WO2007015781A2 - Low voltage organic electroluminescent element - Google Patents
Low voltage organic electroluminescent element Download PDFInfo
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- WO2007015781A2 WO2007015781A2 PCT/US2006/027558 US2006027558W WO2007015781A2 WO 2007015781 A2 WO2007015781 A2 WO 2007015781A2 US 2006027558 W US2006027558 W US 2006027558W WO 2007015781 A2 WO2007015781 A2 WO 2007015781A2
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- 239000000463 material Substances 0.000 claims abstract description 195
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 25
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- 238000012360 testing method Methods 0.000 claims description 20
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- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 claims 1
- ZMLPKJYZRQZLDA-UHFFFAOYSA-N 1-(2-phenylethenyl)-4-[4-(2-phenylethenyl)phenyl]benzene Chemical group C=1C=CC=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC1=CC=CC=C1 ZMLPKJYZRQZLDA-UHFFFAOYSA-N 0.000 claims 1
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- DKBBJDJJFNFSOB-UHFFFAOYSA-N n-[4-[4-[n-(1,2-dihydroacenaphthylen-3-yl)anilino]phenyl]phenyl]-n-phenyl-1,2-dihydroacenaphthylen-3-amine;n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1.C1=CC(C2=3)=CC=CC=3CCC2=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=2CCC3=CC=CC(C=23)=CC=1)C1=CC=CC=C1 DKBBJDJJFNFSOB-UHFFFAOYSA-N 0.000 description 1
- UHVLDCDWBKWDDN-UHFFFAOYSA-N n-phenyl-n-[4-[4-(n-pyren-2-ylanilino)phenyl]phenyl]pyren-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=CC3=CC=CC4=CC=C(C2=C43)C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC4=CC=CC5=CC=C(C3=C54)C=2)C=C1 UHVLDCDWBKWDDN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- USPVIMZDBBWXGM-UHFFFAOYSA-N nickel;oxotungsten Chemical compound [Ni].[W]=O USPVIMZDBBWXGM-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
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- 238000000059 patterning Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
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- 150000002987 phenanthrenes Chemical class 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
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- 150000004032 porphyrins Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical group C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 238000007789 sealing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
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- 150000003346 selenoethers Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
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- 239000003115 supporting electrolyte Substances 0.000 description 1
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- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
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- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-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]
- H10K50/18—Carrier blocking layers
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008523937A JP2009503849A (ja) | 2005-07-28 | 2006-07-14 | 低電圧有機エレクトロルミネッセンス素子 |
| EP06787462.8A EP1911069B1 (en) | 2005-07-28 | 2006-07-14 | Low voltage organic electroluminescent element |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/192,072 US7563518B2 (en) | 2005-07-28 | 2005-07-28 | Low voltage organic electroluminescent element |
| US11/192,072 | 2005-07-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2007015781A2 true WO2007015781A2 (en) | 2007-02-08 |
| WO2007015781A3 WO2007015781A3 (en) | 2007-04-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2006/027558 WO2007015781A2 (en) | 2005-07-28 | 2006-07-14 | Low voltage organic electroluminescent element |
Country Status (4)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008258603A (ja) * | 2007-03-14 | 2008-10-23 | Samsung Sdi Co Ltd | アントラセン誘導体化合物を含む有機膜を備える有機発光素子 |
| JP2011511458A (ja) * | 2008-01-30 | 2011-04-07 | グローバル・オーエルイーディー・テクノロジー・リミテッド・ライアビリティ・カンパニー | 二重の正孔ブロック層を有するリン光ｏｌｅｄ |
| JP2012513668A (ja) * | 2008-12-22 | 2012-06-14 | メルク パテント ゲーエムベーハー | トリアジン誘導体を含む有機エレクトロルミネセンス素子 |
| WO2013026515A1 (de) | 2011-08-22 | 2013-02-28 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060204784A1 (en) * | 2005-03-10 | 2006-09-14 | Begley William J | Organic light-emitting devices with mixed electron transport materials |
| US20060246315A1 (en) * | 2005-04-27 | 2006-11-02 | Begley William J | Phosphorescent oled with mixed electron transport materials |
| US20070048545A1 (en) * | 2005-08-31 | 2007-03-01 | Eastman Kodak Company | Electron-transporting layer for white OLED device |
| DE502005009802D1 (de) * | 2005-11-10 | 2010-08-05 | Novaled Ag | Dotiertes organisches Halbleitermaterial |
| JP4673279B2 (ja) * | 2005-12-20 | 2011-04-20 | 三星モバイルディスプレイ株式會社 | 有機発光表示素子及びその製造方法 |
| US7919010B2 (en) * | 2005-12-22 | 2011-04-05 | Novaled Ag | Doped organic semiconductor material |
| ES2310380T3 (es) | 2006-03-21 | 2009-01-01 | Novaled Ag | Radical o dirradical heterociclicos, sus dimeros, oligomeros, polimeros, compuestos diespiro y policiclos, su utilizacion, material semiconductor organico asi como componente electronico. |
| EP1837927A1 (de) * | 2006-03-22 | 2007-09-26 | Novaled AG | Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern |
| US20080032123A1 (en) * | 2006-08-02 | 2008-02-07 | Spindler Jeffrey P | Dual electron-transporting layer for oled device |
| DE102007012794B3 (de) | 2007-03-16 | 2008-06-19 | Novaled Ag | Pyrido[3,2-h]chinazoline und/oder deren 5,6-Dihydroderivate, deren Herstellungsverfahren und diese enthaltendes dotiertes organisches Halbleitermaterial |
| DE102007018456B4 (de) * | 2007-04-19 | 2022-02-24 | Novaled Gmbh | Verwendung von Hauptgruppenelementhalogeniden und/oder -pseudohalogeniden, organisches halbleitendes Matrixmaterial, elektronische und optoelektronische Bauelemente |
| EP1988587B1 (de) | 2007-04-30 | 2016-12-07 | Novaled GmbH | Oxokohlenstoff-, Pseudooxokohlenstoff- und Radialenverbindungen sowie deren Verwendung |
| EP1990847B1 (de) * | 2007-05-10 | 2018-06-20 | Novaled GmbH | Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials |
| DE102007031220B4 (de) | 2007-07-04 | 2022-04-28 | Novaled Gmbh | Chinoide Verbindungen und deren Verwendung in halbleitenden Matrixmaterialien, elektronischen und optoelektronischen Bauelementen |
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| JP2015111679A (ja) * | 2008-12-22 | 2015-06-18 | メルク パテント ゲーエムベーハー | トリアジン誘導体を含む有機エレクトロルミネセンス素子 |
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| WO2013026515A1 (de) | 2011-08-22 | 2013-02-28 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1911069A2 (en) | 2008-04-16 |
| JP2009503849A (ja) | 2009-01-29 |
| US7563518B2 (en) | 2009-07-21 |
| EP1911069B1 (en) | 2018-08-22 |
| WO2007015781A3 (en) | 2007-04-19 |
| US20070026257A1 (en) | 2007-02-01 |
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