TWI293011B - - Google Patents
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- Publication number
- TWI293011B TWI293011B TW091110879A TW91110879A TWI293011B TW I293011 B TWI293011 B TW I293011B TW 091110879 A TW091110879 A TW 091110879A TW 91110879 A TW91110879 A TW 91110879A TW I293011 B TWI293011 B TW I293011B
- Authority
- TW
- Taiwan
- Prior art keywords
- light
- layer
- emitting
- compound
- organic electroluminescent
- Prior art date
Links
- 239000010410 layer Substances 0.000 claims description 324
- 239000000463 material Substances 0.000 claims description 169
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 claims description 76
- 230000005684 electric field Effects 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000004020 luminiscence type Methods 0.000 claims description 36
- 230000001737 promoting effect Effects 0.000 claims description 29
- 230000005525 hole transport Effects 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 20
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 claims description 18
- 238000002513 implantation Methods 0.000 claims description 12
- 239000007943 implant Substances 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 6
- 238000004776 molecular orbital Methods 0.000 claims description 5
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 description 56
- 229940125782 compound 2 Drugs 0.000 description 43
- -1 porphyrin compound Chemical class 0.000 description 32
- 239000000126 substance Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 230000008859 change Effects 0.000 description 21
- 230000015556 catabolic process Effects 0.000 description 17
- 238000006731 degradation reaction Methods 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- 238000001771 vacuum deposition Methods 0.000 description 15
- 238000001748 luminescence spectrum Methods 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000009826 distribution Methods 0.000 description 10
- 238000005401 electroluminescence Methods 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 238000010276 construction Methods 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 230000006866 deterioration Effects 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 230000008033 biological extinction Effects 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
- 229940125797 compound 12 Drugs 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 230000002238 attenuated effect Effects 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000012494 forced degradation Methods 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 238000000103 photoluminescence spectrum Methods 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000010363 phase shift Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002111659 | 2002-04-15 | ||
| JP2002138212A JP2004006066A (ja) | 2002-04-15 | 2002-05-14 | 有機電界発光素子及び発光装置 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI293011B true TWI293011B (enExample) | 2008-01-21 |
Family
ID=29253553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091110879A TWI293011B (enExample) | 2002-04-15 | 2002-05-23 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20050064232A1 (enExample) |
| EP (1) | EP1511363A4 (enExample) |
| JP (1) | JP2004006066A (enExample) |
| KR (1) | KR20040044066A (enExample) |
| CN (1) | CN100442568C (enExample) |
| TW (1) | TWI293011B (enExample) |
| WO (1) | WO2003088721A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4001118B2 (ja) * | 2003-03-24 | 2007-10-31 | ソニー株式会社 | 有機電界発光素子及びアミノモノスチリルナフタレン化合物 |
| EP2924094B1 (en) * | 2003-06-02 | 2017-04-05 | UDC Ireland Limited | Organic electroluminescent devices and metal complex compounds |
| KR100981015B1 (ko) * | 2004-03-25 | 2010-09-07 | 사천홍시현시기건유한공사 | 유기 전계 발광 소자의 제조 방법 |
| CN100455151C (zh) * | 2005-08-30 | 2009-01-21 | 铼宝科技股份有限公司 | 有机电激发光元件及其制造方法 |
| US20070215889A1 (en) * | 2006-03-20 | 2007-09-20 | Semiconductor Energy Laboratory Co., Ltd. | Aromatic amine compound, and light-emitting element, light-emitting device, and electronic appliance using the aromatic amine compound |
| JP5207645B2 (ja) * | 2006-03-29 | 2013-06-12 | キヤノン株式会社 | 多色有機発光装置 |
| CN101919082B (zh) * | 2007-12-28 | 2012-05-30 | 夏普株式会社 | 有机电致发光元件 |
| KR101320107B1 (ko) * | 2007-12-31 | 2013-10-18 | 엘지디스플레이 주식회사 | 유기전계발광표시장치 |
| US8242489B2 (en) * | 2009-12-17 | 2012-08-14 | Global Oled Technology, Llc. | OLED with high efficiency blue light-emitting layer |
| JP6094480B2 (ja) * | 2011-06-15 | 2017-03-15 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置、表示装置及び有機エレクトロルミネッセンス素子の製造方法 |
| KR101963226B1 (ko) * | 2012-02-29 | 2019-04-01 | 삼성전자주식회사 | 트랜지스터와 그 제조방법 및 트랜지스터를 포함하는 전자소자 |
| JP2018022862A (ja) * | 2016-07-20 | 2018-02-08 | 株式会社Ｊｏｌｅｄ | 有機電界発光素子、有機電界発光装置および電子機器 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2814435B2 (ja) * | 1987-03-02 | 1998-10-22 | イーストマン・コダック・カンパニー | 改良薄膜発光帯をもつ電場発光デバイス |
| JP2869446B2 (ja) * | 1989-01-13 | 1999-03-10 | 株式会社リコー | 電界発光素子 |
| US5085946A (en) * | 1989-01-13 | 1992-02-04 | Ricoh Company, Ltd. | Electroluminescence device |
| JP2879080B2 (ja) * | 1989-03-23 | 1999-04-05 | 株式会社リコー | 電界発光素子 |
| JP3712760B2 (ja) * | 1995-05-17 | 2005-11-02 | Ｔｄｋ株式会社 | 有機ｅｌ素子 |
| JPH10270166A (ja) * | 1997-03-27 | 1998-10-09 | Tatsuo Mori | 電界発光素子 |
| DE19803889A1 (de) * | 1998-01-31 | 1999-08-05 | Bosch Gmbh Robert | Elektrolumineszierende Anordnung unter Verwendung von dotierten Blendsystemen |
| JP3852517B2 (ja) * | 1998-05-18 | 2006-11-29 | ソニー株式会社 | 有機電界発光素子 |
| JP3555736B2 (ja) | 1998-06-26 | 2004-08-18 | ソニー株式会社 | 有機電界発光素子 |
| JP2001052870A (ja) * | 1999-06-03 | 2001-02-23 | Tdk Corp | 有機ｅｌ素子 |
| JP2001291591A (ja) * | 2000-04-07 | 2001-10-19 | Sony Corp | 有機電界発光素子及び発光装置 |
| JP4273191B2 (ja) * | 2001-03-01 | 2009-06-03 | 三星モバイルディスプレイ株式會社 | 有機発光デバイス |
-
2002
- 2002-05-14 JP JP2002138212A patent/JP2004006066A/ja active Pending
- 2002-05-23 TW TW091110879A patent/TWI293011B/zh not_active IP Right Cessation
- 2002-05-31 WO PCT/JP2002/005366 patent/WO2003088721A1/ja not_active Ceased
- 2002-05-31 KR KR1020027012973A patent/KR20040044066A/ko not_active Ceased
- 2002-05-31 US US10/240,328 patent/US20050064232A1/en not_active Abandoned
- 2002-05-31 EP EP02730838A patent/EP1511363A4/en not_active Withdrawn
- 2002-09-30 CN CNB021545545A patent/CN100442568C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1511363A1 (en) | 2005-03-02 |
| CN100442568C (zh) | 2008-12-10 |
| KR20040044066A (ko) | 2004-05-27 |
| CN1452439A (zh) | 2003-10-29 |
| EP1511363A4 (en) | 2010-08-25 |
| WO2003088721A1 (en) | 2003-10-23 |
| US20050064232A1 (en) | 2005-03-24 |
| JP2004006066A (ja) | 2004-01-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |