KR20120122812A - Novel organic electroluminescence compounds and organic electroluminescence device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescence device is provided to have excellent luminous efficiency and life time and to manufacture an organic light emitting diode device with excellent device life time. CONSTITUTION: An organic electroluminescence device is represented by chemical formula 1. In chemical formula 1, A1-A5 is respectively R, N or a functional group in chemical formula 1-a. Y is -O-, -S-, -CR7R8- or -NR9-, each of L1-L2 is a single bond, a substituted or unsubstituted (C3-30) heteroarylene, a substituted or unsubstituted (C6-30) arylene or a substituted or unsubstituted (C3-30) cycloalkylene, each of R1-R4 is hydrogen, deuterium, halogen, substituted or unsubstituted(C61-30)alkyl, substituted or unsubstituted(C6-30)aryl, substituted or unsubstituted(C3-30)heteroaryl, substituted or unsubstituted(C3-30)cycloalkyl, substituted or unsubstituted 5-7membered heterocycloalkyl, substituted or unsubstituted(C6-30)[ar](C1-30)alkyl, -NR11R12, -SiR13R14R15, -SR16, -OR17, cyano, nitro or hydroxy.

Description

Novel organic electroluminescence compounds and organic electroluminescence device using the same

The present invention relates to a novel organic light emitting compound 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 OLED, power efficiency = [(π / voltage) × current efficiency], so power efficiency is inversely proportional to voltage. Therefore, to lower the power consumption of the 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. WO03 / 078541 mentions a compound for an organic electroluminescent material having a carbazole group as a skeleton. However, this document does not disclose a compound in which a heterocycloalkyl or cycloalkyl group in which an aromatic ring is fused at position 3 of a carbazole skeleton is substituted, and a heteroaryl in which a carbazole group is substituted at position 9 is directly or indirectly connected. not.

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

The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has better light emission efficiency and excellent life characteristics of the material than the existing material, the driving life of the device This is not only very good, but also has an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.

[Formula 1]

[In Formula 1,

이고, 단, A₁ 내지 A₅ 중 적어도 하나는

이며;A ₁ to A ₅ are each independently CR, N or

Provided that at least one of A ₁ to A ₅ is

;

Y is -O-, -S-, -CR ₇ R ₈ -or -NR _9- ;

L ₁ to L ₂ are each independently a single bond, substituted or unsubstituted (C3-C30) heteroarylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) cyclo Alkylene;

R is hydrogen, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30) heteroaryl;

R ₁ to R ₄ 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, -NR ₁₁ R ₁₂ , -SiR ₁₃ R ₁₄ R ₁₅ , -SR ₁₆ , -OR _{17 ,} cyano, nitro or hydroxy;

R ₅ to R ₉ and R ₁₁ to R ₁₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or a substitution with or without a fused ring with adjacent substituents, or May be linked to an unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the alicyclic ring and Carbon atoms of monocyclic or polycyclic aromatic rings may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;

a, b, e and f are each independently integers of 1 to 4, and may be the same or different when a, b, e and f are integers of 2 or more;

c and d are each independently an integer of 1 to 3, and may be the same or different when c and d are an integer of 2 or more;

Wherein said 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. In addition, 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;

Further, 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 preferred. Preferably (C6-C20) aryl. The '(C3-C30) heteroaryl' group is preferably (C3-C20) 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 , L ₂ , R, R ₁ to R ₄ , R ₅ to Substituents further substituted by R ₉ and R ₁₁ to R ₁₇ include deuterium, halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted by halogen, (C6-C30) aryl, (C3-C30) heteroaryl (C5-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di ( C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, Di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkyl Boronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro Or hydroxy It means one or more selected from the group consisting of.

More specifically, L ₁ and L ₂ are each independently a single bond, (C3-C30) heteroarylene or (C6-C30) arylene;

R is hydrogen, (C6-C30) aryl or (C3-C30) heteroaryl;

R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, N-carbazolyl, -NR ₁₁ R ₁₂ , or- SiR ₁₃ R ₁₄ R ₁₅ ;

R ₅ to R ₉ are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl;

R ₁₁ to R ₁₅ are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;

The arylene and heteroarylene of L ₁ and L ₂ , the aryl and heteroaryl of R, alkyl, aryl and heteroaryl of R ₁ to R ₁₅ are each substituted or unsubstituted (C1-C30) deuterium, halogen, halogen ) Alkyl, (C6-C30) aryl, (C6-C30) aryl substituted with (C1-C30) alkyl, (C3-C30) heteroaryl substituted or unsubstituted (C6-C30) aryl, N-carbazole , (C3-C30) cycloalkyl, (C6-C30) aryl substituted with N-carbazole and (C6-C30) ar (C1-C30) alkyl may be further substituted with one or more substituents selected from the group consisting of .

는 하기 구조로부터 선택되는 것이 바람직하다.Specifically above

Is preferably selected from the following structures.

이며; R₅, R₆, R^x 및 R^y은 서로 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴, N-카바졸릴, -NR₁₁R₁₂, 또는 -SiR₁₃R₁₄R₁₅이며; R₁₁ 내지 R₁₅는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이고; L₁, L₂ 및 L₃는 서로 독립적으로 단일결합, (C3-C30)헤테로아릴렌 또는 (C6-C30)아릴렌이고; 상기 L₁, L₂ 및 L₃의 아릴렌 및 헤테로아릴렌, R', R'', R''', R'''' 및 R'''''의 아릴 및 헤테로아릴, R₅, R₆, R^x, R^y 및 R₁₁ 내지 R₁₅의 알킬, 아릴 및 헤테로아릴은 각각 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알킬이 치환된 (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, N-카바졸, (C3-C30)시클로알킬, N-카바졸이 치환된 (C6-C30)아릴 및 (C6-C30)아르(C1-C30)알킬로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.]
[Wherein R ', R'',R''', R '''' and R '''''are independently of each other hydrogen, (C6-C30) aryl, (C3-C30) heteroaryl or

; R ₅ , R ₆ , R ^x and R ^y are independently of each other hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, N-carbazolyl, -NR ₁₁ R ₁₂ , or -SiR ₁₃ R ₁₄ R ₁₅ ; R ₁₁ to R ₁₅ are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl; L ₁ , L ₂ and L ₃ are independently of each other a single bond, (C3-C30) heteroarylene or (C6-C30) arylene; The arylene and heteroarylene of L ₁ , L ₂ and L ₃ , R ', R'',R''', R '''' and R '''''aryl and heteroaryl, R ₅ , Alkyl, aryl and heteroaryl of R ₆ , R ^x , R ^y and R ₁₁ to R ₁₅ are each (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 1) unsubstituted or substituted with deuterium, halogen, halogen (C6-C30) aryl substituted with alkyl, (C6-C30) heteroaryl substituted or unsubstituted with (C3-C30) heteroaryl, N-carbazole, (C3-C30) cycloalkyl, N-carba The sol may be further substituted with one or more substituents selected from the group consisting of substituted (C6-C30) aryl and (C6-C30) ar (C1-C30) alkyl.]

는 하기 구조로부터 선택되는 것이 바람직하다. More specifically

Is preferably selected from the following structures.

Examples of the organic light emitting compound according to the present invention include the following compounds.

The organic light emitting compound according to the present invention can be prepared as shown in the following scheme.

[Reaction Scheme 1]

[In Scheme 1, A ₁ to A ₅ , R ₁ to R ₄ , Y, L ₁ , a, b, c, and d are the same as defined in Formula 1, and X is a halogen.]

In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention 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 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 and 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 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 organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device.

Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same, and light emitting characteristics of the 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 22

compound 1-1 Manufacturing

9H-carbazole 50g (299.0mmol), 1,3-dibromobenzene 282g (1196.1mmol), CuI 57g (299.0mmol), K ₃ PO ₄ 190g (897.1mmol) and 1.5L toluene was added and heated to 80 ℃ 40 ml (598.1 mmol) of ethylenediamine was added thereto, followed by stirring under reflux for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, extracted with EA, washed with saturated aqueous NaHCO ₃ solution, dried over anhydrous MgSO ₄ , distilled under reduced pressure, and obtained by column (MC: Hex) to obtain compound 1-1 40g (42%).

compound 1-2 Manufacturing

40 g (125.7 mmol) of Compound 1-1 were dissolved in THF, and 65 ml (163.4 mmol, 2.5 M in hexane) of n-buLi were slowly added at -78 ° C. After one hour, 21 ml (188.6 mmol) of trimethylborate was added and stirred at room temperature for 12 hours. After completion of the reaction, the mixture was washed with distilled water, extracted with EA, the organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and recrystallized with EA, hexane, and MC to obtain Compound 1-2 33g (92%).

compound 1-3 Manufacturing

Compound 1-2 26g (91.6mmol), 2,4-dichloropyrimidine 12g (83.3mmol), Pd (PPh ₃ ) ₄ 2.9g (2.50mmol), 2M K ₂ CO ₃ 140ml and toluene were added at 80 ° C Stir for 2 hours. When the stirring was completed, cooled to room temperature, washed with distilled water and extracted with EA. The organic layer was dried over anhydrous MgSO ₄ and distilled under reduced pressure, followed by column separation (MC: HEX) to obtain compound 1-3 13g (44%).

compound 1-4 Manufacturing

38 g (131.0 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid, 26 g (109.1 mmol) of 3-bromo-9H-carbazole, 6.3 g (5.46 mmol) of Pd (PPh ₃ ) ₄ , 2M K ₂ 130 ml of CO ₃ and toluene were added and stirred at 130 ° C. for 10 hours. After stirring was completed, the mixture was cooled to room temperature, distilled water was added, and extracted with EA. The sulfur organic layer was dried over anhydrous MgSO _4, and distilled under reduced pressure, followed by column separation (MC: HEX), to obtain 35 g (79%) of Compound 1-4 .

compound 22 Manufacturing

NaH (734 mg) was mixed with DMF (20 ml) and then stirred. 5 g (12.2 mmol) of Compound 1-4 were dissolved in DMF (20 ml), and then slowly added to the NaH-DMF mixture. After 1 hour, 5.2 g (14.7 mmol) of Compound 1-3 was dissolved in DMF (20 ml). It was added slowly to the mixture. After stirring at room temperature for 12 hours, distilled water was slowly added, and the solid formed while quenching was filtered. Column (MC: Hex) was separated and obtained as compound 22 7g (79%).

MS / FAB found 727.85, calculated 727.27

Example 1 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention

An OLED device having a structure using the light emitting material of the present invention was produced. First, a transparent electrode ITO thin film (15? It was used after. Next, after mounting the ITO substrate to the substrate holder of the vacuum deposition equipment, N1- (naphthalen-2yl) -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 10 ^-6 torr. Then, the cell was evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl was added to another cell in the vacuum deposition apparatus, and the cell was applied with an electric current to evaporate. A 20 nm thick hole transport layer was deposited on the hole injection layer. After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound 30 according to the present invention as a host in one cell in the vacuum deposition equipment, Compound D-34 as a dopant in each cell, and then the two materials were evaporated at different rates to be doped at 4 to 20% by weight. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. Subsequently, tris (8-hydroxyquinoline) -aluminum (III) was deposited on one cell as an electron transport layer to a thickness of 20 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 another vacuum deposition equipment to manufacture an OLED device.

Each compound was vacuum sublimated and purified under 10 ^-6 torr to be used as an OLED light emitting material.

As a result, a current of 2.74 mA / cm ² flowed at 3.9 V, and green light emission of 1020 cd / m ² was confirmed.

Example 2 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

An OLED device was manufactured in the same manner as in Example 1, except that Compound 22 was used as a light emitting material and Compound D-5 was used as a dopant.

As a result, a current of 2.38 mA / cm ² flowed at 3.8 V, and green light emission of 1050 cd / m ² was confirmed.

Example 3 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

An OLED device was manufactured in the same manner as in Example 1, except that Compound 69 was used as a light emitting material and Compound D-57 was used as a dopant.

As a result, a current of 2.36 mA / cm ² flowed at 4.0 V, and green light emission of 1030 cd / m ² was confirmed.

Example 4 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

An OLED device was manufactured in the same manner as in Example 1, except that Compound 70 was used as a light emitting material and Compound D-5 was used as a dopant.

As a result, a current of 2.59 mA / cm ² flowed at 3.7 V, and green light emission of 1070 cd / m ² was confirmed.

[Comparative Example 1] Luminescence characteristics of OLED device using conventional light emitting material

4,4'-bis (carbazol-9-yl) biphenyl (CBP), dopantro D-5, is used instead of the compound of the present invention as a host material in one cell in the vacuum deposition equipment, and bis ( An OLED device was manufactured in the same manner as in Example 1, except that 2-methyl-8-quinolinate) (p-phenylphenolrato) aluminum (III) (Balq) was used.

As a result, a current of 2.86 mA / cm ² flowed at 4.9 V, and green light emission of 1000 cd / m ² was confirmed.

It was confirmed that the light emission characteristics of the organic light emitting compounds developed in the present invention showed superior characteristics compared to the conventional material. In the present invention, the device using the organic light emitting compound as a green light emitting host material is excellent in the light emission characteristics. In particular, since the driving voltage is lowered, power consumption can be improved.

Claims (10)

An organic light emitting compound represented by Formula 1 below.
[Formula 1]

[In the above formula (1)
A ₁ to A ₅ are each independently CR, N or

Provided that at least one of A ₁ to A ₅ is

;
Y is -O-, -S-, -CR ₇ R ₈ -or -NR _9- ;
L ₁ to L ₂ are each independently a single bond, substituted or unsubstituted (C3-C30) heteroarylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) cyclo Alkylene;
R is hydrogen, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30) heteroaryl;
R ₁ to R ₄ 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, -NR ₁₁ R ₁₂ , -SiR ₁₃ R ₁₄ R ₁₅ , -SR ₁₆ , -OR _{17 ,} cyano, nitro or hydroxy;
R ₅ to R ₉ and R ₁₁ to R ₁₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or a substitution with or without a fused ring with adjacent substituents, or May be linked to an unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the alicyclic ring and Carbon atoms of monocyclic or polycyclic aromatic rings may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a, b, e and f are each independently integers of 1 to 4, and may be the same or different when a, b, e and f are integers of 2 or more;
c and d are each independently an integer of 1 to 3, and may be the same or different when c and d are an integer of 2 or more;
Wherein said heterocycloalkyl and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P. The method of claim 1,
Substituents further substituted with L ₁ , L ₂ , R, R ₁ to R ₄ , R ₅ to R _9, and R ₁₁ to R ₁₇ are deuterium, halogen, (C1-C30) alkyl, and halogen-substituted (C1- C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, (C6-C30) aryl substituted (C5-C30) heteroaryl, (C3-C30) cycloalkyl, heterocycloalkyl, tri ( C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30 ) Alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, Di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl , (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro or hydroxy one or more selected from the group consisting of an organic light emitting compound. The method of claim 1,
L ₁ and L ₂ are each independently a single bond, (C3-C30) heteroarylene or (C6-C30) arylene;
R is hydrogen, (C6-C30) aryl or (C3-C30) heteroaryl;
R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, N-carbazolyl, -NR ₁₁ R ₁₂ , or- SiR ₁₃ R ₁₄ R ₁₅ ;
R ₅ to R ₉ are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl;
R ₁₁ to R ₁₅ are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;
The arylene and heteroarylene of L ₁ and L ₂ , the aryl and heteroaryl of R, the alkyl, aryl and heteroaryl of R ₁ to R ₉ are each substituted or unsubstituted (C1-C30) deuterium, halogen, halogen ) Alkyl, (C6-C30) aryl, (C6-C30) aryl substituted with (C1-C30) alkyl, (C3-C30) heteroaryl substituted or unsubstituted (C6-C30) aryl, N-carbazole , (C3-C30) cycloalkyl, (C6-C30) aryl substituted with N-carbazole and (C6-C30) ar (C1-C30) alkyl which may be further substituted with one or more substituents selected from the group consisting of It is an organic light emitting compound. The method of claim 1,
remind

Is an organic light emitting compound selected from the following structures.

[Wherein R ', R'',R''', R '''' and R '''''are independently of each other hydrogen, (C6-C30) aryl, (C3-C30) heteroaryl or

; R ₅ , R ₆ , R ^x and R ^y are independently of each other hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, N-carbazolyl, -NR ₁₁ R ₁₂ , or -SiR ₁₃ R ₁₄ R ₁₅ ; R ₁₁ to R ₁₅ are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl; L ₁ , L ₂ and L ₃ are independently of each other a single bond, (C3-C30) heteroarylene or (C6-C30) arylene; The arylene and heteroarylene of L ₁ , L ₂ and L ₃ , R ', R'',R''', R '''' and R '''''aryl and heteroaryl, R ₅ , Alkyl, aryl and heteroaryl of R ₆ , R ^x , R ^y and R ₁₁ to R ₁₅ are each (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 1) unsubstituted or substituted with deuterium, halogen, halogen (C6-C30) aryl substituted with alkyl, (C6-C30) heteroaryl substituted or unsubstituted with (C3-C30) heteroaryl, N-carbazole, (C3-C30) cycloalkyl, N-carba The sol may be further substituted with one or more substituents selected from the group consisting of substituted (C6-C30) aryl and (C6-C30) ar (C1-C30) alkyl.] The method of claim 4, wherein
remind

Is an organic light emitting compound selected from the following structures.

The method of claim 1,
An organic light emitting compound selected from the following compounds.

An organic electroluminescent device comprising the organic light emitting compound of any one of claims 1 to 6. 8. The method of claim 7,
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 organic light emitting compounds and at least one of phosphorescent dopants represented by Formula 2 below. Light emitting element.
(2)
M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³
[In Formula 2,
Wherein M ¹ is selected from the group consisting of Ir, Pt, Pd and 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 To form a saturated or unsaturated fused ring.] The method of claim 8,
The phosphorescent dopant is selected from the following compounds.

The method of claim 8,
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.