KR20070105080A - Red phosphorescene compounds and organic electroluminescence devices using the same - Google Patents

Red phosphorescene compounds and organic electroluminescence devices using the same Download PDF

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KR20070105080A
KR20070105080A KR1020060037102A KR20060037102A KR20070105080A KR 20070105080 A KR20070105080 A KR 20070105080A KR 1020060037102 A KR1020060037102 A KR 1020060037102A KR 20060037102 A KR20060037102 A KR 20060037102A KR 20070105080 A KR20070105080 A KR 20070105080A
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light emitting
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emitting layer
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서정대
이경훈
박춘건
김중근
정현철
빈종관
피성훈
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엘지전자 주식회사
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Priority to US11/593,146 priority patent/US8501328B2/en
Priority to EP06023132.1A priority patent/EP1784057B1/en
Publication of KR20070105080A publication Critical patent/KR20070105080A/en

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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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C09K11/87—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing platina group metals
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
    • H10K50/171—Electron injection layers
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Abstract

A red phosphorescence compound is provided to impart high color purity (CIE color purity X=0.65 or higher), high luminance and improved life span to an organic electroluminescence device using the same compound as a dopant for a light emitting layer. A red phosphorescence compound is represented by the following formula 1, wherein the formula (a) is the formula (b); each of R1, R2, R3 and R4 is selected from the group consisting of H, C1-C4 alkyl and alkoxy groups; and the formula (c) is selected from the group consisting of 2,4-pentanedione, 2,2,6,6-tetramethylheptane-3,5-dione, 1,3-propanedione, 1,3-butanedione, 3,5-heptanedione, 1,1,1-trifluoro-2,4-pentanedione, 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and 2,2-dimethyl-3,5-hexanedione. The red phosphorescence compound is used in a light emitting layer in an amount of 0.5-20 wt% together with a host compound selected from Al, Zn metal complexes and carbazole derivatives.

Description

적색 인광 화합물 및 이를 사용한 유기전계발광소자{Red phosphorescene compounds and organic electroluminescence devices using the same}Red phosphorescene compounds and organic electroluminescence devices using the same

도 1은 유기 EL 소자의 색순도가 높아질수록(CIE 색좌표 X값이 커질수록) 시감도가 떨어지는 것을 나타내는 그래프이다.1 is a graph showing that the visibility is lowered as the color purity of the organic EL element is increased (as the CIE color coordinate X value is larger).

도 2는 본 발명의 실시예에서 사용되는 화합물인 NPB, 구리(II)프탈로시아닌(CuPc), (btp)2Ir(acac), Alq3, BAlq 및 CBP의 구조식을 나타낸다.2 shows structural formulas of NPB, copper (II) phthalocyanine (CuPc), (btp) 2 Ir (acac), Alq 3 , BAlq and CBP, which are compounds used in Examples of the present invention.

본 발명은 적색 인광 화합물 및 이를 사용하는 유기전계발광소자에 관한 것이다. 보다 구체적으로, 본 발명은 상기 적색 인광 화합물을 양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 음극을 순서대로 적층한 것을 포함하여 이루어지는 유기전계발광소자의 발광층의 도펀트(dopant)로 사용하는 유기전계발광소자에 관한 것이다.The present invention relates to a red phosphorescent compound and an organic light emitting device using the same. More specifically, the present invention includes a dopant of a light emitting layer of an organic light emitting device comprising a laminate of an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode in this order. It relates to an organic electroluminescent device used in the).

최근 표시장치의 대형화에 따라 공간 점유가 적은 평면표시소자의 요구가 증대되고 있는데, 이러한 평면표시소자 중 하나로서 유기발광다이오드(organic light emitting diode: OLED)라고도 불리는 유기 전계 발광 소자의 기술이 빠른 속도로 발전하고 있으며, 이미 여러 시제품들이 발표된 바 있다.Recently, as the size of the display device increases, the demand for a flat display device having less space is increasing. As one of the flat display devices, an organic light emitting diode (OLED), also called an organic light emitting diode (OLED), has a high speed. It has been developed and several prototypes have already been announced.

유기 전계 발광 소자는 전자 주입 전극(음극) 과 정공 주입 전극(양극) 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자이다. 플라스틱 같은 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 전계 발광(EL) 디스플레이에 비해 낮은 전압에서 (10V이하) 구동이 가능하고, 또한 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다. 또한 유기 전계 발광(EL) 소자는 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 차세대 풍부한 색 디스플레이 소자로 많은 사람들의 많은 관심의 대상이 되고 있다. 여기서 유기 EL 소자를 제작하는 과정을 간단히 살펴보면,The organic electroluminescent device is a device that emits light by dissipating electrons and holes after pairing when electrons are injected into the organic film formed between the electron injection electrode (cathode) and the hole injection electrode (anode). Not only can the device be formed on a flexible transparent substrate such as plastic, but it can also be driven at a lower voltage (10V or less) than a plasma display panel or an inorganic electroluminescent (EL) display. In addition, the power consumption is relatively low, there is an advantage that the color is excellent. In addition, the organic electroluminescent (EL) device can display three colors of green, blue, and red, and thus, has become a subject of much interest as a next-generation rich color display device. Here is a brief look 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 deposited by depositing about 30 nm to 60 nm.

(4) 그 위에 유기발광층 (organic emitting layer)을 형성한다. 이때 필요에 따라 도펀트(dopant)를 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) Form an organic emitting layer thereon. At this time, a dopant is added as necessary. Green (green) when the light emission is often the organic light emitting layer of tris (8-hydroxy-quinol-rate) aluminum (Alq 3) (tris (8 -hydroxy-quinolatealuminum) thick deposited about 30 ~ 60nm and the roneun impurity (dopant), MQD (N Methyl quinacridone) (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 주입층/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 the above (4) has a good electron transport ability, the electron injection layer / transport layer is often not used.

(6) 다음 음극(cathode)을 입히고, 마지막으로 보호막을 덧 씌우게 된다.(6) The next cathode is applied and finally the protective film is overlaid.

상기와 같은 구조에 있어 발광층을 어떻게 형성하느냐에 따라 청색, 녹색, 적색의 발광 소자를 각각 구현할 수가 있다.In the above structure, blue, green, and red light emitting devices may be implemented depending on how the light emitting layer is formed.

발광 재료의 경우 양쪽 전극에서부터 주입된 전자와 정공의 재결합에 의해 여기자가 형성되며, 일중항 여기자의 경우 형광, 삼중항 여기자의 경우 인광에 관여하게 된다. 인광재료에 관여하는 생성확율이 75%인 삼중항 여기자를 사용하는 형광재료는 생성확율이 25%인 일중항 여기자를 사용하는 형광재료보다 뛰어난 발광효율을 보인다. 이러한 인광재료중 적색 인광 재료는 형광재료에 비해 매우 높은 발광효율을 가질수 있으므로 유기전계발광소자의 효율을 높이는 중요한 방법으로 많이 연구되고 있다. In the case of the light emitting material, excitons are formed by recombination of electrons and holes injected from both electrodes, and singlet excitons are involved in phosphorescence and triplet excitons. Fluorescent materials using triplet excitons with a 75% generation probability involved in phosphorescent materials show superior luminous efficiency than fluorescent materials using singlet excitons with a 25% generation probability. Among these phosphorescent materials, red phosphorescent materials can have very high luminous efficiency compared to fluorescent materials, and thus, many researches have been made as important methods for increasing the efficiency of organic light emitting diodes.

인광 재료를 이용하기 위해서는 높은 발광효율, 높은 색순도, 긴 발광수명이 요구되며, 이중 적색의 경우 도 1과 같이 색순도가 높아질수록(CIE 색좌표 X값이 커질수록) 시감도가 떨어져 높은 발광효율을 얻기가 어려운 문제가 있다.In order to use phosphorescent materials, high luminous efficiency, high color purity and long luminous lifetime are required, and in the case of red color, as shown in FIG. 1, the higher the color purity (as the CIE color coordinate X value becomes larger), the lower the visibility and the higher the luminous efficiency. There is a difficult problem.

이에따라 우수한 색좌표 특성(CIE색순도 X=0.65이상)과 높은 발광효율, 긴 발광수명의 특징을 가지는 적색 인광 발광화합물의 개발이 요구되고 있다.Accordingly, there is a demand for the development of a red phosphorescent light emitting compound having excellent color coordinate characteristics (CIE color purity X = 0.65 or more), high luminous efficiency, and long luminous lifetime.

본 발명은 유기발광소자의 발광층에 도펀트로서 사용되는 화학식 1의 화합물을 합성하여 고색순도, 고휘도, 장수명의 유기전계발광소자를 제공하는데 그 목적이 있다.SUMMARY OF THE INVENTION An object of the present invention is to synthesize a compound of Formula 1 used as a dopant in a light emitting layer of an organic light emitting device to provide an organic light emitting device having high color purity, high brightness and long life.

상기와 같은 목적을 달성하기 위해서, 본 발명은 하기 화학식 1로 표시되는 적색 인광 화합물과 이를 양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 음극을 순서대로 적층한 것을 포함하여 이루어지는 유기전계발광소자의 발광층의 도펀트(dopant)로 사용하는 유기전계발광소자를 제공한다. In order to achieve the above object, the present invention includes a laminate of a red phosphorescent compound represented by the following formula (1) and the anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a cathode in this order An organic electroluminescent device used as a dopant of a light emitting layer of an organic electroluminescent device is provided.

Figure 112006028843713-PAT00005
Figure 112006028843713-PAT00005

상기 화학식 1에서

Figure 112006028843713-PAT00006
은
Figure 112006028843713-PAT00007
이며, R1, R2, R3 및 R4는 수소, C1-C4의 알킬기, 알콕시기로 이루어진 그룹으로부터 선택되며,
Figure 112006028843713-PAT00008
는 2,4-펜테인다이온(
Figure 112006028843713-PAT00009
), 2,2,6,6,-테트라메틸헵테인-3,5-다이온(
Figure 112006028843713-PAT00010
), 1,3-프로페인다이온(
Figure 112006028843713-PAT00011
), 1,3-부테인다이온(
Figure 112006028843713-PAT00012
), 3,5-헵테인다이온(
Figure 112006028843713-PAT00013
), 1,1,1-트라이플루오로-2,4-펜테인다이온(
Figure 112006028843713-PAT00014
), 1,1,1,5,5,5-헥사플루오로-2,4-펜테인다이 온(
Figure 112006028843713-PAT00015
) 및 2,2-다이메틸-3,5-헥세인다이온(
Figure 112006028843713-PAT00016
)으로 이루어진 그룹으로부터 선택되는 것을 특징으로 한다.In Chemical Formula 1
Figure 112006028843713-PAT00006
silver
Figure 112006028843713-PAT00007
R 1, R 2, R 3 and R 4 are selected from the group consisting of hydrogen, an alkyl group of C 1 -C 4 , an alkoxy group,
Figure 112006028843713-PAT00008
Is 2,4-pentane ion (
Figure 112006028843713-PAT00009
), 2,2,6,6, -tetramethylheptane-3,5-dione (
Figure 112006028843713-PAT00010
), 1,3-propane ion (
Figure 112006028843713-PAT00011
), 1,3-butanedione (
Figure 112006028843713-PAT00012
), 3,5-heptanedionate (
Figure 112006028843713-PAT00013
), 1,1,1-trifluoro-2,4-pentaneionate (
Figure 112006028843713-PAT00014
), 1,1,1,5,5,5-hexafluoro-2,4-pentanedione (
Figure 112006028843713-PAT00015
) And 2,2-dimethyl-3,5-hexane ions (
Figure 112006028843713-PAT00016
It is characterized in that it is selected from the group consisting of.

상기 화학식 1에서

Figure 112006028843713-PAT00017
은 하기 화합물 중 어느 하나인 것을 특징으로 한다.In Chemical Formula 1
Figure 112006028843713-PAT00017
Is characterized in that any one of the following compounds.

Figure 112006028843713-PAT00018
Figure 112006028843713-PAT00018

상기 화학식 1의 바람직한 예는 하기 화합물 중 어느 하나인 것을 특징으로 한다.Preferred examples of the formula (1) is characterized in that any one of the following compounds.

Figure 112006028843713-PAT00019
Figure 112006028843713-PAT00019

Figure 112006028843713-PAT00020
Figure 112006028843713-PAT00020

본 발명에 따른 유기전계발광소자는 Al, Zn 금속 착물 및 카바졸 유도체 중 어느 하나를 발광층의 호스트로 사용할 수 있으며 상기 도펀트의 양은 0.5중량% - 20중량%인 것이 바람직하다. 상기 유기전계발광소자는 도펀트의 양이 상기 범위내에서 사용될 때 본 발명에 따른 효과를 나타낸다. 상기 Al, Zn 금속 착물의 리간드는 퀴놀일, 바이페닐일, 아이소퀴놀일, 페닐일, 메틸퀴놀일, 다이메틸퀴놀일 및 다 이메틸아이소퀴놀일기로 이루어지고, 카바졸 유도체는 CBP로 이루어지는 것이 바람직하다. In the organic electroluminescent device according to the present invention, any one of Al, Zn metal complex and carbazole derivatives may be used as a host of the light emitting layer, and the amount of the dopant is preferably 0.5 wt% to 20 wt%. The organic electroluminescent device exhibits an effect according to the invention when the amount of dopant is used within this range. The ligands of the Al and Zn metal complexes consist of quinolyl, biphenylyl, isoquinolyl, phenylyl, methylquinolyl, dimethylquinolyl and dimethylisoquinolyl groups, and the carbazole derivatives consist of CBP. desirable.

이하에서 본 발명에 따른 유기전계발광소자에 사용되는 적색 인광 화합물 중 A-2로 나타낸 화합물(이리듐(III) (1-(3-메틸페닐)-7-메틸아이소퀴놀리나토-N,C2 ’)(2,4-펜테인다이오네이트-O,O)을 예로 들어 본 발명의 적색 인광 화합물의 합성 방법을 설명하기로 한다.Among the red phosphorescent compounds used in the organic electroluminescent device according to the present invention, compounds represented by A-2 (Iridium (III) (1- (3-methylphenyl) -7-methylisoquinolinato-N, C 2 ′) A method for synthesizing the red phosphorescent compound of the present invention will be described using (2,4-pentanedionate-O, O) as an example.

합성예Synthesis Example

1. 1-(3-메틸페닐)-7-메틸아이소퀴놀린의 합성 1.Synthesis of 1- (3-methylphenyl) -7-methylisoquinoline

Figure 112006028843713-PAT00021
Figure 112006028843713-PAT00021

건조된 2구 둥근 바닥 플라스크에 베조산-(β-하이드록시-4-메틸-펜틸아마이드)(2.1mmol), 산화인(V)(10mmol) 및 데카하이드로나프탈렌(50mmol)을 넣은 후 120℃에서 5시간 정도를 교반 후 반응이 종료가 되면 다이클로로메테인과 물을 사용하여 추출한 후 감압 증류하여 실리카겔 컬럼 후 용매를 감압 증류한 후 다이클로로메테인과 석유 에터를 사용하여 재결정을 하여 여과하면 생성물인 1-(3-메틸페닐)-7-메틸아이소퀴놀린의 고체를 얻었다.Bezoic acid- (β-hydroxy-4-methyl-pentylamide) (2.1 mmol), phosphorus oxide (V) (10 mmol) and decahydronaphthalene (50 mmol) were added to a dried two-necked round bottom flask at 120 ° C. After stirring for about 5 hours, when the reaction is completed, the mixture is extracted with dichloromethane and water, distilled under reduced pressure, silica gel column, solvent is distilled off under reduced pressure, recrystallized with dichloromethane and petroleum ether, and filtered. A solid of phosphorus 1- (3-methylphenyl) -7-methylisoquinoline was obtained.

2. 클로로-가교 다이머 착물의 합성2. Synthesis of Chloro-crosslinked Dimer Complex

Figure 112006028843713-PAT00022
Figure 112006028843713-PAT00022

염화 이리듐(1mmol)과 1-(3-메틸페닐)-7-메틸아이소퀴놀린(2.5mmol)을 2-에톡시에탄올 : 증류수가 3:1로 혼합된 용액(30ml)에 넣고 24시간 동안 환류시킨다. 물을 첨가하여 형성된 고체를 여과한 후 메탄올과 석유 에터로 세척하여 클로로-가교 다이머 착물을 얻었다.Iridium chloride (1 mmol) and 1- (3-methylphenyl) -7-methylisoquinoline (2.5 mmol) were added to a solution (30 ml) mixed with 2-ethoxyethanol: distilled water 3: 1 and refluxed for 24 hours. The solid formed by addition of water was filtered and washed with methanol and petroleum ether to obtain a chloro-crosslinked dimer complex.

3. 이리듐(III) (1-(3-메틸페닐)-7-메틸아이소퀴놀리나토-N,C2 ’)(2,4-펜테인다이오네이트-O,O)의 합성3. Synthesis of Iridium (III) (1- (3-methylphenyl) -7-methylisoquinolinato-N, C 2 ′ ) (2,4-pentanedionate-O, O)

Figure 112006028843713-PAT00023
Figure 112006028843713-PAT00023

클로로-가교 다이머 착물(1mmol), 2,4-펜테인다이온(3mmol) 및 Na2CO3 (6mmol)을 2-에톡시에탄올(30ml)에 넣고 24시간 동안 교반 시킨다. 이를 상온으로 식힌 후 증류수를 첨가하여 여과 후 고체를 얻었다. 형성된 고체를 다이클로로메테인에 녹인 후 실리카겔을 이용하여 여과하였고 다이클로로메테인을 감압제거 후 메탄올과 석유 에터로 세척하여 화합물을 얻었다.Chloro-crosslinked dimer complex (1 mmol), 2,4-pentanedione ( 3 mmol) and Na 2 CO 3 (6 mmol) were added to 2-ethoxyethanol (30 ml) and stirred for 24 hours. After cooling to room temperature, distilled water was added to give a solid after filtration. The solid formed was dissolved in dichloromethane and filtered using silica gel. The dichloromethane was removed under reduced pressure and washed with methanol and petroleum ether to obtain a compound.

이하에서 본 발명을 하기 실시예를 통해 설명하기로 한다. 다만, 본 발명의 하기 실시예들에 한정되는 것은 아니다.Hereinafter, the present invention will be described through the following examples. However, it is not limited to the following embodiments of the present invention.

실시예Example

실시예 1Example 1

ITO 유리의 발광면적이 3mm x 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1 x 10-6torr가 되도록 한 후 유기물을 ITO 위에 CuPC(200Å), NPD(400Å), BAlq + A-1(7%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in the vacuum chamber, the basic pressure was 1 x 10 -6 torr, and the organics were placed on ITO CuPC (200Å), NPD (400Å), BAlq + A-1 (7%) (200Å), Alq 3 It formed into a film in order of (300 microseconds), LiF (5 microseconds), and Al (1000 microseconds).

0.9mA에서 801cd/m2(6.6V)를 나타내었으며 이때 CIE x=0.649, y=0.360을 나타내었다. 수명(초기휘도의 반)은 2000cd/m2에서 5100시간이었다.At 0.9 mA, 801 cd / m 2 (6.6 V) was shown, with CIE x = 0.649 and y = 0.360. The lifetime (half the initial luminance) was 5100 hours at 2000 cd / m 2 .

실시예 2Example 2

ITO 유리의 발광면적이 3mm x 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1 x 10-6torr가 되도록 한 후 유기물을 ITO 위에 CuPC(200Å), NPD(400Å), BAlq + A-2(7%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in the vacuum chamber, the basic pressure is 1 x 10 -6 torr, and the organics are placed on ITO CuPC (200Å), NPD (400Å), BAlq + A-2 (7%) (200Å), Alq 3 It formed into a film in order of (300 microseconds), LiF (5 microseconds), and Al (1000 microseconds).

0.9mA에서 795cd/m2(6.3V)를 나타내었으며 이때 CIE x=0.650, y=0.361을 나타내었다. 수명(초기휘도의 반)은 2000cd/m2에서 4800시간이었다.At 0.9 mA, 795 cd / m 2 (6.3 V) was shown, with CIE x = 0.650 and y = 0.361. The lifetime (half the initial luminance) was 4800 hours at 2000 cd / m 2 .

실시예 3Example 3

ITO 유리의 발광면적이 3mm x 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1 x 10-6torr가 되도록 한 후 유기물을 ITO 위에 CuPC(200Å), NPD(400Å), BAlq + A-7(7%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in the vacuum chamber, the basic pressure was 1 x 10 -6 torr, and the organics were placed on the ITO CuPC (200Å), NPD (400Å), BAlq + A-7 (7%) (200Å), Alq 3 It formed into a film in order of (300 microseconds), LiF (5 microseconds), and Al (1000 microseconds).

0.9mA에서 783cd/m2(6.1V)를 나타내었으며 이때 CIE x=0.651, y=0.362를 나타내었다. 수명(초기휘도의 반)은 2000cd/m2에서 5500시간이었다.783 cd / m 2 (6.1 V) at 0.9 mA, with CIE x = 0.651 and y = 0.362. The lifetime (half the initial luminance) was 5500 hours at 2000 cd / m 2 .

실시예 4Example 4

ITO 유리의 발광면적이 3mm x 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1 x 10-6torr가 되도록 한 후 유기물을 ITO 위에 CuPC(200Å), NPD(400Å), BAlq + B-2(7%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in the vacuum chamber, the basic pressure was 1 x 10 -6 torr, and the organics were placed on ITO CuPC (200kPa), NPD (400kPa), BAlq + B-2 (7%) (200kPa), Alq 3 It formed into a film in order of (300 microseconds), LiF (5 microseconds), and Al (1000 microseconds).

0.9mA에서 768cd/m2(6.0V)를 나타내었으며 이때 CIE x=0.652, y=0.361을 나타내었다. 수명(초기휘도의 반)은 2000cd/m2에서 4000시간이었다.At 0.9mA, 768cd / m 2 (6.0V) was displayed, with CIE x = 0.652 and y = 0.361. The lifetime (half the initial luminance) was 4000 hours at 2000 cd / m 2 .

실시예 5Example 5

ITO 유리의 발광면적이 3mm x 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1 x 10-6torr가 되도록 한 후 유기물을 ITO 위에 CuPC(200Å), NPD(400Å), BAlq + B-7(7%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in the vacuum chamber, the base pressure was 1 x 10 -6 torr, and the organics were placed on ITO CuPC (200Å), NPD (400Å), BAlq + B-7 (7%) (200Å), Alq 3 It formed into a film in order of (300 microseconds), LiF (5 microseconds), and Al (1000 microseconds).

0.9mA에서 753cd/m2(6.0V)를 나타내었으며 이때 CIE x=0.652, y=0.362를 나타내었다. 수명(초기휘도의 반)은 2000cd/m2에서 4000시간이었다.753 cd / m 2 (6.0 V) at 0.9 mA, where CIE x == 0.652 and y = 0.362. The lifetime (half the initial luminance) was 4000 hours at 2000 cd / m 2 .

비교예Comparative example

ITO 유리의 발광면적이 3mm x 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1 x 10-6torr가 되도록 한 후 유기물을 ITO 위에 CuPC(200Å), NPD(400Å), BAlq + (btp)2Ir(acac)(7%)(200Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. The substrate was placed in a vacuum chamber and the base pressure was 1 x 10 -6 torr. Organics were then placed on ITO CuPC (200 kPa), NPD (400 kPa), BAlq + (btp) 2 Ir (acac) (7%) ( 200 mV), Alq 3 (300 mV), LiF (5 mV), and Al (1000 mV) in order.

0.9mA에서 780cd/m2(7.5V)를 나타내었으며 이때 CIE x=0.659, y=0.329를 나타내었다. 수명(초기휘도의 반)은 2000cd/m2에서 2500시간이었다.780 cd / m 2 (7.5 V) at 0.9 mA, with CIE x = 0.659 and y = 0.329. The lifetime (half the initial luminance) was 2500 hours at 2000 cd / m 2 .

ITO 유리의 발광면적이 3mm x 3mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1 x 10-6torr가 되도록 한 후 유기물을 ITO 위에 CuPC(200Å), NPD(400Å), CBP + (btp)2Ir(acac)(7%)(200Å), 홀 저지층(100Å), Alq3(300Å), LiF(5Å), Al(1000Å)의 순서로 성막하였다.The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. The substrate was placed in a vacuum chamber and the base pressure was 1 x 10 -6 torr. Organics were then placed on ITO CuPC (200 kPa), NPD (400 kPa), CBP + (btp) 2 Ir (acac) (7%) ( 200 mV), a hole blocking layer (100 mV), Alq 3 (300 mV), LiF (5 mV), and Al (1000 mV) in order.

홀 저지층으로 BAlq를 사용하였을 경우, 0.9mA에서 689cd/m2(8.1V)를 나타내 었으며 이때 CIE x=0.651, y=0.329를 나타내었다. 수명(초기휘도의 반)은 2000cd/m2에서 1600시간이었다.When BAlq was used as the hole blocking layer, 689cd / m 2 (8.1V) was shown at 0.9mA, and CIE x = 0.651 and y = 0.329. The lifetime (half the initial luminance) was 1600 hours at 2000 cd / m 2 .

실시예와 비교예에 따라 제조된 유기 전계발광 소자의 효율특성, 색좌표, 휘도특성과 수명특성을 정리하여 표 1에 나타내었다.Table 1 summarizes the efficiency characteristics, color coordinates, luminance characteristics, and lifetime characteristics of organic electroluminescent devices manufactured according to Examples and Comparative Examples.

디바이스device 전압 (V)Voltage (V) 전류 (mA)Current (mA) 휘도 (cd/m2)Luminance (cd / m 2 ) 전류효율 (cd/A)Current efficiency (cd / A) 전력효율 (lm/W)Power Efficiency (lm / W) CIE (X)CIE (X) CIE (Y)CIE (Y) 수명(h) 초기휘도1/2Life (h) Initial Brightness 1/2 실시예1Example 1 6.66.6 0.90.9 801801 8.018.01 3.813.81 0.6490.649 0.3600.3610.3600.361 51005100 실시예2Example 2 6.36.3 0.90.9 795795 7.957.95 3.963.96 0.6500.650 0.3510.351 48004800 실시예3Example 3 6.16.1 0.90.9 783783 7.837.83 4.034.03 0.6510.651 0.3620.362 55005500 실시예4Example 4 6.06.0 0.90.9 768768 7.687.68 4.024.02 0.6520.652 0.3610.361 40004000 실시예5Example 5 6.06.0 0.90.9 753753 7.537.53 3.943.94 0.6520.652 0.3620.362 40004000 비교예Comparative example 7.57.5 0.90.9 780780 7.807.80 3.273.27 0.6590.659 0.3290.329 25002500

본 발명은 유기전계발광소자의 발광층으로서 상기의 화학식 1의 화합물을 사용함으로써 통상의 유기전계발광소자보다 고색순도, 고휘도, 장수명인 유기 전계 발광 소자를 얻을 수 있다.According to the present invention, an organic electroluminescent device having higher color purity, higher luminance, and longer life than a conventional organic electroluminescent device can be obtained by using the compound of Formula 1 as the light emitting layer of the organic electroluminescent device.

Claims (4)

하기 화학식 1로 표시되는 적색 인광 화합물:Red phosphorescent compound represented by the following formula (1): [화학식 1][Formula 1]
Figure 112006028843713-PAT00024
Figure 112006028843713-PAT00024
 (상기 화학식에서
Figure 112006028843713-PAT00025
은
Figure 112006028843713-PAT00026
이며, R1, R2, R3 및 R4는 수소, C1-C4의 알킬기 및 알콕시기로 이루어진 그룹으로부터 선택되며,
Figure 112006028843713-PAT00027
는 2,4-펜테인다이온, 2,2,6,6,-테트라메틸헵테인-3,5-다이온, 1,3-프로페인다이온, 1,3-부테인다이온, 3,5-헵테인다이온, 1,1,1-트라이플루오로-2,4-펜테인다이온, 1,1,1,5,5,5-헥사플루오로-2,4-펜테인다이온 및 2,2-다이메틸-3,5-헥세인다이온으로부터 선택된다).(In the above formula
Figure 112006028843713-PAT00025
silver
Figure 112006028843713-PAT00026
R 1, R 2, R 3 and R 4 are selected from the group consisting of hydrogen, an alkyl group of C 1 -C 4 and an alkoxy group,
Figure 112006028843713-PAT00027
2,4-pentaneione, 2,2,6,6, -tetramethylheptane-3,5-dione, 1,3-propaneinone, 1,3-butaneinone, 3 , 5-heptanedionone, 1,1,1-trifluoro-2,4-pentaneione, 1,1,1,5,5,5-hexafluoro-2,4-pentane Ions and 2,2-dimethyl-3,5-hexane ions). 양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 음극을 순서대로 적층한 것을 포함하여 이루어지는 유기전계발광소자에 있어서, 제 1 항의 화합물을 발광층의 도펀트로서 0.5중량% - 20중량%를 사용하는 것을 특징으로 하는 유기전계발광소자.An organic electroluminescent device comprising a laminate of an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode in order, wherein the compound of claim 1 is used as a dopant of the light emitting layer in an amount of 0.5% by weight to 20% by weight. An organic light emitting device, characterized in that the use of%. 제 2 항에 있어서,The method of claim 2, Al, Zn 금속 착물 및 카바졸 유도체 중 어느 하나를 발광층의 호스트로 사용하는 것을 특징으로 하는 유기전계발광소자.An organic light emitting display device using any one of Al, Zn metal complex and carbazole derivatives as a host of a light emitting layer. 제 3 항에 있어서,The method of claim 3, wherein Al, Zn 금속 착물의 리간드는 퀴놀기, 바이페닐기, 아이소퀴놀기, 페닐기, 메틸퀴놀기, 다이메틸퀴놀기 및 다이메틸아이소퀴놀기로 이루어지고, 카바졸 유도체는 CBP로 이루어지는 것을 특징으로 하는 유기전계발광소자.The ligand of the Al and Zn metal complexes consists of a quinol group, a biphenyl group, an isoquinol group, a phenyl group, a methylquinol group, a dimethylquinol group and a dimethylisoquinol group, and the carbazole derivative is composed of CBP. Electroluminescent element.
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Cited By (4)

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KR20130065595A (en) * 2011-12-09 2013-06-19 유니버셜 디스플레이 코포레이션 Novel organic light emitting materials
KR20140061390A (en) * 2011-07-08 2014-05-21 시노라 게엠베하 Method of covalently bonding an organic metal complex to a polymer
US10749118B2 (en) 2014-06-26 2020-08-18 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11856805B2 (en) 2018-07-31 2023-12-26 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140061390A (en) * 2011-07-08 2014-05-21 시노라 게엠베하 Method of covalently bonding an organic metal complex to a polymer
KR20130065595A (en) * 2011-12-09 2013-06-19 유니버셜 디스플레이 코포레이션 Novel organic light emitting materials
US10749118B2 (en) 2014-06-26 2020-08-18 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11856805B2 (en) 2018-07-31 2023-12-26 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound

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