KR102307370B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic compound and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic material layers.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound and an organic electroluminescent device including the same.

When a voltage is applied between the two electrodes of the organic electroluminescent device, holes are injected into the anode and electrons are injected into the organic material layer at the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to their function.

To date, hole injection materials, hole transport materials. _{NPB, BCP, Alq 3} and the like are known as hole blocking material and electron transport material, and metal containing Ir such as anthracene derivative, Firpic, Ir(ppy) ₃ , (acac)Ir(btp) _{2 etc. as light emitting material} Complex compounds, CBP, and the like are known.

However, these materials have a low glass transition temperature and poor thermal stability, which is not satisfactory in terms of the lifespan of the organic electroluminescent device.

Republic of Korea Patent Publication No. 2011-0066763

An object of the present invention is to provide a novel organic compound capable of increasing hole injection/transport ability, light emitting ability, and the like of an organic electroluminescent device.

Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound.

상기 화학식 1에서,
R₁과 R₂, R₂와 R₃, R₃와 R₄ 중 하나 이상은 서로 결합하여 하기 화학식 2로 표시되는 축합 고리를 형성하고,
[화학식 2]

상기 화학식 2에서,
점선은 축합이 이루어지는 부분이고,
X₁은 N(Ar₁) 이고,
축합 고리를 형성하지 않는 R₁ 내지 R₄와, R₅ 내지 R₁₆은 각각 독립적으로 수소, 중수소, C₁~C₄₀의 알킬기 및 C₆~C₆₀의 아릴기로 이루어진 군에서 선택되고,
Ar₁은 하기 화학식 3 또는 4로 표시되는 치환체이고,
[화학식 3]

상기 화학식 3에서,
*는 상기 화학식 1에 결합되는 부분을 의미하고;
L₁은 단일결합, C₆~C₁₈의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,
Y₁ 내지 Y₅는 각각 독립적으로 N 또는 C(R₂₁)이며, 이때 C(R₂₁)이 복수인 경우, 이들은 서로 동일 또는 상이하며, 다만 Y₁ 내지 Y₅ 중 1개 이상은 N이고,
상기 R₂₁은 수소, 중수소, C₁~C₄₀의 알킬기, C₆~C₄₀의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기 및 C₆~C₄₀의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고,
[화학식 4]

상기 화학식 4에서,
*는 상기 화학식 1에 결합되는 부분을 의미하고;
L₂은 단일결합, C₆~C₁₈의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,
R₂₃ 및 R₂₄는 각각 독립적으로 C₁~C₄₀의 알킬기, C₆~C₄₀의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기 및 C₆~C₆₀의 아릴아민기로 이루어진 군에서 선택되거나, 서로 결합하여 축합 고리를 형성하며,
상기 R₁ 내지 R₁₆의 알킬기 및 아릴기와 L₁ 및 L₂의 아릴렌기 및 헤테로아릴렌기와 R₂₁, R₂₃ 및 R₂₄의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로, C₁~C₄₀의 알킬기, C₂~C₄₀의 알케닐기, C₂~C₄₀의 알키닐기, C₃~C₄₀의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C₆~C₆₀의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C₆~C₆₀의 아릴옥시기, C₃~C₄₀의 알킬실릴기, C₆~C₆₀의 아릴실릴기, C₁~C₄₀의 알킬보론기, C₆~C₆₀의 아릴보론기, C₆~C₆₀의 아릴포스핀기, C₆~C₆₀의 아릴포스핀옥사이드기 및 C₆~C₆₀의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때, 복수의 치환기로 치환될 경우 이들은 서로 동일 또는 상이하다.In order to achieve the above object, the present invention provides a compound represented by the following formula (1).
[Formula 1]

In Formula 1,
At least _one of R 1 and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ is bonded to each other to form a condensed ring represented by the following Chemical Formula 2,
[Formula 2]

In Formula 2,
The dotted line is the part where the condensation takes place,
X ₁ is N(Ar ₁ ),
_{R 1} to R ₄ and R ₅ to R ₁₆ that do not form a condensed ring are each independently selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group and a C ₆ to C _{60 aryl group,}
Ar ₁ is a substituent represented by the following formula 3 or 4,
[Formula 3]

In Formula 3,
* means a moiety bonded to Formula 1;
L ₁ is a single bond, C ₆ ~ C ₁₈ is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Y _{1 To} Y ₅ are each independently N or C(R ₂₁ ), wherein when C(R ₂₁ ) is a plurality, they are the same or different from each other, provided that at least one of _{Y 1 To} Y _{5 is N,}
wherein R ₂₁ is selected from the group consisting of hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, and C ₆ ~ C ₄₀ arylamine group, or , combine with adjacent groups to form a condensed ring,
[Formula 4]

In Formula 4,
* means a moiety bonded to Formula 1;
L ₂ is a single bond, C ₆ ~ C ₁₈ is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
R ₂₃ and R ₂₄ are each independently selected from _{the group consisting of a C 1} ~ C ₄₀ alkyl group, a C ₆ ~ C ₄₀ aryl group, a heteroaryl group of 5 to 40 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group or combine with each other to form a condensed ring,
The _{alkyl group and aryl group of R 1} to R ₁₆ and the arylene group and heteroarylene group of L ₁ and L ₂ and the alkyl group, aryl group, heteroaryl group and arylamine group of R ₂₁ , R ₂₃ and R _{24 are each independently C 1} ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ of an aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ Aryloxy group, C ₃ to C ₄₀ Alkylsilyl group, C ₆ to C ₆₀ Arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide ₆₀ group and a C ₆ ~ C ₆₀ aryl amine group selected from the group consisting of It is substituted or unsubstituted with one or more substituents, and in this case, when substituted with a plurality of substituents, they are the same or different from each other.

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In addition, the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers One provides an organic electroluminescent device including the compound represented by Formula 1 above.

In the present invention, alkyl means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, alkenyl refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl) and the like.

In the present invention, alkynyl refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

In the present invention, aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. In this case, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples thereof include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, Polycyclic rings such as purinyl, quinolyl, benzothiazole, and carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2- pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

In the present invention, aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, alkyloxy is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do. Examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.

In the present invention, cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or Se substituted with a hetero atom such as Examples thereof include, but are not limited to, morpholine and piperazine.

In the present invention, alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

Since the compound represented by Formula 1 of the present invention has excellent thermal stability and light emitting properties, it can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host of the light emitting layer, an organic electroluminescent device having excellent light emitting performance, driving voltage and lifespan characteristics can be manufactured, and furthermore, a full color display panel with improved performance and lifespan can be manufactured.

Hereinafter, the present invention will be described.

1. Organic Compounds

The present invention provides a novel chrysene-based compound having a linear structure in which an aromatic ring or a heteroaromatic ring is condensed at positions 1, 2, 3, and 4 of the following chrysene. Specifically, the organic compound of the present invention is represented by the above formula (1).

Chrysene-based compounds have a low HOMO energy level and a wide energy band gap, so they are chemically stable. When a substituent having various functions is introduced into such a chrysene-based compound, it may have a wide energy band gap and chemical properties.

Specifically, the compound represented by Formula 1 of the present invention in which an aromatic ring or a heteroaromatic ring is condensed at positions 1, 2, 3, and 4 of chrysene is a compound of chrysene at positions 5 and 6, or at positions 11 and 12 Compared to the chrysene-based compound in which an aromatic ring or a heteroaromatic ring is condensed at the position, intermolecular stacking occurs better, so that electron movement is smooth.

In addition, the compound represented by Formula 1 of the present invention is an aryl group (phenyl, biphenyl, terphenyl, triphenylene, naphthalene, anthracene), or a substituent having excellent hole injection/transportability such as an arylamine group is introduced to inject and The transport is smooth, and electron injection and transport is also smooth because a substituent having excellent electron injection/transportability such as a heteroaryl group is introduced. In addition, the compound represented by Formula 1 of the present invention has a low HOMO energy level due to the chrysene structure, and is effective in blocking the movement of excitons and holes.

Therefore, when the compound represented by Formula 1 of the present invention is used as a material for forming an organic material layer (specifically, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, a light emitting layer) of an organic electroluminescent device, light emission It is possible to provide an organic electroluminescent device having excellent efficiency, a low driving voltage, and a long lifespan.

In the compound represented by Formula 1 of the present invention, at least one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ may be bonded to each other to form a condensed ring represented by Formula 2 above. Specifically, _one of R 1 and R ₂ , R ₂ and R ₃ , and R ₃ and R ₄ may combine with each other to form a condensed indole including N.

The compound represented by Chemical Formula 1 of the present invention may be embodied as any one of the compounds represented by the following Chemical Formulas 1-A to 1-J.

In Formulas 1-A to 1-J,

X ₁ and R ₁ to R ₁₆ are the same as defined in Formula 1, wherein a plurality of R ₁₃ are the same as or different from each other, a plurality of R ₁₄ are the same or different from each other, and a plurality of R ₁₅ are the same as or different, and a plurality of R ₁₆ are the same as or different from each other.

In Formulas 1-A to 1-J, X ₁ is N(Ar ₁ ).

Meanwhile, in the compound represented by Formula 1 of the present invention, at least one of _{R 1} to R ₄ and R ₅ to R ₁₆ and Ar _{1 does not form a condensed ring is a C 1} to C ₄₀ alkyl group, C ₆ to C ₆₀ It is preferably selected from the group consisting of an aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having ₆ to C _{60 atoms.}

Specifically, Ar ₁ is preferably a substituent represented by the following formula (3).

[Formula 3]

In Formula 3,

* means a moiety bonded to Formula 1,

L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms (preferably a single bond, a phenylene group, a biphenylene group, a carbazolene group),

Y _{1 To} Y _{5 Are} the same as or different from each other, and each independently represents N or C(R ₂₁ ), wherein, when C(R ₂₁ ) is a plurality, R ₂₁ are the same as or different from each other,
wherein R ₂₁ is selected from the group consisting of hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, and C ₆ ~ C ₄₀ arylamine group, or , combine with adjacent groups to form a condensed ring.

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The _{alkyl group, aryl group, heteroaryl group and arylamine group of R 21} are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group substituents of two or more selected from the group consisting of and unsubstituted or substituted with , In this case, when substituted with a plurality of substituents, the plurality of substituents are the same or different from each other.

Such a substituent represented by Formula 3 may be embodied as any one of the substituents represented by the following A-1 to A-15.

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In the above A-1 to A-15,

L ₁ and R ₂₁ are as defined in Formula 3 above,

R ₂₂ is deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₄₀ aryl group, 5 to 40 nuclear atom heteroaryl group, C ₆ to C ₄₀ aryloxy group C ₁ to C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ Arylphosphine oxide group and C ₆ ~ C _{40 It} is selected from the group consisting of an arylsilyl group _{, or is combined with an adjacent group (eg, L 1} , R ₂₁ , or other R ₂₂ ) to form a condensed ring, ,

n is an integer from 0 to 4.

Alkyl group of the R _22, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphine group, aryl phosphine oxide group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C _{40 alky} Nyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ arylboron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group being unsubstituted or substituted by one substituent at least one selected from the group consisting of, at this time, When substituted with a plurality of substituents, the plurality of substituents are the same or different from each other.

In addition, Ar ₁ is preferably a substituent represented by the following formula (4).

[Formula 4]

In Formula 4,

* means a moiety bonded to Formula 1,

L ₂ is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms (preferably a single bond, a phenylene group, a biphenylene group, a carbazolene group),

R ₂₃ and R ₂₄ are each independently selected from _{the group consisting of a C 1} ~ C ₄₀ alkyl group, a C ₆ ~ C ₄₀ aryl group, a heteroaryl group of 5 to 40 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group or combine with each other to form a condensed ring,

The _{alkyl group, aryl group, heteroaryl group and arylamine group of R 23} and R ₂₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group substituted or by one substituent at least one selected from the group consisting of When unsubstituted and substituted with a plurality of substituents, the plurality of substituents are the same or different from each other.

Specific examples of the compound represented by Formula 1 of the present invention include, but are not limited to, the following compounds (R1 to R180).

2. Organic electroluminescent device

The present invention provides an organic electroluminescent device comprising the compound represented by Formula 1 above.

Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is the and a compound represented by the formula (1). In this case, the compound may be used alone, or two or more may be used in combination.

The at least one organic layer may be any one or more of a hole injection layer, a hole transport layer, a hole barrier layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer, and at least one organic layer is a compound represented by Formula 1 may include. Specifically, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer, an electron transport layer, and a hole transport layer. The light emitting layer may include a host, and in this case, as a host, a compound represented by Formula 1 or a compound other than the compound represented by Formula 1 may be included as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked. In this case, an electron injection layer may be additionally stacked on the electron transport layer. An insulating layer or an adhesive layer may be additionally inserted at the interface between the anode and the cathode and the organic material layer.

The organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer contains the compound represented by Formula 1 above. .

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.

The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, etc. may be used.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.

In addition, examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO2/Al, but is not limited thereto.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of A1

<Step 1> Synthesis of 1-(2-nitrophenyl)chrysene

1-chlorochrysene 3.7g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh ₃ ) ₄ 0.6g (5 mol%), potassium carbonate 4.5g (32.3mmol) and 80ml/40ml under a nitrogen stream /40ml of Toluene/H ₂ O/Ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain 1-(2-nitrophenyl)chrysene (3.1 g, 8,8 mmol, yield 82%) as the target compound.

GC-Mass (theoretical: 349.38 g/mol, measured: 349 g/mol)

¹ H-NMR: δ 7.66 (t, 1H), 7.71 (s, 2H), 7.83 to 7.94 (m, 7H), 8.12 (d, 2H), 8.88 to 8.92 (m, 3H)

<Step 2> Synthesis of A1

Under a nitrogen stream, 3.1 g (8.8 mmol) of 1-(2-nitrophenyl) chrysene, 5.8 g (22.0 mmol) of triphenylphosphine, and 30 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A1 (2.1 g, 6.5 mmol, yield 74%).

GC-Mass (theoretical: 317.38 g/mol, measured: 317 g/mol)

¹ H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83 to 7.88 (m, 4H), 8.12 (d, 2H), 8.88~8.92(m, 3H), 10.01(s, 1H)

[Preparation Example 2] Synthesis of A2 and A3

<Step 1> Synthesis of 2-(2-nitrophenyl)chrysene

2-chlorochrysene 3.7 g, (10.8 mmol), 2-nitrophenylboronic acid 1.8 g (10.8 mmol), Pd(PPh ₃ ) ₄ 0.6 g (5 mol%), potassium carbonate 4.5 g (32.3 mmol) and 80 ml/ 40ml/40ml of Toluene/H ₂ O/Ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, 2-(2-nitrophenyl)chrysene (3.2 g, 9.0 mmol, yield 84%).

GC-Mass (theoretical: 349.38 g/mol, measured: 349 g/mol)

¹ H-NMR: δ 7.66 (m, 1H), 7.71 (s, 2H), 7.83 to 8.12 (m, 8H), 8.33 (s, 1H), 8.92 to 8.98 (m, 3H)

<Step 2> Synthesis of A2 and A3

Under a nitrogen stream, 3.2 g (9.0 mmol) of 2-(2-nitrophenyl) chrysene, 5.9 g (22.6 mmol) of triphenylphosphine and 30 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain target compounds A2 (0.9 g, 3.0 mmol, yield 33%) and A3 (0.8 g, 2.5 mmol, yield 28%).

A2: GC-Mass (theoretical: 317.38 g/mol, measured: 317 g/mol)

¹ H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83 to 7.88 (m, 3H), 8.12 (d, 3H), 8.91~8.92(m, 3H), 10.01(s, 1H)

A3:GC-Mass (theoretical: 317.38 g/mol, measured: 317 g/mol)

¹ H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83 to 7.88 (m, 4H), 8.12 (d, 2H), 8.91~8.92(m, 3H), 10.01(s, 1H)

[Preparation Example 3] Synthesis of A4 and A5

<Step 1> Synthesis of 3-(2-nitrophenyl)chrysene

3-chlorochrysene 3.7 g (10.8 mmol), 2-nitrophenylboronic acid 1.8 g (10.8 mmol), Pd(PPh ₃ ) ₄ 0.6 g (5 mol%), potassium carbonate 4.5 g (32.3 mmol) and 80 ml/40 ml under a nitrogen stream /40ml of Toluene/H ₂ O/Ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain 3-(2-nitrophenyl)chrysene (3.2 g, 9.0 mmol, yield 84%) as the target compound.

GC-Mass (theoretical: 349.38 g/mol, measured: 349 g/mol)

¹ H-NMR: δ 7.66 (t, 1H), 7.71 (s, 2H), 7.83-8.17 (m, 9H), 8.91 (d, 2H), 9.13 (s, 1H)

<Step 2> Synthesis of A4 and A5

3-(2-nitrophenyl)chrysene 3.2g (9.0mmol), triphenylphosphine 5.9g (22.6 mmol) and 1,2-dichlorobenzene 30ml were added under a nitrogen stream, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain target compounds A4 (0.9g, 2.9mmol, yield 31%) and A5 (0.8g, 2.6mmol, yield 29%).

A4: GC-Mass (theoretical: 317.38 g/mol, measured: 317 g/mol)

¹ H-NMR: δ 7.28 (m, 1H), 7.49 (m, 1H), 7.62 (d, 1H), 7.72 (s, 2H), 7.82 to 7.87 (m, 4H), 8.10 to 8.12 (m, 3H) ), 8.91 (d, 2H), 10.0 (s, 1H)

A5: GC-Mass (theoretical: 317.38 g/mol, measured: 317 g/mol)

¹ H-NMR: δ 7.28 (m, 1H), 7.49 (m, 1H), 7.62 (d, 1H), 7.72 (s, 2H), 7.82 to 7.87 (m, 3H), 8.10 to 8.12 (m, 3H) ), 8.91 (d, 3H), 10.0 (s, 1H)

[Preparation Example 4] Synthesis of A6

<Step 1> Synthesis of 4-(2-nitrophenyl)chrysene

4-chlorochrysene 3.7 g, (10.8 mmol), 2-nitrophenylboronic acid 1.8 g (10.8 mmol), Pd(PPh ₃ ) ₄ 0.6 g (5 mol%), potassium carbonate 4.5 g (32.3 mmol) and 80 ml/ 40ml/40ml of Toluene/H ₂ O/Ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, 4-(2-nitrophenyl)chrysene (3.1 g, 8.8 mmol, yield 82%).

GC-Mass (theoretical: 349.38 g/mol, measured: 349 g/mol)

¹ H-NMR: δ 7.66 (t, 1H), 7.71 (s, 2H), 7.83 to 8.11 (m, 10H), 8.91 (d, 2H)

<Step 2> Synthesis of A6

Under a nitrogen stream, 3.1 g (8.8 mmol) of 4-(2-nitrophenyl) chrysene, 5.8 g (22.0 mmol) of triphenylphosphine and 30 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A6 (2.1 g, 6.7 mmol, yield 76%).

GC-Mass (theoretical: 317.38 g/mol, measured: 317 g/mol)

¹ H-NMR: δ 7.28 (m, 1H), 7.49 (m, 1H), 7.62 (d, 1H), 7.72 (s, 2H), 7.82 to 7.88 (m, 4H), 8.10 to 8.11 (m, 3H) ), 8.91 (d, 2H), 10.0 (s, 1H)

[Preparation Example 5] Synthesis of A7

<Step 1> Synthesis of 4-chloro-1-(2-nitrophenyl)chrysene

1,4-dichlorochrysene 3.2 g (10.8 mmol), 2-nitrophenylboronic acid 1.8 g (10.8 mmol), Pd(PPh ₃ ) ₄ 0.6 g (5 mol%), potassium carbonate 4.5 g (32.3 mmol) and 80 ml under a nitrogen stream /40ml/40ml of Toluene/H ₂ O/Ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, 4-chloro-1-(2-nitrophenyl)chrysene (2.2g, 5.6mmol, yield 52%).

GC-Mass (theoretical: 383.83 g/mol, measured: 349 g/mol)

¹ H-NMR: δ 7.66 (m, 1H), 7.71 (s, 2H), 7.83 to 8.12 (m, 9H), 8.92 to 8.98 (m, 2H)

<Step 2> Synthesis of 7-chloro-9H-phenanthro[1,2-c]carbazole

Under a nitrogen stream, 2.2 g (5.6 mmol) of 4-chloro-1-(2-nitrophenyl) chrysene, 3.7 g (14.0 mmol) of triphenylphosphine, and 20 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, 7-chloro-9H-phenanthro[1,2-c]carbazole (1.5g, 4.2mmol, yield 75%).

GC-Mass (theoretical: 351.83 g/mol, measured: 351 g/mol)

¹ H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83 to 7.88 (m, 4H), 8.12 (d, 2H), 8.91~8.92(m, 2H), 10.01(s, 1H)

<Step 3> Synthesis of 7-(2-nitrophenyl)-9H-phenanthro[1,2-c]carbazole

Under nitrogen stream 7-chloro-9H-phenanthro[1,2-c]carbazole 1.5g, (4.2mmol), 2-nitrophenylboronic acid 0.7g (4.2mmol), Pd(PPh ₃ ) ₄ 0.2g (5 mol%) , potassium carbonate 1.7g (12.3 mmol) and 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol were added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound 7-(2-nitrophenyl)-9H-phenanthro[1,2-c]carbazole (1.5 g, 3.4 mmol, yield 82%).

GC-Mass (theoretical: 438.83 g/mol, measured: 438 g/mol)

¹ H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (m, 2H), 7.71 (s, 2H), 7.83 to 8.10 (m, 9H), 8.91 to 8.92 (d, 2H) ), 10.01(s, 1H)

<Step 4> Synthesis of 7-(2-nitrophenyl)-9-phenyl-9H-phenanthro[1,2-c]carbazole

Under nitrogen stream, 7-(2-nitrophenyl)-9H-phenanthro[1,2-c]carbazole 1.5g (3.4mmol), iodobenzene 2.1g (10.3mmol), Cu powder 0.2g (2.4mmol), K ₂ CO ₃ 1.0g (6.9mmol) and 10 ml of nitrobenzene were mixed and stirred at 200 °C for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound 7-(2-nitrophenyl)-9-phenyl-9H-phenanthro[1,2-c]carbazole (1.4 g, 2.7 mmol, yield 79%). got it

GC-Mass (theoretical: 514.57 g/mol, measured: 514 g/mol)

¹ H-NMR: δ 7.24 to 7.32 (m, 2H), 7.45 to 7.66 (m, 6H), 7.71 (s, 2H), 7.92 to 8.10 (m, 9H), 8.51 (d, 1H), 8.91 to 8.92 (d, 2H)

<Step 5> Synthesis of A7

7-(2-nitrophenyl)-9-phenyl-9H-phenanthro[1,2-c]carbazole 1.4g (2.7mmol), triphenylphosphine 1.8g (6.8mmol) and 20 ml of 1,2-dichlorobenzene were added under a nitrogen stream. After that, the mixture was stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A7 (1.0 g, 2.0 mmol, yield 75%).

GC-Mass (Theory: 482.57 g/mol, Measured: 482 g/mol)

¹ H-NMR: δ 7.24 to 7.32 (m, 3H), 7.45 to 7.66 (m, 7H), 7.71 (s, 2H), 7.88 to 7.93 (m, 4H), 8.11 (d, 2H), 8.51 (d) , 1H), 8.91 to 8.92 (d, 2H), 10.01 (s, 1H)

[Preparation Example 6] Synthesis of A8

<Step 1> Synthesis of 4-chloro-1-(2-nitrophenyl)chrysene

1,4-dichlorochrysene 3.2 g (10.8 mmol), 2-nitrophenylboronic acid 1.8 g (10.8 mmol), Pd(PPh ₃ ) ₄ 0.6 g (5 mol%), potassium carbonate 4.5 g (32.3 mmol) and 80 ml under a nitrogen stream /40ml/40ml of Toluene/H ₂ O/Ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, 4-chloro-1-(2-nitrophenyl)chrysene (2.2g, 5.6mmol, yield 52%).

GC-Mass (theoretical: 383.83 g/mol, measured: 349 g/mol)

¹ H-NMR: δ 7.66 (m, 1H), 7.71 (s, 2H), 7.83 to 8.12 (m, 9H), 8.92 to 8.98 (m, 2H)

<Step 2> Synthesis of 7-chloro-9H-phenanthro[1,2-c]carbazole

Under a nitrogen stream, 2.2 g (5.6 mmol) of 4-chloro-1-(2-nitrophenyl) chrysene, 3.7 g (14.0 mmol) of triphenylphosphine and 20 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, 7-chloro-9H-phenanthro[1,2-c]carbazole (1.5g, 4.2mmol, yield 75%).

GC-Mass (theoretical: 351.83 g/mol, measured: 351 g/mol)

¹ H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83 to 7.88 (m, 4H), 8.12 (d, 2H), 8.91~8.92(m, 2H), 10.01(s, 1H)

<Step 3> Synthesis of A8

Under a nitrogen stream, 7-chloro-9H-phenanthro[1,2-c]carbazole 1.5g (4.2mmol), phenylboronic acid 0.5g (4.2mmol), Pd(PPh ₃ ) ₄ 0.2g (5mol%), potassium carbonate 1.7 g (12.3mmol) and 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol were added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A8 (1.4 g, 3.4 mmol, yield 82%).

GC-Mass (theoretical: 438.83 g/mol, measured: 438 g/mol)

¹ H-NMR: δ 7.24 to 7.32 (m, 3H), 7.45 to 7.66 (m, 7H), 7.71 (s, 2H), 7.88 to 7.93 (m, 4H), 8.11 (d, 2H), 8.51 (d) , 1H), 8.91 to 8.92 (d, 2H), 10.01 (s, 1H)

[Preparation Example 7] Synthesis of A9

<Step 1> Synthesis of 1-(5-bromo-2-nitrophenyl)chrysene

1-chlorochrysene 3.7 g (10.8 mmol), 5-bromo-2-nitrophenylboronic acid 2.6 g (10.8 mmol), Pd(PPh ₃ ) ₄ 0.6 g (5 mol%), potassium carbonate 4.5 g (32.3 mmol) and 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain 1-(5-bromo-2-nitrophenyl)chrysene (3.4 g, 8.6 mmol, yield 80%) as the target compound.

GC-Mass (theoretical: 428.28 g/mol, measured: 328 g/mol)

¹ H-NMR: δ 7.71 (s, 3H), 7.83 to 8.11 (m, 7H), 8.20 (d, 1H), 8.92 to 8.93 (m, 3H)

<Step 2> Synthesis of 12-bromo-9H-phenanthro[1,2-c]carbazole

1-(5-bromo-2-nitrophenyl)chrysene 3.7g (8.6mmol), triphenylphosphine 5.6g (21.5mmol) and 1,2-dichlorobenzene 40ml under a nitrogen stream were added and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound 12-bromo-9H-phenanthro[1,2-c]carbazole (2.6g, 6.5mmol, yield 75%).

GC-Mass (Theory: 396.28 g/mol, Measured: 396 g/mol)

¹ H-NMR: δ 7.40 (d, 1H), 7.51 (d, 1H), 7.71 (s, 2H), 7.83 to 7.88 (m, 4H), 7.79 (s, 1H), 8.12 (d, 1H), 8.92~8.93(m, 3H), 10.01(s, 1H)

<Step 3> Synthesis of A9

Under a nitrogen stream, 12-bromo-9H-phenanthro[1,2-c]carbazole 2.6g (6.5mmol), phenylboronic acid 0.8g (6.5mmol), Pd(PPh ₃ ) ₄ 0.4g (5mol%), potassium carbonate 2.7 g (19.4mmol) and 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol were added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A9 (2.0 g, 5.2 mmol, yield 80%).

GC-Mass (theoretical: 393.48 g/mol, measured: 393 g/mol)

¹ H-NMR: δ 7.40 to 7.51 (m, 5H), 7.69 (d, 1H), 7.71 (s, 2H), 7.77 to 7.88 (m, 6H), 8.12 (d, 1H), 8.92 to 8.93 (m) , 3H), 10.01 (s, 1H)

[Preparation Example 8] Synthesis of A10

<Step 1> Synthesis of 1-(2-nitrophenyl)chrysene

1-chlorochrysene 3.7g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh ₃ ) ₄ 0.6g (5mol%), potassium carbonate 4.5g (32.3mmol) and 80ml/40ml/ under a nitrogen stream 40ml of Toluene/H ₂ O/Ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain 1-(2-nitrophenyl)chrysene (3.1 g, 8.8 mmol, yield 82%) as the target compound.

GC-Mass (theoretical: 349.38 g/mol, measured: 349 g/mol)

¹ H-NMR: δ 7.67 (m, 1H), 7.71 (s, 2H), 7.87 to 8.10 (m, 9H), 8.92 to 8.93 (m, 3H)

<Step 2> Synthesis of 9H-phenanthro[1,2-c]carbazole

Under a nitrogen stream, 3.1 g (8.8 mmol) of 1-(2-nitrophenyl) chrysene, 5.8 g (22.0 mmol) of triphenylphosphine and 30 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, 9H-phenanthro[1,2-c]carbazole (2.1g, 6.5 mmol, yield 74%).

GC-Mass (theoretical: 317.28 g/mol, measured: 317 g/mol)

¹ H-NMR: δ 7.30 (m, 1H), 7.50 (m, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.82 to 7.88 (m, 4H), 8.10 (d, 2H), 8.92~8.93(m, 3H), 10.01(s, 1H)

<Step 3> Synthesis of 5-bromo-9H-phenanthro[1,2-c]carbazole

9H-phenanthro[1,2-c]carbazole 2.1g (6.5mmol), NBS (N-bromosuccinimide) 1.2g (6.5mmol), and DMF 20 ml were mixed under a nitrogen stream and stirred at 60 °C for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, 5-bromo-9H-phenanthro[1,2-c]carbazole (2.0 g, 5.0 mmol, yield 77%).

GC-Mass (theoretical: 396.38 g/mol, measured: 396 g/mol)

¹ H-NMR: δ 7.30 (m, 1H), 7.50 (m, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.82 to 7.87 (m, 3H), 8.10 (d, 2H), 8.92~8.93(m, 2H), 9.08(s, 1H), 10.01(s, 1H)

<Step 4> Synthesis of A10

Under a nitrogen stream, 5-bromo-9H-phenanthro[1,2-c]carbazole 2.0g (5.0mmol), phenylboronic acid 0.6g (5.0mmol), Pd(PPh ₃ ) ₄ 0.3g (5mol%), potassium carbonate 2.1 g (15.1mmol) and 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol were added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A10 (1.6 g, 4.0 mmol, yield 79%).

GC-Mass (theoretical: 393.48 g/mol, measured: 393 g/mol)

¹ H-NMR: δ 7.29 (m, 1H), 7.42 to 7.50 (m, 4H), 7.64 (d, 1H), 7.71 (s, 2H), 7.79 to 7.87 (m, 5H), 8.10 (d, 2H) ), 8.92~8.93(m, 2H), 9.08(s, 1H), 10.01(s, 1H)

[Synthesis Example 1] Synthesis of R1

A1 2.1g (6.5mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 2.5g (7.2mmol), Pd ₂ (dba) ₃ 0.3g (5mol% under nitrogen stream) ), tri- tert- butylphosphine 0.1 g (0.3 mmol), sodium tert-butoxide 1.9 g (19.6 mmol), and 50 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R1 (2.8g, 4.5mmol, yield 69%).

GC-Mass (theoretical: 624.73 g/mol, measured: 624 g/mol)

[Synthesis Example 2] Synthesis of R6

A1 2.1g (6.5mmol), 2-chloro-4-phenylquinazoline 1.7g (7.2mmol), Pd ₂ (dba) ₃ 0.3g (5mol%), tri- tert- butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (19.6mmol) and 50ml of Toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R6 (2.5g, 4.7mmol, yield 72%).

GC-Mass (theoretical: 521.61 g/mol, measured: 521 g/mol)

[Synthesis Example 3] Synthesis of R11

A1 2.1g (6.5mmol), N-chloro-N-phenylaniline 1.2g (7.2mmol), Pd ₂ (dba) ₃ 0.3g (5mol%), tri- tert- butylphosphine 0.1g (0.3mmol), under a nitrogen stream Sodium tert-butoxide 1.9g (19.6mmol) and 50ml of Toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R11 (2.3g, 4.7mmol, yield 72%).

GC-Mass (Theory: 484.59 g/mol, Measured: 484 g/mol)

[Synthesis Example 4] Synthesis of R26

A2 1.0g (3.0mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.1g (7.2mmol), Pd ₂ (dba) ₃ 0.1g (5mol% under nitrogen stream) ), tri- tert- butylphosphine 0.1 g (0.1 mmol), sodium tert-butoxide 0.9 g (8.9 mmol), and 20 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R26 (1.2g, 1.9mmol, yield 65%).

GC-Mass (theoretical: 624.73 g/mol, measured: 624 g/mol)

[Synthesis Example 5] Synthesis of R31

A2 1.0g (3.0mmol), 2-chloro-4-phenylquinazoline 1.1g (3.3mmol), Pd ₂ (dba) ₃ 0.1g (5mol%), tri- tert- butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.9g (8.9mmol) and 30ml of Toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R31 (1.0g, 1.9mmol, yield 65%).

GC-Mass (theoretical: 521.61 g/mol, measured: 521 g/mol)

[Synthesis Example 6] Synthesis of R36

A2 1.0g (3.0mmol), N-chloro-N-phenylaniline 0.7g (3.3mmol), Pd ₂ (dba) ₃ 0.1g (5mol%), tri- tert- butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.9g (8.9mmol), and 30ml of Toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R36 (0.9g, 1.9mmol, yield 64%).

GC-Mass (Theory: 484.59 g/mol, Measured: 484 g/mol)

[Synthesis Example 7] Synthesis of R51

A3 0.8g (2,5mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.0g (2.8mmol), Pd ₂ (dba) ₃ 0.1g (5mol) under nitrogen stream %), tri- tert- butylphosphine 0.1 g (0.1 mmol), sodium tert-butoxide 0.7 g (7.6 mmol), and 20 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R51 (1.1g, 1.7mmol, yield 67%).

GC-Mass (theoretical: 624.73 g/mol, measured: 624 g/mol)

[Synthesis Example 8] Synthesis of R56

A3 0.8g (2.5mmol), 2-chloro-4-phenylquinazoline 0.7g (2.8mmol), Pd ₂ (dba) ₃ 0.1g (5mol%), tri- tert- butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.7g (7.6mmol) and 30ml of toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R56 (0.9g, 1.7mmol, yield 67%).

GC-Mass (theoretical: 521.61 g/mol, measured: 521 g/mol)

[Synthesis Example 9] Synthesis of R61

A3 0.8g (2.5mmol), N-chloro-N-phenylaniline 0.6g (2.8mmol), Pd ₂ (dba) ₃ 0.1g (5mol%), tri- tert- butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.7g (7.6mmol) and 30ml of toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R61 (0.8g, 1.6mmol, yield 65%).

GC-Mass (Theory: 484.59 g/mol, Measured: 484 g/mol)

[Synthesis Example 10] Synthesis of R76

A4 0.9g (2,8mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.1g (3.1mmol), Pd ₂ (dba) ₃ 0.1g (5mol) under nitrogen stream %), tri- tert- butylphosphine 0.1 g (0.1 mmol), sodium tert-butoxide 0.8 g (8.4 mmol) and 20 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R76 (1.1g, 1.8mmol, yield 63%).

GC-Mass (theoretical: 624.73 g/mol, measured: 624 g/mol)

[Synthesis Example 11] Synthesis of R81

A4 0.9g (2.8mmol), 2-chloro-4-phenylquinazoline 0.7g (3.1mmol), Pd ₂ (dba) ₃ 0.1g (5mol%), tri- tert- butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (8.4mmol) and 30ml of toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R81 (0.9g, 1.8mmol, yield 63%).

GC-Mass (theoretical: 521.61 g/mol, measured: 521 g/mol)

[Synthesis Example 12] Synthesis of R86

A4 0.9g (2.8mmol), N-chloro-N-phenylaniline 0.6g (3.1mmol), Pd ₂ (dba) ₃ 0.1g (5mol%), tri- tert- butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (8.4mmol) and 30ml of toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R86 (0.9g, 1.8mmol, yield 65%).

GC-Mass (Theory: 484.59 g/mol, Measured: 484 g/mol)

[Synthesis Example 13] Synthesis of R101

A5 0.8g (2,6mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.0g (2.9mmol), Pd ₂ (dba) ₃ 0.1g (5mol) under nitrogen stream %), tri- tert- butylphosphine 0.1 g (0.1 mmol), sodium tert-butoxide 0.8 g (7.9 mmol) and 20 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R101 (1.0 g, 1.7 mmol, yield 64%).

GC-Mass (theoretical: 624.73 g/mol, measured: 624 g/mol)

[Synthesis Example 14] Synthesis of R106

A5 0.8g (2.6mmol), 2-chloro-4-phenylquinazoline 0.7g (2.9mmol), Pd ₂ (dba) ₃ 0.1g (5mol%), tri- tert- butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (7.9mmol) and 30ml of Toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R106 (0.9g, 1.7mmol, yield 66%).

GC-Mass (theoretical: 521.61 g/mol, measured: 521 g/mol)

[Synthesis Example 15] Synthesis of R111

A5 0.9g (2.6mmol), N-chloro-N-phenylaniline 0.6g (2.9mmol), Pd ₂ (dba) ₃ 0.1g (5mol%), tri- tert- butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (7.9mmol) and 30ml of Toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R111 (0.9g, 1.8mmol, yield 68%).

GC-Mass (Theory: 484.59 g/mol, Measured: 484 g/mol)

[Synthesis Example 16] Synthesis of R126

A5 2.1g (6.7mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 2.5g (7.4mmol), Pd ₂ (dba) ₃ 0.3g (5mol% under nitrogen stream) ), tri- tert- butylphosphine 0.1 g (0.3 mmol), sodium tert-butoxide 1.9 g (20.1 mmol) and 50 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R126 (2.9g, 4.6mmol, yield 69%).

GC-Mass (theoretical: 624.73 g/mol, measured: 624 g/mol)

[Synthesis Example 17] Synthesis of R131

Under nitrogen flow, A6 2.1g (6.7mmol), 2-chloro-4-phenylquinazoline 1.8g (7.4mmol), Pd ₂ (dba) ₃ 0.3g (5mol%), tri- tert- butylphosphine 0.3g (0.3mmol), Sodium tert-butoxide 1.9g (20.1mmol) and 50ml of Toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R131 (2.4g, 4.6mmol, yield 69%).

GC-Mass (theoretical: 521.61 g/mol, measured: 521 g/mol)

[Synthesis Example 18] Synthesis of R136

Under nitrogen stream, A6 2.1g (6.7mmol), N-chloro-N-phenylaniline 1.5g (7.4mmol), Pd ₂ (dba) ₃ 0.3g (5mol%), tri- tert- butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (20.1mmol) and 50ml of Toluene were added and stirred at 110°C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R136 (2.0g, 4.2mmol, yield 63%).

GC-Mass (Theory: 484.59 g/mol, Measured: 484 g/mol)

[Synthesis Example 19] Synthesis of R151

A7 1.0g (2.0mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 0.8g (2.2mmol), Pd ₂ (dba) ₃ 0.1g (5mol% under nitrogen stream) ), tri- tert- butylphosphine 0.1 g (0.1 mmol), sodium tert-butoxide 0.6 g (6.1 mmol) and 30 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R151 (1.1g, 1.4mmol, yield 71%).

GC-Mass (theoretical: 789.92 g/mol, measured: 789 g/mol)

[Synthesis Example 20] Synthesis of R166

A8 1.4g (3.4mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.3g (3.8mmol), Pd ₂ (dba) ₃ 0.2g (5mol%) under nitrogen stream ), tri- tert- butylphosphine 0.1 g (0.2 mmol), sodium tert-butoxide 1.0 g (10.3 mmol) and 50 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R166 (1.7g, 1.4mmol, yield 69%).

GC-Mass (Theory: 700.83 g/mol, Measured: 700 g/mol)

[Synthesis Example 21] Synthesis of R171

A9 2.0g (5.2mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 2.0g (5.7mmol), Pd ₂ (dba) ₃ 0.2g (5mol% under nitrogen stream) ), tri- tert- butylphosphine 0.1 g (0.3 mmol), sodium tert-butoxide 1.5 g (15.5 mmol) and 50 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R171 (2.5g, 3.6mmol, yield 69%).

GC-Mass (Theory: 700.83 g/mol, Measured: 700 g/mol)

[Synthesis Example 22] Synthesis of R176

A10 1.6g (4.0mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.5g (4.4mmol), Pd ₂ (dba) ₃ 0.2g (5mol%) under nitrogen stream ), tri- tert- butylphosphine 0.1 g (0.1 mmol), sodium tert-butoxide 1.1 g (11.9 mmol) and 50 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R176 (1.8g, 2.6mmol, yield 65%).

GC-Mass (Theory: 700.83 g/mol, Measured: 700 g/mol)

[Examples 1 to 10]

After high-purity sublimation purification of the compound synthesized in Synthesis Example by a commonly known method, a green organic electroluminescent device was prepared according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was ultrasonically cleaned with distilled water. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). The substrate was transferred to

Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / R1, R26, R51, R76, R101, R126, R151, R166, R171, R176 + 10% Ir ( ppy) ₃ (30 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare a green organic electroluminescent device.

[Comparative Example 1]

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of compound R1 as a light emitting host material when the light emitting layer was formed.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , BCP and CBP used in Examples 1 to 10 and Comparative Example 1 are as follows.

[Evaluation Example 1]

For each of the green organic electroluminescent devices prepared in Examples 1 to 10 and Comparative Example 1, the driving voltage, current efficiency, and emission peak were measured at a current density of 10 mA/cm 2 , and the results are shown in Table 1 below.

Sample host Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 1 R1 6.2 515 41.4 Example 2 R26 6.1 514 40.3 Example 3 R51 6.4 513 40.7 Example 4 R76 6.8 514 41.3 Example 5 R101 6.4 515 40.1 Example 6 R126 6.5 515 42.7 Example 7 R151 6.4 514 41.9 Example 8 R166 6.3 515 40.2 Example 9 R171 6.9 514 41.2 Example 10 R176 6.6 515 40.9 Comparative Example 1 CBP 7.1 517 37.0

As shown in Table 1, it can be seen that when the compound of the present invention is applied to the light emitting layer (Examples 1 to 10), the current efficiency and the driving voltage are superior to those of the case where the conventional CBP is applied (Comparative Example 1).

[Examples 11 to 16]

After high-purity sublimation purification of the compound synthesized in Synthesis Example by a commonly known method, a red organic electroluminescent device was prepared according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was ultrasonically cleaned with distilled water. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). The substrate was transferred to

m-MTDATA (60 nm)/TCTA (80 nm)/ R6, R31, R56, R81, R106, R131 each compound + 10% (piq) ₂ Ir(acac) (30nm) on the prepared ITO transparent substrate (electrode) )/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare a red organic electroluminescent device.

[Comparative Example 2]

A red organic electroluminescent device was manufactured in the same manner as in Example 11, except that CBP was used instead of compound R6 as a light emitting host material when the light emitting layer was formed.

The structures of m-MTDATA, TCTA, BCP and CBP used in Examples 11 to 16 and Comparative Example 2 are the same as above, and the structure of (piq) ₂ Ir(acac) is as follows.

[Evaluation Example 2]

For each of the red organic electroluminescent devices prepared in Examples 11 to 16 and Comparative Example 2, the driving voltage and current efficiency were measured at a current density of 10 mA/cm 2 , and the results are shown in Table 2 below.

Sample host Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 11 R6 4.4 621 10.8 Example 12 R31 4.3 621 11.5 Example 13 R56 4.1 620 11.3 Example 14 R81 3.8 621 11.9 Example 15 R106 4.4 621 11.0 Example 16 R131 4.0 621 12.8 Comparative Example 2 CBP 5.5 622 9,1

As shown in Table 2, it can be seen that when the compound of the present invention is applied to the light emitting layer (Examples 11 to 16), the current efficiency and the driving voltage are superior to those of the case where the conventional CBP is applied (Comparative Example 2).

[Examples 17 to 22]

After high-purity sublimation purification of the compound synthesized in Synthesis Example by a commonly known method, a green organic electroluminescent device was prepared according to the following procedure.

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc. Then, the substrate was transferred to a vacuum laminating machine.

m-MTDATA (60nm)/R11, R36, R61, R66, R86, R111, R136 each compound (80nm)/95% DS-H522 (Doosan Electronics) + 5 on the ITO transparent substrate (electrode) prepared as above % DS-501 (Doosan Electronics Co., Ltd.) (30 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in the order to prepare a green organic EL device.

[Comparative Example 3]

A green organic electroluminescent device was manufactured in the same manner as in Example 17, except that NPB was used instead of compound R11 used as a hole transport layer material when the hole transport layer was formed.

The structures of m-MTDATA and BCP used in Examples 17 to 22 and Comparative Example 3 are the same as above, and the structure of the NPB is as follows.

[Evaluation Example 3]

For each of the green organic electroluminescent devices prepared in Examples 17 to 22 and Comparative Example 3, the driving voltage and current efficiency were measured at a current density of 10 mA/cm 2 , and the results are shown in Table 3 below.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example 17 R11 4.4 23.7 Example 18 R36 4.5 22.5 Example 19 R61 4.3 24.1 Example 20 R86 3.8 21.5 Example 21 R111 4.0 22.6 Example 22 R136 4.0 22.1 Comparative Example 3 NPB 5.2 18.1

As shown in Table 3, it can be seen that the case where the compound of the present invention is applied to the hole transport layer (Examples 17 to 22) has better current efficiency and drive voltage than the case where the conventional NPB is applied (Comparative Example 3).

[Examples 23 to 32]

After high-purity sublimation purification of the compound synthesized in Synthesis Example by a commonly known method, a blue organic electroluminescent device was prepared according to the following procedure.

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. After cleaning, the substrate was transferred to a vacuum evaporator.

On the ITO transparent substrate (electrode) prepared as above, DS-205 (Doosan Electronics) (80 nm)/NPB (15 nm)/ R1, R26, R51, R76, R101, R126, R151, R166, R171, R176 Each compound (15 nm) / ADN + 5 % DS-405 (Doosan Electronics) (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) An organic electroluminescent device was prepared.

[Comparative Example 4]

A blue organic electroluminescent device was manufactured in the same manner as in Example 23, except that the compound R1 used as the light emitting auxiliary layer material was not used.

[Comparative Example 5]

A blue organic electroluminescent device was prepared in the same manner as in Example 23, except that Compound A was used instead of Compound R1 used as a light emitting auxiliary layer material.

The structures of NPB and BCP used in Examples 23 to 32 and Comparative Examples 4 and 5 are the same as above, and the structures of ADN and Compound A are as follows.

[Evaluation Example 4]

For each of the blue organic electroluminescent devices prepared in Examples 23 to 32 and Comparative Examples 4 and 5, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 4 below.

Sample light emitting layer Driving voltage (V) Current efficiency (cd/A) Emission peak (nm) Example 23 R1 4.3 9.3 458 Example 24 R26 4.0 8.4 458 Example 25 R51 4.1 8.3 458 Example 26 R76 4.1 8.9 458 Example 27 R101 4,2 8.8 458 Example 28 R126 3.9 7.5 459 Example 29 R151 3.5 6.7 459 Example 30 R166 3.0 6.5 458 Example 31 R171 3.3 6.9 458 Example 32 R176 3.2 6.3 458 Comparative Example 4 - 4.3 4.5 458 Comparative Example 5 A 5.5 5.3 458

As shown in Table 4, it can be seen that when the compound of the present invention is applied to the light emitting auxiliary layer (Examples 23 to 32), the driving voltage and current efficiency are excellent.

Claims (11)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
At least _one of R 1 and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ is bonded to each other to form a condensed ring represented by the following Chemical Formula 2,
[Formula 2]

In Formula 2,
The dotted line is the part where the condensation takes place,
X ₁ is N(Ar ₁ ),
_{R 1} to R ₄ and R ₅ to R ₁₆ that do not form a condensed ring are each independently selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group and a C ₆ to C _{60 aryl group,}
Ar ₁ is a substituent represented by the following formula 3 or 4,
[Formula 3]

In Formula 3,
* means a moiety bonded to Formula 1;
L ₁ is a single bond, C ₆ ~ C ₁₈ is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Y _{1 To} Y ₅ are each independently N or C(R ₂₁ ), wherein when C(R ₂₁ ) is a plurality, they are the same or different from each other, provided that at least one of _{Y 1 To} Y _{5 is N,}
wherein R ₂₁ is selected from the group consisting of hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, and C ₆ ~ C ₄₀ arylamine group, or , combine with adjacent groups to form a condensed ring,
[Formula 4]

In Formula 4,
* means a moiety bonded to Formula 1;
L ₂ is a single bond, C ₆ ~ C ₁₈ is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
R ₂₃ and R ₂₄ are each independently selected from _{the group consisting of a C 1} ~ C ₄₀ alkyl group, a C ₆ ~ C ₄₀ aryl group, a heteroaryl group of 5 to 40 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group or combine with each other to form a condensed ring,
The _{alkyl group and aryl group of R 1} to R ₁₆ and the arylene group and heteroarylene group of L ₁ and L ₂ and the alkyl group, aryl group, heteroaryl group and arylamine group of R ₂₁ , R ₂₃ and R _{24 are each independently C 1} ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ of an aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ Aryloxy group, C ₃ to C ₄₀ Alkylsilyl group, C ₆ to C ₆₀ Arylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide ₆₀ group and a C ₆ ~ C ₆₀ aryl amine group selected from the group consisting of It is substituted or unsubstituted with one or more substituents, and in this case, when substituted with a plurality of substituents, they are the same or different from each other. According to claim 1,
The compound represented by Formula 1 is a compound selected from the group consisting of compounds represented by the following Formulas 1-A to 1-J.

In Formulas 1-A to 1-J,
X ₁ and R ₁ to R ₁₆ are as defined in claim 1, wherein a plurality of R ₁₃ are the same or different from each other, a plurality of R ₁₄ are the same or different from each other, and a plurality of R ₁₅ are the same or different from each other and a plurality of R ₁₆ are the same or different from each other. delete delete delete According to claim 1,
A compound in which the substituent represented by Formula 3 is selected from the group consisting of substituents represented by the following Formulas A-1 to A-15.

In the above A-1 to A-15,
L ₁ and R ₂₁ are as defined in claim 1,
R ₂₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group , C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Aryl phosphine group , C ₆ ~ C ₄₀ Aryl phosphine oxide group and C ₆ ~ C _{40 It} is selected from the group consisting of an arylsilyl group, or combines with an adjacent group to form a condensed ring,
Alkyl group of the R _22, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C _{40 alky} Nyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group being unsubstituted or substituted by one substituent at least one selected from the group consisting of, at this time, When substituted with a plurality of substituents, they are the same or different from each other,
n is an integer from 0 to 4. delete An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 2 and 6. 9. The method of claim 8,
The organic layer containing the compound is a light emitting layer,
The compound is an organic electroluminescent device that is a phosphorescent host of the light emitting layer. 9. The method of claim 8,
The organic material layer containing the compound is an organic light emitting auxiliary layer. 9. The method of claim 8,
The organic material layer containing the compound is an organic electroluminescent device that is a hole transport layer.