KR20130110051A - Carbazole derivatives and organoelectro luminescent device using the same - Google Patents

Abstract

PURPOSE: A carbazole derivative is provided to drive an organic electroluminescent device at low voltage and to improve brightness when the derivative is used in an organic layer of the organic electroluminescent device, thereby improving economic efficiency. CONSTITUTION: A carbazole derivative is denoted by chemical formula 1. An organic electroluminescent device comprises a first electrode, a second electrode, and one or more organic layers between the first and second electrodes. The organic layers contain the carbazole derivative of chemical formula 1. The organic layers are selected among a hole injection layer, a hole transport layer, a functional layer with hole injecting and transporting functions, a light emitting layer, an electrode transport layer, and an electron injection layer. The light emitting layer contains one or more host compounds and one or more dopant compounds. The host compound is a carbazole derivative of chemical formula 1.

Description

Carbazole derivatives and organoelectroluminescent device using the same

The present invention relates to a novel carbazole derivative and an organic electroluminescent device comprising the same.

An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When a voltage is applied between the two electrodes in the structure of the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

Organic electroluminescent devices have been increasingly applied to display and illumination fields of various electronic products. However, efficiency and lifetime characteristics are limiting the expansion of application fields. In order to improve efficiency and lifetime characteristics, Many studies are under way.

In particular, in terms of materials, the host-dopant system is mainly adopted as a method for maximizing luminous efficiency, and the dopant as a luminescent material is a phosphorescent material, and CBP (4,4'-) as a host to maximize the luminescent properties of the dopant. N, N'-dicarbazolbiphenyl) and substances in which various substituents are introduced into carbazole (Japanese Patent Publication 2008-214244, Japanese Patent Publication 2003-133075) are known, but further improvement in efficiency and life characteristics is required. .

The present invention is to provide a novel carbazole derivative and an organic light emitting device capable of low voltage driving, and excellent in luminous efficiency and lifespan characteristics.

The present invention provides a carbazole derivative of the following [Formula 1] to solve the above problems.

[Formula 1]

In the above formula (1)

,

,

및

중에서 선택되고, Ar₁은 치환 또는 비치환된 탄소수 6-50의 아릴기 또는 치환 또는 비치환된 탄소수 2-50의 헤테로아릴기이며,R₁ 내지 R₅는 각각 독립적으로 수소원자, 중수소 원자, 치환 또는 비치환된 탄소수 1-50의 알킬기 및 치환 또는 비치환된 탄소수 6-50의 아릴기 중에서 선택된다.A ring or B ring each independently

,

,

And

Ar ₁ is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, R ₁ To R ₅ are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In addition, Ar ₁ , R ₁ to R ₅ are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxyl group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, or an alkyl having 1 to 40 carbon atoms. Amino group, arylamino group of 6-40 carbon atoms, heteroarylamino group of 3-40 carbon atoms, alkylsilyl group of 1-40 carbon atoms, arylsilyl group of 6-40 carbon atoms, aryl group of 6-40 carbon atoms, 3-40 carbon atoms It may be further substituted by one or more substituents selected from the group consisting of an aryloxy group, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus, and boron.

On the other hand, the present invention provides an organic light emitting device having an anode, a cathode and a layer comprising a carbazole derivative represented by the above [Formula 1] between the anode and the cathode.

According to an embodiment of the present invention, the organic light emitting device is selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode The above layer may be further included, and the carbazole derivative is preferably included in the light emitting layer between the anode and the cathode.

In addition, the organic light emitting display device according to the present invention can be used for a display device, a display device and a monochrome or white lighting device.

When the carbazole derivative according to the present invention is used in the organic material layer of the organic light emitting device, the organic light emitting device is driven at low voltage and the luminance is improved, which is very economical.

1 is a cross-sectional view showing a laminated structure of an organic light emitting display device according to a preferred embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

Carbazole derivatives according to the invention is characterized in that represented by the following [Formula 1].

[Formula 1]

In the above formula (1)

,

,

및

중에서 선택된다.A ring or B ring each independently

,

,

And

.

Ar ₁ is a substituted or unsubstituted aryl group having 6-50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2-50 carbon atoms.

R ₁ To R ₅ are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

Ar ₁ , R ₁ to R ₅ are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an alkylamino group having 1 to 40 carbon atoms, Arylamino group having 6 to 40 carbon atoms, heteroarylamino group having 3 to 40 carbon atoms, alkylsilyl group having 1 to 40 carbon atoms, arylsilyl group having 6 to 40 carbon atoms, aryl group having 6 to 40 carbon atoms, aryl jade having 3 to 40 carbon atoms And may be further substituted by one or more substituents selected from the group consisting of a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus, and boron.

According to an embodiment of the present invention, the carbazole derivative may be one of the compounds represented by [Formula 2] to [Formula 6].

[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

[Formula 1-5] [Formula 1-6]

[Formula 1-7] [Formula 1-8]

[Formula 1-9] [Formula 1-10]

[Formula 1-11] [Formula 1-12]

[Formula 1-13]

In [Formula 1-1] to [Formula 1-13],

Ar ₁ to Ar ₃ are each independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

R ₁ And R ₂ are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

Ar ₁ to Ar ₃ , R ₁ to R ₂ are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, or an alkyl group having 1 to 40 carbon atoms. Alkylamino group, arylamino group of 6-40 carbon atoms, heteroarylamino group of 3-40 carbon atoms, alkylsilyl group of 1-40 carbon atoms, arylsilyl group of 6-40 carbon atoms, aryl group of 6-40 carbon atoms, 3-40 carbon atoms It may be further substituted by one or more substituents selected from the group consisting of an aryloxy group, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus, and boron.

On the other hand, the aryl group contained in the carbazole derivative according to the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members In addition, when there is a substituent in the aryl group may be fused with a neighboring substituent (fused) with each other to further form a ring.

Specific examples of such aryl include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4- Ethyl biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, pyre And aromatic groups such as a silyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like.

Further, at least one hydrogen atom of the aryl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH (R), -N (R ') (R ") , R 'and R "are independently of each other an alkyl group having 1 to 10 carbon atoms, in this case referred to as" alkylamino group "), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, 1 to 24 carbon atoms Alkyl group, C1-C24 halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group It may be substituted with a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms.

Meanwhile, the heteroaryl group included in the carbazole derivative according to the present invention may be any substituent selected from [Formula 1] to [Formula 6].

[Structural formula 1] [Structural formula 2] [Structural formula 3]

[Structural formula 4] [Structural formula 5] [Structural formula 6]

In [Formula 1] to [Formula 6], T ₁ to T ₈ are the same or different and independently from each other, C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ), It is any one selected from O and S.

In addition, the R ₃₁ to R ₄₄ Are each the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted cyclo group having 3 to 30 carbon atoms An alkyl group, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, and each of [Formula 1] To [Formula 6] to R ₃₁ to R ₄₄ One may form a single bond by combining with nitrogen contained in [Formula 1].

In addition, the above-mentioned [formula 3] may include a compound represented by [formula 3-1] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the above structural formula 3-1, T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

According to one embodiment of the present invention, the above Structural Formulas 1 to 6 can be selected from the following Structural Formula 7.

[Structural Formula 7]

In the above formula 7,

X is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon atom 5 to 50 aryl groups, substituted or unsubstituted, heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, m is an integer of 1 to 11, when m is 2 or more The plurality of Xs may be the same or different from each other. In addition, one of the X _m may form a single bond by combining with nitrogen included in [Formula 1].

In the present invention, the 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C1 An alkenyl group having 24 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or 2 to 24 carbon atoms 24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 heteroarylaryl group, C1-C24 alkylsilyl group, C1-C24 It means to be substituted with one or more substituents selected from the group consisting of arylsilyl group of 24 to 24, aryloxy group having 1 to 24 carbon atoms, germanium, phosphorus, boron.

The carbon number range of the alkyl group or aryl group in the above "substituted or unsubstituted C1-C30 alkyl group" and "substituted or unsubstituted C5-C50 aryl group" Quot; means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is regarded as unsubstituted. For example, a phenyl group substituted with a butyl group in the para position means a aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

According to a preferred embodiment of the present invention, the carbazole derivative represented by [Formula 1] may be selected from the compounds represented by the following [Formula 2] to [Formula 103], which is a carbazole derivative according to the present invention It is merely illustrative, and the scope of the present invention is not limited thereto.

[Formula 2] [Formula 3] [Formula 4] [Formula 5]

[Formula 6] [Formula 7] [Formula 8] [Formula 9]

[Formula 10] [Formula 11] [Formula 12] [Formula 13]

[Formula 14] [Formula 15] [Formula 16] [Formula 17]

[Formula 18] [Formula 19] [Formula 20] [Formula 21]

[Formula 22] [Formula 23] [Formula 24] [Formula 25]

[Formula 26] [Formula 27] [Formula 28] [Formula 29]

[Formula 30] [Formula 31] [Formula 32] [Formula 33]

[Formula 34] [Formula 35] [Formula 36] [Formula 37]

[Formula 38] [Formula 39] [Formula 40] [Formula 41]

[Formula 42] [Formula 43] [Formula 44] [Formula 45]

[Formula 46] [Formula 47] [Formula 48] [Formula 49]

[Formula 50] [Formula 51] [Formula 52] [Formula 53]

[Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Formula 58] [Formula 59] [Formula 60] [Formula 61]

[Formula 62] [Formula 63] [Formula 64] [Formula 65]

[Formula 66] [Formula 67] [Formula 68] [Formula 69]

[Formula 70] [Formula 71] [Formula 72] [Formula 73]

[Formula 74] [Formula 75] [Formula 76] [Formula 77]

[Formula 78] [Formula 79] [Formula 80] [Formula 81]

[Formula 82] [Formula 83] [Formula 84] [Formula 85]

[Formula 86] [Formula 87] [Formula 88] [Formula 89]

[Formula 90] [Formula 91] [Formula 92] [Formula 93]

[Formula 94] [Formula 95] [Formula 96] [Formula 97]

[Formula 98] [Formula 99] [Formula 100] [Formula 101]

[Formula 102] [Formula 103]

In addition, the present invention is a first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer may include at least one organic light emitting compound represented by the above [Formula 1].

The organic layer containing the organic luminescent compound of the present invention may include at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, have. In this case, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is composed of a host and a dopant, the organic light emitting compound of the present invention may be used as a host.

In the present invention, a dopant material may be used for the light emitting layer in addition to the host. When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

In addition, in the present invention, a known electron transport material can be used as the electron transport layer material, which functions to stably transport electrons injected from an electron injection electrode (cathode). Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- olate: Bebq2), ADN, [Compound 201], [Compound 202], oxadiazole derivative PBD, BMD, BND and the like may be used.

TAZ BAlq

[Compound 201] [Compound 202] BCP

Further, the electron transporting layer used in the present invention can be used as the organometallic compound represented by the following formula (C) alone or in combination with the electron transporting layer material.

≪ RTI ID = 0.0 &

In [Formula C],

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond.

M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination bond with M, O is oxygen, A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkyl, An alkenyl group, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having a hetero atom O, N, or S.

In addition, when M is one metal selected from alkali metals, m = 1, n = 0, and when M is one metal selected from alkaline earth metals, m = 1, n = 1, or m = 2 and n = 0, and when M is boron or aluminum, any one of m = 1 to 3, and n satisfies m + n = 3 as any one of 0 to 2.

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

In addition, each Y is the same or different, and may be any one selected from the following [formula C1] to [formula C39] independently of each other.

[Structure C1] [Structure C2] [Structure C3]

[Structure C4] [Structure C5] [Structure C6]

[Structure C7] [Structure C8] [Structure C9] [Structure C10]

[Formula C11] [Formula C12] [Formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structure C17] [Structure C18] [Structure C19] [Structure C20]

[Structure C21] [Structure C22] [Structure C23]

[Structure C24] [Structure C25] [Structure C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structure C31] [Structure C32] [Structure C33]

[Structure C34] [Structure C35] [Structure C36]

[Structure C37] [Structure C38] [Structure C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

L represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aryl group having 3 to 20 carbon atoms, A heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and may be connected to an adjacent substituent by an alkylene or an alkenylene to form a spiro ring or a fused ring.

Hereinafter, the organic light emitting device of the present invention will be described with reference to FIG.

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, if necessary, the hole injection layer 30 and the electron The injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to Figure 1 with respect to the organic light emitting device and a manufacturing method of the present invention.

First, the anode 20 is formed by coating an anode electrode material on the substrate 10. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

The hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

The hole injection layer material may be used without particular limitation as long as it is commonly used in the art, for example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine)], TPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'-diamine ] Can be used.

In addition, it is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer, for example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1 -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (α-NPD) and the like can be used.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but should have an ionization potential higher than the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

As the material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, and [Chemical Formulas 101] to [107] may be used. It doesn't happen.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

Chemical Formula 101 Chemical Formula 102 Chemical Formula 103

Chemical Formula 104 Chemical Formula 105 Chemical Formula 106

Formula 107

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

In addition, the light emitting layer may be formed of a host and a dopant, and according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa.

At this time, the dopant used in the light emitting layer may be at least one compound selected from the compounds represented by the following general formulas (A-1) to (J-1).

[Formula A-1]

In the above general formula A-1,

M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag.

Further, L ₁ , L _2, and L ₃ may be any one selected from the following [formula D], which may be the same as or different from each other and independently of each other. Represents a site.

[Formula D]

In [Formula D],

R is different from or the same as each other and is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-50 aryl, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And R is independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, Which may be further substituted with one or more substituents selected from a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium, and hydrogen, and R may be linked to each adjacent substituent by alkylene or alkenylene, Aromatic ring and a monocyclic or polycyclic aromatic ring.

L represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aryl group having 3 to 20 carbon atoms, A heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and may be connected to an adjacent substituent by an alkylene or an alkenylene to form a spiro ring or a fused ring.

According to one embodiment of the present invention, the dopant represented by the above-mentioned [formula A-1] may be any one selected from the following compounds.

[Formula B-1]

In [Formula B-1],

M ^A1 represents the same metal ion as defined in the above-mentioned [formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represent a carbon atom or a nitrogen atom, Y ^A12, Y ^A13, Y ^A16 and Y ^A17 each independently represents a substituted or unsubstituted carbon atoms, a substituted or unsubstituted nitrogen atom, an oxygen atom, a sulfur atom, the L ^A11 , L ^A12 , L ^A13 and L ^A14 each represent a linking group such as L ₁ , L ₂ and L ₃ defined in the above [formula A-1], and Q ^A11 and Q ^A12 represent an atom bonding to M ^A1 . ≪ / RTI >

According to one embodiment of the present invention, the compound represented by the above-mentioned [formula B-1] may be any one selected from the following compounds.

[Formula C-1]

In [Formula C-1],

M ^B1 is the represents the same metal ion as defined from the following formula ^{A-1], Y B11,} Y B14, Y B15 and Y ^B18 represents a carbon atom or a nitrogen atom, each independently, Y ^B12, Y ^B13, Y ^B16 and ^YB17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom, L ^B11 , L ^B12 , L ^B13 and L ^B14 represent a linking group, Q ^B11 , Q ^B12 represents a partial structure containing an atom bonding to M ^B1 .

According to one embodiment of the present invention, the compound represented by the above-mentioned [formula C-1] may be any one selected from the following compounds.

[Formula D-1]

In [Formula D-1],

M ^C1 represents a metal ion as defined in the above-mentioned [formula A-1], R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent which is mutually connected to form a 5-membered ring, , R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent which is mutually connected to form a 5-membered ring or a substituent which is not connected to each other, R ^C13 and R ^C14 each independently represent a hydrogen atom, G ^C11 and G ^C12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, Q ^C11 and Q ^C12 Represents a partial structure containing an atom bonding to M ^C1 .

According to one embodiment of the present invention, the compound represented by the above-mentioned [formula D-1] may be any one selected from the following compounds.

[Formula E-1]

In [Formula E-1],

M ^D1 represents a metal ion as defined in the above-mentioned [formula A-1], G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 And J ^D14 each independently represent an atomic group necessary for forming a five-membered ring, and L ^D11 and L ^D12 represent a linking group.

According to one embodiment of the present invention, the compound represented by the above-mentioned [formula E-1] may be any one selected from the following compounds.

[Formula F-1]

In [Formula F-1],

M ^E1 is above represents the same metal ion as defined from the following formula ^{A-1], J E11,} J E12 represents a group of atoms necessary haneundedo form a 5-membered ring, each ^{independently, G E11, G E12, G} E13 and G ^E14 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

According to one embodiment of the present invention, the compound represented by the above-mentioned [formula F-1] may be any one selected from the following compounds.

[General Formula G-1]

In [General Formula G-1],

M ^F1 is above represents the same metal ion as defined from the following formula ^{A-1], L F11,} L F12 and L ^F13 represents a linking group, R ^F11, R ^F12, R ^F13 and R ^F14 represents a substituent, R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be connected to each other to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. In addition, Q ^F11 and Q ^F12 represent a partial structure containing an atom bonded to M ^F1 .

According to one embodiment of the present invention, the compound represented by the above-mentioned [formula G-1] may be any one selected from the following compounds.

[Formula H-1] [Formula H-2] [Formula H-3]

In the above general formula H-1,

R ¹¹ and R ¹² are an alkyl group, an aryl group, or a heteroaryl group, which may form a fused ring with adjacent substituents, and q 11 and q 12 are integers of 0 to 4, preferably 0 to 2. When q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different.

L ¹ is a ligand which binds to platinum and is preferably a ligand capable of forming an ortho metal platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, or a halogen ligand, more preferably an ortho metal ) Ligand forming a platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

n ¹ is an integer of 0 to 3, preferably 0, m ¹ is 1 or 2, and preferably 2.

It is preferable that n ¹ and m ¹ are such that the metal complex represented by the above-mentioned [formula H-1] is a neutral complex.

In [Formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² and L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ , respectively, and q ²¹ is an integer of 0 to 2; , 0 is preferred.

In [Formula H-3],

^{R 31, n 3, m 3} , L 3 are each as defined in the ^{R 11, n 1, m 1} , L 1 and, q ³¹ represents an integer of 0-8, and 0-2 are preferred, greater than 0, desirable.

According to one embodiment of the present invention, the compounds represented by the above-mentioned [formula H-1] to [formula H-3] may be any one selected from the following compounds.

[Formula I-1]

In [Formula I-1],

Ring A, Ring B, Ring C, and Ring D represent a nitrogen-containing heterocycle in which any two rings of Rings A to D may have a substituent, and the other two rings may be an aryl ring or heteroaryl which may have a substituent Ring, ring A and ring B, ring A and ring C and / or ring B and ring D may form a condensed ring.

X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which any two of them are coordinated to a platinum atom, and the other two represent a carbon atom or a nitrogen atom.

Q ¹ , Q ² and Q ³ each independently represent a divalent atom (bond) or a bond, but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. ^{Two of} Z ¹ , Z ² , Z ³ and Z ⁴ represent coordinate bond, and the remaining two represent a covalent bond, an oxygen atom or a sulfur atom.

According to one embodiment of the present invention, the compound represented by the above-mentioned [formula I-1] may be any one selected from the following compounds.

[Formula J-1]

In [formula J-1],

M represents the same metal ion as defined in the above-mentioned [formula A-1], Ar1 represents a substituted or unsubstituted cyclic structure, and two azomethine bonds (-C = N- ), The nitrogen atom (N) binds to the M, respectively, and forms a three-dimensional ligand which is bonded at the 3-position to the M as a whole.

In Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, said R1 and R2 may mutually be same or different, and represent a substituted or unsubstituted alkyl group or an aryl group, respectively, and L represents a monodentate ligand.

M is preferably Pt, and Ar1 is preferably selected from a 5-membered ring, a 6-membered ring and condensed ring thereof.

According to one embodiment of the present invention, the compound represented by the above-mentioned [formula J-1] may be any one selected from the following compounds.

In addition to the dopant and the host, the emission layer may further include various hosts and various dopant materials.

In addition, one or more layers selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process, wherein the deposition method Means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating or the like in a vacuum or low pressure state, and the solution process is used as a material for forming each layer. It refers to a method of forming a thin film through a method such as mixing the material with a solvent and inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating and the like.

In addition, the organic light emitting display device according to the present invention can be used for a display device, a flat panel or a flexible display device and a monochrome or white lighting device.

Hereinafter, the present invention will be described in more detail with reference to the following examples, which are merely illustrative to aid the understanding of the present invention, and the scope of the present invention is not limited thereto.

Synthesis Example 1 Synthesis of <Formula 41>

Synthesis of 1- (1) 1-a

<1-a> was synthesized according to Reaction Scheme 1 below.

[Reaction Scheme 1]

<1-a>

1 L round bottom flask contains methyl aminobenzoate (21.4 ml, 165 mmol), bromo benzene (14.5 ml, 138 mmol), palladium acetate (0.62 g, 2.8 mmol), xantose (3.19 g, 5.51 mmol), cesium carbonate ( 63 g, 193 mmol) and 500 ml of toluene are added and refluxed for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and toluene was concentrated under reduced pressure to remove the solvent. The concentrated solution was subjected to column chromatography using ethyl acetate and hexane as a developing solvent, to obtain the title compound (29.3 g, yield 93.61%).

1- (2) Synthesis of 1-b

<1-b> was synthesized by the following Scheme 2.

[Reaction Scheme 2]

<1-b>

In a 1000 ml round bottom flask, <1-a> (30 g, 132 mmol) obtained from Scheme 1, 400 ml of isopropyl ether, cooled to 10 ° C., and methyl magnesium bromide (1.06 M in THF 435 ml, 462 mmol) was added dropwise for 1 hour. After refluxing for 2 hours, the reaction ends. After cooling to room temperature, 300 ml of 10% aqueous ammonium chloride solution was added thereto, stirred for 2 hours, layered to obtain an organic layer, and concentrated under reduced pressure to obtain 15 g (yield 50%) of the title compound.

1- (3) Synthesis of 1-c

&Lt; 1-c > was synthesized by the following Reaction Scheme 3.

Scheme 3

<1-c>

Dissolve <1-b> (15 g, 65 mmol) obtained in Scheme 2 in 10 ml of phosphoric acid in a 100 ml round bottom flask and react for 6 hours. After completion of the reaction, the reaction solution was poured into excess water to form a solid, which was filtered to obtain 13.5 g (yield 93.2%) of the title compound.

1- (4) Synthesis of 1-d

<1-d> was synthesized according to Scheme 4 below.

[Reaction Scheme 4]

<1-d>

After dissolving <1-c> (10 g, 48 mmol) obtained in Scheme 3 in 100 ml of methylene chloride in a 500 ml round bottom flask, cooling to 0 ° C., and adding N-bromo succinimide (18.7 g, 105 mmol) Stir for 5 hours. After completion of the reaction, the mixture was washed three times with 300 ml of water and the solvent was removed to obtain 13.2 g (yield 75.23%) of the title compound.

1- (5) Synthesis of 1-e

<1-e> was synthesized by the following Reaction Scheme 5.

[Reaction Scheme 5]

<1-e>

Magnesium (24.3 g, 0.935 mol), 1 g of iodine, and 150 ml of ether were dissolved in a 1000 ml round bottom flask, bromobenzene (155.3 g, 0.985 mol) was added thereto, and refluxed for 2 hours to prepare solution 1. Cyanuric chloride (70 g, 0.38 mol) was dissolved in 300 ml of ether in a 1 L round bottom flask, cooled to 10 ° C., and solution 1 was slowly added for 1 hour and then refluxed for 4 hours. After completion of the reaction, the solid was filtered off, and the filtrate was distilled under reduced pressure, and then recrystallized with hexane to obtain the title compound 46.1g (yield 45%).

Synthesis of 1- (6) 1-f

<1-f> was synthesized by the following Reaction Scheme 6.

[Reaction Scheme 6]

<1-f>

In a 500 ml round bottom flask, <1-d> (10 g, 27 mmol) obtained in Scheme 4 was added to 50 ml of dimethylformamide, followed by stirring. Then, 60% sodium hydride (1.3 g, 33 mmol) was added and stirred for 1 hour. <1-e> (8.8g, 33mmol) obtained from Scheme 5 was dissolved in 50ml of dimethylformamide, and then added to the reaction solution for 1 hour, followed by stirring for 5 hours. After the reaction was completed, the reaction solution was poured into 500 ml of water and filtered to obtain 14 g (yield 85.9%) of the title compound.

Synthesis of 1- (7) 1-g

<1-g> was synthesized according to the following Reaction Scheme 7.

[Reaction Scheme 7]

<1-g>

In a 500 ml round bottom flask, 2-bromonitrobenzene (20 g, 99 mmol), bispinacolato diboron (30.2 g, 119 mmol), palladium (II) chloride-1,1'-bis (diphenylphosphino) Ferrocene (2.4g, 3mmol), potassium acetate (19.4g. 198mmol) and toluene 200ml were added and refluxed for 5 hours. After completion of the reaction, the solids were filtered off, and the filtrate was concentrated under reduced pressure, followed by column separation to obtain the target product 18g (yield 73%).

Synthesis of 1- (8) 1-h

<1-h> was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

<1-h>

<1-f> (16.15 g, 27 mmol) from Scheme 6, <1-g> (16.28 g 65 mmol) from Scheme 7, potassium carbonate (22.59 g, 163 mmol), tetrakistriphenylphosphate in 250 ml round bottom flask Pinpalladium (1.58 g, 1 mmol), 20 ml of water, 50 ml of toluene and 50 ml of tetrahydrofuran were added and refluxed for 12 hours. After the reaction was completed, the resulting product was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure, and then crystals were precipitated with methanol and filtered to obtain 14 g (yield 75.9%) of the title compound.

Synthesis of 1- (9) 1-i

<1-i> was synthesized by the following Scheme 9.

Scheme 9

<1-i>

Into a 250 ml round bottom flask was added reflux with <1-h> (10 g, 15 mmol) obtained from Scheme 8, triphenylphosphine (19.2 g, 73 mmol) and 100 ml of ortho dichlorobenzene. After completion of the reaction, the reaction solution was poured into excess methanol and filtered to obtain 4.6 g (yield 50.8%) of the title compound.

Synthesis of 1- (10) <Formula 41>

<Formula 41> was synthesized by the following Scheme 10.

[Reaction Scheme 10]

&Lt; EMI ID =

In a 100 ml round bottom flask, <1-i> (4 g, 6 mmol), iodobenzene (6.6 g, 32 mmol), copper (2.46 g, 39 mmol), potassium carbonate (5.36 g, 39 mmol), Add 20 ml of sodichlorobenzene and reflux for 72 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, added with excess methanol to form a solid, and then filtered to obtain 3.0 g, (yield 60.2%).

MS (MALDI-TOF): m / z 770.3 [M] ⁺

¹³ C NMR (75 MHz, CDCl ₃ ) δ: 22.9 30.9 100.8 109.5 113.1 119.8 120.2 121.4 122.7 125.5 125.6 126.6 127.5 129.2 129.3 131.1 134.2 134.7 136.8 138.9 139.7 172.2 178.2 [54C]

Synthesis Example 2 Synthesis of <Formula 85>

Synthesis of 2- (1) <2-a>

<2-a> was synthesized according to Scheme 11 below.

[Reaction Scheme 11]

<2-a>

Synthesis was carried out in the same manner, except that methyl bromobenzoate was used instead of 2-bromonite benzene used in Scheme 7, to obtain 45.3 g (yield 74.3%) of <2-a>.

Synthesis of 2- (2) 2-b

<2-b> was synthesized according to Scheme 12 below.

[Reaction Scheme 12]

<2-b>

<1-f> (10 g, 17 mmol) from Scheme 6, <2-a> (10.51 g 40 mmol) from Scheme 11, potassium carbonate (13.86 g, 100 mmol), tetrakistriphenylphosphate in 250 ml round bottom flask 20 ml of pinpalladium (1 g, 1 mmol) water, 50 ml of toluene and 50 ml of tetrahydrofuran were added and refluxed for 12 hours. When the reaction was completed, the resulting product was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure. Then, the precipitate was precipitated using methanol and filtered to obtain 5.8 g (yield 51%) of the title compound.

Synthesis of 2- (3) 2-c

<2-c> was synthesized by the following Scheme 13.

[Reaction Scheme 13]

<2-c>

Except for <2-b> synthesized in Scheme 12 instead of <1-a> used in Scheme 2, the compound was synthesized in the same manner to obtain <2-c> 5g (yield 98.1%).

Synthesis of 2- (4) <Formula 85>

<Chemical Formula 85> was synthesized by the following Scheme 14.

[Reaction Scheme 14]

<Formula 85>

Except for using <2-c> synthesized in Scheme 12 instead of <1-b> used in Scheme 3, it was synthesized in the same manner to give 2g (yield 48.4%).

MS (MALDI-TOF): m / z 672.3 [M] ⁺

¹³ C NMR (75 MHz, CDCl ₃ ) δ: 22.9 30.9 45.5 109.7 119 121.6 123.2 126.7 127.5 129.2 129.6 131 131.1 131.4 134.7 136.5 141 146.2 147.8 172.2 178.2 [48C]

Synthesis Example 3 Synthesis of <Formula 98>

Synthesis of 3- (1) <3-a>

<3-a> was synthesized according to Scheme 15 below.

[Reaction Scheme 15]

<3-a>

Synthesis was carried out in the same manner, except that phenylmagnesium bromide was used instead of methylmagnesium bromide used in Scheme 2, to obtain 10.8 g (yield 88.2%).

Synthesis of 3- (2) <3-b>

<3-b> was synthesized according to Scheme 16 below.

[Reaction Scheme 16]

<3-b>

Except for <3-a> synthesized in Scheme 23 instead of <1-b> used in Scheme 3, the compound was synthesized in the same manner to obtain 4.1 g (yield 78.4%).

Synthesis of 3- (3) <3-c>

<3-c> was synthesized by the following Scheme 17.

[Reaction Scheme 17]

<3-c>

6.1g (yield 88.4%) of <3-c> was obtained in the same manner except for using <3-b> synthesized in Scheme 16 instead of <1-c> used in Scheme 4.

Synthesis of 3- (4) <3-d>

<3-d> was synthesized according to Scheme 18 below.

[Reaction Scheme 18]

<3-d>

Except for using <3-c> synthesized in Scheme 17 instead of <1-d> used in Scheme 6, it was synthesized in the same manner to give 8.1g (yield 73.1%).

Synthesis of 3- (5) <3-e>

<3-e> was synthesized according to Scheme 19 below.

Scheme 19

<3-e>

Except for using <3-d> synthesized in Scheme 18 instead of <1-f> used in Scheme 8, it was synthesized in the same manner to give 16.2 g (yield 56.9%) of <3-e>.

Synthesis of 3- (6) <3-f>

<3-f> was synthesized according to Scheme 20 below.

[Reaction Scheme 20]

<3-f>

Except for using <3-e> synthesized in Scheme 19 instead of <1-h> used in Scheme 9, it was synthesized in the same manner to give 16.2 g (yield 56.9%) of <3-f>.

3- (7) Synthesis of <Formula 98>

<Chemical Formula 98> was synthesized according to Scheme 21 below.

[Reaction Scheme 21]

<Formula 98>

2.4g (yield 48.7%) was obtained by synthesizing in the same manner except for using <3-f> synthesized in Scheme 28 instead of <1-i> used in Scheme 10.

MS (MALDI-TOF): m / z 894.3 [M] ⁺

¹³ C NMR (75 MHz, CDCl ₃ ) δ: 50.7 100.8 105.4 109.5 119.8 120.2 121.4 125.5 125.6 126.2 126.6 127.5 129.2 129.3 131.1 131.9 134 134.2 134.7 135.5 136.8 145.4 147.7 172.2 178.2 [64C]

Synthesis Example 4 Synthesis of <Formula 21>

Synthesis of 4- (1) <4-a>

<4-a> was synthesized by the following Scheme 22.

[Reaction Scheme 22]

<4-a>

<1-f> (10 g, 17 mmol) obtained from Scheme 6, <1-g> (4.16 g 17 mmol) from Scheme 7, potassium carbonate (6.93 g, 50 mmol), tetrakistriphenylphosphine in a 250 ml round bottom flask Palladium (0.39 g, 1 mmol), 20 ml of water, 50 ml of toluene and 50 ml of tetrahydrofuran were added and refluxed for 12 hours. When the reaction was completed, the resulting product was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure. Then, crystals were precipitated using methanol and filtered to obtain 4.5 g (yield 42%) of the title compound.

Synthesis of 4- (2) <4-b>

<4-b> was synthesized according to Scheme 23 below.

[Reaction Scheme 23]

<4-b>

Except for using <4-a> synthesized in Scheme 22 instead of <1-h> used in Scheme 9, 3.1g (4-6.9%) of <4-b> was obtained in the same manner.

Synthesis of 4- (3) <4-c>

<4-c> was synthesized according to Scheme 24 below.

Scheme 24

<4-c>

Except for using <4-b> synthesized in Scheme 23 instead of <1-i> used in Scheme 10, 3.1g (4-6.9%) of <4-c> was obtained in the same manner.

Synthesis of 4- (4) <4-d>

<4-d> was synthesized according to Scheme 25 below.

[Reaction Scheme 25]

<4-d>

5.3g (yield 68.1%) of <4-d> was obtained in the same manner except for using <4-c> synthesized in Scheme 24 instead of <1-f> used in Scheme 12.

Synthesis of 4- (5) <4-e>

<4-e> was synthesized according to Scheme 26 below.

[Reaction Scheme 26]

<4-e>

4.5 g (yield 91.5%) of <4-e> was obtained in the same manner except for using <4-d> synthesized in Scheme 25 instead of <2-b> used in Scheme 13.

4- (6) Synthesis of <Formula 21>

<Chemical formula 21> was synthesized by the following Reaction Scheme 27.

[Reaction Scheme 27]

&Lt; Formula 21 >

Except for using <4-e> synthesized in Scheme 26 instead of <1-b> used in Scheme 3, the compound was synthesized in the same manner to obtain 2.4 g (yield 44.1%).

MS (MALDI-TOF): m / z 721.3 [M] ⁺

¹³ C NMR (75 MHz, CDCl ₃ ) δ: 22.9 30.9 45.5 100.8 105.4 109.5 109.7 119 119.8 120.2 121.4 121.6 123.2 125.5 125.6 126.6 126.7 127.5 129.2 129.3 129.6 131 131.1 131.4 134 134.2 134.7 135.5 136.5 136.8 141 145.4 146.2 147.8 172.2 178.

Synthesis Example 5 Synthesis of <Formula 84>

Synthesis of 5- (1) <5-a>

<5-a> was synthesized according to Scheme 28 below.

[Reaction Scheme 28]

<5-a>

Except for using <1-d> synthesized in Scheme 4 instead of <1-f> used in Scheme 12, the synthesis was carried out in the same manner to obtain 8.1g (yield 72.1%) of <5-a>.

Synthesis of 5- (2) <5-b>

<5-b> was synthesized according to Scheme 29 below.

[Reaction Scheme 29]

<5-b>

Except for using <5-a> synthesized in Scheme 28 instead of <1-a> used in Scheme 2, 7.3 g (yield 65.2%) of <5-b> was obtained in the same manner.

Synthesis of 5- (3) <5-c>

<5-c> was synthesized by the following Scheme 30.

[Reaction Scheme 30]

<5-c>

Synthesis was carried out in the same manner to obtain <5-c> 4.3g (yield 45.2%), except that <5-b> synthesized in Scheme 29 was used instead of <1-b> used in Scheme 3.

Synthesis of 5- (4) <5-d>

<5-d> was synthesized according to Scheme 31 below.

[Reaction Scheme 31]

<5-d>

In a 1000 ml round bottom flask, 2,4,6-trichloropyrimidine (30 g, 164 mmol), phenylboronic acid (43.87 g 360 mmol), potassium carbonate (135.65 g, 981 mmol), tetrakistriphenylphosphinepalladium (9.46 g, 8 mmol), 60 ml of water, 150 ml of toluene and 150 ml of tetrahydrofuran were added and refluxed for 12 hours. When the reaction was completed, the resultant of the reaction was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure, and then precipitated with methanol to precipitate the crystals and filtered to obtain 31.4g (72% yield) of the compound of formula 5-d. .

5- (5) Synthesis of <Formula 84>

A compound of <Formula 84> was synthesized by the following Scheme 32.

[Reaction Scheme 32]

<Formula 84>

<5-c> (5 g, 11 mmol) obtained in Scheme 30 was added to a 500 ml round bottom flask, and 25 ml of dimethylformamide was stirred. Then, 60% sodium hydride (0.6 g, 17 mmol) was added and stirred for 1 hour. <5-d> (5.07 g, 17 mmol) obtained in Scheme 31 was dissolved in 25 ml of dimethylformamide, and then added to the reaction solution for 1 hour, followed by stirring for 5 hours. After the reaction was completed, the reaction solution was poured into 250 ml of water and filtered to obtain 6.1 g (yield 80.3%) of the compound.

MS (MALDI-TOF): m / z 671.3 [M] ⁺

¹³ C NMR (75 MHz, CDCl ₃ ) δ: 22.9 30.9 45.5 101.3 109.7 119 121.6 123.2 126.7 127.5 128.7 129.2 129.6 131 131.4 135.8 136.5 141 146.2 147.8 163.6 169.7 [49C]

Synthesis Example 6 Synthesis of <Formula 99>

Synthesis of 6- (1) <6-a>

<6-a> was synthesized by the following Scheme 33.

[Reaction Scheme 33]

<6-a>

At room temperature, 2-aminobenzonitrile (20.0 g, 169 mmol) and 140 mL of tetrahydrofuran were added to a round bottom flask under a nitrogen stream and stirred. 112.9 mL (339 mmol) of phenylmagnesium bromide (3.0 M in Et ₂ O) was added dropwise. After reflux stirring for about 1 hour, the temperature was set to 0 캜. Ethyl chloroformate (22.0 g, 203 mmol) was added dropwise thereto, followed by reflux stirring for about 1 hour. The aqueous ammonium chloride solution was added until weakly acidic, and the resulting solid was filtered and washed with water and heptane to give 30.1 g of <6-a>. (Yield 80%)

Synthesis of 6- (2) <6-b>

<6-b> was synthesized by the following Scheme 34.

[Reaction Scheme 34]

<6-b>

At room temperature, about 80 mL of the above synthesized <6-a> (30.0 g, 135 mmol) and phosphorus oxychloride were added to a round bottom flask under a nitrogen stream, followed by stirring. After refluxing overnight, the temperature was cooled to −20 ° C. the next day and water was slowly added dropwise to about 400 mL. The resulting solid was filtered and washed with water, methanol and heptane. Recrystallization with toluene and heptane gave 14.6 g of <6-b>. (Yield: 44.9%).

Synthesis of 6- (3) <6-c>

<6-c> was synthesized by the following Scheme 35.

[Reaction Scheme 35]

<6-c>

Instead of <1-e> used in [Scheme 6], 17.5 g of <6-c> was obtained by the same method using the synthesized <6-b>. (Yield 83%)

6- (4) Synthesis of <Formula 99>

<Chemical Formula 99> was synthesized by the following Reaction Scheme 36.

[Reaction Scheme 36]

&Lt; Formula 99 >

Instead of <1-f> used in [Scheme 22] of Synthesis Example 4, using the synthesized <6-c> in the same manner as in [Scheme 22] to [Scheme 27] of Synthesis Example 4 2.5g was synthesized. (Yield 28%)

MS (MALDI-TOF): m / z 695

¹³ C NMR (75 MHz, CDCl ₃ ) δ: 22.9 30.9 45.5 100.8 105.4 109.5 109.7 118.5 119 119.8 120.2 121.4 121.6 122.9 123.2 125 125.5 125.6 125.8 126.6 126.7 127.5 128.7 129.2 129.3 129.6 131 131.4 131.8 134 134.2 135.5 136.5 136.8 141 145.4 146.2 147 14.2 155.6 160 [50C]

Synthesis Example 7 Synthesis of <Formula 100>

7- (1) Synthesis of <7-a>

<7-a> was synthesized according to Scheme 37 below.

[Reaction Scheme 37]

<7-a>

Under nitrogen stream, 1-nitronaphthalene (50.0g, 289mmol), ethyl cyanoacetate (98.0g, 866mmol), potassium cyanide (20.7g, 318mmol), potassium hydroxide (32.4g, 577mmol) in a round bottom flask immersed in water Was added and stirred. 100 mL of dimethylformamide was added and the temperature was raised to 60 ° C., followed by stirring overnight. The next day, the change in TLC was checked and the temperature of the flask was brought to room temperature. The reaction solution was concentrated under reduced pressure to remove all possible dimethylformamide. The concentrate was transferred to the reactor with a small amount of dichloromethane and 500 mL of 5% aqueous sodium hydroxide solution was added and stirred. After reflux stirring for about 1 hour, the temperature was brought to room temperature. Extracted with ethyl acetate and water. The residue was subjected to column chromatography using ethyl acetate and heptane. Recrystallization with toluene and heptane yielded 24.6 g (yield 50.7%) of <7-a> as a white solid.

7- (2) Synthesis of <7-b>

<7-b> was synthesized according to Scheme 38 below.

[Reaction Scheme 38]

<7-b>

21g of <7-b> was obtained by synthesizing in the same manner as in [Reaction Scheme 33] to [Reaction Scheme 34] using <7-a> synthesized instead of 2-aminobenzonitrile used in [Reaction Scheme 33]. (Yield 74.5%)

7- (3) Synthesis of <7-c>

<7-c> was synthesized by the following Scheme 39.

[Reaction Scheme 39]

<7-c>

Instead of <1-e> used in [Scheme 6], 18.7 g of <7-c> was obtained by the same method using the synthesized <7-b>. (Yield 86%)

7- (4) Synthesis of <Formula 100>

<Formula 100> was synthesized by the following Scheme 40.

[Reaction Scheme 40]

(100)

Instead of <1-f> used in [Scheme 22] of Synthesis Example 4, using the synthesized <7-c> in the same manner as in [Scheme 22] to [Scheme 27] of Synthesis Example 4 3.1 g was synthesized. (Yield 35%)

MS (MALDI-TOF): m / z 745

¹³ C NMR (75 MHz, CDCl ₃ ) δ: 22.9 30.9 45.5 100.8 105.4 109.5 109.7 118.5 119 119.8 120.2 121.4 121.6 123.1 123.2 124.9 125.5 125.6 125.8 126.6 126.7 127.2 127.3 127.5 128.7 129.2 129.3 129.5 129.6 131 131.4 131.8 133.5 134 134.2 145.4 146.2 147.8 149.9 155.6 160 [54C]

Synthesis Example 8 Synthesis of <Formula 102>

Synthesis of 8- (1) <8-a>

<8-a> was synthesized by the following Reaction Scheme 41.

[Reaction Scheme 41]

<8-a>

Instead of [Chemical Formula 7-a] used in [Scheme 38], 3-amino-2-naphtonitrile was synthesized in the same manner to obtain 20 g of [Formula 8-a]. (Yield 71%)

Synthesis of 8- (2) <8-b>

<8-b> was synthesized by the following reaction scheme.

[Reaction Scheme 42]

<8-b>

Instead of <1-e> used in [Scheme 6], 18.7 g of <8-b> was obtained by the same method using the synthesized <8-a>. (Yield 86%)

8- (3) Synthesis of <Formula 102>

<Chemical Formula 102> was synthesized by the following Reaction Scheme 43.

[Reaction Scheme 43]

<Formula 102>

Instead of <1-f> used in [Scheme 22] of Synthesis Example 4, using the synthesized <8-b> in the same manner as in [Scheme 22] to [Scheme 27] of Synthesis Example 4 2.8 g were synthesized. (Yield 32%)

MS (MALDI-TOF): m / z 745

¹³ C NMR (75 MHz, CDCl ₃ ) δ: 22.9 30.9 45.5 100.8 105.4 109.5 109.7 118.5 119 119.8 120.2 121.4 121.6 123.2 123.4 125.1 125.5 125.6 126.6 126.7 127.2 127.3 127.5 128.7 129.2 129.3 129.6 131 131.4 131.8 132 133.5 134 134.2 135.5 136.5 136.8 146.2 147.8 149.2 155.6 160 [54C]

Examples 1 to 5: Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), the compound prepared in Synthesis Examples 1 to 5 + Ir (ppy ) ₃ (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) in the order of the film formation, and was measured at 0.4 mA.

[DNTPD] [NPD]

[Ir (ppy) ₃ ] [Alq ₃ ]

Comparative Example 1

An organic light emitting diode device for Comparative Example 1 was manufactured in the same manner except for using CBP, which is generally used as a phosphorescent host material, instead of the compound prepared by the invention in the device structures of Examples 1 to 5, The structure is shown below.

For organic light emitting diodes manufactured according to Examples 1 to 5 and Comparative Example 1, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in the following [Table 1].

T80 means the time it takes for the luminance to decrease to 80% from the initial luminance (7000 nit).

division Host Dopant Doping concentration% V Cd / m ² CIEx CIEy T ₈₀ (Hr) Comparative Example 1 CBP Ir (ppy) ₃ 10 7.93 3801 0.297 0.624 68 Example 1 41 Ir (ppy) ₃ 10 4.05 4940 0.313 0.619 212 Example 2 85 Ir (ppy) ₃ 10 4.10 5113 0.312 0.621 125 Example 3 40 Ir (ppy) ₃ 10 4.41 4909 0.314 0.620 141 Example 4 21 Ir (ppy) ₃ 10 4.36 5214 0.313 0.623 85 Example 5 84 Ir (ppy) ₃ 10 4.02 5299 0.306 0.624 201

In order to measure the bandgap of the compound corresponding to Chemical Formulas 41, 85, 98, 21, 84 according to an embodiment of the present invention, it was measured using an UV / Vis absorption spectrometer and a cyclic voltametry. .

division UV (λ _max ) PL (λ _max ) HOMO (eV) LUMO (eV) Band Gap (ev) Formula 41 292, 316, 341 475 6.1 2.9 3.2 Formula 85 294, 318, 342 472 6.0 3.0 3.0 Formula 40 295, 318, 341 476 6.2 2.9 3.3 Formula 21 294, 315, 342 475 6.0 2.7 3.3 84 294, 318, 342 473 6.1 3.0 3.1

Examples 6 to 8: Preparation of an organic light emitting display device including the compound synthesized by Synthesis Examples 6 to 8 above

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr, and the organic material is synthesized on the ITO by DNTPD (700 kPa), NPD (300 kPa), and the compounds synthesized by Synthesis Examples 6 to 8 + (piq ) ₂ Ir (acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) was formed in the order of, was measured at 0.4mA. The structure of (piq) ₂ Ir (acac) is as follows.

[(piq) ₂ Ir (acac)]

Example 9

In the device structures of Examples 6 to 8, [Formula 102] was used as the light emitting layer, and was manufactured in the same manner except that [PTOEP] was used instead of [(piq) ₂ Ir (acac)]. It looks like this:

[PTOEP]

Comparative Example 2

The organic light emitting diode device for Comparative Example 2 was manufactured in the same manner except for using CBP instead of the compound prepared by the present invention as a host material in the device structures of Examples 6 to 8.

For organic light emitting diodes manufactured according to Examples 6 to 9 and Comparative Example 2, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in the following [Table 3].

T90 refers to the time taken for the luminance to decrease to 90% from the initial luminance (3700nit).

division Host Dopant Voltage (V) Brightness (Cd / m ² ) CIEx CIEy T ₈₀ (Hr) Example 6 Formula 99 (piq) &lt; / RTI &gt; ₂ Ir (acac) 4.2 1350 0.668 0.331 1120 Example 7 100 (piq) &lt; / RTI &gt; ₂ Ir (acac) 4.0 1440 0.671 0.334 1080 Example 8 102 (piq) &lt; / RTI &gt; ₂ Ir (acac) 4.0 1410 0.673 0.330 1025 Example 9 102 PTOEP 4.1 1430 0.655 0.328 1000 Comparative Example 2 CBP (piq) &lt; / RTI &gt; ₂ Ir (acac) 7.5 410 0.667 0.328 140

As shown in the above table, the organic compound obtained by the present invention exhibits excellent characteristics such that the driving voltage is much lower than that of CBP among the host materials used as phosphorescent host materials, and the luminous efficiency and lifetime are increased.

Claims (11)

Carbazole derivatives represented by the following [Formula 1]:
[Formula 1]

In [Formula 1],
A ring or B ring each independently

,

,

And

&Lt; / RTI &gt;
Ar ₁ is selected from a substituted or unsubstituted aryl group having 6-50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2-50 carbon atoms,
R ₁ To R ₅ are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. The method of claim 1,
Ar ₁ , R ₁ to R ₅ are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an alkylamino group having 1 to 40 carbon atoms, Arylamino group having 6 to 40 carbon atoms, heteroarylamino group having 3 to 40 carbon atoms, alkylsilyl group having 1 to 40 carbon atoms, arylsilyl group having 6 to 40 carbon atoms, aryl group having 6 to 40 carbon atoms, aryl jade having 3 to 40 carbon atoms Carbazole derivatives, characterized in that further substituted by one or more substituents selected from the group consisting of, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron. The method of claim 1,
[Chemical Formula 1] is a carbazole derivative, characterized in that any one selected from the compounds represented by the following [Formula 1-1] to [Formula 1-13]:
[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

[Formula 1-5] [Formula 1-6]

[Formula 1-7] [Formula 1-8]

[Formula 1-9] [Formula 1-10]

[Formula 1-11] [Formula 1-12]

[Formula 1-13]

In [Formula 1-1] to [Formula 1-13],
Ar ₁ to Ar ₃ are each independently selected from a substituted or unsubstituted aryl group having 6-50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2-50 carbon atoms,
R ₁ And R ₂ are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. The method of claim 3,
Ar ₁ to Ar ₃ are each independently a carbazole derivative, characterized in that any one selected from [formula 1] to [formula 6]:
[Structural formula 1] [Structural formula 2] [Structural formula 3]

[Structural formula 4] [Structural formula 5] [Structural formula 6]

In the above Structural Formulas 1 to 6,
T ₁ to T ₈ are the same or different and each independently selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ )
R ₃₁ to R ₄₄ Are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted cyclo group having 3 to 30 carbon atoms An alkyl group, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, wherein R ₃₁ to R ₄₄ One is to form a single bond by combining with nitrogen contained in the [Formula 1-1] to [Formula 1-13]. 5. The method of claim 4,
[Formula 1] to [Formula 6] is a carbazole derivative, characterized in that any one selected from the following [formula 7]:
[Structure 7]

In the above formula 7,
X is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon atom Any one selected from 5 to 50 aryl groups and substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms having O, N or S as hetero atoms,
m is an integer of 1 to 11, when m is 2 or more, a plurality of X are the same or different from each other, any one of the at least one X is combined with the nitrogen contained in the [Formula 1] to form a single bond. The method of claim 3,
Ar ₁ to Ar ₃ and R ₁ to R ₂ are each independently a deuterium atom, cyano group, halogen atom, hydroxy group, nitro group, alkyl group of 1-40 carbon atoms, alkoxy group of 1-40 carbon atoms, Alkylamino group, arylamino group of 6-40 carbon atoms, heteroarylamino group of 3-40 carbon atoms, alkylsilyl group of 1-40 carbon atoms, arylsilyl group of 6-40 carbon atoms, aryl group of 6-40 carbon atoms, 3-40 carbon atoms Carbazole derivatives, characterized in that further substituted by one or more substituents selected from the group consisting of an aryloxy group, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron. The method of claim 1,
[Chemical Formula 1] is a carbazole derivative, characterized in that any one selected from the compounds represented by the following [Formula 2] to [Formula 103]:

[Chemical Formula 2] &lt; EMI ID =

[Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]

[Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 28] [Chemical Formula 28]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

[Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45]

[Chemical Formula 48] [Chemical Formula 48] [Chemical Formula 48]

[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]

[Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]

[Formula 79] [Formula 80] [Formula 81]

[Chemical Formula 82]

[Chemical Formula 88] [Chemical Formula 88] [Chemical Formula 89]

[Chemical Formula 91] [Chemical Formula 92] [Chemical Formula 93]

[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 100] [Chemical Formula 100]

[Formula 102] [Formula 103] A first electrode; A second electrode facing the first electrode; And at least one organic layer interposed between the first electrode and the second electrode,
The organic layer is an organic electroluminescent device, characterized in that it comprises at least one carbazole derivative represented by [Formula 1] according to claim 1. 9. The method of claim 8,
Wherein the organic layer comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer and an electron injection layer. 10. The method of claim 9,
The emission layer includes at least one host compound and at least one dopant compound, wherein the host compound is a carbazole derivative represented by the formula [1]. 9. The method of claim 8,
Wherein the organic layer further comprises one or more organic light emitting layers emitting red, green, or blue light to emit white light.

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