公开(公告)号：KR100295098B1

公开(公告)日：2001-07-12

申请号：KR1019980043226

申请日：1998-10-15

Applicant: 한국전자통신연구원

Inventor： 황도훈 ,  정태형 ,  송승용 ,  심홍구

IPC: C07D271/10

Abstract: 본 발명은 발광 고분자에서 전자의 주입과 수송 능력을 우수하게 하는 구조식 (M-1) 및 (M-2)의 옥사디아졸 유도체를 얻고, 이를 정공 수송 능력이 우수한 화합물과 반응시켜 유기용매에 용해 가능하며, 전자와 정공 수송 능력이 우수한 일반식(P-1 ∼ P-2)의 발광 고분자를 합성하고, 이를 이용한 전기 발광 소자에 관한 것으로, 한 고분자 사슬 내에 전자와 정공 수송 능력이 우수한 반복 단위가 함께 있도록 하여 전자와 정공의 주입을 용이하게 하고 여기자의 생성 확률을 높여 전기 발광 소자의 발광 효율을 크게 향상시켰다.

公开(公告)号：KR100399046B1

公开(公告)日：2003-09-26

申请号：KR1020000087121

申请日：2000-12-30

Applicant: 한국전자통신연구원 ,  한국과학기술원

Inventor： 도이미 ,  이정익 ,  추혜용 ,  김성현 ,  정태형 ,  이효영 ,  심홍구 ,  정병준 ,  윤종복

IPC: C09K11/06

CPC classification number: C09K11/06 ,  H01L51/0037 ,  H01L51/0042 ,  H01L51/0051 ,  H01L51/0065 ,  H01L51/0067 ,  H01L51/0068 ,  H01L51/0071 ,  H01L51/0072 ,  H01L51/0081 ,  H01L51/5012 ,  H01L2251/308 ,  Y10S428/917

Abstract: In the organic electroluminescence (EL) device containing a bis-condensed derivative of 4-(dicyanomethylene)-2-methyl-6-(para-(dimethylaminostyryl)-4H-pyran, and the preparation thereof, the inventive organic electroluminescence device has a high luminescent efficiency and color coordinates based on a high purity, and is further simple in a synthesis and is prominent in a thermal stability, thereby providing great merits to a mass production of the organic electroluminescence device.

Abstract translation: 在含有4-（二氰基亚甲基）-2-甲基-6-（对 - （二甲基氨基苯乙烯基）-4H-吡喃的双缩合衍生物的有机电致发光（EL）器件及其制备中，本发明的有机电致发光器件具有 基于高纯度的高发光效率和色坐标，并且合成更简单并且热稳定性突出，由此为大量生产有机电致发光装置提供了很大的优点。

公开(公告)号：KR1020010076772A

公开(公告)日：2001-08-16

申请号：KR1020000004127

申请日：2000-01-28

Applicant: 한국전자통신연구원

Inventor： 황도훈 ,  정태형 ,  안택 ,  심홍구

IPC: C08F12/00

CPC classification number: C09K11/06 ,  C08G61/02 ,  H01L51/0035 ,  H01L51/0043 ,  H01L51/50

Abstract: PURPOSE: A method for preparing luminescent polymer for the application to manufacture of light emitting diode(LED) is provided, in which one monomer having fluorine-substituted phenyl groups is reacted with dialdehyde monomer such as carbazole, phenyl, fluorene and thiophene. The luminescent polymer that is prepared by this method has superior electroluminescent efficiency to conventional luminescent polymers using p-conjugated polymers since its combination between electron and hole is well balanced. CONSTITUTION: The monomer having fluorine-substituted phenyl groups is selected from 2,3,5,6-tetrafluoro-1,4-xylene bis(triphenyl phosphonium bromide) benzene (formula 1) or 2,3,5,6-tetrafluoro-1,4-xylene bis(diethoxy phosphonate) benzene (formula 2). Such monomers react with dialdehyde monomer such as carbazole, phenyl, fluorene and thiophene, wherein two phosphonium salt or phosphonate are bonded with two aldehyde groups so that these are conjugated (π-conjugation).

Abstract translation: 目的：提供一种用于制造发光二极管（LED）的发光聚合物的制备方法，其中具有氟取代的苯基的单体与二醛单体如咔唑，苯基，芴和噻吩反应。 通过该方法制备的发光聚合物对于使用对共轭聚合物的常规发光聚合物具有优异的电致发光效率，因为其电子和空穴之间的组合是均衡的。 构成：具有氟取代苯基的单体选自2,3,5,6-四氟-1,4-二甲苯双（三苯基溴化鏻）苯（式1）或2,3,5,6-四氟 - 1,4-二甲苯双（二乙氧基膦酸酯）苯（式2）。 这些单体与二醛单体如咔唑，苯基，芴和噻吩反应，其中两个鏻盐或膦酸酯与两个醛基键合，使得它们共轭（π共轭）。

公开(公告)号：KR100289059B1

公开(公告)日：2001-05-02

申请号：KR1019980053778

申请日：1998-12-08

Applicant: 한국전자통신연구원

Inventor： 황도훈 ,  정태형 ,  안택 ,  심홍구 ,  도이미 ,  추혜용

IPC: C08G61/12

Abstract: 본 발명은, 발광 고분자, 그의 제조방법 및 이를 이용한 전기발광소자에 관한 것으로, 본 발명에 따른 발광 고분자는, 하기 화학식 1 또는 화학식 2로 표시되는 것과 같이, 나프탈렌비닐렌과 카바졸비닐렌 단위가 규칙적으로 반복되는 구조를 갖는다. 또한, 본 발명에 따른 발광 고분자의 제조방법은, 나프탈렌의 포스포늄염 또는 포스폰산염을 카바졸 디알데히드와 비티히 반응 또는 비티히-에몬스 반응시키는 단계를 포함하며, 본 발명에 따른 전기발광소자는, 이와 같은 발광 고분자를 발광층 및 정공 수송층 중 적어도 1개 층 이상에 사용한 것을 특징으로 한다.
[화학식 1]

[화학식 2]

公开(公告)号：KR1020000038697A

公开(公告)日：2000-07-05

申请号：KR1019980053778

申请日：1998-12-08

Applicant: 한국전자통신연구원

Inventor： 황도훈 ,  정태형 ,  안택 ,  심홍구 ,  도이미 ,  추혜용

IPC: C08G61/12

Abstract: PURPOSE: A soluble luminescent polymer in organic solvent, having a good luminous and hole transfer characteristics and workability is provided which stably operates in high voltage. CONSTITUTION: A luminous polymer(formula 1; R is C1-C20 linear or branched alkyl group) having regular repeating unit of naphthalene vinylene and carbazole vinylene is prepared by the Wittig reaction or Wittig-Emons reaction of naphthalene phosphonium salt(formula 3; X is halogen; R is C1-C20 linear or branched alkyl group) or naphthalene phosphonate, and carbazole dialdehyde(formula 5; R is C1-C20 linear or branched alkyl group).

Abstract translation: 目的：提供在有机溶剂中的可溶性发光聚合物，其具有良好的发光和空穴转移特性和可加工性，其稳定地在高电压下操作。 构成：通过萘鏻盐的Wittig反应或Wittig-Emons反应制备具有萘亚乙烯基和咔唑亚乙烯基的规则重复单元的发光聚合物（式1; R是C 1 -C 20直链或支链烷基）（式3; X R为C1-C20直链或支链烷基）或萘膦酸酯，咔唑二醛（式5; R为C1-C20直链或支链烷基）。

公开(公告)号：KR100404325B1

公开(公告)日：2003-11-03

申请号：KR1020000004127

申请日：2000-01-28

Applicant: 한국전자통신연구원

Inventor： 황도훈 ,  정태형 ,  안택 ,  심홍구

IPC: C08F12/00

Abstract: PURPOSE: A method for preparing luminescent polymer for the application to manufacture of light emitting diode(LED) is provided, in which one monomer having fluorine-substituted phenyl groups is reacted with dialdehyde monomer such as carbazole, phenyl, fluorene and thiophene. The luminescent polymer that is prepared by this method has superior electroluminescent efficiency to conventional luminescent polymers using p-conjugated polymers since its combination between electron and hole is well balanced. CONSTITUTION: The monomer having fluorine-substituted phenyl groups is selected from 2,3,5,6-tetrafluoro-1,4-xylene bis(triphenyl phosphonium bromide) benzene (formula 1) or 2,3,5,6-tetrafluoro-1,4-xylene bis(diethoxy phosphonate) benzene (formula 2). Such monomers react with dialdehyde monomer such as carbazole, phenyl, fluorene and thiophene, wherein two phosphonium salt or phosphonate are bonded with two aldehyde groups so that these are conjugated (π-conjugation).

Abstract translation: 目的：提供一种制备用于制造发光二极管（LED）的发光聚合物的方法，其中具有氟取代的苯基的一种单体与诸如咔唑，苯基，芴和噻吩的二醛单体反应。 由该方法制备的发光聚合物由于其电子与空穴的组合良好平衡，因此与使用p-共轭聚合物的常规发光聚合物相比具有优异的电致发光效率。 构成：具有氟取代苯基的单体选自2,3,5,6-四氟-1,4-二甲苯双（三苯基溴化鏻）苯（式1）或2,3,5,6-四氟-1 1,4-二甲苯双（二乙氧基膦酸酯）苯（式2）。 这种单体与二醛单体如咔唑，苯基，芴和噻吩反应，其中两个鏻盐或膦酸酯与两个醛基键合，从而使它们共轭（π-共轭）。

公开(公告)号：KR1020030042284A

公开(公告)日：2003-05-28

申请号：KR1020010073004

申请日：2001-11-22

Applicant: 한국전자통신연구원 ,  한국과학기술원

Inventor： 정병준 ,  심홍구 ,  이정익 ,  추혜용 ,  도이미 ,  정태형

IPC: C09K11/06

CPC classification number: H01L51/0051 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1014 ,  C09K2211/1029 ,  C09K2211/1088 ,  H01L51/0042 ,  H01L51/0081 ,  H01L51/5012 ,  H01L2251/308

Abstract: PURPOSE: Provided are a red organic electroluminescent compound having red light emitting property and excellent luminous efficiency, a method for producing the same, and an electroluminescent device comprising the same. CONSTITUTION: The red organic electroluminescent compound has a structure represented by formula 1(wherein each of R1, R1', R2 and R2' is hydrogen, or alkyl group, aryl group, or hetero ring having C1-C30, each of R3, R3', R4, and R4' is hydrogen, alkyl group or alkoxy group having C1-C10, any one least pair of R1 and R3, R1' and R3', R2 and R4, and R2' and R4' can form -R1-R3-, -R1'-R3', -R2-R4-, and -R2'-R4'-, each of R5, R5', R6 and R6' is hydrogen, or alkyl group, alkoxy group or aryl group having C1-C30, and at least one of R3, R3', R4, R4', R5, R5', R6 and R6' is not hydrogen).

Abstract translation: 目的：提供具有红色发光性和发光效率优异的红色有机电致发光化合物，其制造方法和包含该有机电致发光化合物的电致发光器件。 构成：红色有机电致发光化合物具有式1所示的结构（其中R 1，R 1'，R 2和R 2'各自为氢或烷基，芳基或具有C 1 -C 30的杂环，各自为R 3，R 3 '，R 4和R 4'是氢，具有C 1 -C 10的烷基或烷氧基，R 1和R 3，R 1'和R 3'，R 2和R 4中的至少一个对，R 2和R 4'可以形成-R1- R3-，-R1'-R3'，-R2-R4-和-R2'-R4'-，R5，R5'，R6和R6'各自为氢或烷基，烷氧基或具有C1 -C30，R3，R3'，R4，R4'，R5，R5'，R6和R6'中的至少一个不是氢）。

公开(公告)号：KR1020030021674A

公开(公告)日：2003-03-15

申请号：KR1020010055046

申请日：2001-09-07

Applicant: 한국전자통신연구원 ,  한국과학기술원

Inventor： 이정익 ,  추혜용 ,  이효영 ,  오지영 ,  김성현 ,  도이미 ,  정태형 ,  이재민 ,  정병준 ,  심홍구

IPC: C09K11/06

CPC classification number: B82Y30/00 ,  B82Y10/00 ,  Y10S428/917

Abstract: PURPOSE: Provided are a compound having hole transfer/injection ability, which is excellent in adhesive ability, heat-stability, and time-stability, and an organic electroluminescent element having a self-assembled layer containing the compound, which is excellent in electrical properties and optical properties. CONSTITUTION: The compound having the hole transfer/injection ability is represented by the formula: Ar-R-SiX3 and the organic electroluminescent element contains a cathode, a hole transfer/injection layer, an organic luminescent layer, an electron transfer/injection layer, an anode, and the self-assembled layer placed between the cathode and the hole transfer/injection layer and comprising the compound represented by the formula: Ar-R-SiX3. In the formula, Ar is a functional group having the hole transfer/injection ability, wherein R1-R3 are identically or differently hydrogen atom, two aryl groups, or amine group having substituted aryl, or C1-C22 alkyl or alkoxy group, R is C1-C22 alkyl group, and X is alkoxy or halogen.

Abstract translation: 目的：提供具有优异的粘合性，热稳定性和时间稳定性的具有空穴转移/注射能力的化合物，以及具有含有该化合物的自组装层的有机电致发光元件，其电性能优异 和光学性质。 构成：具有空穴转移/注入能力的化合物由下式表示：Ar-R-SiX 3，有机电致发光元件含有阴极，空穴转移/注入层，有机发光层，电子转移/注入层， 阳极，以及置于阴极和空穴传输/注入层之间的自组装层，并且包含由下式表示的化合物：Ar-R-SiX 3。 在该式中，Ar是具有空穴转移/注入能力的官能团，其中R1-R3相同或不同，氢原子，两个芳基或具有取代芳基的胺基或C1-C22烷基或烷氧基，R是 C1-C22烷基，X是烷氧基或卤素。

公开(公告)号：KR1020020058978A

公开(公告)日：2002-07-12

申请号：KR1020000087121

申请日：2000-12-30

Applicant: 한국전자통신연구원 ,  한국과학기술원

Inventor： 도이미 ,  이정익 ,  추혜용 ,  김성현 ,  정태형 ,  이효영 ,  심홍구 ,  정병준 ,  윤종복

IPC: C09K11/06

CPC classification number: C09K11/06 ,  H01L51/0037 ,  H01L51/0042 ,  H01L51/0051 ,  H01L51/0065 ,  H01L51/0067 ,  H01L51/0068 ,  H01L51/0071 ,  H01L51/0072 ,  H01L51/0081 ,  H01L51/5012 ,  H01L2251/308 ,  Y10S428/917

Abstract: PURPOSE: Provided is an organic electroluminescent element using 4-(dicyanomethylene)-2-methyl-6-(p-(dimethylamino)styryl)-4H-pyran as a red light emitting material, which is excellent in thermal stability, synthesized simply, and shows high pure red. CONSTITUTION: The organic electroluminescent element contains a cathode, an organic layer containing a compound represented by the formula, and an anode, wherein X is O, S, CH2 or NR, R is low alkyl, R1 and R2 are tertiary amines containing rings or fused rings having 2-(dialkylamino)thienyl rings. And the organic electroluminescent element is produced by a process comprising the steps of: forming the cathode on a substrate, wherein the cathode is indium tin oxide; forming the organic layer containing the compound represented by the formula 6 on the cathode; forming the anode on the organic layer, wherein the anode is Al.

Abstract translation: 目的：提供使用4-（二氰基亚甲基）-2-甲基-6-（对 - （二甲基氨基）苯乙烯基）-4H-吡喃作为红色发光材料的有机电致发光元件，其热稳定性优异，简单合成， 并显示高纯红色。 构成：有机电致发光元件含有阴极，含有下式表示的化合物的有机层和阳极，其中X为O，S，CH 2或NR，R为低级烷基，R 1和R 2为含叔胺的环或 稠环具有2-（二烷基氨基）噻吩环。 并且有机电致发光元件通过包括以下步骤的方法制造：在衬底上形成阴极，其中阴极是氧化铟锡; 在阴极上形成含有式6表示的化合物的有机层; 在有机层上形成阳极，其中阳极是Al。

公开(公告)号：KR100467313B1

公开(公告)日：2005-01-24

申请号：KR1020010073004

申请日：2001-11-22

Applicant: 한국전자통신연구원 ,  한국과학기술원

Inventor： 정병준 ,  심홍구 ,  이정익 ,  추혜용 ,  도이미 ,  정태형

IPC: C09K11/06

CPC classification number: H01L51/0051 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1014 ,  C09K2211/1029 ,  C09K2211/1088 ,  H01L51/0042 ,  H01L51/0081 ,  H01L51/5012 ,  H01L2251/308

Abstract: Red organic electroluminescent compounds containing bis-condensed DCM derivatives, a method for synthesizing the same and an organic electroluminescent device using the same. The red organic electroluminescent compound having the formula: wherein R1, R1', R2 and R2' are independently hydrogen atom, or C1-C30 alkyl, aryl or hetero ring; R3, R3', R4 and R4' are independently hydrogen atom, C1-C10 alkyl or alkoxy; one or more pairs selected from the group consisting of R1 and R3, R1' and R3', R2 and R4, and R2' and R4' can be connected in forms of -R1-R3-, -R1'-R3'-, -R2-R4-, and -R2'-R4'-; R5, R5', R6 and R6' are independently hydrogen atom, or C1-C30 alkyl, alkoxy or aryl; at least one of R3, R3', R4, R4', R5, R5', R6 and R6' is not hydrogen atom.

Abstract translation: 含有双缩合DCM衍生物的红色有机电致发光化合物，其合成方法和使用其的有机电致发光器件。 具有下式的红色有机电致发光化合物：其中R1，R1'，R2和R2'独立地为氢原子或C1-C30烷基，芳基或杂环; R3，R3'，R4和R4'独立地为氢原子，C1-C10烷基或烷氧基; 选自R1和R3中的一对或多对，R1'和R3'，R2和R4以及R2'和R4'可以以-R1-R3-，-R1'-R3'-， -R2-R4-和-R2'-R4'-; R5，R5'，R6和R6'独立地为氢原子或C1-C30烷基，烷氧基或芳基; R3，R3'，R4，R4'，R5，R5'，R6和R6'中的至少一个不是氢原子。