KR20120116272A - Novel compounds for organic electronic material and organic electroluminescence device using the same - Google Patents

Abstract

PURPOSE: A compound for organic electronic material is provided to prevent crystallization upon manufacturing a device because of excellent electron-transport efficiency, and to improve current performance of a device because of good formation of layers. CONSTITUTION: A compound for organic electronic material is represented by chemical formula 1. An organic electroluminescence device comprises a first electrode, a second electrode, and an organic material layer of one or more layers inserted between the first electrode and the second electrode. The organic material layer comprises one or more of the compound for organic electronic material, and one or more phosphorescent dopants. The organic material layer comprises an amine-based compound(A) selected from the followings: an arylamine-based compound or a styrylarylamine-based compound; a metal selected from transition metal, lanthanum metal and d-transition metal, or a metal-containing complex compound; or a mixture thereof.

Description

Novel compounds for organic electronic material and organic electroluminescence device using the same

The present invention relates to a novel compound for organic electronic materials and an organic electroluminescent device comprising the same.

Among the display elements, an electroluminescence device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining the luminous efficiency in OLEDs is the luminous material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to 4 times. To date, iridium (III) complexes are widely known as phosphorescent materials, and for each RGB, materials such as (acac) Ir (btp) ₂ , Ir (ppy) _3, and Firpic are known. In particular, many phosphorescent materials have recently been studied in Japan and Europe.

CBP is the most widely known host material for phosphorescent emitters. To date, high-efficiency OLEDs with hole blocking layers such as BCP and BAlq have been known. In Japan, Pioneer has developed high-performance OLEDs using BAlq derivatives as hosts. I've done it.

However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, so that the material changes when undergoing a high temperature deposition process under vacuum. In the relationship of power efficiency = [(π / voltage) × current efficiency] in OLED, power efficiency is inversely proportional to voltage. Therefore, to lower the power consumption of OLED, power efficiency must be increased. In fact, OLEDs using phosphorescent materials have considerably higher current efficiency (cd / A) than OLEDs using fluorescent materials, but in the case of conventional materials such as BAlq or CBP used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). In addition, when used in OLED devices, it was not satisfactory in terms of lifetime.

On the other hand, International Patent Publication No. WO 2006/049013 mentions a compound for an organic electroluminescent material having a condensed bicyclic group as a skeleton. However, this document combines both a heterocycloalkyl or a cycloalkyl-substituted nitrogen-containing condensed bicyclic group in which the aromatic ring is fused at positions 9 and 3 of the carbazole skeleton, and a heterocycloalkyl or cycloalkyl group in which the aromatic ring is fused. No compound is disclosed.

Accordingly, an object of the present invention is to firstly provide a compound for organic electronic material having a good skeleton having an excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems. It is to provide a high efficiency and long life organic electroluminescent element employing a compound for a material as a light emitting material.

The present invention relates to a compound for an organic electronic material represented by the following formula (1) and an organic electroluminescent device comprising the same, the compound for an organic electronic material according to the present invention has better luminous efficiency and excellent life characteristics of the material than the conventional material The driving life of the device is very excellent and there is an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.

 [Formula 1]

In Formula 1,

이며;A is hydrogen or

;

이고;B is hydrogen or

ego;

Unless A and B are hydrogen at the same time;

L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C5-C30) heteroarylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C6-C30) cyclo Alkylene,

X ₁ is CH or N,

Y ₁ to Each Y ₃ is independently —O—, —S—, —CR ₁₀ R ₁₁ —, or —NR ₁₂ —,

R ₁ to R ₁₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, cycloalkyl At least one fused substituted or unsubstituted (C6-C30) aryl, a 5 to 7 membered heterocycloalkyl fused at least one substituted or unsubstituted aromatic ring, or at least one fused substituted or unsubstituted aromatic ring (C3-C30) cycloalkyl, -NR ₂₁ R ₂₂ , -SiR ₂₃ R ₂₄ R ₂₅ , -SR ₂₆ , -OR _{27 ,} (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, Substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C3) with or without nitro or hydroxy or with a fused ring with adjacent substituents 0) can be linked to alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the carbon atoms of the formed alicyclic ring and monocyclic or polycyclic aromatic ring are selected from nitrogen, oxygen and sulfur May be substituted with one or more heteroatoms,

R ₂₁ to R ₂₇ are the same as the definitions of R ₁ to R ₁₂ ,

a, d, g, i are each independently an integer of 1 to 4, when a, b, g, i is an integer of 2 or more, may be the same or different,

b, c, e, f, h are each independently an integer of 1 to 3, when b, c, e, f, h is an integer of 2 or more, may be the same or different,

The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.

Substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described herein include all linear or pulverized forms, and "cycloalkyl" is not only a monocyclic system but also substituted or unsubstituted adamantyl Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. There is this. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. "Heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Means an aryl group, 5-6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. Heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, Monocyclic heteroaryl such as tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoiso Thiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnaolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenantri Polycyclic heteroaryls such as dinyl, benzodioxyl, dibenzofuranyl, dibenzothiophenyl and their corresponding N-oxides (e.g. pyridyl N-oxides, quinolyl N-oxides), Quaternary salts; and the like.

In addition, the '(C1-C30) alkyl' group described in the present invention is preferably (C1-C20) alkyl, more preferably (C1-C10) alkyl, and the '(C6-C30) aryl' group is preferably Is (C6-C20) aryl, more preferably (C6-C12) aryl. The '(C3-C30) heteroaryl' group is preferably (C3-C20) heteroaryl, more preferably (C3-C12) heteroaryl. The '(C3-C30) cycloalkyl' group is preferably (C3-C20) cycloalkyl, more preferably (C3-C7) cycloalkyl. The '(C2-C30) alkenyl or alkynyl' group is preferably (C2-C20) alkenyl or alkynyl, more preferably (C2-C10) alkenyl or alkynyl.

In addition, in the description of "substituted or unsubstituted" described in the present invention, 'substituted' means a case where is further substituted with an unsubstituted substituent, the L ₁ and L _{2 ,} R ₁ to R ₁₂ And the substituents further substituted for R ₂₁ to R ₂₇ are deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 5 -C 30) heteroaryl, ( (C5-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, heterocycloalkyl, (C1-C30) alkylsilyl, (C6-C30) arylsilyl, (C1-C30) alkyl (C6-C30) arylsilyl, (C2-C30) alkenyl, (C6-C30) alkynyl, cyano, carbazolyl, (C1-C30) alkylamino, (C6-C30) arylamino, (C1-C30 ) Alkyl (C6-C30) arylamino, (C6-C30) arylboronyl, (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30 ) At least one selected from the group consisting of ar (C 1 -C 30) alkyl, (C 1 -C 30) alkyl (C 6 -C 30) aryl, carbonyl, carboxyl, nitro or hydroxy.

는 하기 구조에서 선택되는 것이 바람직하다. More specifically

Is preferably selected from the following structures.

Typical compounds for organic electronic materials according to the present invention include the following compounds.

The compound for an organic electronic material according to the present invention can be prepared as shown in the following scheme.

[Reaction Scheme 1]

Scheme 2

[A, B, R ₁ to R ₉ , Y ₁ in Schemes 1 to 2 To Y ₃ , X ₁ , L _{1 ,} L ₂ , a to i are the same as defined in Formula 1, and X is halogen.]

In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention is an organic electroluminescent device having a first electrode, a second electrode and at least one organic material layer interposed between the first electrode and the second electrode. In the device, the organic material layer includes at least one compound represented by Chemical Formula 1. The organic material layer may include a light emitting layer, and the compound of Formula 1 may be used as a host material in the light emitting layer.

In addition, a phosphorescent dopant for an organic electroluminescent device used with a host according to the present invention typically includes a compound represented by the following Chemical Formula 2.

[Formula 2]

M ^One L ¹⁰¹ L ¹⁰² L ¹⁰³

[In the formula (2)

Wherein M ¹ is selected from the group consisting of Ir, Pt, Pd, Os,

The ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ are independently selected from the following structures.

R ₂₀₁ to R ₂₀₃ independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;

R ₂₀₄ to R ₂₁₉ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF ₅ , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;

R ₂₂₀ to R ₂₂₃ are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;

R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

R ₂₂₆ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;

R ₂₂₇ to R ₂₂₉ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;

,

또는

이며, R₂₃₁ 내지 R₂₄₂는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된(C6-C30)아릴, 시아노, 치환 또는 비치환된(C5-C30)시클로알킬이거나, 인접한 치환체와 알킬렌 또는 알케닐렌으로 연결되어 스피로 고리 또는 융합고리를 형성할 수 있거나, R₂₀₇ 또는 R₂₀₈과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.Q is

,

or

R ₂₃₁ to R ₂₄₂ are each independently of the other hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or with R ₂₀₇ or R ₂₀₈ and alkylene or alkenylene Can be linked to form a saturated or unsaturated fused ring.

Specifically, it is preferable to use the following compounds as the dopant compound of Chemical Formula 2.

The organic electroluminescent device of the present invention includes a compound of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds.

In addition, in the organic electroluminescent device of the present invention, the organic material layer is selected from the group consisting of Group 1, Group 2, Group 4, Period 5 transition metals, Lanthanide series metals and organic metals of d-transition elements in addition to the compound of Formula 1 One or more metal or complex compounds may be further included. Furthermore, the organic material layer may further include a light emitting layer and a charge generating layer.

In addition, the organic material layer may include one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the compound for organic electronic materials to form an organic light emitting device that emits white light.

In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as "surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferred examples of the chalcogenide include SiO _X (1 ≦ _X ≦ ₂ ), AlO _X (1 ≦ _X ≦ 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , and fluoride. Rare earth metals and the like, and preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.

The compound for an organic electronic material according to the present invention has an advantage of manufacturing an OLED device having excellent luminous efficiency and excellent lifespan characteristics of the device, and having excellent driving life of the device.

Hereinafter, a compound for an organic electronic material according to the present invention, a method for preparing the same, and a light emitting property of a device will be described with reference to a representative compound of the present invention for a detailed understanding of the present invention.

Preparation Example 1 Preparation of Compound 3

compound 1-1 Manufacturing

9-phenyl-9H-carbazolel-2-ylboronic acid (14 g, 48.76 mmol), 3-bromo-9H-carbazole (10 g, 40.63 mmol), K ₂ CO ₃ (13.5 g, 97.52 mmol) and Pd (PPh ₃ ) ₄ (2.35 g, 2.03 mmol) was added to 200 mL of toluene, 50 mL of EtOH, and 50 mL of purified water, followed by stirring at 95 ° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and left to stand to remove the aqueous layer. The oil layer was concentrated, triturated with MC, and filtered to obtain compound 1-1 (12 g, 72%).

compound 1-2 Manufacturing

2,4-dichloroquinazolin (30 g, 151 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid (15.6 g, 75.3 mmol), Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and Na ₂ CO ₃ (16 g, 150 mmol) was dissolved in toluene (300 ml) and distilled water (75 ml) and stirred at 90 ° C. for 2 hours. The organic layer was distilled under reduced pressure and triturated with MeOH. The obtained solid was dissolved in MC, silica filtered, and triturated with MC and hexane to obtain compound 1-2 (9.3 g, 51.4%).

compound 3 Manufacturing

Compound 1-1 (5.3 g, 14.7 mmol) and Compound 1-2 (6.4 g, 15.8 mmol) were suspended in 80 mL of DMF, and then 60% NaH (948 mg, 22 mmol) was added at room temperature, followed by stirring for 12 hours. . Purified water (1L) and filtered under reduced pressure. The obtained solid was triturated with MeOH / EA, dissolved in MC, silica filtered, and triturated with MC / n-Hexane to obtain Compound 3 (1.9 g, 16.8%).

MS / FAB found 778, calculated 777.91

Example 1 Fabrication of an OLED Device Using a Compound for Organic Electronic Materials According to the Present Invention

An OLED device having a structure using the light emitting material of the present invention is produced. First, the transparent electrode ITO thin film (15Ω / □) obtained from OLED glass (manufactured by Samsung-Corning) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol, and distilled water sequentially, and then stored in isopropanol. use. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N1- (naphthalen-2-yl) -N4, N4-bis (4- (naphthalen-2-yl (phenyl) amino ) Phenyl) -N1-phenylbenzene-1,4-diamine was added and evacuated until the vacuum in the chamber reached 10E-6 torr, followed by the application of a current to the cell to evaporate a 60 nm thick hole injection layer on the ITO substrate. Deposit. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl was added to another cell in the vacuum deposition equipment, and a current was applied to the cell. It is applied and evaporated to deposit a 20 nm thick hole transport layer on the hole injection layer. After the hole injection layer and the hole transport layer are formed, a light emitting layer is deposited thereon as follows. Compounds of the present invention as a host in one cell in a vacuum deposition apparatus, each dopant in another cell, and then evaporated at different rates to do the two materials at a rate of 4 to 20% by weight of 30 nm on the hole transport layer. The light emitting layer is deposited. Then one cell as the electron transport layer on the light emitting layer, followed by 9,10-di (1-naphthyl) -2- (4-phenyl-1-phenyl-1H-benzo [d] in one cell as the electron transport layer on the light emitting layer. Imidazole) anthracene was added, and another cell was charged with lithium quinolate, and the two materials were evaporated at different rates to be doped at 30 to 70% by weight to deposit an electron transport layer of 30 nm. Subsequently, lithium quinolate was deposited to a thickness of 1 to 2 nm as an electron injection layer, and then an Al cathode was deposited to a thickness of 150 nm using other vacuum deposition equipment to produce OLED devices with good characteristics in terms of voltage, efficiency and lifetime. It is expected to have.

Claims (10)

A compound for an organic electronic material represented by Formula 1 below:
[Formula 1]

In Chemical Formula 1,
A is hydrogen or

;
B is hydrogen or

ego;
Unless A and B are hydrogen at the same time;
L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C5-C30) heteroarylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C6-C30) cyclo Alkylene,
X ₁ is CH or N,
Y ₁ To Each Y ₃ is independently —O—, —S—, —CR ₁₀ R ₁₁ —, or —NR ₁₂ —,
R ₁ to R ₁₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, cycloalkyl At least one fused substituted or unsubstituted (C6-C30) aryl, a 5 to 7 membered heterocycloalkyl fused at least one substituted or unsubstituted aromatic ring, or at least one fused substituted or unsubstituted aromatic ring (C3-C30) cycloalkyl, -NR ₂₁ R ₂₂ , -SiR ₂₃ R ₂₄ R ₂₅ , -SR ₂₆ , -OR _{27 ,} (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, Substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C3) with or without nitro or hydroxy or with a fused ring with adjacent substituents 0) can be linked to alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the carbon atoms of the formed alicyclic ring and monocyclic or polycyclic aromatic ring are selected from nitrogen, oxygen and sulfur May be substituted with one or more heteroatoms,
R ₂₁ to R ₂₇ are the same as the definitions of R ₁ to R ₁₂ ,
a, d, g, i are each independently an integer of 1 to 4, when a, b, g, i is an integer of 2 or more, may be the same or different,
b, c, e, f, h are each independently an integer of 1 to 3, when b, c, e, f, h is an integer of 2 or more, may be the same or different,
The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.
The method of claim 1,
Substituents substituted for L ₁ and L _2, R ₁ to R _12, and R ₂₁ to R ₂₇ are deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) Aryl, (C5-C30) heteroaryl, (C5-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, heterocycloalkyl, (C1-C30) alkylsilyl, (C6- C30) arylsilyl, (C1-C30) alkyl (C6-C30) arylsilyl, (C2-C30) alkenyl, (C6-C30) alkynyl, cyano, carbazolyl, (C1-C30) alkylamino, ( C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C6-C30) arylboronyl, (C1-C30) alkylboronyl, (C1-C30) alkyl (C6- C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carbonyl, carboxyl, nitro or hydroxy selected from the group consisting of The compound for organic electronic materials.
The method of claim 1,
X ₁ is CH or N,
L ₁ and L ₂ are each independently a single bond, phenylene, naphthylene, biphenylene, terphenylene, anthylene, andenylene, fluorenylene, phenanthryl, triphenylenylene, pyrenylene, pehen Reyleneylene, Chrysenylene, Naphthacelene, Fluoranthenyl, Purylene, Thiophenylene, Pyrrylene, Imidazolene, Pyrazolylene, Thiazolylene, Tiadiazolylene, Isothiazolylene, Isoxa Zoleylene, oxazolylene, oxadiazolylene, triazineylene, tetrazinylene, triazolylene, tetrazoylene, furazanthylene, pyridylene, pyrazinylene, pyrimidinylene, pyridazineylene, benzofuranylene, Benzothiophenylene, isobenzofuranylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzooxazolylene, isoindoleylene, indolylene, indazolylene, benzo Thiadiazolylene, quinolylene, isoquinolylene, cinnolinylene, quinazolinylene And quinoxalinylene, carbazolylene, phenanthridinylene, benzodioxoleylene, dibenzofuranylene and dibenzothiophenylene.
The method of claim 1,
remind

The

Compound for an organic electronic material selected from the group consisting of.
The method of claim 1,
A compound for organic electronic materials selected from the following compounds.

An organic electroluminescent device comprising the compound for organic electronic material of any one of claims 1 to 5.
The method according to claim 6,
The organic electroluminescent device comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one of the compounds for organic electronic materials and at least one phosphorescent dopant represented by Formula 2 below. Organic electroluminescent element:
(2)
M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³
In Formula 2,
M ¹ is selected from the group consisting of Ir, Pt, Pd, Os;
The ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ are independently selected from the following structures;

R ₂₀₁ to R ₂₀₃ independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R ₂₀₄ to R ₂₁₉ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF ₅ , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R ₂₂₀ to R ₂₂₃ are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R ₂₂₄ and R ₂₂₅ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R ₂₂₆ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R ₂₂₇ to R ₂₂₉ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q is

,

or

R ₂₃₁ to R ₂₄₂ are each independently of the other hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or with R ₂₀₇ or R ₂₀₈ and alkylene or alkenylene Can be linked to form a saturated or unsaturated fused ring.
The method of claim 7, wherein
The phosphorescent dopant is selected from the following compounds.

The method of claim 7, wherein
At least one amine compound (A) wherein the organic material layer is selected from the group consisting of an arylamine compound or a styrylarylamine compound; Complex compounds (B) comprising at least one metal or metal selected from the group consisting of Group 1, Group 2, 4 and 5 cycle transition metals, lanthanide series metals and organic metals of d-transition elements; Or an organic electroluminescent device comprising a mixture thereof.
The method of claim 7, wherein
The organic light emitting device of claim 1, wherein the organic material layer further comprises at least one organic light emitting layer emitting blue, red, or green light.