, Si (CH 3} ) 3, phenyl, naphthyl, phenanthrenyl, fluorenyl, 9,9-dimethyl-fluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxazolo A thiazole, a thiadiazole, a pyrazinyl, a pyridazinyl, a pyridinyl, a pyrimidinyl or a triazinyl group, and R6 and R7 together may be an oxo (= O) group;

The heteroaryl group having 6 to 30 carbon atoms and the heteroaryl group having 3 to 30 carbon atoms may be substituted with at least one selected from the group consisting of phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxadiazole, And examples thereof include phenyl, thiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzothiazole, carbazole, quinolinyl, iso Quinolinyl, or an indole group.

More preferably,

,

또는

이며, 여기에서, R5, R6, R7, R8, R9, R10, R11 및 R12는 각각 독립적으로, 수소, 중수소, C₁~C₁₀의 직쇄 또는 분지쇄 알킬, 페닐 또는 나프틸기이며, 상기 R6 및 R7는 함께 옥소(= O)기일 수 있으며;Wherein X is selected from the group consisting of hydrogen, deuterium, linear or branched C ₁ to C ₅ alkyl, C ₁ to C ₁₀ alkoxy, or a substituted or unsubstituted phenylene, naphthylene, anthracenylene, phenanthrenylene, Nylene, thiophenylene,

,

or

And, in which, R5, R6, R7, R8, R9, R10, R11 and R12 are each independently hydrogen, deuterium, linear or branched alkyl, phenyl or naphthyl group of C ₁ ~ C _10, wherein R6 and R7 together may be an oxo (= O) group;

Each Y is independently nitrogen or carbon, and at least one of the three Y's is nitrogen;

R1 and R2 are hydrogen;

R3 and R4 can be a each independently, C ₁ ~ C ₁₅ straight or branched chain alkyl group and a phenyl group naphthalimide phenyl, unsubstituted or substituted with one or more substituents selected from alkylenyl, or pyridinyl.

Further, the organic electroluminescent device of the present invention may further include at least one compound selected from the group consisting of an arylamine compound and a styrylarylamine compound, which comprises at least one organic luminescent compound according to the above formula (1) can do.

Further, in the organic electroluminescent device of the present invention, in addition to one or more organic luminescent compounds according to the above formula (1), at least one group 1, group 2, group 4, group 5 transition metal, lanthanide series metal and d- , And the organic material layer may include a light emitting layer and a charge generating layer.

Further, an organic electroluminescent device emitting white light by simultaneously including at least one organic light emitting layer emitting blue, red or green light in addition to the organic light emitting compound according to Formula 1 may be formed in the organic material layer.

The organic electroluminescent device further includes a first electrode; A second electrode; And at least one organic compound layer interposed between the first electrode and the second electrode, wherein the organic compound layer comprises an organic light emitting compound according to Formula 1 and a combination of two or more organic light emitting compounds having different structures except the structure , Each of which may comprise from about 3% to about 97% by weight.

IDE102, IDE105 available from Idemitsu Co., Ltd. and C545T commercially available from Hayashibara Co., Ltd. can be used as the dopant material. As the phosphorescent dopant, red phosphorescent dopant PtOEP, UDC RD61, green phosphorescent dopant Ir (PPy ) 3 (where PPy is 2-phenylpyridine), F2Irpic as a blue phosphorescent dopant, and RD 61 as a red light dopant of UDC. N-methylquinacridone (MQD), coumarine derivatives and the like can also be used. Further, a metal-ligand complex compound represented by the following formula [D] can also be used.

[Chemical Formula D]

M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³

Wherein M ¹ is selected from the group consisting of metal elements of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 on the periodic table; ¹⁰¹ , L ¹⁰² , and L ¹⁰³ are each selected from the following structures as ligands;

,

또는

이며, R₂₃₁내지 R₂₄₂는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 C₁∼C₃₀의 알킬기, C₁∼C₃₀의 알콕시기, 할로겐이 치환 또는 비치환된 C₆∼C₃₀의 아릴기, 시아노가 치환 또는 비치환된 C₅∼C₃₀의 시클로알킬기이거나, 인접한 치환체와 C₃∼C₁₂의 알킬렌 또는 C₃∼C₁₂의 알케닐렌으로 연결되어 스피로 고리 또는 축합고리를 형성할 수 있거나, R₂₀₇또는 R₂₀₈과 C₃∼C₁₂의 알킬렌 또는 C₃∼C₁₂의 알케닐렌으로 연결되어 포화 또는 불포화의 축합고리를 형성할 수 있다.At this time, the R _201, R _202, and R ₂₀₃ each represent a hydrogen atom, an alkyl group with or without halogen substituent _{C 1 ~C 30, C 1 ~C} 30 alkyl is optionally substituted C ₁ ~C ₅₀ of An aryl group, or a halogen atom; R ₂₀₄ to R ₂₁₉ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, a substituted or unsubstituted C ₃ to C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ ~C ₃₀ uial Kane group, a substituted or unsubstituted mono or a substituted or unsubstituted aryl group, a substituted or unsubstituted C ₆ ~C ₃₀ ring-di (C ₁ ~C ₃₀ alkyl) amino group, a substituted or unsubstituted mono- or di-ring - (C ₆ ~C ₃₀ aryl) amino group, a SF5, substituted or unsubstituted tree (C ₁ ~C ₃₀ of alkyl) silyl group, a substituted or unsubstituted ring (C _{1 to} C ₃₀ alkyl) (C _{6 to} C ₃₀ aryl) silyl group, a substituted or unsubstituted tri (C _{6 to} C ₃₀ aryl) silyl group, a cyano group or a halogen atom; R ₂₂₀ to R ₂₂₃ each independently represent a hydrogen atom, a deuterium atom, a C _{1 to} C ₃₀ alkyl group with or without halogen substitution, or a C _{6 to} C ₃₀ substituted or unsubstituted C _{1 to} C ₃₀ alkyl An aryl group; R ₂₂₄ and R ₂₂₅ are independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C ₁ ~C ₃₀ alkyl group, a substituted or unsubstituted C ₆ ~C ₃₀ aryl group, or a halogen atom, R ₂₂₄ and R ₂₂₅ is connected by including the fused ring does not contain, or C ₃ ~C ₁₂ alkylene or C ₃ ~C ₁₂ of alkenylene to form an aliphatic ring, or a monocyclic or multi-fused ring, and; R ₂₂₆ is a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, a substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group, or a halogen atom; R ₂₂₇ to R ₂₂₉ independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, or a halogen atom; Q is

,

or

And, R ₂₃₁ to R ₂₄₂ independently represent hydrogen, deuterium, an alkyl group with or without halogen substituent _{C 1 ~C 30, C 1 ~C} 30 alkoxy group, a halogen-substituted or unsubstituted C ₆ ~C each other ₃₀ aryl group, a cyano furnace a substituted or unsubstituted C ₅ ~C _30, or a cycloalkyl group, an alkenylene with the adjacent substituents with C ₃ ~C ₁₂ alkylene or C ₃ ~C ₁₂ of the spiro ring or a condensed ring may form a, alkenylene of R ₂₀₇ or R ₂₀₈ and C ₃ ~C ₁₂ alkylene or a C ₃ ~C ₁₂ may form a fused ring, saturated or unsaturated.

The doping concentration is not particularly limited, but the content of the dopant is usually 0.01 to 15 parts by weight based on 100 parts by weight of the host. The thickness of the light emitting layer may be about 100 A to 1000 A, preferably 200 A to 600 A, When the thickness of the light emitting layer is less than 100 ANGSTROM, the light emission characteristics may be degraded. When the thickness of the light emitting layer is more than 1000 ANGSTROM, the driving voltage may increase.

When a luminescent compound is used together with a phosphorescent dopant in the luminescent layer, a method such as vacuum deposition, spin coating, casting, LB or the like is performed on the luminescent layer to prevent the triplet excitons or holes from diffusing into the electron transporting layer The hole blocking layer HBL can be formed. When the hole blocking layer is formed by a vacuum deposition method or a spin coating method, the conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer. Known hole blocking materials that can be used include oxadiazole derivatives, triazole derivatives (TAZ), phenanthroline derivatives (BCP), and the like.

The thickness of the hole blocking layer may be about 50 Å to 1000 Å, preferably 100 Å to 300 Å. When the thickness of the hole blocking layer is less than 50 ANGSTROM, the hole blocking characteristics may be deteriorated. When the thickness of the hole blocking layer is more than 1000 ANGSTROM, the driving voltage may increase.

Next, an electron transport layer (ETL) is formed by various methods such as a vacuum evaporation method, a spin coating method, and a casting method.

In the case of forming the electron transporting layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but generally, the conditions are substantially the same as those for forming the hole injection layer. The electron transport layer material serves to stably transport electrons injected from an electron injection electrode, and quinoline derivatives, particularly known materials such as Alq3, TAZ, Balq, PBD and the like may be used.

The thickness of the electron transporting layer may be about 100 ANGSTROM to 1000 ANGSTROM, preferably 200 ANGSTROM to 500 ANGSTROM. When the thickness of the electron transporting layer is less than 100 ANGSTROM, the electron transporting property may be degraded. When the thickness of the electron transporting layer is more than 1000 ANGSTROM, the driving voltage may increase.

Further, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transporting layer, which is not particularly limited. As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li ₂ O, BaO, or the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer. The thickness of the electron injection layer may be about 1 A to 100 A, preferably 5 A to 50 A. If the thickness of the electron injection layer is less than 1 A, the electron injection characteristics may be deteriorated. If the thickness of the electron injection layer exceeds 100 A, the driving voltage may increase.

Finally, the second electrode can be formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like.

The second electrode may be used as a cathode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, or a mixture thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- .

Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic luminescent compound of the present invention can be usefully used as a phosphorescent host material.

Representative examples of the organic luminescent compound of the present invention include compounds 1 to 85 described in the following [first group (s)]:

 [First group (group)]

The present invention also relates to

An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more thereof.

The organic light emitting compound is a phosphorescent host material, and may be included in the light emitting layer.

The organic electroluminescent device

Emitting layer interposed between the anode, the hole injection layer, the hole transport layer, the electron transport layer, the electron injection layer, and the cathode.

Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the following examples do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention may have a structure in which a cathode (a hole injection electrode), a hole injection layer (HIL) and / or a hole transport layer (HTL), a light emitting layer (EML) Preferably, an electron blocking layer (EBL) may be additionally provided between the anode and the light emitting layer, and an electron transport layer (ETL), an electron injection layer (EIL) or a hole blocking layer (HBL) have.

In the method of manufacturing an organic electroluminescence device according to the present invention, a cathode material is coated on the surface of a substrate by a conventional method to form a cathode. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. As the material for the positive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity may be used.

Next, a hole injection layer (HIL) material is formed on the surface of the anode by vacuum thermal deposition or spin coating using a conventional method. Examples of such hole injection layer materials include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4' Amino) phenoxybenzene (m-MTDAPB), starburst type amines such as 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4' Triphenylamine (2-TNATA) or IDE406 available from Idemitsu, for example.

A hole transport layer (HTL) material is vacuum-deposited or spin coated on the surface of the hole injection layer by a conventional method to form a hole transport layer. In this case, the hole transport layer material may be at least one selected from the group consisting of bis (N- (1-naphthyl-n-phenyl)) benzidine (? -NPD), N, -Benzidine (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD).

A light emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the organic luminescent compound of the present invention may be used as a phosphorescent host material when the single luminescent material or the luminescent host material is green, and tris (8-hydroxyquinolinolato) aluminum (Alq3) (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), spiro (Spiro-4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazolyl) (Phenol lithium salt), bis (biphenylvinyl) benzene, aluminum-quinoline metal complex, imidazole, thiazole and oxazole metal complexes.

Among the light emitting layer materials, IDE102 and IDE105 available from Idemitsu as phosphorescent dopants and tris (2-phenylpyridine) iridium (III) (Ir (ppy ) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinate-N, C-2 '] picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys Platy (II) octaethylporphyrin (PtOEP), TBE002 (Cobion), and the like can be used.

An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the electron transporting material to be used is not particularly limited, and tris (8-hydroxyquinolinolato) aluminum (Alq3) can be preferably used.

Alternatively, by further forming a hole blocking layer (HBL) between the light emitting layer and the electron transporting layer and using a phosphorescent dopant together with the light emitting layer, it is possible to prevent the phenomenon that the triplet excitons or holes are diffused into the electron transporting layer.

The hole blocking layer can be formed by vacuum thermal deposition and spin coating using a hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, there is no particular limitation, but (8-hydroxyquinolinolato Lithium biphenoxide (BAlq), bathocuproine (BCP), LiF, etc. may be used as the lithium salt (Li), bis (8-hydroxy-2-methylquinolinonato)

An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the material of the electron injection layer to be used is not particularly limited, and preferably materials such as LiF, Liq, Li2O, BaO, NaCl, and CsF can be used.

Finally, a negative electrode is formed on the surface of the electron injecting layer by vacuum thermal deposition using a conventional method.

At this time, as the negative electrode material to be used, lithium, aluminum, aluminum-lithium, calcium, magnesium, (Mg-Ag) or the like may be used. In the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode capable of transmitting light.

The organic electroluminescent device according to the present invention may be manufactured in the order as described above, that is, in the order of anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode, Electron injecting layer / electron transporting layer / hole blocking layer / light emitting layer / positive hole transporting layer / positive hole injecting layer / positive electrode, or may be modified so as to have various layer orders or adjustable structures of specific layers.

Hereinafter, a method of synthesizing the compounds of the present invention will be described with reference to representative examples. However, the method of synthesizing the compounds of the present invention is not limited to the following exemplified methods, and the compounds of the present invention can be produced by the methods exemplified below and by methods known in the art.

Preparation of compound [1]

[Reaction Scheme 1]

Preparation of intermediate compound [1-1]

In a 500 mL three-necked reaction flask, 34.7 g (0.147 mol) of 1,4-dibromobenzene, 20.0 g (73.5 mmol) of triphenylene-2-ylboronic acid, 1.7 g ) And 15.2 g (0.110 mmol) of potassium carbonate (K ₂ CO ₃ ), and the mixture was stirred under reflux for 12 hours with 250 mL of 1,4-dioxane and 25 mL of purified water under a nitrogen stream. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid was washed with purified water and methanol, and recrystallized from dichloromethane and methanol to give 25.0 g (89%) of intermediate compound [1-1] as a white solid.

Preparation of intermediate compound [1-2]

25.0 g (65.23 mmol) of [1-1] and 30 ml of anhydrous tetrahydrofuran were placed in a 500 ml reaction flask, and the mixture was stirred at -78 ° C in a nitrogen stream. 31.3 mL (78.28 mmol) of n-butyllithium (2.5 M in hexane) is added dropwise at the same temperature, and after 30 minutes, 8.7 mL (78.28 mmol) of trimethylborate is added dropwise. The reaction temperature is slowly raised to room temperature for 8 hours, extracted with ethyl acetate and saturated aqueous ammonium solution, the organic layer is separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and then recrystallized from dichloromethane and hexane to obtain 15.0 g (66%) of intermediate compound [1-2].

Preparation of compound [1]

To a 250 mL reaction flask was added 7.15 g (20.54 mmol) of the intermediate compound [1-2], 5.0 g (18.67 mmol) of 2-chloro-4,6-diphenyl-1,3,5- (0.373 mmol) of palladium and 3.87 g (28.00 mmol) of potassium carbonate (K ₂ CO ₃ ). The mixture was stirred under reflux for 6 hours with 100 mL of 1,4-dioxane and 10 mL of purified water under a nitrogen stream. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid was washed with purified water and methanol, and recrystallized from dichloromethane and methanol to give 7.1 g (71%) of the desired compound [1] as a white solid.

According to the method of Scheme 1 above, compounds 1 to 85 were prepared and the results are shown below in the second group of tablets.

[Second group (group)]

Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

Comparative Example 1

Wherein the compound represented by the following formula (a) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq3 (30 nm) / LiF (30 nm) / Compound (30 nm) / Compound (a) 0.5 nm) / Al (60 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, UV ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Formula (a) and a compound represented by Formula (c) (10% doping) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in Table 3. This is referred to as Comparative Sample 1.

Comparative Example 2

Wherein the compound represented by the following formula (b) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq3 (30 nm) / LiF (30 nm) / compound (30 nm) / compound (30 nm) / ITO / 2-TNATA 0.5 nm) / Al (60 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, UV ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by the formula (b) and a compound represented by the formula (c) (10% doping) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to produce an organic light emitting device as shown in the first table group. This is referred to as Comparative Sample 2.

Examples 1-85.

ITO / 2-TNATA (80 nm) was prepared in the same manner as in Comparative Example 1, except that Compound (a) shown in the above Synthesis Example was used instead of Compound (a) (30 nm) / Alq ₃ (30 nm) / LiF (0.5 nm) / Al (60 nm) /? -NPD (30 nm) / [one of phosphorescent green host compounds 1-85 + compound c Structure was prepared. These are referred to as Samples 1 to 85, respectively.

Evaluation Example 1: Evaluation of luminescence characteristics of Comparative Samples 1 and 2 and Samples 1 to 85

The luminescence brightness, luminescence efficiency and luminescence peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 1 and 2 and Samples 1 to 85, (Group)]. The samples showed green emission peak values in the range of 513 to 524 nm.

[Group 3]

Samples 1 to 85 exhibited improved luminescence characteristics as compared to Comparative Samples 1 and 2, as shown in the [third set of group (s)] above.

Evaluation Example 2: Evaluation of life characteristics of Comparative Samples 1 and 2 and Samples 1 to 85

For Comparative Samples 1 and 2 and Samples 1 to 85, the time at which the lifetime reached 97% based on 3500 nit was measured using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following 4 group (group)].

[Group 4]

 Samples 1 to 85 exhibited improved lifespan characteristics as compared to Comparative Samples 1 and 2, as confirmed from [fourth set of group (s)].

Claims (8)

An organic light-emitting compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
X is hydrogen, deuterium, C ₁ ~ C ₁₀ straight or branched chain alkyl, C ₁ ~ alkoxy, halogen, nitrile of _{C 10, CF 3, Si (} CH 3) 3, phenyl, naphthyl, phenanthrenyl, fluorenyl Pyrimidinyl, pyridinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, An arylene group having 6 to 30 carbon atoms or a heteroarylene group having 3 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of pyrimidinyl and triazinyl groups;
Each Y is independently nitrogen or carbon, and at least one of the three Y's is nitrogen;
R1, R2, R3 and R4 are each independently hydrogen, deuterium, C ₁ ~ C ₁₀ straight or branched chain alkyl, C ₁ ~ alkoxy, halogen, nitrile of _{C 10, CF 3, Si (} CH 3) 3, Phenyl, naphthyl, biphenyl, phenanthrenyl, fluorenyl, 9,9-dimethylfluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thia An aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of pyrrolidinyl, pyridazinyl, pyridinyl, pyridinyl, pyrimidinyl and triazinyl groups, to be. The method according to claim 1,
The above-mentioned arylene having 6 to 30 carbon atoms or the heteroarylene having 3 to 30 carbon atoms is preferably selected from the group consisting of phenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, pyrrolene, pyrazolene, imidazolene, triazolene, , Oxadiazole, thiophenylene, thiazole, thiadiazole, pyridinylene, pyrimidinylene, pyrazinylene, pyridazienylene, triazienylene, benzothiophenylene, benzimidazolinylene, benzoxazine Benzothiazolinylene, quinolinylene, isoquinolinylene, indolinylene group,

or

And, in which, R5, R6, R7, R8, R9, R10, R11 and R12 are each independently, hydrogen, deuterium, C ₁ ~ C ₁₀ straight or branched chain alkyl, C ₁ ~ alkyl, halogen, C ₁₀ , _{nitrile, CF 3, Si (CH 3} ) 3, phenyl, naphthyl, phenanthrenyl, fluorenyl, 9,9-dimethyl-fluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxazolo A thiazole, a thiadiazole, a pyrazinyl, a pyridazinyl, a pyridinyl, a pyrimidinyl or a triazinyl group, and R6 and R7 together may be an oxo (= O) group;
The heteroaryl group having 6 to 30 carbon atoms and the heteroaryl group having 3 to 30 carbon atoms may be substituted with at least one selected from the group consisting of phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxadiazole, And examples thereof include phenyl, thiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzothiazole, carbazole, quinolinyl, iso Or an indole group, or an indole group. The method according to claim 1,
X is selected from the group consisting of hydrogen, deuterium, linear or branched C ₁ -C ₅ alkyl, C ₁ -C ₁₀ alkoxy, or substituted or unsubstituted phenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene , Thiophenylene,

,

or

And, in which, R5, R6, R7, R8, R9, R10, R11 and R12 are each independently hydrogen, deuterium, linear or branched alkyl, phenyl or naphthyl group of C ₁ ~ C _10, wherein R6 and R7 together may be an oxo (= O) group;
Each Y is independently nitrogen or carbon, and at least one of the three Y's is nitrogen;
R1 and R2 are hydrogen;
R3 and R4 are, each independently, characterized in that characterized in that a substituted or unsubstituted phenyl, naphthalenyl, or pyridinyl group with one or more substituents selected from a C ₁ ~ C ₁₅ straight or branched chain alkyl group and a phenyl group Lt; / RTI > The method of claim 3,
Wherein the organic light emitting compound is any one of the following compounds 1 to 85:

The method according to claim 1,
Wherein the organic light emitting compound is a phosphorescent host material in a material for an organic electroluminescence device. An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,
Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of claim 1 singly or in combination of two or more. The method according to claim 6,
Wherein the organic light emitting compound is a phosphorescent host material and is contained in the light emitting layer. 8. The method according to claim 6 or 7,
The organic electroluminescent device
Wherein the light emitting layer is contained in a light emitting layer interposed between the anode, the hole injecting layer, the hole transporting layer, the electron transporting layer, the electron injecting layer, and the cathode.