KR20200077824A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same. More specifically, the present invention relates to a compound having excellent thermal stability, electrochemical stability, luminescence ability, and hole/electron transport ability, and luminous efficiency; and an organic electroluminescent device having improved luminous efficiency, driving voltage, lifespan, etc., by containing the compound in one or more organic material layer.

Description

Organic light emitting compounds and organic electroluminescent devices using the same {ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more specifically, a compound having excellent thermal stability, electrochemical stability, light-emitting ability, hole/electron transport ability, and one or more organic material layers to emit light-emitting efficiency , It is related to an organic electroluminescent device having improved characteristics such as driving voltage and life.

In the organic electroluminescent device (hereinafter, referred to as'organic EL device'), when current or voltage is applied to two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected hole meets the electron, an exciton is formed, and the exciton falls to the ground state to emit light. At this time, 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, etc. according to its function.

The light emitting material of the organic EL device may be divided into blue, green, and red light emitting materials according to the light emission color. In addition, it can be divided into yellow and orange light-emitting materials necessary for realizing a better natural color. In addition, a host/dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer. The dopant material may be divided 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. Since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times that of the fluorescence, attention is focused on phosphorescent host materials as well as phosphorescent dopants.

To date, the hole injection layer and the hole transport layer. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formula are widely known, and anthracene derivatives are reported as fluorescent dopant/host materials in light emitting materials. Particularly, among the light emitting materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) _2, etc., which have great advantages in terms of efficiency improvement, are blue, green, and red dopant materials. Is being used as To date, CBP has shown excellent properties as a phosphorescent host material.

However, the existing materials have an advantage in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, which is not a satisfactory level in terms of life in the organic EL device. Therefore, development of an organic material layer material having excellent performance is required.

An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device, and can be used as a light emitting layer material or an electron transport layer material having excellent thermal stability, electrochemical stability, light emitting ability, and hole/electron transport ability.

In addition, another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage and high luminous efficiency and improves life, including the novel organic compound.

In order to achieve the above object, the present invention provides a compound represented by Formula 1:

(In the formula 1,

A ring is a C ₆ ~ C ₆₀ polycyclic aromatic ring,

X is selected from the group consisting of C(R ₂ )(R ₃ ), N(R ₄ ), O and S,

Y ₁ to Y ₃ are the same as or different from each other, and each independently N or CR ₅ , provided that at least one of Y ₁ to Y ₃ is N, and when CR ₅ is plural, a plurality of R _{5 s} are the same or different from each other Different,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently selected from the group consisting of C ₆ to C ₆₀ aryl groups and heteroaryl groups having 5 to 60 nuclear atoms,

L ₁ is a C ₆ ~C ₆₀ arylene group,

a is an integer from 0 to 4,

R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to alkynyl group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, and selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of,

The polycyclic aromatic ring of the A ring, an arylene group of L _1, an aryl group of Ar ₁ and Ar ₂ , a heteroaryl group, an alkyl group of R ₁ to R ₅ , an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group , Heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently deuterium, halogen, cyan No 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, 3 to 40 nuclear atoms heterocycloalkyl group , C ₆ ~ C ₆₀ aryl group, a nuclear number of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group , C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C of ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine Substituted or unsubstituted with one or more substituents selected from the group consisting of an oxide group and an arylamine group of C ₆ to C ₆₀ , where the plurality of substituents are the same or different from each other).

In addition, the present invention is an organic electroluminescent device comprising the above-described anode, cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the organic material layers of the one or more layers is represented by Formula 1 It provides an organic electroluminescent device comprising a compound.

Since the compound of the present invention has excellent thermal stability, electrochemical stability, luminescence ability, hole transport ability, and electron transport ability, it can be usefully applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer has significantly improved aspects such as luminescence performance, driving voltage, life, efficiency, and can be effectively applied to a full color display panel.

1 is a cross-sectional view schematically showing an organic electroluminescent device according to an example of the present invention.
2 is a cross-sectional view schematically showing an organic electroluminescent device according to another example of the present invention.

Hereinafter, the present invention will be described in detail.

<New compound>

The present invention provides a novel organic compound that can be used as a high-efficiency light-emitting layer material, specifically a host or a dopant, having excellent electrochemical stability, thermal stability, hole/electron transport ability, and luminescence ability.

Specifically, the compound of Formula 1 according to the present invention includes a core structure formed by linking an N-containing 6-membered heterocycle to the N position of an N-containing condensed heteroaromatic ring moiety through a linker.

In the compound of Formula 1, the N-containing condensed heteroaromatic ring moiety is a side such as a benzene ring, naphthalene ring, anthracene ring, pyrene ring, etc., on one side of a phenoxazine moiety having P-type properties. It is obtained by condensing a monocyclic or polycyclic aromatic ring, and has a rigid structure. Therefore, the compound of the present invention has a high glass transition temperature, and thus not only has excellent thermal stability, but also excellent electrochemical stability.

In addition, the N-containing condensed heteroaromatic ring moiety is an electron donating group (EDG) having a large electron donor, and the N-containing 6-membered heterocyclic ring is a pyridine ring, a pyrimidine ring, a triazine ring, and electron absorbing property. This is a large electron withdrawing group (EWG). Therefore, the compound of the present invention has not only a high binding force between holes and electrons, but also excellent hole/electron transportability and high triplet energy because the entire molecule has bipolar properties. Due to this, the compound of the present invention is excellent in luminescence ability and hole/electron transport ability, and thus can exhibit low voltage, high efficiency, and long life characteristics when applied as a light emitting layer material of OLED, especially phosphorescent, fluorescent host, or dopant. In particular, since the compound of the present invention has a high triplet energy and a small singlet and triplet energy difference (ΔEST), it is possible to prevent the exciton generated in the light emitting layer from diffusing into the electron transport layer or the hole transport layer adjacent to the light emitting layer. In the end, the number of excitons contributing to the light emission in the light emitting layer can be substantially increased to improve the luminous efficiency and absolute quantum efficiency of the device, and the durability and stability of the device can be improved to significantly increase the life characteristics of the device have.

In addition, the compound of the present invention is not only excellent in electrochemical stability due to the strong bond between the N-containing condensed heteroaromatic ring moiety and the N-containing 6-membered heterocyclic ring, but also minimizes the interaction between them, resulting in the structural stability of the molecule. Increased, physical and thermal stability can be significantly increased.

In addition, the compound of the present invention can control hole/electron transport capacity by specifying a monocyclic or polycyclic aromatic ring condensed on one side of a phenoxazine moiety, and maintains the molecule while maintaining the HOMO level of the molecule. You can tune. In addition, the compound of the present invention can control the energy level, the steric effect, and the thin film properties of the compound by controlling the type and position of the substituent introduced into the core structure.

As described above, the compound represented by Formula 1 according to the present invention has excellent thermal stability, electrochemical stability, hole/electron transportability, and luminescence ability. In addition, the compound of the present invention can prevent the movement (diffusion) of the exciton generated in the light emitting layer to the adjacent layer, thereby increasing the number of excitons in the light emitting layer. Accordingly, the compound represented by Formula 1 of the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material, specifically, a green, red, or blue phosphorescent host or dopant, or a green, red, or blue phosphorescent host or dopant. Can be used. The performance of the organic electroluminescent device including the compound of the present invention can be greatly improved, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can be maximized.

In the compound represented by Formula 1, the A ring is a C ₆ ~ C ₆₀ polycyclic aromatic ring, preferably a C ₆ ~ C ₄₀ polycyclic aromatic ring, and more preferably a C ₆ ~ C ₄₀ bicyclic ~ It may be an 8-ring aromatic ring. At this time, when there are a plurality of A rings, the plurality of A rings are the same or different from each other, and each ring in the polycyclic aromatic ring may be the same or different from each other.

Specifically, examples of the A ring include a naphthalene ring, anthracene ring, tetracene ring, pyrene ring, phenanthrene ring, phenalene ring, benzoanthracene ring, benzo It may be a pyrene (benzopyrene) ring, a triphenylene ring, a chrysene ring, a pentaphene ring, a pentacene ring, and a condensed ring between the two rings. Does not work.

According to an example, the compound represented by Formula 1 may be embodied as a compound represented by Formula 2 below, but is not limited thereto.

In Chemical Formula 2,

X, Y ₁ to Y ₃ , L ₁ , Ar ₁ , Ar ₂ , a, and R ₁ are each as defined in Chemical Formula 1,

B ring is a C ₆ ~ C ₄₀ monocyclic aromatic ring or C ₆ ~ C ₄₀ polycyclic aromatic ring, preferably a benzene ring, naphthalene ring, anthracene ring, tetracene (tetracene) ring, pyrene (pyrene) ring, Phenanthrene ring, phenalene ring, benzoanthracene ring, benzopyrene ring, triphenylene ring, chrysene ring, pentaphene ring , A pentacene ring, and a condensed ring between the two rings, and the like.

Specifically, the compound represented by Formula 1 may be embodied as a compound represented by any one of the following Formulas 3 to 7, but is not limited thereto.

In the above formula 3 to 7,

X, Y ₁ to Y ₃ , L ₁ , Ar ₁ , Ar ₂ , a, and R ₁ are as defined in Formula 1, respectively.

In addition, in the compound represented by Formula 1, a is an integer of 0 to 4.

Here, when a is 0, it means that hydrogen is not substituted with the substituent R ₁ , and when a is an integer from 1 to 4, one or more R ₁ are the same or different from each other, and each independently deuterium, halogen group, cyan No group, nitro group, amino 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, 3 to 40 heteroatoms Cycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl Silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C and selected from the ₆₀ group consisting of aryl amines, preferably C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ aryl of C ₆₀ It may be selected from the group consisting of amine groups, and more preferably may be selected from the group consisting of C ₆ ~ C ₆₀ aryl groups and C ₆ ~ C ₆₀ arylamine groups.

According to an example, R ₁ may be selected from the group consisting of hydrogen and the following substituents S1 to S24.

In the substituents S1 to S24,

R ₆ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, preferably selected from the group consisting of hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group may, C ₂ ~ C ₄₀ may be selected from an alkenyl group, and alkynyl group the group consisting of C ₂ ~ C _40.

In addition, in the compound represented by Chemical Formula 1, X is selected from the group consisting of C(R ₂ )(R ₃ ), N(R ₄ ), O and S, and preferably X may be O or S.

Moreover, R ₂ to R ₄ are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C Alkynyl group of ₂ to C ₄₀ , cycloalkyl group of C ₃ to C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ arylboronic group of C _60, C ₆ ~ C ₆₀ aryl phosphine group, is selected from C ₆ ~ C ₆₀ aryl phosphine oxide group, and the group consisting of C ₆ - C ₆₀ aryl amine of the.

Preferably, R ₂ to R ₄ are the same or different from each other, and each independently hydrogen, hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alke Nyl group, C ₂ ~ C ₄₀ alkynyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, and C ₆ ~ C ₆₀ aryl It may be selected from the group consisting of amine groups.

In addition, in the compound represented by Formula 1, Y ₁ to Y ₃ are the same as or different from each other, and each independently N or CR ₅ , provided that at least one of Y ₁ to Y ₃ is N. At this time, when CR ₅ is plural, a plurality of R ₅ are the same or different from each other. Preferably, Y ₁ to Y ₃ may all be N. Thus, Y ₁ to Y ₃ are both N a N- containing 6-membered heterocyclic ring (i.e., a triazine ring) is Y ₁ to Y ₃ in one to two dogs of N- N-containing 6-membered heterocyclic ring (i.e., pyridine ring or Compared to the pyrimidine ring), since the EWG property is stronger, the bipolar property of the compound may be further increased.

모이어티는 하기 구조식 Z1 내지 Z3 중 어느 하나로 표시되는 모이어티일 수 있다.According to Y ₁ ~ Y ₃ , the formula (1)

The moiety may be a moiety represented by any one of the following structural formulas Z1 to Z3.

In the above structural formula Z1 to Z3,

Ar ₁ and Ar ₂ are as defined in Formula 1, respectively.

In addition, R ₅ is the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, is selected from C ₆ ~ C ₆₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of.

Preferably, R ₅ is hydrogen, hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, nucleus It may be selected from the group consisting of a heterocycloalkyl group having 3 to 40 atoms, an aryl group of C ₆ to C ₆₀ , a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group of C ₆ to C ₆₀ .

In addition, in the compound represented by Chemical Formula 1, Ar ₁ and Ar ₂ are the same or different from each other, and each independently selected from the group consisting of C ₆ to C ₆₀ aryl groups and heteroaryl groups having 5 to 60 nuclear atoms. , Preferably it may be selected from the group consisting of C ₆ ~ C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms.

Specifically, Ar ₁ and Ar ₂ may be the same or different from each other, and each independently a substituent selected from the group consisting of the substituents S1 to S23.

In addition, in the compound represented by Chemical Formula 1, L ₁ is a divalent linker group, an arylene group of C ₆ to C ₆₀ , and preferably an arylene group of C ₆ to C ₄₀ . Specifically, examples of L ₁ include a phenylene group, a biphenylene group, a terphenylene group, and a divalent naphthalene group, but are not limited thereto.

According to an example, the compound represented by Formula 1 may be embodied as a compound represented by Formula 8 or 9 below, but is not limited thereto.

In Chemical Formulas 8 and 9,

B ring is a C ₆ ~ C ₄₀ monocyclic aromatic ring or C ₆ ~ C ₄₀ polycyclic aromatic ring, preferably benzene ring, naphthalene ring, anthracene ring, tetracene (tetracene) ring, pyrene (pyrene) ring, Phanthanthrene ring, phenalene ring, benzoanthracene ring, benzopyrene ring, triphenylene ring, chrysene ring, pentaphene ring , May be selected from the group consisting of a pentacene ring, and a condensed ring between the two rings,

X, Y ₁ to Y ₃ , Ar ₁ , Ar ₂ , a, and R ₁ are each as defined in Chemical Formula 1,

b is an integer from 0 to 4,

c is an integer from 0 to 6,

R ₆ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, preferably selected from the group consisting of hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group may, C ₂ ~ C ₄₀ may be selected from an alkenyl group, and alkynyl group the group consisting of C ₂ ~ C _40.

Specifically, in the compound represented by the formula (8), the hetero ring containing the B ring and the hetero ring containing Y ₁ may be bonded to each other in a meta position with respect to the benzene ring containing R ₆ . In this case, the compound represented by Formula 1 may be embodied as a compound represented by Formula 10 below. Here, the compound represented by the following formula (10) due to the linear (linear) structure, the bipolar (bipolar) properties are increased, because the energy absorption and emission characteristics are excellent, the light emitting layer material of the organic electroluminescent device, specifically as a dopant When used, it is possible to increase the current efficiency while lowering the driving voltage of the organic EL device.

In the compound represented by Chemical Formula 8, the hetero ring containing B ring and the hetero ring containing Y ₁ may be bonded to each other in a para position with respect to the benzene ring containing R ₆ . In this case, the compound represented by Formula 1 may be embodied as a compound represented by Formula 11 below. Here, the compound represented by the following formula (11) due to the bending structure, because it is easy to receive and transmit electrons and holes organically and has a wide band gap including the energy level of the dopant, the light emitting layer material of the organic electroluminescent device, Specifically, when used as a host, it is possible to increase the current efficiency while lowering the driving voltage of the organic EL device.

In addition, in the compound represented by the formula (9), the hetero ring containing B ring and the hetero ring containing Y ₁ may be bonded to positions 1-4 of naphthalene with respect to the naphthalene ring containing R ₆ . In this case, the compound represented by Formula 1 may be embodied as a compound represented by Formula 12 below. Here, the compound represented by the following formula (12) is a linear (linear) structure, the bipolar property is increased, because the energy absorption and luminescence properties are excellent, when used as a light emitting layer material, specifically dopant of the organic electroluminescent device, The current efficiency can be increased while lowering the driving voltage of the organic EL device.

In Chemical Formulas 10 to 12,

B ring is a C ₆ ~ C ₄₀ monocyclic aromatic ring or C ₆ ~ C ₄₀ polycyclic aromatic ring, preferably benzene ring, naphthalene ring, anthracene ring, tetracene (tetracene) ring, pyrene (pyrene) ring, Phanthanthrene ring, phenalene ring, benzoanthracene ring, benzopyrene ring, triphenylene ring, chrysene ring, pentaphene ring , May be selected from the group consisting of a pentacene ring, and a condensed ring between the two rings,

X, Y ₁ to Y ₃ , Ar ₁ , Ar ₂ , a, and R ₁ are each as defined in Chemical Formula 1,

b is an integer from 0 to 4,

c is an integer from 0 to 6,

R ₆ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, preferably selected from the group consisting of hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group may, C ₂ ~ C ₄₀ may be selected from an alkenyl group, and alkynyl group the group consisting of C ₂ ~ C _40.

In addition, in the formula (1), the polycyclic aromatic ring of the A ring, an arylene group of L _1, an aryl group of Ar ₁ and Ar ₂ , a heteroaryl group, an alkyl group of R ₁ to R ₅ , an alkenyl group, an alkynyl group, a cycloalkyl group , Heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group, respectively 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 ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ Substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups of ~C ₆₀ and arylamine groups of C ₆ ~C ₆₀ , preferably deuterium, halogen, cyano group, nitro group, C ₁ ~C It may be unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group of ₂₀ , an aryl group of C ₆ ~C ₃₀ , a heteroaryl group having 5 to 30 nuclear atoms. In this case, when the substituents are plural, they are the same or different from each other.

The compound represented by Formula 1 may be embodied as a compound represented by any one of the following Formulas 13 to 21, but is not limited thereto.

In Chemical Formulas 13 to 21,

X, Y ₁ to Y ₃ , Ar ₁ , Ar ₂ , R ₁ are the same as defined in Formula 1,

R ₆ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ arylamine group is selected from the group consisting of,

d is 0 or 1,

Here, when d is 0, it means that hydrogen is not substituted with the substituent R ₇ , and when d is 1, R ₇ is a C ₁ ~C ₄₀ alkylene group, C ₂ ~ C ₄₀ alkenylene group, C ₂ Alkynylene group of ~C ₄₀ , cycloalkylene group of C ₃ ~C ₄₀ , heterocycloalkylene group of 3 to 40 nuclear atoms, arylene group of C ₆ ~C ₆₀ , and heteroarylene of 5 to 60 nuclear atoms It is selected from the group consisting of groups, specifically, may be selected from the group consisting of a phenylene group, biphenylene group, divalent dibenzothiophene group, divalent dibenzofuran, divalent carbazole group, and divalent fluorene group,

e is 0 or 1,

Here, when e is 0, it means that hydrogen of R ₇ is not substituted with a substituent -N(R ₈ ) ₂ , and when d is 1, a plurality of R ₈ are the same or different from each other, and each independently C ₆ It is selected from the group consisting of an aryl group of ~C _{60 and} a heteroarylene group having 5 to 60 nuclear atoms, preferably selected from the group consisting of an aryl group of C ₆ to C _{40 and} a heteroarylene group of 5 to 60 nuclear atoms. Can be specifically selected from the group consisting of a phenyl group, a biphenyl group, a monovalent dibenzothiophene group, a monovalent dibenzofuran, a monovalent carbazole group, and a monovalent fluorene group,

The alkylene group, alkenylene group, alkynylene group, cycloalkylene group, heterocycloalkylene group, arylene group and heteroarylene group of R ₇ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ of Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nucleus Heteroaryl group having 5 to 60 atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C group of ₁ to alkylboronic of C _40, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine Substituted or unsubstituted with one or more substituents selected from the group consisting of groups, preferably deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₃₀ aryl group, 5 to ₆ nuclear atoms It may be unsubstituted or substituted with one or more substituents selected from the group consisting of 30 heteroaryl groups. In this case, when the substituents are plural, they are the same or different from each other.

The compound represented by the formula (1) according to the present invention described above may be further embodied as the following exemplary compounds, for example, compounds A-1-1 to D-2-30, but is not limited thereto. Here, compounds A-1-1 to 28, A-3-1 to A-3-28, A-4-1 to A-4-28, A-5-1 to A-5-28, B-1 -1~B-1-28, B-3-1~B-3-28, B-4-1~B-4-28, C-1-1~C-1-28, C-3-1 ~C-3-28, C-4-1~C-4-28, D-1-1~D-1-30, D-2-1~D-2-30 are compounds of linear structure Furnace, when used as a dopant in the light emitting layer material of the organic electroluminescent device, due to the excellent luminous efficiency and bipolar characteristics of the compound itself, the driving voltage of the organic electroluminescent device is lowered, the current efficiency can be improved. On the other hand, compounds A-2-1 to A-2-28, A-6-1 to A-6-28, B-2-1 to B-2-28, C-2-1 to C-2-28 As a compound of a silver bent structure, when used as a host among the light emitting layer materials of the organic electroluminescent device, it has excellent hole/electron transporting ability, and can improve the current efficiency while lowering the driving voltage of the organic electroluminescent device.

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

In the present invention, "alkenyl (alkenyl)" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples of the vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.

In the present invention, "alkynyl (alkynyl)" means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples of this include ethynyl, 2-propynyl, and the like, but are not limited thereto.

"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, adamantine, and the like.

In the present invention, "heterocycloalkyl" refers to 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 a hetero atom such as Se. Examples of such heterocycloalkyl include morpholine, piperazine, and the like, but are not limited thereto.

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, two or more rings may be simply attached to each other (pendant) or a condensed form. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is 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 condensed form with an aryl group may also be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.

"Alkylsilyl" in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl. Moreover, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as di- and tri-arylsilyl as well as mono-.

In the present invention, "alkyl boron group" means a boron group substituted with alkyl having 1 to 40 carbon atoms, and "aryl boron group" means a boron group substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "alkylphosphinyl group" means a phosphine group substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. In addition, in the present invention, "arylphosphinyl group" means a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.

In the present invention, "arylamine" means an amine substituted with aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.

<Organic electroluminescent device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (hereinafter referred to as'organic EL device') comprising the compound represented by Chemical Formula 1 described above.

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, wherein at least one of the organic material layers of the one or more layers is It includes a compound represented by the formula (1). At this time, the compound may be used alone, or may be used by mixing two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one organic material layer includes a compound represented by Formula 1 above. Preferably, the organic material layer including the compound of Formula 1 may be a light emitting layer.

According to an example, the organic material layer of the one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, the light emitting layer includes a host and a dopant, and the dopant is a compound represented by Formula 1 , Preferably it may be a compound represented by the formula (10) or (12).

According to another example, the organic material layer of the one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, the light emitting layer includes a host and a dopant, and the host is represented by Formula 1 It includes a compound, it may be preferably a compound represented by the formula (11). In this case, the light emitting layer of the present invention may include a compound known in the art as a second host other than the compound of Formula 1 above.

In the present invention, the content of the host may be about 70 to 99.9% by weight based on the total amount of the light emitting layer, and the content of the dopant may be about 0.1 to 30% by weight based on the total amount of the light emitting layer.

The compound represented by Chemical Formula 1 may be included in the organic electroluminescent device as a light emitting layer material, preferably green, blue and red phosphorescence, a fluorescent host, or a dopant. In this case, since the bonding force between holes and electrons in the light emitting layer is increased, efficiency (light emission efficiency and power efficiency), life, luminance, driving voltage, and thermal stability of the organic electroluminescent device may be improved.

The structure of the organic electroluminescent device of the present invention is not particularly limited, for example, on the substrate, the anode 100, one or more organic material layers 300 and the cathode 200 may be sequentially stacked (FIGS. 1 and 2). Reference). In addition, an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic material layer.

According to an example, the organic electroluminescent device, as shown in Figure 1, on the substrate, the anode 100, the hole injection layer 310, the hole transport layer 320, the light emitting layer 330, the electron transport layer 340 and The cathode 200 may have a structure sequentially stacked. Optionally, as illustrated in FIG. 2, an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200. In addition, a hole blocking layer (not shown) may be positioned between the emission layer 330 and the electron transport layer 340. In the organic electroluminescent device of the present invention, at least one of the organic material layer 300 (eg, a light emitting layer 330, a hole blocking layer (not shown) or an electron transport layer 340) includes a compound represented by Chemical Formula 1 Except for that, it can be produced by forming an organic material layer and an electrode using materials and methods known in the art.

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

The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

Further, examples of the positive electrode 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); A combination of metal and oxide 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, but is not limited thereto.

Further, examples of the negative electrode 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 LiO ₂ /Al, but is not limited thereto.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are only to illustrate the present invention, the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Compound S-2

<Step 1> Synthesis of Compound S-1

At room temperature, naphthalen-1-ol (10 g, 69 mmol) and 1-bromo-2-nitrobenzene (13.9 g, 69 mmol) were placed in a 2-neck flask, KOH (5.4 g, 96 mmol) was added thereto, and DMSO ( 150 mL), followed by heating and stirring for 8 hours. After completion of the reaction, the heated and stirred solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:3) to obtain an oil-type yellow compound S-1 (12.8g, yield 70%). .

¹ H-NMR: δ 6.65 (d, 1H), 7.18 (m, 2H), 7.32 (t, 1H), 7.50 (t, 1H), 7.68 (t, 1H), 7.77 (t, 1H), 8.01 ( t, 1H), 8.23 (m, 3H)

[LCMS]: 265

<Step 2> Synthesis of Compound S-2

Compound S-1 (10 g, 38 mmol) obtained in step 1 at room temperature was dissolved in Dichlorobenzene (100 ml), placed in a 2-neck flask, and PPy3 (21 g, 76 mmol) was added thereto, followed by 24 hours at 120°C. Stir for a while. The reactant was extracted with methylene chloride (MC), filtered through silica, the solvent was removed, and washed with MeOH to obtain a white compound S-2 (4.4 g, yield 54%).

¹ H-NMR: δ 4.08 (s, 1H), 6.42 (d, 1H), 6.58 (m, 4H), 7.31 (t, 1H), 7.44 (d, 1H), 7.65 (t, 1H), 8.01 ( d, 1H), 8.15 (d, 1H),

[LCMS]: 233

[Preparation Example 2] Synthesis of Compound S-4

<Step 1> Synthesis of Compound S-3

Instead of naphthalen-1-ol (10 g, 69 mmol) used in <Step 1> of Preparation Example 1, phenanthren-9-ol (10 g, 51 mmol) was used, and 1-bromo-2-nitrobenzene (13.9 g, 69 mmol) ) Instead of 1-bromo-2-nitrobenzene (10.4g, 51mmol), except that by performing the same process as <Step 1> of [Preparation Example 1], the target compound S-3 (10.4g, yield 65% ).

¹ H-NMR: δ 7.18 (d, 1H), 7.40 (s, 1H), 7.88 (m, 5H), 8.12 (m, 3H), 8.30 (d, 1H), 8.90 (d, 2H)

[LCMS]: 315

<Step 2> Synthesis of Compound S-4

[Preparation Example 1] Except that Compound S-3 (10 g, 32 mmol) obtained in <Step 1> was used instead of Compound S-1 (10 g, 38 mmol) used in <Step 1> of Preparation Example 1 ] Was carried out in the same manner as in <Step 2> to obtain the target compound S-4 (3.6 g, yield 40%).

¹ H-NMR: δ 4.07 (s, 1H), 6.42 (d, 1H), 6.66 (m, 3H), 7.82 (m, 4H), 8.17 (d, 2H), 8.95 (d, 2H),

[LCMS]: 283

[Preparation Example 3] Synthesis of Compound S-6

<Step 1> Synthesis of Compound S-5

Instead of naphthalen-1-ol (10 g, 69 mmol) used in <Step 1> of Preparation Example 1, phenanthren-1-ol (10 g, 51 mmol) was used, and 1-bromo-2-nitrobenzene (13.9 g, 69 mmol) ) Instead of 1-bromo-2-nitrobenzene (10.4g, 51mmol), except that by performing the same process as in <Step 1> of [Preparation Example 1], the target compound S-5 (11.8g, yield 74% ).

¹ H-NMR: δ 7.26 (d, 1H), 7.48 (d, 1H), 7.78 (m, 6H), 8.04 (t, 1H), 8.15 (d, 1H), 8.31 (d, 1H), 8.68 ( d, 1H), 8.92 (d, 1H)

[LCMS]: 315

<Step 2> Synthesis of Compound S-6

[Preparation Example 1] Except that Compound S-5 (15 g, 47 mmol) obtained in <Step 1> was used instead of Compound S-1 (10 g, 38 mmol) used in <Step 2> of Preparation Example 1 ] Was performed in the same manner as in <Step 2> to obtain the target compound S-6 (6.8 g, yield 51%).

¹ H-NMR: δ 4.11 (s, 1H), 6.59 (d, 1H), 6.73 (m, 3H), 7.10 (d, 1H), 7.85 (m, 4H), 8.14 (d, 1H), 8.44 ( d, 1H), 8.96 (d, 1H)

[LCMS]: 283

[Preparation Example 4] Synthesis of Compound S-9

<Step 1> Synthesis of Compound S-7

Instead of naphthalen-1-ol (10 g, 69 mmol) used in <Step 1> of Preparation Example 1, phenanthren-1-ol (10 g, 69 mmol) was used, and 1-bromo-2-nitrobenzene (13.9 g, 69 mmol) ) Instead of 2-bromo-4-chloro-1-nitrobenzene (16.3g, 51mmol), the same procedure as in <Step 1> of [Preparation Example 1] to perform the target compound S-6 (15.8g , Yield 77%).

¹ H-NMR: δ 6.69 (d, 1H), 7.15 (m, 2H), 7.33 (d, 1H), 7.50 (t, 1H), 7.65 (m, 2H), 8.17 (s, 1H), 8.22 ( d, 2H)

[LCMS]: 299

<Step 2> Synthesis of Compound S-8

[Preparation Example 1] Except that Compound S-7 (8 g, 27 mmol) obtained in <Step 1> was used instead of Compound S-1 (10 g, 38 mmol) used in <Step 2> of Preparation Example 1 ] Was carried out in the same manner as in <Step 2> to obtain the target compound S-6 (4.1 g, yield 57%).

¹ H-NMR: δ 4.01(s, 1H), 6.44(d, 1H), 6.60(m, 3H), 7.30(t, 1H), 7.44(d, 1H), 7.63(t, 1H), 8.00 ( d, 1H), 8.12 (d, 1H)

[LCMS]: 267

<Step 3> Synthesis of Compound S-9

After adding the compound S-8 (10 g, 37 mmol) and diphenylamine (7.5 g, 44 mmol) obtained in <Step 2> to a 2-neck flask at room temperature, Pd ₂ (dba) ₃ (1.35 g, 1.5) mmol) and NaOt-Bu (8.2 g, 74 mmol) were added, and Toluene (200 mL) was added. Then, P(t-bu) ₃ (0.06 g, 3 mmol) was added to the flask and refluxed. After completion of the reaction, the solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:4) to obtain a light yellow powder S-9 (4.7 g, yield 32%).

¹ H-NMR: δ 7.27 (t, 1H), 7.43 (t, 2H), 7.70 to 7.75 (m, 4H), 8.02 (s, 2H), 8.85 (s, 2H),

[LCMS]: 400

[Preparation Example 5] Synthesis of Compound S-10

Compound S-8 (10 g, 37 mmol), 4-(diphenylamino)phenylboronic acid (12.8 g, 44 mmol) obtained in <Step 2> of Preparation Example 4 at room temperature was placed in a 2-neck flask, and then Pd( PPh ₃ ) ₄ (1.7 g, 1.5 mmol) and NaOH (2.9 g, 74 mmol) were added. Then, anhydrous toluene (200 ml) was added to the flask, followed by stirring at 110° C. for 8 hours. After completion of the reaction, the solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:3) to obtain a light yellow powder S-10 (15.5 g, yield 88%).

¹ H-NMR: δ 4.04 (s, 1H), 6.48 (m, 6H), 6.64 (m, 2H), 6.75 (d, 1H), 7.01 (m, 7H), 7.26 (t, 1H), 7.46 ( m, 3H), 7.63 (t, 1H), 8.00 (d, 1H), 8.13 (d, 1H),

[LCMS]: 476

[Preparation Example 6] Synthesis of Compound S-11

The same procedure as in [Preparation Example 5], except that 3-(diphenylamino)phenylboronic acid (12.8g, 44 mmol) was used instead of 4-(diphenylamino)phenylboronic acid (12.8g, 44 mmol) used in Preparation Example 5. This was carried out to obtain the target compound S-11 (13.9 g, yield 79%).

¹ H-NMR: δ 4.01 (s, 1H), 6.44 (m, 5H), 6.68 (m, 4H), 6.85 (d, 1H), 7.01 (m, 8H), 7.27 (t, 1H), 7.41 ( d, 1H), 7.60 (t, 1H), 7.98 (d, 1H), 8.11 (d, 1H)

[LCMS]: 476

[Preparation Example 7] Synthesis of Compound S-12

[Preparation Example] Except that 9-phenyl-9H-carbazol-3-ylboronic acid (12.6g, 44 mmol) was used instead of 4-(diphenylamino)phenylboronic acid (12.8g, 44 mmol) used in Preparation Example 5 The same procedure as in [5] was carried out to obtain the target compound S-12 (16.5 g, yield 94%).

¹ H-NMR: δ 4.00 (s, 1H), 6.64 (m, 2H), 6.74 (d, 1H), 7.31 (m, 7H), 7.53 (m, 6H), 7.77 (s, 1H), 7.99 ( d, 1H), 8.12 (d, 1H) 8.58 (d, 1H)

[LCMS]: 474

[Preparation Example 8] Synthesis of Compound S-13

[Preparation Example] Except that dibenzo[b,d]thiophen-2-ylboronic acid (10.1g, 44 mmol) was used instead of 4-(diphenylamino)phenylboronic acid (12.8g, 44 mmol) used in Preparation Example 5. The same procedure as in [5] was carried out to obtain the target compound S-13 (13.8 g, yield 90%).

¹ H-NMR: δ 4.01(s, 1H), 6.60(m, 2H), 6.73(d, 1H), 7.08(d, 1H), 7.25(t, 1H), 7.49(m, 4H), 7.87( d, 2H), 8.00 (m, 3H), 8.10 (d, 1H) 8.45 (d, 1H)

[LCMS]: 415

[Preparation Example 9] Synthesis of Compound S-14

[Preparation Example] Except that dibenzo[b,d]furan-2-ylboronic acid (9.4g, 44 mmol) was used instead of 4-(diphenylamino)phenylboronic acid (12.8g, 44 mmol) used in Preparation Example 5. The same procedure as in [5] was carried out to obtain the target compound S-14 (12.7 g, yield 86%).

¹ H-NMR: δ 4.00 (s, 1H), 6.65 (m, 2H), 6.76 (d, 1H), 7.10 (d, 1H), 7.39 (m, 7H), 7.56 (m, 2H), 7.98 ( m, 2H) 8.12 (d, 1H)

[LCMS]: 399

[Preparation Example 10] Synthesis of Compound S-15

[Preparation Example] Except that dibenzo[b,d]furan-3-ylboronic acid (9.4g, 44 mmol) was used instead of 4-(diphenylamino)phenylboronic acid (12.8g, 44 mmol) used in Preparation Example 5. The same procedure as in [5] was carried out to obtain the target compound S-15 (11.8 g, yield 80%).

¹ H-NMR: δ 4.00 (s, 1H), 6.61 (m, 2H), 6.73 (d, 1H), 7.09 (d, 1H), 7.41 (m, 5H), 7.60 (m, 4H), 7.99 ( m, 2H) 8.11 (d, 1H)

[LCMS]: 399

[Preparation Example 11] Synthesis of Compound S-16

[Preparation Example] Except that dibenzo[b,d]furan-4-ylboronic acid (9.4g, 44 mmol) was used instead of 4-(diphenylamino)phenylboronic acid (12.8g, 44 mmol) used in Preparation Example 5. The same procedure as in [5] was carried out to obtain the target compound S-16 (12.1 g, yield 82%).

¹ H-NMR: δ 4.01(s, 1H), 6.63(m, 2H), 6.73(d, 1H), 7.09(d, 1H), 7.26(m, 5H), 7.59 (m, 2H), 7.94( m, 4H) 8.14 (d, 1H)

[LCMS]: 399

[Preparation Example 12] Synthesis of Compound S-18

<Step 1>-Synthesis of Compound S-17

At room temperature, naphthalene-1-thiol (10 g, 63 mmol), 1-bromo-2-nitrobenzene (12.6 g, 51 mmol), KOH (7 g, 126 mmol), CuI (2.3, 12 mmol) was added to Toluene (200 mL) Then, the mixture was heated and stirred for 24 hours. After completion of the reaction, the solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:3) to obtain an oil-type yellow compound S-17 (5.3 g, yield 32%).

¹ H-NMR: δ 7.13 (t, 1H), 7.46 (m, 6H), 7.53 (m, 2H), 7.68 (d, 1H), 8.18 (d, 1H)

[LCMS]: 281

<Step 2>-Synthesis of Compound S-18

Compound S-17 (10 g, 36 mmol) obtained in <Step 1> at room temperature was dissolved in Dichlorobenzene (100 ml), placed in a 2-neck flask, and P(OEt) 3 (11.9 g, 72 mmol) was added thereto. It was added and stirred at 120° C. for 24 hours. The reaction was extracted with MC, filtered through silica, the solvent was removed, and then washed with MeOH to obtain a white compound S-18 (3.95 g, yield 44%).

¹ H-NMR: δ 4.2 (s, 1H), 6.89 (m, 2H), 6.96 (m, 4H), 7.33 (t, 1H), 7.68 (m, 3H)

[LCMS]: 249

[Preparation Example 13] Synthesis of Compound S-19

2-chloro-4,6-diphenyl-1,3,5-triazine (50g, 187 mmol), (4-chloronaphthalen-1-yl)boronic acid (38.5g, 187 mmol) at room temperature in a 2-neck flask Put, Pd(PPh ₃ ) ₄ (8.6g, 7.5mmol) and K ₂ CO ₃ (51.6g, 374 mmol) were added thereto. Then, anhydrous Toluene (500 mL) was added to the flask, followed by stirring at 110° C. for 8 hours. After completion of the reaction, the solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:3) to obtain a white powder S-19 (68.3 g, yield 93%).

¹ H-NMR: δ 7.50 (m, 10H), 8.22 (d, 1H), 8.40 (m, 4H), 8.63 (d, 1H)

[LCMS]: 393

[Preparation Example 14] Synthesis of Compound S-20

2-chloro-4-(dibenzo[b,d]furan-1-yl)- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (50g, 187 mmol) used in Preparation Example 13. Except for using 6-phenyl-1,3,5-triazine (10g, 28 mmol), the same procedure as in [Preparation Example 13] was carried out to obtain the target compound S-20 (11.5g, yield 85%). .

¹ H-NMR: δ 7.43 (m, 13H), 7.98 (d, 1H), 8.21 (d, 1H), 8.37 (m, 2H), 8.62 (d, 1H)

[LCMS]: 483

[Preparation Example 15] Synthesis of Compound S-21

2-chloro-4-(dibenzo[b,d]furan-3-yl)- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (50g, 187 mmol) used in Preparation Example 13. Except for using 6-phenyl-1,3,5-triazine (10g, 28 mmol), the same procedure as in [Preparation Example 13] was performed to obtain the target compound S-21 (12.2g, yield 90%). .

¹ H-NMR: δ 7.48 (m, 12H), 7.70 (s, 1H), 8.22 (d, 1H), 8.36 (m, 2H), 8.64 (d, 1H)

[LCMS]: 483

[Preparation Example 16] Synthesis of Compound S-22

2-(biphenyl-4-yl)-4-chloro-6-phenyl-1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (50g, 187 mmol) used in Preparation Example 13. 4-chloro-2,6-dimethylphenylboronic acid (5.4 g, 29 mmol) instead of (4-chloronaphthalen-1-yl)boronic acid (38.5 g, 187 mmol) using 3,5-triazine (10 g, 29 mmol) ) Was carried out, and the same procedure as in [Preparation Example 13] was performed to obtain the target compound S-22 (11.1 g, yield 86%).

¹ H-NMR: δ 6.98 (s, 2H), 7.25 (d, 2H), 7.54 (m, 8H), 7.77 (m, 2H), 8.35 (m, 2H)

[LCMS]: 447

[Synthesis Example 1] Synthesis of Compound A-1-1

Compound S-2 (8.0 g, 34 mmol) and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 37 mmol) obtained in Preparation Example 1 at room temperature were 2- After putting in the neck flask, while maintaining nitrogen conditions, Pd ₂ (dba) ₃ (1.5 g, 1.7 mmol), NaOt-Bu (7.6 g, 68 mmol) and (t-Bu) ₃ P solution (50 wt% in) toluene) (0.7 mL, 3.4 mmol) was added, and then Toluene (200 ml) was added thereto and heated to reflux at 110°C. After completion of the reaction, the organic layer was extracted with THF, and then filtered through silica and purified by column chromatography (MC:Hexane=1:2) to remove the solvent. Thereafter, the organic layer was washed with acetone and ethanol, and recrystallized with toluene to obtain the target compound A-1-1 (12.4 g, yield 68%).

¹ H-NMR: δ 6.52 (d, 1H), 6.58 (m, 6H), 7.41 (d, 1H), 7.50 (m, 6H), 7.61 (t, 1H), 7.89 (d, 2H), 7.99 ( s, 2H), 8.13 (d, 1H), 8.37 (m, 4H)

[LCMS]: 540

[Synthesis Example 2] Synthesis of Compound A-1-2

Instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 2-(biphenyl-4-yl)-4-(4-bromophenyl)-6-phenyl- Except that 1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain target compound A-1-2 (3.2 g, yield 87%).

¹ H-NMR: δ 6.55 (d, 1H), 6.60 (m, 5H), 7.26 (m, 3H), 7.55 (m, 10H), 7.75 (m, 2H), 7.92 (d, 2H), 8.00 ( d, 1H), 8.12 (d, 1H), 8.36 (m, 2H)

[LCMS]: 552

[Synthesis Example 3] Synthesis of Compound A-1-7

Instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 2-(4-bromophenyl)-4-phenyl-6-(4-(pyridin-3- Except that yl)phenyl)-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain the target compound A-1-7 (2.2 g, yield 74%).

[LCMS]: 617

[Synthesis Example 4] Synthesis of Compound A-1-14

2-(4-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. )-6-phenyl-1,3,5-triazine, except that the same process as in [Synthesis Example 1] to obtain the target compound A-1-14 (4.1g, yield 88%).

[LCMS]: 630

[Synthesis Example 5] Synthesis of Compound A-1-18

2-(4-chlorophenyl)-4-(dibenzo[b,d]thiophen-3-yl instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. )-6-phenyl-1,3,5-triazine, except that the same process as in [Synthesis Example 1] to obtain the target compound A-1-18 (4.1g, yield 52%).

[LCMS]: 646

[Synthesis Example 6] Synthesis of Compound A-1-22

2-(4-chlorophenyl)-4-(9,9-dimethyl-9H-fluoren-2 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. -yl)-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was carried out to obtain the target compound A-1-22 (3.6g, yield 46%) .

[LCMS]: 656

[Synthesis Example 7] Synthesis of Compound A-3-2

Compound S-9 obtained in Preparation Example 4 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(biphenyl) instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Except that -4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was carried out, and the target compound A-3-2. (1.9 g, yield 86%).

[LCMS]: 783

[Synthesis Example 8] Synthesis of Compound A-3-7

Compound S-9 obtained in Preparation Example 4 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(biphenyl) instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. The same procedure as in [Synthesis Example 1] was carried out for the desired compound A-3-7 (2.8, except that -4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine was used. g, yield 67%).

[LCMS]: 784

[Synthesis Example 9] Synthesis of Compound A-3-14

Compound S-10 obtained in Preparation Example 5 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(4 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1], target compound A -3-14 (3.2 g, yield 80%) was obtained.

[LCMS]: 873

[Synthesis Example 10] Synthesis of Compound A-3-18

Compound S-10 obtained in Preparation Example 5 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(4 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine, except that the same purpose as in [Synthesis Example 1] was performed Compound A-3-18 (1.2 g, yield 88%) was obtained.

[LCMS]: 890

[Synthesis Example 11] Synthesis of Compound A-3-22

Compound S-11 obtained in Preparation Example 6 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(4 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -The same procedure as in [Synthesis Example 1] was performed except that -chlorophenyl)-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine was used. To obtain the target compound A-3-22 (1.8g, yield 73%).

[LCMS]: 900

[Synthesis Example 12] Synthesis of Compound A-4-1

The same procedure as for [Synthesis Example 1] was performed, except that Compound S-14 obtained in Preparation Example 9 was used instead of Compound S-2 used in Synthesis Example 1, (3.3 g, yield) 81%).

[LCMS]: 706

[Synthesis Example 13] Synthesis of Compound A-4-9

Compound S-15 obtained in Preparation Example 10 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(4 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-phenyl-6-(3-(pyridin-3-yl)phenyl)-1,3,5-triazine, except that the target compound by performing the same process as in [Synthesis Example 1] A-4-9 (2.5 g, yield 77%) was obtained.

¹ H-NMR: δ 7.20~7.52(m, 10H), 7.63~7.68(m, 3H), 7.95(t, 2H), 8.34(m, 2H), 8.79(s, 1H),

[LCMS]: 783

[Synthesis Example 14] Synthesis of Compound A-4-14

Compound S-16 obtained in Preparation Example 11 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(4 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was performed. Compound A-4-14 (3.0 g, yield 87%) was obtained.

[LCMS]: 796

[Synthesis Example 15] Synthesis of Compound A-4-18

Compound S-13 obtained in Preparation Example 8 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(4 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -chlorophenyl)-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was performed Compound A-4-18 (4.1 g, yield 74%) was obtained.

[LCMS]: 828

[Synthesis Example 16] Synthesis of Compound A-4-22

Compound S-12 obtained in Preparation Example 7 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(4 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -chlorophenyl)-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine was used, and the same procedure as in [Synthesis Example 1] was performed. This gave the desired compound A-4-22 (1.2 g, yield 82%).

[LCMS]: 898

[Synthesis Example 17] Synthesis of Compound A-5-2

Compound S-18 obtained in Preparation Example 12 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(biphenyl) instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Except that -4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was carried out, and the desired compound A-5-2. (1.9 g, yield 64%).

¹ H-NMR: δ 6.55 (d, 2H), 6.68 (d, 2H), 6.99 (m, 4H), 7.28 (m, 3H), 7.48 (m, 8H), 7.56 (m, 5H), 7.92 ( d, 2H), 8.40 (m, 2H)

[LCMS]: 632

[Synthesis Example 18] Synthesis of Compound A-5-14

Compound S-18 obtained in Preparation Example 12 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(4 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was performed. Compound A-5-14 (2.0 g, yield 66%) was obtained.

[LCMS]: 646

[Synthesis Example 19] Synthesis of Compound D-1-1

Compound S-19 obtained in Preparation Example 13 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 [2-(4-chloronaphthalen-1-yl)- 4,6-diphenyl-1,3,5-triazine], except that the same procedure as in [Synthesis Example 1] was carried out to obtain the target compound D-1-1 (1.4g, yield 71%).

¹ H-NMR: δ 6.42 (d, 1H), 6.61 (m, 5H), 7.48 (m, 12H), 7.99 (m, 2H), 8.11 (d, 1H), 8.36 (m, 4H), 8.50 ( d, 1H)

[LCMS]: 590

[Synthesis Example 20] Synthesis of Compound D-1-5

Compound S-20 obtained in Preparation Example 14 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 [2-(4-chloronaphthalen-1-yl)- Except that 4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine] was used, the same procedure as in [Synthesis Example 1] was carried out, and the target compound D- 1-5 (2.4 g, yield 70%) was obtained.

[LCMS]: 680

[Synthesis Example 21] Synthesis of Compound D-1-11

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and in Preparation Example 13 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. The same procedure as in [Synthesis Example 1] was performed, except that the obtained compound S-19 [2-(4-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine] was used. The desired compound D-1-11 (4.5 g, yield 61%) was obtained.

[LCMS]: 640

[Synthesis Example 22] Synthesis of Compound D-1-14

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and in Preparation Example 15 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Except the obtained compound S-21 [2-(4-chloronaphthalen-1-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine] Then, the same procedure as in [Synthesis Example 1] was performed to obtain target compound D-1-14 (1.7 g, yield 80%).

[LCMS]: 730

[Synthesis Example 23] Synthesis of Compound D-1-21

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and in Preparation Example 13 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. The same procedure as in [Synthesis Example 1] was performed, except that the obtained compound S-19 [2-(4-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine] was used. The desired compound D-1-21 (3.7 g, yield 79%) was obtained.

[LCMS]: 640

[Synthesis Example 24] Synthesis of Compound D-1-24

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and in Preparation Example 15 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Except the obtained compound S-21 [2-(4-chloronaphthalen-1-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine] Then, the same procedure as in [Synthesis Example 1] was performed to obtain target compound D-1-24 (2.0 g, yield 77%).

[LCMS]: 730

[Synthesis Example 25] Synthesis of Compound D-2-2

Compound S-22 obtained in Preparation Example 17 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 [2-(biphenyl-4-yl)-4- (4-chloro-2,6-dimethylphenyl)-6-phenyl-1,3,5-triazine], except that the target compound D-2-2 ( 3.5g, yield 88%).

¹ H-NMR: δ 2.33 (s, 6H), 6.14 (s, 2H), 6.41 (d, 1H), 6.58 (m, 3H), 7.26 (m, 3H), 7.54 (m, 10H), 7.76 ( m, 2H), 8.00 (d, 1H), 8.11 (d, 1H), 8.39 (m, 2H)

[LCMS]: 644

[Synthesis Example 26] Synthesis of Compound D-2-12

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and in Preparation Example 17 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Except for using the obtained compound S-22 [2-(biphenyl-4-yl)-4-(4-chloro-2,6-dimethylphenyl)-6-phenyl-1,3,5-triazine], [ Synthesis Example 1] was performed to obtain the target compound D-2-12 (2.5 g, yield 57%).

[LCMS]: 694

[Synthesis Example 27] Synthesis of Compound D-2-22

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and in Preparation Example 17 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Except for using the obtained compound S-22 [2-(biphenyl-4-yl)-4-(4-chloro-2,6-dimethylphenyl)-6-phenyl-1,3,5-triazine], [ Synthesis Example 1] was performed to obtain the target compound D-2-22 (2.9 g, yield 67%).

[LCMS]: 694

[Synthesis Example 28] Synthesis of Compound A-2-1

2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 Except for the use, the same procedure as in [Synthesis Example 1] was performed to obtain the target compound A-2-1 (4.9 g, yield 77%).

¹ H-NMR: δ 6.42 (d, 2H), 6.67 (m, 5H), 6.84 (d, 1H), 7.07 (t, 1H), 7.26 (t, 1H), 7.48 (m, 8H), 8.02 ( d, 1H), 8.20 (d, 1H), 8.38 (m, 4H)

[LCMS]: 540

[Synthesis Example 29] Synthesis of Compound A-2-2

Instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 2-(biphenyl-4-yl)-4-(3-chlorophenyl)-6-phenyl- Except that 1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain the target compound A-2-2 (3.3 g, yield 81%).

[LCMS]: 616

[Synthesis Example 30] Synthesis of Compound A-2-7

Instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 2-(3-chlorophenyl)-4-phenyl-6-(4-(pyridin-3- Except that yl)phenyl)-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain the target compound A-2-7 (3.2g, yield 69%).

[LCMS]: 617

[Synthesis Example 31] Synthesis of Compound A-2-14

2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. )-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] to obtain the target compound A-2-14 (3.2g, yield 69%).

[LCMS]: 630

[Synthesis Example 32] Synthesis of Compound B-2-1

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(3 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4,6-diphenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1], the target compound B-2-1 (4.6g, yield 77%) Got

[LCMS]: 590

[Synthesis Example 33] Synthesis of Compound B-2-2

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(biphenyl) instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. Except that -4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was carried out, and the target compound B-2-2. (2.2 g, yield 70%).

[LCMS]: 666

[Synthesis Example 34] Synthesis of Compound B-2-7

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(3 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine, except for using the same process as in [Synthesis Example 1], the target compound B -2-7 (2.4 g, yield 72%) was obtained.

[LCMS]: 667

[Synthesis Example 35] Synthesis of Compound B-2-14

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(3 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was performed. Compound B-2-14 (2.0 g, yield 62%) was obtained.

[LCMS]: 680

[Synthesis Example 36] Synthesis of Compound C-2-1

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(3 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4,6-diphenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1], the target compound C-2-1 (5.1g, yield 55%) Got

[LCMS]: 590

[Synthesis Example 37] Synthesis of Compound C-2-2

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(3 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was performed. Compound C-2-2 (2.9 g, yield 82%) was obtained.

[LCMS]: 666

[Synthesis Example 38] Synthesis of Compound C-2-7

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(3 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine, except for using the same process as in [Synthesis Example 1], the target compound C -2-7 (2.9 g, yield 82%) was obtained.

[LCMS]: 667

[Synthesis Example 39] Synthesis of Compound C-2-14

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(3 instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine. -Chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was used. Compound C-2-14 (2.6 g, yield 80%) was obtained.

[LCMS]: 680

[Example 1] Fabrication of green organic electroluminescent device

The compound A-1-1 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.

first. The glass substrate coated with ITO (Indium tin oxide) with a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, dried, transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed for 5 minutes using UV. The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/85 wt% mCBP + 15 wt% A-1-1 (30 nm)/ DS-505 (Doosan Corporation An organic electroluminescent device was fabricated by stacking electrons, 30 nm)/LiF (1 nm)/Al (200 nm) in this order. The structures of NPB and mCBP used at this time are as follows.

[Examples 2 to 27] Preparation of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 below was used instead of Compound A-1-1 used as a dopant in forming the light emitting layer in Example 1.

[Comparative Example 1] Preparation of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq ₃ was used instead of Compound A-1-1 used as a dopant in forming the light emitting layer in Example 1. The structure of Alq ₃ used at this time is as follows.

[Comparative Example 2] Fabrication of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Com-1 below was used instead of Compound A-1-1 used as a dopant in forming the light emitting layer in Example 1. The structure of Com-1 used at this time is as follows.

[Evaluation Example 1]

Example 1 For the green organic electroluminescent devices produced in bet 27 and comparative examples 1 and 2, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. Shown.

Sample Dopant Driving voltage (V) Luminous peak (nm) Current efficiency (cd/A) Example 1 A-1-1 3.9 530 50 Example 2 A-1-2 4.2 530 53 Example 3 A-1-7 3.6 548 42 Example 4 A-1-14 3.8 530 45 Example 5 A-1-18 4.0 528 46 Example 6 A-1-22 4.3 525 45 Example 7 A-3-2 4.3 545 55 Example 8 A-3-7 3.9 545 58 Example 9 A-3-14 4.0 540 51 Example 10 A-3-18 4.1 540 50 Example 11 A-3-22 4.3 540 49 Example 12 A-4-1 4.1 540 48 Example 13 A-4-9 4.0 538 49 Example 14 A-4-14 4.0 545 51 Example 15 A-4-18 4.3 545 44 Example 16 A-4-22 3.9 545 50 Example 17 A-5-2 4.2 518 41 Example 18 A-5-14 4.2 520 42 Example 19 D-1-1 4.3 545 43 Example 20 D-1-5 4.5 548 42 Example 21 D-1-11 4.4 515 43 Example 22 D-1-14 4.4 520 41 Example 23 D-1-21 4.3 515 44 Example 24 D-1-24 4.4 520 42 Example 25 D-2-2 4.2 525 51 Example 26 D-2-12 4.3 528 53 Example 27 D-2-22 4.2 520 50 Comparative Example 1 Alq ₃ 5.6 525 13 Comparative Example 2 Com-1 4.3 540 40

As shown in Table 1 above, the green organic EL devices of Examples 1 to 27 using Compounds A-1-1 to D-2-22 according to the present invention as a light emitting layer material (specifically, a dopant) together with mCBP, It was found that the green organic EL device of Comparative Example 1 using mCBP and Alq ₃ was superior in terms of driving voltage, emission peak, and current efficiency.

On the other hand, the green organic EL devices of Examples 1 to 27 were superior in current efficiency to the green organic EL devices of Comparative Example 2 using the conventional compound Com-1.

[Example 28] Fabrication of organic EL device

The compound A-2-1 synthesized in Synthesis Example 28 was subjected to a high-purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with a thin film of ITO (Indium tin oxide) at a thickness of 1500 Å was washed with distilled water. After washing with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, dried and transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes and then vacuum-deposited. The substrate was transferred to.

M-MTDATA (60 nm)/TCTA (80 nm)/ 90 wt% Compound A-2-1 + 10 wt% Ir(ppy) ₃ (300 nm)/BCP (10 nm)/Alq ₃ (30) on the prepared ITO transparent electrode nm)/LiF (1 nm)/Al (200 nm). The structures of m-MTDATA, TCTA, Ir(ppy) ₃ and BCP used at this time are as follows.

[Examples 29 to 39] Fabrication of organic EL device

An organic EL device was manufactured in the same manner as in Example 28, except that each of the compounds shown in Table 2 was used instead of Compound A-2-1 used as a light-emitting host material in the formation of the light-emitting layer in Example 28.

[Comparative Example 3] Fabrication of organic EL device

An organic EL device was manufactured in the same manner as in Example 28, except that CBP was used instead of Compound A-2-1 used as a light-emitting host material when the light-emitting layer was formed in Example 28. The structure of the CBP used at this time is as follows.

[Comparative Example 4] Fabrication of organic EL device

An organic EL device was manufactured in the same manner as in Example 28, except that the following compound Com-2 was used instead of the compound A-2-1 used as a light emitting host material in the formation of the light emitting layer in Example 28. The structure of Com-2 used at this time is as follows.

[Evaluation Example 2]

For each of the organic EL devices produced in Examples 28 to 39 and Comparative Examples 3 and 4, driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. .

Sample Host Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 28 A-2-1 6.31 518 54 Example 29 A-2-2 6.42 518 54 Example 30 A-2-7 6.66 518 51 Example 31 A-2-14 6.7 517 51 Example 32 B-2-1 6.7 515 53 Example 33 B-2-2 6.22 518 55 Example 34 B-2-7 6.77 518 51 Example 35 B-2-14 6.32 516 54 Example 36 C-2-1 6.90 518 58 Example 37 C-2-2 6.51 518 54 Example 38 C-2-7 6.17 518 53 Example 39 C-2-14 6.21 517 53 Comparative Example 3 CBP 6.90 516 50 Comparative Example 4 Com-2 6.93 516 48

As shown in Table 2, the organic EL devices of Examples 28 to 39 using the compounds A-2-1 to C-2-14 according to the present invention as hosts for the light emitting layer, CBP and Com-2, which are conventional hosts, were used. It was found that the organic EL devices of Comparative Examples 3 to 4, respectively, were superior in terms of driving voltage, emission peak, and current efficiency.

100: anode, 200: cathode,
300: organic layer, 310: hole injection layer,
320: hole transport layer, 330: light emitting layer,
340: electron transport layer, 350: electron injection layer

Claims (13)

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

(In the formula 1,
A ring is a C ₆ ~ C ₆₀ polycyclic aromatic ring,
X is selected from the group consisting of C(R ₂ )(R ₃ ), N(R ₄ ), O and S,
Y ₁ to Y ₃ are the same as or different from each other, and each independently N or CR ₅ , provided that at least one of Y ₁ to Y ₃ is N, and when CR ₅ is plural, a plurality of R _{5 s} are the same or different from each other Different,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently selected from the group consisting of C ₆ to C ₆₀ aryl groups and heteroaryl groups having 5 to 60 nuclear atoms,
L ₁ is a C ₆ ~C ₆₀ arylene group,
a is an integer from 0 to 4,
R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to alkynyl group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, and selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of,
The polycyclic aromatic ring of the A ring, an arylene group of L _1, an aryl group of Ar ₁ and Ar ₂ , a heteroaryl group, an alkyl group of R ₁ to R ₅ , an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group , Heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group are each independently deuterium, halogen, cyan No 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, 3 to 40 nuclear atoms heterocycloalkyl group , C ₆ ~ C ₆₀ aryl group, a nuclear number of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group , C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C of ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine Substituted or unsubstituted with one or more substituents selected from the group consisting of an oxide group and an arylamine group of C ₆ to C ₆₀ , where the plurality of substituents are the same or different from each other). According to claim 1,
The compound represented by Formula 1 is a compound represented by Formula 2 below:
[Formula 2]

(In the formula 2,
B ring is a C ₆ ~ C ₄₀ monocyclic aromatic ring or C ₆ ~ C ₄₀ polycyclic aromatic ring,
X, Y ₁ to Y ₃ , L ₁ , Ar ₁ , Ar ₂ , a, and R ₁ are each as defined in claim 1). According to claim 1,
The A ring is a naphthalene ring, anthracene ring, tetracene ring, pyrene ring, phenanthrene ring, phenalene ring, benzoanthracene ring, benzopyrene ) Ring, triphenylene ring, chrysene ring, pentaphene ring, pentacene ring, and a compound selected from the group consisting of condensed rings between the two rings. According to claim 1,
All of Y ₁ to Y ₃ are N compounds. According to claim 1,
R ₁ is a substituent selected from the group consisting of hydrogen and the following substituents S1 to S24,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a compound selected from the group consisting of the following substituents S1 to S23:

(In the substituents S1 to S24,
R ₆ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 3 to 7:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

(In the above formula 3 to 7,
X, Y ₁ to Y ₃ , L ₁ , Ar ₁ , Ar ₂ , a, and R ₁ are each as defined in claim 1). According to claim 1,
The compound represented by Formula 1 is a compound represented by Formula 8 or 9 below:
[Formula 8]

[Formula 9]

(In the formulas 8 and 9,
B ring is a C ₆ ~ C ₄₀ monocyclic aromatic ring or C ₆ ~ C ₄₀ polycyclic aromatic ring,
X, Y ₁ to Y ₃ , Ar ₁ , Ar ₂ , a, and R ₁ are each as defined in claim 1,
b is an integer from 0 to 4,
c is an integer from 0 to 6,
R ₆ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 10 to 12:
[Formula 10]

[Formula 11]

[Formula 12]

(In the formulas 10 to 12,
B ring is a C ₆ ~ C ₄₀ monocyclic aromatic ring or C ₆ ~ C ₄₀ polycyclic aromatic ring,
X, Y ₁ to Y ₃ , Ar ₁ , Ar ₂ , a, and R ₁ are each as defined in claim 1,
b is an integer from 0 to 4,
c is an integer from 0 to 6,
R ₆ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 13 to 21:
[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

(In the above formula 13 to 21,
X, Y ₁ to Y ₃ , Ar ₁ , Ar ₂ , R ₁ are the same as defined in claim 1,
R ₆ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino 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, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ arylamine group is selected from the group consisting of,
d and e are each 0 or 1,
R ₇ is C ₁ ~ C ₄₀ alkylene group, C ₂ ~ C ₄₀ alkenylene group, C ₂ ~ C ₄₀ alkynylene group, C ₃ ~ C ₄₀ cycloalkylene group, 3 to 40 nuclear atoms hetero It is selected from the group consisting of a cycloalkylene group, an arylene group of C ₆ ~ C ₆₀ , and a heteroarylene group having 5 to 60 nuclear atoms,
Plural R ₈ are the same or different and each is independently selected from the group consisting of C ₆ ~ C ₆₀ of a C ₆ ~ C ₆₀ aryl group and the number of nuclear atoms of 5 to 60 heteroarylene group each other,
The alkylene group, alkenylene group, alkynylene group, cycloalkylene group, heterocycloalkylene group, arylene group and heteroarylene group of R ₇ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ of Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nucleus Heteroaryl group having 5 to 60 atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C group of ₁ to alkylboronic of C _40, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine Substituted or unsubstituted with one or more substituents selected from the group consisting of groups, preferably deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₃₀ aryl group, 5 to ₆ nuclear atoms It may be unsubstituted or substituted with one or more substituents selected from the group consisting of 30 heteroaryl groups. In this case, when the substituents are plural, they are the same or different from each other). 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 organic material layer of the one or more layers is an organic electroluminescent device comprising a compound according to any one of claims 1 to 9. The method of claim 10,
The organic material layer including the compound is an organic electroluminescent device that is a light emitting layer. The method of claim 10,
The light emitting layer includes a host and a dopant,
The host is an organic electroluminescent device comprising the compound. The method of claim 10,
The light emitting layer includes a host and a dopant,
The dopant is an organic electroluminescent device comprising the compound.

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