KR100290859B1 - Red light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted - Google Patents
Red light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted Download PDFInfo
- Publication number
- KR100290859B1 KR100290859B1 KR1019990008654A KR19990008654A KR100290859B1 KR 100290859 B1 KR100290859 B1 KR 100290859B1 KR 1019990008654 A KR1019990008654 A KR 1019990008654A KR 19990008654 A KR19990008654 A KR 19990008654A KR 100290859 B1 KR100290859 B1 KR 100290859B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- light emitting
- group
- hydrogen
- alkoxy
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 11
- 238000005401 electroluminescence Methods 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001336 alkenes Chemical class 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- -1 allyloxyl Chemical group 0.000 claims abstract description 3
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 239000002019 doping agent Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000001502 supplementing effect Effects 0.000 abstract 1
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000005283 ground state Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- XEPMXWGXLQIFJN-UHFFFAOYSA-K aluminum;2-carboxyquinolin-8-olate Chemical compound [Al+3].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 XEPMXWGXLQIFJN-UHFFFAOYSA-K 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- 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
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
Abstract
본 발명은 종래의 적색유기전계발광소자용 화합물의 특성 및 단점을 보완하여 발광효율을 높이고 장파장의 빛을 얻을 수 있는 하기 구조식의 적색유기전계발광소자용 화합물 및 이를 이용한 유기전계발광소자를 제공한다. 하기 구조식에서 R₁은 알킬기, 할로겐, 알켄 또는 알콕시기이다. 이때 알킬기, 알콕시기 또는 알켄은 1 내지 4 개의 탄소원자를 포함할 수 있으며, 상기 알킬기, 알콕시기 또는 알켄의 수소 대신 할로겐이 치환될 수 있다. R₂는 알콕시, 알릴옥실, 알킬, 페닐, 아민기, 할로겐 및 수소로 이루어진 군에서 선택된 어느 하나이다.The present invention provides a compound for a red organic light emitting device having the following structural formula and a organic light emitting device using the same structure to improve the luminous efficiency and obtain a long wavelength of light by supplementing the characteristics and disadvantages of the conventional compound for red organic light emitting device. . R 'in the following structural formula is an alkyl group, a halogen, an alkene or an alkoxy group. In this case, the alkyl group, alkoxy group or alkene may include 1 to 4 carbon atoms, and halogen may be substituted in place of hydrogen of the alkyl group, alkoxy group or alkene. R2 is any one selected from the group consisting of alkoxy, allyloxyl, alkyl, phenyl, amine group, halogen and hydrogen.
Description
본 발명은 디스플레이 소자에 관한 것으로, 특히 유기전계발광 디스플레이에 사용되는 적색 유기전계발광소자용 화합물 및 이를 이용한 유기전계발광소자에 관한 것이다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a display device, and in particular, to a compound for red organic light emitting device used in an organic light emitting display and an organic light emitting device using the same.
최근 디스플레이의 대형화에 따라 공간 점유가 적은 표시소자의 요구가 증가하고 있다. 이러한 표시소자 중 하나가 전계발광소자이다.Recently, as the size of a display increases, the demand for a display device having less space is increasing. One such display device is an electroluminescent device.
상기 전계발광소자는 사용 재료에 따라 무기전계발광소자와 유기전계발광소자로 나뉜다.The electroluminescent device is classified into an inorganic electroluminescent device and an organic electroluminescent device according to the material used.
상기 무기전계발광소자는 일반적으로 높은 전계를 인가함으로써 전자를 가속시켜 가속된 전자가 발광중심에 충돌하고 그 발광중심이 여기됨으로써 발광하는 소자이다.The inorganic electroluminescent device is generally a device that accelerates electrons by applying a high electric field so that the accelerated electrons collide with the light emitting center and the light emitting center is excited to emit light.
또한, 유기전계발광소자는 전자주입전극(cathode)과 정공주입전극(anode)으로부터 각각 전자와 정공을 발광부 내로 주입시켜 전자와 홀이 결합하여 생성된 엑시톤(exciton)이 여기상태(excited state)로부터 기저상태(ground state)로 떨어질 때 발광하는 소자이다.In addition, in the organic light emitting diode, excitons generated by combining electrons and holes by injecting electrons and holes from the electron injection electrode and the hole injection electrode into the light emitting unit, respectively, are in an excited state. The device emits light when it falls from the ground state to the ground state.
이와 같은 유기전계발광소자는 플라스틱 같은 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 넓은 시야각, 고속 응답성, 고 콘트라스트(contrast) 등의 뛰어난 특징을 갖고 있으므로 그래픽 디스플레이나 표면광원(surface light source)의 픽셀로서 사용될 수 있으며, 플라즈마 디스플레이 판넬(Plasma Display Panel)이나 무기전계발광소자에 비해 낮은 전압(10V 이하)에서 구동할 수 있고, 또한 전력 소모가 비교적 적으며, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 차세대 평면 디스플레이에 적합한 소자이다.Such organic electroluminescent devices can be formed on flexible flexible substrates such as plastics, and have excellent characteristics such as wide viewing angle, high speed response and high contrast, so that they can be used for graphic displays or surfaces. It can be used as a pixel of a surface light source, and can be driven at a lower voltage (10V or less) than a plasma display panel or an inorganic light emitting device, and consumes relatively little power, green, It can display three colors of blue and red, and is suitable for next-generation flat panel display.
유기전계발광소자의 구조 설명은 다음과 같다.The structure description of the organic light emitting display device is as follows.
유기전계발광소자는 투명기판 위에 제1전극(anode), 상기 제1전극 위에 형성되는 정공주입층, 수송층과, 상기 정공주입층, 수송층 위에 형성되는 발광층(light emitting layer)과, 상기 발광층 위에 형성되는 전자주입층, 수송층과, 상기 전자주입층, 수송층 위에 형성되는 제2전극(cathode)으로 이루어진다.The organic light emitting display device is formed on a first electrode (anode), a hole injection layer, a transport layer formed on the first electrode, a light emitting layer (light emitting layer) formed on the hole injection layer, a transport layer, and formed on the light emitting layer on a transparent substrate And an electron injection layer, a transport layer, and a second electrode formed on the electron injection layer and the transport layer.
유기전계발광소자 제작 과정을 간략히 살펴보면 다음과 같다.The manufacturing process of the organic light emitting diode will be briefly described as follows.
투명기판 위에 제1전극으로 입히는 물질로는 ITO(indium tin oxide)를 흔히 사용한다. 상기 제1전극 위에 정공주입층을 입히는 데 주로 카퍼 프탈로시아닌(copper phtalocyanine)을 10∼30nm 두께로 입힌다. 다음 4,4’-bis〔N-(1-naphthyl)-N-phenylamino〕-bipheyl(NPD)을 30∼60nm정도 증착하여 입혀서 정공수송층을 도입한다. 상기 정공수송층 위에 유기발광층을 형성하는 데 필요에 따라 도판트를 첨가한다. 녹색발광의 경우 유기발광층으로써 흔히 tris(8-hydroxy-quinolate)aluminum(Alq3)를 두께 30∼60nm정도 증착하며 도판트로는 MQD(N-Methylquinacridone)를 많이 쓴다. 상기 정공수송층 위에 전자수송층 및 전자주입층을 연속적으로 입히거나 전자주입수송층을 형성한다. 녹색발광의 경우 상기 (4)의 Alq3가 좋은 전자수송능력을 갖기 때문에 전자 주입/수송층을 쓰지 않는 경우도 있다. 다음 제2전극을 입히고, 마지막으로 보호막을 씌우게 된다.Indium tin oxide (ITO) is commonly used as a material to be coated on the transparent substrate as the first electrode. In order to coat the hole injection layer on the first electrode, copper phthalocyanine is mainly coated with a thickness of 10 to 30 nm. Next, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -bipheyl (NPD) is deposited by 30 to 60 nm and coated to introduce a hole transport layer. A dopant is added as necessary to form an organic light emitting layer on the hole transport layer. In the case of green light emission, tris (8-hydroxy-quinolate) aluminum (Alq 3 ) is commonly deposited as an organic light emitting layer with a thickness of 30 to 60 nm, and MQD (N-Methylquinacridone) is often used as a dopant. The electron transport layer and the electron injection layer are continuously coated or the electron injection transport layer is formed on the hole transport layer. In the case of green light emission, since Alq 3 of (4) has a good electron transport ability, an electron injection / transport layer may not be used. Next, a second electrode is coated and finally a protective film is covered.
여기서 청색은 청색 호스트(host)에 청색 도판트를 도핑하고 전자수송층으로 Alq3를 사용하여 구현하며 청색 호스트(host)의 특성에 따라 Alq3를 생략할 수 있다. 적색의 경우 상기 소자 제작 과정 중에 녹색 도판트 대신 적색 도판트를 도핑함으로써 적색파장을 얻을 수 있다.The blue may be implemented by doping a blue dopant to a blue host, using Alq 3 as an electron transport layer, and omitting Alq 3 according to the characteristics of the blue host. In the case of red, the red wavelength may be obtained by doping the red dopant instead of the green dopant during the device fabrication process.
그런데, 유기전계발광소자에서 사용하고 있는 적색물질은 녹색물질에 비하여 상대적으로 밝기 및 효율이 많이 떨어지며 장파장의 빛을 내기 위하여 도핑을 많이 할 경우 장파장의 빛을 얻을 수는 있으나 농도소광(concentration quenching)에 의하여 효율이 급격히 감소한다는 문제점이 있다.However, the red material used in the organic light emitting device is much lower in brightness and efficiency than the green material. When doping a lot of light for long wavelength light, long wavelength light can be obtained, but concentration quenching There is a problem that the efficiency is rapidly reduced by.
본 발명은 새로운 적색 유기전계발광소자용 화합물을 제공하여 발광층에 도입함으로써 소자의 안정성을 향상시키고 높은 발광효율 및 장파장의 빛을 얻을 수 있는 유기전계발광소자를 제공할 수 있다.The present invention can provide an organic electroluminescent device capable of improving the stability of the device and obtaining high luminous efficiency and long wavelength light by providing a new compound for a red organic electroluminescent device and introducing it into the light emitting layer.
본 발명은 하기의 구조식 1을 갖는 화합물을 제공한다.The present invention provides a compound having Structural Formula 1 below.
(구조식 1)(Formula 1)
상기 R1은 알킬기, 알콕시, 알켄 또는 할로겐으로써, 바람직하게는 1 내지 4 개의 탄소원자를 포함하거나, F 또는 Cl일 수 있다. 상기 n은 1부터 3까지의 정수이다. 상기 알킬기, 알콕시 또는 알켄의 탄소에는 수소 대신 할로겐이 치환될 수 있다.R 1 is an alkyl group, alkoxy, alkene or halogen, preferably containing 1 to 4 carbon atoms, or may be F or Cl. N is an integer of 1 to 3. Halogen may be substituted for hydrogen in the carbon of the alkyl group, alkoxy or alkene.
상기 R2는 알콕시, 알릴옥실, 알킬, 페닐, 아민기, 할로겐 및 수소로 이루어진 군에서 선택된 어느 하나이다.R 2 is any one selected from the group consisting of alkoxy, allyloxyl, alkyl, phenyl, amine group, halogen and hydrogen.
상기와 같은 본 발명의 화합물은 제1전극, 제2전극 및 다수의 유기막층을 포함하는 유기전계발광소자의 발광층에 함유된다. 이때, 본 발명의 화합물은 상기 발광층에 발광물질 자체 또는 도판트로써 사용될 수 있다.The compound of the present invention as described above is contained in the light emitting layer of the organic light emitting device including the first electrode, the second electrode and a plurality of organic film layers. In this case, the compound of the present invention may be used as the light emitting material itself or dopant in the light emitting layer.
본 발명에 따른 화합물은 전자 받개기로써 CN기를 도입하였으며, 전자 주개기로는 8-R₁-10-R₂-1,1,7,7-테트라메틸주로리딘(tetramethyljulolidine)을 도입하였다. 따라서 CN기를 포함하는 벤젠링인 상기 전자주개기와 주로리딘(julolidine) 유도체인 상기 전자받개기는 그 사이 탄소들의 이중결합을 통하여 콘주게이션(conjugation)된다. 상기 물질의 구조에서 1 및 7의 메틸기는 분자들간의 패킹(packing)을 막아서 농도소광(concentration quenching)을 막는 역할을 한다. 상기 8번 위치에는 전자주개기 역할을 보다 심화하는 치환기로써 알콕시기를 도입하였고 R₂에도 전자주개기를 도입하여 장파장을 얻도록 하였다.The compound according to the present invention introduced a CN group as an electron acceptor, and introduced 8-R ₁- 10-R2-1,1,7,7-tetramethyljulolidine as the electron acceptor. Therefore, the electron donor which is a benzene ring including a CN group and the electron acceptor which is a julidine derivative are conjugated through a double bond of carbons therebetween. The methyl groups of 1 and 7 in the structure of the material prevent the concentration quenching by blocking the packing between the molecules. In the 8th position, an alkoxy group was introduced as a substituent to deepen the role of the electron donor and an electron donor was introduced to R2 to obtain a long wavelength.
본 발명에 따른 화합물은 상기의 구조식으로부터 구조적으로 안정한 트랜스폼을 얻게 되므로 이를 통해 소자의 발광효율 유지를 도모할 수 있다.Since the compound according to the present invention obtains a structurally stable transform from the structural formula, it is possible to maintain the luminous efficiency of the device through this.
이때 본 발명의 화합물은 제1전극, 제2전극 및 다수의 유기막층을 포함하는 유기전계발광소자에서 발광층에 포함되어 구성될 수 있다. 상기 화합물은 발광층에서 적색발광물질 또는 도판트로써 사용된다.In this case, the compound of the present invention may be included in the light emitting layer in the organic light emitting device including a first electrode, a second electrode and a plurality of organic film layers. The compound is used as a red light emitting material or dopant in the light emitting layer.
상기 구조식 1을 갖는 화합물은 바람직하게는 다음과 같은 구조식 2, 3, 4, 5 및 6을 갖는 화합물에서 선택될 수 있다.The compound having the structural formula 1 may preferably be selected from compounds having the following structural formulas 2, 3, 4, 5 and 6.
(구조식 2)(Formula 2)
상기 구조식 2의 화합물은 구조식 1에서 n이 1, R₁이 메톡시기, 그리고 R2가 수소인 것을 특징으로 하는 화합물이다.The compound of formula 2 is a compound characterized in that n is 1, R 'is a methoxy group, and R 2 is hydrogen in the formula (1).
(구조식 3)(Structure 3)
상기 구조식 3의 화합물은 n이 1, R₁및 R₂가 각각 메톡시인 것을 특징으로 한다.The compound of formula 3 is characterized in that n is 1, R 'and R2 are each methoxy.
(구조식 4)(Formula 4)
상기 구조식 4의 화합물은 n이 1, R₁이 메톡시, 그리고 R₂가 메틸기인 것을 특징으로 한다.The compound of Formula 4 is characterized in that n is 1, R 'is methoxy, and R2 is a methyl group.
(구조식 5)(Structure 5)
상기 구조식 5의 화합물은 n이 1, R₁이 에톡시, 그리고 R₂는 수소인 것을 특징으로 한다.The compound of formula 5 is characterized in that n is 1, R 'is ethoxy, and R2 is hydrogen.
(구조식 6)(Formula 6)
상기 구조식 6의 화합물은 n이 1, R1이 F, 그리고 R2는 수소인 것을 특징으로 한다.The compound of formula 6 is characterized in that n is 1, R 1 is F, and R 2 is hydrogen.
또한, 본 발명의 상기 화합물들이 적용될 수 있는 유기전계발광소자는 당업자라면 종래기술을 이용하여 그 소자의 형태를 변경하여 사용할 수 있을 것이다.In addition, the organic electroluminescent device to which the compounds of the present invention can be applied may be used by those skilled in the art by changing the shape of the device using conventional techniques.
본 발명에 따른 화합물의 제법에 대한 일 실시예로서, 구조식 2의 화합물의 제법을 다음과 같은 일련의 반응식으로 나타낼 수 있다.As an embodiment of the preparation of the compound according to the present invention, the preparation of the compound of formula 2 can be represented by the following series of schemes.
본 발명의 적색 유기전계발광소자 화합물은 유기전계발광소자에 적용되어 발광물질의 수명을 증가시키고 발광효율을 높이며 농도소광을 감소시키는 효과가 있다.The red organic light emitting diode compound of the present invention is applied to the organic light emitting diode has an effect of increasing the lifetime of the light emitting material, increasing the luminous efficiency and reducing the concentration quenching.
Claims (10)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019990008654A KR100290859B1 (en) | 1999-03-15 | 1999-03-15 | Red light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019990008654A KR100290859B1 (en) | 1999-03-15 | 1999-03-15 | Red light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20000060399A KR20000060399A (en) | 2000-10-16 |
| KR100290859B1 true KR100290859B1 (en) | 2001-05-15 |
Family
ID=19576611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019990008654A KR100290859B1 (en) | 1999-03-15 | 1999-03-15 | Red light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR100290859B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100459134B1 (en) * | 2002-01-26 | 2004-12-03 | 엘지전자 주식회사 | Compound For Yellow Light Emitting Material And Organic Electroluminescent Device Comprising It |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100376320B1 (en) * | 2000-10-18 | 2003-03-15 | 삼성에스디아이 주식회사 | A red dopant for organic electroluminscene device and the organic electroluminscene device using the same |
| US6844089B2 (en) * | 2002-05-10 | 2005-01-18 | Sensient Imaging Technologies Gmbh | Organic red electro-luminescent device and dopant |
-
1999
- 1999-03-15 KR KR1019990008654A patent/KR100290859B1/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100459134B1 (en) * | 2002-01-26 | 2004-12-03 | 엘지전자 주식회사 | Compound For Yellow Light Emitting Material And Organic Electroluminescent Device Comprising It |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20000060399A (en) | 2000-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6565996B2 (en) | Organic light-emitting device having a color-neutral dopant in a hole-transport layer and/or in an electron-transport layer | |
| US6727644B2 (en) | Organic light-emitting device having a color-neutral dopant in an emission layer and in a hole and/or electron transport sublayer | |
| KR100377575B1 (en) | A blue luiminiscence compound for organic electroluminscene device and the organic electroluminscene device using the same | |
| US6692846B2 (en) | Organic electroluminescent device having a stabilizing dopant in a hole-transport layer or in an electron-transport layer distant from the emission layer | |
| KR20030015870A (en) | White organic light-emitting devices with improved efficiency | |
| JP2002038140A (en) | Organic luminescent layer and electroluminescent device | |
| KR20120103636A (en) | Oled with high efficiency blue light-emitting layer | |
| KR100469240B1 (en) | Organic electroluminescent device | |
| KR20010049923A (en) | Organic electroluminescent device | |
| JP2010251585A (en) | Organic electroluminescent element | |
| KR100290859B1 (en) | Red light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted | |
| KR100377573B1 (en) | A red luiminiscence compound for organic electroluminscene device and the organic electroluminscene device using the same | |
| KR100546590B1 (en) | Organic Elechrolu mine scence Device for Green color | |
| KR20060117038A (en) | Light emitting compound and oled | |
| KR20040094078A (en) | Organic elcetroluminescence display emitting white color | |
| US6727362B1 (en) | Coumarin derivatives and an electroluminescent (EL) device using the coumarin derivatives | |
| KR100747310B1 (en) | Organic Electro-Luminescence Device | |
| KR100282334B1 (en) | Organic EL device | |
| KR20010015513A (en) | organic electroluminescence device | |
| KR100269392B1 (en) | Organic electroluminescence devices using quinacridone complex as fluorescent emitting material | |
| KR100313886B1 (en) | Organic Electro-luminescence Display Device | |
| Kanno et al. | Developments in OLEDs with a co-dopant system for improved efficiency and stability | |
| KR100281063B1 (en) | Organic EL device | |
| KR20020032657A (en) | Chemical Compound For Red Color Organic Electro-Luminescence Element And An Organic Electro-Luminescence Element Including It | |
| KR20000051315A (en) | Electroluminescent device emitting a red light |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20121228 Year of fee payment: 13 |
|
| FPAY | Annual fee payment |
Payment date: 20131227 Year of fee payment: 14 |
|
| FPAY | Annual fee payment |
Payment date: 20150227 Year of fee payment: 15 |
|
| FPAY | Annual fee payment |
Payment date: 20160226 Year of fee payment: 16 |
|
| FPAY | Annual fee payment |
Payment date: 20180213 Year of fee payment: 18 |
|
| EXPY | Expiration of term |