KR20120030009A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescent compound is provided to have excellent luminous efficiency and life time properties, and to induce the rise of power efficiency thereby manufacturing an OLED of which power consumption is improved. CONSTITUTION: An organic electroluminescent compound is in chemical formula 1. In chemical formula 1, A is a monocyclic or polycyclic aromatic ring, X1 and X2 is independently N or CR', L1 is a single bond, substituted or non-substituted (C6-30) arylene, substituted or non-substituted (C2-30) heteroarylene, or substituted or non-substituted (C3-30) cycloalkylene, and Ar1 is hydrogen, deuterium, halogen, substituted or non-substituted (C1-30) alkyl, substituted or non-substituted (C6-30) aryl, or substituted or non-substituted (C2-30) heteroaryl.

Description

Novel organic electroluminescent compounds and organic electroluminescent 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. WO 2006/049013 mentions a compound for an organic electroluminescent material having a condensed bicyclic group as a skeleton. However, the document does not specifically disclose a compound having both a heterocycloalkyl fused with an aromatic ring or a carbazole skeleton substituted with a cycloalkyl and a nitrogen-containing condensed bicyclic group.

International Patent Publication No. WO 2006/049013 (2006.05.11.)

 Appl. Phys. Lett. 51, 913, 1987

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,

Ring A is a monocyclic or polycyclic aromatic ring;

X ₁ and X ₂ are independently of each other N or CR ′;

L ₁ is a single bond, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene;

Ar ₁ is hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C2-C30) heteroaryl;

Z are each independently selected from the following structures;

Provided that when A ring is a monocyclic aromatic ring, Z is selected from the following structures;

Y is —O—, —S—, —C (R ₁₁ R ₁₂ ) —, —Si (R ₁₃ R ₁₄ ) — or —N (R ₁₅ ) —;

R ₁ to R ₉ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-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, (C3 Substituted or unsubstituted (C6-C30) aryl wherein one or more cycloalkyl is fused, 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic, wherein one or more substituted or unsubstituted aromatic rings are fused. One or more fused (C3-C30) cycloalkyl, -NR ₁₆ R ₁₇ , -SiR ₁₈ R ₁₉ R ₂₀ , -SR ₂₁ , -OR _22, cyano, nitro or hydroxy, or R ₁ to R ₉ each represents a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C3) with or without adjacent substituents and fused rings 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 'and R ₁₁ to R ₂₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2- C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl or substituted or unsubstituted with or without fused ring with adjacent substituents ( C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene may be linked to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the alicyclic ring and monocyclic or polycyclic formed above The carbon atoms of the aromatic ring may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;

a, c, e and i are each independently integers of 1 to 4, and when a, c, e and i are integers of 2 or more, each of R ₁ , R ₃ , R ₅ and R ₉ may be the same or different; ;

b, d, g are each independently an integer of 1 to 3, and when b, d, g is an integer of 2 or more, each of R ₂ , R ₄ and R ₇ may be the same or different;

f is an integer from 1 to 6, and when f is an integer of 2 or more, each R ₆ may be the same or different;

h is an integer from 1 to 5, and when h is an integer of 2 or more, each R ₈ may be the same or different;

Wherein said heteroaromatic ring, heteroarylene, 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. Including but not limited to. The naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and phenanthryl is 1-phenanthryl, 2-phenanthryl , 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthasenyl includes 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, pyrenyl is 1-pyrenyl, 2-pyrene One, 4-pyrenyl, biphenyl includes 2-biphenyl, 3-biphenyl, 4-biphenyl, terphenyl is p-terphenyl-4-yl, p-terphenyl-3- One, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, and fluorenyl is 1-fluorenyl , 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. The "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. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked 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, fura Monocyclic heteroaryl such as residue, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiofeyl, isobenzofuranyl, benzoimidazolyl, Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinolinyl, quinazolinyl, quinoxalinyl , Polycyclic heteroaryls such as carbazolyl, phenantridinyl, benzodioxolyl, acridinyl, phenanthrolinyl, phenazinyl, phenthiazininyl, phenoxazinyl, and their corresponding N-oxides (e.g., Pyridyl N-oxide, quinolyl N-oxide), Of the like, but a quaternary salt, and the like. The pyrrolyl comprises 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyridyl includes 2-pyridyl, 3-pyridyl, 4-pyridyl, and indolyl is 1-indolyl , 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, isoindoleyl includes 1-isoindoleyl, 2-isoindoleyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolinyl, 7-isoindolinyl, furyl includes 2-furyl, 3-furyl, benzofuranyl is 2 -Benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, isobenzofuranyl is 1-isobenzofuranyl, 3 Isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, and quinolyl is 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, wherein isoquinolyl includes 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl groups, quinoxalinyl includes 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl Carbazolyl includes 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, and phenantridinyl is 1-phenanthridinyl, 2-phenanthridinyl, 3 Phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, and acridinyl is 1- Acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, phenanthrolinyl is 1,7-phenanthrolin-2-yl, 1,7 -Phenanthrolin-3-yl, 1,7-phenanthrolin-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenan Troolin-8-day, 1,7-phenanthroline-9-day, 1,7-phenanthroline-10-day, 1,8-phenanthroline-2-yl, 1,8-phenanthroline 3-yl, 1,8-phenanthrolin-4-yl, 1,8-phenan Rolin-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline- 10-day, 1,9-phenanthrolin-2-yl, 1,9-phenanthrolin-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5- Day, 1,9-phenanthroline-6-day, 1,9-phenanthroline-7-day, 1,9-phenanthroline-8-day, 1,9-phenanthroline-10-day, 1,10-phenanthrolin-2-yl, 1,10-phenanthrolin-3-yl, 1,10-phenanthrolin-4-yl, 1,10-phenanthroline-5-yl, 2, 9-phenanthrolin-1-yl, 2,9-phenanthrolin-3-yl, 2,9-phenanthrolin-4-yl, 2,9-phenanthroline-5-yl, 2,9- Phenanthroline-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthrol Lin-1-yl, 2,8-phenanthrolin-3-yl, 2,8-phenanthrolin-4-yl, 2,8-phenanthroline-5-yl, 2,8-phenanthroline- 6-day, 2,8-phenanthroline-7-day, 2,8-phenanthroline-9-day, 2,8-phenanthroline-10-day, 2,7-phenanthroline-1- 1,2,7-phenanthrolin-3-yl, 2,7-phenanthrolin-4-yl, 2,7-phenanthroline-5-yl, 2,7- Nanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, phenazinyl 1-phenazinyl, 2-phenazinyl, phenoxyazinyl, including 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenoxiyl Azinyl, phenoxazinyl includes 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, and oxazolyl is 2-oxazolyl , 4-oxazolyl, 5-oxazolyl, oxadiazoles include 2-oxazolyl, 5-oxadiazolyl, furazanyl includes 3-furazanyl, and dibenzofuranyl is 1- Dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, and dibenzothiophenyl includes 1-dibenzothiophenyl, 2-dibenzothiophenyl , 3-dibenzobenzothiophenyl, 4-diobenzothiophenyl Include.

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 '(C2-C30) heteroaryl' group is preferably (C2-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 , Ar ₁ , R ₁ to R ₉ , R 'and R ₁₁ To substituents further substituted for R ₂₂ independently of each other, substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl substituted or unsubstituted with deuterium, halogen, or halogen ( C2-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cycloalkyl, fused with one or more aromatic rings ( C6-C30) cycloalkyl, R ^a R ^b R ^c Si-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, -NR ^d R ^e , -BR ^f R ^g , -PR ^h R ⁱ , -P (= 0) R ^j R ^k , (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, R ^l T-, R ^m C (= 0)-, R ^m C (= 0) O-, carboxyl, nitro or hydroxy selected from the group consisting of Or more, and R ^a to R ^l are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl; T is S or O; R ^m means (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy.

The organic light emitting compound may be represented by the following Chemical Formula 2 or 9.

[Formula 2]

(3)

[Formula 4]

[Chemical Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Wherein X ₂ is N or CH; Y is -O-, -S-, -C (R ₁₁ R ₁₂ )-or -N (R ₁₅ )-; L ₁ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C2-C30) heteroarylene; Ar ₁ is hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C2-C30) heteroaryl; R ₁ to R ₉ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, NR ₁₆ R ₁₇ or SiR ₁₈ R ₁₉ R ₂₀ ; R ₁₁ , R ₁₂ , R ₁₅ and R ₁₆ to R ₂₀ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted Substituted (C2-C30) heteroaryl, wherein R ₁₆ and R ₁₇ are substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkene, with or without fused ring; It may be linked to niylene 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 one or more heteroatoms selected from nitrogen, oxygen and sulfur May be substituted.]

More specifically, X ₂ is N or CH; Y is -O-, -S-, -C (R ₁₁ R ₁₂ )-or -N (R ₁₅ )-;

L ₁ is a single bond or arylene selected from the following structures;

R ₃₁ and R ₃₂ are independently of each other methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n -Octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, pyridyl or quinolyl ego;

Ar ₁ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2 -Ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, terphenyl, naphthyl, 9,9 -Diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or N-phenylcarbazolyl, phenyl of said Ar ₁ , biphenyl , Terphenyl, naphthyl and carbazolyl are deuterium, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n- Hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, triphenylsilyl Trimethylsilyl , Dimethylphenylsilyl, diphenylmethylsilyl, phenyl and naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, phenylpyridyl, carbazolyl, fluoranthenyl, dibenzofuranyl It may be further substituted with one or more substituents selected from the group consisting of dibenzothiophenyl;

R ₁ to R ₉ are independently of each other hydrogen, deuterium, phenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, amino or carbazolyl; R ₁₁ , R ₁₂ and R ₁₅ are each independently hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n- Hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, bi Phenyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, naphthyl, pyridyl, N-phenylcarbazolyl or quinolyl, wherein the phenyl of R ₁₁ , R ₁₂ and R ₁₅ is Deuterium, halogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2- May be further substituted with one or more selected from ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl and naphthyl , R ₁₁ and R ₁₂ may be bonded to each other to form a ring.

The organic light emitting compound according to the present invention may be more specifically exemplified as the following compound, but the following compound does not limit the present invention.

The organic light emitting compound according to the present invention can be prepared as shown in Scheme 1 below.

Scheme 1

[A ring in Scheme 1, X ₁ , X ₂ , L ₁ , Ar ₁ , R _{1 ,} R _{2 ,} R _{3 ,} a, b, c and Z are the same as defined in Formula 1; Hal is 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 organic light emitting compound of Formula 1. The organic material layer includes a light emitting layer, and the organic light emitting compound of Chemical Formula 1 is used as a host material in the light emitting layer.

When the organic light emitting compound of Formula 1 is used as a host in the light emitting layer is characterized in that it comprises at least one phosphorescent dopant. The phosphorescent dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but the phosphorescent dopant applied to the organic electroluminescent device of the present invention is preferably selected from compounds represented by the following Chemical Formula 10.

[Formula 10]

M ^One L ¹⁰¹ L ¹⁰² L ¹⁰³

Wherein M ¹ is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ Are independently selected from the following structures.

R ₂₀₁ to R ₂₀₃ are independently of each other hydrogen, deuterium, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl;

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 each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ are fused to 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 (C2-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 (C3-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 independently of one another are hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C3-C30) cycloalkyl, or may be linked to an adjacent substituent by alkylene or alkenylene to form a spiro ring or fused ring, or R ₂₀₇ or R ₂₀₈ with alkylene or alkenylene To form a saturated or unsaturated fused ring.]

The phosphorescent dopant compound of Formula 10 may be exemplified as a compound having the following structure, but is not limited thereto.

In the organic electroluminescent device of the present invention, it may include one or more compounds selected from the group consisting of an organic light emitting compound of formula (1) and at the same time an arylamine compound or styrylarylamine compound. The arylamine-based compound or styrylarylamine-based compound is exemplified in Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but is not limited thereto.

In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic light emitting compound of Chemical Formula 1, a group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element It may further comprise one or more metals or complex compounds selected from, the organic material layer may include a light emitting layer and a charge generating layer.

In addition, an organic electroluminescent device that emits white light may be formed by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound. The compound emitting blue, green, or red light is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.

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. Examples of the chalcogenide include SiO _x (1 ≦ _X ≦ ₂ ), AlO _X (1 ≦ _X ≦ 1.5), SiON, SiAlON, and the like, and examples of the metal halide include LiF, MgF ₂ , CaF ₂ , and fluoride. Rare earth metals and the like are preferable. Examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

Further, in the organic electroluminescent device of the present invention, disposing a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of the pair of electrodes thus produced desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region into 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, the reducing dopant layer The white organic electroluminescent device having two or more light emitting layers may be manufactured using the 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 a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.

Preparation Example 1 Preparation of Compound 1

compound 1-1 Manufacture

8.1 g (40.6 mmol) of 2,4-dichloroquinazoline, 5.0 g (40.6 mmol) of phenylboronic acid, 200 mL of toluene, 50 mL of ethanol and 50 mL of water, and then 1.9 g (1.64 mmol) of Pd (PPh ₃ ) ₄ and K 12.9 g (122 mmol) of ₂ CO ₃ were added. The mixture was stirred at 120 ° C. for 5 hours, then cooled to room temperature and terminated with 200 mL of aqueous ammonium chloride solution. The mixture was extracted with EA 500mL and washed with 50mL of distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , and the organic solvent was removed under reduced pressure. Recrystallization after the silica gel filter yielded 6.6 g (68%) of compound 1-1 .

compound 1-2 Manufacture

8.9 g (41.10 mmol) of 7H-benzo [c] carbazole, 11.9 g (49.32 mmol) of compound 1-1 , 0.46 g of Pd (OAc) ₂ , 7.9 g (82.20 mmol) of NaOt-bu, 100 mL of toluene, P (t -bu) ₃ 2mL (4.11mmol, 50% in toluene) was added and stirred under reflux. After 10 hours, the mixture was cooled to room temperature, distilled water was added, and extracted with EA. It was dried over anhydrous MgSO ₄ and dried under reduced pressure. Separation column to obtain a compound 1-2 14.5g (84%).

Cargo 1-3 Manufacture

14.3 g (33.98 mmol) of compound 1-2 are placed in a 1-neck flask, and the mixture is filled with argon. Add 500 mL of THF and stir at 0 ° C. for 10 minutes. Add 7.35 g (40.78 mmol) of NBS and stir at room temperature for one day. At the end of the reaction, extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Then, 14.6 g (85%) of Compound 1-3 was obtained by column chromatography using hexane and EA as developing solvents.

compound 1-4 Manufacture

13.2 g (26.30 mmol) of compound 1-3 are placed in a 1-neck flask, and the flask is filled with argon. Add 500 mL of THF and stir for 10 minutes at -78 ° C. 15.8 mL (39.45 mmol) of n-BuLi (2.5 M in hexane) is added dropwise and stirred at −78 ° C. for 1 hour 30 minutes. 4.85 mL (39.45 mmol) trimethylborate is added at -78 ° C. Stir for 30 minutes at -78 ° C and then for 4 hours at room temperature. At the end of the reaction, extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Then, 6.9 g (18.05 mmol, 65%) of Compound 1-4 was obtained by column chromatography using hexane and EA as developing solvents.

compound One Manufacture

Compound 1-4 8.1 g (17.4 mmol), 3-bromo-9-phenyl-9H-carbazole 6.7 g (20.88 mmol), Pd (PPh ₃ ) ₄ 0.8 g (0.7 mmol), 2M K ₂ CO ₃ aqueous solution 20 mL, toluene 100 mL and ethanol 50 mL were added and stirred under reflux for 12 hours. Wash with distilled water and extract with EA. It is dried over anhydrous MgSO ₄ and distilled under reduced pressure. Compound 1 (6.8 g, 10.3 mmol, 58%) was obtained by column separation.

MS / FAB: 663 (found), 662.78 (calculated)

Preparation Example 2 Preparation of Compound 2

compound 2-1 Manufacture

8.1 g (40.6 mmol) of 2,4-dichloroquinazoline, 8.0 g (40.6 mmol) of biphenyl phenylboronic acid, 200 mL of toluene, 50 mL of ethanol and 50 mL of water, followed by 1.9 g (1.64 mmol) of Pd (PPh ₃ ) ₄ And 12.9 g (122 mmol) of K ₂ CO ₃ were added. The mixture was stirred at 120 ° C. for 5 hours, then cooled to room temperature and terminated with 200 mL of aqueous ammonium chloride solution. The mixture was extracted with EA 500mL and washed with 50mL of distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , and the organic solvent was removed under reduced pressure. After recrystallization after silica gel filter, 8.2 g (25.9 mmol, 64%) of Compound 2-1 was obtained.

compound 2-2 Manufacture

9.5 g (19.1 mmol, 74%) of Compound 2-2 was prepared by the same method as the compound 1-2 .

compound 2-3 Manufacture

9.0 g (15.6 mmol, 82%) of Compound 2-3 was prepared by the same method as the compound 1-3 .

compound 2-4 Manufacture

4.0 g (7.4 mmol, 47%) of Compound 2-4 was prepared by the same method as the compound 1-4 .

compound 2 Manufacture

4.0g compound 2-4 to prepare a (7.4mmol) and 3-bromo-9-phenyl -9H- carbazol 6.7g (20.88mmol) of the compound 2 2.8g (4.6mmol, 51%) in the same manner as Compound 1 It was.

MS / FAB: 739 (found), 738.87 (calculated).

Preparation Example 3 Preparation of Compound 7

compound 7 Manufacture

Compound 2-4 4.0g (7.4mmol) and 2-bromo modayi dibenzo [b, d] thiophene 5.5g (20.88mmol) of the compound 7 in the same manner as Compound 1 2.8g (4.6mmol, 51%) was prepared .

MS / FAB: 604 (found), 603.73 (calculated).

Preparation Example 4 Preparation of Compound 12

compound 12 Manufacture

Compound 1-4 6.9g (18.05mmol) and the 10-bromo-7-phenyl -7H- benzo [c] carbazole 7.8g (20.88mmol) in the same manner as Compound 1, Compound 12 6.8g (9.5mmol, 53 %) Was prepared.

MS / FAB: 713 (found), 712.84 (calculated).

Preparation Example 5 Preparation of Compound 16

compound 16 Manufacture

9.8 g (18.05 mmol) of compound 2-4 and 5.7 g (20.88 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene were prepared in the same manner as compound 1 (7.6 g (11.0 mmol, 61%) of compound 16. ) Was prepared.

MS / FAB: 690 (found), 689.84 (calculated).

Preparation Example 6 Preparation of Compound 25

compound 6-1 Manufacture

20 g (92 mmol) of 7H-benzo [c] carbazole and 43.5 g (184 mmol) of 1-bromo-4-iodinebenzene were dissolved in 500 mL of toluene, followed by 8.8 g (46 mmol) of CuI and 6.2 mL (92 mmol) of diaminoethane. 8.7 g (276 mmol) K ₃ PO ₄ was added and refluxed for 30 h. After cooling the reaction mixture to room temperature, the reaction was terminated with 50 mL of 2.0M aqueous hydrochloric acid solution, extracted with EA 1L, and washed with distilled water 200mL. The obtained organic layer was dried over anhydrous MgSO ₄ , and the organic solvent was removed under reduced pressure. Purified by silica gel column chromatography to obtain 19g (56%) of compound 6-1 .

compound 6-2 Manufacture

19 g (51 mmol) of Compound 6-1 was dissolved in 250 mL of THF, and then cooled to −78 ° C., and then 24.5 mL of n-BuLi (2.5 M in hexane) was added at −78 ° C. The mixture was stirred at −78 ° C. for 1 h, then 8.5 mL of B (OMe) ₃ was added, stirred for 2 h and the reaction was terminated with 100 mL of aqueous ammonium chloride solution. Then, after extracting with EA 500mL, and washed with distilled water 100mL. The obtained organic layer was dried over anhydrous MgSO ₄ , and the organic solvent was removed under reduced pressure. Recrystallization yielded 14 g (81%) of compound 6-2 .

compound 6-3 Manufacture

3.3 g (13.7 mmol) of compound 1-1 and 5.5 g (16.4 mmol) of compound 6-2 were mixed with 100 mL of toluene, 20 mL of ethanol and 20 mL of water, followed by 1.6 g (1.4 mmol) of Pd (PPh ₃ ) ₄ and K ₂ CO. ₃ 5.7 g (41.1 mmol) was added. The mixture was stirred at 120 ° C. for 5 hours, then cooled to room temperature and terminated with 20 mL of aqueous ammonium chloride solution. The mixture was extracted with EA 250mL and washed with distilled water 30mL. The obtained organic layer was dried over anhydrous MgSO ₄ , and the organic solvent was removed under reduced pressure. Recrystallization after the silica gel filter yielded 4.9 g (9.8 mmol, 72%) of compound 6-3 .

compound 6-4 Manufacture

4.3 g (7.5 mmol, 76%) of Compound 6-4 was prepared by the same method as the compound 1-3 .

compound 6-5 Manufacture

1.7 g (3.1 mmol, 43%) of Compound 6-5 was prepared by the same method as the compound 1-4 .

compound 25 Manufacture

7.6 g (10.3 mmol, 57%) of Compound 25 was prepared by the same method as Compound 1, with 9.8 g (18.05 mmol) of Compound 6-5 and 6.7 g (20.88 mmol) of 3-bromo-9-phenyl-9H-carbazole. It was.

MS / FAB: 739 (found), 738.87 (calculated)

Preparation Example 7 Preparation of Compound 37

compound 7-1 Manufacture

50 g (0.23 mol) of 7H-benzo [c] carbazole was dissolved in 1.4 L of DMF, and 41 g (0.23 mol) of NBS was added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the mixture was extracted with EA and distilled under reduced pressure. 53.2 g (78%) of Compound 7-1 was obtained by column separation with silica.

compound 7-2 Manufacture

30 g (0.10 mol) of compound 7-1 , 22.6 mL (0.20 mmol) of iodine benzene, 9.6 g (0.05 mol) of CuI, 99 g (0.030 mol) of Cs ₂ CO ₃ and 13.7 mL (0.20 mol) of EDA were added to 500 mL of toluene. The reflux was stirred for 24 hours. After extraction with EA and distillation under reduced pressure, 20 g (53%) of Compound 7-2 was obtained by column separation with MC / Hex.

compound 7-3 Manufacture

18 g (48.4 mmol) of Compound 7-2 was dissolved in 250 mL of THF, and 23.2 mL (58.0 mmol) of 2.5 M n-BuLi (in Hexane) was added at -78 ° C, and the mixture was stirred for 1 hour. 16.7 mL (72.5 mmol) of B (Oi-Pr) ₃ was slowly added and stirred for 2 hours. 2M HCl was added and quenched, followed by extraction with distilled water and EA. Recrystallization with MC and Hex afforded 13.6 g (83.4%) of compound 7-3 .

compound 7-4 Manufacture

Compound 7-3 13.6 g (40.3 mmol), bromocarbazole 9.9 g (40.3 mmol), Pd (PPh ₃ ) ₄ 2.3 g (2.0 mmol), K ₂ CO ₃ 13.4 g (96.7 mmol), 200 mL of toluene and 48 mL of distilled water After mixing the mixture was stirred at 90 ℃ 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 15 g (81%) of Compound 7-4 .

compound 37 Manufacture

4 g (16.6 mmol) of Compound 1-1 and 7.6 g (16.6 mmol) of Compound 7-4 were suspended in 80 mL of DMF, and then 1.1 g (28.2 mmol) of 60% NaH was added at room temperature, followed by stirring for 12 hours. 1 L of distilled water was added, followed by filtration under reduced pressure. The obtained solid was triturated with MeOH / EA, dissolved in MC, silica filtered, and triturated with MC / n-Hexane to obtain 2.4 g (21.8%) of Compound 37 .

MS / FAB found 662.78, calculated 662.25

Preparation Example 8 Preparation of Compound 116

compound 8-1 Manufacture

Compound 7-1 (10 g, 33.8 mmol), dibenzo [ b , d ] furan-4-ylboronic acid (8.6 g, 40.56 mmol), Pd (PPh ₃ ) ₄ (2 g, 1.7 mmol), K ₂ CO ₃ (34 g, 321 mmol), 60 mL of toluene, 12 mL of EtOH, and 12 mL of purified water were mixed and stirred at 120 ° C. for 15 hours. After completion of the reaction, the mixture was left to stand and the organic layer was concentrated after removing the aqueous layer. Silica column purification gave compound 8-1 (10.2 g, 78%).

compound 116 Manufacture

3 g (7.8 mmol) of Compound 8-1 and 2.1 g (7.8 mmol) of Compound 2-1 were suspended in 30 mL of DMF, and then 376 mg (9.4 mmol) of 60% NaH was added at room temperature, followed by stirring for 12 hours. 500 mL of purified water was added and filtered under reduced pressure. The obtained solid was triturated with MeOH / EA, triturated with DMF, and triturated with EA / THF. 2.4 g (46%) of Compound 116 was obtained by trituration with MeOH / EA after melting with MC and silica filtering.

MS / FAB found 663.76, calculated 663.23

Preparation Example 9 Preparation of Compound 128

compound 9-1 Manufacture

5 g (20.32 mmol) of 3-bromo-9H-carbazole, 4.7 g (22.35 mmol) of dibenzo [ b , d ] furan-4-ylboronic acid, 7 g (50.79 mmol) of K ₂ CO ₃ , Pd (PPh ₃ ) ₄ 1.17 g (1.01 mmol), toluene 100 mL, EtOH 25 mL and purified water 25 mL were mixed and stirred at 100 ° 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 organic layer was concentrated and purified by silica column purification to obtain 4.3 g (64%) of compound 9-1 .

compound  128 Manufacture

3 g (8.99 mmol) of Compound 2-1 and 3.14 g (9.89 mmol) of Compound 9-1 were suspended in 50 mL of anhydrous DMF, and 0.54 g (13.5 mmol) of 60% NaH was added at room temperature. Stir at room temperature for 5 hours. After completion of the reaction, 3 mL of MeOH was added dropwise to obtain a solid with an excess of MeOH. The silica column was purified, suspended with EA, filtered, and THF crystallized to obtain Compound 128 1g (18%).

MS / FAB found 613.70, calculated 613.22

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, 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. Used. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N ¹ , N ^{1 ′} -([1,1′-biphenyl] -4,4′-diyl) bis ( N 1-(naphthalen- ¹ -yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) (N ¹ , N ^{1 '} -([1,1'-biphenyl] -4,4' -diyl) bis (N ^1- (naphthalen-1-yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) was added and evacuated until the vacuum in the chamber reached 10 ^-6 torr. A current was applied and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate, followed by N, N'-die (4-biphenyl) -N, N'-die (4) in another cell in the vacuum deposition equipment. -Biphenyl) -4,4'-diaminobiphenyl (N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl) is added thereto, and the cell A current was 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 were formed, the light emitting layer was deposited thereon as follows. The hole transport by putting the compound 1 according to the invention as a host in one cell in the deposition equipment, and then the other cell into the compound D-11 respectively, as a dopant, evaporated to two materials at different rates doped with 4% by weight A 30 nm thick light emitting layer was deposited on the layer, followed by 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1- in one cell as an electron transporting layer on the light emitting layer. Phenyl-1H-benzo [d] imidazole (2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole) Lithium quinolate was added to each cell, and the electron transfer layer of 30 nm was deposited by evaporating the two materials at the same rate and doping at 50% by weight. After depositing (Lithium quinolate) to a thickness of 2nm, using another vacuum deposition equipment to deposit an Al cathode to a thickness of 150nm OL An ED device was produced. Each compound was used by vacuum sublimation purification under 10 ^-6 torr.

As a result, a current of 8.8 mA / cm ² flowed at a voltage of 4.4 V, and red light emission of 900 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 2 according to the present invention was used as a host material in the light emitting layer, and D-7 was used as a dopant.

As a result, a current of 22.9 mA / cm ² flowed at a voltage of 4.9 V, and red emission of 2710 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 25 according to the present invention was used as a host material in the emission layer.

As a result, a current of 16.9 mA / cm ² flowed at a voltage of 4.8 V, and red light emission of 1780 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 37 according to the present invention was used as a host material in the light emitting layer, and D-7 was used as a dopant.

As a result, a current of 41.2 mA / cm ² flowed at a voltage of 5.5 V, and red light emission of 4800 cd / m ² was confirmed.

Example 5 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 128 according to the present invention was used as a host material in the light emitting layer, and D-7 was used as a dopant.

As a result, a current of 8.7 mA / cm ² flowed at a voltage of 4.2 V, and red light emission of 900 cd / m ² was confirmed.

Example 6 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 116 according to the present invention was used as a host material in the light emitting layer, and D-7 was used as a dopant.

As a result, a current of 3.2 mA / cm ² flowed at a voltage of 4.1 V, and red light emission of 400 cd / m ² was confirmed.

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

4,4'-N, N'-dicarbazole-biphenyl (4,4'-N, N'-dicarbazole-biphenyl) is used as a light emitting material and compound D-11 is used as a dopant. A light emitting layer was deposited and aluminum (III) bis (2-methyl-8-quinolinate) 4-phenylphenolate (aluminum (III) bis (2-methyl-8) was used as a hole blocking layer between the light emitting layer and the electron transporting layer. OLED device was manufactured in the same manner as in Example 1, except that -quinolinato) 4-phenylphenolate) was deposited to a thickness of 10 nm.

As a result, a current of 20.0 mA / cm ² flowed at a voltage of 8.2 V, and red light emission of 1000 cd / m ² was confirmed.

It was confirmed that the luminescence properties of the organic light emitting compounds developed in the present invention showed superior properties compared to the conventional materials. In addition, the device using the organic light emitting compound according to the present invention as a light emitting host material was not only excellent in the light emission characteristics, but also by lowering the driving voltage to increase the power efficiency to improve the power consumption.

Claims (10)

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

[In the above formula (1)
Ring A is a monocyclic or polycyclic aromatic ring;
X ₁ and X ₂ are independently of each other N or CR ′;
L ₁ is a single bond, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C2-C30) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene;
Ar ₁ is hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C2-C30) heteroaryl;
Z are each independently selected from the following structures;

Provided that when A ring is a monocyclic aromatic ring, Z is selected from the following structures;

Y is —O—, —S—, —C (R ₁₁ R ₁₂ ) —, —Si (R ₁₃ R ₁₄ ) — or —N (R ₁₅ ) —;
R ₁ to R ₉ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-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, (C3 Substituted or unsubstituted (C6-C30) aryl wherein one or more cycloalkyl is fused, 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic, wherein one or more substituted or unsubstituted aromatic rings are fused. One or more fused (C3-C30) cycloalkyl, -NR ₁₆ R ₁₇ , -SiR ₁₈ R ₁₉ R ₂₀ , -SR ₂₁ , -OR _{22 ,} cyano, nitro or hydroxy, or R ₁ to R ₉ each represents a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C) with or without adjacent substituents and fused rings 30) 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 'and R ₁₁ to R ₂₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2- C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl or substituted or unsubstituted with or without fused ring with adjacent substituents ( C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene may be linked to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the alicyclic ring and monocyclic or polycyclic formed above The carbon atoms of the aromatic ring may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a, c, e and i are each independently integers of 1 to 4, and when a, c, e and i are integers of 2 or more, each of R ₁ , R ₃ , R ₅ and R ₉ may be the same or different; ;
b, d, g are each independently an integer of 1 to 3, and when b, d, g is an integer of 2 or more, each of R ₂ , R ₄ and R ₇ may be the same or different;
f is an integer from 1 to 6, and when f is an integer of 2 or more, each R ₆ may be the same or different;
h is an integer from 1 to 5, and when h is an integer of 2 or more, each R ₈ may be the same or different;
Wherein said heteroaromatic ring, heteroarylene, 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 further substituted with L ₁ , Ar ₁ , R ₁ to R ₉ , R ′ and R ₁₁ to R ₂₂ are each independently deuterium, halogen, (C 1 -C 30) alkyl unsubstituted or substituted with halogen, (C 6 -C30) aryl, (C6-C30) aryl substituted or unsubstituted (C2-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocyclo fused with one or more aromatic rings Alkyl, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, R ^a R ^b R ^c Si-, (C2-C30) alkenyl, (C2-C30) alkynyl, Cyano, carbazolyl, -NR ^d R ^e , -BR ^f R ^g , -PR ^h R ⁱ , -P (= O) R ^j R ^k , (C6-C30) ar (C1-C30) alkyl, (C1 -C30) alkyl (C6-C30) aryl, R ¹ T-, R ^m C (= 0)-, R ^m C (= 0) O-, one selected from the group consisting of carboxyl, nitro or hydroxy And R ^a to R ^l are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl; T is S or O; R ^m is (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy. The method of claim 1,
An organic light emitting compound, characterized in that selected from the formula 2 to 9.
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Formula 6]

[Formula 7]

[Chemical Formula 8]

[Formula 9]

[Wherein X ₂ is N or CH; Y is -O-, -S-, -C (R ₁₁ R ₁₂ )-or -N (R ₁₅ )-; L ₁ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C2-C30) heteroarylene; Ar ₁ is hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C2-C30) heteroaryl; R ₁ to R ₉ are independently of each other hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, NR ₁₆ R ₁₇ or SiR ₁₈ R ₁₉ R ₂₀ ; R ₁₁ , R ₁₂ , R ₁₅ and R ₁₆ to R ₂₀ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted Substituted (C2-C30) heteroaryl, wherein R ₁₆ and R ₁₇ are substituted or unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkene, with or without fused ring; It may be linked to niylene 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 one or more heteroatoms selected from nitrogen, oxygen and sulfur May be substituted.] The method of claim 3,
X ₂ is N or CH; Y is -O-, -S-, -C (R ₁₁ R ₁₂ )-or -N (R ₁₅ )-;
L ₁ is a single bond or arylene selected from the following structures;

R ₃₁ and R ₃₂ are independently of each other methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n -Octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, pyridyl or quinolyl ego;
Ar ₁ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2 -Ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, terphenyl, naphthyl, 9,9 -Diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or N-phenylcarbazolyl, phenyl of said Ar ₁ , biphenyl , Terphenyl, naphthyl and carbazolyl are deuterium, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n- Hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, triphenylsilyl Trimethylsilyl , Dimethylphenylsilyl, diphenylmethylsilyl, phenyl and naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, phenylpyridyl, carbazolyl, fluoranthenyl, dibenzofuranyl It may be further substituted with one or more substituents selected from the group consisting of dibenzothiophenyl;
R ₁ to R ₉ are independently of each other hydrogen, deuterium, phenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, amino or carbazolyl; R ₁₁ , R ₁₂ and R ₁₅ are each independently hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n- Hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, bi Phenyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, naphthyl, pyridyl, N-phenylcarbazolyl or quinolyl, wherein the phenyl of R ₁₁ , R ₁₂ and R ₁₅ is Deuterium, halogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2- May be further substituted with one or more selected from ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl and naphthyl , R ₁₁ and R ₁₂ may be bonded to each other to form a ring. The method of claim 4, wherein
An organic light emitting compound, which is selected from the following compounds.

An organic electroluminescent device comprising the organic light emitting compound according to any one of claims 1 to 5. The method of claim 6,
The organic light emitting diode includes a first electrode; A second electrode; And one or more organic material layers interposed between the first and second electrodes, wherein the organic material layers include one or more organic light emitting compounds and one or more phosphorescent dopants represented by the following Chemical Formula 10: EL device.
[Formula 10]
M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³
Wherein M ¹ is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ Are independently selected from the following structures.
[Formula 10]
M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³
Wherein M ¹ is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ Are independently selected from the following structures.

R ₂₀₁ to R ₂₀₃ are independently of each other hydrogen, deuterium, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl;
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 each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R ₂₂₄ and R ₂₂₅ are fused to 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 (C2-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 independently of one another are hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C3-C30) cycloalkyl, or may be linked to an adjacent substituent by alkylene or alkenylene to form a spiro ring or fused ring, or R ₂₀₇ or R ₂₀₈ with alkylene or alkenylene 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
The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. The method of claim 7, wherein
The organic light emitting device of claim 1, further comprising at least one organic light emitting layer for emitting blue, red or green light to the organic material layer.