KR102154878B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel tertiary substituted benzene-based compound excellent in hole injection, transport and luminescence ability, and an organic electroluminescent device comprising the same, wherein the compound according to the present invention is used in an organic material layer, preferably a light-emitting layer of an organic electroluminescent device. Accordingly, the luminous efficiency, driving voltage, and lifespan of the organic electroluminescent device can be improved.

Description

An organic light-emitting compound and an organic electroluminescent device comprising the same TECHNICAL FIELD {ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING THE SAME}

The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device including the same, and more particularly, a novel tertiary substituted benzene-based compound having excellent hole injection, transport and luminescence ability, and by including the same in one or more organic material layers, light emission It relates to an organic electroluminescent device having improved characteristics such as efficiency, driving voltage, and lifetime.

The study of organic electroluminescent (EL) devices (hereinafter simply referred to as'organic EL devices') followed by blue electroluminescence using an anthracene single crystal in 1965 from the observation of Bernanose's organic thin-film emission in the 1950s In 1987, by Tang, an organic EL device having a stacked structure divided into a functional layer of a hole layer and a light emitting layer was proposed. Since then, in order to make a high-efficiency, high-life organic EL device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used for this.

In an organic EL device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. In this case, 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.

The material for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the light emission color. In addition, yellow and orange light emitting materials are also used to realize better natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material.

The dopant material can be classified into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. In this case, since the phosphorescent material can theoretically improve the luminous efficiency of up to four times compared to the fluorescent material, a lot of research has been conducted on phosphorescent host materials as well as phosphorescent dopants.

To date, as the hole injection layer, the hole transport layer, the hole blocking layer, and the electron transport layer, NPB, BCP, Alq _3, etc., represented by the following formulas are widely known, and anthracene derivatives are reported as fluorescent dopant/host materials as light emitting materials. . In particular, as phosphorescent materials that have a great advantage in terms of efficiency improvement among light-emitting materials, metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ and (acac)Ir(btp) ₂ are used as blue, green, and red dopant materials. Is being used. Until now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, conventional materials have an advantage in terms of light emission characteristics, but due to low glass transition temperature and low thermal stability, they are not at a satisfactory level in terms of lifespan of an organic electroluminescent device.

Republic of Korea Patent Publication 2011-0066763

In order to solve the above problems, an object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and improving bonding strength between holes and electrons.

In addition, an object of the present invention is to provide an organic electroluminescent device including the organic compound and exhibiting a low driving voltage and high luminous efficiency.

[화학식 4]

[화학식 5]

[화학식 6]

[화학식 7]

상기 화학식 3 내지 화학식 7에서,
Ar₁은 하기 A-1 내지 A-15 중 어느 하나로 표시되는 치환체이고,
Y₁은 O 또는 S이고;
Z₁은 단일결합, C(R₁₁)(R₁₂), N(R₁₃), O 및 S로 구성된 군에서 선택되고;
L₁은 단일결합, 치환 또는 비치환된 C₆~C₄₀의 아릴렌기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되고;
L₂는 단일결합이거나, 치환 또는 비치환된 C₆~C₄₀의 아릴렌기이고;
R₁ 내지 R₈ 및 R₁₀ 내지 R₁₃은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C₁~C₄₀의 알킬기, C₂~C₄₀의 알케닐기, C₂~C₄₀의 알키닐기, C₆~C₄₀의 아릴기, 핵원자수 5 내지 40개의 헤테로아릴기, C₆~C₄₀의 아릴옥시기, C₁~C₄₀의 알킬옥시기, C₆~C₄₀의 아릴아민기, C₃~C₄₀의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C₁~C₄₀의 알킬실릴기, C₁~C₄₀의 알킬보론기, C₆~C₄₀의 아릴보론기, C₆~C₄₀의 아릴포스핀기, C₆~C₄₀의 모노 또는 디아릴포스피닐기 및 C₆~C₄₀의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고;
R₉는 C₆~C₄₀의 아릴기이며;
상기 R₁ 내지 R₈ 및 R₁₀ 내지 R₁₃의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 모노 또는 디아릴포스피닐기 및 아릴실릴기와 R₉의 아릴기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C₁~C₄₀의 알킬기, C₂~C₄₀의 알케닐기, C₂~C₄₀의 알키닐기, C₆~C₄₀의 아릴기, 핵원자수 5 내지 40개의 헤테로아릴기, C₆~C₄₀의 아릴옥시기, C₁~C₄₀의 알킬옥시기, C₆~C₄₀의 아릴아민기, C₃~C₄₀의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C₁~C₄₀의 알킬실릴기, C₁~C₄₀의 알킬보론기, C₆~C₄₀의 아릴보론기, C₆~C₄₀의 아릴포스핀기, C₆~C₄₀의 모노 또는 디아릴포스피닐기 및 C₆~C₄₀의 아릴실릴기로 이루어진 군에서 선택된 1종 이상으로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;
m은 0 내지 4의 정수로서, m이 0인 경우 수소가 치환기 R₁₀으로 치환되지 않은 것을 의미하고, m이 2 내지 4의 정수인 경우, 복수 개의 R₁₀은 각각 동일하거나 상이하다.

상기 A-1 내지 A-15에서,
L3는 단일결합, 치환 또는 비치환된 C₆~C₄₀의 아릴렌기 및 치환 또는 비치환된 핵원자수 5 내지 40개의 헤테로아릴렌기로 이루어진 군에서 선택되고;
R₁₄는 수소, 중수소, 할로겐, 시아노기, C₁~C₄₀의 알킬기, C₂~C₄₀의 알케닐기, C₂~C₄₀의 알키닐기, C₆~C₄₀의 아릴기, 핵원자수 5 내지 40개의 헤테로아릴기, C₆~C₄₀의 아릴옥시기, C₁~C₄₀의 알킬옥시기, C₆~C₄₀의 아릴아민기, C₃~C₄₀의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C₁~C₄₀의 알킬실릴기, C₁~C₄₀의 알킬보론기, C₆~C₄₀의 아릴보론기, C₆~C₄₀의 아릴포스핀기, C₆~C₄₀의 모노 또는 디아릴포스피닐기 및 C₆~C₄₀의 아릴실릴기로 이루어진 군에서 선택되고, 상기 복수 개의 R₁₄ 중 수소가 아닌 것은 2개 이상이며;
상기 R₁₄의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C₁~C₄₀의 알킬기, C₂~C₄₀의 알케닐기, C₂~C₄₀의 알키닐기, C₆~C₄₀의 아릴기 및 C₃~C₄₀의 시클로알킬기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며,
R₂₁은 수소, 중수소(D), 할로겐, 시아노기, 치환 또는 비치환된 C₁~C₄₀의 알킬기, 치환 또는 비치환된 C₆~C₄₀의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C₆~C₄₀의 아릴옥시기, 치환 또는 비치환된 C₁~C₄₀의 알킬옥시기, 치환 또는 비치환된 C₆~C₄₀의 아릴아민기, 치환 또는 비치환된 C₁~C₄₀의 알킬실릴기, 치환 또는 비치환된 C₁~C₄₀의 알킬보론기, 치환 또는 비치환된 C₆~C₄₀의 아릴보론기, 치환 또는 비치환된 C₆~C₄₀의 아릴포스핀기, 치환 또는 비치환된 C₆~C₄₀의 모노 또는 디아릴포스피닐기 및 치환 또는 비치환된 C₆~C₄₀의 아릴실릴기로 이루어진 군에서 선택되며;In order to achieve the above object, the present invention provides a compound represented by the following formulas 3 to 7.
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 7,
Ar ₁ is a substituent represented by any one of the following A-1 to A-15,
Y ₁ is O or S;
Z ₁ is a single bond, selected from the group consisting of C(R ₁₁ )(R ₁₂ ), N(R ₁₃ ), O and S;
L ₁ is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ to C ₄₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
L ₂ is a single bond, or a substituted or unsubstituted C ₆ ~C ₄₀ arylene group;
R ₁ to R ₈ and R ₁₀ to R ₁₃ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, 5 to 40 nuclear atoms heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ mono or diarylphosphine group and C ₆ ~ C ₄₀ selected from the group consisting of arylsilyl group, or combined with an adjacent group Forming a condensed ring;
R ₉ is a C ₆ ~ C ₄₀ aryl group;
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of the R ₁ to R ₈ and R ₁₀ to R ₁₃ , Alkyl boron group, aryl boron group, arylphosphine group, mono or diarylphosfinyl group and arylsilyl group and the aryl group of R ₉ are each independently deuterium, halogen, cyano 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, 5 to 40 nuclear atoms heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ mono or diarylphosphine group and C ₆ ~ C ₄₀ arylsilyl group When substituted or unsubstituted with one or more selected from the group, and substituted with a plurality of substituents, they are the same as or different from each other;
m is an integer of 0 to 4, and when m is 0, it means that hydrogen is not substituted with a substituent R ₁₀ , and when m is an integer of 2 to 4, a plurality of R _10s are the same or different, respectively.

In the above A-1 to A-15,
L3 is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ ~ C ₄₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
R ₁₄ is hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom number 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl boron groups, C ₆ to C ₄₀ aryl boron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ ~ C ₄₀ mono or is selected from diaryl phosphine blood group and an aryl silyl group consisting of a C ₆ ~ C ₄₀ of, Two or more of the plurality of R ₁₄ are not hydrogen;
Alkyl group of the R _14, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alky When substituted or unsubstituted with one or more substituents selected from the group consisting of a nil group, a C ₆ ~ C ₄₀ aryl group and a C ₃ ~ C ₄₀ cycloalkyl group, and when substituted with a plurality of substituents, they are the same or different from each other,
R ₂₁ is hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted nuclear atom number 5 to 40 heteroaryl group, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ aryl An amine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ mono or diaryl the Phosphinicosuccinic group and a substituted or unsubstituted C ₆ ~ C ₄₀ selected from the group consisting arylsilyl of Become;

n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₁₀ , and when n is an integer of 2 to 4, a plurality of R _10s are the same or different, respectively.

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According to a preferred embodiment of the present invention, the substituent linked to L ₁ in the compounds represented by Chemical Formulas 3 to 7 is dibenzo[b,d]furan or dibenzothiophene (dibenzo[b, d]thiophene).

According to a preferred embodiment of the present invention, the substituents linked to L ₂ in the compounds represented by Formulas 3 to 7 are carbazole, phenoxazine, phenothiazine, and phenazine ( phenazine) and acridine may be any one selected from the group consisting of.

In addition, the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode, at least one of the one or more organic material layers Provides an organic electroluminescent device including the compound represented by Chemical Formulas 3 to 7.

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Here, the organic material layer including the compound of Formulas 3 to 7 may be a phosphorescent emission layer.

"Alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.

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

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

In the present invention, "aryl" refers to 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, a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.

In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms 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 of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and R means an aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

"Alkyloxy" in the present invention is a monovalent substituent represented by R'O-, wherein R'refers to an alkyl having 1 to 40 carbon atoms, and is linear, branched, or cyclic. It can contain structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

"Arylamine" in the present invention means an amine substituted with an aryl having 6 to 60 carbon atoms.

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

"Heterocycloalkyl" in the present invention 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, Substituted by a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, "alkylsilyl" refers to silyl substituted with an alkyl having 1 to 40 carbon atoms, and "arylsilyl" refers to silyl substituted with an aryl having 5 to 40 carbon atoms.

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

Since the compound according to the present invention has excellent thermal stability and phosphorescence properties, it can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound according to the present invention is used as a phosphorescent host material, it is possible to manufacture an organic electroluminescent device having excellent luminescence performance, low driving voltage, high efficiency, and long life compared to a conventional host material, and furthermore, the performance and lifespan are large. Advanced full-color display panels can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The present invention provides a novel tertiary substituted benzene-based compound having a higher molecular weight than the conventional material for an organic EL device [eg, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)] and having excellent driving voltage characteristics and efficiency do.

[화학식 4]

[화학식 5]

[화학식 6]

[화학식 7]The novel tertiary substituted benzene-based compound of the present invention can be represented by the following Chemical Formulas 3 to 7.
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

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In Formulas 3 to 7, Ar ₁ is a substituent represented by any one of the following A-1 to A-15,

Y ₁ is O or S;

Z ₁ is a single bond, selected from the group consisting of C(R ₁₁ )(R ₁₂ ), N(R ₁₃ ), O and S;

L ₁ is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ ~ C ₄₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms, preferably a single bond or a phenylene group , Biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinylene group, pyrrolylene group, imida It is selected from the group consisting of a zolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group and a pyrimidinylene group, and more preferably, a single bond, a phenylene group, and a biphenylene group. There is;

상기 A-1 내지 A-15에서,
L3는 단일결합, 치환 또는 비치환된 C₆~C₄₀의 아릴렌기 및 치환 또는 비치환된 핵원자수 5 내지 40개의 헤테로아릴렌기로 이루어진 군에서 선택되고;
R₁₄는 수소, 중수소, 할로겐, 시아노기, C₁~C₄₀의 알킬기, C₂~C₄₀의 알케닐기, C₂~C₄₀의 알키닐기, C₆~C₄₀의 아릴기, 핵원자수 5 내지 40개의 헤테로아릴기, C₆~C₄₀의 아릴옥시기, C₁~C₄₀의 알킬옥시기, C₆~C₄₀의 아릴아민기, C₃~C₄₀의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C₁~C₄₀의 알킬실릴기, C₁~C₄₀의 알킬보론기, C₆~C₄₀의 아릴보론기, C₆~C₄₀의 아릴포스핀기, C₆~C₄₀의 모노 또는 디아릴포스피닐기 및 C₆~C₄₀의 아릴실릴기로 이루어진 군에서 선택되고, 상기 복수 개의 R₁₄ 중 수소가 아닌 것은 2개 이상이며;
상기 R₁₄의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C₁~C₄₀의 알킬기, C₂~C₄₀의 알케닐기, C₂~C₄₀의 알키닐기, C₆~C₄₀의 아릴기 및 C₃~C₄₀의 시클로알킬기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며,
R₂₁은 수소, 중수소(D), 할로겐, 시아노기, 치환 또는 비치환된 C₁~C₄₀의 알킬기, 치환 또는 비치환된 C₆~C₄₀의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C₆~C₄₀의 아릴옥시기, 치환 또는 비치환된 C₁~C₄₀의 알킬옥시기, 치환 또는 비치환된 C₆~C₄₀의 아릴아민기, 치환 또는 비치환된 C₁~C₄₀의 알킬실릴기, 치환 또는 비치환된 C₁~C₄₀의 알킬보론기, 치환 또는 비치환된 C₆~C₄₀의 아릴보론기, 치환 또는 비치환된 C₆~C₄₀의 아릴포스핀기, 치환 또는 비치환된 C₆~C₄₀의 모노 또는 디아릴포스피닐기 및 치환 또는 비치환된 C₆~C₄₀의 아릴실릴기로 이루어진 군에서 선택되며;
n은 0 내지 4의 정수로서, n이 0인 경우, 수소가 치환기 R₁₀으로 치환되지 않은 것을 의미하고, n이 2 내지 4의 정수인 경우, 복수 개의 R₁₀은 각각 동일하거나 상이함하다.L ₂ is a single bond, or a substituted or unsubstituted C ₆ ~C ₄₀ arylene group;
R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphinyl group and C ₆ ~ C ₄₀ selected from the group consisting of arylsilyl group, but does not form a condensed ring by bonding with adjacent groups ;
R ₁₀ to R ₁₃ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ mono or diarylphosphinyl group and C ₆ ~ C ₄₀ selected from the group consisting of arylsilyl group, or combined with an adjacent group to form a condensed ring;
R ₉ is a C ₆ ~ C ₄₀ aryl group;
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of the R ₁ to R ₈ and R ₁₀ to R ₁₃ , Alkyl boron group, aryl boron group, arylphosphine group, mono or diarylphosfinyl group and arylsilyl group and the aryl group of R ₉ are each independently deuterium, halogen, cyano 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, 5 to 40 nuclear atoms heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ mono or diarylphosphine group and C ₆ ~ C ₄₀ arylsilyl group When substituted or unsubstituted with one or more selected from the group, and substituted with a plurality of substituents, they are the same as or different from each other;
m is an integer of 0 to 4, and when m is 0, it means that hydrogen is not substituted with a substituent R ₁₀ , and when m is an integer of 2 to 4, a plurality of R _10s are the same or different, respectively.

In the above A-1 to A-15,
L3 is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ ~ C ₄₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
R ₁₄ is hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom number 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl boron groups, C ₆ to C ₄₀ aryl boron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ ~ C ₄₀ mono or is selected from diaryl phosphine blood group and an aryl silyl group consisting of a C ₆ ~ C ₄₀ of, Two or more of the plurality of R ₁₄ are not hydrogen;
Alkyl group of the R _14, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alky When substituted or unsubstituted with one or more substituents selected from the group consisting of a nil group, a C ₆ ~ C ₄₀ aryl group and a C ₃ ~ C ₄₀ cycloalkyl group, and when substituted with a plurality of substituents, they are the same or different from each other,
R ₂₁ is hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted nuclear atom number 5 to 40 heteroaryl group, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ aryl An amine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ mono or diaryl the Phosphinicosuccinic group and a substituted or unsubstituted C ₆ ~ C ₄₀ selected from the group consisting arylsilyl of Become;
n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₁₀ , and when n is an integer of 2 to 4, a plurality of R _10s are the same or different, respectively.

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In order to obtain highly efficient phosphorescent light emission, energy transfer from the host to the dopant is important. When the host has a triplet energy greater than that of the dopant, the energy transferred to the dopant is prevented from being reversed to the host, thereby providing high light emission efficiency.

Accordingly, the compound of the present invention is a form in which each moiety is bonded in three directions around benzene, and may have a higher triplet energy than a compound bonded linearly, and thereby exciton transition to a dopant is It is easy, and it is also easy from the viewpoint of confining excitons generated in the emission layer, and when used in the emission layer, luminous efficiency can be increased.

In addition, in the compound of the present invention, the substituent connected to benzene by L ₁ has a property of an electron donating group (EDG) with large electron donating, and the substituent connected to benzene by L ₂ is an electron withdrawing group having high electron absorption. (electron withdrawing group, EWG), so it has both an electron withdrawing group (EWG) with high electron absorption and an electron donating group (EDG) with large electron donation in one compound. The whole exhibits bipolar characteristics. For this reason, the compound of the present invention not only has a wide band gap, but also can increase the bonding strength between holes and electrons. Accordingly, it is possible to improve the phosphorescent characteristics of the organic EL device and at the same time improve the carrier injection capability, transport capability, or luminous efficiency.

In addition, the compound of the present invention is the conventional CBP (4,4-dicarbazolybiphenyl) as the glass transition temperature is improved by significantly increasing the molecular weight of the compound due to the bonding of an aromatic ring or a heteroaromatic ring. ), and is effective in inhibiting crystallization of the organic material layer due to the asymmetric structure.

Therefore, when the compound of the present invention is used as a material for a hole injection layer, a hole transport layer, or a light emitting layer of an organic electroluminescent device, the efficiency and lifespan of the organic electroluminescent device can be improved compared to a conventional organic material layer material (for example, CBP). have. In addition, the improvement of the lifespan of the organic electroluminescent device can maximize the performance of the full-color organic light emitting panel.

According to a preferred embodiment of the present invention, the substituent linked by L ₁ is dibenzo[b,d]furan or dibenzothiophene (dibenzo[b,d]thiophene), and a substituent linked by L ₂ Is any one selected from the group consisting of carbazole, phenoxazine, phenothiazine, phenazine, and acridine, and can further enhance the above effect. .

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The compounds of the present invention may be specifically represented by compounds having the structures illustrated below, but are not limited thereto.

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2. Organic EL device

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) including a compound represented by Formulas 3 to 7 according to the present invention.

More specifically, the organic electroluminescent device according to 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 May include a compound represented by Chemical Formulas 3 to 7. In this case, the compound may be used alone, or two or more may be used in combination.

The one or more organic material layers may be at least one of a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer. Here, it is preferable that the organic material layer including the compound represented by Chemical Formulas 3 to 7 is an emission layer.

The emission layer of the organic electroluminescent device of the present invention may include a host material, and in this case, a compound represented by Chemical Formulas 3 to 7 may be included as the host material. When the compounds represented by Chemical Formulas 3 to 7 are included as a material for an emission layer of an organic electroluminescent device, preferably as a phosphorescent host material of blue, green, and red, since the bonding force between holes and electrons in the emission layer increases, organic electroluminescence It is possible to improve the efficiency (luminescence efficiency and power efficiency), lifespan, luminance and driving voltage of the device. Specifically, the compounds represented by Chemical Formulas 3 to 7 are preferably included in the organic electroluminescent device as green and/or red phosphorescent host, fluorescent host, or dopant material.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. An electron injection layer may be additionally stacked on the electron transport layer.

In addition, the structure of the organic electroluminescent device of the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (e.g., the emission layer) is formed to include the compound represented by Chemical Formulas 3 to 7. Thus, it can be manufactured by forming another organic material layer and an electrode.

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

As a substrate included in the organic electroluminescent device of the present invention, a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet, and the like may be used.

In addition, the anode material may 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 SnO ₂ :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black may be used, but is not limited thereto.

In addition, as the anode material, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof, and multilayers such as LiF/Al or LiO ₂ /Al A structural material or the like may be used, but is not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used. Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of CDT-1

<Step 1> Synthesis of 3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole

23.9 g (50.0 mmol) 3-(3,5-dibromophenyl)-9-phenyl-9H-carbazole, 11.4 g (50.0 mmol) dibenzo[b,d]thiophene-4 under a nitrogen stream -Ilboronic acid, 6.0 g (150.0 mmol) of NaOH, 2.89 g (5 mol%) of Pd(PPh ₃ ) ₄ were added to 250 ml / 120 ml of THF/H ₂ O and stirred at 90° C. for 12 hours . After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H, was used by column chromatography. -Carbazole (21.0 g, 36.1 mmol, 72% yield) was obtained.

Mass: [(M+H) ⁺ ]: 582, 580

Elemental Analysis: C, 74.48; H, 3.82; Br, 13.76; N, 2.41; S, 5.52

<Step 2> Synthesis of CDT-1

3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole 17.4 g (30.0 mmol) and 4,4 under a nitrogen stream 4',4',5,5,5',5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 9.11 g (36.0 mmol), Pd(dppf)Cl ₂ 1.0 g (5 mol %), KOAc 8.79 g (90.0 mmol), 400 ml of 1,4-dioxane were added, stirred at 110° C. for 12 hours, the reaction was terminated, extracted with methylene chloride, and water was removed with MgSO ₄ I did. The reaction product from which the solvent was removed was subjected to column chromatography to obtain CDT-1 (16.6 g, 26.4 mmol, yield 88%) as the target compound.

Mass: [(M+H) ⁺ ]: 628

¹ H-NMR: δ 1.23 (s, 12H), 7.16 (t, 1H), 7.35 (t, 1H), 7.52 (m, 5H), 7.61 (m, 2H), 7.70 (m, 4H), 7.93 ( m, 5H), 8.32 (d, 1H), 8.52 (m, 3H)

[Preparation Example 2] Synthesis of CDT-2

<Step 1> Synthesis of 3-(3-bromo-5-(dibenzo[b,d]-thiophen-2-yl)phenyl)-9-phenyl-9H-carbazole

<Step 1 of Preparation Example 1, except that dibenzo[b,d]thiophen-2-ylboronic acid (11.4 g, 50.0 mmol) was used instead of dibenzo[bd]thiophen-4-ylboronic acid. > 3-(3-bromo-5-(dibenzo[b,d]-thiophen-2-yl)phenyl)-9-phenyl-9H-carbazole (18.9 g, 32.5 mmol , Yield 65%).

Mass: [(M+H) ⁺ ]: 582, 580

Elemental Analysis: C, 74.48; H, 3.82; Br, 13.76; N, 2.41; S, 5.52

<Step 2> Synthesis of CDT-2

3-(3-bromo-5-(dibenzo[b,d]-thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole instead of 3-(3-bromo-5-(di The same procedure as in <Step 2> of Preparation Example 1 except that benzo[b,d]-thiophen-2-yl)phenyl)-9-phenyl-9H-carbazole (17.4 g, 30.0 mmol) was used. CDT-2 (14.0 g, 22.3 mmol, yield 74%) was obtained.

Mass: [(M+H) ⁺ ]: 628

¹ H-NMR: δ 1.23 (s, 12H), 7.17 (t, 1H), 7.36 (t, 1H), 7.52 (m, 5H), 7.63 (m, 2H), 7.71 (m, 3H), 7.94 ( m, 6H), 8.12 (m, 2H), 8.50 (m, 2H)

[Preparation Example 3] Synthesis of CDT-3

<Step 1> Synthesis of 3-(3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9-phenyl-9H-carbazole

<Step of Preparation Example 1 except that dibenzo[b,d]furan-4-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. Perform the same procedure as 1> to 3-(3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9-phenyl-9H-carbazole (22.1 g, 39.2 mmol, Yield 78%).

Mass: [(M+H) ⁺ ]: 564, 566

Elemental Analysis: C, 76.60; H, 3.93; Br, 14.16; N, 2.48; O, 2.83

<Step 2> Synthesis of CDT-3

3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole instead of 3-(3-bromo-5-(dibenzo Except for using [b,d]furan-4-yl)phenyl)-9-phenyl-9H-carbazole (17.0 g, 30.0 mmol), the same procedure as in <Step 2> of Preparation Example 1 was performed. CDT-3 (14.1 g, 23.1 mmol, 77% yield) was obtained.

Mass: [(M+H) ⁺ ]: 612

¹ H-NMR: δ 1.23 (s, 12H), 7.16 (t, 1H), 7.35 (m, 3H), 7.52 (m, 5H), 7.62 (m, 2H), 7.77 (m, 3H), 7.94 ( m, 4H), 8.02 (m, 3H), 8.51 (d, 1H)

[Preparation Example 4] Synthesis of CDT-4

<Step 1> Synthesis of 3-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9-phenyl-9H-carbazole

<Step of Preparation Example 1 except that dibenzo[b,d]furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. Perform the same procedure as in 1> 3-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9-phenyl-9H-carbazole (18.5 g, 32.8 mmol, Yield 66%).

Mass: [(M+H) ⁺ ]: 564, 566

Elemental Analysis: C, 76.60; H, 3.93; Br, 14.16; N, 2.48; O, 2.83

<Step 2> Synthesis of CDT-4

3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole instead of 3-(3-bromo-5-(dibenzo Except for using [b,d]furan-2-yl)phenyl)-9-phenyl-9H-carbazole (17.0 g, 30.0 mmol), the same procedure as in <Step 2> of Preparation Example 1 was performed. CDT-4 (13.4 g, 21.9 mmol, yield 73%) was obtained.

Mass: [(M+H) ⁺ ]: 612

¹ H-NMR: δ 1.24 (s, 12H), 7.16 (t, 1H), 7.35 (m, 3H), 7.51 (m, 4H), 7.63 (m, 2H), 7.77 (m, 4H), 7.84 ( m, 3H), 8.00 (m, 4H), 8.55 (d, 1H)

[Preparation Example 5] Synthesis of CDT-5

<Step 1> Synthesis of 9-(3,5-dibromophenyl)-9H-carbazole

9H-carbazole (16.7 g, 100.0 mmol), 1,3,5-tribromobenzene (47.1 g, 150.0 mmol), Pd ₂ (dba) ₃ (4.60 g, 5 mol%), (t -Bu) ₃ P (4.00 g, 20.0 mmol), sodium tert-butoxide (28.8 g, 300.0 mmol) was added to 300 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 9-(3,5-dibromophenyl)-9H-carbazole (29.0 g, 72.1 mmol, yield 72%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 402

Elemental Analysis: C, 53.90; H, 2.76; Br, 39.84; N, 3.49

<Step 2> Synthesis of 9-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl-9H-carbazole

Using 9-(3,5-dibromophenyl)-9H-carbazole (20.1 g, 50.0 mmol) instead of 3-(3,5-dibromophenyl)-9-phenyl-9H-carbazole 9-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl-9H-carbazole (16.2) except for the same procedure as in <Step 1> of Preparation Example 1 g, 32.1 mmol, yield 64%) was obtained.

Mass: [(M+H) ⁺ ]: 504, 506

Elemental Analysis: C, 71.43; H, 3.60; Br, 15.84; N, 2.78; S, 6.36

<Step 3> Synthesis of CDT-5

3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole instead of 9-(3-bromo-5-(dibenzo CDT-5 by performing the same procedure as in <Step 2> of Preparation Example 1, except that [b,d]thiophen-4-yl)phenyl)-9H-carbazole (15.2 g, 30.0 mmol) was used. (11.7 g, 21.3 mmol, yield 71%) was obtained.

Mass: [(M+H) ⁺ ]: 552

¹ H-NMR: δ 1.23 (s, 12H), 7.19 (m, 2H), 7.35 (t, 1H), 7.52 (m, 5H), 7.63 (s, 1H), 7.70 (d, 1H), 7.94 ( m, 2H), 8.20 (m, 3H), 8.52 (m, 3H)

[Preparation Example 6] Synthesis of CDT-6

<Step 1> Synthesis of 9-(3-bromo-5-(dibenzo[b,d]thiophen-2-yl)phenyl)-9H-carbazole

Using 9-(3,5-dibromophenyl)-9H-carbazole (20.1 g, 50.0 mmol) instead of 3-(3,5-dibromophenyl)-9-phenyl-9H-carbazole 9-(3-bromo-5-(dibenzo[b,d]thiophen-2-yl)phenyl)-9H-carbazole ( 15.4 g, 30.5 mmol, yield 61%) was obtained.

Mass: [(M+H) ⁺ ]: 504, 506

Elemental Analysis: C, 71.43; H, 3.60; Br, 15.84; N, 2.78; S, 6.36

<Step 2> Synthesis of CDT-6

3-(3-bromo-5-(dibenzo[b,d]-thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole instead of 9-(3-bromo-5-(di CDT-6 was performed in the same manner as in <Step 2> of Preparation Example 1, except that benzo[b,d]thiophen-2-yl)phenyl-9H-carbazole (15.2 g, 30.0 mmol) was used. (13.7 g, 24.8 mmol, 83% yield) was obtained.

Mass: [(M+H) ⁺ ]: 552

¹ H-NMR: δ 1.24 (s, 12H), 7.19 (m, 2H), 7.35 (t, 1H), 7.51 (m, 5H), 7.63 (s, 1H), 7.93 (m, 3H), 8.12 ( m, 3H), 8.21 (s, 1H), 8.51 (m, 2H)

[Preparation Example 7] Synthesis of CDT-7

<Step 1> Synthesis of 9-(3-bromo-5-(dibenzo[b.d]furan-4-yl)phenyl)-9H-carbazole

Using 9-(3,5-dibromophenyl)-9H-carbazole (20.1 g, 50.0 mmol) instead of 3-(3,5-dibromophenyl)-9-phenyl-9H-carbazole 9-(3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9H-carbazole (15.1) by performing the same procedure as in <Step 1> of Preparation Example 3 except g, 30.9 mmol, yield 62%) was obtained.

Mass: [(M+H) ⁺ ]: 488, 490

Elemental Analysis: C, 73.78; H, 3.72; Br, 16.36; N, 2.87; O, 3.28

<Step 2> Synthesis of CDT-7

3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole instead of 9-(3-bromo-5-(dibenzo [b,d] furan-4-yl) phenyl-9H-carbazole (14.7 g, 30.0 mmol) was carried out in the same manner as in <Step 2> of Preparation Example 1, and CDT-7 (11.7 g, 21.9 mmol, yield 73%).

Mass: [(M+H) ⁺ ]: 536

¹ H-NMR: δ 1.24 (s, 12H), 7.20 (m, 3H), 7.36 (t, 1H), 7.54 (m, 4H), 7.64 (s, 1H), 7.85 (m, 3H), 8.02 ( m, 4H), 8.19 (s, 1H), 8.55 (d, 1H)

[Preparation Example 8] Synthesis of CDT-8

<Step 1> Synthesis of 9-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9-phenyl-9H-carbazole

Using 9-(3,5-dibromophenyl)-9H-carbazole (20.1 g, 50.0 mmol) instead of 3-(3,5-dibromophenyl)-9-phenyl-9H-carbazole 9-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9-phenyl-9H- by performing the same procedure as in <Step 1> of Preparation Example 4 except for Carbazole (15.3 g, 31.2 mmol, 62% yield) was obtained.

Mass: [(M+H) ⁺ ]: 488, 490

Elemental Analysis: C, 73.78; H, 3.72; Br, 16.36; N, 2.87; O, 3.28

<Step 2> Synthesis of CDT-8

3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole instead of 9-(3-bromo-5-(dibenzo Except for using [b,d]furan-2-yl)phenyl)-9-phenyl-9H-carbazole (14.7 g, 30.0 mmol), the same procedure as in <Step 2> of Preparation Example 1 was performed. CDT-8 (12.1 g, 22.7 mmol, yield 76%) was obtained.

Mass: [(M+H) ⁺ ]: 536

¹ H-NMR: δ 1.24 (s, 12H), 7.19 (m, 2H), 7.36 (m, 2H), 7.54 (m, 4H), 7.65 (s, 1H), 7.85 (m, 2H), 8.00 ( m, 3H), 8.19 (s, 1H), 8.55 (m, 2H)

[Preparation Example 9] Synthesis of CDT-9

<Step 1> Synthesis of 9-(3',5'-dichloro-[1,1'-biphenyl]-3-yl)-9H-carbazole

<Step of Preparation Example 5, except that 3'-bromo-3,5-dichloro-1,1'-biphenyl (45.3 g, 150.0 mmol) was used instead of 1,3,5-tribromobenzene Perform the same procedure as in 1> to obtain 9-(3',5'-dichloro-[1,1'-biphenyl]-3-yl)-9H-carbazole (28.4 g, 73.2 mmol, yield 73%). Got it.

Mass: [(M+H) ⁺ ]: 388

Elemental Analysis: C, 74.24; H, 3.89; Cl, 18.26; N, 3.61

<Step 2> of 9-(3'-chloro-5'-dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole synthesis

19.4 g (50.0 mmol) of 9-(3',5'-dichloro-[1,1'-biphenyl]-3-yl)-9H-carbazole under nitrogen stream, 11.4 g (50.0 mmol) of dibenzo [b,d]thiophene-4-ylboronic acid, 20.7 g (150.0 mmol) of K ₂ CO ₃ , 2.89 g (5 mol%) of Pd(PPh ₃ ) _4, 2.4 g (5.00 mmol) of X- Phos was added to 250 ml / 120 ml of THF/H ₂ O and stirred at 90° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 9-(3'-chloro-5'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-, was used by column chromatography. Biphenyl]-3-yl)-9H-carbazole (16.1 g, 30.1 mmol, yield 60%) was obtained.

Mass: [(M+H) ⁺ ]: 535

Elemental Analysis: C, 80.66; H, 4.14; Cl, 6.61; N, 2.61; S, 5.98

<Step 3> Synthesis of CDT-9

16.0 g of 9-(3'-chloro-5'-dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole under a nitrogen stream (30.0 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane 9.11 g (36.0 mmol) ), Pd(dppf)Cl ₂ 1.0 g (5 mol %), KOAc 8.79 g (90.0 mmol), X-Phos 1.43 g (3.00 mmol), 1,4-Dioxane 400 ml were added and stirred at 110° C. for 12 hours After the reaction was terminated, water was removed by extraction with methylene chloride and MgSO _{4. The} reaction product from which the solvent was removed was subjected to column chromatography to obtain CDT-9 (14.7 g, 23.4 mmol, yield 78%). .

Mass: [(M+H) ⁺ ]: 628

¹ H-NMR: δ 1.25 (s, 12H), 7.19 (m, 2H), 7.35 (t, 1H), 7.55 (m, 5H), 7.64 (m, 2H), 7.72 (m, 3H), 7.95 ( m, 3H), 8.22 (m, 2H), 8.29 (d, 1H), 8.55 (m, 3H)

[Preparation Example 10] Synthesis of ADT-1

<Step 1> Synthesis of 2-(3,5-dibromophenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine

32.9 g (100.0 mmol) of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) boronic acid under nitrogen stream, 47.3 g (150.0 mmol) of 1,3,5 -Tribromobenzene, 12.0 g (300.0 mmol) of NaOH, 5.78 g (5 mol%) of Pd(PPh ₃ ) ₄ were added 500 ml / 180 ml of THF/H ₂ O and stirred at 90° C. for 12 hours I did. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 2-(3,5-dibromophenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine ( 32.3 g, 62.1 mmol, yield 62%) was obtained.

Mass: [(M+H) ⁺ ]: 520

Elemental Analysis: C, 62.45; H, 4.08; Br, 30.77; N, 2.70

<Step 2> 2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine Synthesis of

2-(3,5-dibromophenyl)-9,9-dimethyl-10-phenyl-9,10-di instead of 3-(3,5-dibromophenyl)-9-phenyl-9H-carbazole 2-(3-bromo-5-(dibenzo[b,d]) by performing the same procedure as in <Step 1> of Preparation Example 1, except that hydroacridine (26.0 g, 50.0 mmol) was used. Thiophen-4-yl)phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (19.8 g, 31.8 mmol, yield 63%) was obtained.

Mass: [(M+H) ⁺ ]: 622, 624

Elemental Analysis: C, 75.23; H, 4.53; Br, 12.83; N, 2.25; S, 5.15

<Step 3> Synthesis of ADT-1

2-(3-bromo-5-(dibenzo) instead of 3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9-phenyl-9H-carbazole Preparation example except for the use of [b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (18.7 g, 30.0 mmol) The same procedure as in <Step 2> of 1 was performed to obtain ADT-1 (16.6 g, 24.7 mmol, 82% yield).

Mass: [(M+H) ⁺ ]: 670

¹ H-NMR: δ 1.24 (s, 12H), 1.69 (s, 6H), 7.01 (m, 4H), 7.14 (m, 3H), 7.24 (m, 2H), 7.35 (d, 1H), 7.45 ( m, 3H), 7.72 (m, 4H), 8.01 (m, 2H), 8.32 (d, 1H), 8.46 (m, 2H)

[Preparation Example 11] Synthesis of ADT-2

<Step 1> 2-(3-bromo-5-(dibenzo[b,d]thiophen-2-yl)phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine Synthesis of

Except for using dibenzo[b,d]thiophen-2-ylboronic acid (11.4 g, 50.0 mmol) instead of dibenzo[b,d]thiophen-4-ylboronic acid, the < 2-(3-bromo-5-(dibenzo[b,d]thiophen-2-yl)phenyl-9,9-dimethyl-10-phenyl-9,10- by performing the same procedure as in step 2> Dihydroacridine (19.4 g, 31.1 mmol, 62% yield) was obtained.

Mass: [(M+H) ⁺ ]: 622, 624

Elemental Analysis: C, 75.23; H, 4.53; Br, 12.83; N, 2.25; S, 5.15

<Step 2> Synthesis of ADT-2

2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 2-( 3-bromo-5-(dibenzo[b,d]thiophen-2-yl)phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (18.7 g, 30.0 mmol) ADT-2 (15.4 g, 23.0 mmol, yield 77%) was obtained by performing the same procedure as in <Step 3> of Preparation Example 10 except for using.

Mass: [(M+H) ⁺ ]: 670

¹ H-NMR: δ 1.25 (s, 12H), 1.68 (s, 6H), 7.02 (m, 4H), 7.14 (m, 3H), 7.25 (m, 2H), 7.36 (d, 1H), 7.51 ( m, 3H), 7.77 (m, 4H), 8.01 (m, 2H), 8.12 (m, 2H), 8.46 (d, 1H)

[Preparation Example 12] Synthesis of ADT-3

<Step 1> 2-(3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine Synthesis of

<Step of Preparation Example 10, except that dibenzo[b,d]purin-4-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. 2-(3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-di Hydroacridine (18.8 g, 30.9 mmol, 62% yield) was obtained.

Mass: [(M+H) ⁺ ]: 606, 608

Elemental Analysis: C, 77.23; H, 4.65; Br, 13.17; N, 2.31; O, 2.64

<Step 2> Synthesis of ADT-3

2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 2-( 3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (18.2 g, 30.0 mmol) ADT-3 (15.2 g, 23.2 mmol, yield 77%) was obtained by performing the same procedure as in <Step 3> of Preparation Example 10, except for using.

Mass: [(M+H) ⁺ ]: 654

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 7.08 (m, 4H), 7.14 (m, 4H), 7.25 (m, 2H), 7.36 (d, 1H), 7.52 ( m, 4H), 7.77 (m, 3H), 8.01 (s, 1H), 8.12 (m, 2H), 8.45 (d, 1H)

[Preparation Example 13] Synthesis of ADT-4

<Step 1> 2-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine Synthesis of

<Step of Preparation Example 10, except that dibenzo[b,d]furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. 2-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-di Hydroacridine (20.0 g, 32.9 mmol, yield 66%) was obtained.

Mass: [(M+H) ⁺ ]: 606, 608

Elemental Analysis: C, 77.23; H, 4.65; Br, 13.17; N, 2.31; O, 2.64

<Step 2> Synthesis of ADT-4

2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 2-( 3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (18.2 g, 30.0 mmol) ADT-3 (13.0 g, 19.8 mmol, yield 66%) was obtained by performing the same procedure as in <Step 3> of Preparation Example 10 except for using.

Mass: [(M+H) ⁺ ]: 654

¹ H-NMR: δ 1.25 (s, 12H), 1.68 (s, 6H), 7.10 (m, 4H), 7.19 (m, 4H), 7.25 (m, 2H), 7.37 (d, 1H), 7.52 ( m, 5H), 7.75 (m, 2H), 8.00 (s, 1H), 8.12 (m, 2H), 8.45 (d, 1H)

[Preparation Example 14] Synthesis of ADT-5

<Step 1> Synthesis of 10-(3,5-dibromophenyl)-9,9-dimethyl-9,10-dihydroacridine

Except for using 9,9-dimethyl-9,10-dihydroacridine (20.9 g, 100.0 mmol) instead of 9H-carbazole, the same procedure as in <Step 1> of Preparation Example 5 was carried out to 10- (3,5-dibromophenyl)-9,9-dimethyl-9,10-dihydroacridine (23.5 g, 58.4 mmol, yield 58%) was obtained.

Mass: [(M+H) ⁺ ]: 402

Elemental Analysis: C, 53.90; H, 2.76; Br, 39.84; N, 3.49

<Step 2> Synthesis of 10-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine

2-(3,5-dibromophenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 10-(3,5-dibromophenyl)-9,9- Except for the use of dimethyl-9,10-dihydroacridine (20.1 g, 50.0 mmol), the same procedure as in <Step 2> of Preparation Example 10 was performed to obtain 10-(3-bromo-5-( Dibenzo[b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine (16.4 g, 30.0 mmol, yield 60%) was obtained.

Mass: [(M+H) ⁺ ]: 546, 548

Elemental Analysis: C, 72.52; H, 4.43; Br, 14.62; N, 2.56; S, 5.87

<Step 3> Synthesis of ADT-5

2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 10- (3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine (16.4 g, 30.0 mmol) was used ADT-5 (14.0 g, 23.6 mmol, 79% yield) was obtained by performing the same procedure as in <Step 3> of Preparation Example 10 except for that.

Mass: [(M+H) ⁺ ]: 594

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.95 (t, 2H), 7.15 (m, 6H), 7.22 (m, 2H), 7.33 (s, 1H), 7.47 ( t, 1H), 7.56 (t, 1H), 7.72 (t, 1H), 8.00 (d, 1H), 8.32 (d, 1H), 8.48 (m, 2H)

[Preparation Example 15] Synthesis of ADT-6

<Step 1> Synthesis of 10-(3-bromo-5-(dibenzo[b,d]thiophen-2-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine

Except for using dibenzo[b,d]thiophen-2-ylboronic acid (11.4 g, 50.0 mmol) instead of dibenzo[b,d]thiophen-4-ylboronic acid, the < Perform the same procedure as in Step 2> to obtain 10-(3-bromo-5-(dibenzo[b,d]thiophen-2-yl)phenyl)-9,9-dimethyl-9,10-dihydroa Cridine (18.4 g, 33.6 mmol, yield 67%) was obtained.

Mass: [(M+H) ⁺ ]: 546, 548

Elemental Analysis: C, 72.52; H, 4.43; Br, 14.62; N, 2.56; S, 5.87

<Step 2> Synthesis of ADT-6

2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 10- (3-bromo-5-(dibenzo[b,d]thiophen-2-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine (16.4 g, 30.0 mmol)) ADT-6 (12.2 g, 20.5 mmol, yield 68%) was obtained by performing the same procedure as in <Step 3> of Preparation Example 10 except for using.

Mass: [(M+H) ⁺ ]: 594

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.96 (t, 2H), 7.18 (m, 6H), 7.22 (m, 2H), 7.33 (s, 1H), 7.48 ( t, 1H), 7.56 (t, 1H), 7.73 (t, 1H), 8.00 (d, 1H), 8.12 (m, 2H), 8.48 (d, 1H)

[Preparation Example 16] Synthesis of ADT-7

<Step 1> Synthesis of 10-(3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine

<Step of Preparation Example 14, except that dibenzo[b,d]furan-4-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. 2-(3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine (16.1 g, 30.4 mmol, yield 61%) was obtained.

Mass: [(M+H) ⁺ ]: 530, 532

Elemental Analysis: C, 74.72; H, 4.56; Br, 15.06; N, 2.64; O, 3.02

<Step 2> Synthesis of ADT-7

2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 10- (3-bromo-5-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine (15.9 g, 30.0 mmol) Except that, ADT-7 (12.2 g, 21.1 mmol, yield 70%) was obtained by performing the same procedure as in <Step 3> of Preparation Example 10.

Mass: [(M+H) ⁺ ]: 578

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.96 (t, 2H), 7.18 (m, 6H), 7.25 (m, 2H), 7.33 (m, 3H), 7.50 ( m, 2H), 8.01 (m, 2H), 8.08 (d, 1H)

[Preparation Example 17] Synthesis of ADT-8

<Step 1> Synthesis of 10-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine

<Step of Preparation Example 14, except that dibenzo[b,d]furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. 2> Perform the same procedure as 10-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl-9,9-dimethyl-9,10-dihydroacridine ( 16.4 g, 30.9 mmol, yield 62%) was obtained.

Mass: [(M+H) ⁺ ]: 530, 532

Elemental Analysis: C, 74.72; H, 4.56; Br, 15.06; N, 2.64; O, 3.02

<Step 2> Synthesis of ADT-8

2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 10- (3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine (15.9 g, 30.0 mmol) ADT-8 (14.3 g, 24.7 mmol, 82% yield) was obtained by performing the same procedure as in <Step 3> of Preparation Example 10 except that.

Mass: [(M+H) ⁺ ]: 578

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.96 (t, 2H), 7.17 (m, 6H), 7.23 (m, 2H), 7.33 (m, 3H), 7.54 ( d, 1H), 8.01 (m, 3H), 8.08 (d, 1H)

[Preparation Example 18] Synthesis of ADT-9

<Step 1> Synthesis of 10-(3',5'-dichloro-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9,10-dihydroacridine

Except for using 9,9-dimethyl-9,10-dihydroacridine (10.6 g, 100.0 mmol) instead of 9H-carbazole, the same procedure as in <Step 1> of Preparation Example 9 was carried out to 10- (3',5'-Dichloro-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9,10-dihydroacridine (32.9 g, 76.4 mmol, yield 76%) Got it.

Mass: [(M+H) ⁺ ]: 430

Elemental Analysis: C, 75.35; H, 4.92; Cl, 16.47; N, 3.25

<Step 2> 10-(3'-chloro-5'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9,9- Synthesis of dimethyl-9,10-dihydroacridine

10-(3',5'-dichloro-[1,1'-ratio instead of 9-(3',5',-dichloro-[1,1'-biphenyl]-3-yl)-9H-carbazole Except for using phenyl]-3-yl)-9,9-dimethyl-9,10-dihydroacridine (21.5 g, 50.0 mmol), the same procedure as in <Step 2> of Preparation Example 9 was performed. And 10-(3'-chloro-5'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9 ,10-dihydroacridine (18.0 g, 31.2 mmol, yield 62%) was obtained.

Mass: [(M+H) ⁺ ]: 578

Elemental Analysis: C, 81.02; H, 4.88; Cl, 6.13; N, 2.42; S, 5.55

<Step 3> Synthesis of ADT-9

10-( instead of 9-(3'-chloro-5'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole 3'-chloro-5'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9,10-di ADT-9 (14.1 g, 21.0 mmol, yield 70%) was obtained by performing the same procedure as in <Step 3> of Preparation Example 9, except that hydroacridine (17.3 g, 30.0 mmol) was used.

Mass: [(M+H) ⁺ ]: 670

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.95 (t, 2H), 7.17 (m, 8H), 7.27 (s, 1H), 7.43 (t, 1H), 7.54 ( m, 2H), 7.72 (m, 3H), 8.01 (m, 2H), 8.32 (d, 1H), 8.42 (m, 2H)

[Preparation Example 19] Synthesis of PDT-1

<Step 1> Synthesis of 3-(3,5-dibromophenyl)-10-phenyl-10H-phenothiazine

10-phenyl-3-(4,4,5,5,-tetramethyl-1,3 instead of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) boronic acid ,2-dioxaborolan-2-yl)-10H-phenothiazine (40.1 g, 100.0 mmol) was performed in the same manner as in <Step 1> of Preparation Example 10, except that 3-( 3,5-dibromophenyl)-10-phenyl-10H-phenocyazine (29.9 g, 58.8 mmol, yield 59%) was obtained.

Mass: [(M+H) ⁺ ]: 509

Elemental Analysis: C, 56.60; H, 2.97; Br, 31.38; N, 2.75; S, 6.30

<Step 2> Synthesis of 3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-10-phenyl-10H-phenothiazine

3-(3,5-dibromophenyl)-10-phenyl- instead of 2-(3,5-dibromophenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine Except for using 10H-phenocyazine (25.5 g, 50.0 mmol), the same procedure as in <Step 2> of Preparation Example 10 was carried out to obtain 3-(3-bromo-5-(dibenzo[b,d). ]Thiophen-4-yl)phenyl)-10-phenyl-10H-phenocyazine (18.5 g, 30.2 mmol, yield 60%) was obtained.

Mass: [(M+H) ⁺ ]: 612, 614

Elemental Analysis: C, 70.58; H, 3.62; Br, 13.04; N, 2.29; S, 10.47

<Step 3> Synthesis of PDT-1

2-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridine instead of 3- Preparation except using (3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-10-phenyl-10H-phenocyazine (18.4 g, 30.0 mmol) PDT-1 (16.9 g, 25.6 mmol, yield 85%) was obtained by performing the same procedure as in <Step 3> of Example 10.

Mass: [(M+H) ⁺ ]: 660

¹ H-NMR: δ 1.22 (s, 12H), 7.05 (m, 4H), 7.25 (m, 6H), 7.33 (m, 2H), 7.49 (t, 1H), 7.56 (t, 1H), 7.72 ( m, 3H), 8.01 (m, 2H), 8.32 (d, 1H), 8.47 (m, 2H)

[Preparation Example 20] Synthesis of PDT-2

<Step 1> Synthesis of 3-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-10-phenyl-10H-phenocyazine

<Step of Preparation Example 19, except that dibenzo[b,d]furan-2-ylboronic acid (10.6 g, 50.0 mmol) was used instead of dibenzo[b,d]thiophen-4-ylboronic acid. 2-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-10-phenyl-10H-phenocyazine (20.0 g, 33.5 mmol , Yield 67%) was obtained.

Mass: [(M+H) ⁺ ]: 596, 598

Elemental Analysis: C, 72.48; H, 3.72; Br, 13.39; N, 2.35; O, 2.68; S, 5.37

<Step 2> Synthesis of PDT-2

3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-10-phenyl-10H-phenothiazine instead of 3-(3-bromo-5-(di Except for the use of benzo[b,d]furan-2-yl)phenyl)-10-phenyl-10H-phenocyazine (17.9 g, 30.0 mmol), the same procedure as in <Step 3> of Preparation Example 19 was performed. PDT-2 (12.1 g, 18.9 mmol, yield 63%) was obtained.

Mass: [(M+H) ⁺ ]: 644

¹ H-NMR: δ 1.22 (s, 12H), 7.03 (m, 4H), 7.27 (m, 5H), 7.35 (m, 3H), 7.39 (t, 1H), 7.54 (d, 1H), 7.72 ( m, 3H), 8.01 (m, 3H), 8.32 (m, 2H)

[Preparation Example 21] Synthesis of PDT-3

<Step 1> Synthesis of 3-(3,5-dibromophenyl)-10-phenyl-10H-phenoxazine

10-phenyl-3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazine instead of 10-phenyl-3-(4 ,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine (38.5 g, 100.0 mmol) of Preparation Example 19 except for the use of The same procedure as in <Step 1> was performed to obtain 3-(3,5-dibromophenyl)-10-phenyl-10H-phenoxazine (31.2 g, 63.2 mmol, yield 63%).

Mass: [(M+H) ⁺ ]: 494

Elemental Analysis: C, 58.45; H, 3.07; Br, 32.40; N, 2.84; O, 3.24

<Step 2> Synthesis of 3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-10-phenyl-10H-phenoxazine

3-(3,5-dibromophenyl)-10-phenyl-10H-phenoxazine (24.7 g, 50.0 mmol) instead of 3-(3,5-dibromophenyl)-10-phenyl-10H-phenocyazine ), except for using 3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)- by performing the same procedure as in <Step 2> of Preparation Example 19. 10-phenyl-10H-phenoxazine (18.9 g, 31.7 mmol, yield 64%) was obtained.

Mass: [(M+H) ⁺ ]: 596, 598

Elemental Analysis: C, 72.48; H, 3.72; Br, 13.39; N, 2.35; O, 2.68; S, 5.37

<Step 3> Synthesis of PDT-3

3-(3-bromo-5-(dibenzo[b,d]thiophen-4-yl)phenyl)-10-phenyl-10H-phenothiazine instead of 3-(3-bromo-5-(di Except for using benzo[b,d]thiophen-4-yl)phenyl)-10-phenyl-10H-phenoxazine (17.9 g, 30.0 mmol), the same procedure as in <Step 3> of Preparation Example 19 was performed. PDT-3 (15.6 g, 24.2 mmol, yield 81%) was obtained.

Mass: [(M+H) ⁺ ]: 644

¹ H-NMR: δ 1.22 (s, 12H), 7.03 (m, 4H), 7.28 (m, 5H), 7.35 (m, 2H), 7.39 (t, 1H), 7.55 (d, 1H), 7.72 ( m, 3H), 8.01 (m, 2H), 8.32 (m, 2H), 8.48 (m, 2H)

[Preparation Example 22] Synthesis of PDT-4

<Step 1> Synthesis of 3-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-10-phenyl-10H-phenoxazine

3-(3,5-dibromophenyl)-10-phenyl-10H-phenoxazine (24.7 g, 50.0 mmol) instead of 3-(3,5-dibromophenyl)-10-phenyl-10H-phenocyazine ), except for using 3-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-10 by performing the same procedure as in <Step 1> of Preparation Example 20. -Phenyl-10H-phenoxazine (17.4 g, 30.0 mmol, yield 60%) was obtained.

Mass: [(M+H) ⁺ ]: 580, 582

Elemental Analysis: C, 74.49; H, 3.82; Br, 13.77; N, 2.41; O, 5.51

<Step 2> Synthesis of PDT-4

3-(3-bromo-5-(dibenzo[b,d]furan-2-yl)phenyl)-10-phenyl-10H-phenothiazine instead of 3-(3-bromo-5-(dibenzo Except for using [b,d]furan-2-yl)phenyl)-10-phenyl-10H-phenoxazine (17.4 g, 30.0 mmol), the same procedure as in <Step 2> of Preparation Example 20 was performed. PDT-4 (12.4 g, 19.7 mmol, yield 66%) was obtained.

Mass: [(M+H) ⁺ ]: 628

¹ H-NMR: δ 1.22 (s, 12H), 7.03 (m, 6H), 7.28 (m, 5H), 7.32 (m, 3H), 7.54 (d, 1H), 7.75 (m, 3H), 7.87 ( m, 2H), 8.01 (m, 2H)

[Synthesis Example 1] Synthesis of C 11

6.27 g (10.0 mmol) of CDT-1, 2.67 g (10.0 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.2 g (30.0 mmol) of NaOH under a stream of nitrogen, 0.58 g (5 mol%) of Pd(PPh ₃ ) _{4 was added} to 150 ml / 70 ml of THF/H ₂ O and stirred at 90° C. for 6 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C 11 (5.95 g, yield 81%) was obtained by column chromatography.

Mass: [(M+H) ⁺ ]: 733

[Synthesis Example 2] Synthesis of C 12

Synthesis Example 1 and Synthesis Example 1 except that 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure was performed to obtain the title compound C 12 (6.43 g, yield 88%).

Mass: [(M+H) ⁺ ]: 732

[Synthesis Example 3] Synthesis of C 13

Synthesis Example 1 and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure was performed to obtain the title compound C 13 (5.86 g, yield 80%).

Mass: [(M+H) ⁺ ]: 732

[Synthesis Example 4] Synthesis of C 14

The same as in Synthesis Example 1, except that 4-chloro-2,6-diphenylpyridine (2.65 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine By performing the procedure, the title compound C 14 (4.97 g, yield 68%) was obtained.

Mass: [(M+H) ⁺ ]: 731

[Synthesis Example 5] Synthesis of C 15

Same as Synthesis Example 1, except that 2-chloro-4,6-diphenylpyridine (2.65 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine By performing the procedure, the title compound C 15 (5.69 g, yield 78%) was obtained.

Mass: [(M+H) ⁺ ]: 731

[Synthesis Example 6] Synthesis of C 21

2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol) was carried out in the same manner as in Synthesis Example 1 to obtain the title compound C 21 (6.80 g, yield 84%).

Mass: [(M+H) ⁺ ]: 809

[Synthesis Example 7] Synthesis of C 22

2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.43 g, 10.00 mmol ) Was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 22 (7.03 g, yield 87%).

Mass: [(M+H) ⁺ ]: 809

[Synthesis Example 8] Synthesis of C 23

2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.43 g, 10.00 mmol ) Was carried out in the same manner as in Synthesis Example 1 to obtain the target compound C 23 (5.41 g, yield 67%).

Mass: [(M+H) ⁺ ]: 809

[Synthesis Example 9] Synthesis of C 41

Except for using CDT-2 (6.27 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 41 (5.94 g, yield 81%).

Mass: [(M+H) ⁺ ]: 733

[Synthesis Example 10] Synthesis of C 52

Except for using CDT-2 (6.27 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 7 was performed to obtain the title compound C 52 (5.82 g, yield 72%).

Mass: [(M+H) ⁺ ]: 809

[Synthesis Example 11] Synthesis of C71

Except for using CDT-3 (6.12 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 71 (6.38 g, yield 89%).

Mass: [(M+H) ⁺ ]: 717

[Synthesis Example 12] Synthesis of C82

Except for using CDT-3 (6.12 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 7 was performed to obtain the title compound C 82 (6.19 g, yield 78%).

Mass: [(M+H) ⁺ ]: 793

[Synthesis Example 13] Synthesis of C 101

Except for using CDT-4 (6.12 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 101 (6.09 g, yield 85%).

Mass: [(M+H) ⁺ ]: 717

[Synthesis Example 14] Synthesis of C 112

Except for using CDT-4 (6.12 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 7 was performed to obtain the title compound C 112 (5.71 g, yield 72%).

Mass: [(M+H) ⁺ ]: 793

[Synthesis Example 15] Synthesis of C121

Except for using CDT-5 (5.51 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 121 (4.86 g, yield 74%).

Mass: [(M+H) ⁺ ]: 657

[Synthesis Example 16] Synthesis of C131

Except for using CDT-5 (5.51 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 7 was performed to obtain the target compound C 131 (5.87 g, yield 80%).

Mass: [(M+H) ⁺ ]: 734

[Synthesis Example 17] Synthesis of C136

Except for using CDT-6 (5.51 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 136 (4.60 g, yield 70%).

Mass: [(M+H) ⁺ ]: 657

[Synthesis Example 18] Synthesis of C146

Except for using CDT-6 (5.51 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 7 was performed to obtain the target compound C 146 (6.02 g, yield 82%).

Mass: [(M+H) ⁺ ]: 734

[Synthesis Example 19] Synthesis of C151

Except for using CDT-7 (5.35 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 151 (4.49 g, yield 70%).

Mass: [(M+H) ⁺ ]: 641

[Synthesis Example 20] Synthesis of C161

Except for using CDT-7 (5.35 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 7 was performed to obtain the title compound C 161 (6.02 g, yield 84%).

Mass: [(M+H) ⁺ ]: 717

[Synthesis Example 21] Synthesis of C166

Except for using CDT-8 (5.35 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 166 (4.94 g, yield 77%).

Mass: [(M+H) ⁺ ]: 641

[Synthesis Example 22] Synthesis of C176

Except for using CDT-8 (5.35 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 7 was performed to obtain the title compound C 176 (5.81 g, yield 81%).

Mass: [(M+H) ⁺ ]: 717

[Synthesis Example 23] Synthesis of C126

Except for using CDT-9 (6.28 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 126 (5.28 g, yield 72%).

Mass: [(M+H) ⁺ ]: 733

[Synthesis Example 24] Synthesis of C181

Except for using ADT-1 (6.70 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound C 181 (5.88 g, yield 76%).

Mass: [(M+H) ⁺ ]: 775

[Synthesis Example 25] Synthesis of C 196

Except for using ADT-2 (6.70 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 196 (5.50 g, yield 71%).

Mass: [(M+H) ⁺ ]: 775

[Synthesis Example 26] Synthesis of C 211

Except for using ADT-3 (6.54 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound C 211 (5.24 g, yield 69%).

Mass: [(M+H) ⁺ ]: 759

[Synthesis Example 27] Synthesis of C226

Except for using ADT-4 (6.54 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound C 226 (5.54 g, yield 73%).

Mass: [(M+H) ⁺ ]: 759

[Synthesis Example 28] Synthesis of C241

Except for using ADT-5 (5.94 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 241 (5.03 g, yield 72%).

Mass: [(M+H) ⁺ ]: 699

[Synthesis Example 29] Synthesis of C 256

Except for using ADT-6 (5.94 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound C 256 (5.03 g, yield 72%).

Mass: [(M+H) ⁺ ]: 699

[Synthesis Example 30] Synthesis of C 271

Except for using ADT-7 (5.77 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 271 (5.74 g, yield 84%).

Mass: [(M+H) ⁺ ]: 683

[Synthesis Example 31] Synthesis of C 286

Except for using ADT-8 (5.77 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was carried out to obtain the title compound C 286 (6.01 g, yield 88%).

Mass: [(M+H) ⁺ ]: 683

[Synthesis Example 32] Synthesis of C246

Except for using ADT-9 (6.70 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 246 (6.20 g, yield 80%).

Mass: [(M+H) ⁺ ]: 775

[Synthesis Example 33] Synthesis of C301

Except for using PDT-1 (6.60 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C301 (5.36 g, yield 70%).

Mass: [(M+H) ⁺ ]: 765

[Synthesis Example 34] Synthesis of C346

Except for using PDT-2 (6.44 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 346 (5.46 g, yield 73%).

Mass: [(M+H) ⁺ ]: 748

[Synthesis Example 35] Synthesis of C421

Except for using PDT-3 (6.44 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 421 (5.45 g, yield 73%).

Mass: [(M+H) ⁺ ]: 748

[Synthesis Example 36] Synthesis of C466

Except for using PDT-4 (6.28 g, 10.00 mmol) instead of CDT-1, the same procedure as in Synthesis Example 1 was performed to obtain the title compound C 466 (5.79 g, yield 79%).

Mass: [(M+H) ⁺ ]: 733

[Examples 1 to 36] Fabrication of green organic EL device

Compounds C 11 to C 466 synthesized in Synthesis Examples 1 to 36 were subjected to high purity sublimation purification by a commonly known method, and then a green organic EL device was manufactured according to the following procedure.

First, the glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV The substrate was transferred to the furnace.

Each compound of m-MTDATA (60 nm)/TCTA (80 nm)/C 11 ~ C 466 + 10% Ir(ppy) ₃ (30 nm)/BCP (10 nm)/Alq ₃ ( 30 nm)/LiF (1 nm)/Al (200 nm) were stacked in order to fabricate an organic EL device.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , CBP and BCP are as follows.

[Comparative Example 1] Fabrication of green organic EL device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 11 as a light emitting host material when forming the emission layer.

[Evaluation example]

For each of the green organic EL devices prepared in Examples 1 to 36 and Comparative Example 1, the driving voltage, current efficiency and emission peak at a current density (10) mA/cm2 were measured, and the results are shown in Table 1 below. Done.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 1 C 11 6.83 517 41.1 Example 2 C 12 6.82 518 40.7 Example 3 C 13 6.49 518 38.9 Example 4 C 14 6.81 518 39.1 Example 5 C 15 6.82 518 40.7 Example 6 C 21 6.49 518 38.9 Example 7 C 22 6.81 518 39.1 Example 8 C 23 6.66 516 41.7 Example 9 C 41 6.68 518 41.7 Example 10 C 52 6.63 517 39.3 Example 11 C 71 6.61 518 38.5 Example 12 C 82 6.87 517 39.1 Example 13 C 101 6.66 517 41.1 Example 14 C 112 6.71 518 42.2 Example 15 C 121 6.82 517 42.2 Example 16 C 131 6.81 518 41.1 Example 17 C 136 6.83 518 41.7 Example 18 C 146 6.82 518 39.3 Example 19 C 151 6.82 518 39.1 Example 20 C 161 6.81 518 39.1 Example 21 C 166 6.81 518 40.7 Example 22 C 176 6.71 516 39.2 Example 23 C 126 6.68 517 39.8 Example 24 C 181 6.66 518 39.3 Example 25 C 196 6.66 518 39.7 Example 26 C 211 6.63 518 39.2 Example 27 C 226 6.62 518 39.1 Example 28 C 241 6.61 518 39.9 Example 29 C 256 6.49 518 42.2 Example 30 C 271 6.81 516 41.1 Example 31 C 286 6.81 518 41.1 Example 32 C 246 6.71 517 40.4 Example 33 C 301 6.68 518 41.7 Example 34 C 346 6.66 517 39.8 Example 35 C 421 6.73 517 40.7 Example 36 C 466 6.74 518 40.8 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compounds (C 11 to C 466) according to the present invention were used as the light emitting layer of the green organic EL device (Examples 1 to 36), the green organic EL device using the conventional CBP (Comparative Example 1 Compared with ), it can be seen that it shows better performance in terms of efficiency and driving voltage.

Claims (12)

A compound characterized in that it is selected from the group consisting of compounds represented by the following formulas 3 to 7:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 7,
Ar ₁ is a substituent represented by any one of the following A-1 to A-15,
Y ₁ is O or S;
Z ₁ is a single bond, selected from the group consisting of C(R ₁₁ )(R ₁₂ ), N(R ₁₃ ), O and S;
L ₁ is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ to C ₄₀ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
L ₂ is a single bond, or a substituted or unsubstituted C ₆ ~C ₄₀ arylene group;
R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphinyl group and C ₆ ~ C ₄₀ selected from the group consisting of arylsilyl group, but does not form a condensed ring by bonding with adjacent groups ;
R ₉ is a C ₆ ~ C ₄₀ aryl group;
R ₁₀ to R ₁₃ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ mono or diarylphosphinyl group and C ₆ ~ C ₄₀ selected from the group consisting of arylsilyl group, or combined with an adjacent group to form a condensed ring;
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of the R ₁ to R ₈ and R ₁₀ to R ₁₃ , Alkyl boron group, aryl boron group, arylphosphine group, mono or diarylphosfinyl group and arylsilyl group and the aryl group of R ₉ are each independently deuterium, halogen, cyano 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, 5 to 40 nuclear atoms heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ mono or diarylphosphine group and C ₆ ~ C ₄₀ arylsilyl group When substituted or unsubstituted with one or more selected from the group, and substituted with a plurality of substituents, they are the same as or different from each other;
m is an integer of 0 to 4, and when m is 0, it means that hydrogen is not substituted with a substituent R ₁₀ , and when m is an integer of 2 to 4, a plurality of R _10s are the same or different, respectively.

(In the above A-1 to A-15,
L3 is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ ~ C ₄₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
R ₁₄ is hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom number 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl boron groups, C ₆ to C ₄₀ aryl boron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ ~ C ₄₀ mono or is selected from diaryl phosphine blood group and an aryl silyl group consisting of a C ₆ ~ C ₄₀ of, Two or more of the plurality of R ₁₄ are not hydrogen;
Alkyl group of the R _14, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alky When substituted or unsubstituted with one or more substituents selected from the group consisting of a nil group, a C ₆ ~ C ₄₀ aryl group and a C ₃ ~ C ₄₀ cycloalkyl group, and when substituted with a plurality of substituents, they are the same or different from each other,
R ₂₁ is hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted nuclear atom number 5 to 40 heteroaryl group, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ aryl An amine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ mono or diaryl the Phosphinicosuccinic group and a substituted or unsubstituted C ₆ ~ C ₄₀ selected from the group consisting arylsilyl of Become;
n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₂₁ , and when n is an integer of 2 to 4, a plurality of R _21s are the same or different, respectively) The method of claim 1,
The L ₁ and L ₂ are each independently a single bond, a compound, characterized in that selected from the group consisting of phenylene and biphenylene. delete delete delete The method of claim 1,
The L ₃ is a compound, characterized in that selected from the group consisting of a single bond, phenylene and biphenylene. The method of claim 1,
The substituent linked by L ₁ is a compound, characterized in that dibenzofuran (dibenzo[b,d]furan) or dibenzothiophene (dibenzo[b,d]thiophene). The method of claim 1,
The substituent linked to L ₂ is any one selected from the group consisting of carbazole, phenoxazine, phenothiazine, phenazine, and acridine. compound. delete The method of claim 1,
The compound is a compound characterized in that selected from the group consisting of the following compounds:

It includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers comprises a compound selected from the group consisting of the compound according to any one of claims 1, 2, 6 to 8, and 10. EL device. The method of claim 11,
An organic electroluminescent device, wherein the organic material layer comprising a compound selected from the group consisting of the compound according to any one of claims 1, 2, 6 to 8, and 10 is an emission layer.