KR100812173B1 - Organic electroluminescent compounds and display device containing the same - Google Patents

Organic electroluminescent compounds and display device containing the same Download PDF

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KR100812173B1
KR100812173B1 KR1020060101641A KR20060101641A KR100812173B1 KR 100812173 B1 KR100812173 B1 KR 100812173B1 KR 1020060101641 A KR1020060101641 A KR 1020060101641A KR 20060101641 A KR20060101641 A KR 20060101641A KR 100812173 B1 KR100812173 B1 KR 100812173B1
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light emitting
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independently
aromatic ring
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신효님
최일원
권혁주
조영준
김봉옥
김성민
윤승수
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(주)그라쎌
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting 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]
    • H10K50/17—Carrier injection layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
    • Y02B20/30—Semiconductor lamps, e.g. solid state lamps [SSL] light emitting diodes [LED] or organic LED [OLED]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract

An organic light emitting material, and an organic light emitting device containing the organic light emitting material are provided to improve the luminous efficiency and lifetime characteristics of a light emitting material and to enhance the drive lifetime of a device. An organic light emitting material is represented by the formula 1, wherein R1 to R3 are independently a phenyl group or a C10-C20 fused polycyclic aromatic ring; and the phenyl group or the C10-C20 fused polycyclic aromatic ring can be substituted with a C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen atom, a C5-C7 cycloalkyl group, a phenyl group or a fused polycyclic aromatic group.

Description

유기 발광 화합물 및 이를 포함하는 표시소자{Organic electroluminescent compounds and display device containing the same}Organic electroluminescent compounds and display device containing the same

도 1은 비교예 1의 발광 효율-전류밀도 특성이고, 1 is a light emission efficiency-current density characteristic of Comparative Example 1,

도 2는 실시예 9의 청색 OLED의 전류밀도-전압 특성이고,2 is a current density-voltage characteristic of the blue OLED of Example 9,

도 3은 실시예 9의 청색 OLED의 발광효율-전류밀도 특성이며, 3 is a light emission efficiency-current density characteristics of the blue OLED of Example 9,

도 4는 비교예 2의 종래의 발광 재료를 적용한 녹색 OLED의 발광 효율-휘도 특성이며,4 is a light emission efficiency-luminance characteristic of the green OLED to which the conventional light emitting material of Comparative Example 2 is applied,

도 5는 실시예 22의 녹색 OLED의 발광효율-전류밀도 특성이고,5 is a light emitting efficiency-current density characteristic of the green OLED of Example 22,

도 6은 실시예 22, 비교예 3 및 비교예 4의 녹색 OLED의 발광효율-전류밀도 특성이며,6 is a light emission efficiency-current density characteristics of the green OLED of Example 22, Comparative Example 3 and Comparative Example 4,

도 7은 실시예 22 및 비교예 2의 녹색 OLED의 색순도 비교 곡선이다.7 is a color purity comparison curve of the green OLEDs of Example 22 and Comparative Example 2. FIG.

본 발명은 하기 화학식 1의 구조를 갖는 유기 발광 화합물 및 이를 이용한 표시소자에 관한 것이다.The present invention relates to an organic light emitting compound having a structure of Formula 1 and a display device using the same.

[화학식 1][Formula 1]

Figure 112006075355432-pat00002
Figure 112006075355432-pat00002

[상기 화학식 1의 R1 내지 R3는 서로 독립적으로 페닐기, C10-C20의 접합 다환 방향족 고리이고, 상기 R1 내지 R3의 페닐기 및 접합 다환 방향족 고리는 C1-C20의 알킬기, C1-C20의 알콕시기, 할로겐기, C5-C7의 시클로알킬기, 페닐기 또는 접합 다환 방향족기가 더 치환될 수 있다.][Wherein R 1 to R 3 of Formula 1 are each independently a phenyl group, a C10-C20 conjugated polycyclic aromatic ring, and the phenyl group and a conjugated polycyclic aromatic ring of R 1 to R 3 are an alkyl group of C1-C20, C1-C20 Alkoxy group, halogen group, C5-C7 cycloalkyl group, phenyl group or conjugated polycyclic aromatic group may be further substituted.]

고효율, 장수명 유기 EL 소자의 개발에 있어서 가장 중요한 요소는 고성능의 발광 재료의 개발이라고 할 수 있다.The most important factor in the development of high-efficiency, long-life organic EL devices is the development of high-performance light emitting materials.

청색 발광은 발광 파장이 장파장 쪽으로 조금만 이동해도 발광 효율 측면에서는 유리해지나, 순청색을 만족시키지 못해 고품위의 디스플레이에는 적용이 쉽지 않은 문제점을 갖고 있으며, 색순도, 효율 및 열안정성의 문제가 있다.Blue light emission is advantageous in terms of light emission efficiency even if the light emission wavelength is slightly shifted toward the long wavelength, but it is not easy to apply to high quality displays because it does not satisfy pure blue color, and there are problems of color purity, efficiency, and thermal stability.

청색 재료의 경우, 유럽공개특허공보 제1063869호 (Idemitsu-Kosan Company Limited)에는 DPVBi(화합물 a)이 공지되어 있고, 이후로 많은 재료들이 개발되어 상업화되어 있으며, 현재까지 효율이 좋다고 알려진 이데미쓰-고산의 디스티릴(distyryl)화합물의 시스템은 파워 효율의 경우, 6 lm/W이고, 소자 수명이 30,000 시간 이상으로 좋기는 하나, 구동 시간에 따른 색순도의 저하로 인하여 풀컬러 디스플레이에 적용했을 때, 수명이 불과 수천시간에 불과하다.In the case of blue materials, European Patent Publication No. 1063869 (Idemitsu-Kosan Company Limited) discloses DPVBi (Compound a), and since then many materials have been developed and commercialized, and until now it is known to have high efficiency. The high-acid distyryl compound system has a power efficiency of 6 lm / W and a device life of 30,000 hours or more, but when applied to a full-color display due to the deterioration of color purity with driving time, Its life is only a few thousand hours.

[화합물 a][Compound a]

Figure 112006075355432-pat00003
Figure 112006075355432-pat00003

한편, 코닥에 의하여 미국등록특허 제6,465,115호에 개시되어 있는 dinaphthylanthracene(화합물 b)의 경우 HTL 물질로 청구된 화합물이지만 청색 발광 재료로서 활용되고 있는 물질로서 이 역시 발광효율과 색순도 측면 등에서 문제가 있다.Meanwhile, in the case of dinaphthylanthracene (compound b) disclosed in US Pat. No. 6,465,115 by Kodak, the compound is used as a HTL material, but also has a problem in terms of luminous efficiency and color purity.

[화합물 b][Compound b]

Figure 112006075355432-pat00004
Figure 112006075355432-pat00004

최근 상기 화합물 b와 유사한 범위들의 발광재료(화합물 c) 유도체들이 LG화 학에 의하여 WO2006/25700호로 공지되었지만 화합물 c 역시 발광효율과 색순도에 한계가 있다.Recently, derivatives of a light emitting material (compound c) similar to those of compound b were known as WO2006 / 25700 by LG Chemical, but compound c also has a limitation in luminous efficiency and color purity.

[화합물 c][Compound c]

Figure 112006075355432-pat00005
Figure 112006075355432-pat00005

한편, 녹색 형광 재료로는 Alq를 호스트로 하여, 도판트로는 쿠마린 유도체(화합물 d, C545T), 퀴나크리돈 유도체(화합물 e), DPT(화합물 f) 등을 수 내지 십수 % 정도로 도핑을 하는 시스템이 개발되어 널리 쓰이고 있다. 그러나, 이들 종래의 발광재료는 초기 발광효율의 경우, 상용화 가능한 수준의 성능을 보이나, 초기 효율 저하가 두드러지며 수명 측면에서 상당한 문제점을 보이고 있어, 대화면의 고성능 패널에서는 채택하기가 힘든 한계를 보이고 있다.On the other hand, as a green fluorescent material, Alq is used as a host, and as a dopant, a doping system of coumarin derivatives (compounds d and C545T), quinacridone derivatives (compound e) and DPT (compound f) is in the range of several to several ten percent. It is developed and widely used. However, these conventional light emitting materials show a commercially available level of performance in the case of the initial luminous efficiency, but the initial efficiency decreases remarkably and shows considerable problems in terms of lifespan. .

이는 호스트로 사용되는 Alq의 양이온성 화학종의 낮은 수명이 원인인 것으로 보고되고 있으며, 이를 극복하기 위하여 양이온성 화학종 및 음이온성 화학종의 안정성을 동시에 갖는 양쪽성 특성의 호스트 개발이 매우 시급한 상황이다.This is reported to be due to the low life of the cationic species of Alq used as a host, and to overcome this situation, it is very urgent to develop a host of amphoteric properties having both stability of cationic species and anionic species. to be.

[화합물 d][Compound d]

Figure 112006075355432-pat00006
Figure 112006075355432-pat00006

[화합물 e][Compound e]

Figure 112006075355432-pat00007
Figure 112006075355432-pat00007

[화합물 f][Compound f]

Figure 112006075355432-pat00008
Figure 112006075355432-pat00008

따라서, 본 발명은 상기한 문제점들을 해결하기 위하여 안출된 것으로서, 본 발명의 목적은 발광 재료 중에서 용매의 역할 또는 에너지 전달자의 역할을 하는 호스트의 특성을 종래의 재료보다 현저히 개선시킨 발광재료를 제공하는 것이며, 또한, 종래의 발광재료에 비하여 발광효율이 개선되며 소자의 수명을 향상시킬 수 있는 청색 및 녹색 발광 재료 및 이를 포함하는 유기발광소자를 제공하는데 발명의 목적이 있다.Accordingly, the present invention has been made to solve the above problems, and an object of the present invention is to provide a light emitting material that significantly improves the characteristics of a host that serves as a solvent or an energy transferer among light emitting materials, compared to conventional materials. Another object of the present invention is to provide a blue and green light emitting material and an organic light emitting device including the same, which can improve light emitting efficiency and improve the lifespan of the device as compared with the conventional light emitting material.

본 발명은 하기 화학식 1의 구조를 갖는 유기재료 및 이를 이용한 표시소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic material having a structure represented by the following Chemical Formula 1 and a display device using the same. The organic light emitting compound according to the present invention has an excellent luminous efficiency and excellent lifespan characteristics of the material to manufacture an OLED device having a very good driving life. There is an advantage to this.

[화학식 1][Formula 1]

Figure 112006075355432-pat00009
Figure 112006075355432-pat00009

[상기 화학식 1의 R1 내지 R3는 서로 독립적으로 페닐기, C10-C20의 접합 다환 방향족 고리이고, 상기 R1 내지 R3의 페닐기 및 접합 다환 방향족 고리는 C1-C20의 알킬기, C1-C20의 알콕시기, 할로겐기, C5-C7의 시클로알킬기, 페닐기 또는 접합 다환 방향족기가 더 치환될 수 있다.][Wherein R 1 to R 3 of Formula 1 are each independently a phenyl group, a C10-C20 conjugated polycyclic aromatic ring, and the phenyl group and a conjugated polycyclic aromatic ring of R 1 to R 3 are an alkyl group of C1-C20, C1-C20 Alkoxy group, halogen group, C5-C7 cycloalkyl group, phenyl group or conjugated polycyclic aromatic group may be further substituted.]

본 발명에서 언급하는 발광재료는 넓게는 제1전극과 제2전극 및 상기 제1전극과 제2전극사이에 개재되는 유기물로 이루어지는 유기발광소자에 있어서, 상기 유기물로 활용되는 것을 모두 포함하는 의미이며, 좁게는 발광층에 있어서 발광매질로서 작용하는 발광호스트에 적용되는 것을 의미한다.The light emitting material referred to in the present invention broadly means an organic light emitting device comprising a first electrode and a second electrode, and an organic material interposed between the first electrode and the second electrode. Narrower means that it is applied to a light emitting host that acts as a light emitting medium in the light emitting layer.

본 발명에 따른 화학식 1 화합물의 R1 내지 R3는 서로 독립적으로 은 구체적으로는 페닐, 나프틸, 안트릴, 플루오레닐, 페난트릴, 플루오란세닐, 파이레닐, 페릴레닐 및 나프타세닐로부터 선택되거나, C1-C20의 알킬기, C1-C20의 알콕시기, 할로겐기, C5-C7의 시클로알킬기, 페닐기 또는 접합 다환 방향족기로 치환된 페닐, 나프틸, 안트릴, 플루오레닐, 페난트릴, 플루오란세닐, 파이레닐, 페릴레닐 및 나프타세닐을 포함하며, 본 발명에 따른 화학식 1의 유기 발광재료는 하기 구조의 화합물로 예시된다.R 1 to R 3 of the compound of formula (I) according to the invention are independently from each other silver, specifically from phenyl, naphthyl, anthryl, fluorenyl, phenanthryl, fluoransenyl, pyrenyl, perrylenyl and naphthacenyl Phenyl, naphthyl, anthryl, fluorenyl, phenanthryl, fluorine selected or substituted with a C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen group, a C5-C7 cycloalkyl group, a phenyl group or a conjugated polycyclic aromatic group Lanshenyl, pyrenyl, peryllenyl and naphthacenyl, wherein the organic light emitting material of formula 1 according to the present invention is exemplified by a compound having the structure

Figure 112006075355432-pat00010
Figure 112006075355432-pat00010

Figure 112006075355432-pat00011
Figure 112006075355432-pat00011

Figure 112006075355432-pat00012
Figure 112006075355432-pat00012

Figure 112006075355432-pat00013
Figure 112006075355432-pat00013

Figure 112006075355432-pat00014
Figure 112006075355432-pat00014

Figure 112006075355432-pat00015
Figure 112006075355432-pat00015

Figure 112006075355432-pat00016
Figure 112006075355432-pat00016

Figure 112006075355432-pat00017
Figure 112006075355432-pat00017

Figure 112006075355432-pat00018
Figure 112006075355432-pat00018

Figure 112006075355432-pat00019
Figure 112006075355432-pat00019

Figure 112006075355432-pat00020
Figure 112006075355432-pat00020

Figure 112006075355432-pat00021
Figure 112006075355432-pat00021

본 발명은 또한 유기발광소자를 제공하며, 본 발명에 따른 유기발광소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기발광소자에 있어서, 상기 유기물층은 하기 화학식 1로 표시되는 화합물을 하나 이상 포함하는 것을 특징으로 한다.The present invention also provides an organic light emitting device, the organic light emitting device according to the present invention comprises a first electrode; Second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one compound represented by Chemical Formula 1 below.

[화학식 1][Formula 1]

Figure 112006075355432-pat00022
Figure 112006075355432-pat00022

[상기 화학식 1의 R1 내지 R3는 서로 독립적으로 페닐기, C10-C20의 접합 다환 방향족 고리이고, 상기 R1 내지 R3의 페닐기 및 접합 다환 방향족 고리는 C1-C20의 알킬기, C1-C20의 알콕시기, 할로겐기, C5-C7의 시클로알킬기, 페닐기 또는 접합 다환 방향족기가 더 치환될 수 있다.][Wherein R 1 to R 3 of Formula 1 are each independently a phenyl group, a C10-C20 conjugated polycyclic aromatic ring, and the phenyl group and a conjugated polycyclic aromatic ring of R 1 to R 3 are an alkyl group of C1-C20, C1-C20 Alkoxy group, halogen group, C5-C7 cycloalkyl group, phenyl group or conjugated polycyclic aromatic group may be further substituted.]

본 발명에 따른 유기발광소자는 상기 유기물층이 발광영역을 포함하며, 상기 발광영역은 상기 화학식 1로 표시되는 하나 이상의 화합물을 발광호스트로 하여 하나 이상의 발광 도판트를 포함하는 것을 특징으로 하며, 본 발명의 유기발광소자에 적용되는 발광 도판트는 특별히 제한되지 않으나 청색의 경우, 하기의 화학식 2 내지 화학식 4에서 선택되는 화합물로 예시될 수 있다.The organic light emitting device according to the present invention is characterized in that the organic material layer includes a light emitting region, and the light emitting region includes at least one light emitting dopant using at least one compound represented by Chemical Formula 1 as a light emitting host. The light emitting dopant applied to the organic light emitting device is not particularly limited, but in the case of blue, it may be exemplified as a compound selected from the following Chemical Formulas 2 to 4.

[화학식 2][Formula 2]

Figure 112006075355432-pat00023
Figure 112006075355432-pat00023

[화학식 3][Formula 3]

Figure 112006075355432-pat00024
Figure 112006075355432-pat00024

[화학식 4][Formula 4]

Figure 112006075355432-pat00025
Figure 112006075355432-pat00025

[상기 화학식 3 또는 화학식 4에서, Ar1 내지 Ar2는 하기의 인데노플루오렌(indenofluorene), 플루오렌(fluorene) 또는 스피로-플루오렌(spiro-fluorene)이 바람직하고; [In Formula 3 or Formula 4, Ar 1 to Ar 2 are preferably indenofluorene, fluorene, or spiro-fluorene;

Figure 112006075355432-pat00026
Figure 112006075355432-pat00027
Figure 112006075355432-pat00028
Figure 112006075355432-pat00026
Figure 112006075355432-pat00027
Figure 112006075355432-pat00028

R11 내지 R16은 독립적으로 C1~C20의 알킬, C1~C5의 알킬이 치환되거나 치환되지 않은 페닐 또는 나프틸에서 선택되며;R 11 to R 16 are independently selected from C 1 to C 20 alkyl, C 1 to C 5 alkyl substituted or unsubstituted phenyl or naphthyl;

Ar3 내지 Ar6는 독립적으로 C5~C20의 방향족 또는 다환방향족 고리에서 선택된다. 단, Ar1와 Ar2가 동일하고, Ar3와 Ar5가 동일하며, Ar4와 Ar6이 동일하다.Ar 3 to Ar 6 are independently selected from C 5 to C 20 aromatic or polycyclic aromatic rings. Provided that Ar 1 and Ar 2 are the same, Ar 3 and Ar 5 are the same, and Ar 4 and Ar 6 are the same;

Figure 112006075355432-pat00029
는
Figure 112006075355432-pat00030
또는
Figure 112006075355432-pat00031
이고,
Figure 112006075355432-pat00029
Is
Figure 112006075355432-pat00030
or
Figure 112006075355432-pat00031
ego,

A와 B는 서로 독립적으로 화학결합이거나

Figure 112006075355432-pat00032
또는
Figure 112006075355432-pat00033
이고,A and B are independently chemical bonds
Figure 112006075355432-pat00032
or
Figure 112006075355432-pat00033
ego,

R17과 R18는 서로 독립적으로 방향족 고리 또는 2개 이상의 방향족 고리가 접합된 접합 다환 방향족 고리이고,R 17 and R 18 are each independently an aromatic ring or a conjugated polycyclic aromatic ring in which two or more aromatic rings are bonded,

R19 내지 R22은 서로 독립적으로 할로겐이 치환되거나 치환되지 않은 직쇄 또는 분지쇄의 C1-C20의 알킬기이고,R 19 to R 22 are each independently a substituted or unsubstituted linear or branched C 1 -C 20 alkyl group,

R23 내지 R26는 서로 독립적으로 수소, 방향족기이고,R 23 to R 26 are each independently hydrogen, an aromatic group,

Ar7 내지 Ar10는 서로 독립적으로 방향족 고리 또는 2개 이상의 방향족 고리가 접합된 접합 다환 방향족 고리이다.]Ar 7 to Ar 10 are each independently an aromatic ring or a conjugated polycyclic aromatic ring in which two or more aromatic rings are bonded.]

상기의 화학식 3 및 화학식 4의 화합물은 구체적으로 하기 구조의 화합물로 예시될 수 있다.The compound of Formula 3 and Formula 4 may be specifically exemplified as a compound having the following structure.

Figure 112006075355432-pat00034
Figure 112006075355432-pat00034

Figure 112006075355432-pat00035
Figure 112006075355432-pat00035

Figure 112006075355432-pat00036
Figure 112006075355432-pat00036

Figure 112006075355432-pat00037
Figure 112006075355432-pat00037

Figure 112006075355432-pat00038
Figure 112006075355432-pat00038

Figure 112006075355432-pat00039
Figure 112006075355432-pat00039

Figure 112006075355432-pat00040
Figure 112006075355432-pat00040

Figure 112006075355432-pat00041
Figure 112006075355432-pat00041

Figure 112006075355432-pat00042
Figure 112006075355432-pat00042

Figure 112006075355432-pat00043
Figure 112006075355432-pat00043

Figure 112006075355432-pat00044
Figure 112006075355432-pat00044

Figure 112006075355432-pat00045
Figure 112006075355432-pat00045

Figure 112006075355432-pat00046
Figure 112006075355432-pat00046

Figure 112006075355432-pat00047
Figure 112006075355432-pat00047

Figure 112006075355432-pat00048
Figure 112006075355432-pat00048

Figure 112006075355432-pat00049
Figure 112006075355432-pat00049

Figure 112006075355432-pat00050
Figure 112006075355432-pat00050

Figure 112006075355432-pat00051
Figure 112006075355432-pat00051

Figure 112006075355432-pat00052
Figure 112006075355432-pat00052

Figure 112006075355432-pat00053
Figure 112006075355432-pat00053

Figure 112006075355432-pat00054
Figure 112006075355432-pat00054

Figure 112006075355432-pat00055
Figure 112006075355432-pat00055

Figure 112006075355432-pat00056
Figure 112006075355432-pat00056

Figure 112006075355432-pat00057
Figure 112006075355432-pat00057

Figure 112006075355432-pat00058
Figure 112006075355432-pat00058

Figure 112006075355432-pat00059
Figure 112006075355432-pat00059

Figure 112006075355432-pat00060
Figure 112006075355432-pat00060

Figure 112006075355432-pat00061
Figure 112006075355432-pat00061

Figure 112006075355432-pat00062
Figure 112006075355432-pat00062

Figure 112006075355432-pat00063
Figure 112006075355432-pat00063

Figure 112006075355432-pat00064
Figure 112006075355432-pat00064

Figure 112006075355432-pat00065
Figure 112006075355432-pat00065

Figure 112006075355432-pat00066
Figure 112006075355432-pat00066

Figure 112006075355432-pat00067
Figure 112006075355432-pat00067

Figure 112006075355432-pat00068
Figure 112006075355432-pat00068

Figure 112006075355432-pat00069
Figure 112006075355432-pat00069

Figure 112006075355432-pat00070
Figure 112006075355432-pat00070

Figure 112006075355432-pat00071
Figure 112006075355432-pat00071

Figure 112006075355432-pat00072
Figure 112006075355432-pat00072

Figure 112006075355432-pat00073
Figure 112006075355432-pat00073

Figure 112006075355432-pat00074
Figure 112006075355432-pat00074

Figure 112006075355432-pat00075
Figure 112006075355432-pat00075

[상기 화학식에서 R19 내지 R22는 메틸기 또는 에틸기이다.][In the formula, R 19 to R 22 is a methyl group or an ethyl group.]

또한, 녹색의 경우, 하기의 화학식 5 내지 화학식 7에서 선택되는 화합물로 예시될 수 있다.In addition, in the case of green, it may be exemplified as a compound selected from the formula

[화학식 5][Formula 5]

Figure 112006075355432-pat00076
Figure 112006075355432-pat00076

[화학식 6][Formula 6]

Figure 112006075355432-pat00077
Figure 112006075355432-pat00077

[화학식 7][Formula 7]

Figure 112006075355432-pat00078
Figure 112006075355432-pat00078

[상기 화학식 6 또는 화학식 7의 R27 및 R28는 서로 독립적으로 2개 이상의 방향족 고리가 접합된 접합 다환 방향족 고리이고, R29 내지 R32는 서로 독립적으로 방향족 고리이며, 상기 R27 내지 R32의 각 방향족 고리는 C1-C20의 알킬기가 더 치환될 수 있다.][R 27 and R 28 in Formula 6 or 7 are independently a conjugated polycyclic aromatic ring in which two or more aromatic rings are bonded to each other, R 29 to R 32 are each independently an aromatic ring, and R 27 to R 32 Each aromatic ring of may be further substituted with an alkyl group of C1-C20.]

상기의 화학식 6 및 화학식 7의 화합물은 구체적으로 하기 구조의 화합물로 예시될 수 있다.The compound of Formula 6 and Formula 7 may be specifically exemplified as a compound having the following structure.

Figure 112006075355432-pat00079
Figure 112006075355432-pat00079

Figure 112006075355432-pat00080
Figure 112006075355432-pat00080

Figure 112006075355432-pat00081
Figure 112006075355432-pat00081

Figure 112006075355432-pat00082
Figure 112006075355432-pat00082

Figure 112006075355432-pat00083
Figure 112006075355432-pat00083

Figure 112006075355432-pat00084
Figure 112006075355432-pat00084

Figure 112006075355432-pat00085
Figure 112006075355432-pat00085

Figure 112006075355432-pat00086
Figure 112006075355432-pat00086

Figure 112006075355432-pat00087
Figure 112006075355432-pat00087

Figure 112006075355432-pat00088
Figure 112006075355432-pat00088

Figure 112006075355432-pat00089
Figure 112006075355432-pat00089

Figure 112006075355432-pat00090
Figure 112006075355432-pat00090

Figure 112006075355432-pat00091
Figure 112006075355432-pat00091

Figure 112006075355432-pat00092
Figure 112006075355432-pat00092

이하에서, 본 발명을 실시예에 의거하여 본 발명에 따른 신규한 유기 발광 화합물의 제조방법을 예시한다. 그러나, 하기의 실시예들은 본 발명에 대한 이해를 돕기 위한 것으로서, 본 발명의 범위가 여기에 국한되는 것은 아니다.Hereinafter, the production method of the novel organic light emitting compound according to the present invention based on the present invention is illustrated. However, the following examples are provided to aid the understanding of the present invention, and the scope of the present invention is not limited thereto.

[제조예] 화학식 1의 화합물의 제조Preparation Example Preparation of Compound of Formula 1

Figure 112006075355432-pat00093
Figure 112006075355432-pat00093

화합물 12의 제조Preparation of Compound 12

9-브로모안트라센(9-Bromoanthracene) (58.3 mmol), 화합물 11의 보로닉 산 유도체 (70.0 mmol), 테트라키스 팔라듐(0) 트리페닐포스핀(Pd(PPh3)4) (5.8 mmol)을 톨루엔:에탄올(부피비2:1)의 혼합용액에 녹인 다음, 2M 탄산나트륨수용액을 넣고 120℃에서 5시간 동안 환류 교반하였다. 그런 다음 온도를 25℃로 낮추고 증류 수를 가해 반응을 종료하고, 에틸아세테이트로 추출, 감압 건조하여 테트라히드로퓨란와 메탄올로 재결정하여 화합물 12를 얻었다.9-Bromoanthracene (58.3 mmol), a boronic acid derivative of compound 11 (70.0 mmol), tetrakis palladium (0) triphenylphosphine (Pd (PPh 3 ) 4 ) (5.8 mmol) After dissolving in a mixed solution of toluene: ethanol (volume ratio 2: 1), 2M sodium carbonate solution was added thereto, and the mixture was stirred under reflux at 120 ° C. for 5 hours. Then, the temperature was lowered to 25 ° C., distilled water was added to terminate the reaction, extracted with ethyl acetate, dried under reduced pressure, and recrystallized with tetrahydrofuran and methanol to obtain compound 12 .

화합물 13의 제조Preparation of Compound 13

상기에서 얻은 화합물 12 (46.0 mmol), N-브로모쑥시니이미드(N-bromosuccinimide) (50.6 mmol)을 질소기류하에서 디클로로메탄에 녹인 다음 25℃에서 5시간 동안 교반하였다. 그런 다음 증류수를 가해 반응을 종료하고 디클로로메탄로 추출, 감압 건조하여 테트라히드로퓨란와 메탄올로 재결정하여 화합물 13을 얻었다.Compound 12 (46.0 mmol), N obtained in the above-the-bromo mossuk siniyi imide (N -bromosuccinimide) (50.6 mmol) and stirred for 5 hours and then 25 ℃ dissolved in dichloromethane in a nitrogen atmosphere. Then, distilled water was added to terminate the reaction. The mixture was extracted with dichloromethane, dried under reduced pressure, and recrystallized with tetrahydrofuran and methanol to obtain compound 13 .

화합물 2의 제조Preparation of Compound 2

상기에서 얻어진 화합물 13 (39.0 mmol)을 질소 기류 하에서 깨끗이 정제한 테트라히드로퓨란에 녹인 다음 -78℃로 냉각, 여기에 n-부틸리튬(1.6M in Hexane) (46.8 mmol)을 천천히 적가한 후 1시간 동안 교반하였다. 그리고 2-이소프로폭시-4,4,5,5-테트라메틸-1,3,2-디옥사보로레인(2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (78.0 mmol)을 첨가해 주었다. 온도를 천천히 올려 25℃에서 하루동안 교반한 다음, 증류수를 가해 반응을 종료하고 에틸아세테이트로 추출, 감압 건조하여 테트라히드로퓨란와 메탄올로 재결정하여 화합물 2을 얻었다.The obtained compound 13 (39.0 mmol) was dissolved in purified tetrahydrofuran under a stream of nitrogen, cooled to -78 ° C, and n -butyllithium (1.6 M in Hexane) (46.8 mmol) was slowly added dropwise thereto. Stir for hours. And 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ) (78.0 mmol) was added. After slowly raising the temperature and stirring at 25 ° C. for one day, distilled water was added to terminate the reaction. The mixture was extracted with ethyl acetate, dried under reduced pressure, and recrystallized with tetrahydrofuran and methanol to obtain Compound 2 .

화합물 3의 제조Preparation of Compound 3

2-클로로-9,10-안트라퀴논(2-chloro-9,10-anthraquinone) (29.7 mmol), 화합물 2 (35.5 mmol), 테트라키스 팔라듐(0) 트리페닐포스핀(Pd(PPh3)4) (3.0 mmol), 알리퀴트336(aliquat336) (3.0 mmol)을 톨루엔에 녹인 다음 2M 탄산칼륨수용액을 첨가하고 3시간 동안 환류 교반하였다. 그리고 나서 다음 온도를 25℃로 낮추고 증류수를 가해 반응을 종료하고 에틸아세테이트로 추출, 감압 건조하여 메탄올과 테트라히드로퓨란으로 재결정하여 화합물 3을 얻었다.2-chloro-9,10-anthraquinone (29.7 mmol), compound 2 (35.5 mmol), tetrakis palladium (0) triphenylphosphine (Pd (PPh 3 ) 4 ) (3.0 mmol) and aliquat336 (3.0 mmol) were dissolved in toluene, and then 2M aqueous potassium carbonate solution was added and stirred under reflux for 3 hours. Then, the temperature was lowered to 25 ° C., distilled water was added to terminate the reaction, extracted with ethyl acetate, dried under reduced pressure, and recrystallized from methanol and tetrahydrofuran to obtain compound 3 .

화합물 6의 제조Preparation of Compound 6

화합물 4 또는 5의 브로모화합물 (54.3 mmol)에 테트라히드로퓨란를 넣고 25oC에서 10분 교반하여 완전히 녹이고 -72℃로 온도를 낮춘 후, n-브틸리튬(2.5M in Hexane) (65.1 mmol)를 천천히 적가하였다. 1 시간 뒤, 화합물 3 (21.7 mmol)을 가한 후, 천천히 25℃로 온도를 올려 26시간 교반하였다. 포화된 암모늄클로라이드 수용액을 가해 1시간 교반 후 감압 여과한 후 유기층을 분리, 증발시켜 화합물 6을 얻었다.Add tetrahydrofuran to a bromo compound (54.3 mmol) of compound 4 or 5 , stir for 10 minutes at 25 ° C., completely dissolve and lower the temperature to -72 ° C., and then n -butyllithium (2.5 M in Hexane) (65.1 mmol) Was slowly added dropwise. After 1 hour, Compound 3 (21.7 mmol) was added, and the temperature was slowly raised to 25 ° C. and stirred for 26 hours. Saturated aqueous ammonium chloride solution was added thereto, stirred for 1 hour, filtered under reduced pressure, and the organic layer was separated and evaporated to obtain Compound 6 .

화합물 1의 제조Preparation of Compound 1

상기에서 얻은 화합물 6 (21.7 mmol), 포타슘아이오다이드(KI) (86.8 mmol), 쏘듐포스페이트모노하이드레이트(NaH2PO2·H2O) (130.2 mmol)을 아세트산에 녹이고 환류 교반하였다. 21시간 후 25℃로 냉각한 후 물을 넣고 저어준 다음 생성된 고체 를 여과하였다. 얻은 고체를 차례로 메탄올, 에틸아세테이트, 테트라히드로퓨란으로 씻어 주어 연한 아이보리 색을 띤 목표화합물 1을 얻었다. Compound 6 (21.7 mmol), potassium iodide (KI) (86.8 mmol) and sodium phosphate monohydrate (NaH 2 PO 2 H 2 O) (130.2 mmol) obtained above were dissolved in acetic acid and stirred under reflux. After 21 hours, the mixture was cooled to 25 ° C., stirred with water, and the resulting solid was filtered. The obtained solid was washed with methanol, ethyl acetate, and tetrahydrofuran in order to obtain the target compound 1 which was light ivory-colored.

[제조예 1] 화합물 301의 제조Preparation Example 1 Preparation of Compound 301

Figure 112006075355432-pat00094
Figure 112006075355432-pat00094

화합물 300의 제조Preparation of Compound 300

9-브로모안트라센(9-Bromoanthracene) 15.0 g(58.3 mmol), 화합물 200의 페닐보로닉 산(phenylboronic acid) 8.5 g(70.0 mmol), 테트라키스 팔라듐(0) 트리페닐포스핀(Pd(PPh3)4) 6.7 g(5.8 mmol)을 톨루엔 300 mL와 에탄올 150 mL에 녹인 다음, 2M 탄산나트륨수용액 145 mL을 넣고 120℃에서 5시간 동안 환류 교반하였다. 그런 다음 온도를 25℃로 낮추고 증류수 150 mL를 가해 반응을 종료하고, 에틸아세테이트 200 mL로 추출, 감압 건조하여 테트라히드로퓨란 20 mL와 메탄올 300 mL로 재결정, 목표화합물 300 12.0 g(47.2 mmol)을 얻었다.15.0 g (58.3 mmol) of 9-Bromoanthracene, 8.5 g (70.0 mmol) of phenylboronic acid of compound 200 , tetrakis palladium (0) triphenylphosphine (Pd (PPh) 3 ) 4 ) 6.7 g (5.8 mmol) was dissolved in 300 mL of toluene and 150 mL of ethanol. Then, 145 mL of 2M aqueous sodium carbonate solution was added thereto, and the mixture was stirred under reflux at 120 ° C. for 5 hours. Then, the temperature was lowered to 25 ° C., 150 mL of distilled water was added to terminate the reaction, extracted with 200 mL of ethyl acetate, dried under reduced pressure, recrystallized from 20 mL of tetrahydrofuran and 300 mL of methanol, and the title compound 300 (12.0 g, 47.2 mmol) was added. Got it.

화합물 400의 제조Preparation of Compound 400

화합물 300 11.7 g(46.0 mmol), N-브로모쑥시니이미드(N-bromosuccinimide) 9.0 g(50.6 mmol)을 질소기류하에서 디클로로메탄 360 mL에 녹인 다음 25℃에서 5시간 동안 교반하였다. 그런 다음 증류수 300 mL를 가해 반응을 종료하고 디클로로메탄 200 mL로 추출, 감압 건조하여 테트라히드로퓨란 20 mL와 메탄올 200 mL로 재결정, 목표화합물 400 13.0 g(39.0 mmol)을 얻었다.Compound 300 11.7 g (46.0 mmol), N - bromo mossuk siniyi the imide (N -bromosuccinimide) 9.0 g (50.6 mmol) and stirred for 5 hours and then 25 ℃ dissolved in 360 mL of dichloromethane in a nitrogen atmosphere. Then, 300 mL of distilled water was added to terminate the reaction. The mixture was extracted with 200 mL of dichloromethane, dried under reduced pressure, and recrystallized with 20 mL of tetrahydrofuran and 200 mL of methanol to obtain 13.0 g (39.0 mmol) of the target compound 400 .

화합물 500의 제조Preparation of Compound 500

화합물 400 13.0 g(39.0 mmol)을 질소기류하에서 깨끗이 정제한 테트라히드로퓨란 200 mL에 녹인다음 -78℃로 냉각, 여기에 n-브틸리튬(1.6M in Hexane) 29.3 mL(46.8 mmol)을 천천히 적가한 후 1시간 동안 교반하였다. 그리고 2-이소프로폭시-4,4,5,5-테트라메틸-1,3,2-디옥사보로레인(2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 15.9 mL (78.0 mmol)을 첨가해 주었다. 온도를 천천히 올려 25℃에서 하루동안 교반한 다음, 증류수 200 mL를 가해 반응을 종료하고 에틸아세테이트 300 mL로 추출, 감압 건조하여 테트라히드로퓨란 20 mL와 메탄올 200 mL로 재결정, 목표화합물 500 13.5 g(35.5 mmol)을 얻었다.Dissolve 1400 g (39.0 mmol) of Compound 400 in 200 mL of purified tetrahydrofuran under a stream of nitrogen, then cool to -78 ° C, and slowly add dropwise n -Butyllithium (1.6 M in Hexane) to 29.3 mL (46.8 mmol). After stirring for 1 hour. And 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ) 15.9 mL (78.0 mmol) was added. After slowly raising the temperature and stirring at 25 ° C. for one day, 200 mL of distilled water was added to terminate the reaction, followed by extraction with 300 mL of ethyl acetate, drying under reduced pressure, recrystallization from 20 mL of tetrahydrofuran and 200 mL of methanol, and 13.5 g of the target compound 500 ( 35.5 mmol).

화합물 600의 제조Preparation of Compound 600

2-클로로-9,10-안트라퀴논(2-chloro-9,10-anthraquinone) 7.2 g(29.7 mmol), 화합물 500 13.5 g(35.5 mmol), 테트라키스 팔라듐(0) 트리페닐포스핀(Pd(PPh3)4) 3.5 g(3.0 mmol), 알리퀴트336(aliquat336) 1.4 mL(3.0 mmol)을 톨루엔 300 mL에 녹인 다음 2M 탄산칼륨수용액 150 mL을 첨가하고 3시간 동안 환류 교반하였다. 그리고 나서 다음 온도를 25℃로 낮추고 증류수 100 mL를 가해 반응을 종료하고 에틸아세테이트 200 mL로 추출, 감압 건조하여 메탄올 200 mL, 테트라히드로퓨란 50 mL로 재결정, 목표화합물 600 10.0 g(21.7 mmol)을 얻었다.7.2 g (29.7 mmol) of 2-chloro-9,10-anthraquinone, Compound 500 13.5 g (35.5 mmol), tetrakis palladium (0) triphenylphosphine (Pd ( PPh 3 ) 4 ) 3.5 g (3.0 mmol) and 1.4 mL (3.0 mmol) of aliquat336 were dissolved in 300 mL of toluene, 150 mL of 2M potassium carbonate solution was added thereto, and the mixture was stirred under reflux for 3 hours. Then, lower the temperature to 25 ° C, add 100 mL of distilled water to terminate the reaction, extract with 200 mL of ethyl acetate, dry under reduced pressure, recrystallize with 200 mL of methanol, 50 mL of tetrahydrofuran, and 10.0 g (21.7 mmol) of the target compound 600 . Got it.

화합물 700의 제조Preparation of Compound 700

2-브로모나프탈렌(2-Bromonaphthalene) 11.2 g(54.3 mmol)에 테트라히드로퓨란 250 mL를 넣고 25℃에서 10분 교반하여 완전히 녹이고 -72℃로 온도를 낮춘 후, n-브틸리튬(2.5M in Hexane) 26.0 mL(65.1 mmol)를 천천히 적가하였다. 1 시간 뒤, 화합물 600 10.0 g(21.7 mmol)을 가한 후, 천천히 25℃로 온도를 올려 26시간 교반하였다. 포화된 암모늄클로라이드 수용액을 가해 1시간 교반 후 감압 여과한 후 유기층을 분리, 증발시켜 목표화합물 700 15.6 g(21.7 mmol)을 얻었다.250 mL of tetrahydrofuran was added to 11.2 g (54.3 mmol) of 2-bromonaphthalene, stirred at 25 ° C. for 10 minutes to completely dissolve the temperature, and cooled to −72 ° C., followed by n -butyllithium (2.5 M in Hexane) 26.0 mL (65.1 mmol) was slowly added dropwise. After 1 hour, 10.0 g (21.7 mmol) of Compound 600 was added, and the temperature was slowly increased to 25 ° C. and stirred for 26 hours. Saturated aqueous ammonium chloride solution was added thereto, stirred for 1 hour, filtered under reduced pressure, and the organic layer was separated and evaporated to obtain 15.6 g (21.7 mmol) of the target compound 700 .

화합물 101의 제조Preparation of Compound 101

화합물 700 15.6 g(21.7 mmol), 포타슘아이오다이드(KI) 14.4 g(86.8 mmol), 쏘듐포스페이트모노하이드레이트(NaH2PO2·H2O) 13.8 g(130.2 mmol)을 아세트산 250 mL에 녹이고 환류 교반하였다. 21시간 후 25℃로 냉각한 후 물을 400 mL넣고 저어 준 다음 생성된 고체를 여과하였다. 얻은 고체를 차례로 메탄올 300 mL, 에틸아세테이트 100 mL, 테트라히드로퓨란 50 mL로 씻어 주어 연한 아이보리 색을 띤 목표화합물 101 10.0 g(68 %)을 얻었다. Dissolve 1700 g (21.7 mmol) of Compound 700 , 14.4 g (86.8 mmol) of potassium iodide (KI), 13.8 g (130.2 mmol) of sodium phosphate monohydrate (NaH 2 PO 2 H 2 O) in acetic acid, and reflux. Stirred. After 21 hours, the mixture was cooled to 25 ° C., 400 mL of water was stirred, and the resulting solid was filtered. The obtained solid was washed sequentially with 300 mL of methanol, 100 mL of ethyl acetate, and 50 mL of tetrahydrofuran to obtain 10.0 g (68%) of light ivory-colored target compound 101 .

1H NMR(CDCl3, 200 MHz) δ = 7.22(m, 1H), 7.32-7.35(m, 12H), 7.48-7.54(m, 5H), 7.67-7.73(m, 13H), 7.89(m, 3H) 1 H NMR (CDCl 3 , 200 MHz) δ = 7.22 (m, 1H), 7.32-7.35 (m, 12H), 7.48-7.54 (m, 5H), 7.67-7.73 (m, 13H), 7.89 (m, 3H)

MS/FAB : 682(found) 682.85(calculated)MS / FAB: 682 (found) 682.85 (calculated)

[제조예 2~36][Manufacture example 2 ~ 36]

상기 제조예 1의 방법을 이용하여 하기 표 1의 유기 발광 화합물을 제조하였으며, 표 2에 제조된 화합물들의 NMR을 나타내었다.Using the method of Preparation Example 1 was prepared an organic light emitting compound of Table 1, it shows the NMR of the compounds prepared in Table 2.

[표 1]TABLE 1

Figure 112006075355432-pat00095
Figure 112006075355432-pat00095

Figure 112006075355432-pat00096
Figure 112006075355432-pat00096

Figure 112006075355432-pat00097
Figure 112006075355432-pat00097

[표 2]TABLE 2

Figure 112006075355432-pat00098
Figure 112006075355432-pat00098

Figure 112006075355432-pat00099
Figure 112006075355432-pat00099

Figure 112006075355432-pat00100
Figure 112006075355432-pat00100

[실시예 1~13] 본 발명에 따른 화합물을 이용한 OLED 소자의 제조Examples 1 to 13 Fabrication of OLED Devices Using Compounds According to the Present Invention

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다.An OLED device having a structure using the light emitting material of the present invention was produced.

우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15 Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다.First, a transparent electrode ITO thin film (15 Ω / □) obtained from an OLED glass (manufactured by Samsung Corning Corporation) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol. It was used after.

다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 하기 구조의 4,4',4"-tris(N,N-(2-naphthyl)- phenylamino)triphenylamine (2-TNATA)을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 2-TNATA를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다.Next, an ITO substrate was installed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2) -TNATA), evacuated until the vacuum in the chamber reached 10 -6 torr, and then applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate.

Figure 112006075355432-pat00101
Figure 112006075355432-pat00101

이어서, 진공 증착 장비 내의 다른 셀에 하기구조 N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.The NPB -diphenyl-4,4'-diamine into the (NPB), by applying a current to the cell - Then, to another cell of the vacuum vapor-deposit device structure, N, N 'N, N -bis (α-naphthyl)' A 20 nm thick hole transport layer was deposited on the hole injection layer by evaporation.

Figure 112006075355432-pat00102
Figure 112006075355432-pat00102

정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 본 발명에 따른 화합물(예 : 화합물 321)을 넣고, 또 다른 셀에는 하기 구조의 도판트 재료인 perylene을 각각 넣은 후, 두 물질을 다른 증발 속도로 증발시켜 perylene을 2 내지 5 mol%로 도핑함으로써 상기 정공 전달층 위에 35 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. In one cell of the vacuum deposition equipment, the compound according to the present invention (e.g., compound 321) is put in each cell, and in another cell, the dopant material of the following structure is put in each, and then the two materials are evaporated at different evaporation rates to obtain perylene. A light emitting layer having a thickness of 35 nm was deposited on the hole transport layer by doping to 5 mol%.

Figure 112006075355432-pat00103
Figure 112006075355432-pat00104
Figure 112006075355432-pat00103
Figure 112006075355432-pat00104

이어서 전자전달층으로써 하기 구조의 tris(8-hydroxyquinoline)- aluminum(III)(Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 하기 구조의 화합물 lithium quinolate (리튬 퀴놀레이트, Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다.Subsequently, tris (8-hydroxyquinoline)-aluminum (III) (Alq) having the following structure was deposited as an electron transport layer to a thickness of 20 nm, and then the compound lithium quinolate (liquid quinolate, Liq) having the following structure was used as the electron injection layer. After deposition to a thickness of 2 nm, using a different vacuum deposition equipment to deposit an Al cathode to a thickness of 150 nm to produce an OLED.

Figure 112006075355432-pat00105
Figure 112006075355432-pat00105

OLED 소자에 사용된 각 재료들은, 각각 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each material used in the OLED device was vacuum sublimated and purified under 10 -6 torr, respectively, to be used as an OLED light emitting material.

[실시예 14~26] 본 발명에 따른 화합물을 이용한 OLED 소자의 제조Examples 14 to 26 Fabrication of OLED Devices Using Compounds According to the Present Invention

실시예 1과 동일한 방법으로 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 본 발명에 따른 화합물(예 : 화합물 321)을 넣고, 또 다른 셀에는 하기구조의 Coumarin 545T(C545T)를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 Coumarin 545T(C545T)를 2 내지 5 mol%로 도핑함으로써 상기 정공 전달층 위에 35 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, the light emitting layer was deposited thereon as follows. Put a compound according to the present invention (e.g. Compound 321) in one cell in a vacuum deposition equipment, and put another Coumarin 545T (C545T) of the following structure in another cell, and then evaporate the two materials at different rates to give a Coumarin 545T (C545T) 35 nm thick light emitting layer was deposited on the hole transport layer by doping) at 2 to 5 mol%.

Figure 112006075355432-pat00106
Figure 112006075355432-pat00107
Figure 112006075355432-pat00106
Figure 112006075355432-pat00107

이어서 실시예 1과 동일한 방법으로 전자전달층과 전자주입층을 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다.Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and then another OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

[비교예 1] 종래의 발광 재료를 이용한 OLED 소자의 제조Comparative Example 1 Fabrication of OLED Device Using Conventional Light-Emitting Material

실시예 1과 동일한 방법으로 정공주입층, 정공전달층을 형성시킨 후, 상기 진공 증착 장비의 한쪽 셀에는 청색 발광 재료인 디나프틸안트라센(dinaphthylanthracene(DNA))을 넣고, 다른 셀에 다른 청색 발광 재료인 perylene을 각각 넣은 후, 증착 속도를 100:1 로 하여 상기 정공 전달층 위에 35 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, one cell of the vacuum deposition equipment was placed with dinaphthylanthracene (DNA), a blue light emitting material, and another blue light emission in the other cell. After putting the perylene as a material, a light emitting layer having a thickness of 35 nm was deposited on the hole transport layer at a deposition rate of 100: 1.

Figure 112006075355432-pat00108
Figure 112006075355432-pat00109
Figure 112006075355432-pat00108
Figure 112006075355432-pat00109

이어서 실시예 1과 동일한 방법으로 전자전달층과 전자주입층을 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다.Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and then another OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

[비교예 2] 종래의 발광 재료를 이용한 OLED 소자를 제조Comparative Example 2 An OLED device was manufactured using a conventional light emitting material.

실시예 1과 동일한 방법으로 정공주입층, 정공전달층을 형성시킨 후, 상기 진공 증착 장비 내의 다른 셀에 발광 호스트 재료인 tris(8- hydroxyquinoline)aluminum(III) (Alq)를 넣고, 또 다른 셀에는 Coumarin 545T(C545T)를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 도핑함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다. 이 때의 도핑 농도는 Alq 기준으로 2 내지 5 mol%가 바람직하다.After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, tris (8-hydroxyquinoline) aluminum (III) (Alq), which is a light emitting host material, was placed in another cell in the vacuum deposition apparatus, and another cell In each of the Coumarin 545T (C545T), the light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by evaporating and doping the two materials at different rates. The doping concentration at this time is preferably 2 to 5 mol% based on Alq.

Figure 112006075355432-pat00110
Figure 112006075355432-pat00111
Figure 112006075355432-pat00110
Figure 112006075355432-pat00111

이어서 실시예 1과 동일한 방법으로 전자전달층과 전자주입층을 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다.Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and then another OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

[비교예 3] 종래의 발광 재료를 이용한 OLED 소자의 제조Comparative Example 3 Fabrication of OLED Device Using Conventional Light-Emitting Material

실시예 1과 동일한 방법으로 정공주입층, 정공전달층을 형성시킨 후, 상기 진공 증착 장비 내의 다른 셀에 청색 발광 재료인 dinaphthylanthracene(DNA)를 넣고, 또 다른 셀에는 하기 구조의 Coumarin 545T(C545T)를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 도핑함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다. 이 때의 도핑 농도는 Alq 기준으로 2 내지 5 mol%가 바람직하다.After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, dinaphthylanthracene (DNA), which is a blue light emitting material, was placed in another cell in the vacuum deposition apparatus, and in another cell, the Coumarin 545T (C545T) having the structure After each of the two materials were evaporated and doped at different rates to deposit a 30 nm thick light emitting layer on the hole transport layer. The doping concentration at this time is preferably 2 to 5 mol% based on Alq.

Figure 112006075355432-pat00112
Figure 112006075355432-pat00113
Figure 112006075355432-pat00112
Figure 112006075355432-pat00113

[비교예 4] 종래의 발광 재료를 이용한 OLED 소자의 제조Comparative Example 4 Fabrication of OLED Device Using Conventional Light-Emitting Material

실시예 1과 동일한 방법으로 정공주입층, 정공전달층을 형성시킨 후, 상기 진공 증착 장비 내의 다른 셀에 청색 발광 재료인 하기 구조의 US 20060046097A1특허에 나오는 화합물 A를 넣고, 또 다른 셀에는 하기 구조의 Coumarin 545T(C545T)를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 도핑함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다. 이 때의 도핑 농도는 Alq 기준으로 2 내지 5 mol%가 바람직하다.After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, Compound A in the US 20060046097A1 patent of the following structure, which is a blue light emitting material, was added to another cell in the vacuum deposition equipment, and another cell was Each of Coumarin 545T (C545T) was added, and then the light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by evaporating and doping the two materials at different rates. The doping concentration at this time is preferably 2 to 5 mol% based on Alq.

Figure 112006075355432-pat00114
Figure 112006075355432-pat00115
Figure 112006075355432-pat00114
Figure 112006075355432-pat00115

이어서 실시예 1과 동일한 방법으로 전자전달층과 전자주입층을 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다.Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and then another OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

[실험예 1] 제조된 OLED 소자의 청색 발광 특성Experimental Example 1 Blue Light Emitting Characteristics of the Prepared OLED Device

실시예 1~13과 비교예 1에서 제조된 본 발명에 따른 유기 발광 화합물과 종래의 발광 화합물을 함유하는 OLED 소자의 청색 발광 효율을 각각 500 cd/m2 및 2,000 cd/m2 에서 측정하여 하여 표 3에 나타내었다.The blue light emission efficiency of the organic light emitting compound according to the present invention prepared in Examples 1 to 13 and Comparative Example 1 and the conventional light emitting compound was measured at 500 cd / m 2 and 2,000 cd / m 2 , respectively. Table 3 shows.

[표 3]TABLE 3

Figure 112006075355432-pat00116
Figure 112006075355432-pat00116

상기 표 1은 본 발명의 재료를 청색 발광 소자에 적용한 결과로, 표 1에서 알 수 있는 바와 같이, 본 발명에서의 발광 재료의 발광효율은 저휘도에서 5.26~6.30 cd/A 및 고휘도에서 4.80~5.88 cd/A이나, 비교예 1의 발광효율은 저휘도 및 고휘도에서 각각 4.45 cd/A 및 3.6 cd/A로 본 발명에 따른 유기 발광 화합물을 이용한 발광 소자가 비교예 1 대비 저휘도, 고휘도에서 모두 1.5 cd/A 이상 우수한 결과를 보였다. 특히, 고휘도에서는 화합물 별로 2 cd/A 이상의 개선 효과를 확인할 수 있었다. Table 1 is a result of applying the material of the present invention to a blue light emitting device, as can be seen in Table 1, the luminous efficiency of the light emitting material in the present invention is 5.26 ~ 6.30 cd / A at low brightness and 4.80 ~ at high brightness The luminous efficiency of 5.88 cd / A, but Comparative Example 1 is 4.45 cd / A and 3.6 cd / A at low and high brightness, respectively. The light emitting device using the organic light emitting compound according to the present invention has a lower brightness and higher brightness than Comparative Example 1. All showed excellent results above 1.5 cd / A. In particular, the high brightness was able to confirm the improvement effect of 2 cd / A or more for each compound.

더구나 색순도 측면에서는 본 발명의 호스트 재료를 적용하는 경우, 약간의 개선을 관찰하였으며, 이와 같이 색순도 및 발광 효율이 동시에 개선되는 결과는 본 발명의 재료가 우수한 특성을 가지고 있다는 것을 입증해 주고 있는 것이다.Moreover, in terms of color purity, slight improvement was observed when the host material of the present invention was applied. Thus, the results of simultaneously improving color purity and luminous efficiency prove that the material of the present invention has excellent characteristics.

도 1은 종래의 발광재료인 DNA:perylene를 사용한 비교예 1의 발광 효율-전류밀도 특성을 도시한 곡선이고, 도 2 및 도 3은 본 발명에 따른 화합물 321을 발광재료로 이용한 실시예 9의 청색 OLED의 전류밀도-전압 특성 및 발광효율-전류밀도 특성을 도시한 곡선이다. 도면에서 볼 수 있듯이, 현저한 특성 개선을 확인 할 수 있었다.Figure 1 is a curve showing the luminous efficiency-current density characteristics of Comparative Example 1 using a conventional light emitting material DNA: perylene, Figures 2 and 3 of Example 9 using the compound 321 according to the present invention as a light emitting material A curve showing current density-voltage characteristics and luminous efficiency-current density characteristics of a blue OLED. As can be seen in the drawing, a marked improvement in properties was confirmed.

[실험예 2] 제조된 OLED 소자의 녹색 발광 특성Experimental Example 2 Green Light Emitting Characteristics of the Fabricated OLED Device

실시예 14~26과 비교예 2에서 제조된 본 발명에 따른 유기 발광 화합물과 종래의 발광 화합물을 함유하는 OLED 소자의 녹색 발광 효율을 각각 5,000 cd/m2 및 20,000 cd/m2 에서 측정하여 하여 표 4에 나타내었다.The green light emitting efficiency of the organic light emitting compound according to the present invention prepared in Examples 14 to 26 and Comparative Example 2 and the conventional light emitting compound measured at 5,000 cd / m 2 and 20,000 cd / m 2 Table 4 shows.

[표 4]TABLE 4

Figure 112006075355432-pat00117
Figure 112006075355432-pat00117

상기 표 4는 본 발명의 재료를 녹색 발광 소자에 적용하여 특성을 확인한 결과이다. 실험예 1의 청색 발광 소자와 마찬가지로, 저휘도, 고휘도에서 종래의 발광 재료 대비 월등한 특성을 확인할 수 있었다.Table 4 shows the results of applying the material of the present invention to the green light emitting device to check the characteristics. Similar to the blue light emitting device of Experimental Example 1, it was possible to confirm the superior characteristics of the conventional light emitting material at low brightness and high brightness.

비교예 2의 Alq 호스트 대비 70 % 이상, 비교예 3의 종래의 호스트 대비 40 % 이상의 효율 개선을 확인할 수 있었다. 이는 종래의 녹색 발광 재료의 한계점을 확실하게 극복하여 주는 결과이다. 특히, 고휘도에서의 월등한 성능 개선은 고휘도가 요구되는 대화면용 OLED나, 극한의 특성을 요구하는 2인치급 수동형 OLED 등에서 충분히 상용화 가능한 재료라고 평가할 수 있다.Efficiency improvement of more than 70% compared to Alq host of Comparative Example 2, more than 40% compared to the conventional host of Comparative Example 3. This is a result that reliably overcomes the limitations of the conventional green light emitting material. In particular, the superior performance improvement at high brightness can be evaluated as a material that can be sufficiently commercialized in large-screen OLEDs requiring high brightness, and 2-inch passive OLEDs requiring extreme characteristics.

색좌표 측면에서는 유의차는 없으며, 이렇게 색순도를 유지하면서 발광 효율을 개선시킨 본 발명의 재료는 기존의 재료를 한단계 뛰어 넘는 재료의 세대를 구분하여 주는 발명이라고 할 수 있겠다.There is no significant difference in terms of color coordinates, and thus the material of the present invention which improves luminous efficiency while maintaining color purity can be said to be an invention that distinguishes generations of materials that go beyond existing materials.

도 4는 종래 녹색 발광 재료인 Alq:C545T를 사용한 비교예 2의 발광 소자의 발광 효율-휘도 특성을 도시한 곡선이고, 도 5는 본 발명에 따른 화합물 321을 발광재료로 이용한 실시예 22의 녹색 발광 소자의 발광 효율-전류밀도 특성을 도시한 곡선이고, 도 6은 비교예 3 및 비교예 4의 종래의 발광재료와 본 발명에 따른 화합물 321을 발광재료로 이용한 실시예 22의 녹색 발광 소자의 발광 효율-전류밀도 특성을 도시한 곡선이다.Figure 4 is a curve showing the luminous efficiency-luminance characteristics of the light emitting device of Comparative Example 2 using the conventional green light emitting material Alq: C545T, Figure 5 is a green light of Example 22 using the compound 321 according to the present invention as a light emitting material 6 is a curve illustrating the light emission efficiency-current density characteristics of the light emitting device, and FIG. 6 shows the green light emitting device of Example 22 using the conventional light emitting material of Comparative Example 3 and Comparative Example 4 and the compound 321 according to the present invention as a light emitting material. A curve showing the luminous efficiency-current density characteristics.

특히, 본 발명의 발광 재료는 청색 OLED 및 녹색 OLED에 모두 적용 가능하며, 특성 측면에서 매우 우수한 결과를 보였다. 이러한 결과는 재료의 우수성을 보여주는 매우 두드러진 특성이며, 이러한 특성을 가진 재료의 발명은 OLED 패널 구조의 단순화를 유도함으로써 OLED 제조상의 비용을 낮추는 부수적 효과를 야기할 수 있다. 따라서 상기 우수한 특성으로 인하여 OLED 분야의 발전에 혁신적 결과를 보일 수 있다.In particular, the light emitting material of the present invention is applicable to both the blue OLED and the green OLED, and showed excellent results in terms of characteristics. These results are very prominent properties that show the material's superiority, and the invention of materials with these properties can lead to the side effect of lowering the cost of OLED manufacturing by inducing the simplification of the OLED panel structure. Therefore, due to the excellent properties, it can exhibit innovative results in the development of the OLED field.

도 7은 본 발명에 따른 화합물 321을 발광재료로 이용한 실시예 22의 녹색 발광 소자와 비교예 2의 녹색 발광 소자의 색순도을 비교한 곡선으로, 종래의 순녹색 발광 재료 대비 큰 차이를 보이지 않아 발광색 특성이 좋음을 알 수 있다. 또한 상기 실시예 22의 발광 소자의 EL 스펙트럼은 520 nm의 전형적인 녹색 발광 피크를 확인할 수 있었는데, 이는 청색 발광 특성을 가진 본 발명의 유기 발광 화합물이 매우 우수한 전기적 특성을 갖고 있어, 발광 도판트의 특성을 최대로 끌어낼 수 있는 능력을 가지고 있음을 알 수 있다.7 is a curve comparing the color purity of the green light emitting device of Example 22 and the green light emitting device of Comparative Example 2 using the compound 321 according to the present invention as a light emitting material, it does not show a significant difference compared to the conventional pure green light emitting material characteristics This is good. In addition, the EL spectrum of the light emitting device of Example 22 was able to confirm a typical green light emission peak of 520 nm, which is very good electrical properties of the organic light emitting compound of the present invention having blue light emission characteristics, the characteristics of the light emitting dopant It can be seen that it has the ability to pull up to.

특히, 재료 수명 특성이 종래의 발광 재료 대비 현저히 뛰어남은 종래의 발광 재료의 경우, 즉 전자 전도성이 뛰어난 특성을 갖고 있는 재료 특성과 반대되는 개념의 본 발명 재료가 가질 수 있는 최고의 장점이다.In particular, in the case of a conventional light emitting material having a material life characteristic that is remarkably superior to a conventional light emitting material, that is, the material of the present invention having a concept opposite to that of a material having excellent electronic conductivity is the best advantage.

이러한 특성은 안트라센의 2번 위치에 9-아릴안트릴의 10번 위치를 도입함으로써, 분자간 오비탈의 중첩 효과를 개선시킬 뿐만 아니라, 도판트와의 에너지 준위 관계를 훨씬 유리하게 만들어 주게 되어, 단순한 종래의 9, 10-디아릴안트라센 구조에서의 단점을 획기적으로 보완해주는 것이다.This property not only improves the overlapping effect of intermolecular orbitals, but also makes the energy level relationship with the dopant much more advantageous by introducing the 10-position of 9-arylantryl at position 2 of anthracene. 9, 10-diaryl anthracene structure of the disadvantage will be significantly complemented.

본 발명에 따른 유기 발광 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.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.

Claims (9)

하기 화학식 1로 표시되는 유기 발광재료.An organic light emitting material represented by the following formula (1). [화학식 1][Formula 1]
Figure 112006075355432-pat00118
Figure 112006075355432-pat00118
 [상기 화학식 1의 R1 내지 R3는 서로 독립적으로 페닐기, C10-C20의 접합 다환 방향족 고리이고, 상기 R1 내지 R3의 페닐기 및 접합 다환 방향족 고리는 C1-C20의 알킬기, C1-C20의 알콕시기, 할로겐기, C5-C7의 시클로알킬기, 페닐기 또는 접합 다환 방향족기가 더 치환될 수 있다.][Wherein R 1 to R 3 of Formula 1 are each independently a phenyl group, a C10-C20 conjugated polycyclic aromatic ring, and the phenyl group and a conjugated polycyclic aromatic ring of R 1 to R 3 are an alkyl group of C1-C20, C1-C20 Alkoxy group, halogen group, C5-C7 cycloalkyl group, phenyl group or conjugated polycyclic aromatic group may be further substituted.] 제 1 항에 있어서,The method of claim 1, 상기 화학식 1의 R1 내지 R3는 서로 독립적으로 C1-C20의 알킬기, C1-C20의 알콕시기, 할로겐기, C5-C7의 시클로알킬기, 페닐기 또는 접합 다환 방향족기로 치환되거나 치환되지 않은 페닐, 나프틸, 안트릴, 플루오레닐, 페난트릴, 플루오란세닐, 파이레닐, 페릴레닐 및 나프타세닐로부터 선택되는 것을 특징으로 하는 유기 발광재료.R 1 to R 3 of Formula 1 are each independently substituted or unsubstituted C1-C20 alkyl group, C1-C20 alkoxy group, halogen group, C5-C7 cycloalkyl group, phenyl group or conjugated polycyclic aromatic group An organic light emitting material, characterized in that it is selected from yl, anthryl, fluorenyl, phenanthryl, fluoransenyl, pyrenyl, perylenyl and naphthacenyl. 제 2 항에 있어서,The method of claim 2, 하기 구조의 화합물로부터 선택되는 것을 특징으로 하는 유기 발광재료.An organic light emitting material, characterized in that selected from compounds of the following structure.
Figure 112006075355432-pat00119
Figure 112006075355432-pat00119
Figure 112006075355432-pat00120
Figure 112006075355432-pat00120
Figure 112006075355432-pat00121
Figure 112006075355432-pat00121
Figure 112006075355432-pat00122
Figure 112006075355432-pat00122
Figure 112006075355432-pat00123
Figure 112006075355432-pat00123
Figure 112006075355432-pat00124
Figure 112006075355432-pat00124
Figure 112006075355432-pat00125
Figure 112006075355432-pat00125
Figure 112006075355432-pat00126
Figure 112006075355432-pat00126
Figure 112006075355432-pat00127
Figure 112006075355432-pat00127
Figure 112006075355432-pat00128
Figure 112006075355432-pat00128
Figure 112006075355432-pat00129
Figure 112006075355432-pat00129
Figure 112006075355432-pat00130
Figure 112006075355432-pat00130
 제1전극;A first electrode; 제2전극; 및 Second electrode; And 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기발광소자에 있어서,In the organic light emitting device consisting of one or more organic material layer interposed between the first electrode and the second electrode, 상기 유기물층은 하기 화학식 1로 표시되는 화합물을 하나 이상 포함하는 것을 특징으로 하는 유기발광소자.The organic material layer is an organic light emitting device, characterized in that it comprises one or more compounds represented by the formula (1). [화학식 1][Formula 1]
Figure 112006075355432-pat00131
Figure 112006075355432-pat00131
 [상기 화학식 1의 R1 내지 R3는 서로 독립적으로 페닐기, C10-C20의 접합 다환 방향족 고리이고, 상기 R1 내지 R3의 페닐기 및 접합 다환 방향족 고리는 C1-C20의 알킬기, C1-C20의 알콕시기, 할로겐기, C5-C7의 시클로알킬기, 페닐기 또는 접합 다환 방향족기가 더 치환될 수 있다.][Wherein R 1 to R 3 of Formula 1 are each independently a phenyl group, a C10-C20 conjugated polycyclic aromatic ring, and the phenyl group and a conjugated polycyclic aromatic ring of R 1 to R 3 are an alkyl group of C1-C20, C1-C20 Alkoxy group, halogen group, C5-C7 cycloalkyl group, phenyl group or conjugated polycyclic aromatic group may be further substituted.] 제 4 항에 있어서,The method of claim 4, wherein 상기 유기물층은 발광영역을 포함하며, 상기 발광영역은 상기 화학식 1로 표시되는 하나 이상의 화합물과 하나 이상의 발광 도판트를 포함하는 것을 특징으로 하는 유기발광소자.The organic material layer includes a light emitting region, and the light emitting region includes at least one compound represented by Formula 1 and at least one light emitting dopant. 제 5 항에 있어서,The method of claim 5, wherein 발광 도판트는 화학식 2 내지 화학식 4에서 선택되는 것을 특징으로 하는 유기발광소자.The light emitting dopant is an organic light emitting device, characterized in that selected from the formula (2) to (4). [화학식 2][Formula 2]
Figure 112007072452247-pat00132
Figure 112007072452247-pat00132
 [화학식 3][Formula 3]
Figure 112007072452247-pat00133
Figure 112007072452247-pat00133
 [화학식 4][Formula 4]
Figure 112007072452247-pat00134
Figure 112007072452247-pat00134
 [상기 화학식 3 또는 화학식 4에서, Ar1 내지 Ar2는 하기의 인데노플루오렌(indenofluorene), 플루오렌(fluorene) 또는 스피로-플루오렌(spiro-fluorene)이고; [In Formula 3 or Formula 4, Ar 1 to Ar 2 is the following indenofluorene (fluorine), fluorene (fluorene) or spiro-fluorene (spiro-fluorene);
Figure 112007072452247-pat00135
Figure 112007072452247-pat00136
Figure 112007072452247-pat00137
Figure 112007072452247-pat00135
Figure 112007072452247-pat00136
Figure 112007072452247-pat00137
 R11 내지 R16은 독립적으로 C1~C20의 알킬, C1~C5의 알킬이 치환되거나 치환되지 않은 페닐 또는 나프틸에서 선택되며;R 11 to R 16 are independently selected from C 1 to C 20 alkyl, C 1 to C 5 alkyl substituted or unsubstituted phenyl or naphthyl; Ar3 내지 Ar6는 독립적으로 C5~C20의 방향족 또는 다환방향족 고리에서 선택된다. 단, Ar1와 Ar2가 동일하고, Ar3와 Ar5가 동일하며, Ar4와 Ar6이 동일하다.Ar 3 to Ar 6 are independently selected from C 5 to C 20 aromatic or polycyclic aromatic rings. Provided that Ar 1 and Ar 2 are the same, Ar 3 and Ar 5 are the same, and Ar 4 and Ar 6 are the same;
Figure 112007072452247-pat00138
는
Figure 112007072452247-pat00139
또는
Figure 112007072452247-pat00140
이고,
Figure 112007072452247-pat00138
Is
Figure 112007072452247-pat00139
or
Figure 112007072452247-pat00140
ego, A와 B는 서로 독립적으로 화학결합이거나
Figure 112007072452247-pat00141
또는
Figure 112007072452247-pat00142
이고,A and B are independently chemical bonds
Figure 112007072452247-pat00141
or
Figure 112007072452247-pat00142
ego, R17과 R18는 서로 독립적으로 방향족 고리 또는 2개 이상의 방향족 고리가 접합된 접합 다환 방향족 고리이고,R 17 and R 18 are each independently an aromatic ring or a conjugated polycyclic aromatic ring in which two or more aromatic rings are bonded, R19 내지 R22은 서로 독립적으로 할로겐이 치환되거나 치환되지 않은 직쇄 또는 분지쇄의 C1-C20의 알킬기이고,R 19 to R 22 are each independently a substituted or unsubstituted linear or branched C 1 -C 20 alkyl group, R23 내지 R26는 서로 독립적으로 수소, 방향족기이고,R 23 to R 26 are each independently hydrogen, an aromatic group, Ar7 내지 Ar10는 서로 독립적으로 방향족 고리 또는 2개 이상의 방향족 고리가 접합된 접합 다환 방향족 고리이다.]Ar 7 to Ar 10 are each independently an aromatic ring or a conjugated polycyclic aromatic ring in which two or more aromatic rings are bonded.] 제 6 항에 있어서,The method of claim 6, 상기 발광 도판트는 하기 화합물로부터 선택되는 것을 특징으로 하는 유기발광소자.The light emitting dopant is an organic light emitting device, characterized in that selected from the following compounds.
Figure 112006075355432-pat00143
Figure 112006075355432-pat00143
Figure 112006075355432-pat00144
Figure 112006075355432-pat00144
Figure 112006075355432-pat00145
Figure 112006075355432-pat00145
Figure 112006075355432-pat00146
Figure 112006075355432-pat00146
Figure 112006075355432-pat00147
Figure 112006075355432-pat00147
Figure 112006075355432-pat00148
Figure 112006075355432-pat00148
Figure 112006075355432-pat00149
Figure 112006075355432-pat00149
Figure 112006075355432-pat00150
Figure 112006075355432-pat00150
Figure 112006075355432-pat00151
Figure 112006075355432-pat00151
Figure 112006075355432-pat00152
Figure 112006075355432-pat00152
Figure 112006075355432-pat00153
Figure 112006075355432-pat00153
Figure 112006075355432-pat00154
Figure 112006075355432-pat00154
Figure 112006075355432-pat00155
Figure 112006075355432-pat00155
Figure 112006075355432-pat00156
Figure 112006075355432-pat00156
Figure 112006075355432-pat00157
Figure 112006075355432-pat00157
Figure 112006075355432-pat00158
Figure 112006075355432-pat00158
Figure 112006075355432-pat00159
Figure 112006075355432-pat00159
Figure 112006075355432-pat00160
Figure 112006075355432-pat00160
Figure 112006075355432-pat00161
Figure 112006075355432-pat00161
Figure 112006075355432-pat00162
Figure 112006075355432-pat00162
Figure 112006075355432-pat00163
Figure 112006075355432-pat00163
Figure 112006075355432-pat00164
Figure 112006075355432-pat00164
Figure 112006075355432-pat00165
Figure 112006075355432-pat00165
Figure 112006075355432-pat00166
Figure 112006075355432-pat00166
Figure 112006075355432-pat00167
Figure 112006075355432-pat00167
Figure 112006075355432-pat00168
Figure 112006075355432-pat00168
Figure 112006075355432-pat00169
Figure 112006075355432-pat00169
Figure 112006075355432-pat00170
Figure 112006075355432-pat00170
Figure 112006075355432-pat00171
Figure 112006075355432-pat00171
Figure 112006075355432-pat00172
Figure 112006075355432-pat00172
Figure 112006075355432-pat00173
Figure 112006075355432-pat00173
Figure 112006075355432-pat00174
Figure 112006075355432-pat00174
Figure 112006075355432-pat00175
Figure 112006075355432-pat00175
Figure 112006075355432-pat00176
Figure 112006075355432-pat00176
Figure 112006075355432-pat00177
Figure 112006075355432-pat00177
Figure 112006075355432-pat00178
Figure 112006075355432-pat00178
Figure 112006075355432-pat00179
Figure 112006075355432-pat00179
Figure 112006075355432-pat00180
Figure 112006075355432-pat00180
Figure 112006075355432-pat00181
Figure 112006075355432-pat00181
Figure 112006075355432-pat00182
Figure 112006075355432-pat00182
Figure 112006075355432-pat00183
Figure 112006075355432-pat00183
Figure 112006075355432-pat00184
Figure 112006075355432-pat00184
 [상기 화학식에서 R19 내지 R22는 메틸기 또는 에틸기이다.][In the formula, R 19 to R 22 is a methyl group or an ethyl group.] 제 5 항에 있어서,The method of claim 5, wherein 발광 도판트는 화학식 5 내지 화학식 7에서 선택되는 것을 특징으로 하는 유기발광소자.The light emitting dopant is an organic light emitting device, characterized in that selected from the formula (5) to (7). [화학식 5][Formula 5]
Figure 112007072452247-pat00185
Figure 112007072452247-pat00185
 [화학식 6][Formula 6]
Figure 112007072452247-pat00186
Figure 112007072452247-pat00186
 [화학식 7][Formula 7]
Figure 112007072452247-pat00187
Figure 112007072452247-pat00187
 [상기 화학식 6 또는 화학식 7의 R27 및 R28는 서로 독립적으로 2개 이상의 방향족 고리가 접합된 접합 다환 방향족 고리이고, R29 내지 R32는 서로 독립적으로 방향족 고리이며, 상기 R27 내지 R32의 각 방향족 고리는 C1-C20의 알킬기가 더 치환될 수 있다.][R 27 and R 28 in Formula 6 or 7 are independently a conjugated polycyclic aromatic ring in which two or more aromatic rings are bonded to each other, R 29 to R 32 are each independently an aromatic ring, and R 27 to R 32 Each aromatic ring of may be further substituted with an alkyl group of C1-C20.] 제 8 항에 있어서,The method of claim 8, 상기 발광 도판트는 하기 화합물로부터 선택되는 것을 특징으로 하는 유기발광소자.The light emitting dopant is an organic light emitting device, characterized in that selected from the following compounds.
Figure 112006075355432-pat00188
Figure 112006075355432-pat00188
Figure 112006075355432-pat00189
Figure 112006075355432-pat00189
Figure 112006075355432-pat00190
Figure 112006075355432-pat00190
Figure 112006075355432-pat00191
Figure 112006075355432-pat00191
Figure 112006075355432-pat00192
Figure 112006075355432-pat00192
Figure 112006075355432-pat00193
Figure 112006075355432-pat00193
Figure 112006075355432-pat00194
Figure 112006075355432-pat00194
Figure 112006075355432-pat00195
Figure 112006075355432-pat00195
Figure 112006075355432-pat00196
Figure 112006075355432-pat00196
Figure 112006075355432-pat00197
Figure 112006075355432-pat00197
Figure 112006075355432-pat00198
Figure 112006075355432-pat00198
Figure 112006075355432-pat00199
Figure 112006075355432-pat00199
Figure 112006075355432-pat00200
Figure 112006075355432-pat00200
Figure 112006075355432-pat00201
Figure 112006075355432-pat00201
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000344691A (en) 1999-06-03 2000-12-12 Tdk Corp Compound for organic electroluminescent element and organic electroluminescent element
KR20020026867A (en) * 2000-03-30 2002-04-12 도미나가 가즈토 Organic electroluminescence device and organic luminescent medium
JP2006137956A (en) 2005-12-05 2006-06-01 Toppan Printing Co Ltd Luminescent material and organic thin film el element
JP2006210747A (en) 2005-01-31 2006-08-10 Sanyo Electric Co Ltd Organic electroluminescent element

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000344691A (en) 1999-06-03 2000-12-12 Tdk Corp Compound for organic electroluminescent element and organic electroluminescent element
KR20020026867A (en) * 2000-03-30 2002-04-12 도미나가 가즈토 Organic electroluminescence device and organic luminescent medium
JP2006210747A (en) 2005-01-31 2006-08-10 Sanyo Electric Co Ltd Organic electroluminescent element
JP2006137956A (en) 2005-12-05 2006-06-01 Toppan Printing Co Ltd Luminescent material and organic thin film el element

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