KR100495740B1 - 조성물, 막의 제조방법, 및 기능 소자와 이의 제조방법 - Google Patents
조성물, 막의 제조방법, 및 기능 소자와 이의 제조방법 Download PDFInfo
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- KR100495740B1 KR100495740B1 KR10-2000-7013448A KR20007013448A KR100495740B1 KR 100495740 B1 KR100495740 B1 KR 100495740B1 KR 20007013448 A KR20007013448 A KR 20007013448A KR 100495740 B1 KR100495740 B1 KR 100495740B1
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- South Korea
- Prior art keywords
- composition
- solvent
- functional
- light emitting
- benzene derivative
- Prior art date
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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
- 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
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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Abstract
Description
발광 재료 | 용매 | |
R(적) 잉크 | 화학식 1의 화합물 0.70g화학식 2의 화합물 0.2g화학식 6의 화합물 0.1g | 도데실벤젠 100ml테트랄린 100ml |
G(녹) 잉크 | 화학식 1의 화합물 0.76g화학식 2의 화합물 0.2g화학식 4의 화합물 0.04g | 도데실벤젠 100ml테트랄린 100ml |
B(청) 잉크 | 화학식 1의 화합물 0.78g화학식 2의 화합물 0.15g화학식 3의 화합물 0.07g | 도데실벤젠 100ml테트랄린 100ml |
발광 재료 | 용매 | |
R(적) 잉크 | 화학식 1의 화합물 0.70g화학식 2의 화합물 0.2g화학식 5의 화합물 0.1g | 도데실벤젠 100ml테트랄린 100ml |
G(녹) 잉크 | 화학식 1의 화합물 0.76g화학식 2의 화합물 0.2g화학식 4의 화합물 0.04g | 도데실벤젠 100ml테트랄린 100ml |
B(청) 잉크 | 화학식 1의 화합물 0.78g화학식 2의 화합물 0.15g화학식 3의 화합물 0.07g | 도데실벤젠 100ml테트랄린 100ml |
발광 재료 | 용매 | |
R(적) 잉크 | 화학식 7의 화합물 0.98g화학식 8의 화합물 0.02g | 크실렌 200ml |
고분자 화합물(1중량%/v) | 용매 | |||
R(적) | 화학식 1의 화합물0.7g | 화학식 2의 화합물0.2g | 화학식 5의 화합물0.1g | 크실렌100ml |
G(녹) | 화학식 1의 화합물0.76g | 화학식 2의 화합물0.20g | 화학식 4의 화합물0.04g | 크실렌100ml |
B(청) | 화학식 1의 화합물0.78g | 화학식 2의 화합물0.15g | 화학식 3의 화합물0.07g | 크실렌100ml |
고분자 화합물(1중량%/v) | 용매 | |||
R(적) | 화학식 1의 화합물0.7g | 화학식 2의 화합물0.2g | 화학식 5의 화합물0.1g | 메시틸렌100ml |
G(녹) | 화학식 1의 화합물0.76g | 화학식 2의 화합물0.20g | 화학식 4의 화합물0.04g | 메시틸렌100ml |
B(청) | 화학식 1의 화합물0.78g | 화학식 2의 화합물0.15g | 화학식 3의 화합물0.07g | 메시틸렌100ml |
고분자 화합물(1중량%/v) | 용매 | |||
R(적) | 화학식 1의 화합물0.7g | 화학식 2의 화합물0.2g | 화학식 5의 화합물0.1g | 1,2,3,4-테트라메틸벤젠100ml |
G(녹) | 화학식 1의 화합물0.76g | 화학식 2의 화합물0.20g | 화학식 4의 화합물0.04g | 1,2,3,4-테트라메틸벤젠100ml |
B(청) | 화학식 1의 화합물0.78g | 화학식 2의 화합물0.15g | 화학식 3의 화합물0.07g | 1,2,3,4-테트라메틸벤젠100ml |
고분자 화합물(1중량%/v) | 용매 | ||||
R(적) | 화학식 1의 화합물0.7g | 화학식 2의 화합물0.2g | 화학식 5의 화합물0.1g | 디에틸벤젠30ml | 1,2,3,4-테트라메틸벤젠70ml |
G(녹) | 화학식 1의 화합물0.76g | 화학식 2의 화합물0.20g | 화학식 4의 화합물0.04g | 디에틸벤젠30ml | 1,2,3,4-테트라메틸벤젠70ml |
B(청) | 화학식 1의 화합물0.78g | 화학식 2의 화합물0.15g | 화학식 3의 화합물0.07g | 디에틸벤젠30ml | 1,2,3,4-테트라메틸벤젠70ml |
고분자 화합물(1중량%/v) | 용매 | ||||
R(적) | 화학식 1의 화합물0.7g | 화학식 2의 화합물0.2g | 화학식 5의 화합물0.1g | 메시틸렌80ml | 사이클로헥실벤젠20ml |
G(녹) | 화학식 1의 화합물0.76g | 화학식 2의 화합물0.20g | 화학식 4의 화합물0.04g | 메시틸렌80ml | 사이클로헥실벤젠20ml |
B(청) | 화학식 1의 화합물0.78g | 화학식 2의 화합물0.15g | 화학식 3의 화합물0.07g | 메시틸렌80ml | 사이클로헥실벤젠20ml |
고분자 화합물(1중량%/v) | 용매 | ||||
R(적) | 화학식 1의 화합물0.7g | 화학식 2의 화합물0.2g | 화학식 5의 화합물0.1g | 도데실벤젠30ml | 1,2,3,4-테트라메틸벤젠70ml |
G(녹) | 화학식 1의 화합물0.76g | 화학식 2의 화합물0.20g | 화학식 4의 화합물0.04g | 도데실벤젠30ml | 1,2,3,4-테트라메틸벤젠70ml |
B(청) | 화학식 1의 화합물0.78g | 화학식 2의 화합물0.15g | 화학식 3의 화합물0.07g | 도데실벤젠30ml | 1,2,3,4-테트라메틸벤젠70ml |
조성물 | 용액 안정성 | 토출성 | 상 분리 | |
비교품 | 1[R.G.B) | ○ | × | - |
본 발명품 | 2(R.G.B) | ○ | ○ | ○ |
3(R.G.B) | ○ | ◎ | ○ | |
4(R.G.B) | ○ | ◎ | ○ | |
5(R.G.B) | ○ | ◎ | ○ | |
6(R.G.B) | ○ | ◎ | × |
재료 | 함유량(중량%) |
폴리에틸렌디옥시티오펜/폴리스티렌 설폰산 혼합액 | 11.08 |
폴리스티렌 설폰산 | 1.44 |
이소프로필알콜 | 10 |
N-메틸피롤리돈 | 27.48 |
1,3-디메틸-2-이미다졸리디논 | 50 |
Claims (35)
- 하나 이상의 치환기를 갖고 당해 치환기의 총 탄소수가 3 이상인 벤젠 유도체를 적어도 1종 포함하는 용매와 유기 전기 발광(electroluminescence; EL) 재료, 실리카 유리의 전구체, 컬러 필터용 재료, 도전성 재료 및 반도체 재료로 이루어진 그룹으로부터 선택된 기능 재료로 이루어지며, 상기 벤젠 유도체의 비점이 200℃ 이상인 것을 특징으로 하는 조성물.
- 삭제
- 제1항에 있어서, 벤젠 유도체가 도데실벤젠인 조성물.
- 제1항 또는 제3항에 있어서, 벤젠 유도체를 적어도 1종 포함하는 용매가 비점이 140℃ 이상인 다른 용매를 함유하는 조성물.
- 제4항에 있어서, 벤젠 유도체가 도데실벤젠이고, 비점이 140℃ 이상인 다른 용매가 시멘, 테트랄린, 쿠멘, 데칼린, 듀렌, 사이클로헥실벤젠, 디헥실벤젠, 테트라메틸벤젠 및 디부틸벤젠으로 이루어진 그룹으로부터 선택된 적어도 1종인 조성물.
- 제1항 또는 제3항에 있어서, 벤젠 유도체를 적어도 1종 포함하는 용매가 비점이 180℃ 이상인 다른 용매를 함유하는 조성물.
- 제1항에 있어서, 벤젠 유도체의 증기압(실온)이 0.10 내지 10mmHg인 조성물.
- 제7항에 있어서, 벤젠 유도체가 1,2,3,4-테트라메틸벤젠인 조성물.
- 제7항에 있어서, 벤젠 유도체가 증기압 0.10 내지 0.50mmHg의 벤젠 유도체 적어도 1종과 증기압 0.50 내지 10mmHg의 벤젠 유도체 적어도 1종과의 혼합물인 조성물.
- 제9항에 있어서, 증기압 0.10 내지 0.50mmHg의 벤젠 유도체가 테트라메틸벤젠인 조성물.
- 제9항에 있어서, 증기압 0.10 내지 0.50mmHg의 벤젠 유도체가 사이클로헥실벤젠인 조성물.
- 제9항 내지 제11항 중의 어느 한 항에 있어서, 증기압 0.50 내지 10mmHg의 벤젠 유도체가 디에틸벤젠 및/또는 메시틸렌인 조성물.
- 제1항 또는 제3항에 있어서, 기능 재료가 유기 EL 재료인 조성물.
- 제13항에 있어서, 유기 EL 재료가 플루오렌계 고분자 유도체의 적어도 1종인 조성물.
- 제14항에 있어서, 플루오렌계 고분자 유도체가 다음 화학식 1 내지 5의 화합물인 조성물.화학식 1화학식 2화학식 3화학식 4화학식 5
- 제1항 또는 제3항에 있어서, 기능 재료가 실리카 유리의 전구체인 조성물.
- 제1항 또는 제3항에 있어서, 기능 재료가 컬러 필터용 재료인 조성물.
- 제1항 또는 제3항에 있어서, 잉크젯법에 사용되는 조성물.
- 제1항 또는 제3항에 따르는 조성물을 기재 위에 공급하여 분산시킨 후, 당해 기재를 열처리함을 특징으로 하는, 막의 제조방법.
- 제19항에 있어서, 조성물을 토출 장치로부터 기판 위에 토출시켜 분산시킨 후, 기판을 토출시의 온도보다 고온으로 처리하는, 막의 제조방법.
- 제20항에 있어서, 고온 처리시 가압시키면서 가열하는, 막의 제조방법.
- 제20항 또는 제21항에 있어서, 고온 처리 직후 그대로 감압시켜 용매를 제거하는, 막의 제조방법.
- 제20항 또는 제21항에 있어서, 토출 장치가 잉크젯 프린팅 장치인 막의 제조방법.
- 제1항 또는 제3항에 따르는 조성물을 사용하여 형성됨을 특징으로 하는 기능 소자.
- 제24항에 있어서, 표시 소자인 기능 소자.
- 제25항에 있어서, 표시 소자가 제1 전극과 제2 전극 사이에 발광 재료층을 구비하고, 당해 발광 재료층이 제1항 내지 제3항 중의 어느 한 항에 따르는 조성물을 사용하여 형성되어 이루어지는 기능 소자.
- 제26항에 있어서, 제1 전극과 발광 재료층 사이에 정공 주입/수송층을 설치하여 이루어지는 기능 소자.
- 제25항에 있어서, 표시 소자가 유기 EL 소자인 기능 소자.
- 제26항에 따르는 기능 소자의 제조방법으로서, 조성물을 제1 전극을 갖는 기재 위에 선택적으로 공급하여 발광 재료층 패턴을 형성시키고, 계속해서 제2 전극을 당해 발광 재료층 패턴 위에 형성시킴을 특징으로 하는, 기능 소자의 제조방법.
- 제29항에 있어서, 조성물을 선택적으로 공급하고 열처리하여 발광 재료층 패턴을 형성시키는, 기능 소자의 제조방법.
- 제30항에 있어서, 열 처리를 40 내지 200℃의 온도 범위에서 실시하는, 기능 소자의 제조방법.
- 제30항 또는 제31항에 있어서, 열 처리를 가압하에 실시하는, 기능 소자의 제조방법.
- 제30항 또는 제31항에 있어서, 열 처리에 있어서 조성물이 완전히 건조되기 전에 감압시키는, 기능 소자의 제조방법.
- 제29항 내지 제31항 중의 어느 한 항에 있어서, 극성 용매를 포함하는 용액을 사용하여 잉크젯법으로 정공 주입/수송층을 제1 전극을 갖는 기재 위에 형성시킨 후, 발광 재료층 패턴을 정공 주입/수송층 위에 형성시켜 유기 EL 소자를 수득하는, 기능 소자의 제조방법.
- 제29항 내지 제31항 중의 어느 한 항에 있어서, 기능 소자로서 유기 EL 소자를 수득하는, 기능 소자의 제조방법.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP99-086944 | 1999-03-29 | ||
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CN (1) | CN1310930A (ko) |
DE (1) | DE60045092D1 (ko) |
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CN111876020B (zh) * | 2020-08-06 | 2021-11-05 | 中国科学院长春应用化学研究所 | 一种有机发光材料墨水及其制备方法和喷墨打印方法 |
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US10325962B2 (en) | 2015-04-13 | 2019-06-18 | Samsung Display Co., Ltd. | Display device and method of manufacturing same |
US10811467B2 (en) | 2015-04-13 | 2020-10-20 | Samsung Display Co., Ltd. | Display device and method of manufacturing same |
US11387287B2 (en) | 2015-04-13 | 2022-07-12 | Samsung Display Co., Ltd. | Display device and method of manufacturing same |
US11800774B2 (en) | 2015-04-13 | 2023-10-24 | Samsung Display Co., Ltd. | Display device and method of manufacturing same |
Also Published As
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US9620719B2 (en) | 2017-04-11 |
JP4731629B2 (ja) | 2011-07-27 |
EP1083775A1 (en) | 2001-03-14 |
US20120263867A1 (en) | 2012-10-18 |
US20050156148A1 (en) | 2005-07-21 |
US20080305245A1 (en) | 2008-12-11 |
HK1128714A1 (en) | 2009-11-06 |
EP1083775A4 (en) | 2005-12-07 |
US6878312B1 (en) | 2005-04-12 |
DE60045092D1 (de) | 2010-11-25 |
JP4486261B2 (ja) | 2010-06-23 |
US8231932B2 (en) | 2012-07-31 |
CN1310930A (zh) | 2001-08-29 |
TW508975B (en) | 2002-11-01 |
US8187669B2 (en) | 2012-05-29 |
KR20010043918A (ko) | 2001-05-25 |
JP2011042794A (ja) | 2011-03-03 |
JP2010157751A (ja) | 2010-07-15 |
US20090186161A1 (en) | 2009-07-23 |
EP1083775B1 (en) | 2010-10-13 |
JP5286339B2 (ja) | 2013-09-11 |
WO2000059267A1 (fr) | 2000-10-05 |
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