KR101663527B1 - New organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Abstract

상기 유기발광화합물은 발광층 물질, 정공주입층 물질, 정공수송층 물질, 전자주입층 물질, 전자수송층 물질, 전자차단층 물질, 및 정공차단층 물질로서 유기전계발광소자에 적용될 수 있으며, 이 경우 유기전계발광소자의 발광효율 및 소자 수명을 향상시킬 수 있다. The present invention provides an organic compound represented by the following formula (1) and an organic electroluminescent device including the organic compound:
[ Chemical Formula 1 ]

The organic light emitting compound may be applied to an organic electroluminescent device as a light emitting layer material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, an electron transporting layer material, an electron blocking layer material, and a hole blocking layer material. The luminous efficiency and lifetime of the light emitting element can be improved.

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 novel organic compounds and organic electroluminescent (EL) devices comprising them.

An electroluminescence device (EL device) is a self-emissive type display device having a wide viewing angle and excellent contrast as well as a high response speed. In 1987, Eastman Kodak Co., An organic EL device using an aromatic diamine and an aluminum complex having low molecular weight has been developed for the first time [Appl. Phys. Lett. 51, 913, 1987].

C. Tang et al. Applied Physics, Vol. 65, Pages 3610-3616, (1989)), a three-layer organic EL device containing an organic electroluminescent layer between a hole transporting layer and an electron transporting layer has also been proposed. The light emitting layer is typically made of a host material doped with a guest material. Further, a four-layer EL element including a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and an electron transport layer has been proposed in US 4769292. These structures showed improved device efficiency.

Many luminescent materials described as useful in OLED devices emit light from their excited singlet state by fluorescence. An excited singlet state is generated when the excitons generated in the OLED elements transmit their energy to the excited state of the dopant. However, in general, only 25% of the excitons generated in the EL device are considered to be singlet excitons, and the remaining excitons are triplet, which can not easily transfer their energy to the singlet excited state of the dopant. Since 75% of the excitons are not used in the luminescence process, this results in a significant loss of efficiency.

Triplet excitons can transfer their energy to the dopant if the dopant has a sufficiently low triplet excitation state in terms of energy. If the triplet state of the dopant is luminescent, it can emit light by phosphorescence. In many cases, singlet excitons can also transfer their energy to the lowest singlet excited state of the same dopant. Singlet excited states can often be relaxed to a luminescent triplet excited state by intermixing processes. Thus, by appropriate selection of the host and dopant, energy can be collected from the singlet and triplet excitons generated in the OLED device and highly efficient phosphorescent emission can be generated.

The most important factors for determining the performance such as luminous efficiency and lifetime in an organic EL device are the luminescent material. Some characteristics required for such a luminescent material are that the fluorescent quantum yield in a solid state must be large, and the mobility of electrons and holes And should not be easily decomposed during vacuum deposition, and should form a uniform thin film and be stable.

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, and a BAlq derivative is also used as a host in Pioneer of Japan.

  However, the conventional materials are advantageous from the viewpoint of the luminescence characteristics, but they have disadvantages such as low thermal stability and low glass transition temperature, and material changes during the deposition process. In OLED devices, the power efficiency is inversely proportional to the voltage, and the lower the power consumption, the higher the power efficiency. An EL device using an actual phosphorescent material has a significantly higher current efficiency (cd / A) than an EL device using a fluorescent material. However, when a conventional material such as BAlq or CBP is used as a host of a phosphorescent material, There is no great advantage in terms of power efficiency (lm / w) because the driving voltage is higher than that of the conventional device, and the lifetime of the device is never satisfactory. Thus, development of a more stable and superior performance host material is required.

Further, acridine derivative compounds are known as one of materials showing carrier transportability and luminescence characteristics of organic devices.

In US2004001969A1, acridone derivatives were used as dopants,

Also in WO02063698A1, the following figure in the patent shows that the R group linked to N of acridone is limited to halogen or alkyl groups.

In US7842406B2, the following figure in the patent is limited to the N-L-amine group of acridone. In addition, although R1 and R2 are also broad, all the structures of the compounds presented in the patent are all hydrogen.

US20110121280A1 also discusses acridone, but only the alkyl group of N in acridone. In US20080020323A1, as shown in the following figure in the patent, although R5 is connected to N of acondone, R5 is limited to an alkyl or an alkyl group.

JP 4380277B2 also discloses the following figure in the patent that the atom of the acridone is connected to the carbon atom of the compound (A) and is preferably substituted by an aryl group. As a representative example, only the structure in which N of the acridone group (phenyl or biphenyl) is connected to N of the other acridone is exemplified. In addition, the structure of the compound (A) There is nothing.

The acridone derivative is usually limited to a dopant material doped in the light emitting layer like a host, and it has been exemplified that the light emitting efficiency of the device is improved by introducing a hetero group. Also, acridone derivative compounds are exemplified as phosphorescent layers, electron transporting layers, hole injecting and hole transporting layers. It is confirmed that the structure is usable in both fluorescent and phosphorescent materials, and the stability of the structure can be confirmed by exemplifying the characteristics of long life, high luminescence, luminance, and high efficiency.

However, it has been reported that only the alkyl and aryl groups are introduced into N of acridone to improve the characteristics of the organic device, and various substitution, unsubstituted aryl, hetero group and the like are not exemplified. There is no example in which various groups are introduced into the ring next to the N atom to improve the characteristics of the device.

The present invention can be applied to an organic electroluminescent device as a light emitting layer material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, an electron transporting layer material, an electron blocking layer material and a hole blocking layer material. It is an object of the present invention to provide an organic compound capable of lowering the driving voltage of a light emitting element and improving luminous efficiency, luminance, thermal stability, color purity and element life.

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

The present invention provides an organic compound represented by the following Formula 1:

[ Formula 1 ]

In this formula,

A 1, A 2, A 3, A 4, A 5, A 6, A 7 and A 8 are each independently a carbon atom or a nitrogen atom;

In this formula,

A 1, A 2, A 3, A 4, A 5, A 6, A 7 and A 8 are each independently a carbon atom or a nitrogen atom;

E is a single bond; Or an aromatic hydrocarbon group having 4 to 60 carbon atoms and composed of at least one member selected from the group consisting of a nitrogen atom, a substituted or unsubstituted aromatic ring, and a substituted or unsubstituted aromatic heterocycle;

B is absent; Or an aromatic hydrocarbon group having 4 to 60 carbon atoms and composed of at least one member selected from the group consisting of a nitrogen atom, an oxygen atom, a substituted or unsubstituted aromatic ring, and a substituted or unsubstituted aromatic heterocycle;

n is an integer of 0 to 3;

Wherein the aromatic heterocycle comprises at least one atom selected from B, F, N, O, S, P (= O), Si and P;

In the above, A9, A10, A11 or A12 and B may be connected to each other to form a C6-C30 aromatic hydrocarbon group.

Further, according to the present invention,

An organic electroluminescent device having an organic thin film layer sandwiched between a cathode and an anode and comprising one or more layers including at least a light emitting layer,

Wherein at least one of the organic thin film layers contains the organic compound singly or in combination of two or more kinds.

When the organic compound according to the present invention is applied to an organic light emitting device as a light emitting layer material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, an electron transporting layer material, an electron blocking layer material, and a hole blocking layer material, And improves the luminous efficiency, brightness, thermal stability, color purity, and device lifetime.

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

1 is a graph showing the < 1 > H-NMR data of the compound [241-5]
2 is a graph showing the < 1 > H-NMR data of the compound [241-7]
3 is a graph showing the < 1 > H-NMR data of the compound [241-8]
4 is a graph showing the < 1 > H-NMR data of the compound [241-9]
5 is a graph showing the < 1 > H-NMR data of the compound [241-10]
6 is a graph showing the < 1 > H-NMR data of the compound [241]
7 is a graph showing the TGA data of the compound [241]
8 is a graph showing the UV data of the compound [241]
9 is a graph showing PL data of the compound [241]

Hereinafter, the present invention will be described in detail.

While the present invention has been described in connection with certain exemplary embodiments, it is to be understood 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 compound represented by the following general formula

[Chemical Formula 1]

In this formula,

A 1, A 2, A 3, A 4, A 5, A 6, A 7 and A 8 are each independently a carbon atom or a nitrogen atom;

A9, A10, A11 and A12 each independently represent a non-existent; Or an aromatic hydrocarbon group having 4 to 60 carbon atoms and composed of at least one member selected from the group consisting of a nitrogen atom, an oxygen atom, a substituted or unsubstituted aromatic ring, and a substituted or unsubstituted aromatic heterocycle;

L1, L2, L3 and L4 each independently represent a single bond; Or an aromatic hydrocarbon group having 4 to 60 carbon atoms and composed of at least one member selected from the group consisting of a nitrogen atom, a substituted or unsubstituted aromatic ring, and a substituted or unsubstituted aromatic heterocycle; Or a C1 to C50 alkylenyl group;

E is a single bond; Or an aromatic hydrocarbon group having 4 to 60 carbon atoms and composed of at least one member selected from the group consisting of a nitrogen atom, a substituted or unsubstituted aromatic ring, and a substituted or unsubstituted aromatic heterocycle;

B is absent; Or an aromatic hydrocarbon group having 4 to 60 carbon atoms and composed of at least one member selected from the group consisting of a nitrogen atom, an oxygen atom, a substituted or unsubstituted aromatic ring, and a substituted or unsubstituted aromatic heterocycle;

n is an integer of 0 to 3;

Wherein the aromatic heterocycle comprises at least one atom selected from B, F, N, O, S, P (= O), Si and P;

In the above, A9, A10, A11 or A12 and B may be connected to each other to form a C6-C30 aromatic hydrocarbon group.

Preferably,

A9, A10, A11 and A12 each independently represent a non-existent; Or heavy _{hydrogen, Si (CH) 3, CF} 3, substituted or unsubstituted of C1 ~ C10 substituted or unsubstituted alkoxy, C1 ~ C10 of ring-substituted alkyl, phenyl, pyridyl, -N (Ar1) (Ar2) , dibenzo (C 1 -C 10) alkyl substituted with one or more substituents selected from the group consisting of furanyl, dibenzothiophenyl, or a carbazole group (substituted or unsubstituted with a phenyl group or a biphenyl group), phenyl, pyridine, pyrimidine , Triazine, naphthalene, dibenzofuran, dibenzothiophene, carbazole, fluorene, phenanthrene, anthracene, benzoanthracene, triphenylene, tetraphenylene, tetraphenylsilane, triphenylphosphine oxide, , Quinoline, isoquinoline, phenanthridine, or -N (Ar1) (Ar2);

L1, L2, L3 and L4 each independently represent a single bond; (Phenyl, anthracenyl, naphthalenyl, 9,9-dimethy-fluorenyl, and diphenylamino groups) substituted with one or more substituents selected from the group consisting of phenyl, biphenylene, naphthalene, anthracene, carbazole, pyridine, pyrimidine, A hydrocarbon group having 10 to 60 carbon atoms in which at least one compound selected from the group consisting of R < 1 >

Wherein E is composed of a _{phenyl, Si (CH) 3, CF} 3, and a substituted or unsubstituted alkoxy of C1 ~ C10 substituted with an alkyl group of heavy hydrogen, substituted or unsubstituted of C1 ~ C10 unsubstituted alkyl, phenyl, C1 ~ C10 A substituted or unsubstituted phenyl group optionally substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, pyridine, pyrimidine, triazine, naphthalene, dibenzofuran, dibenzothiophene, carbazole, fluorene, phenanthrene, anthracene, , Triphenylene, tetraphenylene, tetraphenylsilane, triphenylphosphine oxide, tetraphenylmethane, or (phenyl, anthracene, naphthalene, 9,9-dimeth yl-fluorene and diphenylamino groups Is a hydrocarbon group of 10 to 60 carbon atoms (wherein one or more compounds are linked to each other);

B is an absent; Or heavy hydrogen, substituted with an alkyl group of C1 ~ C10 substituted or unsubstituted alkyl, phenyl, C1 ~ C10 of phenyl, _{naphthyl, Si (CH) 3, CF} 3, substituted or unsubstituted alkoxy of C1 ~ C10, D Phenyl, pyridyl, pyrimidine, triazine, naphthalene, and the like substituted or unsubstituted with at least one member selected from the group consisting of benzofuran, dibenzothiophene, and a carbazole group (substituted or unsubstituted with a phenyl group or a biphenyl group) Tetrazolene, triphenylphosphine oxide, tetraphenylmethane, or -N (Ar1) -tetrahydronaphthalene, or a substituted or unsubstituted aliphatic hydrocarbon group such as a benzene ring, a benzene ring, a dibenzofuran, a dibenzothiophene, a carbazole, a fluorene, a phenanthrene, an anthracene, a benzoanthracene, a triphenylene, ) (Ar2);

Wherein Ar1 or Ar2 are, each independently, CF _3, CN, OCH _3, substituted or unsubstituted alkyl group and a phenyl group of C1 ~ C10 unsubstituted phenyl, biphenyl, naphthyl, pyridine, fluorene, dibenzofuran, or di Benzothiophene group.

More preferably,

Wherein L1, L2, L3 and L4 are each independently selected from the following chemical structural formulas

B and Ar1, Ar2, Ar3 and Ar4 may each independently be selected from the following chemical structural formulas:

In the above chemical formula,

, 또는

이며;X is, each independently, CH, CD, CF, CCN , COCH 3, CCH 3, CCH (CH 3) 2, CC (CH 3) 3, C (CH 2) n CH 3, CCF 3, N,

, or

;

F is CH ₂ , C (CH ₃ ) ₂ , C (CH ₂ CH ₃ ) ₂ , C (CF ₃ ) ₂ , O, or S;

일 수 있다.
G is CH ₂ , C (CH ₃ ) ₂ , C = O, O, S, SO ₂ , Se or

Lt; / RTI >

Even more preferably,

The organic compound of Formula 1 may be selected from the following Formulas 2 to 41:

In the above Chemical Formulas 2 to 41,

, 또는

이며;X is CH, CD, CF, CCN, COCH 3, CCH 3, CCH (CH 3) 2, CC (CH 3) 3, C (CH 2) n CH 3, CCF 3, N,

, or

;

Y and Z are each independently absent, a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and at least one of Y and Z is absent;

R1 and R2 are not present when Y is absent and R3 and R4 are absent when Z is absent; R1, R2, R3 and R4 are each independently absent or C1-C10 alkyl;

m and n are each independently an integer of 0 to 3;

o and p are each independently an integer of 1 to 3;

K is, independently of each other, an absent or carbon atom;

A 1, A 2, A 3, A 4, A 5, A 6, A 7 and A 8 are each independently a carbon atom or a nitrogen atom;

Ar9, Ar10, Ar11 and Ar12 each independently represent a non-existent; Or heavy _{hydrogen, Si (CH) 3, CF} 3, substituted or unsubstituted of C1 ~ C10 substituted or unsubstituted alkoxy, C1 ~ C10 of ring-substituted alkyl, phenyl, pyridyl, -N (Ar1) (Ar2) , dibenzo Substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, furanyl, or dibenzothiophenyl,

A substituted or unsubstituted C1 to C10 alkyl, phenyl, pyridine, pyrimidine, triazine, naphthalene, dibenzofuran, dibenzothiophene, carbazole, fluorene, phenanthrene, anthracene, benzoanthracene, triphenylene, tetraphenylene, tetra Phenyl silane, triphenylphosphine oxide, tetraphenylmethane, quinoline, isoquinoline, phenanthridine, or -N (Ar1) (Ar2);

L1, L2, L3 and L4 each independently represent a single bond; (Phenyl, anthracenyl, naphthalenyl, 9,9-dimethy-fluorenyl, and diphenylamino groups) substituted with one or more substituents selected from the group consisting of phenyl, biphenylene, naphthalene, anthracene, carbazole, pyridine, pyrimidine, A hydrocarbon group having 10 to 60 carbon atoms in which at least one compound selected from the group consisting of R < 1 >

Wherein E is composed of a _{phenyl, Si (CH) 3, CF} 3, and a substituted or unsubstituted alkoxy of C1 ~ C10 substituted with an alkyl group of heavy hydrogen, substituted or unsubstituted of C1 ~ C10 unsubstituted alkyl, phenyl, C1 ~ C10 Substituted or unsubstituted with one or more substituents selected from the group consisting of

And examples thereof include phenyl, biphenyl, pyridine, pyrimidine, triazine, naphthalene, dibenzofuran, dibenzothiophene, carbazole, fluorene, phenanthrene, anthracene, benzoanthracene, triphenylene, tetraphenylene, (Wherein at least one compound selected from the group consisting of phenyl, anthracene, naphthalene, 9,9-dimeth yl-fluorene, and diphenylamino groups is connected to each other) Lt; / RTI >

B is an absent; Or heavy hydrogen, substituted with an alkyl group of C1 ~ C10 substituted or unsubstituted alkyl, phenyl, C1 ~ C10 of phenyl, _{naphthyl, Si (CH) 3, CF} 3, substituted or unsubstituted alkoxy of C1 ~ C10, D Benzothiophene, benzofuran, and dibenzothiophene. The substituted or unsubstituted < RTI ID = 0.0 >

And examples thereof include phenyl, pyridyl, pyrimidine, triazine, naphthalene, dibenzofuran, dibenzothiophene, carbazole, fluorene, phenanthrene, anthracene, benzoanthracene, triphenylene, tetraphenylene, Phosphine oxide, tetraphenylmethane, or -N (Ar1) (Ar2);

Ar 1 and Ar 2 are each independently selected from the group consisting of CF ₃ , CN, OCH ₃ , substituted or unsubstituted alkyl of C1-C10 and substituted or unsubstituted

Phenyl, biphenyl, naphthyl, pyridine, fluorene, dibenzofurane, or dibenzothiophene group.

The organic compound of the present invention can be used as a material for all organic electroluminescence devices, and in particular, can be used as a material for a light emitting layer material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, an electron transporting layer material, Lt; RTI ID = 0.0 > and / or < / RTI > layer materials.

The light emitting layer material may be a phosphorescent green host material, a phosphorescent dopant material, a phosphorescent blue host material, a fluorescent blue dopant material, a fluorescent blue host material, a fluorescent green dopant material, or a fluorescent green host material, no.

The present invention has developed an organic luminescent compound, particularly an acridone derivative, to form various organic layers such as an electron transport layer (ETM), a light emitting layer (EML) and a hole transport layer (HTM) And to develop materials that can maximize their ability as an OLED material and improve performance such as efficiency and drive voltage reduction.

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 photovoltaic compound used in the organic photonic device of the present invention may have the structures of Formulas (1) to (1614) of the following [first group (s)] But are not limited to:

[First group (group)]

 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 electroluminescent 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. As the hole injection layer material, the organic compound of the present invention can be used. In addition, copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA) , 4 ', 4 "-tris (3-methylphenylamino) phenoxybenzene (m-MTDAPB), and starburst type amines 4,4' TCTA), 4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA) or IDE406 available from Idemitsu have.

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 organic compound of the present invention can be used as the hole transport layer material, and besides, bis (N- (1-naphthyl-n-phenyl)) benzidine (? -NPD), N, (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl- - 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 compound of the present invention can be used as a light emitting host material among the light emitting layer materials used, and further, tris (8-hydroxyquinolinolato) aluminum (Alq3) (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), spiro Spiro) material, spiro-DPVBi (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.

The compound of the present invention can be used as a dopant which can be used together with a light emitting host among the light emitting layer materials, IDE102 and IDE105 available as a fluorescent dopant from Idemitsu and phosphorescent dopants such as tris (2- Iridium (III) (Ir (ppy) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinate-N, C-2 '] picolinate (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. At this time, the electron transport layer material used may be an organic compound of the present invention, and tris (8-hydroxyquinolinolato) aluminum (Alq3) or the like may be 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 evaporation and spin coating using a hole blocking layer material by a conventional method, and the organic compound of the present invention can be used for the hole blocking layer material. In addition, (8-hydroxy Quinolinolato) lithium (Liq), bis (8-hydroxy-2-methylquinolinonato) -aluminum biphenoxide (BAlq), bathocuproine (BCP) and LiF .

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. As the electron injection layer material used herein, the organic compound of the present invention may be used. In addition, materials such as LiF, Liq, Li2O, BaO, NaCl, and CsF may 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 which can transmit 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 injection layer / electron transporting layer / hole blocking layer / light emitting layer / hole transporting layer / hole injecting layer / anode.

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.

Synthesis of Compound [78]

Preparation of compound [78]

In a 2 L reaction flask, 10.0 g (51.2 mmol) of acridone, 24.5 g (61.5 mmol) of compound [78-1], 1 g (5.1 mmol) of copper iodide (CuI) and 10.7 g ) And 0.2 g (1.0 mmol) of dipivaloid methane are dissolved in 550 ml of dimethylformamide, and the mixture is refluxed and stirred for 24 hours. After completion of the reaction, slowly cool to room temperature and extract with ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to give 15.2 g (58%) of the desired compound [78].

^{1 H NMR (300 MHz, THF} ): δ 8.75 (d, 1H), 8.14 ~ 7.87 (m, 4H), 7.77 ~ 7.40 (m, 8H), 7.61 ~ 7.45 (m, 5H), 7.11 (d, 2H ), 6.93-6.87 (m, 3H)

MS / FAB: 513 (M ^< ^{+ &} gt ^; ).

Synthesis of compound [241]

Preparation of intermediate compound [241-2]

In a 1 L reaction flask, 50 g (0.37 mol) of the compound [241-1] was added to the reactor together with 400 mL of methanol under a nitrogen stream, stirred at 0 ° C, 98.1 mL (2.19 mol) of cyanyl chloride was slowly added dropwise, . After completion of the reaction, neutralize with a saturated solution of sodium hydrogencarbonate, and extract with ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 49 g (88%) of intermediate compound [241-2].

^{1 H NMR (300 MHz, DMSO} ): δ 6 7.89 (d, 1H), 7.28 (t, 1H), 6.68 (t, 2H), 3.89 (s, 3H)

Preparation of intermediate compound [241-5]

In a 500 mL reaction flask, add 50 mL of dimethylformamide under a nitrogen stream, stir at 0 ° C, and add 61 mL (64 mmol) of oxalyl dichloride slowly. The mixture was slowly stirred at room temperature while warming, 50 g (26 mmol) of the compound [241-3] was added slowly, and the mixture was heated under reflux and stirred. After completion of the reaction, the reaction mixture is extracted with dichloromethane and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 23 g (42%) of intermediate compound [241-5].

^{1 H NMR (300 MHz, DMSO} ): δ 8.87 (d, 1H), 8.78 (d, 1H), 8.39 (d, 1H), 8.04 ~ 8.00 (m, 2H), 7.89 (t, 1H), 7.83 ~ 7.76 (m, 2 H)

Preparation of intermediate compound [241-7]

In a 1 L reaction flask, 15 g (70 mmol) of intermediate compound [241-5], 18.3 g (90 mmol) of intermediate compound [241-6] and 29 g (210 mmol) of potassium carbonate were dissolved in 200 mL of toluene under nitrogen flow, , And the mixture was heated and 2.4 g (2.1 mmol) of tetrakis (triphenylphosphine) palladium was added thereto at about 60 ° C, and the mixture was stirred under reflux for 21 hours. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid is extracted with dichloromethane, saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 10 g (43%) of an intermediate compound [241-7].

^{1 H NMR (300 MHz, CDCl} 3): δ 8.77 (d, 1H), 8.68 (d, 1H), 8.29 (d, 1H), 8.22 (d, 1H), 7.92 ~ 7.82 (m, 3H), 7.82 (M, 3H), 7.65 (t, IH), 7.58 (t, IH)

Preparation of intermediate compound [241-8]

In a 0.5 L reaction flask, 22 g (66 mmol) of the intermediate compound [241-7], 10 g (66 mmol) of the intermediate compound 241-2, 3 g (3.3 mmol) of tris (benzylideneacetone) dipalladium 3.8 g (6.6 mmol) of potassium carbonate, 18.2 g (130 mmol) of potassium carbonate and 200 mL of t-butanol are added and stirred. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and the reaction mixture was cooled to room temperature and extracted with ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 19 g (71%) of intermediate compound [241-8].

%); ^{1 H NMR (300 MHz, DMSO} ): δ 9.50 (s, 1H), 8.97 (d, 1H), 8.87 (d, 1H), 8.21 (d, 1H), 8.14 (d, 1H), 7.97 ~ 7.95 ( (m, 2H), 7.83-7.74 (m, 5H), 7.53-7.46 (m, 4H)

Preparation of intermediate compound [241-9]

In a 1 L reaction flask, 19 g (47 mmol) of the intermediate compound [241-8] were dissolved in 210 mL of tetrahydrofuran under a nitrogen flow, 60 mL of purified water and methanol were added thereto, and then 4.5 g (190 mmol) of lithium hydroxide was added and stirred. After completion of the reaction, the reaction mixture is concentrated under reduced pressure, then tetrahydrofuran and purified water are added thereto, and the pH is adjusted to 2 with 1N HCl, followed by extraction with saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 15 g (80%) of the intermediate compound [241-9].

^{1 H NMR (300 MHz, DMSO} ): δ 9.89 (s, 1H), 8.97 ~ 8.84 (m, 2H), 8.21 ~ 8.11 (m, 2H), 8.01 (t, 2H), 7.84 ~ 7.73 (m, 5H ), 7.51-7.46 (m, 4H), 6.90-6.86 (m, 1H)

Preparation of intermediate compound [241-10]

In a 1 L reaction flask, 15 g (37 mmol) of the intermediate compound [241-9] was charged under a nitrogen stream, and 200 g of polyphosphoric acid was added thereto mechanically, followed by heating and stirring. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then purified water was added to the ice water bath. The reaction mixture was neutralized with saturated ammonium hydroxide, and the reaction mixture was extracted with tetrahydrofuran and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 13 g (96%) of the intermediate compound [241-10].

^{1 H NMR (300 MHz, THF} ): δ 10.75 (s, 1H), 8.90 ~ 8.76 (m, 3H), 8.43 (d, 2H), 8.35 (d, 2H), 8.20 (d, 1H), 7.77 ~ 1H), 7.47 (d, 1H), 7.27 (t, 1H)

Preparation of compound [241]

(48 mmol) of intermediate compound [241-11], 1.3 g (6.8 mmol) of copper iodide and 9.0 g (64 mmol) of potassium carbonate were added to a 0.5 L reaction flask under a stream of nitrogen, ) And 2.2 mL (10 mmol) of dipivaloid methane are dissolved in 240 mL of dimethylformamide and stirred under reflux. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and extracted with tetrahydrofuran, ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to obtain 14 g (97%) of the target compound [241].

^{1 H NMR (300 MHz, THF} ): δ 8.95 (d, 1H), 8.90 (d, 1H), 8.78 (d, 1H), 8.56 (d, 1H), 8.32 (d, 1H), 8.20 (d, 1H), 8.06 (d, 1H), 7.93 (t, 1H), 7.84-7.82 (m, 2H), 7.77-7.70 (m, 4H), 7.61-7.57 , 7.01 (d, 1 H), 6.87 (d, 1 H)

MS / FAB: 449 (M ^< ^{+ &} gt ^; ).

Synthesis of Compound [255]

Preparation of intermediate compound [255-2]

40.1 g (0.15 mol) of the compound [255-1], 36.1 g (0.18 mol) of the compound [241-6] and 41.4 g (0.30 mol) of potassium carbonate were dissolved in 400 mL of 1,4-dioxane in a 1 L reaction flask under a nitrogen stream , 200 mL of purified water, and the mixture was heated, and 5.2 g (4.5 mmol) of tetrakis (triphenylphosphine) palladium was added thereto at about 60 ° C. and refluxed for 18 hours. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid is extracted with dichloromethane, saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 19 g (33%) of an intermediate compound [255-2].

^{1 H NMR (300 MHz, CDCl} 3): δ 8.63 (d, 2H), 8.31 ~ 8.28 (m, 5H), 8.05 (s, 1H), 7.68 (d, 2H), 7.58 ~ 7.60 (m, 6H)

Preparation of intermediate compound [255-3]

(50 mmol) of the intermediate compound [255-2], 8.9 g (60 mmol) of the intermediate compound [241-2], 0.22 g (1.00 mmol) of palladium acetate and 1.14 g (2.00 mmol) of aztophosphoric acid in a 0.5 L reaction flask under a nitrogen stream. , 22.4 g (68 mmol) of cesium carbonate, and 200 mL of toluene were placed, and the mixture was stirred under reflux for 18 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and the reaction mixture was cooled to room temperature and extracted with ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 19.5 g (87%) of an intermediate compound [255-3].

^{1 H NMR (300 MHz, CDCl} 3): δ 9.5 (s, 1H), 8.73 (d, 2H), 8.33 ~ 8.31 (m, 5H), 8.03 (d, 1H), 8.0 (s, 1H), 7.60 3H), 6.84 (t, IH), 3.94 (s, 3H)

Preparation of intermediate compound [255-4]

In a 1 L reaction flask, 19.5 g (0.04 mol) of the intermediate compound [255-3] was dissolved in 210 mL of tetrahydrofuran under nitrogen flow, 70 mL of purified water and methanol were added, 4.08 g (0.17 mol) of lithium hydroxide was added, Lt; / RTI > After completion of the reaction, the reaction mixture is concentrated under reduced pressure, then tetrahydrofuran and purified water are added thereto, and the pH is adjusted to 2 with 1N HCl, followed by extraction with saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 18.1 g (96%) of the intermediate compound [255-4].

^{1 H NMR (300 MHz, CDCl} 3): δ 10.41 (s, 1H), 9.5 (s, 1H), 8.73 (d, 2H), 8.33 ~ 8.31 (m, 5H), 8.03 (d, 1H), 8.0 (s, 1 H), 7.60-7.50 (m, 5H), 7.48 (d,

Preparation of intermediate compound [255-5]

18 g (0.04 mol) of the intermediate compound [255-4] was put in a 1 L reaction flask under a nitrogen stream, and 250 g of polyphosphoric acid was added thereto under mechanical stirring. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then purified water was added to the ice water bath. The reaction mixture was neutralized with saturated ammonium hydroxide, and the reaction mixture was extracted with tetrahydrofuran and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 15.7 g (91%) of the intermediate compound [255-5].

^{1 H NMR (300 MHz, THF} ): δ 9.5 (s, 1H), 8.73 (d, 2H), 8.33 ~ 8.31 (m, 5H), 8.03 (d, 1H), 8.0 (s, 1H), 7.60 ~ 7.50 (m, 5 H), 7.48 (d, 1 H), 7.41 (d, 3 H), 6.84

Preparation of compound [255]

(39 mmol) of intermediate compound [241-11], 0.7 g (3.6 mmol) of copper iodide and 6.82 g (50 mmol) of potassium carbonate were added to a 0.5 L reaction flask under a stream of nitrogen, ) And 1.5 mL (7.2 mmol) of dipivaloid methane are dissolved in 220 mL of dimethylformamide, and the mixture is refluxed and stirred for 24 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and extracted with tetrahydrofuran, ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to obtain 8.2 g (50%) of the target compound [255].

^{1 H NMR (300 MHz, THF} ): δ 9.87 (d, 1H), 8.93 (d, 1H), 8.56 (d, 1H), 8.50 (d, 4H), 8.36 (s, 1H), 7.83 (d, 2H), 7.76 (d, 1H), 7.55-7.61 (m, 10H), 7.31

MS / FAB: 501 (M ⁺ )

Synthesis of Compound [259]

Preparation of intermediate compound [259-2]

40.1 g (0.15 mol) of the compound [259-1], 36.1 g (0.18 mol) of the compound [241-6] and 41.4 g (0.30 mol) of potassium carbonate were dissolved in 410 mL of 1,4-dioxane in a 1 L reaction flask under a nitrogen stream And 180 mL of purified water, and the mixture was heated, and 5.2 g (4.5 mmol) of tetrakis (triphenylphosphine) palladium was added thereto at about 60 ° C, followed by reflux stirring for 18 hours. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid is extracted with dichloromethane, saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 17 g (30%) of an intermediate compound [259-2].

¹ H NMR (300 MHz, CDCl ₃ ):? 8.77 (d, 2H), 8.66 (d,

Preparation of intermediate compound [259-3]

(0.10 mol) of the intermediate compound [259-2], 15 g (0.10 mol) of the intermediate compound [241-2], 4.5 g (5.0 mmol) of palladium acetate and 5.7 g mmol), 27.4 g (0.2 mol) of potassium carbonate and 220 mL of tert-butyl alcohol, and the mixture is stirred under reflux. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and the reaction mixture was cooled to room temperature and extracted with ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 11.5 g (25%) of an intermediate compound [259-3]

^{1 H NMR (300 MHz, CDCl} 3): δ 9.92 (s, 1H), 8.85 ~ 8.79 (m, 6H), 8.04 (d, 1H), 7.64 ~ 7.58 (m, 7H), 7.49 ~ 7.46 (m, 3H), 6.92 (t, 1 H), 3.94 (s, 3 H)

Preparation of intermediate compound [259-4]

In a 0.5 L reaction flask, 11.5 g (25 mmol) of the intermediate compound [259-3] was dissolved in 110 mL of tetrahydrofuran under a nitrogen stream, 30 mL of purified water and methanol were added thereto, and then 2.4 g (0.10 mol) of lithium hydroxide was added and stirred. After completion of the reaction, the reaction mixture is concentrated under reduced pressure, then tetrahydrofuran and purified water are added thereto, and the pH is adjusted to 2 with 1N HCl, followed by extraction with saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 10.7 g (96%) of the intermediate compound [259-4].

^{1 H NMR (300 MHz, CDCl} 3): δ 12.25 (s, 1H), 9.97 (s, 1H), 8.73 ~ 8.66 (m, 6H), 7.98 (d, 1H), 7.73 ~ 7.69 (m, 6H) , 7.58-7.51 (m, 2H), 7.44 (d, 2H), 6.98 (t,

Preparation of intermediate compound [259-5]

In a 1 L reaction flask, 13.5 g (31 mmol) of the intermediate compound [259-4] was put under a nitrogen stream, and 140 g of polyphosphoric acid was added thereto under mechanical stirring, followed by heating and stirring for 18 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then purified water was added to the ice water bath. The reaction mixture was neutralized with saturated ammonium hydroxide, and the reaction mixture was extracted with tetrahydrofuran and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. And washed with acetone and methanol to prepare 11.1 g (86%) of the intermediate compound [259-5].

^{1 H NMR (300 MHz, THF} ): δ 9.62 (s, 1H), 9.04 (d, 1H), 8.78 (d, 4H), 8.31 (d, 1H), 7.83 ~ 7.75 (m, 5H), 7.74 ~ 7.69 (m, 4 H), 7.63 (d, 1 H), 7.36 (t, 1 H)

Preparation of compound [259]

(31 mmol) of the intermediate compound [241-11], 0.6 g (3 mmol) of copper iodide and 5.4 g (39 mmol) of potassium carbonate were added to a 0.5 L reaction flask under a nitrogen stream, , 220 ml of dimethylformamide was added, and the mixture was refluxed and stirred for 24 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and extracted with tetrahydrofuran, ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 6.6 g (51%) of the target compound [259].

^{1 H NMR (300 MHz, THF} ): δ 9.94 (s, 1H), 8.94 (d, 1H), 8.86 (d, 4H), 8.57 (d, 1H), 7.85 (t, 2H), 7.77 (t, 1H), 6.85 (d, IH), 6.85 (d, IH)

MS / FAB: 503 (M ^< ^{+ &} gt ^; ) [

Synthesis of Compound [264]

Preparation of intermediate compound [264-2]

(0.32 mol) of the compound [264-1], 40 g (0.26 mol) of the intermediate compound [241-2], 3.0 g (13.3 mmol) of palladium acetate, 7.3 g (13.3 mmol) 130 g (0.4 mol) of potassium carbonate and 500 mL of toluene were added, and the mixture was stirred under reflux. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and the reaction mixture was cooled to room temperature and extracted with ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 66 g (65%) of an intermediate compound [264-2]

^{1 H NMR (300 MHz, CDCl} 3): δ 9.50 (S, 1H), 8.32 (d, 1H), 8.02 (d, 1H), 7.66 ~ 7.53 (m, 6H), 7.41 (t, 1H), 6.92 (t, 1 H), 6.69 (m, 2 H), 3.89 (s, 3 H)

Preparation of intermediate compound [264-4]

A solution of 60 g (0.16 mol) of the compound [264-2], 36.1 g (0.2 mol) of the compound [264-3] and 27 g (0.93 mol) of potassium carbonate in 900 ml of toluene was added to a 3 L reaction flask under a nitrogen stream, Then, 3.6 g (3.1 mmol) of tetrakis (triphenylphosphine) palladium was added thereto at about 60 ° C, and the mixture was stirred under reflux for 18 hours. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid is extracted with dichloromethane, saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 46 g (55%) of an intermediate compound [264-4].

^{1 H NMR (300 MHz, CDCl} 3): δ 9.50 (s, 1H), 8.32 (d, 1H), 8.23 (s, 1H), 8.02 (d, 1H), 7.85 ~ 7.79 (m, 6H), 7.54 2H), 6.94 (s, 3H), 7.41 (m, 9H)

Preparation of intermediate compound [264-5]

In a 1 L reaction flask, 40 g (75 mmol) of the intermediate compound [264-4] was dissolved in 400 mL of tetrahydrofuran under a nitrogen stream, 100 mL of purified water and methanol were added, and 4.1 g (0.23 mol) of lithium hydroxide was added and stirred. After completion of the reaction, the reaction mixture is concentrated under reduced pressure, then tetrahydrofuran and purified water are added thereto, and the pH is adjusted to 2 with 1N HCl, followed by extraction with saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 35 g (90%) of intermediate compound [264-5].

^{1 H NMR (300 MHz, CDCl} 3): δ 10.41 (s, 1H), 9.5 (s, 1H), 8.42 (d, 1H), 8.23 (s, 1H), 7.85 ~ 7.73 (m, 7H), 7.54 2H), 7.02 (t, IH), 6.69 (m, 2H)

Preparation of intermediate compound [264-6]

30 g (60 mmol) of the intermediate compound [264-5] was placed in a 1 L reaction flask under a nitrogen stream, and 400 g of polyphosphoric acid was added thereto under mechanical stirring, followed by heating and stirring for 16 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then purified water was added to the ice water bath. The reaction mixture was neutralized with saturated ammonium hydroxide, and the reaction mixture was extracted with tetrahydrofuran and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. And washed with acetone and methanol to prepare 25 g (85%) of the intermediate compound [264-6].

^{1 H NMR (300 MHz, DMSO} ): δ 9.5 (s, 1H) 8.31 (d, 1H), 8.23 (s, 1H), 8.10 (s, 1H) 7.85 ~ 7.73 (m, 7H), 7.53 ~ 7.39 ( (m, 2H), 7.25 (m, 2H), 6.91 (t,

Preparation of compound [264]

(50 mmol) of intermediate compound [241-11], 0.7 g (3.6 mmol) of copper iodide and 8.7 g (63 mmol) of potassium carbonate were added to a 1 L reaction flask under a nitrogen stream, And 1.54 g (8.4 mmol) of dipivaloid methane are dissolved in 420 mL of dimethylformamide, and the mixture is refluxed with stirring for 24 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and extracted with tetrahydrofuran, ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 12 g (50%) of the target compound [264].

^{1 H NMR (300 MHz, DMSO} ): δ 8.23 (s, 1H), 8.10 (d, 1H), 7.85 ~ 7.73 (m, 7H), 7.53 ~ 7.39 (m, 8H), 7.25 ~ 7.20 (m, 4H ), 6.91 (t, IH), 6.81-6.73 (m, 3H), 6.63 (m, 2H)

MS / FAB: 578 (M ^< ^{+ &} gt ^; ).

Synthesis of Compound [944]

Preparation of intermediate compound [944-2]

In a 0.5 L reaction flask, 20 g (70.7 mmol) of the compound [944-1], 12.8 g (84.8 mmol) of the intermediate compound [241-2], 0.32 g (1.4 mmol) of palladium acetate, 2.1 g ), Cesium carbonate (35.6 g, 106.5 mmol) and toluene (200 mL) were added, and the mixture was stirred at 100 DEG C for 12 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and the reaction mixture was cooled to room temperature and extracted with ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified using a column chromatography method to prepare 9.5 g (44%) of an intermediate compound [944-2]

¹ H NMR (300 MHz, CDCl ₃ ):? 9.48 (s, IH), 8.52 (d, IH), 8.38 (d, IH), 7.64-7.47 , 3.83 (s, 3 H)

Preparation of intermediate compound [944-3]

In a 0.5 L reaction flask, 10 g (32.7 mmol) of the intermediate compound [944-2] was dissolved in 100 mL of tetrahydrofuran under a nitrogen flow, 30 mL of purified water and methanol were added, 3.2 g (131 mmol) of lithium hydroxide was added, do. After completion of the reaction, the reaction mixture is concentrated under reduced pressure, then tetrahydrofuran and purified water are added thereto, and the pH is adjusted to 2 with 1N HCl, followed by extraction with saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 18.3 g (48%) of intermediate compound [944-3].

^{1 H NMR (300 MHz, CDCl} 3): δ 10.13 (s, 1H), 9.47 (s, 1H), 8.63 (d, 1H), 8.47 (d, 1H), 7.71 ~ 7.59 (m, 3H), 7.27 ~ 7.13 (m, 3H)

Preparation of intermediate compound [944-4]

10 g (34.2 mmol) of the intermediate compound [944-3] was placed in a 1 L reaction flask under a nitrogen stream, and 150 g of polyphosphoric acid was added thereto under mechanical stirring, followed by heating and stirring for 12 hours. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, 400 mL of warm purified water was added to the ice water bath, neutralized with saturated ammonium hydroxide, and the reaction product was extracted with tetrahydrofuran and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 5.9 g (63%) of the intermediate compound [944-4].

^{1 H NMR (300 MHz, DMSO} ): δ 9.43 (s, 1H), 8.60 (d, 1H), 8.42 (d, 1H), 7.68 ~ 7.62 (m, 2H), 7.31 ~ 7.19 (m, 3H)

Preparation of intermediate compound [944-5]

(36.5 mmol) of the intermediate compound [944-4], 8.9 g (43.8 mmol) of the intermediate compound [244-11], 0.7 g (3.7 mmol) of copper iodide and 7.6 g And 1.1 g (1.1 mmol) of dipivaloid methane are dissolved in 120 mL of dimethylformamide, and the mixture is refluxed with stirring for 24 hours. After completion of the reaction, the reaction mixture is slowly cooled to room temperature and extracted with ethyl acetate, tetrahydrofuran and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate and hexane to give 10.7 g (70%) of the intermediate compound [944-5].

^{1 H NMR (300 MHz, THF} ): δ 8.91 (d, 1H), 8.73 (d, 1H), 8.55 (d, 1H), 8.21 (d, 1H), 8.05 (d, 1H), 7.90 (t, 1H), 7.85 (d, 1H), 7.73-7.65 (m, 4H)

Preparation of compound [944]

In a 1 L reaction flask, 10 g (28.6 mmol) of the compound [944-5], 13.3 g (31.4 mmol) of the compound [944-6], 0.7 g (0.6 mmol) of tetrakis (triphenylphosphine) palladium, 4.7 g (34.3 mmol) of distilled water, 30 mL of distilled water and 300 mL of toluene were added, and the mixture was refluxed and stirred for 24 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate and filtered. The concentrate was purified by column chromatography to obtain 7.6 g (41%) of the target compound [944].

^{1 H NMR (300 MHz, THF} ): δ 8.75 ~ 8.62 (m, 2H), 8.30 ~ 8.24 (m, 3H), 8.10 (m, 4H), 7.88 ~ 7.73 (m, 5H), 7.58 ~ 7.41 (m , 11H), 7.73-6.95 (m, 4H), 6.84 (d, 2H)

MS / FAB: 650 (M ^< ^{+ &} gt ^; ).

Hereinafter, the present invention will be described in more detail with reference to examples and comparative 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: Fabrication of Organic Electroluminescent Device

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) / Liq (30 nm) / a-NPD (30 nm) (1 nm) / Al (100 nm).

An anode was prepared by cutting Corning's 15 Ω / cm 2 (1000 Å) ITO glass substrate to a size of 25 mm × 25 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, 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) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. Liq 1 nm (electron injecting layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to produce an organic electroluminescent device as shown in Table 2. This is referred to as Comparative Sample 1.

Comparative Example 2: Fabrication of Organic Electroluminescent Device

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) / Liq (30 nm) / compound-b + compound c (30 nm) / ITO / 2-TNATA (1 nm) / Al (100 nm).

An anode was prepared by cutting Corning's 15 Ω / cm 2 (1000 Å) ITO glass substrate to a size of 25 mm × 25 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, 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,? -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) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. Liq 1 nm (electron injecting layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to prepare an organic electroluminescent device. This is referred to as Comparative Sample 2.

In the above description, the conventional well-known technique is omitted, but a person skilled in the art can easily guess, deduce and reproduce it.

Examples 1 to 5: Preparation of Organic Electroluminescent Device

In the same manner as in Comparative Example 1, except that the compounds represented by Chemical Formulas 160, 241, 256, 285 and 290 shown in the above Synthesis Example were used as the electron transport layer materials in place of the electron transport layer material d in Comparative Example 1, / 2-TNATA (80 nm) /? -NPD (30 nm) / [Compound a + Compound c (10%)] (30 nm) / Compound 160, 241, 256, 285, 290 ) / Al (100 nm). These are referred to as Samples 1 to 5, respectively.

Evaluation Example 1: Evaluation of luminescence characteristics of Comparative Samples 1 and 2 and Samples 1 to 5

The emission luminance, the luminous efficiency and the emission peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 1 and 2 and Samples 1 to 5, (Group)]. The samples showed green emission peak values in the range of 513-515 nm.

[Second group (group)]

Samples 1 to 5 exhibited improved luminescence characteristics as compared to Comparative Samples 1 and 2 as shown in the above [second group (group)].

Evaluation Example 2: Evaluation of life characteristics of Comparative Samples 1, 2 and Samples 1 to 5

The comparative samples 1 and 2 and the samples 1 to 5 were measured for time to reach 97% on the basis of 3000 nits using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following [ (Group)].

[Group 3]

 Samples 1 to 5 exhibited improved lifespan characteristics as compared to Comparative Samples 1 and 2, as shown in the [third set of group (s)] above.

Examples 6 to 10: Preparation of Organic Electroluminescent Device

Except that the compounds 62, 64, 92, 103 and 265 represented by the chemical formulas 62, 64, 92, 103 and 265 described in the above Synthesis Examples were respectively used as the phosphorescent green host in Comparative Example 1 (30 nm) / [Compound 62, 64, 92, 103, 265 + Compound c (10%)] (30 nm) /? -NPD An organic electroluminescent device having a structure of Alq ₃ (30 nm) / Liq (1 nm) / Al (100 nm) is manufactured. These are referred to as Samples 6 to 10, respectively.

Evaluation Example 3: Evaluation of luminescence characteristics of Comparative Samples 1 and 2 and Samples 6 to 10

The emission luminance, the luminous efficiency, and the emission peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 1 and 2 and Samples 6 to 10, (Group)]. The samples showed green emission peak values in the range of 513-515 nm.

[Group 4]

Samples 6 to 10 exhibited improved luminescence characteristics as compared to Comparative Samples 1 and 2, as shown in the [fourth set of group (s)] above.

Evaluation Example 4: Evaluation of life characteristics of Comparative Samples 1, 2 and Samples 6 to 10

The comparative samples 1 and 2 and the samples 6 to 10 were measured for time to reach 97% of life on the basis of 3000 nits using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following [ (Group)].

[Fifth group (group)]

Samples 6 to 10 showed improved lifespan characteristics as compared to Comparative Samples 1 and 2, as shown in the [fifth set of group (s)] above.

Comparative Example 3: Fabrication of organic electroluminescent device

A compound represented by the following formula (a) is used as a fluorescent blue host material, and a compound b represented by the following formula (b) is used as a fluorescent blue dopant substance and 2-TNATA (4,4 ' -naphthalen-2-yl) -N-phenylamino) -triphenylamine was used as a hole injection layer material and α-NPD (N, N'-di (naphthalene- (30 nm) / a-NPD (30 nm) / compound a + compound b (30 nm) / Alq3 (30 nm) / a-NPD was used as a hole transporting layer material, and an organic electroluminescent device having the following structure was manufactured: ITO / 2- LiF (1 nm) / Al (100 nm).

An anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate into 50 mm × 50 mm × 0.7 mm size, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, Washed and used. 2-TANATA 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,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound (a) represented by Formula (a) and compound (b) represented by Formula (b) (5% doped) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 1 nm (electron injection layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to produce the following organic electroluminescent device. This is referred to as Comparative Sample 3.

Example  11 to 15: The organic electroluminescent device  Produce

Except that the compound represented by the chemical formulas 386, 462, 590, 703, and 724 described in the above Synthesis Example was used as the light-emitting layer blue fluorescent dopant material, instead of Compound b as the light emitting layer fluorescent blue dopant material, (30 nm) / Alq3 (30 nm) / [compound a + fluorescent blue dopant compound 386, 462, 590, 703, 724 (5%)]] in the same manner as in Comparative Example 3 An organic electroluminescent device having a structure of (30 nm) / LiF (1 nm) / Al (100 nm) was manufactured. These are referred to as Samples 11 to 15, respectively.

Evaluation Example 5: Evaluation of luminescence characteristics of Comparative Sample 3 and Samples 11 to 15

The emission luminance, the luminous efficiency and the emission peak were evaluated on the basis of 10 mA / cm ² using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for the comparative sample 3 and the samples 11 to 15, Are shown in the following [sixth group (group)]. The samples showed blue emission peak values in the range of 448 to 461 nm.

[Group 6]

Samples 11 to 15 exhibited improved luminescence characteristics as compared to Comparative Sample 3, as shown in the above [sixth group (group)].

Evaluation Example 6: Evaluation of life characteristics of Comparative Sample 3 and Samples 11 to 15

The comparative sample 3 and the samples 11 to 15 were measured for time to reach 97% on the basis of 700 nits using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following [ Group)].

[Group 7]

Samples 11 to 15 showed improved lifespan characteristics as compared to Comparative Sample 3, as shown in [Seventh Set Group (s)] above.

Examples 16 to 20: Preparation of organic electroluminescent device

Except that the compound represented by the chemical formulas (874), (915), (938), (999) and (1028) shown in the above synthesis example was used as the blue host material for the light emitting layer (30 nm) / [alpha] -NPD (30 nm) / [fluorescent blue host compound 874, 915, 938, 999, 1028 + compound b (5%)] (30 nm) / Alq3 ) / LiF (1 nm) / Al (100 nm). These are referred to as Samples 16 to 20, respectively.

Evaluation Example 7: Evaluation of luminescence characteristics of Comparative Sample 3 and Samples 16 to 20

The emission luminance, the luminous efficiency, and the emission peak were evaluated on the basis of 10 mA / cm ² using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for the comparative sample 3 and the samples 16 to 20, Is shown in the following [Group 8]. The samples showed blue emission peak values in the range of 448 to 461 nm.

[Group 8]

Samples 16 to 20 exhibited improved luminescence properties as compared to Comparative Sample 3, as shown in the above [Group 8].

Evaluation Example 8: Evaluation of life characteristics of Comparative Sample 3 and Samples 16 to 20

Comparative sample 3 and samples 16 to 20 were measured for time to reach 97% on the basis of 700 nits using a LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following [ Group)].

[Ninth Major Group (Group)]

Samples 16 to 20 exhibited improved lifespan characteristics as compared to Comparative Sample 3, as shown in the above [9th set group (s)].

Comparative Example 4: Fabrication of organic electroluminescent device

Wherein the compound represented by the following formula (a) is used as a fluorescent green host material, and the compound represented by the following formula (c) is used as a fluorescent green dopant substance and 2-TNATA (4,4 ' 2-yl) -N-phenylamino) -triphenylamine was used as a hole injection layer material and α-NPD (N, N'-di (naphthalene- ITO / 2-TNATA (80 nm) /? -NPD (30 nm) / Compound a + Compound c (30 nm) / Alq ₃ (30 nm) was used as a material to prepare an organic electroluminescent device having the following structure: ) / Liq (1 nm) / Al (100 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 25 mm × 25 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 (a) and a compound represented by the formula (c) (doping ratio: 3%) 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. Liq 1 nm (electron injection layer) and Al 100 nm (cathode) are sequentially vacuum-deposited on the electron transport layer to produce an organic electroluminescent device. This is referred to as Comparative Sample 1.

Comparative Example 5: Fabrication of organic electroluminescent device

Wherein the compound represented by the following formula (b) is used as a fluorescent green host material and the compound represented by the following formula (c) is used as a fluorescent green dopant, and 2-TNATA (4,4 ' -yl) -N-phenylamino) -triphenylamine was used as a hole injection layer material and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) (30 nm) /? -NPD (30 nm) / compound b + compound c (30 nm) / Alq ₃ (30 nm) Liq (1 nm) / Al (100 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 25 mm × 25 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,? -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) (doping ratio: 3%) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. 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. Liq 1 nm (electron injecting layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to prepare an organic electroluminescent device. This is referred to as Comparative Sample 5.

Examples 21 to 25: Preparation of organic electroluminescent device

In the same manner as in Comparative Example 4 except that the compound represented by the chemical formulas 52, 131, 164, 211, and 245 disclosed in the above Synthesis Example was used as a fluorescent green host, (30 nm) / Alq ₃ (30 nm) / Liq (30 nm) / [Compound 52, 131, 164, 211, 245 + Compound c (3%)] An organic electroluminescent device having a structure of (1 nm) / Al (100 nm) was prepared. These are referred to as Samples 21 to 25, respectively.

Evaluation Example 9: Evaluation of luminescence characteristics of Comparative Samples 4 and 5 and Samples 21 to 25

The emission luminance, the luminous efficiency, and the emission peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 4 and 5 and Samples 21 to 25, (Group)]. The samples showed green emission peak values in the range of 513-515 nm.

[Group 10]

Samples 21 to 25 exhibited improved luminescence characteristics as compared to Comparative Samples 4 and 5 as shown in the above [10th set group (group)].

Evaluation Example 10: Evaluation of life characteristics of Comparative Samples 4, 5 and Samples 21 to 25

The comparative samples 4 and 5 and the samples 21 to 25 were measured for time to reach 97% on the basis of 3000 nits by using an LTS-1004AC life measuring device manufactured by ENC technology, respectively. The results are shown in the following [ (Group)].

[Eleventh typing group (group)]

 Samples 21 to 25 exhibited improved lifespan characteristics as compared to Comparative Samples 4 and 5, as shown in [11th set group (s)].

Examples 26 to 30: Manufacture of organic electroluminescent device

In Comparative Example 4, except that the compounds represented by Chemical Formulas 1043, 1049, 1053, 1057, and 1059 shown in the synthesis examples were used as fluorescent green dopants instead of the fluorescent green dopant substance c, (30 nm) / [alpha] -NPD (30 nm) / [compound a + compounds 1043, 1049, 1053, 1057, 1059 (3%)] (30 nm) / Alq ₃ An organic electroluminescent device having a structure of Liq (1 nm) / Al (100 nm) was produced. These are referred to as samples 26 to 30, respectively.

Evaluation example 11: Evaluation of luminescence characteristics of comparative sample 4 and samples 2C6 to C30

The emission luminance, the luminous efficiency and the emission peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for the comparative sample 4 and the samples 26 to 30, )]. The samples showed green emission peak values in the range of 513-515 nm.

[Group 12]

Samples 26 to 30 exhibited improved luminescence properties as compared to Comparative Sample 4, as shown in [Twelfth Set Group (s)] above.

Evaluation Example 12: Evaluation of life characteristics of Comparative Sample 4 and Samples 26 to 30

The comparative sample 4 and samples 26 to 30 were measured for time to reach 97% of life on the basis of 3000 nits using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following [ Group)].

[Group 13]

Samples 26 to 30 exhibited improved lifetime characteristics as compared to Comparative Sample 4, as shown in [Group 13 of the above table].

Claims (11)

The following compounds 103, 108, 116, 244, 253 to 259, 261 to 266, 268 to 274, 276 to 307, 310 to 312, 321 to 328, 352, 355 to 357, 404 to 420, 423 to 426, 442, 445 to 447, 489, 490, 492-493, 744, 749, 757, 765, 837 to 847, 849 to 852, 854 to 857, 932 to 1039, 1165 to 1168, 1170 to 1173, 1243, 1261, 1269 to 1271, 1468 to 1490, 1554, 1555, 1558, 1563 and 1566. [

delete delete delete delete The method according to claim 1,
The organic compound may be at least one selected from the group consisting of a light emitting layer material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, an electron transporting layer material, an electron blocking layer material and a hole blocking layer material in a material for an organic electroluminescence device Wherein the organic compound is an organic compound. The method according to claim 6,
Wherein the light emitting layer material is a phosphorescent green host material, a phosphorescent dopant material, a phosphorescent blue host material, a fluorescent blue dopant material, a fluorescent blue host material, a fluorescent green dopant material, or a fluorescent green host material. An organic electroluminescent device in which a single layer or a plurality of organic thin film layers including 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 compound of claim 1 singly or in combination of two or more kinds. 9. The method of claim 8,
Wherein the organic compound of claim 1 is contained in at least one of a light emitting layer material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, an electron transporting layer material, an electron blocking layer material and a hole blocking layer material Light emitting element. 10. The method of claim 9,
Wherein the light emitting layer material is selected from a phosphorescent green host material, a phosphorescent dopant material, a phosphorescent blue host material, a fluorescent blue dopant material, a fluorescent blue host material, a fluorescent green dopant material, and a fluorescent green host material. An electroluminescent device. 11. The method according to any one of claims 8 to 10,
The organic electroluminescent device
Wherein the anode, the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron injection layer, and the cathode are laminated in this order.

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