CN1192683C - 具有有机可溶性衍生物层的有机电致发光显示装置 - Google Patents
具有有机可溶性衍生物层的有机电致发光显示装置 Download PDFInfo
- Publication number
- CN1192683C CN1192683C CNB021524289A CN02152428A CN1192683C CN 1192683 C CN1192683 C CN 1192683C CN B021524289 A CNB021524289 A CN B021524289A CN 02152428 A CN02152428 A CN 02152428A CN 1192683 C CN1192683 C CN 1192683C
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- China
- Prior art keywords
- organic
- polymer
- layer
- soluble derivative
- luminescent layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000012535 impurity Substances 0.000 claims abstract description 8
- 229920000642 polymer Polymers 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 27
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- 239000000203 mixture Substances 0.000 claims description 14
- -1 Merlon Polymers 0.000 claims description 13
- 238000012546 transfer Methods 0.000 claims description 9
- 230000005012 migration Effects 0.000 claims description 8
- 238000013508 migration Methods 0.000 claims description 8
- 229920001059 synthetic polymer Polymers 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 238000009792 diffusion process Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 claims description 4
- GMEQIEASMOFEOC-UHFFFAOYSA-N 4-[3,5-bis[4-(4-methoxy-n-(4-methoxyphenyl)anilino)phenyl]phenyl]-n,n-bis(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=C(C=C(C=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 GMEQIEASMOFEOC-UHFFFAOYSA-N 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- 239000004642 Polyimide Substances 0.000 claims description 4
- 229920007962 Styrene Methyl Methacrylate Polymers 0.000 claims description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 4
- 229920001230 polyarylate Polymers 0.000 claims description 4
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 4
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 4
- 229920001721 polyimide Polymers 0.000 claims description 4
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 4
- 150000003233 pyrroles Chemical class 0.000 claims description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 238000003384 imaging method Methods 0.000 claims 2
- 239000010410 layer Substances 0.000 description 107
- 238000002347 injection Methods 0.000 description 21
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- 238000000034 method Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000005516 engineering process Methods 0.000 description 10
- 238000004528 spin coating Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 6
- 229920000767 polyaniline Polymers 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 229960002796 polystyrene sulfonate Drugs 0.000 description 2
- 239000011970 polystyrene sulfonate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001931 thermography Methods 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- IJVBYWCDGKXHKK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetraphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IJVBYWCDGKXHKK-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Classifications
-
- 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
- H10K71/18—Deposition of organic active material using non-liquid printing techniques, e.g. thermal transfer printing from a donor sheet
-
- 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]
- H10K50/14—Carrier transporting 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
Claims (15)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR74703/2001 | 2001-11-28 | ||
KR10-2001-0074703A KR100478522B1 (ko) | 2001-11-28 | 2001-11-28 | 유기 화합물 유도체막층을 포함하고 있는 고분자 유기전계 발광 소자 및 그 제조 방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1423512A CN1423512A (zh) | 2003-06-11 |
CN1192683C true CN1192683C (zh) | 2005-03-09 |
Family
ID=19716411
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB021524289A Expired - Lifetime CN1192683C (zh) | 2001-11-28 | 2002-11-27 | 具有有机可溶性衍生物层的有机电致发光显示装置 |
Country Status (3)
Country | Link |
---|---|
US (2) | US6853147B2 (zh) |
KR (1) | KR100478522B1 (zh) |
CN (1) | CN1192683C (zh) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100454500B1 (ko) * | 2001-12-22 | 2004-10-28 | 한국전자통신연구원 | 고효율 유기 전기 발광 소자 및 그 제조방법 |
KR100478524B1 (ko) * | 2002-06-28 | 2005-03-28 | 삼성에스디아이 주식회사 | 고분자 및 저분자 발광 재료의 혼합물을 발광 재료로사용하는 유기 전계 발광 소자 |
KR20050017169A (ko) * | 2003-08-08 | 2005-02-22 | 삼성에스디아이 주식회사 | 애노드 표면 개질층을 사용하는 유기 전계 발광 소자 |
US7893438B2 (en) * | 2003-10-16 | 2011-02-22 | Samsung Mobile Display Co., Ltd. | Organic light-emitting display device including a planarization pattern and method for manufacturing the same |
US7381579B2 (en) * | 2004-02-26 | 2008-06-03 | Samsung Sdi Co., Ltd. | Donor sheet, method of manufacturing the same, method of manufacturing TFT using the donor sheet, and method of manufacturing flat panel display device using the donor sheet |
KR100685404B1 (ko) * | 2004-10-11 | 2007-02-22 | 삼성에스디아이 주식회사 | 유기전계발광표시장치 및 그 제조방법 |
US7759856B2 (en) * | 2004-12-17 | 2010-07-20 | Honeywell International Inc. | Organic light emitting diode (OLED) having improved stability, luminance, and efficiency |
KR101074786B1 (ko) * | 2004-12-31 | 2011-10-19 | 삼성모바일디스플레이주식회사 | 트리페닐아민 유도체 구조를 함유한 폴리이미드를 포함한 전자차단층을 채용한 유기 전계 발광 소자 |
US20070128465A1 (en) * | 2005-12-05 | 2007-06-07 | General Electric Company | Transparent electrode for organic electronic devices |
KR101009644B1 (ko) * | 2008-08-26 | 2011-01-19 | 삼성모바일디스플레이주식회사 | 레이저 열전사용 도너 기판 및 이를 이용한 유기전계발광소자의 제조방법 |
KR101111435B1 (ko) * | 2009-03-11 | 2012-02-16 | 광 석 서 | 정공주입층 및 정공수송층 재료로 사용가능한 화합물 및 이를 이용한 유기발광소자 |
DE102010025547B4 (de) * | 2010-06-29 | 2023-05-11 | Samsung Display Co., Ltd. | Verwendung einer Zusammensetzung in einer Emitterschicht in einer optoelektronischen Vorrichtung zum Singulett-Harvesting mit organischen Molekülen, optoelektronische Vorrichtungen und Verfahren zu deren Herstellung |
DE102011089687A1 (de) | 2011-12-22 | 2013-06-27 | Hartmut Yersin | Singulett-Harvesting mit speziellen organischen Molekülen ohne Metallzentren für opto-elektronische Vorrichtungen |
TW201422056A (zh) * | 2012-07-20 | 2014-06-01 | Hitachi High Tech Corp | 雷射轉印方法及使用彼之雷射轉印設備 |
CN103779504A (zh) * | 2012-10-25 | 2014-05-07 | 东莞万士达液晶显示器有限公司 | 有机发光二极管封装结构 |
KR102215147B1 (ko) * | 2014-08-14 | 2021-02-15 | 삼성디스플레이 주식회사 | 유기발광 표시장치 |
CN111205721A (zh) * | 2020-03-07 | 2020-05-29 | 浙江大高镭射科技股份有限公司 | 一种多用途镭射转移涂料及其制备方法 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8909011D0 (en) * | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
JP2588280B2 (ja) * | 1989-07-10 | 1997-03-05 | シャープ株式会社 | 化合物半導体発光素子 |
EP0553950A3 (en) * | 1992-01-07 | 1994-11-23 | Toshiba Kk | Organic electroluminescent device |
US5998085A (en) * | 1996-07-23 | 1999-12-07 | 3M Innovative Properties | Process for preparing high resolution emissive arrays and corresponding articles |
JP3724589B2 (ja) * | 1996-07-29 | 2005-12-07 | ケンブリッジ ディスプレイ テクノロジー リミテッド | エレクトロルミネセンス素子 |
US6402579B1 (en) * | 1996-09-04 | 2002-06-11 | Cambridge Display Technology Limited | Electrode deposition for organic light-emitting devices |
KR100195175B1 (ko) * | 1996-12-23 | 1999-06-15 | 손욱 | 유기전자발광소자 유기박막용 도너필름, 이를 이용한 유기전자발광소자의 제조방법 및 그 방법에 따라 제조된 유기전자발광소자 |
US5965281A (en) * | 1997-02-04 | 1999-10-12 | Uniax Corporation | Electrically active polymer compositions and their use in efficient, low operating voltage, polymer light-emitting diodes with air-stable cathodes |
JP2845856B2 (ja) * | 1997-03-10 | 1999-01-13 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子の製造方法 |
JPH1140365A (ja) * | 1997-07-16 | 1999-02-12 | Tdk Corp | 有機el素子およびその製造方法 |
KR100254536B1 (ko) * | 1997-09-29 | 2000-05-01 | 정선종 | 두개의실릴기를갖는용해가능한피피브이유도체의합성방법및이를이용한전기발광소자 |
GB9724682D0 (en) * | 1997-11-21 | 1998-01-21 | Cambridge Display Tech Ltd | Electroluminescent device |
JPH11195487A (ja) * | 1997-12-27 | 1999-07-21 | Tdk Corp | 有機el素子 |
GB9823761D0 (en) * | 1998-11-02 | 1998-12-23 | South Bank Univ Entpr Ltd | Novel electroluminescent materials |
JP2000164361A (ja) * | 1998-11-25 | 2000-06-16 | Tdk Corp | 有機el素子 |
DE60035078T2 (de) * | 1999-01-15 | 2008-01-31 | 3M Innovative Properties Co., St. Paul | Herstellungsverfahren eines Donorelements für Übertragung durch Wärme |
DE69924155T2 (de) * | 1999-02-04 | 2006-04-13 | Dow Global Technologies, Inc., Midland | Fluoren-copolymere und daraus hergestellte vorrichtungen |
US6391482B1 (en) * | 1999-02-04 | 2002-05-21 | Matsushita Electric Industrial Co., Ltd. | Organic material for electroluminescent device and electroluminescent device using the same |
US6406802B1 (en) * | 1999-05-27 | 2002-06-18 | Tdk Corporation | Organic electroluminescent color display |
KR100626660B1 (ko) * | 1999-06-28 | 2006-09-22 | 한국전자통신연구원 | 상 분리를 이용한 고효율 고분자 발광소자 |
KR100644168B1 (ko) * | 1999-11-24 | 2006-11-13 | 고등기술연구원연구조합 | 전기적 활성을 갖는 유기복합박막을 포함하는유기전기발광소자 |
TW511394B (en) * | 2000-08-21 | 2002-11-21 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light emitting device |
TW589913B (en) * | 2001-01-18 | 2004-06-01 | Ind Tech Res Inst | Organic light-emitting device |
US6717181B2 (en) * | 2001-02-22 | 2004-04-06 | Semiconductor Energy Laboratory Co., Ltd. | Luminescent device having thin film transistor |
-
2001
- 2001-11-28 KR KR10-2001-0074703A patent/KR100478522B1/ko active IP Right Grant
-
2002
- 2002-06-13 US US10/167,651 patent/US6853147B2/en not_active Expired - Lifetime
- 2002-11-27 CN CNB021524289A patent/CN1192683C/zh not_active Expired - Lifetime
-
2004
- 2004-12-15 US US11/011,834 patent/US6989288B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US20030098646A1 (en) | 2003-05-29 |
US6989288B2 (en) | 2006-01-24 |
KR100478522B1 (ko) | 2005-03-28 |
US6853147B2 (en) | 2005-02-08 |
US20050095738A1 (en) | 2005-05-05 |
KR20030044114A (ko) | 2003-06-09 |
CN1423512A (zh) | 2003-06-11 |
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