KR20070105081A - Organic electroluminescence devices - Google Patents

Organic electroluminescence devices Download PDF

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KR20070105081A
KR20070105081A KR1020060037105A KR20060037105A KR20070105081A KR 20070105081 A KR20070105081 A KR 20070105081A KR 1020060037105 A KR1020060037105 A KR 1020060037105A KR 20060037105 A KR20060037105 A KR 20060037105A KR 20070105081 A KR20070105081 A KR 20070105081A
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layer
transport layer
injection layer
electron
organic electroluminescent
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KR100793795B1 (en
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서정대
김중근
성창제
정현철
빈종관
피성훈
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엘지전자 주식회사
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    • C—CHEMISTRY; METALLURGY
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    • 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
    • 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
    • H10K50/171—Electron injection layers
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    • Y10S428/917—Electroluminescent

Abstract

An organic electroluminescence device is provided to increase the electron transport efficiency, to improve film-forming characteristics, to prevent crystallization, and to realize improved lifespan. An organic electroluminescence device comprises a cathode, a hole injection layer, a hole transport layer, a light emitting layer(host+dopant), an electron transport layer, an electron injection layer, and an anode, stacked successively, wherein a compound represented by the following formula 1 is used in the electron transport layer and the electron injection layer. In formula 1, R1, R2 and R3 are the same or different, and represent a substituted or non-substituted aromatic group, heterocyclic group, aliphatic group and H.

Description

유기전계발광소자{Organic electroluminescence devices}Organic electroluminescence devices

도 1은 본 발명의 실시예에서 사용되는 화합물인 NPD, 구리(II)프탈로시아닌(CuPc), Alq3 및 GD-1의 구조식을 나타낸다.1 shows structural formulas of NPD, copper (II) phthalocyanine (CuPc), Alq 3 and GD-1, which are compounds used in Examples of the present invention.

본 발명은 유기전계발광소자에 관한 것이다. 보다 구체적으로, 본 발명은 본 발명은 본 발명은 양극, 정공주입층, 정공수송층, 발광층(호스트+도펀트), 전자수송층, 전자주입층 및 음극을 순서대로 적층한 것을 포함하여 이루어지고, 하기 화학식 1의 화합물을 전자수송층 및 전자주입층으로 사용하는 유기전계발광소자에 관한 것이다.The present invention relates to an organic electroluminescent device. More specifically, the present invention is made of the present invention comprises a laminate of an anode, a hole injection layer, a hole transport layer, a light emitting layer (host + dopant), an electron transport layer, an electron injection layer and a cathode in order, and the following formula An organic electroluminescent device using the compound of 1 as an electron transport layer and an electron injection layer.

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) 사이 에 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,An organic electroluminescent device is a device that emits light by dissipating electrons and holes after pairing when an electric charge is injected into an organic film formed between an electron injection electrode (cathode) and a 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 도펀트(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) as a common organic light emitting layer for light emitting tris (8-hydroxy-quinol-rate) aluminum (Alq 3) (tris (8 -hydroxy-quinolatealuminum) roneun 30 ~ 60nm thick and depositing approximately a dopant (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.

본 발명은 유기전계발광소자의 전자수송층 및 전자주입층으로 사용되는 화학식 1의 화합물을 합성하여 소자의 전자전달효율을 높이고 양호한 막 형성과 결정화를 방지하여 장수명의 유기전계발광소자를 제공하는데 그 목적이 있다.The present invention synthesizes the compound of Formula 1 used as the electron transport layer and the electron injection layer of the organic light emitting device to increase the electron transfer efficiency of the device and to prevent the formation and crystallization of the device to provide a long life of the organic light emitting device There is this.

본 발명의 유기발광소자는 양극, 정공주입층, 정공수송층, 발광층(호스트+도펀트), 전자수송층, 전자주입층 및 음극을 순서대로 적층한 것을 포함하여 이루어지고, 하기 화학식 1의 화합물을 전자수송층 및 전자주입층으로 사용한다.The organic light emitting device of the present invention comprises a laminate of an anode, a hole injection layer, a hole transport layer, a light emitting layer (host + dopant), an electron transport layer, an electron injection layer and a cathode in order, the compound of formula 1 electron transport layer And an electron injection layer.

Figure 112006028844242-PAT00002
Figure 112006028844242-PAT00002

상기 화학식 1에서 R1, R2 및 R3는 서로 같은 구조이거나 다른 구조이며, 각각 독립적으로 치환되거나 치환되지 않은 방향족 그룹, 이형고리 그룹, 지방족 그룹 및 수소로부터 선택된다.In Formula 1, R1, R2, and R3 have the same or different structures, and are each independently selected from a substituted or unsubstituted aromatic group, heterocyclic group, aliphatic group, and hydrogen.

상기 치환되거나 치환되지 않은 R1, R2 및 R3는 페닐(phenyl), 바이페닐(biphenyl), 파이리디닐(pyridyl), 나프틸(naphthyl), 퀴놀린(quinoline), 이소퀴놀린(isoquinoline), 플로렌(fluorene), 터페닐(terphenyl), 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(i-propyl), 할로겐(halogen), 페난스롤린(phenanthroline), 퀴녹살린(quinoxaline), 터피리딘(terpyridine) 및 아마이드(amide) 등으로부터 선택될 수 있다.The substituted or unsubstituted R1, R2 and R3 are phenyl, biphenyl, pyridinyl, naphthyl, quinoline, isoquinoline, isolene fluorene, terphenyl, methyl, ethyl, propyl, isopropyl, halogen, phenanthroline, quinoxaline, Terpyridine, amide and the like.

상기 R1, R2 및 R3의 치환체는 아릴(aryl), 알킬(alkyl), 아릴옥시(aryloxy), 알콕시(alkoxy), 알릴아미노(allylamino), 알킬아미노(alkylamino), 아미노(amino), 할로겐(halogen), 시아노(cyano), 피리딜(pyridyl), 퀴놀린(quinoline) 및 이소퀴놀린 (isoquinoline) 그룹으로부터 선택될 수 있으며, R1, R2 및 R3의 구체적인 치환체는 각각 독립적으로 페닐(phenyl), 바이페 닐(biphenyl), 트리페닐메틸(triphenylmethyl), 페닐에틸리덴(phenylethylidene), 디페닐에틸리덴(diphenylethylidene), 페닐메틸리다인(phenylmethylidyne), 페녹시(phenoxy), 톨리옥시(tolyoxy), 비닐(vinyl), 알데하이드(aldehyde), 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(i-propyl), 뷰틸(t-butyl), 사이클로헥실(cyclohexyl), 디페닐아미노(diphenylamino), 모폴린(morpholine), 메톡시(methoxy), 에톡시(ethoxy), 프로폭시(propoxy), 부톡시(butoxy), 디메틸아미노(dimethylamino), 디페닐아미노(diphenylamino), 불소 및 염소로 이루어지는 그룹으로부터 선택될 수 있다.Substituents of R1, R2 and R3 may be aryl, alkyl, aryloxy, alkoxy, allylamino, alkylamino, aminoamino, halogen ), Cyano, pyridyl, quinoline and isoquinoline, and specific substituents of R1, R2 and R3 are each independently phenyl, bipe Biphenyl, triphenylmethyl, phenylethylidene, diphenylethylidene, phenylmethylidyne, phenmethyl, tolyoxy, vinyl (vinyl), aldehyde (methyl), ethyl (ethyl), propyl (isopropyl), isopropyl (i-propyl), butyl (t-butyl), cyclohexyl, diphenylamino ), Morpholine, methoxy, ethoxy, propoxy, butoxy, dimethylamino, di Carbonyl-amino (diphenylamino), it may be selected from the group consisting of fluorine and chlorine.

상기 화학식 1의 R1, R2 및 R3는 하기 화합물로부터 선택될 수 있다.R1, R2 and R3 of Formula 1 may be selected from the following compounds.

Figure 112006028844242-PAT00003
Figure 112006028844242-PAT00003

상기 화합물에서 R1-R6는 R1은 CH3; R2, R3, R4, R5 및 R6는 H; R2는 CH3; R1, R3, R4, R5 및 R6는 H; R3는 CH3; R1, R2, R4, R5 및 R6는 H; R4는 CH3; R1, R2, R3, R5 및 R6는 H; R5는 CH3; R1, R2, R3, R4 및 R6는 H; R6는 CH3; R1, R2, R3, R4, R5 및 R6는 H와 같이 선택될 수 있다.R 1 -R 6 in the compound, R 1 is CH 3 ; R 2 , R 3 , R 4 , R 5 and R 6 are H; R 2 is CH 3 ; R 1 , R 3 , R 4 , R 5 and R 6 are H; R 3 is CH 3 ; R 1 , R 2 , R 4 , R 5 and R 6 are H; R 4 is CH 3 ; R 1 , R 2 , R 3 , R 5 and R 6 are H; R 5 is CH 3 ; R 1 , R 2 , R 3 , R 4 and R 6 are H; R 6 is CH 3 ; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may be selected as H.

상기 전자수송층 및 전자주입층은 하기 화합물로부터 선택될 수 있다.The electron transport layer and the electron injection layer may be selected from the following compounds.

Figure 112006028844242-PAT00004
Figure 112006028844242-PAT00004

Figure 112006028844242-PAT00005
Figure 112006028844242-PAT00005

Figure 112006028844242-PAT00006
Figure 112006028844242-PAT00007
Figure 112006028844242-PAT00006
Figure 112006028844242-PAT00007

이하에서 본 발명의 유기전계발광소자의 전자수송층 및 전자주입층에 사용되는 E-1 및 E-18로 나타낸 화합물을 예로 들어 합성 방법을 설명하기로 한다.Hereinafter, the synthesis method will be described with reference to the compounds represented by E-1 and E-18 used in the electron transport layer and the electron injection layer of the organic light emitting device of the present invention.

합성예Synthesis Example

1. E-1의 합성1. Synthesis of E-1

Figure 112006028844242-PAT00008
Figure 112006028844242-PAT00008

2구 둥근 바닥 플라스크에 1,6-디브로모파이렌(1,6-Dibromopyrene)(3g, 0.0083mol), 피리딘페닐아민(pyridinephenylamine)(4.38g, 0.025mol), BINAP([2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl])(0.052g, 1% mol), Pd(OAC)2[Palladium(∥)acetate](0.019g, 1% mol)과 NaOtBu[Sodium tert-butoxide](2.3g, 0.029mol)를 톨루엔(80mL)에 녹인 후 24시간 환류한다. 반응이 종결되면 둥근 바닥 플라스크를 냉각시키고, 반응 용매인 톨루엔 40mL를 제거한 후 여기에 메탄올(100mL)을 첨가하면 침전물이 생기게 된다. 이것을 필터하고 다이클로로메탄과 메탄올을 이용하여 재결정을 하면 E-18의 전자수송 및 주입물질을 얻을 수 있다1,6-Dibromopyrene (3 g, 0.0083 mol), pyridinephenylamine (4.38 g, 0.025 mol), BINAP ([2,2 ') in a two-neck round bottom flask -Bis (diphenylphosphino) -1,1'-binaphthyl]) (0.052g, 1% mol), Pd (OAC) 2 [Palladium (∥) acetate] (0.019g, 1% mol) and NaOtBu [Sodium tert-butoxide ] (2.3 g, 0.029 mol) is dissolved in toluene (80 mL) and refluxed for 24 hours. At the end of the reaction, the round bottom flask was cooled, 40 mL of toluene was removed, and methanol (100 mL) was added thereto to form a precipitate. By filtering this and recrystallization with dichloromethane and methanol, electron transport and injection material of E-18 can be obtained.

2. E-18의 합성2. Synthesis of E-18

Figure 112006028844242-PAT00009
Figure 112006028844242-PAT00009

2구 둥근 바닥 플라스크에 1,6-디브로모-3,8-다이페닐파이렌(1,6-Dibromo-3,8-diphenylpyrene)(3.6g, 0.0083mol), 피리딘페닐아민(pyridinephenylamine)(4.38g, 0.025mol), BINAP([2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl])(0.052g, 1% mol), Pd(OAC)2[Palladium(∥)acetate](0.019g, 1% mol)과 NaOtBu[Sodium tert-butoxide](2.3g, 0.029mol)를 톨루엔(80mL)에 녹인 후 24시간 환류한다. 반응이 종결되면 둥근 바닥 플라스크를 냉각시키고, 반응 용매인 톨루엔 40mL를 제거한 후 여기에 메탄올(100mL)을 첨가하면 침전물이 생기게 된다. 이것을 필터하고 다이클로로메탄과 메탄올을 이용하여 재결정을 하면 우리가 원하는 E-18의 전자수송 및 주입물질을 얻을 수 있다.In a two-necked round bottom flask, 1,6-Dibromo-3,8-diphenylpyrene (3.6 g, 0.0083 mol), pyridinephenylamine ( 4.38 g, 0.025 mol), BINAP ([2,2'-Bis (diphenylphosphino) -1,1'-binaphthyl]) (0.052g, 1% mol), Pd (OAC) 2 [Palladium (∥) acetate] ( 0.019 g, 1% mol) and NaOtBu [Sodium tert-butoxide] (2.3 g, 0.029 mol) are dissolved in toluene (80 mL) and refluxed for 24 hours. At the end of the reaction, the round bottom flask was cooled, 40 mL of toluene was removed, and methanol (100 mL) was added thereto to form a precipitate. Filtering this and recrystallization with dichloromethane and methanol gives us the E-18 transport and injection material we want.

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

실시예Example

실시예 1Example 1

ITO glass의 발광 면적이 3mm X 3mm 크기가 되도록 patterning한 후 세정하 였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1x10-6torr가 되도록 한 후 유기물을 ITO위에 CuPc(650Å)/NPD(400Å)/Alq3(200Å) + GD-1 (1%)(50Å)/E-1(350Å)/LiF(5Å)/Al(1000Å)의 순서로 성막하였다. The light emitting area of the ITO glass was patterned to be 3mm × 3mm and washed. After mounting the substrate in the vacuum chamber, the basic pressure is 1x10 -6 torr and the organic material is placed on ITO CuPc (650kW) / NPD (400kW) / Alq3 (200kW) + GD-1 (1%) (50kW) / E The film was formed in the order of -1 (350 kV) / LiF (5 kV) / Al (1000 kV).

0.9 mA에서 1622cd/m2(6.0V)를 나타내었으며 이때 CIE x = 0.299, y = 0.620을 나타내었다.1622 cd / m 2 (6.0 V) at 0.9 mA with CIE x = 0.299, y = 0.620.

실시예 2Example 2

ITO glass의 발광 면적이 3mm X 3mm 크기가 되도록 patterning한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1x10-6torr가 되도록 한 후 유기물을 ITO위에 CuPc(650Å)/NPD(400Å)/Alq3(200Å) + GD-1 (1%)(50Å)/E-8(350Å)/LiF(5Å)/Al(1000Å)의 순서로 성막하였다. The light emitting area of the ITO glass was patterned to have a size of 3mm × 3mm and then washed. After mounting the substrate in the vacuum chamber, the basic pressure is 1x10 -6 torr, and the organic material is placed on the ITO. The film was formed in the order of -8 (350 Pa) / LiF (5 Pa) / Al (1000 Pa).

0.9 mA에서 1630cd/m2(5.9V)를 나타내었으며 이때 CIE x = 0.299, y = 0.621을 나타내었다.1630 cd / m 2 (5.9 V) at 0.9 mA, with CIE x = 0.299 and y = 0.621.

실시예 3 Example 3

ITO glass의 발광 면적이 3mm X 3mm 크기가 되도록 patterning한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1x10-6torr가 되도록 한 후 유기물을 ITO위에 CuPc(650Å)/NPD(400Å)/Alq3(200Å) + GD-1 (1%)(50Å)/E-14(350Å)/LiF(5Å)/Al(1000Å)의 순서로 성막하였다. The light emitting area of the ITO glass was patterned to have a size of 3mm × 3mm and then washed. After mounting the substrate in the vacuum chamber, the basic pressure is 1x10 -6 torr, and the organic material is placed on the ITO. It formed into a film in order of -14 (350 kPa) / LiF (5 kPa) / Al (1000 kPa).

0.9 mA에서 1506cd/m2(6.6V)를 나타내었으며 이때 CIE x = 0.300, y = 0.624를 나타내었다.At 0.9 mA, this value was 1506 cd / m 2 (6.6 V), with CIE x = 0.300 and y = 0.624.

실시예 4  Example 4

ITO glass의 발광 면적이 3mm X 3mm 크기가 되도록 patterning한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1x10-6torr가 되도록 한 후 유기물을 ITO위에 CuPc(650Å)/NPD(400Å)/Alq3(200Å) + GD-1 (1%)(50Å)/E-16(350Å)/LiF(5Å)/Al(1000Å)의 순서로 성막하였다. The light emitting area of the ITO glass was patterned to have a size of 3mm × 3mm and then washed. After mounting the substrate in the vacuum chamber, the basic pressure is 1x10 -6 torr, and the organic material is placed on the ITO. The film was formed in the order of -16 (350 Pa) / LiF (5 Pa) / Al (1000 Pa).

0.9 mA에서 1324cd/m2(6.8V)를 나타내었으며 이때 CIE x = 0.296, y = 0.618를 나타내었다.1324 cd / m 2 (6.8 V) at 0.9 mA, with CIE x = 0.296, y = 0.618.

비교예Comparative example

ITO glass의 발광 면적이 3mm X 3mm 크기가 되도록 patterning한 후 세정하였다. 기판을 진공 챔버에 장착한 후 기본 압력이 1X10-6torr가 되도록 한 후 유기물을 ITO위에 CuPc(650Å)/NPD(400Å)/Alq3(200Å) + GD-1 (1%)(50Å)/Alq3(350Å)/LiF(5Å)/Al(1000Å)의 순서로 성막하였다. The light emitting area of the ITO glass was patterned to have a size of 3mm × 3mm and then washed. After mounting the substrate in the vacuum chamber, the basic pressure is 1X10-6torr, and the organic material is placed on ITO CuPc (650Å) / NPD (400Å) / Alq3 (200Å) + GD-1 (1%) (50Å) / Alq3 ( The film was formed in the order of 350 Pa) / LiF (5 Pa) / Al (1000 Pa).

0.9mA에서 1251cd/m2(6.5V)를 나타내었으며 이때 CIE x = 0.307, y = 0.612를 나타내었다.1251 cd / m 2 (6.5 V) at 0.9 mA, where CIE x = 0.307 and y = 0.612.

본 발명은 유기전계발광소자의 전자수송층 및 전자주입층으로서 상기의 화학 식 1의 화합물을 사용함으로써 소자의 전자전달효율을 높이고 양호한 막형성과 결정화를 방지하여 장수명의 유기전계발광소자를 얻을 수 있다.According to the present invention, by using the compound of Chemical Formula 1 as the electron transporting layer and the electron injection layer of the organic light emitting device, it is possible to increase the electron transfer efficiency of the device and to prevent good film formation and crystallization, thereby obtaining a long life organic light emitting device. .

Claims (4)

양극, 정공주입층, 정공수송층, 발광층(호스트+도펀트), 전자수송층, 전자주입층, 음극을 순서대로 적층한 것을 포함하여 이루어지고, 하기 화학식 1의 화합물을 전자수송층 및 전자주입층으로 사용하는 유기전계발광소자: Comprising a laminate of an anode, a hole injection layer, a hole transport layer, a light emitting layer (host + dopant), an electron transport layer, an electron injection layer, a cathode in order, using a compound of the formula 1 as an electron transport layer and an electron injection layer Organic electroluminescent device: [화학식 1][Formula 1]
Figure 112006028844242-PAT00010
Figure 112006028844242-PAT00010
 (상기 식에서 R1, R2 및 R3는 서로 같은 구조이거나 다른 구조이며, 각각 독립적으로 치환되거나 치환되지 않은 방향족 그룹, 이형고리 그룹, 지방족 그룹 및 수소로부터 선택된다).(Wherein R 1, R 2 and R 3 are the same or different structures from each other, each independently selected from substituted or unsubstituted aromatic groups, heterocyclic groups, aliphatic groups and hydrogen). 제 1 항에 있어서,The method of claim 1, 치환되거나 치환되지 않은 R1, R2 및 R3는 페닐(phenyl), 바이페닐(biphenyl), 파이리디닐(pyridyl), 나프틸(naphthyl), 퀴놀린(quinoline), 이소퀴놀린(isoquinoline), 플로렌(fluorene), 터페닐(terphenyl), 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(i-propyl), 할로겐(halogen), 페난스롤린(phenanthroline),퀴녹살린(quinoxaline), 터피리딘(terpyridine) 및 아미 드(amide)로부터 선택되는 유기전계발광소자.Substituted or unsubstituted R1, R2 and R3 are phenyl, biphenyl, pyridinyl, naphthyl, quinoline, isoquinoline, fluorene ), Terphenyl, methyl, ethyl, propyl, isopropyl, halogen, phenanthroline, quinoxaline, ter Organic electroluminescent device selected from pyridine (terpyridine) and amide (amide). 제 2 항에 있어서,The method of claim 2, R1, R2 및 R3의 치환체는 아릴(aryl), 알킬(alkyl), 아릴옥시(aryloxy), 알콕시(alkoxy), 알릴아미노(allylamino), 알킬아미노(alkylamino), 아미노(amino), 할로겐(halogen), 시아노(cyano), 피리딜(pyridyl), 퀴놀린(quinoline) 및 이소퀴놀린(isoquinoline)그룹으로부터 선택되는 유기전계발광소자.Substituents for R1, R2 and R3 are aryl, alkyl, aryloxy, alkoxy, allylamino, alkylamino, amino, halogen , An organic electroluminescent device selected from cyano, pyridyl, quinoline and isoquinoline groups. 제 3 항에 있어서,The method of claim 3, wherein R1, R2 및 R3의 치환체는 각각 독립적으로 페닐(phenyl), 바이페닐(biphenyl), 트리페닐메틸(triphenylmethyl), 페닐에틸리덴(phenylethylidene), 디페닐에틸리덴(diphenylethylidene), 페닐메틸리다인(phenylmethylidyne), 페녹시(phenoxy), 톨리옥시(tolyoxy), 비닐(vinyl), 알데하이드(aldehyde), 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(i-propyl), 뷰틸(t-butyl), 사이클로헥실(cyclohexyl), 디페닐아미노(diphenylamino), 모폴린(morpholine), 메톡시(methoxy), 에톡시(ethoxy), 프로폭시(propoxy), 부톡시(butoxy), 디메틸아미노(dimethylamino), 디페닐아미노(diphenylamino), 불소 및 염소로 이루어지는 그룹으로부터 선택되는 유기전계발광소자.Substituents for R1, R2 and R3 are each independently phenyl, biphenyl, triphenylmethyl, phenylethylidene, diphenylethylidene, or phenylmethyllidine (phenylmethylidyne), phenoxy, tolyoxy, vinyl, aldehyde, methyl, ethyl, propyl, isopropyl, butyl (t-butyl), cyclohexyl, diphenylamino, morpholine, methoxy, ethoxy, propoxy, butoxy, dimethyl An organic electroluminescent device selected from the group consisting of amino (dimethylamino), diphenylamino, fluorine and chlorine.
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