KR20140006708A - New organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

New organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDF

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KR20140006708A
KR20140006708A KR1020130062997A KR20130062997A KR20140006708A KR 20140006708 A KR20140006708 A KR 20140006708A KR 1020130062997 A KR1020130062997 A KR 1020130062997A KR 20130062997 A KR20130062997 A KR 20130062997A KR 20140006708 A KR20140006708 A KR 20140006708A
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light emitting
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organic electroluminescent
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compound
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KR101529164B1 (en
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안도환
김복영
박재교
안중복
전아람
이대균
한근희
현승학
박노길
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(주)씨에스엘쏠라
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

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Abstract

The present invention provides a novel organic electroluminescent compound represented by chemical formula 1 and an organic electroluminescent device including the same. The organic electroluminescent compound is a green phosphorescent host material, can be applied to the organic electroluminescent device, and can improve the luminous efficiency of the organic electroluminescent device and the lifetime of the device.

Description

신규한 유기발광화합물 및 이를 포함하는 유기전기발광소자{NEW ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same.

본 발명은 신규한 유기발광화합물 및 이를 포함하는 유기전기발광소자에 관한 것으로, 보다 구체적으로는 인광 녹색 호스트 물질로서 사용되는 신규한 유기발광화합물 및 이를 채용하고 있는 유기 발광 소자에 관한 것이다.
The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly to a novel organic light emitting compound used as a phosphorescent green host material and an organic light emitting device employing the same.

OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전기발광의 메커니즘 상 인광 재료의 개발은 이론적으로 4배까지 발광 효율을 개선시킬 수 있는 가장 좋은 방법 중 하나이다. 현재까지 이리듐(III)착물 계열이 인광 발광 재료로 널리 알려져 있으며, 각 RGB 별로는 (acac)Ir(btp)2, Ir(ppy)3 및 Firpic 등의 재료가 알려져 있다. 특히, 최근 일본, 구미에서 많은 인광 재료들이 연구되고 있다.The most important factor determining the luminous efficiency in an OLED is a light emitting 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. Until now, iridium (III) complexes have been widely known as phosphorescent materials. Materials such as (acac) Ir (btp) 2, Ir (ppy) 3 and Firpic are known for each RGB. In particular, many phosphorescent materials have recently been studied in Japan and Europe.

인광 발광체의 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있으며, BCP, BAlq 등의 정공차단층을 적용한 고효율의 OLED가 공지되어 있으며, 일본의 파이오니어 등에서는 BAlq유도체를 호스트로 이용한 고성능의 OLED를 공지한 바 있다.CBP is the most widely known host material for phosphorescent emitters. To date, high-efficiency OLEDs using hole blocking layers such as BCP and BAlq are known, and high-performance OLEDs using BAlq derivatives as a host are known in Pioneer, Japan. I've done it.

그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변하는 등 단점을 갖고 있다. OLED에서 전력효율= (π/전압) × 전류효율 이므로, 전력효율은 전압에 반비례하는데, OLED의 소비 전력이 낮으려면 전력 효율이 높아야한다. 실제 인광 발광 재료를 사용한 OLED는 형광 발광 재료를 사용한 OLED에 비해 전류 효율(cd/A)이 상당히 높으나, 인광 발광 재료의 호스트로 BAlq나 CBP 등 종래의 재료를 사용할 경우, 형광재료를 사용한 OLED에 비해 구동 전압이 높아서 전력 효율(lm/w)면에서 큰 이점이 없다. 또한, OLED 소자에서의 수명 측면에서도 결코 만족할만한 수준이 되질 못하여 더욱 안정되고, 더욱 성능이 뛰어난 호스트 재료의 개발이 요구되고 있다.
However, existing materials have advantages in terms of luminescent properties, but they have disadvantages such as low glass transition temperature and very poor thermal stability, which can cause material changes when subjected to a high temperature deposition process under vacuum. In the OLED, power efficiency = (π / voltage) × current efficiency, so the power efficiency is inversely proportional to the voltage. To lower the power consumption of the OLED, the power efficiency must be high. In fact, OLEDs using phosphorescent materials have a significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials.However, when a conventional material such as BAlq or CBP is used as a host of phosphorescent materials, OLEDs using fluorescent materials are used. Compared with the higher driving voltage, there is no big advantage in terms of power efficiency (lm / w). In addition, since the lifetime of the OLED device is never satisfactory, development of a more stable and more excellent host material is required.

본 발명은 인광 녹색 호스트 물질로서 유기 발광 소자에 적용할 수 있고, 유기 발광 소자에 적용할 경우 구동전압을 낮출 수 있으며, 발광효율, 휘도, 열적 안정성 및 소자 수명을 향상시킬 수 있는 유기발광화합물을 제공하는 것을 목적으로 한다.The present invention can be applied to an organic light emitting device as a phosphorescent green host material, and when applied to an organic light emitting device can lower the driving voltage, an organic light emitting compound that can improve the luminous efficiency, brightness, thermal stability and device life It aims to provide.

또한, 본 발명은 상기 화합물을 이용한 유기 발광 소자를 제공하는 것을 목적으로 한다.
Another object of the present invention is to provide an organic light emitting device using the above compound.

본 발명은 하기 화학식 1로 표시되는 유기발광화합물을 제공한다:The present invention provides an organic electroluminescent compound represented by the following formula (1): < EMI ID =

[화학식1][Chemical Formula 1]

Figure pat00001
Figure pat00001

상기 식에서,Where

X는

Figure pat00002
,
Figure pat00003
,
Figure pat00004
,
Figure pat00005
,
Figure pat00006
,
Figure pat00007
,
Figure pat00008
,
Figure pat00009
,
Figure pat00010
,
Figure pat00011
,
Figure pat00012
,
Figure pat00013
,
Figure pat00014
,
Figure pat00015
,
Figure pat00016
,
Figure pat00017
,
Figure pat00018
,
Figure pat00019
,
Figure pat00020
,
Figure pat00021
,
Figure pat00022
,
Figure pat00023
,
Figure pat00024
,
Figure pat00025
,
Figure pat00026
,
Figure pat00027
또는
Figure pat00028
이며, 상기에서 W는 질소원자, 산소원자, 황원자 또는 Si(C1~C5의 알킬)2이며, R1은 각각 독립적으로 페닐, 피롤, 피라졸, 이미다졸, 트리아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐 또는 나프틸기이며, W가 산소원자, 황원자 또는 Si(C1~C5의 알킬)2인 경우에 R1은 부존재하며;X is
Figure pat00002
,
Figure pat00003
,
Figure pat00004
,
Figure pat00005
,
Figure pat00006
,
Figure pat00007
,
Figure pat00008
,
Figure pat00009
,
Figure pat00010
,
Figure pat00011
,
Figure pat00012
,
Figure pat00013
,
Figure pat00014
,
Figure pat00015
,
Figure pat00016
,
Figure pat00017
,
Figure pat00018
,
Figure pat00019
,
Figure pat00020
,
Figure pat00021
,
Figure pat00022
,
Figure pat00023
,
Figure pat00024
,
Figure pat00025
,
Figure pat00026
,
Figure pat00027
or
Figure pat00028
Wherein W is a nitrogen atom, an oxygen atom, a sulfur atom or Si (alkyl of C1 ~ C5) 2 , and each R1 is independently phenyl, pyrrole, pyrazole, imidazole, triazole, pyridinyl, pyrimidinyl, Is a pyrazinyl, pyridazinyl, triazinyl or naphthyl group, and R 1 is absent when W is an oxygen atom, a sulfur atom or Si (alkyl of C 1 to C 5) 2 ;

Y는 질소 또는 탄소원자이며, Y 중 적어도 하나는 질소원자이며;Y is nitrogen or a carbon atom and at least one of Y is a nitrogen atom;

n은 0 또는 1이며;n is 0 or 1;

R2 내지 R5는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3또는 Si(CH3)3이거나,R 2 to R 5 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF 3 or Si (CH 3 ) 3, or

중수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3,Si(CH3)3,페닐, 바이페닐, 나프틸, 페난트레닐, 플루오레닐, 피롤, 피라졸, 이미다졸, 트리아졸, 옥사졸, 옥사디아졸, 티오페닐, 티아졸, 티아디아졸, 피라지닐, 피리다지닐 피리디닐, 피리미디닐 및 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 탄소수 6~30의 아릴기 또는 탄소수 5~60의 헤테로아릴기이다.Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups It is a C6-C30 aryl group or C5-C60 heteroaryl group unsubstituted or substituted by the substituent.

또한, 본 발명은, Further, according to the present invention,

음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기전기발광소자에 있어서, An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

상기 유기 박막층 중 적어도 1층이 본 발명의 유기발광화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자를 제공한다.
At least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more.

본 발명에 따른 유기발광화합물은 인광 녹색 호스트 물질로서 유기 발광 소자에 적용할 수 있으며, 유기 발광 소자에 적용할 경우 구동전압을 낮추며, 발광효율, 휘도, 열적 안정성 및 소자 수명을 향상시킨다. The organic light emitting compound according to the present invention can be applied to an organic light emitting device as a phosphorescent green host material, when applied to the organic light emitting device lowers the driving voltage, improves luminous efficiency, brightness, thermal stability and device life.

또한, 본 발명의 유기발광화합물을 사용하여 제조되는 유기전기발광 소자는 고효율 및 장수명 특성을 갖는다.
In addition, the organic electroluminescent device manufactured using the organic electroluminescent compound of the present invention has high efficiency and long life.

본 발명은 하기 화학식 1로 표시되는 유기발광화합물에 관한 것이다:The present invention relates to organic electroluminescent compounds represented by the following general formula (1)

[화학식1][Chemical Formula 1]

Figure pat00029
Figure pat00029

상기 식에서,Where

X는

Figure pat00030
,
Figure pat00031
,
Figure pat00032
,
Figure pat00033
,
Figure pat00034
,
Figure pat00035
,
Figure pat00036
,
Figure pat00037
,
Figure pat00038
,
Figure pat00039
,
Figure pat00040
,
Figure pat00041
,
Figure pat00042
,
Figure pat00043
,
Figure pat00044
,
Figure pat00045
,
Figure pat00046
,
Figure pat00047
,
Figure pat00048
,
Figure pat00049
,
Figure pat00050
,
Figure pat00051
,
Figure pat00052
,
Figure pat00053
,
Figure pat00054
,
Figure pat00055
또는
Figure pat00056
이며, 상기에서 W는 질소원자, 산소원자, 황원자 또는 Si(C1~C5의 알킬)2이며, R1은 각각 독립적으로 페닐, 피롤, 피라졸, 이미다졸, 트리아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐 또는 나프틸기이며, W가 산소원자, 황원자 또는 Si(C1~C5의 알킬)2인 경우에 R1은 부존재하며;X is
Figure pat00030
,
Figure pat00031
,
Figure pat00032
,
Figure pat00033
,
Figure pat00034
,
Figure pat00035
,
Figure pat00036
,
Figure pat00037
,
Figure pat00038
,
Figure pat00039
,
Figure pat00040
,
Figure pat00041
,
Figure pat00042
,
Figure pat00043
,
Figure pat00044
,
Figure pat00045
,
Figure pat00046
,
Figure pat00047
,
Figure pat00048
,
Figure pat00049
,
Figure pat00050
,
Figure pat00051
,
Figure pat00052
,
Figure pat00053
,
Figure pat00054
,
Figure pat00055
or
Figure pat00056
Wherein W is a nitrogen atom, an oxygen atom, a sulfur atom or Si (alkyl of C1 ~ C5) 2 , and each R1 is independently phenyl, pyrrole, pyrazole, imidazole, triazole, pyridinyl, pyrimidinyl, Is a pyrazinyl, pyridazinyl, triazinyl or naphthyl group, and R 1 is absent when W is an oxygen atom, a sulfur atom or Si (alkyl of C 1 to C 5) 2 ;

Y는 질소 또는 탄소원자이며, Y 중 적어도 하나는 질소원자이며;Y is nitrogen or a carbon atom and at least one of Y is a nitrogen atom;

n은 0 또는 1이며;n is 0 or 1;

R2 내지 R5는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3또는 Si(CH3)3이거나,R 2 to R 5 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF 3 or Si (CH 3 ) 3, or

중수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3,Si(CH3)3,페닐, 바이페닐, 나프틸, 페난트레닐, 플루오레닐, 피롤, 피라졸, 이미다졸, 트리아졸, 옥사졸, 옥사디아졸, 티오페닐, 티아졸, 티아디아졸, 피라지닐, 피리다지닐 피리디닐, 피리미디닐 및 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 탄소수 6~30의 아릴기 또는 탄소수 5~60의 헤테로아릴기이다.Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups It is a C6-C30 aryl group or C5-C60 heteroaryl group unsubstituted or substituted by the substituent.

바람직하게는, 상기 탄소수 6~30의 아릴 또는 탄소수 5~60의 헤테로아릴기는 페닐, 나프틸, 바이페닐, 바이나프틸, 페난트레닐, 플루오레닐, 피롤, 피라졸, 이미다졸, 트리아졸, 옥사졸, 옥사디아졸, 티오페닐, 티아졸, 티아디아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 벤조티오페닐, 벤즈이미다졸, 벤조옥사졸, 벤즈티아졸, 카바졸, 퀴놀리닐, 이소퀴놀리닐, 인돌 또는 피레닐기 일 수 있다. Preferably, the aryl having 6 to 30 carbon atoms or the heteroaryl group having 5 to 60 carbon atoms is phenyl, naphthyl, biphenyl, binaphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole. , Oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzthiazole , Carbazole, quinolinyl, isoquinolinyl, indole or pyrenyl groups.

더욱 바람직하게는 More preferably,

상기 X는

Figure pat00057
,
Figure pat00058
,
Figure pat00059
,
Figure pat00060
,
Figure pat00061
,
Figure pat00062
,
Figure pat00063
,
Figure pat00064
,
Figure pat00065
,
Figure pat00066
,
Figure pat00067
,
Figure pat00068
,
Figure pat00069
,
Figure pat00070
,
Figure pat00071
,
Figure pat00072
,
Figure pat00073
,
Figure pat00074
,
Figure pat00075
,
Figure pat00076
,
Figure pat00077
,
Figure pat00078
,
Figure pat00079
,
Figure pat00080
,
Figure pat00081
,
Figure pat00082
또는
Figure pat00083
이며, 상기에서 W는 질소원자, 산소원자, 황원자 또는 Si(CH3)2이며, R1은 각각 독립적으로 페닐, 피리디닐 또는 피리미디닐기이며, W가 산소원자, 황원자 또는 Si(CH3)2인 경우에 R1은 부존재하며;X is
Figure pat00057
,
Figure pat00058
,
Figure pat00059
,
Figure pat00060
,
Figure pat00061
,
Figure pat00062
,
Figure pat00063
,
Figure pat00064
,
Figure pat00065
,
Figure pat00066
,
Figure pat00067
,
Figure pat00068
,
Figure pat00069
,
Figure pat00070
,
Figure pat00071
,
Figure pat00072
,
Figure pat00073
,
Figure pat00074
,
Figure pat00075
,
Figure pat00076
,
Figure pat00077
,
Figure pat00078
,
Figure pat00079
,
Figure pat00080
,
Figure pat00081
,
Figure pat00082
or
Figure pat00083
Wherein W is a nitrogen atom, an oxygen atom, a sulfur atom or Si (CH 3 ) 2 , and R 1 is each independently a phenyl, pyridinyl or pyrimidinyl group, and W is an oxygen atom, a sulfur atom or Si (CH 3 ) 2. R 1 is absent;

Y는 질소 또는 탄소원자이며, Y 중 적어도 하나는 질소원자이며;Y is nitrogen or a carbon atom and at least one of Y is a nitrogen atom;

n은 0 또는 1이며;n is 0 or 1;

R2 내지 R5는 수소원자인 일 수 있다. R2 to R5 may be a hydrogen atom.

본 발명의 유기발광화합물은 인광 녹색 호스트 물질로서 유용하게 사용될 수 있다. The organic light emitting compound of the present invention can be usefully used as a phosphorescent green host material.

본 발명의 유기발광화합물은 하기 [제1표군(群)]에 나타낸 화학구조를 가질 수 있다.The organic luminescent compound of the present invention may have the chemical structure shown in the following [first group (s)].

[제1표군(群)] [First group (group)]

Figure pat00084
Figure pat00085
Figure pat00086
Figure pat00087
Figure pat00084
Figure pat00085
Figure pat00086
Figure pat00087

본 발명은 또한,The present invention also relates to

음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기전기발광소자에 있어서, An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

상기 유기 박막층 중 적어도 1층이 본 발명의 유기발광화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자에 관한 것이다.Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more thereof.

상기 유기발광화합물은 인광 녹색 호스트 물질로서 유기전기발광소자에 포함될 수 있다. The organic light emitting compound may be included in the organic electroluminescent device as a phosphorescent green host material.

상기 유기전기발광소자는 The organic electroluminescent device

양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 가질 수 있다.An anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode stacked in this order.

이하에서, 본 발명의 유기전기발광소자에 대하여 예를 들어 설명한다. 그러나, 하기에 예시된 내용이 본 발명의 유기전기발광소자를 한정하는 것은 아니다.Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the following examples do not limit the organic electroluminescent device of the present invention.

본 발명의 유기전기발광소자는 양극(정공주입전극), 정공주입층(HIL) 및/또는 정공수송층(HTL), 발광층(EML) 및 음극(전자주입전극)이 순차적으로 적층된 구조를 가질 수 있으며, 바람직하게는, 양극과 발광층 사이에 전자차단층(EBL)을, 그리고 음극과 발광층 사이에 전자수송층(ETL), 전자주입층(EIL) 또는 정공차단층(HBL)을 추가로 포함할 수 있다.The organic electroluminescent device of the present invention may have a structure in which a cathode (a hole injection electrode), a hole injection layer (HIL) and / or a hole transport layer (HTL), a light emitting layer (EML) Preferably, an electron blocking layer (EBL) may be additionally provided between the anode and the light emitting layer, and an electron transport layer (ETL), an electron injection layer (EIL) or a hole blocking layer (HBL) have.

본 발명에 따른 유기전기발광소자의 제조방법으로는, 먼저 기판 표면에 양극용 물질을 통상적인 방법으로 코팅하여 양극을 형성한다. 이때, 사용되는 기판은 투명성, 표면 평활성, 취급 용이성 및 방수성이 우수한 유리기판 또는 투명 플라스틱 기판이 바람직하다. 또한, 양극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등이 사용될 수 있다.In the method of manufacturing an organic electroluminescence device according to the present invention, a cathode material is coated on the surface of a substrate by a conventional method to form a cathode. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. As the material for the positive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity may be used.

다음으로, 상기 양극 표면에 정공주입층(HIL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 정공주입층을 형성한다. 이러한 정공주입층 물질로는 구리프탈로시아닌(CuPc), 4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민(m-MTDATA), 4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠(m-MTDAPB), 스타버스트(starburst)형 아민류인 4,4',4"-트리(N-카바졸릴)트리페닐아민(TCTA), 4,4',4"-트리스(N-(2-나프틸)-N-페닐아미노)-트리페닐아민(2-TNATA) 또는 이데미츠사(Idemitsu)에서 구입가능한 IDE406을 예로 들 수 있다.Next, a hole injection layer (HIL) material is formed on the surface of the anode by vacuum thermal deposition or spin coating using a conventional method. Examples of such hole injection layer materials include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4' Amino) phenoxybenzene (m-MTDAPB), starburst type amines such as 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4' Triphenylamine (2-TNATA) or IDE406 available from Idemitsu, for example.

상기 정공주입층 표면에 정공수송층(HTL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 정공수송층을 형성한다. 이때, 정공수송층 물질로는 비스(N-(1-나프틸-n-페닐))벤지딘(α-NPD), N,N'-다이(나프탈렌-1-일)-N,N'-바이페닐-벤지딘(NPB) 또는 N,N'-바이페닐-N,N'-비스(3-메틸페닐)-1,1'-바이페닐-4,4'-다이아민(TPD)을 예로 들 수 있다.A hole transport layer (HTL) material is vacuum-deposited or spin coated on the surface of the hole injection layer by a conventional method to form a hole transport layer. In this case, as the hole transport layer material, bis (N- (1-naphthyl-n-phenyl)) benzidine (α-NPD), N, N'-di (naphthalen-1-yl) -N, N'-biphenyl -Benzidine (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD).

상기 정공수송층 표면에 발광층(EML) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 발광층을 형성한다. 이때, 사용되는 발광층 물질 중 단독 발광물질 또는 발광 호스트 물질은 녹색의 경우 본 발명의 유기발광화합물이 인광 녹색 호스트 물질로 사용될 수 있으며, 이 밖에 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)가, 청색의 경우 Balq(8-하이드록시퀴놀린베릴륨염), DPVBi(4,4'-비스(2,2-바이페닐에테닐)-1,1'-바이페닐)계열, 스파이로(Spiro)물질, 스파이로-DPVBi(스파이로-4,4'-비스(2,2-바이페닐에테닐)-1,1'-바이페닐), LiPBO(2-(2-벤조옥사졸릴)-페놀 리튬염), 비스(바이페닐비닐)벤젠, 알루미늄-퀴놀린 금속착체, 이미다졸, 티아졸 및 옥사졸의 금속착체 등이 있다.A light emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, in the case of green light emitting material, the organic light emitting compound of the present invention may be used as a phosphorescent green host material, and in addition to tris (8-hydroxyquinolinolato) aluminum (Alq3). ) Is blue, Balq (8-hydroxyquinolineberyllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl) series, Spiro Substance, Spiro-DPVBi (Spyro-4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzooxazolyl) -phenol Lithium salts), bis (biphenylvinyl) benzene, aluminum-quinoline metal complexes, metal complexes of imidazole, thiazole and oxazole, and the like.

발광층 물질 중 발광 호스트와 함께 사용될 수 있는 도펀트(dopant)의 경우 형광 도펀트로서 이데미츠사(Idemitsu)에서 구입 가능한 IDE102, IDE105, 인광 도펀트로는 트리스(2-페닐피리딘)이리듐(III)(Ir(ppy)3), 이리듐(III)비스[(4,6-다이플루오로페닐)피리디나토-N,C-2']피콜린산염(FIrpic) (참조문헌[Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084]), 플라티늄(II)옥타에틸포르피린(PtOEP), TBE002(코비온사) 등을 사용할 수 있다.In the case of a dopant which can be used together with a light emitting host in the light emitting layer material, IDE102, IDE105, which is available from Idemitsu as a fluorescent dopant, and tris (2-phenylpyridine) iridium (III) (Ir (ppy) as a phosphorescent dopant. 3), iridium (III) bis [(4,6-difluorophenyl) pyridinato-N, C-2 '] picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys Lett., 2001, 79, 3082-3084], platinum (II) octaethyl porphyrin (PtOEP), TBE002 (Kobiion Co.) and the like can be used.

상기 발광층 표면에 전자수송층(ETL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 전자수송층을 형성한다. 이때, 사용되는 전자수송층 물질의 경우 특별히 제한되지 않으며, 바람직하게는 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)을 사용할 수 있다.An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the electron transporting material to be used is not particularly limited, and tris (8-hydroxyquinolinolato) aluminum (Alq3) can be preferably used.

선택적으로는, 발광층과 전자수송층 사이에 정공차단층(HBL)을 추가로 형성하고 발광층에 인광 도펀트를 함께 사용함으로써, 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지할 수 있다. Alternatively, by further forming a hole blocking layer (HBL) between the light emitting layer and the electron transporting layer and using a phosphorescent dopant together with the light emitting layer, it is possible to prevent the phenomenon that the triplet excitons or holes are diffused into the electron transporting layer.

정공차단층의 형성은 정공차단층 물질을 통상적인 방법으로 진공 열증착 및 스핀 코팅하여 실시할 수 있으며, 정공차단층 물질의 경우 특별히 제한되지는 않으나, 바람직하게는 (8-하이드록시퀴놀리놀라토)리튬(Liq), 비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄비페녹사이드(BAlq), 바쏘쿠프로인 (bathocuproine, BCP) 및 LiF 등을 사용할 수 있다.The hole blocking layer can be formed by vacuum thermal deposition and spin coating using a hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, there is no particular limitation, but (8-hydroxyquinolinolato Lithium biphenoxide (BAlq), bathocuproine (BCP), LiF, etc. may be used as the lithium salt (Li), bis (8-hydroxy-2-methylquinolinonato)

상기 전자수송층 표면에 전자주입층(EIL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 전자주입층을 형성한다. 이때, 사용되는 전자주입층 물질의 경우 특별히 제한되지 않으며, 바람직하게는 LiF, Liq, Li2O, BaO, NaCl, CsF 등의 물질을 사용할 수 있다.An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the material of the electron injection layer to be used is not particularly limited, and preferably materials such as LiF, Liq, Li2O, BaO, NaCl, and CsF can be used.

마지막으로, 상기 전자주입층 표면에 음극용 물질을 통상적인 방법으로 진공 열증착하여 음극을 형성한다.Finally, a negative electrode is formed on the surface of the electron injecting layer by vacuum thermal deposition using a conventional method.

이때, 사용되는 음극용 물질로는 리튬(Li), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘(Mg), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 사용될 수 있다. 또한, 전면발광 유기전기발광소자의 경우 산화인듐주석(ITO) 또는 산화인듐아연(IZO)를 사용하여 빛이 투과할 수 있는 투명한 음극을 형성할 수도 있다.At this time, as the negative electrode material to be used, lithium, aluminum, aluminum-lithium, calcium, magnesium, (Mg-Ag) or the like may be used. In the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode capable of transmitting light.

본 발명에 따른 유기 전계발광 소자는 상술한 바와 같은 순서, 즉 양극/정공주입층/정공수송층/발광층/정공차단층/전자수송층/전자주입층/음극 순으로 제조하여도 되고, 그 반대로 음극/전자주입층/전자수송층/정공차단층/발광층/정공수송층/정공주입층/양극의 순서로 제조하여도 무방하다.The organic electroluminescent device according to the present invention may be manufactured in the order as described above, that is, in the order of anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode, Electron injection layer / electron transporting layer / hole blocking layer / light emitting layer / hole transporting layer / hole injecting layer / anode.

이하에서, 본 발명의 화합물들의 합성방법을 대표적인 예를 들어 하기에 설명한다. 그러나, 본 발명의 화합물들의 합성방법이 하기 예시된 방법으로 한정되는 것은 아니며, 본 발명의 화합물들은 하기에 예시된 방법과 이 분야의 공지의 방법에 의해 제조될 수 있다.Hereinafter, a method of synthesizing the compounds of the present invention will be described with reference to representative examples. However, the method of synthesizing the compounds of the present invention is not limited to the following exemplified methods, and the compounds of the present invention can be produced by the methods exemplified below and by methods known in the art.

화합물 [1]의 제조Preparation of compound [1]

[반응식 1][Reaction Scheme 1]

Figure pat00088
Figure pat00088

중간체 화합물 [1-1]의 제조Preparation of intermediate compound [1-1]

1,4-비스(4,4,5,5-테트라메틸-1,3.2-디옥사보로란-2-일)벤젠 50 g(151.5mmol), 1-브로모-2-니트로벤젠 61.2 g(303mmol)을 1,4-디옥산500 mml로 녹이고 질소기류 하에서 테트라키스(트리페닐포스핀)팔라듐 3.5 g(3.03mmol), 탄산칼슘 31.4 g(227.25mmol), 정제수 50 ml로 12시간 동안 환류교반시킨다. 반응종결 후 실온까지 천천히 냉각한 다음 정제수에 부어 고체화 시킨다. 여과된 고체는 정제수와 메탄올로 세척하여 노란색 고체상태의 중간체 화합물 [1-1]34.9 g(72%)을 수득하였다.50 g (151.5 mmol) 1,4-bis (4,4,5,5-tetramethyl-1,3.2-dioxaborolan-2-yl) benzene, 61.2 g 1-bromo-2-nitrobenzene (303mmol) was dissolved in 500 mml of 1,4-dioxane and refluxed under nitrogen stream for 12 hours with 3.5 g (3.03 mmol) of tetrakis (triphenylphosphine) palladium, 31.4 g (227.25 mmol) of calcium carbonate, and 50 ml of purified water. Stir. After completion of the reaction, the mixture was slowly cooled to room temperature and poured into purified water to solidify. The filtered solid was washed with purified water and methanol to give 34.9 g (72%) of the intermediate compound [1-1] as a yellow solid.

중간체 화합물 [1-2], [1-3]의 제조Preparation of Intermediate Compound [1-2], [1-3]

중간체 화합물 [1-1] 34 g(106.15 mmol)을 질소 분위기에서 트리페닐포스핀 55.6g(212.3 mmol), 1,2-디클로로벤젠500 ml에 녹이고 180℃에서 8시간동안 교반시킨다. 반응종결 후 실온까지 냉각한 다음 증류수와 에틸아세테이트를 가하고 층분리하여 유기층을 모은다. 유기층을 무수황산마그네슘으로 건조한 후 여과한다. 여과액을 감압 증류하여 얻은 액체를 컬럼크로마토그래피를 통하여 미색 고체상태의 중간체 화합물 [1-2] 11.4 g(42%), [1-3] 12.2 g(45%)을 수득하였다. 34 g (106.15 mmol) of the intermediate compound [1-1] are dissolved in 55.6 g (212.3 mmol) of triphenylphosphine, and 500 ml of 1,2-dichlorobenzene in a nitrogen atmosphere, followed by stirring at 180 ° C. for 8 hours. After completion of the reaction, the mixture was cooled to room temperature, distilled water and ethyl acetate were added, and the layers were separated to collect an organic layer. The organic layer is dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to obtain 11.4 g (42%) of the intermediate compound [1-2] and 12.2 g (45%) of the intermediate compound [1-2] through column chromatography.

중간체 화합물 [1-4]의 제조Preparation of intermediate compound [1-4]

둥근바닥플라스크에 중간체 화합물 [1-2] 11 g(42.91mmol), 브로모벤젠 8.6 ml(85.83mmol)을 톨루엔250 mml로 녹이고, 질소 분위기에서 팔라듐(II) 아세테이트 96 mg(0.42mmol), 세슘카보네이트 20.9 g(64.36mmol)을 첨가한다. 상온에서 교반시키고 트리-t-부틸포스핀 0.41 ml(0.85mmol)를 적가시키고 반응 온도를 서서히 올리면서 환류교반한다. 반응이 종료되면 에틸아세테이트 1L로 묽히고 포화소금물 1L를 가하여 추출한다. 유기층은 분리하여 무수 황산 마그네슘으로 건조한 후 여과하여 감압 농축 한 다음 디클로로메탄과 메탄올로 재결정화하여 미색 고체의 중간체 화합물 [1-4] 9.6g(68%)을 수득하였다11 g (42.91 mmol) of the intermediate compound [1-2] and 8.6 ml (85.83 mmol) of bromobenzene were dissolved in 250 mml of toluene, and 96 mg (0.42 mmol) of palladium (II) acetate in a nitrogen atmosphere was added to a round bottom flask. 20.9 g (64.36 mmol) of carbonate are added. Stir at room temperature and add 0.41 ml (0.85 mmol) of tri-t-butylphosphine dropwise and stir at reflux while slowly raising the reaction temperature. After the reaction was completed, dilute with 1 L of ethyl acetate, and extract with 1 L of saturated salt. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and recrystallized with dichloromethane and methanol to obtain 9.6 g (68%) of an off-white solid compound [1-4].

중간체 화합물 [1-5]의 제조Preparation of Intermediate Compound [1-5]

둥근바닥플라스크에 4,4'-디브로모-1,1'-바이나프탈렌 40 g(97.05mmol)을 질소 분위기에서 무수테트라하이드로퓨란 2L로 녹이고 -78℃에서 노르말부틸리튬(2.5M) 42.7 ml(106.67 mmol)를 적가시킨다. 동 온도에서 2-클로로-4,6-디페닐-1,3,5-트리아진 25.9 g(97.05 mmol)을 넣은 후 상온으로 온도를 서서히 올린다. 상온에서 증류수와 에틸아세테이트를 가하고 층분리하여 유기층을 모은다. 유기층을 무수황산마그네슘으로 건조한 후 여과한다. 여과액을 감압 증류하여 얻은 액체를 컬럼크로마토그래피를 통하여 흰색 고체 상태의 중간체 화합물 [1-5] 27.9 g(51%)을 수득하였다. In a round bottom flask, 40 g (97.05 mmol) of 4,4'-dibromo-1,1'-binaphthalene was dissolved with 2 L of anhydrous tetrahydrofuran in a nitrogen atmosphere and 42.7 ml of normal butyllithium (2.5M) at -78 ° C. (106.67 mmol) is added dropwise. At the same temperature, 25.9 g (97.05 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was added, and the temperature was gradually raised to room temperature. Distilled water and ethyl acetate are added at room temperature, and the organic layers are collected by layer separation. The organic layer is dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to give 27.9 g (51%) of an intermediate compound [1-5] as a white solid, through column chromatography.

화합물[1]의 제조Preparation of Compound [1]

둥근바닥플라스크에 중간체 화합물[1-4] 5 g(15.04 mmol), 중간체 화합물 [1-4] 10.1 g(18.05 mmol), 구리분말 2.86 g(45.12 mmol), 탄산칼슘 6.23 g(45.12 mmol), 자일렌100ml를 넣고 질소 분위기에서 환류교반한다. 반응 종료 후 상온에서 증류수와 에틸아세테이트를 가하고 층분리하여 유기층을 모은다. 유기층을 무수황산마그네슘으로 건조한 후 여과한다. 디클로로메탄과 메탄올로 재결정화하여 미색 고체의 목적 화합물[1] 7.6 g(62%)을 수득하였다.5 g (15.04 mmol) of intermediate compound [1-4], 10.1 g (18.05 mmol) of intermediate compound [1-4], 2.86 g (45.12 mmol) of copper powder, 6.23 g (45.12 mmol) of calcium carbonate, Add 100 ml of xylene and stir at reflux in a nitrogen atmosphere. After completion of the reaction, distilled water and ethyl acetate were added at room temperature, and the organic layers were collected by layer separation. The organic layer is dried over anhydrous magnesium sulfate and filtered. Recrystallization from dichloromethane and methanol gave 7.6 g (62%) of the title compound [1] as an off-white solid.

화합물 [8]의 제조 Preparation of Compound [8]

[반응식 2] [Reaction Scheme 2]

Figure pat00089
Figure pat00089

중간체 화합물 [8-1]의 제조Preparation of Intermediate Compound [8-1]

반응식 1과 동일한 방법으로 1,4-디클로로-2-니트로벤젠 20 g(104.73mmol), 페난트렌-9-일 보론산 27.9 g(12.56mmol), 테트라키스(트리페닐포스핀)팔라듐 2.42 g(2.09mmol), 탄산칼슘 21.7 g(157.09mmol), 1,4-디옥산, 정제수를 사용하여 흰색 고체상태의 중간체 화합물 [8-1] 21.6 g(62%)을 수득하였다.In the same manner as in Scheme 1, 20 g (104.73 mmol) of 1,4-dichloro-2-nitrobenzene, 27.9 g (12.56 mmol) of phenanthrene-9-yl boronic acid, and 2.42 g of tetrakis (triphenylphosphine) palladium ( 2.09 mmol), 21.7 g (157.09 mmol) of calcium carbonate, 1,4-dioxane, and purified water were used to obtain 21.6 g (62%) of the intermediate compound [8-1] as a white solid.

중간체 화합물 [8-2]의 제조Preparation of Intermediate Compound [8-2]

반응식 1과 동일한 방법으로 중간체 화합물 [8-1] 21 g(62.91 mmol), 트리페닐포스핀33 g(125.83 mmol), 1,2-디클로로벤젠을 사용하여 흰색 고체상태의 중간체 화합물 [8-2] 18.6 g(68%)을 수득하였다.In the same manner as in Scheme 1, intermediate compound [8-1] was obtained as a white solid compound using 21 g (62.91 mmol), 33 g (125.83 mmol) of triphenylphosphine, and 1,2-dichlorobenzene [8-2] 18.6 g (68%) was obtained.

중간체 화합물 [8-3]의 제조Preparation of Intermediate Compound [8-3]

반응식 1과 동일한 방법으로 중간체 화합물 [8-3] 18 g(59.64mmol), 아이오드벤젠 13.3ml(119.29mmol), 팔라듐(II) 아세테이트 267 mg(1.19mmol), 세슘카보네이트 29.1 g(89.64mmol), 톨루엔을 사용하여 노란색 고체상태의 중간체 화합물 [8-3] 14.4 g(64%)을 수득하였다.18 g (59.64 mmol) of intermediate compound [8-3], 13.3 ml (119.29 mmol) of iodinebenzene, 267 mg (1.19 mmol) of palladium (II) acetate, 29.1 g (89.64 mmol) of cesium carbonate Toluene was used to obtain 14.4 g (64%) of the intermediate compound [8-3] in the yellow solid state.

중간체 화합물 [8-4]의 제조Preparation of Intermediate Compound [8-4]

반응식 1과 동일한 방법으로 중간체 화합물 [8-3] 14 g(37.05mmol), (2-니트로페닐)보론산 7.4 g(44.46mmol), 테트라키스(트리페닐포스핀)팔라듐 856 mg(0.74mmol), 탄산칼슘 7.6 g(55.57mmol), 1,4-디옥산, 정제수를 사용하여 흰색 고체상태의 중간체 화합물 [8-4] 12.3 g(72%)을 수득하였다.14 g (37.05 mmol) of an intermediate compound [8-3], 7.4 g (44.46 mmol) of (2-nitrophenyl) boronic acid, and 856 mg (0.74 mmol) of tetrakis (triphenylphosphine) palladium in the same manner as in Scheme 1. , 7.6 g (55.57 mmol) of calcium carbonate, 1,4-dioxane and purified water were used to obtain 12.3 g (72%) of an intermediate compound [8-4] in a white solid state.

중간체 화합물 [8-5], [8-6]의 제조Preparation of Intermediate Compound [8-5], [8-6]

반응식 1과 동일한 방법으로 중간체 화합물 [8-4]12 g(25.83 mmol), 트리페닐포스핀 13.5 g(51.66 mmol), 1,2-디클로로벤젠을 사용하여 흰색 고체상태의 중간체 화합물 [8-5] 4.6 g(40%), [8-6] 4.9 g(42%)을 수득하였다.In the same manner as in Scheme 1, 12 g (25.83 mmol) of an intermediate compound, 13.5 g (51.66 mmol) of triphenylphosphine, and a white solid intermediate compound using 1,2-dichlorobenzene [8-5] ] 4.6 g (40%) and [9-6] 4.9 g (42%).

화합물[8]의 제조Preparation of Compound [8]

반응식 1과 동일한 방법으로 중간체 화합물[8-6] 4.5 g(10.4 mmol), 중간체 화합물[1-5] 7 g(12.48 mmol), 구리분말 1.9 g(30.12 mmol), 탄산칼슘 4.1 g(30.12 mmol), 자일렌을 사용하여 미색 고체의 목적 화합물[8] 6.7 g(71%)을 수득하였다.4.5 g (10.4 mmol) of the intermediate compound [8-6], 7 g (12.48 mmol) of the intermediate compound [1-5], 1.9 g (30.12 mmol) of copper powder, and 4.1 g (30.12 mmol) of calcium carbonate in the same manner as in Scheme 1. Xylene was used to obtain 6.7 g (71%) of the target compound [8] as an off-white solid.

화합물 [17]의 제조Preparation of Compound [17]

[반응식 3] Scheme 3

Figure pat00090
Figure pat00090

중간체 화합물 [17-1]의 제조Preparation of Intermediate Compound [17-1]

반응식 1과 동일한 방법으로 6-브로모-1H-인돌 50 g(255.04mmol), 아이오드벤젠 57ml (510.09mmol), 팔라듐(II) 아세테이트 1.14 g(5.10mmol), 세슘카보네이트 124.6 g(382.56mmol), 톨루엔을 사용하여 흰색 고체상태의 중간체 화합물 [17-1] 47.1 g(68%)을수득하였다.In the same manner as in Scheme 1, 50 g (255.04 mmol) of 6-bromo-1H-indole, 57 ml (510.09 mmol) of iodinebenzene, 1.14 g (5.10 mmol) of palladium (II) acetate, 124.6 g (382.56 mmol) of cesium carbonate Toluene was used to obtain 47.1 g (68%) of an intermediate compound [17-1] in the white solid state.

중간체 화합물 [17-2]의 제조Preparation of Intermediate Compound [17-2]

반응식 1과 동일한 방법으로 중간체 화합물 [17-1] 47 g(172.7 mmol), (2-니트로페닐)보론산 34.5 g(207.2mmol), 테트라키스(트리페닐포스핀)팔라듐 3.99 g(3.45mmol), 탄산칼슘 35.8 g(259.05mmol), 1,4-디옥산, 정제수를 사용하여 흰색 고체상태의 중간체 화합물 [17-2] 38.5 g(71%)을 수득하였다.47 g (172.7 mmol) of an intermediate compound [17-1], 34.5 g (207.2 mmol) of (2-nitrophenyl) boronic acid, and 3.99 g (3.45 mmol) of tetrakis (triphenylphosphine) palladium in the same manner as in Scheme 1. , 35.8 g (259.05 mmol) of calcium carbonate, 1,4-dioxane and purified water were used to obtain 38.5 g (71%) of an intermediate compound [17-2] in a white solid state.

중간체 화합물 [17-3], [17-4]의 제조Preparation of Intermediate Compound [17-3], [17-4]

반응식 1과 동일한 방법으로 중간체 화합물 [17-2] 38.5 g(122.47 mmol), 트리페닐포스핀 64.2 g(244.95 mmol), 1,2-디클로로벤젠을 사용하여 흰색 고체상태의 중간체 화합물 [17-3] 14.1 g(41%), [17-4]14.5 g(42%)을 수득하였다.In the same manner as in Scheme 1, 38.5 g (122.47 mmol) of an intermediate compound, 64.2 g (244.95 mmol) of triphenylphosphine, and a white solid intermediate compound using 1,2-dichlorobenzene [17-3] 14.1 g (41%) and [17-4] 14.5 g (42%) were obtained.

화합물[17]의 제조Preparation of Compound [17]

반응식 1과 동일한 방법으로 중간체 화합물[17-3] 4 g(14.16 mmol), 중간체 화합물[1-5] 9.6 g(17 mmol), 구리분말 2.69g(42.48mmol), 탄산칼슘 5.8 g(42.48 mmol), 자일렌을사용하여 미색 고체의 목적 화합물[17] 7.2 g(67%)을 수득하였다.4 g (14.16 mmol) of the intermediate compound [17-3], 9.6 g (17 mmol) of the intermediate compound [1-5], 2.69 g (42.48 mmol) of copper powder, and 5.8 g (42.48 mmol) of calcium carbonate in the same manner as in Scheme 1. Xylene was used to obtain 7.2 g (67%) of the title compound [17] as an off-white solid.

상기 반응식 1 내지 3의 방법에 따라, 화합물 1 내지 60의 화합물을 제조하였으며, 그 결과를 하기 [제2표군(群)]에 결과를 나타내었다.According to the method of Schemes 1 to 3, compounds of Compounds 1 to 60 were prepared, and the results are shown in the following [Second Table].

[제2표군(群)] [Second group (group)]

Figure pat00091
Figure pat00092
Figure pat00093
Figure pat00094
Figure pat00091
Figure pat00092
Figure pat00093
Figure pat00094

이하에서, 실시예를 통하여 본 발명을 보다 상세히 설명한다. 그러나, 하기의 실시예는 본 발명을 더욱 구체적으로 설명하기 위한 것으로서, 본 발명의 범위가 하기의 실시예에 의하여 한정되는 것은 아니다. 하기의 실시예는 본 발명의 범위 내에서 당업자에 의해 적절히 수정, 변경될 수 있다. Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

비교예 1.Comparative Example 1

하기 화학식 a로 표시되는 화합물을 인광 녹색 호스트로 사용하고, 하기 화학식 c로 표시되는 화합물을 인광 녹색 도판트로 사용하고, 2-TNATA(4,4',4"-tris(N-naphthalen-2-yl)-N-phenylamino)-triphenylamine)을 정공주입층 물질로 사용하고, α-NPD(N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine)을 정공수송층 물질로 사용하여, 다음과 같은 구조를 갖는 유기발광소자를 제작하였다:ITO/2-TNATA(80 nm)/α-NPD(30 nm)/화합물a+화합물c(30 nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm).Using a compound represented by the formula (a) as a phosphorescent green host, using a compound represented by the formula (c) as a phosphorescent green dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2- yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Thus, an organic light emitting device having the following structure was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a + Compound c (30 nm) / Alq 3 (30 nm) / LiF ( 0.5 nm) / Al (60 nm).

애노드는 코닝(Corning)사의 15Ω/cm2(1000Å) ITO 유리기판을 50mm x 50mm x 0.7mm 크기로 잘라서 아세톤, 이소프로필알콜과 순수한 물속에서 각 15분 동안 초음파 세정을 한 후, 30분동안 UV 오존세정을 하여 사용하였다. 상기 기판 상부에 2-TNATA를 진공증착하여 80 nm 두께의 공주입층을 형성하였다. 상기 정공주입층 상부에, α-NPD를 진공 증착하여 30 nm 두께의 정공수송층을 형성하였다. 상기 정공수송층 상부에 화학식 a로 표시되는 화합물 및 화학식 c로 표시되는 화합물(도핑률:10%)를 진공 증착하여 30 nm두께의 발광층을 형성하였다. 이후, 상기 발광층 상부에 Alq3화합물을 30 nm의두께로 진공증착하여 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiF0.5 nm(전자주입층)과 Al 60 nm(캐소드)를 순차적으로 진공증착하여, 표 3에 표시된 바와 같은 유기발광소자를 제조하였다. 이를 비교샘플 1이라고 한다.Anode cuts Corning's 15Ω / cm 2 (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm, ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes, and then UV for 30 minutes. Ozone cleaning was used. 2-TNATA was vacuum-deposited on the substrate to form an 80 nm thick princess deposit layer. On top of the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Chemical Formula a and a compound represented by Chemical Formula c (doping rate: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Thereafter, an Alq 3 compound was vacuum deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in Table 3. This is referred to as Comparative Sample 1.

비교예2.Comparative Example 2

하기 화학식 b로 표시되는 화합물을 인광 녹색 호스트로 사용하고, 하기 화학식 c로 표시되는 화합물을 인광 녹색 도판트로 사용하고, 2-TNATA(4,4',4"-tris(N-naphthalen-2-yl)-N-phenylamino)-triphenylamine)을 정공주입층 물질로 사용하고, α-NPD(N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine)을 정공수송층 물질로 사용하여, 다음과 같은 구조를 갖는 유기발광소자를 제작하였다:ITO/2-TNATA(80 nm)/α-NPD(30 nm)/화합물b+화합물c(30 nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm).Using a compound represented by the formula b as a phosphorescent green host, using a compound represented by the formula c as a phosphorescent green dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2- yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Thus, an organic light emitting device having the following structure was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound b + Compound c (30 nm) / Alq 3 (30 nm) / LiF ( 0.5 nm) / Al (60 nm).

애노드는 코닝(Corning)사의 15Ω/cm2(1000Å) ITO 유리기판을 50mm x 50mm x 0.7mm 크기로 잘라서 아세톤, 이소프로필알콜과 순수한 물속에서 각 15분 동안 초음파 세정을 한 후, 30분 동안 UV 오존세정을 하여 사용하였다. 상기 기판 상부에 2-TNATA를 진공 증착하여 80 nm 두께의 정공주입층을 형성하였다. 상기 정공주입층 상부에, α-NPD를 진공 증착하여 30nm 두께의 정공수송층을 형성하였다. 상기 정공수송층 상부에 화학식 a로 표시되는 화합물 및 화학식 c로 표시되는 화합물(도핑율:10%)을 진공 증착하여 30nm 두께의 발광층을 형성하였다. 이후, 상기 발광층 상부에 Alq3화합물을 30nm의 두께로 진공증착하여 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiF0.5nm(전자주입층)과 Al 60nm(캐소드)를 순차적으로 진공증착하여, 표 3에 표시된 바와 같은 유기발광소자를 제조하였다. 이를 비교샘플 2라고 한다.Anode cuts Corning's 15Ω / cm 2 (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm, ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes, and then UV for 30 minutes. Ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Chemical Formula a and a compound represented by Chemical Formula c (doping rate: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Thereafter, the Alq 3 compound was vacuum-deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum deposited on the electron transport layer to prepare an organic light emitting device as shown in Table 3. This is called comparison sample 2.

Figure pat00095
Figure pat00095

실시예1~56.Examples 1 to 56.

상기 비교예 1 중에서, 발광층 인광 호스트 화합물 a 대신 상기 합성예에 개시된 화학식 1~60으로 표시되는 화합물들을 인광 녹색 호스트 화합물로 각각 이용한 것을 제외하고는 상기 비교예 1과 동일한 방법으로 ITO/2-TNATA(80 nm)/α-NPD(30 nm)/[인광 녹색 호스트 화합물 1~60 중 하나+화합물c(10%)](30 nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)의 구조를 갖는 유기발광소자를 제조하였다. 이를 각각 샘플1 내지 60이라고 한다.In Comparative Example 1, ITO / 2-TNATA was used in the same manner as in Comparative Example 1, except that the compounds represented by Chemical Formulas 1 to 60 disclosed in Synthesis Example were used as the phosphorescent green host compounds instead of the emission layer phosphorescent host compound a. (80 nm) / α-NPD (30 nm) / [one of phosphorescent green host compounds 1-60 + compound c (10%)] (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al ( An organic light emitting device having a structure of 60 nm) was prepared. These are referred to as samples 1 to 60, respectively.

평가예1: 비교샘플1, 2 및 샘플 1~60의 발광 특성평가Evaluation Example 1: Evaluation of Luminescence Characteristics of Comparative Samples 1 and 2 and Samples 1 to 60

비교샘플 1, 2 및 샘플 1~56에대하여, Keithleysourcemeter"2400", KONIKA MINOLTA "CS-2000"을 이용하여 발광휘도, 발광효율, 발광피크를 각각 평가하여, 그 결과를 하기 [제3표군(群)]에 나타내었다. 상기 샘플들은 511~517nm 범위에서 녹색 발광피크값을 보여주었다.For Comparative Samples 1, 2, and 1 to 56, Keithleysourcemeter "2400" and KONIKA MINOLTA "CS-2000" were used to evaluate the luminous intensity, luminous efficiency, and luminous peak, respectively. Viii). The samples showed green emission peaks in the range of 511-517 nm.

[제3표군(群)] [Group 3]

Figure pat00096
Figure pat00097
Figure pat00098
Figure pat00096
Figure pat00097
Figure pat00098

상기 [제3표군(群)]으로부터 확인되는 바와 같이 샘플 1 내지 60은 비교샘플 1, 2에 비하여 향상된 발광 특성을 나타내었다.As confirmed from the above [Third Table], Samples 1 to 60 exhibited improved luminescence properties compared to Comparative Samples 1 and 2.

평가예 2: 비교샘플 1, 2, 및샘플 1 ~ 60의 수명 특성 평가Evaluation Example 2 Evaluation of Life Characteristics of Comparative Samples 1, 2, and 1 to 60

비교샘플 1, 2 및 샘플 1 ~ 60에대하여, ENC technology사의 LTS-1004AC 수명측정장치를 이용하여 3000 nit를 기준으로 수명이 97%에 도달하는 시간을 각각측정하여, 그 결과를 하기 [제4표군(群)]에 나타내었다.For Comparative Samples 1 and 2 and Samples 1 to 60, the time at which the life reached 97% based on 3000 nits was measured using the LTS-1004AC life measuring device manufactured by ENC technology. Table group (群)] is shown.

[제4표군(群)] [Group 4]

Figure pat00099
Figure pat00100
Figure pat00101
Figure pat00099
Figure pat00100
Figure pat00101

상기 [제4표군(群)]로부터 확인되는 바와 같이 샘플 1 내지 56은 비교샘플 1, 2에 비하여 향상된 수명 특성을 나타내었다.As confirmed from the above [Table 4], Samples 1 to 56 showed improved life characteristics compared to Comparative Samples 1 and 2.

Claims (8)

하기 화학식 1로 표시되는 유기발광화합물:
[화학식1]
Figure pat00102

상기 식에서,
X는
Figure pat00103
,
Figure pat00104
,
Figure pat00105
,
Figure pat00106
,
Figure pat00107
,
Figure pat00108
,
Figure pat00109
,
Figure pat00110
,
Figure pat00111
,
Figure pat00112
,
Figure pat00113
,
Figure pat00114
,
Figure pat00115
,
Figure pat00116
,
Figure pat00117
,
Figure pat00118
,
Figure pat00119
,
Figure pat00120
,
Figure pat00121
,
Figure pat00122
,
Figure pat00123
,
Figure pat00124
,
Figure pat00125
,
Figure pat00126
,
Figure pat00127
,
Figure pat00128
또는
Figure pat00129
이며, 상기에서 W는 질소원자, 산소원자, 황원자 또는 Si(C1~C5의 알킬)2이며, R1은 각각 독립적으로 페닐, 피롤, 피라졸, 이미다졸, 트리아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐 또는 나프틸기이며, W가 산소원자, 황원자 또는 Si(C1~C5의 알킬)2인 경우에 R1은 부존재하며;
Y는 질소 또는 탄소원자이며, Y 중 적어도 하나는 질소원자이며;
n은 0 또는 1이며;
R2 내지 R5는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3또는 Si(CH3)3이거나,
중수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3,Si(CH3)3,페닐, 바이페닐, 나프틸, 페난트레닐, 플루오레닐, 피롤, 피라졸, 이미다졸, 트리아졸, 옥사졸, 옥사디아졸, 티오페닐, 티아졸, 티아디아졸, 피라지닐, 피리다지닐 피리디닐, 피리미디닐 및 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 탄소수 6~30의 아릴기 또는 탄소수 5~60의 헤테로아릴기이다.An organic light-emitting compound represented by the following formula (1):
[Chemical Formula 1]
Figure pat00102

In this formula,
X is
Figure pat00103
,
Figure pat00104
,
Figure pat00105
,
Figure pat00106
,
Figure pat00107
,
Figure pat00108
,
Figure pat00109
,
Figure pat00110
,
Figure pat00111
,
Figure pat00112
,
Figure pat00113
,
Figure pat00114
,
Figure pat00115
,
Figure pat00116
,
Figure pat00117
,
Figure pat00118
,
Figure pat00119
,
Figure pat00120
,
Figure pat00121
,
Figure pat00122
,
Figure pat00123
,
Figure pat00124
,
Figure pat00125
,
Figure pat00126
,
Figure pat00127
,
Figure pat00128
or
Figure pat00129
Wherein W is a nitrogen atom, an oxygen atom, a sulfur atom or Si (alkyl of C1 ~ C5) 2 , and each R1 is independently phenyl, pyrrole, pyrazole, imidazole, triazole, pyridinyl, pyrimidinyl, Is a pyrazinyl, pyridazinyl, triazinyl or naphthyl group, and R 1 is absent when W is an oxygen atom, a sulfur atom or Si (alkyl of C 1 to C 5) 2 ;
Y is nitrogen or a carbon atom and at least one of Y is a nitrogen atom;
n is 0 or 1;
R 2 to R 5 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF 3 or Si (CH 3 ) 3, or
Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups It is a C6-C30 aryl group or C5-C60 heteroaryl group unsubstituted or substituted by the substituent. 제 1 항에 있어서,
상기 탄소수 6~30의 아릴 또는 탄소수 5~60의 헤테로아릴기는 페닐, 나프틸, 바이페닐, 바이나프틸, 페난트레닐, 플루오레닐, 피롤, 피라졸, 이미다졸, 트리아졸, 옥사졸, 옥사디아졸, 티오페닐, 티아졸, 티아디아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 벤조티오페닐, 벤즈이미다졸, 벤조옥사졸, 벤즈티아졸, 카바졸, 퀴놀리닐, 이소퀴놀리닐, 인돌 또는 피레닐인 것을 특징으로 하는 유기발광화합물.The method of claim 1,
The aryl having 6 to 30 carbon atoms or the heteroaryl group having 5 to 60 carbon atoms includes phenyl, naphthyl, biphenyl, binaphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, Oxadiazole, thiophenyl, thiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzthiazole, carbazole, An organic light emitting compound, characterized in that it is quinolinyl, isoquinolinyl, indole or pyrenyl. 제 2 항에 있어서,
X는
Figure pat00130
,
Figure pat00131
,
Figure pat00132
,
Figure pat00133
,
Figure pat00134
,
Figure pat00135
,
Figure pat00136
,
Figure pat00137
,
Figure pat00138
,
Figure pat00139
,
Figure pat00140
,
Figure pat00141
,
Figure pat00142
,
Figure pat00143
,
Figure pat00144
,
Figure pat00145
,
Figure pat00146
,
Figure pat00147
,
Figure pat00148
,
Figure pat00149
,
Figure pat00150
,
Figure pat00151
,
Figure pat00152
,
Figure pat00153
,
Figure pat00154
,
Figure pat00155
또는
Figure pat00156
이며, 상기에서 W는 질소원자, 산소원자, 황원자 또는 Si(CH3)2이며, R1은 각각 독립적으로 페닐, 피리디닐 또는 피리미디닐기이며, W가 산소원자, 황원자 또는 Si(CH3)2인 경우에 R1은 부존재하며;
Y는 질소 또는 탄소원자이며, Y 중 적어도 하나는 질소원자이며;
n은 0 또는 1이며;
R2 내지 R5는 수소원자인 것을 특징으로 하는 유기발광화합물.3. The method of claim 2,
X is
Figure pat00130
,
Figure pat00131
,
Figure pat00132
,
Figure pat00133
,
Figure pat00134
,
Figure pat00135
,
Figure pat00136
,
Figure pat00137
,
Figure pat00138
,
Figure pat00139
,
Figure pat00140
,
Figure pat00141
,
Figure pat00142
,
Figure pat00143
,
Figure pat00144
,
Figure pat00145
,
Figure pat00146
,
Figure pat00147
,
Figure pat00148
,
Figure pat00149
,
Figure pat00150
,
Figure pat00151
,
Figure pat00152
,
Figure pat00153
,
Figure pat00154
,
Figure pat00155
or
Figure pat00156
Wherein W is a nitrogen atom, an oxygen atom, a sulfur atom or Si (CH 3 ) 2 , and R 1 is each independently a phenyl, pyridinyl or pyrimidinyl group, and W is an oxygen atom, a sulfur atom or Si (CH 3 ) 2. R 1 is absent;
Y is nitrogen or a carbon atom and at least one of Y is a nitrogen atom;
n is 0 or 1;
R2 to R5 is an organic light emitting compound, characterized in that the hydrogen atom. 제 3 항에 있어서,
상기 유기발광화합물은 화합물 1 내지 화합물 60 중의 어느 하나 인 것을 특징으로 하는 유기발광화합물:
Figure pat00157
Figure pat00158
Figure pat00159
Figure pat00160
The method of claim 3, wherein
The organic light emitting compound is an organic light emitting compound, characterized in that any one of compounds 1 to 60:
Figure pat00157
Figure pat00158
Figure pat00159
Figure pat00160
 제 1 항에 있어서,
상기 유기발광화합물은 유기전기발광소자용 재료 중 인광 녹색 호스트 물질인 것을 특징으로 하는 유기발광화합물.The method of claim 1,
The organic light emitting compound is an organic light emitting compound, characterized in that the phosphorescent green host material of the organic electroluminescent device material. 음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기전기발광소자에 있어서,
상기 유기 박막층 중 적어도 1층 이상이 청구항 1의 유기발광화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자.An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,
Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of claim 1 singly or in combination of two or more. 제 6 항에 있어서,
상기 유기발광화합물이 인광 녹색 호스트 물질로 함유되는 것을 특징으로 하는 유기전기발광소자.The method according to claim 6,
An organic electroluminescent device comprising the organic light emitting compound as a phosphorescent green host material. 제 6 항 또는 제 7 항에 있어서,
상기 유기전기발광소자가
양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 갖는 것을 특징으로 하는 유기전기발광소자.The method according to claim 6 or 7,
The organic electroluminescent device
An organic electroluminescent device comprising a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked in this order.
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