WO2020130660A1 - Organic compound and organic electroluminescent device using same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using same and, more particularly, to a compound having excellent thermal stability, electrochemical stability, light-emitting ability, and hole/electron transport ability, and an organic electroluminescent device including the compound in one or more organic material layers so that properties such as light-emitting efficiency, driving voltage, and lifespan are improved.

Description

Organic compounds and organic electroluminescent devices 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 an organic electroluminescent device (hereinafter referred to as an'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 having excellent thermal stability, electrochemical stability, light emitting ability, and hole/electron transporting 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 is an integer of 2 or 3,

b is 0 or 1,

However, a+b is 3,

A plurality of A rings are the same as or different from each other, and each independently a C ₆ ~ C ₆₀ polycyclic aromatic ring,

A plurality of X is the same or different from each other, each independently selected from the group consisting of C (R ₂ ) (R ₃ ), N (R ₄ ), O and S,

A plurality of L ₁ are the same as or different from each other, and each independently a single bond or an arylene group of C ₆ to C ₆₀ ,

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 is selected from the group consisting of C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms,

c is an integer from 0 to 4,

The plurality of R _1, and R ₂ to R ₅ 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 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, is selected from the group consisting of C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, 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 , a heteroaryl group, an alkyl group of R ₁ to R ₅ , an alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl A group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently hydrogen, deuterium, halogen, cyano group , Nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 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 ~ aryl of C ₆₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide Group and C ₆ to C ₆₀ are substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, where the plurality of substituents are the same or different from each other).

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

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.

** Explanation of sign **

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

Hereinafter, the present invention will be described in detail.

<New organic 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 composed of 2 to 3 N-containing condensed heteroaromatic ring moieties bonded to each other through an N-containing 6-membered heterocycle as a linker.

In the compound of Formula 1, the N-containing condensed heteroaromatic ring moiety is a group such as a benzene ring, a naphthalene ring, anthracene ring, pyrene ring, etc., on one side of a phenoxazine moiety having a P-type characteristic. 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 absorbency. 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, the compound of the present invention has a high triplet energy and a small singlet and triplet energy difference (ΔEST). For this reason, when the compound of the present invention is used as a light emitting layer material of an organic electroluminescent device, the compound of the present invention can 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, which in the end The number of excitons contributing to the light emission in the light emitting layer is substantially increased to improve the luminous efficiency and absolute quantum efficiency of the device, and the durability and stability of the device are improved to significantly increase the lifetime characteristics of the device.

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, a is an integer of 2 or 3, b is 0 or 1, provided that a+b is 3. According to an example, a may be 2 and b may be 1. Specifically, the compound of Formula 1 may be a compound represented by Formula 8, but is not limited thereto. According to another example, a may be 3 and b may be 0. Specifically, the compound of Formula 1 may be a compound represented by Formula 9 below, but is not limited thereto.

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. Here, each ring in the polycyclic aromatic ring may be the same as 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, but is not limited thereto. Does not.

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 , a, b, c and R ₁ are each as defined in Formula 1,

The plurality of B rings are the same or different from each other, and each independently a C ₆ to C ₄₀ monocyclic aromatic ring or a C ₆ to C ₄₀ polycyclic aromatic ring, and preferably a benzene ring, a naphthalene ring, anthracene ring, tetracene ( tetracene ring, pyrene ring, phenanthrene ring, phenalene ring, benzoanthracene ring, benzopyrene ring, triphenylene ring, chrysene (chrysene) ring, a pentaphene (pentaphene) ring, a pentacene (pentacene) ring, and may be a condensed ring between the two rings, but is not limited thereto.

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 , a, b, c and R ₁ are as defined in Formula 1, respectively.

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

Here, when c is 0, it means that hydrogen is not substituted with the substituent R ₁ , and when c is an integer of 1 to 4, a plurality of R ₁ are 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 heteroaryl groups of 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 ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ Is selected from the group consisting of arylphosphine oxide groups and C ₆ to C ₆₀ arylamine groups, preferably C ₆ to C ₆₀ aryl groups, heteroaryl groups having 5 to 60 nuclear atoms, and C ₆ to C ₆₀ It may be selected from the group consisting of an arylamine group, and more preferably may be selected from the group consisting of C ₆ ~ C ₆₀ aryl group and C ₆ ~ C ₆₀ arylamine group.

According to an example, R ₁ may be selected from the group consisting of hydrogen and the following substituents S1-1 to S1-27.

In the substituents S1-1 to S1-27,

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, a plurality of Xs are the same as or different from each other, and each independently selected from the group consisting of C(R ₂ )(R ₃ ), N(R ₄ ), O, and S, 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, L ₁ is a divalent linker group, a plurality of L ₁ are the same or different from each other, each independently a single bond or C ₆ ~ C ₆₀ arylene group, preferably a single bond Or it may be a C ₆ ~ C ₄₀ arylene group. Specifically, examples of L ₁ include a single bond, a phenylene group, a biphenylene group, a terphenylene group, and a divalent naphthalene group, but are not limited thereto.

According to an example, a plurality of L ₁ are the same as or different from each other, and may each independently be a single bond or a phenylene group.

Here, when L ₁ is a phenylene group, the N-containing condensed heteroaromatic ring moiety and the N-containing 6-membered heterocyclic ring may be bonded to each other in a para position with respect to L ₁ . In this case, the compound represented by Formula 1 may be embodied as a compound represented by Formula 8 or 9 below. Here, both of the compound of Formula 8 and the compound of Formula 9, since the bipolar property is increased, the luminous efficiency is high, and injection of electrons/electrons is easy, it can be used as a light emitting layer material of an organic electroluminescent device, specifically a host or dopant At this time, it is possible to increase the current efficiency while lowering the driving voltage of the organic EL device.

In Chemical Formulas 8 and 9,

X, Y ₁ to Y ₃ , Ar ₁ , c and R ₁ are each as defined in Formula 1,

d is 0 or 1,

The plurality of B rings is as defined in Formula 2.

In addition, in the compound represented by Chemical Formula 1, Y ₁ to Y ₃ are the same as or different from each other, and each independently N or CR ₅ , but at least one of Y ₁ to Y ₃ is N, wherein CR ₅ is plural In the case of, 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.

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 having C ₆ to C ₆₀ , a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C ₆ to C ₆₀ .

In addition, in the compound represented by Formula 1, Ar ₁ is selected from the group consisting of C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms, preferably C ₆ ~ C ₄₀ aryl group and It may be selected from the group consisting of a heteroaryl group having 5 to 40 nuclear atoms.

Specifically, Ar ₁ may be a substituent selected from the group consisting of the following substituents S2-1 to S2-26.

In the substituents S2-1 to S2-26,

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 Chemical Formula 1, the polycyclic aromatic ring of the A ring, the arylene group of L _1, the aryl group of Ar _1, the heteroaryl group, the alkyl group of R ₁ to R ₅ , alkenyl group, alkynyl group, cycloalkyl group, heterocyclo Alkyl 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 are each independently deuterium , Halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 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 ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ Substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphine oxide group and an arylamine group of C ₆ to C ₆₀ , preferably deuterium, halogen, cyano group, nitro group, C ₁ to C ₂₀ alkyl group , C ₆ ~ C ₃₀ aryl group, may be substituted or unsubstituted with one or more substituents selected from the group consisting of 5 to 30 heteroaryl groups. 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 Formula 10 or 11 below, but is not limited thereto.

In Chemical Formulas 10 and 11,

A plurality of B rings are as defined in Formula 2 above,

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

d is 0 or 1,

e is 0 or 1,

Here, when e is 0, it means that hydrogen is not substituted with a substituent R ₇ , and when e is 1, R ₇ is 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,

f is 0 or 1,

Here, when f is 0, it means that hydrogen of R ₇ is not substituted with a substituent -N(R ₇ )(R ₈ ), and when f is 1, R ₈ and R ₉ are the same or different from each other, respectively independently C ₆ ~ C _{60-C 6} ~ C ₆₀ aryl group and a nuclear atoms are selected from the group consisting of 5 to 60 groups heteroarylene, preferably from C ₆ ~ C ₄₀ aryl group and the number 5 to the nucleus of atoms of It may be selected from the group consisting of 40 heteroarylene groups, specifically, a 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. Can be,

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 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 Substituted or unsubstituted with one or more substituents selected from the group consisting of 30 heteroaryl groups, preferably deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₃₀ aryl group, nucleus It may be unsubstituted or substituted with one or more substituents selected from the group consisting of 5 to 30 heteroaryl groups. 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 12 to 21, but is not limited thereto.

In the above formulas 12 to 21,

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

d, e, f and R ₇ to R ₉ are as defined in Chemical Formulas 8 to 11, respectively.

Compound represented by the formula (1) according to the present invention described above may be more specific to the following exemplary compounds, such as compounds A-1-1 to C-5-28, but is not limited thereto.

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 (anode), a cathode (cathode) and at least one organic material layer interposed between the anode and the cathode (介在), at least one of the one or more organic material layers 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 Can be

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 can be a compound. 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. Also, a hole blocking layer (not shown) may be positioned between the light emitting layer 330 and the electron transport layer 340. The organic electroluminescent device of the present invention includes at least one of the organic material layers 300 (eg, the light emitting layer ( 330), a hole blocking layer (not shown) or an electron transport layer 340], except that it contains a compound represented by the formula (1), by forming an organic material layer and an electrode using materials and methods known in the art Can be produced.

The organic material 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.

In addition, the hole injection layer, the hole transport layer, the electron transport layer and the electron injection layer are not particularly limited, and common materials known in the art may be used.

Hereinafter, the present invention will be described in detail through examples as follows. 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), 1-bromo-2-nitrobenzene (13.9 g, 69 mmol) was added to a 2-neck flask, KOH (5.4 g, 96 mmol) was added, and DMSO (150 mL), followed by heating and stirring for 8 hours. After completion of the reaction, the solution was filtered silica and the solvent was removed. After purification by column chromatography (MC:Hexane=1:3), an oil-type yellow compound S-1 (12.8g, yield: 70%) was obtained. .

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 at 120°C. Stir for hours. The reactant was extracted with MC (methylene chloride), filtered through silica, and then the solvent was removed, followed by washing with MeOH to obtain 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 the same procedure as in <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

With <Step 2> of [Preparation Example 1], except that Compound S-3 (10 g, 32 mmol) obtained in <Step 1> was used instead of Compound S-1 used in <Step 2> of Preparation Example 1 The same procedure was performed 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 the same procedure 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

With <Step 2> of [Preparation Example 1], except that Compound S-5 (15 g, 47 mmol) obtained in <Step 1> was used instead of Compound S-1 used in <Step 2> of Preparation Example 1 The same procedure was performed 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, 2-bromo-4-chloro-1-nitrobenzene (16.3g, 51mmol) was used, and the same procedure as in <Step 1> of [Preparation Example 1] was carried out, followed by target compound S-7 (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

<Step 1> of [Preparation Example 1], except that Compound S-7 (8 g, 27 mmol) obtained in <Step 1> was used instead of Compound S-1 used in <Step 2> of Preparation Example 1 The same procedure was performed to obtain the target compound S-8 (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

Compound S-8 (10 g, 37 mmol), diphenylamine (7.5 g, 44 mmol) obtained in <Step 2> at room temperature was added to a 2-neck flask, and then Pd ₂ (dba) ₃ (1.35 g, 1.5 mmol) and NaOt -Bu (8.2g, 74mmol) was added, Toluene (200 mL) was added, and then P(t-bu) ₃ (0.06g, 3mmol) was added 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 compound 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, 35 mmol), dibenzo[b,d]furan-2-ylboronic acid (9.4 g, 44 mmol) obtained in <Step 2> of Preparation Example 4 at room temperature was added to a 2-neck flask, and , Pd(PPh ₃ ) ₄ (1.7g, 1.5mmol) and NaOH (2.9g, 74mmol) were added. 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=1:2). Got

¹ H-NMR: δ 4.00 (s, 1H), 6.62 (m, 2H), 6.73 (d, 1H), 7.09 (d, 1H), 7.31 (m, 4H), 7.59 (m, 4H), 8.00 ( m, 2H), 8.11 (d, 1H),

[LCMS]: 399

[Preparation Example 6] Synthesis of Compound S-12

<Step 1>-Synthesis of Compound S-11

Compound S-2 (10 g, 37 mmol), 1-bromo-4-iodobenzene (104 g, 37 mmol), CuI (1.4 g, 7.4 mmol), K ₂ CO ₃ (20.4 g, 148 mmol) obtained in Preparation Example 1 at room temperature ) Was added to a 2-neck flask, and L-proline (1.7 g, 14.8 mmol) and DMSO (200 mL) were added thereto, followed by stirring at 120° C. for 48 hours. After completion of the reaction, the solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:4), then recrystallized with toluene to give a light yellow powder compound S-11 (10 g, yield: 70%). Got

¹ H-NMR: δ 4.00 (s, 1H), 6.62 (m, 2H), 6.73 (d, 1H), 7.09 (d, 1H), 7.31 (m, 4H), 7.59 (m, 4H), 8.00 ( m, 2H), 8.11 (d, 1H),

[LCMS] :388

<Step 2> Synthesis of Compound S-12

Compound S-11 (10 g, 25 mmol), Pd(dppf)Cl ₂ (0.73 g 1 mmol), KOAc (5 g, 50 mmol), Bis (pinacolate) diboron (7.62 g) obtained at <Step 1> at room temperature 30 mmol), X-phos (2.1 g, 4.4 mmol) was placed in a 2-neck flask, and 1.4-Dioxane (200 ml) was added thereto while refluxing while maintaining nitrogen conditions. After reaction for 12 hours and the reaction was terminated, the solution was filtered through silica to remove the solvent to obtain a white powder compound S-12 (8.9 g, yield: 82%).

¹ H-NMR: δ 1.26 (s, 12H), 6.42 (m, 3H), 6.67 (m, 4H), 7.07 (d, 2H), 7.28 (t, 1H), 7.41 (d, 1H), 7.60 ( t, 1H), 7.98 (d, 1H), 8.12 (d, 1H),

[LCMS] :435

[Preparation Example 7] Synthesis of Compound S-14

<Step 1>-Synthesis of Compound S-13

The target compound S- was subjected to the same procedure as in Step 1 of [Preparation Example 6], except that Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in <Step 1> of Preparation Example 6 13 (10.2 g, Yield: 43%).

¹ H-NMR: δ 6.35 (m, 3H), 6.66 (m, 3H), 7.20 (d, 2H), 7.86 (m, 4H), 8.14 (d, 2H), 8.43 (d, 2H),

[LCMS]: 438

<Step 2>-Synthesis of Compound S-14

The same procedure as in <Step 2> of [Preparation Example 6] was performed, except that Compound S-13 obtained in <Step 1> was used instead of Compound S-12 used in <Step 2> of Preparation Example 6. The desired compound S-14 (10.2 g, yield: 83%) was obtained.

¹ H-NMR: δ 1.28 (s, 12H), 6.44 (m, 3H), 6.58 (t, 1H), 6.68 (m, 2H), 7.10 (d, 2H), 7.88 (m, 4H), 8.18 ( d, 2H), 8.90 (d, 2H),

[LCMS] :485

[Preparation Example 8] Synthesis of Compound S-16

<Step 1>-Synthesis of Compound S-15

A target compound was performed by performing the same procedure as in <Step 1> of [Preparation Example 6], except that Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in <Step 1> of Preparation Example 6 S-15 (12.8 g, yield: 62%) was obtained.

¹ H-NMR: δ 6.38 (m, 3H), 6.67 (m, 3H), 7.04 (d, 1H), 7.18 (d, 2H), 7.88 (m, 4H), 8.12 (d, 1H), 8.45 ( d, 1H), 8.93 (d, 1H),

[LCMS]: 438

<Step 2>-Synthesis of Compound S-16

The target compound S-16 (9.8) was subjected to the same procedure as <Step 2> of [Preparation Example 6], except that Compound S-15 was used instead of Compound S-11 used in <Step 2> of Preparation Example 6. g, yield: 90%).

¹ H-NMR: δ 1.26 (s, 12H), 6.42 (m, 3H), 6.59 (t, 1H), 6.69 (m, 2H), 7.03 (m, 3H), 7.80 (m, 4H), 8.12 ( d, 1H), 8.50 (d, 1H), 8.88 (d, 1H),

[LCMS] :485

[Preparation Example 9] Synthesis of Compound S-17

Compound S-12 (10 g, 23 mmol), 2,4,6-trichloro-1,3,5-triazine (2.2 g, 11 mmol) obtained in Preparation Example 6 at room temperature was placed in a 2-neck flask, and Pd(PPh ₃ ) ₄ (2g, 1.8mmol) and NaOH (1.8g, 46mmol) were added. Then, anhydrous toluene (150 mL) was added to the flask, followed by stirring at 110° C. for 9 hours. After completion of the reaction, the solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:1) to obtain yellow powder compound S-17 (14.2g, yield: 39%).

¹ H-NMR: δ 6.54 (d, 2H), 6.73 (m, 12H), 7.27 (t, 2H), 7.43 (d, 2H), 7.61 (t, 2H), 7.90 (m, 6H), 8.11 ( d, 2H)

[LCMS] :730

[Preparation Example 10] Synthesis of Compound S-18

Compound S-12 (10 g, 23 mmol), 2,4,6-trichloro-1,3,5-triazine (4.4 g, 23 mmol) obtained in Preparation Example 6 at room temperature was placed in a 2-neck flask, and then To Pd (PPh ₃ ) ₄ (0.8 g, 0.69 mmol) and NaOH (0.9 g, 23 mmol) were added. Then, anhydrous Toluene (150 mL) was added to the flask, followed by stirring at 110° C. for 4 hours. After completion of the reaction, the solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:1) to obtain a yellow powder compound S-18 (14.2g, yield: 44%).

¹ H-NMR: δ 6.53 (d, 1H), 6.63 (m, 6H), 7.26 (t, 2H), 7.41 (d, 2H), 7.60 (t, 2H), 7.99 (m, 4H)

[LCMS] :457

[Preparation Example 11] Synthesis of Compound S-19

2,4,6-trichloro-1,3,5-triazine used in Preparation Example 10 instead of 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5- Except for using triazine, the same procedure as in [Preparation Example 10] was carried out to obtain the target compound S-19 (3.2 g, yield: 70%).

¹ H-NMR: δ 6.48 (d, 1H), 6.67 (m, 6H), 7.35 (m, 5H), 7.56 (m, 3H), 7.95 (m, 4H), 8.08 (d, 1H)

[LCMS] :589

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

Compound S-2 (8.0 g, 34 mmol) and 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine (5.1 g, 17 mmol) obtained in Preparation Example 1 at 0° C. 2 -After putting in a neck flask, while maintaining nitrogen conditions, DMF (150 mL) was added to the flask, NaH (50 wt%) (1.68 g, 70 mmol) was added, followed by stirring for 5 hours, followed by stirring at room temperature for 2 hours. Then, filtered and washed with MeOH, Acetone and distilled water. After extracting the organic layer with THF, the silica was filtered and the solvent was removed and recrystallized with Xylene to obtain the target compound A-1-2 (11 g, yield: 48%).

¹ H-NMR: δ 6.44 (t, 2H), 6.67 (m, 6H), 7.26 (m, 4H), 7.54 (m, 9H), 7.76 (m, 2H), 7.99 (d, 2H), 8.12 ( d, 2H)

[LCMS] :695

[Synthesis Example 2] Synthesis of Compound A-1-4

2-([1,1':3',1''-terphenyl]-5 instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1 -yl)-4,6-dichloro-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] to perform the target compound A-1-4 (2.2g, yield: 54% ).

¹ H-NMR: δ 6.44 (d, 2H), 6.60 (m, 8H), 7.25 (t, 2H), 7.45 (m, 8H), 7.60 (t, 2H), 7.67 (s, 3H), 7.73 ( m, 4H), 8.00 (d, 2H), 8.09 (d, 2H)

[LCMS] :771

[Synthesis Example 3] Synthesis of Compound A-1-5

Instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1, 2,4-dichloro-6-(naphthalen-2-yl)-1,3, The same procedure as in [Synthesis Example 1] was performed except that 5-triazine was used to obtain the target compound A-1-5 (3.2 g, yield: 70%).

[LCMS]: 669

[Synthesis Example 4] Synthesis of Compound A-1-16

Instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1, 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl )-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was carried out to obtain the target compound A-1-16 (4.1g, yield: 88%).

[LCMS] :709

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

Instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1, 2,4-dichloro-6-(dibenzo[b,d]thiophen-3-yl )-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] to obtain the target compound A-1-20 (4.9g, yield: 61%).

[LCMS] :725

[Synthesis Example 6] Synthesis of Compound A-1-24

Instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1, 2,4-dichloro-6-(9,9-dimethyl-9H-fluoren-2 -yl)-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] was carried out to obtain the target compound A-1-24 (3.6g, yield: 46%).

[LCMS] :735

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

Compound S-12 (10 g, 23 mmol), 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine (3.3 g, 11 mmol) obtained in Preparation Example 6 at room temperature is 2 After putting in a -neck flask, Pd(PPh ₃ ) ₄ (1g, 0.9mmol) and NaOH (1.8g, 46mmol) were added. Then, anhydrous toluene (150 mL) was added to the flask, followed by stirring at 110° C. for 12 hours. After completion of the reaction, the solution was filtered through silica, the solvent was removed, and purified by column chromatography (MC:Hexane=1:1) to obtain yellow powder compound A-3-2 (14.2g, yield: 73%). .

¹ H-NMR: δ 6.55 (d, 2H), 6.67 (m, 12H), 7.26 (m, 4H), 7.53 (m, 9H), 7.76 (m, 2H), 7.91 (d, 4H), 8.00 ( d, 2H), 8.13 (d, 2H)

[LCMS] :847

[Synthesis Example 8] Synthesis of Compound A-3-4

2-([1,1':3',1''-terphenyl]-5 instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 7 -yl)-4,6-dichloro-1,3,5-triazine, except for the same procedure as in [Synthesis Example 7], the target compound A-3-4 (2.8g, yield: 67%) Got.

[LCMS] :924

[Synthesis Example 9] Synthesis of Compound A-3-5

Instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 7, 2,4-dichloro-6-(naphthalen-2-yl)-1,3, The same procedure as in [Synthesis Example 7] was obtained, except that 5-triazine was used, to obtain the target compound A-3-5 (3 g, yield: 80%).

[LCMS] :821

[Synthesis Example 10] Synthesis of Compound A-3-16

Instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 7, 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl )-1,3,5-triazine, except that the same procedure as in [Synthesis Example 7] to obtain the target compound A-3-16 (5.1g, yield: 70%).

[LCMS] :861

[Synthesis Example 11] Synthesis of Compound A-3-26

After adding compound S-2 (8.0 g, 34 mmol) and 2,4,6-trichloro-1,3,5-triazine (2.2 g, 11 mmol) obtained in Preparation Example 1 at 0° C. into a 2-neck flask , While maintaining nitrogen conditions, DMF (150mL) was added to the flask, NaH (50wt%) (1.68g, 70mmol) was added, stirred for 4 hours, then stirred at room temperature for 4 hours, filtered, It was washed with MeOH, Acetone and distilled water. Thereafter, after extracting the organic layer with THF, after filtering the silica, the solvent was removed, and recrystallized with Xylene to obtain the target compound A-3-26 (3.4 g, yield: 40%).

¹ H-NMR: δ 6.44 (t, 2H), 6.67 (m, 6H), 7.26 (m, 4H), 7.54 (m, 9H), 7.76 (m, 2H), 7.99 (d, 2H), 8.12 ( d, 2H)

[LCMS] :774

[Synthesis Example 12] Synthesis of Compound A-3-27

[Synthesis Example 1, except that the compound S-17 obtained in Preparation Example 9 was used instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1 The same process as in] was carried out to obtain the target compound A-3-27 (5.3 g, yield: 91%).

[LCMS] :927

[Synthesis Example 13] Synthesis of Compound A-3-28

[Synthesis Example 1 except that the compound S-18 obtained in Preparation Example 10 was used instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1 The same process as] was carried out to obtain the target compound A-3-28 (1.9 g, yield: 55%).

[LCMS] :850

[Synthesis Example 14] Synthesis of Compound A-3-29

Except that 2,4,6-trichloro-1,3,5-triazine was used instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 7 The same procedure as in [Synthesis Example 7] was performed to obtain target compound A-3-29 (2 g, yield: 67%).

[LCMS] :1003

[Synthesis Example 15] Synthesis of Compound A-4-2

The same procedure as [Synthesis Example 1] was performed, except that Compound S-9 obtained in Preparation Example 4 was used instead of Compound S-2 used in Synthesis Example 1, and the desired compound A-4-2 (4 g, yield: 71%).

[LCMS]: 1030

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

Compound S-9 obtained in Preparation Example 4 was used instead of Compound S-2 used in Synthesis Example 1, and 2- instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine. ([1,1':3',1''-terphenyl]-5-yl)-4, same procedure as in [Synthesis Example 1], except that 4,6-dichloro-1,3,5-triazine was used. This was carried out to obtain the target compound A-4-4 (2.2g, yield: 62%).

[LCMS]: 1106

[Synthesis Example 17] Synthesis of Compound B-1-2

The same procedure as in [Synthesis Example 1] was performed, except that Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and the desired compound B-1-2 (4.9 g, yield) : 70%).

[LCMS] :795

[Synthesis Example 18] Synthesis of Compound B-1-4

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and 2- instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine. ([1,1':3',1''-terphenyl]-5-yl)-4, same procedure as in [Synthesis Example 1], except that 4,6-dichloro-1,3,5-triazine was used. This was carried out to obtain the target compound B-1-4 (2.6 g, yield: 65%).

[LCMS] :871

[Synthesis Example 19] Synthesis of Compound B-3-2

The same procedure as [Synthesis Example 7] was performed, except that Compound S-14 obtained in Preparation Example 7 was used instead of Compound S-12 used in Synthesis Example 7, and the desired compound B-3-2 (4.4 g, yield) : 81%).

[LCMS] :948

[Synthesis Example 20] Synthesis of Compound B-3-4

Compound S-14 obtained in Preparation Example 7 was used instead of Compound S-12 used in Synthesis Example 7, and 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine instead of 2- ([1,1':3',1''-terphenyl]-5-yl)-4, 6-dichloro-1,3,5-triazine, except that the same procedure as in [Synthesis Example 7] This was carried out to obtain the target compound B-3-4 (2.9 g, yield: 80%).

[LCMS] :1024

[Synthesis Example 21] Synthesis of Compound C-1-2

The same procedure as in [Synthesis Example 1] was performed, except that Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and the desired compound C-1-2 (4 g, yield: 59%).

[LCMS] :795

[Synthesis Example 22] Synthesis of Compound C-1-4

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and 2- instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine. ([1,1':3',1''-terphenyl]-5-yl)-4, same procedure as in [Synthesis Example 1], except that 4,6-dichloro-1,3,5-triazine was used. This was carried out to obtain the target compound C-1-4 (3.3 g, yield: 70%).

[LCMS] :871

[Synthesis Example 23] Synthesis of Compound C-3-2

The same procedure as for [Synthesis Example 7] was performed, except that Compound S-16 obtained in Preparation Example 8 was used instead of Compound S-12 used in Synthesis Example 7, and the desired compound C-3-2 (3.7 g, yield) : 79%).

[LCMS] :948

[Synthesis Example 24] Synthesis of Compound C-3-4

Compound S-16 obtained in Preparation Example 8 was used instead of Compound S-12 used in Synthesis Example 7, and 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine instead of 2- ([1,1':3',1''-terphenyl]-5-yl)-4, same procedure as in [Synthesis Example 7], except that 4,6-dichloro-1,3,5-triazine was used. This was carried out to obtain the target compound C-3-4 (2.8 g, yield: 60%).

[LCMS] :1024

[Synthesis Example 25] Synthesis of Compound A-1-10

2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1 instead of 2,4-dichloro-6-(4-(pyridin-3-yl)phenyl) The same procedure as in [Synthesis Example 1] was performed, except that -1,3,5-triazine was used to obtain the target compound A-1-10 (3.5 g, yield: 80%).

[LCMS] :696

[Synthesis Example 26] Synthesis of Compound A-1-24

Instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine used in Synthesis Example 1, 2,4-dichloro-6-(9,9-dimethyl-9H-fluoren-2 -yl)-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] to obtain the target compound A-1-24 (2.5g, yield: 57%).

[LCMS] :735

[Synthesis Example 27] Synthesis of Compound A-2-16

The same procedure as in [Synthesis Example 1] was performed, except that Compound S-19 obtained in Preparation Example 11 was used instead of Compound S-2 used in Synthesis Example 1, and the desired compound A-2-16 (2.9 g, yield) : 67%).

[LCMS] :785

[Synthesis Example 28] Synthesis of Compound A-5-8

Compound S-10 obtained in Preparation Example 5 was used instead of Compound S-2 used in Synthesis Example 1, and 2, instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine, Except that 4-dichloro-6-phenyl-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain the target compound A-5-8 (4.9g, yield: 77%). Got.

[LCMS] :952

[Synthesis Example 29] Synthesis of Compound B-1-10

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and 2, instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine, Except that 4-dichloro-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was carried out, and the target compound B-1- 10 (3.3 g, yield: 81%).

[LCMS] :796

[Synthesis Example 30] Synthesis of Compound B-1-16

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and 2, instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine, Except that 4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was carried out to effect the target compound B-1. -16 (3.2 g, Yield: 69%) was obtained.

[LCMS] :809

[Synthesis Example 31] Synthesis of Compound B-1-24

Compound S-4 obtained in Preparation Example 2 was used instead of Compound S-2 used in Synthesis Example 1, and 2, instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine, Except that 4-dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was carried out to obtain target compound B. -1-24 (3.2 g, Yield: 69%) was obtained.

[LCMS] :835

[Synthesis Example 32] Synthesis of Compound C-1-10

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and 2, instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine, Except that 4-dichloro-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was carried out, and the target compound C-1- 10 (2.2 g, yield: 70%).

[LCMS] :796

[Synthesis Example 33] Synthesis of Compound C-1-16

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine 2,4 -Dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine, except that the same procedure as in [Synthesis Example 1] to perform the target compound C-1- 16 (2.4g, Yield: 72%).

[LCMS] :809

[Synthesis Example 34] Synthesis of Compound C-1-24

Compound S-6 obtained in Preparation Example 3 was used instead of Compound S-2 used in Synthesis Example 1, and 2, instead of 2-(biphenyl-4-yl)-4,6-dichloro-1,3,5-triazine, Except that 4-dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain the target compound C. -1-24 (2.0 g, yield: 62%) was obtained.

[LCMS] :835

[Example 1] Fabrication of green organic electroluminescent device

The compound A-1-2 synthesized in Synthesis Example 1 was subjected to a high-purity sublimation purification by a commonly 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% compound A-1-2 (30 nm)/DS-505 (30 nm)/LiF (1 nm)/Al (200 nm) were stacked to prepare an organic electroluminescent device. The structures of NPB and mCBP used at this time are as follows.

[Examples 2 to 24] 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-1-2 used as the light emitting layer material 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-1-2 used as the light emitting layer material 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 the following compound Com-1 was used instead of the compound A-1-2 used as the light emitting layer material in Example 1. The structure of the compound Com-1 used at this time is as follows.

[Evaluation Example 1]

For the green organic electroluminescent devices produced in Examples 1 to 24 and Comparative Examples 1 and 2, respectively, 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	Emitting layer	Driving voltage (V)	Luminous peak (nm)	Current efficiency (cd/A)
Example 1	A-1-2	3.2	535	40
Example 2	A-1-4	4.2	532	41
Example 3	A-1-5	4.1	530	40
Example 4	A-1-16	4.2	550	50
Example 5	A-1-20	4.1	550	53
Example 6	A-1-24	4.2	545	46
Example 7	A-3-2	4.3	545	45
Example 8	A-3-4	4.3	545	44
Example 9	A-3-5	4.3	545	43
Example 10	A-3-16	4.2	542	44
Example 11	A-3-26	4.2	550	46
Example 12	A-3-27	4.5	550	40
Example 13	A-3-28	4.1	557	45
Example 14	A-3-29	4.4	523	36
Example 15	A-4-2	4.3	525	37
Example 16	A-4-4	4.4	550	39
Example 17	B-1-2	4.5	553	39
Example 18	B-1-4	4.4	525	40
Example 19	B-3-2	4.3	535	40
Example 20	B-3-4	4.4	540	41
Example 21	C-1-2	4.4	525	39
Example 22	C-1-4	4.3	530	46
Example 23	C-3-2	4.3	534	47
Example 24	C-3-4	4.2	525	45
Comparative Example 1	Alq 3	5.6	525	13
Comparative Example 2	Com-1	4.5	550	36

As shown in Table 1 above, the green organic EL devices of Examples 1 to 24 using Compounds A-1-2 to C-3-4 according to the present invention as a light emitting layer material together with mCBP, conventional mCBP and Alq ₃ It was found that the green organic EL device of Comparative Example 1 used 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 24 were superior in current efficiency to the green organic EL devices of Comparative Example 2 using the conventional compound Com-1.

[Example 25] Fabrication of organic EL device

The compound A-1-10 synthesized in Synthesis Example 25 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% of Compound A-1-10 + 10 wt% of Ir(ppy) ₃ (300 nm)/BCP (10 nm)/Alq ₃ on the ITO transparent electrode thus prepared (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in order to prepare an organic EL device. The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , and BCP used at this time are as follows.

[Examples 26 to 34] Fabrication of organic EL device

An organic EL device was manufactured in the same manner as in Example 25, except that each of the compounds shown in Table 2 below was used instead of Compound A-1-10 used as a light emitting host material in the formation of the light emitting layer in Example 25.

[Comparative Example 3] Fabrication of organic EL device

An organic EL device was manufactured in the same manner as in Example 25, except that CBP was used instead of Compound A-1-10 used as a light emitting host material in the formation of the light emitting layer in Example 25. 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 25, except that the following compound Com-2 was used instead of Compound A-1-10 used as a light emitting host material in the formation of the light emitting layer in Example 25. The structure of the following compound Com-2 used at this time is as follows.

[Evaluation Example 2]

For the organic EL devices manufactured in Examples 25 to 34 and Comparative Examples 3 and 4, the 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 25	A-1-10	5.31	517	58
Example 26	A-1-24	5.42	517	58
Example 27	A-2-16	5.66	518	55
Example 28	A-5-8	5.7	517	55
Example 29	B-1-10	5.7	518	58
Example 30	B-1-16	5.22	518	59
Example 31	B-1-24	5.77	518	56
Example 32	C-1-10	5.32	516	59
Example 33	C-1-16	5.90	518	63
Example 34	C-1-24	5.51	518	59
Comparative Example 3	CBP	5.90	516	48
Comparative Example 4	Com-2	5.93	519	50

As shown in Table 2, the organic EL devices of Examples 25 to 34 using the compounds A-1-10 to C-1-24 according to the present invention as hosts for the light emitting layer, CBP and Com-2, which are conventional hosts, are 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.

Claims (15)

1. Compound represented by the formula (1):

   [Formula 1]

   

   (In the formula 1,

   a is an integer of 2 or 3,

   b is 0 or 1,

   However, a+b is 3,

   A plurality of A rings are the same as or different from each other, and each independently a C ₆ ~ C ₆₀ polycyclic aromatic ring,

   A plurality of X is the same or different from each other, each independently selected from the group consisting of C (R ₂ ) (R ₃ ), N (R ₄ ), O and S,

   A plurality of L ₁ are the same as or different from each other, and each independently a single bond or an arylene group of C ₆ to C ₆₀ ,

   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 is selected from the group consisting of an aryl group of C ₆ ~ C _{60 and} a heteroaryl group having 5 to 60 nuclear atoms,

   c is an integer from 0 to 4,

   The plurality of R ₁ and R ₂ 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, and C ₂ to C ₄₀ alke. Nyl 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 , is selected from the group consisting of C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, 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 , a heteroaryl group, an alkyl group of R ₁ to R ₅ , an alkenyl group, alkynyl group, 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 are each independently deuterium, halogen, cyano group, nitro Group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ Aryl group of ~C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ ~C ₄₀ , aryloxy group of C ₆ ~C ₆₀ , alkylsilyl group of C ₁ ~C ₄₀ , C ₆ Arylsilyl group of ~ C ₆₀ , alkyl boron group of C ₁ ~ C ₄₀ , aryl boron group of C ₆ ~ C ₆₀ , arylphosphine group of C ₆ ~ C ₆₀ , arylphosphine oxide group of C ₆ ~ C ₆₀ and C ₆ ~ C ₆₀ is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, where the plurality of substituents are the same or different from each other).
2. According to claim 1,

   The compound represented by Formula 1 is a compound represented by Formula 2 below:

   [Formula 2]

   

   (In the formula 2,

   The plurality of B rings are the same as or different from each other, and each independently a C ₆ to C ₄₀ monocyclic aromatic ring or a C ₆ to C ₄₀ polycyclic aromatic ring,

   X, Y ₁ to Y ₃ , L ₁ , Ar ₁ , a, b, c and R ₁ are each as defined in claim 1 ).
3. According to claim 1,

   The A ring is a naphthalene ring, anthracene ring, tetracene ring, pyrene ring, phenanthrene ring, phenalene ring, benzoanthracene ring, and benzopyrene ring benzopyrene) compound selected from the group consisting of rings.
4. According to claim 1,

   All of Y ₁ to Y ₃ are N compounds.
5. According to claim 1,

   R ₁ is a compound selected from the group consisting of hydrogen and the following substituents S1-1 to S1-27:

   

   (In the substituents S1-1 to S1-27,

   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.
6. According to claim 1,

   Ar ₁ is a substituent selected from the group consisting of the following substituents S2-1 to S2-26:

   

   (In the substituents S2-1 to S2-26,

   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.
7. 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 , a, b, c and R ₁ are each as defined in claim 1 ).
8. According to claim 1,

   A plurality of L ₁ are the same or different from each other, and each independently a single bond or a phenylene group.
9. 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,

   The plurality of B rings are the same as or different from each other, and each independently a C ₆ to C ₄₀ monocyclic aromatic ring or a C ₆ to C ₄₀ polycyclic aromatic ring,

   X, Y ₁ to Y ₃ , Ar ₁ , c and R ₁ are each as defined in claim 1,

   d is 0 or 1).
10. According to claim 1,

    The compound represented by Formula 1 is a compound represented by Formula 10 or 11 below:

    [Formula 10]

    

    [Formula 11]

    

    (In the above formulas 10 and 11,

    The plurality of B rings are the same as or different from each other, and each independently a C ₆ to C ₄₀ monocyclic aromatic ring or a C ₆ to C ₄₀ polycyclic aromatic ring,

    X, Y ₁ to Y ₃ , Ar ₁ are each as defined in claim 1,

    d is 0 or 1,

    e and f 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,

    R ₈ and R ₉ 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 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).
11. According to claim 1,

    The compound represented by Formula 1 is a compound represented by any one of the following Formulas 12 to 21:

    [Formula 12]

    

    [Formula 13]

    

    [Formula 14]

    

    [Formula 15]

    

    [Formula 16]

    

    [Formula 17]

    

    [Formula 18]

    

    [Formula 19]

    

    [Formula 20]

    

    [Formula 21]

    

    (In the formulas 12 to 21,

    X, Y ₁ to Y ₃ , Ar ₁ are each as defined in claim 1,

    d is 0 or 1,

    e and f 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,

    R ₈ and R ₉ 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 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).
12. 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 comprises an organic compound according to any one of claims 1 to 11.
13. The method of claim 12,

    The organic material layer including the compound is an organic electroluminescent device that is a light emitting layer.
14. The method of claim 13,

    The light emitting layer includes a host and a dopant,

    The host is an organic electroluminescent device comprising the compound.
15. The method of claim 13,

    The light emitting layer includes a host and a dopant,

    The dopant is an organic electroluminescent device comprising the compound.

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