KR20080069156A - Iridium compound-based luminescence compounds comprising phenylpyridine groups with organic silicon and oled using the same as luminous material - Google Patents

Iridium compound-based luminescence compounds comprising phenylpyridine groups with organic silicon and oled using the same as luminous material Download PDF

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KR20080069156A
KR20080069156A KR1020080058436A KR20080058436A KR20080069156A KR 20080069156 A KR20080069156 A KR 20080069156A KR 1020080058436 A KR1020080058436 A KR 1020080058436A KR 20080058436 A KR20080058436 A KR 20080058436A KR 20080069156 A KR20080069156 A KR 20080069156A
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박춘건
서정대
권순기
김윤희
정성욱
안준환
김형선
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엘지디스플레이 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Abstract

A luminescence compound is provided to show significantly improved luminous efficiency. An organic light emitting diode using the same compound as an emission layer is provided to show excellent luminescent properties such as high external quantum efficiency, brightness and low driving voltage. An iridium complex compound is represented by a formula(1), wherein each L1, L2, R1 and R3 is H, and each L3 and R2 is a group represented by a formula(2) of -SiD1D2D3(wherein each D1 to D3 is methyl). In a method for preparing an organic light emitting diode(OLED) by forming an anode electrode, an emission layer and a cathode electrode on a substrate in sequence, the emission layer is formed by preparing CBP(cAMP-responsive Element Binding Protein) as a host material and depositing the iridium complex compound of the formula(1), wherein each L3 and R2 is trimethylsilane, and each L1, L2, R1 and R3 is H, as a dopant.

Description

유기 실리콘을 갖는 페닐 피리딘기를 포함하는 이리듐 화합물계 발광 화합물 및 이를 발색 재료로서 사용하는 유기전계발광소자{Iridium compound-based luminescence compounds comprising phenylpyridine groups with organic silicon and OLED using the same as luminous material}Iridium compound-based luminescence compounds comprising phenylpyridine groups with organic silicon and OLED using the same as luminous material}

본 발명은 2004년 10월 04일자로 출원된 국내특허출원 제10-2004-0078721호의 분할출원건이다.The present invention is a divided application of Korean Patent Application No. 10-2004-0078721 filed on October 04, 2004.

본 발명은 녹색 발광 화합물 및 이를 발색 재료로서 사용하는 유기전계발광소자에 관한 것으로서, 보다 구체적으로는, 색순도와 발광효율이 개선된 녹색 발광 화합물과 이를 발색 재료로서 사용하고 있는 유기전계발광소자에 관한 것이다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a green light emitting compound and an organic electroluminescent device using the same as a luminescent material. will be.

전계발광소자(eletroluminescence device: EL device)는 자발 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답시간이 빠르다는 장점을 가지고 있다. 이러한 EL 소자는 발광층(emitter layer) 형성용 재료에 따라 무기 EL 소자와 유기 EL 소자로 구분된다. 여기에서, 유기 EL 소자는 무기 EL 소자에 비하여 휘도, 구동전압 및 응답속도 특성이 우수하고 다색화가 가능하다는 장점을 가지고 있다.An electroluminescence device (EL device) is a self-luminous display device having advantages of wide viewing angle, excellent contrast and fast response time. Such EL elements are classified into inorganic EL elements and organic EL elements according to materials for forming an emitter layer. Herein, the organic EL device has an advantage of excellent luminance, driving voltage, and response speed, and multicoloring, compared to the inorganic EL device.

일반적인 유기 EL 소자는 기판 상부에 양극(anode)이 형성되어 있고, 이 양극 상부에 정공주입층, 정공수송층, 발광층, 전자수송층 및 음극이 순차적으로 형성되어 있는 구조를 가지고 있다. 여기에서, 정공수송층, 발광층 및 전자수송층은 유기 화합물로 이루어진 유기 박막들이다.A typical organic EL device has a structure in which an anode is formed on a substrate, and a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode. Here, the hole transport layer, the light emitting layer and the electron transport layer are organic thin films made of an organic compound.

유기 EL 소자를 제작하는 과정을 간단히 살펴보면,Looking briefly at the process of manufacturing an organic EL device,

(1) 먼저, 투명기판 위에 양극 물질을 입힌다. 양극 물질로는 흔히 ITO(indium tin oxide)가 쓰인다.(1) First, an anode material is coated on a transparent substrate. Indium tin oxide (ITO) is commonly used as the anode material.

(2) 그 위에 정공주입층(HIL:hole injecting layer)을 입힌다. 정공주입층으로는 주로 구리 프탈로시아닌(copper phthalocyanine(CuPc))을 10nm 내지 30nm 두께로 입힌다.(2) Apply a hole injecting layer (HIL) on it. As the hole injection layer, copper phthalocyanine (CuPc) is mainly coated with a thickness of 10 nm to 30 nm.

(3) 그런 다음, 정공수송층(HTL:hole transport layer)을 도입한다. 이러한 정공수송층으로는 4,4'-비스[N-(1-나프틸)-N-페닐아미노]바이페닐(4,4'-bis[N-(1-naphthyl)-N-phenylamino]-biphenyl(NPB))을 30nm 내지 60nm 정도 증착하여 입힌다.(3) Then, introduce a hole transport layer (HTL). As the hole transport layer, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB)) is coated by depositing about 30 nm to 60 nm.

(4) 그 위에 유기발광층(organic emitting layer)을 형성한다. 이때 필요에 따라 불순물(dopant)을 첨가한다. 녹색(green) 발광의 경우 흔히 유기발광층으로 트리스(8-하이드록시퀴놀레이트)알루미늄(Alq3)(tris(8-hydroxy-quinolatealuminum) )을 두께 30~60nm 정도 증착하며 불순물(dopant)로는 MQD(N-메틸퀴나크리돈)(N-Meth ylquinacridone)를 많이 쓴다.(4) An organic light emitting layer is formed thereon. At this time, a dopant is added as necessary. A common organic emission layer for a green (green) luminescent tris (8-hydroxy-quinol-rate) aluminum (Alq 3) (tris (8 -hydroxy-quinolatealuminum)) depositing a thickness of about 30 ~ 60nm and roneun impurity (dopant) MQD ( N-methylquinacridone) (N-Meth ylquinacridone) is used a lot.

(5) 그 위에 전자수송층(ETL:electron transport layer) 및 전자주입층(EI L: electron injecting layer)을 연속적으로 입히거나, 아니면 전자주입운송층을 형성한다. 녹색(green) 발광의 경우 상기(4)의 Alq3가 좋은 전자수송능력을 갖기 때문에 전자 주입/수송층을 쓰지 않는 경우도 많다.(5) An electron transport layer (ETL) and an electron injecting layer (EI L) are successively coated thereon, or an electron injection transport layer is formed thereon. In the case of green light emission, since Alq 3 in (4) has a good electron transport ability, the electron injection / transport layer is often not used.

(6) 다음으로 음극(cathode)을 입히고, 마지막으로 보호막을 덧 씌우게 된다.(6) Next, the cathode is coated and finally the protective film is covered.

상술한 바와 같은 구조를 갖는 유기EL 소자의 구동원리는 다음과 같다.The driving principle of the organic EL device having the structure as described above is as follows.

상기 양극 및 음극간에 전압을 인가하면 양극으로부터 주입된 정공은 정공 수송층을 경유하여 발광층으로 이동한다. 한편, 전자는 음극으로부터 전자 수송층을 경유하여 발광층에 주입되고, 발광층 영역에서 캐리어들이 재결합하여 엑시톤(exciton)을 생성한다. 이 엑시톤이 여기상태에서 기저상태로 변화되고, 이로 인하여 발광층의 형광성 분자가 발광함으로써 화상이 형성된다.When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer via the hole transport layer. On the other hand, electrons are injected into the light emitting layer from the cathode via the electron transport layer, and carriers are recombined in the light emitting layer to generate excitons. This exciton is changed from an excited state to a ground state, whereby an image is formed by the fluorescent molecules of the light emitting layer emitting light.

한편, 1987년 이스트만 코닥(Eastman Kodak)사에서는 발광층 형성용 재료로서 저분자인 방향족 다이아민과 알루미늄 착체를 이용하고 있는 유기전계발광소자를 개발하였다(Appl. Phys. Lett. 51. 913. 1987).In 1987, Eastman Kodak Corp. developed an organic electroluminescent device using a low molecular weight aromatic diamine and an aluminum complex as a light emitting layer forming material (Appl. Phys. Lett. 51.913. 1987).

이밖에도, 발광층 형성용 재료로서 폴리(p-페닐렌비닐렌)(PPV), 폴리(2-메톡시-5-(2'-에틸헥실옥시)-1,4-페닐렌비닐렌) 등과 같은 고분자를 사용하고 있는 유기전계발광소자가 발표되었다(Nature, 347, 539, 1990 & Appl. Phys. Lett. 58, 1982, 1991).In addition, as a light emitting layer forming material, poly (p-phenylenevinylene) (PPV), poly (2-methoxy-5- (2'-ethylhexyloxy) -1,4-phenylenevinylene) and the like Organic electroluminescent devices using polymers have been published (Nature, 347, 539, 1990 & Appl. Phys. Lett. 58, 1982, 1991).

한편, 종래에 사용된 이리듐 화합물은 발광특성이 우수하지만 삼중항-삼중항 소멸현상에 의한 효율감소 등 아직까지 더 개선해야할 점이 많이 있다.On the other hand, the iridium compound used in the prior art has excellent luminous properties, but there are still many points to be further improved such as efficiency reduction due to triplet-triple terminology phenomena.

이에 본 발명은 상기의 문제점을 해결하기 위해 안출된 것으로서, 발광효율 특성이 현저히 개선된 발광 화합물을 제공하려는 것을 목적으로 한다. 또한, 본 발명은 이 화합물을 발색재료로서 사용하는 표시소자를 제공하려는 것을 또 다른 목적으로 한다.Accordingly, an object of the present invention is to provide a light emitting compound which is remarkably improved in light emission efficiency characteristics as to solve the above problems. Moreover, another object of this invention is to provide the display element which uses this compound as a coloring material.

상기 본 발명의 목적을 달성하기 위하여, 본 발명에 따른 발광화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다.In order to achieve the object of the present invention, the light emitting compound according to the present invention is characterized by the following formula (1).

[화학식 1][Formula 1]

Figure 112008044359344-PAT00003
Figure 112008044359344-PAT00003

상기 화학식 1에서, L1, L2, L3 및 R1, R2, R3는 각각 독립적으로 수소, 아릴기, 알콕시, 알킬기로 이루어진 그룹 및 하기의 화학식 2로부터 선택되는 것을 특징으로 한다. 여기서, 상기 L1 내지 L3 및 R1 내지 R3는 서로 동일하거나 상이하다. 그리고, 상술한 L1 내지 L3 및 R1 내지 R3 중 적어도 하나는, 아래의 화학식 2로 표현되는 치환기일 수 있다. 그리고, 상술한 L1 내지 L3 및 R1 내지 R3 중 적어도 하나 는 아래의 화학식 3으로 표현되는 치환기일 수 있다.(여기서, L1 내지 L3는, L1 에서 L3까지 즉 L1, L2, L3를 모두 의미한다.)In Formula 1, L 1 , L 2 , L 3 and R 1 , R 2 , R 3 are each independently selected from the group consisting of hydrogen, aryl groups, alkoxy, alkyl groups and the following formula (2). Here, L 1 to L 3 and R 1 to R 3 are the same as or different from each other. At least one of L 1 to L 3 and R 1 to R 3 described above may be a substituent represented by Formula 2 below. And, at least one of the above-described L 1 to L 3 and R 1 to R 3 may be a substituent represented by the following general formula (3) (wherein L 1 to L 3 is L 1 to L 3 , that is, L 1 , L 2 , L 3 )

[화학식 2][Formula 2]

Figure 112008044359344-PAT00004
Figure 112008044359344-PAT00004

[화학식 3][Formula 3]

Figure 112008044359344-PAT00005
Figure 112008044359344-PAT00005

상기 화학식 2 및 화학식 3에서, D1 내지 D6는 각각 독립적으로 탄소수 1 내지 18의 알킬기, 탄소수 1 내지 18의 알콕시기, 치환되거나 치환되지 않은 탄소수 1 내지 18의 알릴기 및 치환되거나 치환되지 않은 탄소수 6 내지 18의 플루오르화된 알킬기 또는 알릴기로 이루어진 그룹에서 선택된다.In Formulas 2 and 3, D 1 to D 6 are each independently an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, an allyl group having 1 to 18 carbon atoms substituted or unsubstituted and an unsubstituted or substituted carbon atom. It is selected from the group consisting of a fluorinated alkyl group or allyl group having 6 to 18 carbon atoms.

본 발명에 따른 발광화합물은 발광효율특성이 현저히 개선되었고 이를 발광층르로 사용하는 OLED는 우수한 발광 특성 즉, 높은 외부양자효율, 휘도 및 낮은 구동전압 특성을 나타낸다.The light emitting compound according to the present invention has significantly improved light emitting efficiency characteristics, and the OLED using the light emitting layer has excellent light emitting characteristics, that is, high external quantum efficiency, brightness and low driving voltage.

상기 본 발명의 목적을 달성하기 위하여, 본 발명에 따른 발광화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다.In order to achieve the object of the present invention, the light emitting compound according to the present invention is characterized by the following formula (1).

Figure 112008044359344-PAT00006
Figure 112008044359344-PAT00006

상기 화학식 1에서, L1, L2, L3 및 R1, R2, R3는 각각 독립적으로 수소, 아릴기, 알콕시, 알킬기로 이루어진 그룹 및 하기의 화학식 2로부터 선택되는 것을 특징으로 한다. 여기서, 상기 L1 내지 L3 및 R1 내지 R3는 서로 동일하거나 상이하다. 그리고, 상술한 L1 내지 L3 및 R1 내지 R3 중 적어도 하나는, 아래의 화학식 2로 표현되는 치환기일 수 있다. 그리고, 상술한 L1 내지 L3 및 R1 내지 R3 중 적어도 하나는 아래의 화학식 3으로 표현되는 치환기일 수 있다.(여기서, L1 내지 L3는, L1 에서 L3까지 즉 L1, L2, L3를 모두 의미한다.)In Formula 1, L 1 , L 2 , L 3 and R 1 , R 2 , R 3 are each independently selected from the group consisting of hydrogen, aryl groups, alkoxy, alkyl groups and the following formula (2). Here, L 1 to L 3 and R 1 to R 3 are the same as or different from each other. At least one of L 1 to L 3 and R 1 to R 3 described above may be a substituent represented by Formula 2 below. And, at least one of the above-described L 1 to L 3 and R 1 to R 3 may be a substituent represented by the following formula (3) (L 1 to L 3 is, L 1 to L 3 , that is, L 1 , L 2 , L 3 )

Figure 112008044359344-PAT00007
Figure 112008044359344-PAT00007

Figure 112008044359344-PAT00008
Figure 112008044359344-PAT00008

상기 화학식 2 및 화학식 3에서, D1 내지 D6는 각각 독립적으로 탄소수 1 내지 18의 알킬기, 탄소수 1 내지 18의 알콕시기, 치환되거나 치환되지 않은 탄소수 1 내지 18의 알릴기 및 치환되거나 치환되지 않은 탄소수 6 내지 18의 플루오르화된 알킬기 또는 알릴기로 이루어진 그룹에서 선택된다.In Formulas 2 and 3, D 1 to D 6 are each independently an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, an allyl group having 1 to 18 carbon atoms substituted or unsubstituted and an unsubstituted or substituted carbon atom. It is selected from the group consisting of a fluorinated alkyl group or allyl group having 6 to 18 carbon atoms.

상기 화학식 1에 따른 발광 화합물은 그 자체로 사용되면 녹색 발광제로서 발광효율이 우수하며, 표시소자의 발색재료로서 유용하다. 또한, 본 발명에 따른 유기전계발광소자는 화학식 1의 발광 화합물을 사용하여 발광층 등과 같은 유기막을 형성하며, 통상적인 페닐 피리딘계 이리듐화합물을 사용한 경우와 비교하여 발광효율과 휘도 특성을 현저하게 개선시킨다.The light emitting compound according to Chemical Formula 1, when used as it is, has excellent light emitting efficiency as a green light emitting agent, and is useful as a coloring material of a display device. In addition, the organic light emitting device according to the present invention forms an organic film such as a light emitting layer using the light emitting compound of Formula 1, and significantly improves the luminous efficiency and luminance characteristics compared to the case of using a conventional phenyl pyridine-based iridium compound .

이하에서 상술한 화학식 1에 따른 발광 화합물의 일실시예의 제조방법 및 발광 특성을 설명한다. 본 실시예는 상기 화학식 1의 발광 화합물 중, L3와 R2가 모두 트라이메틸실란기이며, L1, L2 및 R1, R3는 수소인 하기 화학식 4로 표시되는 유기 발광 화합물을 특징으로 한다.Hereinafter, a method and a light emission characteristic of an embodiment of a light emitting compound according to Chemical Formula 1 will be described. In the present embodiment, in the light emitting compound of Formula 1, L 3 and R 2 are all trimethylsilane groups, and L 1 , L 2, and R 1 and R 3 are hydrogen, and the organic light emitting compound represented by the following Chemical Formula 4 is characterized by It is done.

Figure 112008044359344-PAT00009
Figure 112008044359344-PAT00009

상기 화학식 4의 화합물은 다음과 같이 합성한다.The compound of Formula 4 is synthesized as follows.

*1. 화합물(A)의 합성*One. Synthesis of Compound (A)

Figure 112008044359344-PAT00010
Figure 112008044359344-PAT00010

1,3-다이브로모벤젠(1,3-dibromobenzene)을 나트륨을 사용하여 건조된 다이에틸이써(diethylether)에 녹인 다음 1.2 당량의 n-부틸리튬(n-butyl-lithium)을 -78℃에서 서서히 첨가한다. 반응 혼합물을 상온에서 40분간 교반한 후, 다시 반응 혼합물을 -78℃로 냉각하여 1.2 당량의 클로로트라이메틸실란(chlorotrimethylsilane)을 첨가한 후, 상온에서 10시간 동안 교반한다. 반응 혼합물에 물을 부어 반응을 종결하고 다이에틸이써로 추출한 다음 진공증류로 상기 화합물(A)를 얻었다(수율: 73%).1,3-dibromobenzene was dissolved in diethylether dried using sodium, and 1.2 equivalents of n-butyl-lithium was then dried at -78 ° C. Add slowly. After the reaction mixture was stirred at room temperature for 40 minutes, the reaction mixture was further cooled to -78 ° C to add 1.2 equivalents of chlorotrimethylsilane, and then stirred at room temperature for 10 hours. Water was added to the reaction mixture to complete the reaction, followed by extraction with diethyl ether to obtain the compound (A) by vacuum distillation (yield: 73%).

2. 화합물(B)의 합성2. Synthesis of Compound (B)

Figure 112008044359344-PAT00011
Figure 112008044359344-PAT00011

상기 화합물(A)를 나트륨을 사용하여 건조된 다이에틸이써에 녹인 다음 1.2 당량의 n-부틸리튬을 -78℃에서 서서히 첨가한다. 반응 혼합물을 상온에서 40분간 교반한 후, 다시 반응 혼합물을 -78℃에서 서서히 첨가한다. 반응 혼합물을 상온에서 40분간 교반한 후, 다시 반응 혼합물을 -78℃로 냉각하여 2 당량의 트라이에틸보레이트(triethylborate)를 첨가한 후, 상온에서 12시간 동안 교반한다. 반응 혼합물을 1N-HCl에 서서히 붓고 에틸아세테이트로 추출하여 상기 화합물(B)를 얻었 다(수율:35%).The compound (A) is dissolved in diethyl ether dried with sodium, and then 1.2 equivalents of n-butyllithium are slowly added at -78 ° C. The reaction mixture is stirred at room temperature for 40 minutes, and then the reaction mixture is slowly added at -78 ° C. After the reaction mixture was stirred at room temperature for 40 minutes, the reaction mixture was further cooled to -78 ° C to add 2 equivalents of triethylborate, and then stirred at room temperature for 12 hours. The reaction mixture was slowly poured into 1N-HCl and extracted with ethyl acetate to obtain the compound (B) (yield: 35%).

3. 화합물(C)의 합성3. Synthesis of Compound (C)

Figure 112008044359344-PAT00012
Figure 112008044359344-PAT00012

2,5-다이브로모피리딘(2,5-dibromopyridine)을 나트륨을 사용하여 건조된 다이에틸이써에 녹인 다음 1.2 당량의 n-부틸리튬을 -78℃에서 서서히 첨가한다. 반응 혼합물을 같은 온도에서 40분간 교반한 후에 1.2 당량의 클로로트라이메틸실란을 첨가한 후, 상온에서 10시간 동안 교반한다. 반응 혼합물을 물에 부어 반응을 종결하고 다이에틸이써로 추출한 다음 진공증류로 화합물(C)를 얻었다(수율:73%).2,5-dibromopyridine is dissolved in diethylether dried with sodium and then 1.2 equivalents of n-butyllithium are slowly added at -78 ° C. The reaction mixture is stirred at the same temperature for 40 minutes, then 1.2 equivalents of chlorotrimethylsilane is added, followed by stirring at room temperature for 10 hours. The reaction mixture was poured into water to terminate the reaction, extracted with diethyl ether, and the compound (C) was obtained by vacuum distillation (yield: 73%).

4. 화합물(D)의 합성4. Synthesis of Compound (D)

Figure 112008044359344-PAT00013
Figure 112008044359344-PAT00013

질소 기류하에서, 화합물(B) 1.2 당량과 화합물(C) 1 당량을 THF/2M-K2CO3 용액을 가한 다음 5시간 환류시킨다. 반응 혼합물을 1N-HCl 수용액에서 서서히 부어 반응을 종결하여 다이에틸이써로 추출하여 화합물(D)를 얻었다(수율:92%).Under a stream of nitrogen, 1.2 equivalents of compound (B) and 1 equivalent of compound (C) were added to a THF / 2M-K 2 CO 3 solution and then refluxed for 5 hours. The reaction mixture was poured slowly from a 1N-HCl aqueous solution to terminate the reaction, and extracted with diethyl ether to give the compound (D) (yield: 92%).

5. 화학식 4의 화합물의 합성5. Synthesis of Compound of Formula 4

Figure 112008044359344-PAT00014
Figure 112008044359344-PAT00014

질소 기류하에서 이리듐(III) 아세틸아세토네이트(Iridium acetylacetonate) 1 당량을 에틸렌글리콜에 넣은 후 30분간 80℃에서 교반한 다음 화합물(D) 5 당량을 가한 후 20시간 동안 환류시킨다. 온도를 실온으로 내린 다음 1N-HCl에 반응물을 붓고 교반하면 침전물이 생기고, 이 침전물을 여과하여 물로 세척 후 이 화합물을 실리카겔 관에서 다이클로로메테인으로 용리하여 화학식 4의 화합물을 얻었다(수율:24%). 상기 화학식 2의 화합물의 구조는 질량분석으로 확인하였다. 그 결과는 도 3으로 나타내었다.Under nitrogen stream, 1 equivalent of Iridium acetylacetonate was added to ethylene glycol, stirred at 80 ° C. for 30 minutes, and 5 equivalents of Compound (D) were added thereto, followed by reflux for 20 hours. After the temperature was lowered to room temperature, the reactant was poured into 1N-HCl and stirred to form a precipitate. The precipitate was filtered and washed with water, and the compound was eluted with dichloromethane in a silica gel tube to obtain a compound of formula 4 (Yield: 24). %). The structure of the compound of Formula 2 was confirmed by mass spectrometry. The result is shown in FIG.

실시예Example

ITO(Indium Tin Oxide)(산화인듐주석) 기판(glass)의 발광 면적이 3mm×3mm 크기가 되도록 패터닝(patterning)한 후 세정한다. 기판을 진공 챔버에 장착한 후 기본 압력이 1×10-6torr가 되도록 한 후 유기물을 ITO위에 CuPC(200Å), NPB(400Å), 발광층(200Å), BCP(100Å), Alq3(200Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다. 이 때, 발광층은 CBP를 호스트로하고 도펀트로 화학식 4를 8% 섞어서 증착 하였을 때 결과가 11.1mA/cm2에서 구동전압이 9.71V이고 휘도 955nits, 색좌표(0.316 0.603)와 같이 구현되었다.The light emitting area of the Indium Tin Oxide (ITO) (glass) substrate is patterned so as to have a size of 3 mm x 3 mm and then cleaned. After mounting the substrate in the vacuum chamber, the basic pressure is 1 × 10 -6 torr, and the organic material is placed on ITO CuPC (200 (), NPB (400Å), light emitting layer (200Å), BCP (100Å), Alq 3 (200Å) The film was formed in the order of LiF (5 kV) and Al (1000 kV). In this case, when the light emitting layer was deposited with CBP as a host and mixed with 8% of the formula 4, the driving voltage was 9.71V at 11.1mA / cm2, and the luminance was 955nits and the color coordinates (0.316 0.603).

본 발명에 따른 OLED는 도 5 및 도 6에서 확인할 수 있듯이 우수한 발광특성을 나타낸다.The OLED according to the present invention exhibits excellent light emission characteristics as can be seen in FIGS. 5 and 6.

도 1은 층으로 제조되는 일반적인 OLED의 구조를 나타내는 그림이다.1 is a diagram showing the structure of a typical OLED fabricated as a layer.

도 2는 본 발명의 화학식 4로 표시되는 유기 발광 화합물의 합성과정을 나타내는 그림이다.2 is a diagram showing a synthesis process of an organic light emitting compound represented by Chemical Formula 4 of the present invention.

도 3은 본 발명의 화학식 4로 표시되는 유기 발광 화합물의 질량분석을 나타내는 그래프이다.3 is a graph showing mass spectrometry of an organic light emitting compound represented by Chemical Formula 4 of the present invention.

도 4는 본 발명의 화학식 4로 표시되는 유기 발광 화합물의 UV/PL을 나타내는 그래프이다.4 is a graph showing UV / PL of the organic light emitting compound represented by Chemical Formula 4 of the present invention.

도 5 및 6은 본 발명의 화학식 4로 표시되는 유기 발광 화합물을 발광층으로 사용한 OLED의 특성을 나타내는 그래프이다.5 and 6 are graphs showing the characteristics of the OLED using the organic light emitting compound represented by the formula (4) of the present invention as a light emitting layer.

※ 주요 도면 부호의 설명※ Explanation of Main References

11: 유리 기판 12: 양극 13: 정공수송층 14:발광층11: glass substrate 12: anode 13: hole transport layer 14: light emitting layer

15: 전자수송층 16: 음극 17: 유리 기판15: electron transport layer 16: cathode 17: glass substrate

Claims (2)

하기 화학식 1의 이리듐착체 화합물:Iridium complex compound of formula [화학식 1][Formula 1]
Figure 112008044359344-PAT00015
Figure 112008044359344-PAT00015
 (상기 식에서, 상기 L1, L2, 및 R1, R3는 수소이고, L3,및 R2는 하기의 화학식 2로 구성된 그룹이며,(Wherein L 1 , L 2 , and R 1 , R 3 are hydrogen, L 3 , and R 2 are a group consisting of the following Chemical Formula 2, [화학식 2][Formula 2]
Figure 112008044359344-PAT00016
Figure 112008044359344-PAT00016
 상기 화학식 2에서, D1 내지 D3는 각각 메틸기이다).In Formula 2, D 1 to D 3 are each a methyl group). 기판 상에, 애노드 전극과 발광층 및 캐소드 전극을 차례로 형성하여 이루어지는 유기전계발광소자의 제조방법에 있어서,In the manufacturing method of the organic electroluminescent element formed by sequentially forming an anode electrode, a light emitting layer, and a cathode electrode on a board | substrate, 상기 발광층을 형성하는 단계는, 호스트 물질로 CBP를 준비하고 하기 화학식 1의 물질을 도핑하여 증착하는 것을 특징으로 하는 유기전계발광소자의 제조방법:The forming of the light emitting layer may include preparing a CBP as a host material, and doping the material of Chemical Formula 1 to deposit the organic light emitting device. [화학식 1][Formula 1]
Figure 112008044359344-PAT00017
Figure 112008044359344-PAT00017
 (상기 식에서, L3와 R2는 트라이메틸실란기이고, L1, L2 및 R1, R3는 수소이다).(Wherein L 3 and R 2 are trimethylsilane groups and L 1 , L 2 and R 1 , R 3 are hydrogen).
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