KR20000014145A - Organic electroluminescent device - Google Patents

Organic electroluminescent device Download PDF

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KR20000014145A
KR20000014145A KR1019980033375A KR19980033375A KR20000014145A KR 20000014145 A KR20000014145 A KR 20000014145A KR 1019980033375 A KR1019980033375 A KR 1019980033375A KR 19980033375 A KR19980033375 A KR 19980033375A KR 20000014145 A KR20000014145 A KR 20000014145A
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organic
aromatic ring
light emitting
formula
electrode
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KR100282334B1 (en
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오형윤
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구자홍
엘지전자 주식회사
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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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H10K2102/361—Temperature
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

PURPOSE: An organic EL(electroluminescent) device is provided to elevate glass transient temperature by forming an organic luminescent layer having a chemical formula 1 between a first and second electrodes, thereby to enhance the life of the device. CONSTITUTION: In an organic EL(electroluminescent) device consisted of an organic function layer comprising at least one organic luminescent layer between a first electrode and a second electrode. The organic luminescent layer is consisted of the material having a chemical formula 1. In the chemical formula 1, A is a material selected from alkane, alkene, ether, aromatic ring and cyclo alkane, R1, R2 are the material selected from aromatic ring, and n is 1, 2, 3, 4, 5.

Description

유기 ＥＬ 소자Organic EL element

본 발명은 디스플레이 소자에 관한 것으로, 특히 유기 EL 소자에 관한 것이다.TECHNICAL FIELD The present invention relates to display elements, and more particularly to organic EL elements.

최근에는 유기 발광 다이오드(Light Emitting Diode: LED)라고도 불리는 유기 EL 소자의 기술이 빠른 속도로 발전하고 있으며, 이미 시제품이 발표되었다.In recent years, the technology of organic EL elements, also called organic light emitting diodes (LEDs), is rapidly developing, and prototypes have already been announced.

유기 EL 소자는 매우 얇고, 매트릭스 형태로 어드레스 할 수 있으며, 15V 이하의 낮은 전압으로도 구동이 가능한 장점이 있다.The organic EL device is very thin, can be addressed in a matrix form, and can be driven at a low voltage of 15V or less.

또한, 유기 EL 소자는 넓은 시야각과 플라스틱과 같이 휠 수 있는(flexible) 투명기판 위에도 형성할 수 있어 차세대 평판 디스플레이(Flat Panel Display: FPD)에 적합한 소자이며, 잘 알려진 LCD (Liquid Crystal Display)에 비해 백라이트(backlight)가 필요치 않으므로 전력 소모가 적은 장점도 있다.In addition, organic EL devices can be formed on flexible transparent substrates such as wide viewing angles and plastics, making them suitable for next-generation flat panel displays (FPDs), and compared to well-known liquid crystal displays (LCDs). There is no need for backlight, which also has the advantage of low power consumption.

이와 같은 장점을 갖는 유기 EL 소자는 일반적으로 무기 EL 소자와는 동작 원리 면에서 큰 차이가 있다.The organic EL device having such an advantage generally has a large difference in operation principle from that of the inorganic EL device.

무기 EL 소자는 높은 전계에 의해 가속된 전자가 발광체(luminescent impurity)에 충돌, 여기 시키고 여기된 발광체가 기저 상태로 떨어지면서 발광하는데 반해, 유기 EL 소자는 음극과 양극으로부터 각각 주입된 전자와 정공이 결합하여 생성된 엑시톤(exciton)이 여기상태로부터 기저상태로 떨어지면서 발광한다.Inorganic EL devices emit electrons that are accelerated by high electric fields and collide with the luminescent impurity, and the excited light emitters fall to the ground state, whereas organic EL devices emit electrons and holes respectively injected from the cathode and anode. The excitons generated by the coupling emit light while falling from the excited state to the ground state.

일반적으로 유기 EL로 풀-컬러(full-color)를 구현하기 위해서는 그린(green), 레드(red), 블루(blue)의 3가지 빛을 내는 발광 소자를 필요로 한다.In general, in order to implement full-color with an organic EL, a light emitting device emitting three types of light of green, red, and blue is required.

여기서, 그린, 레드는 Alq3에 여러 가지 염료(dye)를 도핑함으로써 실현할 수가 있으나 블루의 경우는 밴드 갭(band gap)에너지가 크기 때문에 근본적으로 새로운 발광층을 필요로 한다.Here, green and red can be realized by doping various dyes to Alq 3 , but in the case of blue, the band gap energy is large, and thus a new light emitting layer is required.

따라서, 많은 연구소나 업체에서 청색 발광체를 개발하기 위한 연구가 진행되어 왔으며 미국 특허 5516577에는 다양한 청색 물질을 개발하여 청색 염료를 도핑함으로써 높은 휘도를 얻었다.Therefore, many research institutes and companies have been researched to develop a blue light emitter, US patent 5516577 has developed a variety of blue materials to obtain a high luminance by doping the blue dye.

그러나, 수명에 가장 큰 영향을 미치는 유리전이온도에 있어 불리한 단점이 있다.However, there are disadvantages in the glass transition temperature which has the greatest influence on the lifetime.

따라서, 높은 열안정성을 지닌 청색 발광 물질의 개발이 필요하다.Therefore, there is a need for the development of a blue light emitting material having high thermal stability.

본 발명은 상기와 같은 문제들을 해결하기 위한 것으로 우수한 청색 물질을 소자에 도입하여 열안정성을 높이고 수명을 향상시킬 수 있는 유기 EL 소자를 제공하는데 그 목적이 있다.SUMMARY OF THE INVENTION The present invention has been made to solve the above problems, and an object thereof is to provide an organic EL device capable of improving thermal stability and lifespan by introducing an excellent blue material into the device.

도 1은 본 발명에 따른 유기 EL 소자의 구조를 보여주는 단면도1 is a cross-sectional view showing the structure of an organic EL device according to the present invention

도면의 주요부분에 대한 부호의 설명Explanation of symbols for main parts of the drawings

21 : 기판 22 : 제 1 전극21 substrate 22 first electrode

23 : 정공주입층 24 : 정공수송층23: hole injection layer 24: hole transport layer

25 : 유기발광층 26 : 제 2 전극25 organic light emitting layer 26 second electrode

본 발명에 따른 유기 EL 소자의 주요 특징은 제 1 전극과 제 2 전극 사이에 형성된 적어도 하나의 유기발광층을 포함하는 유기기능층으로 이루어진 유기 EL 소자에 있어서, 유기발광층이 하기 화학식 1의 구조를 갖는 물질로 이루어지는데 있다.A main feature of the organic EL device according to the present invention is an organic EL device comprising an organic functional layer including at least one organic light emitting layer formed between a first electrode and a second electrode, wherein the organic light emitting layer has a structure of Formula 1 It consists of matter.

여기서, A는 알칸(alkane), 알켄(alkene), 이써(ether), 아로매틱 링(aromatic ring), 시클로 알칸(cyclo alkane)으로부터 선택된 물질이고,Here, A is a material selected from alkane, alkene, ether, aromatic ring, cyclo alkane,

R1, R2는 H, 아로매틱 링(aromatic ring)으로부터 선택된 물질이며,R 1 , R 2 is a material selected from H, aromatic ring,

n은 1, 2, 3, 4, 5이다.n is 1, 2, 3, 4, 5.

본 발명의 다른 특징은 상기 화학식 1에서, A물질은 F, Cl 중 어느 하나가 치환되며, A물질의 아로매틱 링은 벤젠, 나프틸기 중 어느 하나가 사용되며, R1, R2의 아로매틱 링은 페닐, 나프틸, N-methylcarbazol, N-ethylcarbazol 중 어느 하나가 사용되는데 있다.Another characteristic of the present invention is that in Formula 1, the A material is substituted with any one of F, Cl, the aromatic ring of the A material is any one of benzene, naphthyl group is used, the aromatic of R 1 , R 2 The ring may be any one of phenyl, naphthyl, N-methylcarbazol and N-ethylcarbazol.

본 발명의 또 다른 특징은 유기발광층이 하기 화학식 2, 화학식 3의 구조를 갖는 물질들 중 어느 하나로 이루어지는데 있다.Another feature of the present invention is that the organic light emitting layer is made of any one of materials having the structures of Formulas 2 and 3.

여기서, n은 2, 3, 4이다.Where n is 2, 3, 4.

상기와 같은 특징을 갖는 본 발명에 따른 유기 EL 소자를 첨부된 도면을 참조하여 설명하면 다음과 같다.Hereinafter, an organic EL device according to the present invention having the above characteristics will be described with reference to the accompanying drawings.

도 1은 본 발명에 따른 유기 EL 소자의 구조를 보여주는 단면도로서, 다음과 같은 적층 구조로 이루어진다.1 is a cross-sectional view showing a structure of an organic EL device according to the present invention, and has a laminated structure as follows.

(1)투명 기판(21) 위에 약 100nm 두꼐의 제 1 전극(22)을 형성한다.(1) The first electrode 22 having a thickness of about 100 nm is formed on the transparent substrate 21.

(2)그 위에 약 10nm ∼ 20nm 두께의 copper phthalocyanine(CuPc)로 이루어진 정공주입층(23)을 입힌다.(2) A hole injection layer 23 made of copper phthalocyanine (CuPc) having a thickness of about 10 nm to 20 nm is coated thereon.

(3)다음으로 약 30nm ∼ 50nm 두께의 N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'- biphenyl) -4,4'-diamine (TPD)로 이루어진 정공수송층(24)을 형성한다.(3) followed by N, N'-diphenyl-N, N'-bis (3-methylphenyl)-(1,1'-biphenyl) -4,4'-diamine (TPD) with a thickness of about 30 nm to 50 nm. The hole transport layer 24 is formed.

(4)이어, 정공수송층(24) 위에 약 40nm ∼ 60nm 두께의 하기 화학식 1로 이루어진 유기발광층(25)을 증착한다.(4) Then, the organic light emitting layer 25 having the thickness of about 40 nm to 60 nm is deposited on the hole transport layer 24.

화학식 1Formula 1

여기서, A는 알칸(alkane), 알켄(alkene), 이써(ether), 아로매틱 링(aromatic ring), 시클로 알칸(cyclo alkane)으로부터 선택된 물질이고, R1, R2는 H, 아로매틱 링(aromatic ring)으로부터 선택된 물질이며, n은 1, 2, 3, 4, 5이다.Here, A is a material selected from alkane, alkene, ether, aromatic ring, cyclo alkane, R 1 , R 2 is H, aromatic ring ( aromatic ring) and n is 1, 2, 3, 4, 5.

또한, A물질은 F, Cl 등이 치환될 수도 있으며, A물질의 아로매틱 링은 벤젠, 나프틸기 등이 사용될 수 있다.In addition, the A material may be substituted with F, Cl, etc., the aromatic ring of the A material may be used a benzene, naphthyl group and the like.

그리고, R1, R2의 아로매틱 링은 페닐, 나프틸, N-methylcarbazol, N-ethylcarbazol 등이 사용될 수도 있다.As the aromatic ring of R 1 and R 2 , phenyl, naphthyl, N-methylcarbazol, N-ethylcarbazol, or the like may be used.

상기 화학식 1의 구조를 갖는 물질들 중에서는 하기 화학식 2와 화학식 3의 구조를 갖는 물질들이 더 좋다.Among the materials having the structure of Formula 1, materials having the structures of Formula 2 and Formula 3 are better.

화학식 2Formula 2

화학식 2Formula 2

여기서, n은 2, 3, 4이다.Where n is 2, 3, 4.

이와 같이 유기발광층(24)으로 상기와 같은 물질들을 선택한 이유는 다음과 같다.The reason why the above materials are selected as the organic light emitting layer 24 is as follows.

일반적으로 유리 전이 온도를 결정하는 것은 유기 EL 소자에 있어서는 분자량이다.Generally, it is molecular weight in organic electroluminescent element to determine glass transition temperature.

물론 수소 결합 등을 통하여 높은 유리 전이 온도를 가질 수 있으나 이럴 경우 하이드록실기를 통한 분자간 상호 작용에 의하여 비발광 전이로의 천이로 효율이 크게 감소한다.Of course, it may have a high glass transition temperature through hydrogen bonding, but in this case the efficiency is greatly reduced by the transition to the non-luminescent transition by the intermolecular interaction through the hydroxyl group.

따라서, 성능을 유지시키면서 유리 전이 온도를 높이는 방법은 분자간의 상호 작용을 크게 줄이면서 분자량을 높이는 방법이다.Therefore, the method of increasing the glass transition temperature while maintaining the performance is a method of increasing the molecular weight while greatly reducing the interaction between molecules.

즉, 상기 화학식 1과 같이 청색 발광 유닛(unit) 두 개를 알킬기 또는 페닐기를 이용하여 다리 결합시킴으로써 유리 전이 온도를 높였다.That is, as shown in Formula 1, two blue light emitting units were bridged using an alkyl group or a phenyl group to increase the glass transition temperature.

(5)그리고, 유기발광층(25) 위에 약 100nm ∼ 200nm 두께의 제 2 전극(26)을 입힌다.(5) Then, the second electrode 26 having a thickness of about 100 nm to 200 nm is coated on the organic light emitting layer 25.

경우에 따라 제 2 전극(26)과 유기발광층(25) 사이에 CuPc와 같은 접착층이 형성할 수도 있다.In some cases, an adhesive layer such as CuPc may be formed between the second electrode 26 and the organic light emitting layer 25.

본 발명에 따른 유기 EL 소자에 있어서는 다음과 같은 효과가 있다.The organic EL device according to the present invention has the following effects.

청색 발광 유닛 두 개를 알킬기 또는 페닐기를 이용하여 다리 결합시킴으로써 유리 전이 온도를 높여 소자의 수명을 크게 증가시킨다.The two blue light emitting units are bridged using an alkyl group or a phenyl group to increase the glass transition temperature, thereby greatly increasing the life of the device.

Claims (3)

제 1 전극과 제 2 전극 사이에 형성된 적어도 하나의 유기발광층을 포함하는 유기기능층으로 이루어진 유기 EL 소자에 있어서,In an organic EL device comprising an organic functional layer comprising at least one organic light emitting layer formed between a first electrode and a second electrode, 상기 유기발광층은 하기 화학식 1의 구조를 갖는 물질로 이루어지는 것을 특징으로 하는 유기 EL 소자.The organic light emitting layer is an organic EL device, characterized in that made of a material having a structure of formula (1). 화학식 1Formula 1 여기서, A는 알칸(alkane), 알켄(alkene), 이써(ether), 아로매틱 링(aromatic ring), 시클로 알칸(cyclo alkane)으로부터 선택된 물질이고,Here, A is a material selected from alkane, alkene, ether, aromatic ring, cyclo alkane, R1, R2는 H, 아로매틱 링(aromatic ring)으로부터 선택된 물질이며,R 1 , R 2 is a material selected from H, aromatic ring, n은 1, 2, 3, 4, 5이다.n is 1, 2, 3, 4, 5. 제 1 항에 있어서, 상기 A물질은 F, Cl 중 어느 하나가 치환되며, A물질의 아로매틱 링은 벤젠, 나프틸기 중 어느 하나가 사용되며, R1, R2의 아로매틱 링은 페닐, 나프틸, N-methylcarbazol, N-ethylcarbazol 중 어느 하나가 사용되는 것을 특징으로 하는 유기 EL 소자.The method of claim 1, wherein the A material is substituted with any one of F, Cl, the aromatic ring of the A material is any one of benzene, naphthyl group is used, the aromatic ring of R 1 , R 2 is phenyl, An organic EL device comprising any one of naphthyl, N-methylcarbazol, and N-ethylcarbazol. 제 1 항에 있어서, 상기 유기발광층은 하기 화학식 2, 화학식 3의 구조를 갖는 물질들 중 어느 하나로 이루어지는 것을 특징으로 하는 유기 EL 소자.The organic EL device of claim 1, wherein the organic light emitting layer is made of any one of materials having the structures of Formulas 2 and 3. 화학식 2Formula 2 화학식 3Formula 3 여기서, n은 2, 3, 4이다.Where n is 2, 3, 4.
KR1019980033375A 1998-08-14 1998-08-14 Organic EL device KR100282334B1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100925807B1 (en) * 2001-08-24 2009-11-11 가부시키가이샤 한도오따이 에네루기 켄큐쇼 A luminous device

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100925807B1 (en) * 2001-08-24 2009-11-11 가부시키가이샤 한도오따이 에네루기 켄큐쇼 A luminous device
US7701130B2 (en) 2001-08-24 2010-04-20 Semiconductor Energy Laboratory Co., Ltd. Luminous device with conductive film
US7880378B2 (en) 2001-08-24 2011-02-01 Semiconductor Energy Laboratory Co., Ltd. Luminous device
US8456079B2 (en) 2001-08-24 2013-06-04 Semiconductor Energy Laboratory Co., Ltd. Luminous device

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