DE102008056391B4 - Organisches elektronisches Bauelement und Verfahren zu dessen Herstellung - Google Patents
Organisches elektronisches Bauelement und Verfahren zu dessen Herstellung Download PDFInfo
- Publication number
- DE102008056391B4 DE102008056391B4 DE102008056391.9A DE102008056391A DE102008056391B4 DE 102008056391 B4 DE102008056391 B4 DE 102008056391B4 DE 102008056391 A DE102008056391 A DE 102008056391A DE 102008056391 B4 DE102008056391 B4 DE 102008056391B4
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- electronic component
- organic
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- organic compound
- metal complex
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- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 112
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 83
- 229910052751 metal Inorganic materials 0.000 claims abstract description 47
- 239000002184 metal Substances 0.000 claims abstract description 47
- 238000001704 evaporation Methods 0.000 claims abstract description 23
- 230000008020 evaporation Effects 0.000 claims abstract description 21
- 239000000758 substrate Substances 0.000 claims abstract description 20
- 239000003446 ligand Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 238000012546 transfer Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 238000000151 deposition Methods 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 229910052721 tungsten Inorganic materials 0.000 claims description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 claims description 2
- WGDRAVMHLDKGGA-UHFFFAOYSA-N prop-2-en-1-imine Chemical group [CH2]C=C[NH] WGDRAVMHLDKGGA-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000005259 measurement Methods 0.000 description 49
- 125000004429 atom Chemical group 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 14
- 229920000742 Cotton Polymers 0.000 description 13
- 238000004020 luminiscence type Methods 0.000 description 12
- 230000005855 radiation Effects 0.000 description 11
- 239000002800 charge carrier Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 8
- 150000002390 heteroarenes Chemical class 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 6
- 230000005669 field effect Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 4
- 241001295925 Gegenes Species 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- NFNALQOLQWJCNE-UHFFFAOYSA-N [Ir+3].C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1.C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1 Chemical compound [Ir+3].C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1.C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1 NFNALQOLQWJCNE-UHFFFAOYSA-N 0.000 description 2
- CIOWRYCRGAJGAW-UHFFFAOYSA-N c1cnccc1-c1cc(-c2ccncc2)nc(-c2ccncc2)n1 Chemical compound c1cnccc1-c1cc(-c2ccncc2)nc(-c2ccncc2)n1 CIOWRYCRGAJGAW-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 238000013021 overheating Methods 0.000 description 2
- -1 pyrimidyl arenes Chemical class 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DRGAZIDRYFYHIJ-UHFFFAOYSA-N 2,2':6',2''-terpyridine Chemical compound N1=CC=CC=C1C1=CC=CC(C=2N=CC=CC=2)=N1 DRGAZIDRYFYHIJ-UHFFFAOYSA-N 0.000 description 1
- 241001120493 Arene Species 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1-c1nnc(-c2cccc(-c3nnc(-c4ccc(C(C)(C)C)cc4)[o]3)c2)[o]1 Chemical compound CC(C)(C)c(cc1)ccc1-c1nnc(-c2cccc(-c3nnc(-c4ccc(C(C)(C)C)cc4)[o]3)c2)[o]1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QCLREVDZJZXEJE-UHFFFAOYSA-N c(cc1)ccc1N1c2ccccc2NC1c1cc(C(Nc2c3cccc2)N3c2ccccc2)cc(C(Nc2ccccc22)N2c2ccccc2)c1 Chemical compound c(cc1)ccc1N1c2ccccc2NC1c1cc(C(Nc2c3cccc2)N3c2ccccc2)cc(C(Nc2ccccc22)N2c2ccccc2)c1 QCLREVDZJZXEJE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
Images
Classifications
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- 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
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
-
- 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
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- High Energy & Nuclear Physics (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Photovoltaic Devices (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008056391.9A DE102008056391B4 (de) | 2008-09-26 | 2008-11-07 | Organisches elektronisches Bauelement und Verfahren zu dessen Herstellung |
| CN200980138172.2A CN102165622B (zh) | 2008-09-26 | 2009-09-25 | 有机电子元件及其制造方法 |
| KR1020117009229A KR101640621B1 (ko) | 2008-09-26 | 2009-09-25 | 유기 전자 소자 및 그 제조 방법 |
| JP2011528186A JP5650114B2 (ja) | 2008-09-26 | 2009-09-25 | 有機エレクトロニクス素子及びその製造方法 |
| PCT/DE2009/001359 WO2010034304A2 (de) | 2008-09-26 | 2009-09-25 | Organisches elektronisches bauelement und verfahren zu dessen herstellung |
| US13/121,090 US8558223B2 (en) | 2008-09-26 | 2009-09-25 | Organic electronic component and method for the production thereof |
| EP09741205.0A EP2342772B1 (de) | 2008-09-26 | 2009-09-25 | Organisches elektronisches bauelement und verfahren zu dessen herstellung |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008049286 | 2008-09-26 | ||
| DE102008049286.8 | 2008-09-26 | ||
| DE102008056391.9A DE102008056391B4 (de) | 2008-09-26 | 2008-11-07 | Organisches elektronisches Bauelement und Verfahren zu dessen Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE102008056391A1 DE102008056391A1 (de) | 2010-04-01 |
| DE102008056391B4 true DE102008056391B4 (de) | 2021-04-01 |
Family
ID=41719954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102008056391.9A Active DE102008056391B4 (de) | 2008-09-26 | 2008-11-07 | Organisches elektronisches Bauelement und Verfahren zu dessen Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8558223B2 (https=) |
| EP (1) | EP2342772B1 (https=) |
| JP (1) | JP5650114B2 (https=) |
| KR (1) | KR101640621B1 (https=) |
| CN (1) | CN102165622B (https=) |
| DE (1) | DE102008056391B4 (https=) |
| WO (1) | WO2010034304A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102471269B (zh) | 2010-01-15 | 2016-02-03 | 出光兴产株式会社 | 含氮杂环衍生物及含有它的有机电致发光元件 |
| DE102012200180A1 (de) * | 2012-01-09 | 2013-07-11 | Osram Opto Semiconductors Gmbh | Verfahren zur Herstellung optoelektronischer organischer Bauteile, Vorrichtung hierfür und optoelektronisches organisches Bauteil |
| CN103390631A (zh) * | 2012-05-11 | 2013-11-13 | 四川优的科技有限公司 | 一种oled显示器结构 |
| JP6060530B2 (ja) * | 2012-06-12 | 2017-01-18 | ソニー株式会社 | 有機電界発光素子及び表示装置 |
| JP2015060020A (ja) * | 2013-09-18 | 2015-03-30 | ソニー株式会社 | 表示装置及び電子機器 |
| EP3284801A1 (en) | 2016-08-19 | 2018-02-21 | Julius-Maximilians-Universität Würzburg | Ligands, electrochromic metallo-polymers obtained therewith and their use |
| CN107698568A (zh) * | 2017-09-26 | 2018-02-16 | 长春海谱润斯科技有限公司 | 一种联嘧啶衍生物的热激活延迟荧光材料及其有机电致发光器件 |
| CN109994651B (zh) * | 2017-12-29 | 2020-12-25 | 昆山国显光电有限公司 | 一种有机电致发光器件及其制备方法 |
| US11380852B2 (en) * | 2018-12-12 | 2022-07-05 | The Regents Of The University Of California | N-type dopants for efficient solar cells |
| KR102381634B1 (ko) * | 2019-07-05 | 2022-04-01 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR102291411B1 (ko) * | 2019-12-09 | 2021-08-23 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
| CN112194614B (zh) * | 2020-10-14 | 2022-04-26 | 新乡医学院 | 一种特异性识别Fe3+的三联吡啶荧光探针及其合成方法和应用 |
| CN115207228B (zh) * | 2021-04-08 | 2025-06-03 | 常州强力电子新材料股份有限公司 | 有机电致发光元件 |
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| DE10337346A1 (de) * | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
| DE10339772A1 (de) * | 2003-08-27 | 2005-04-14 | Novaled Gmbh | Licht emittierendes Bauelement und Verfahren zu seiner Herstellung |
| US20050231100A1 (en) * | 2002-08-12 | 2005-10-20 | Colorado State University Research | Low work function metal complexes and uses thereof |
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- 2009-09-25 CN CN200980138172.2A patent/CN102165622B/zh active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102165622B (zh) | 2014-09-17 |
| CN102165622A (zh) | 2011-08-24 |
| WO2010034304A3 (de) | 2010-06-03 |
| EP2342772B1 (de) | 2015-12-02 |
| KR20110084406A (ko) | 2011-07-22 |
| KR101640621B1 (ko) | 2016-07-18 |
| WO2010034304A2 (de) | 2010-04-01 |
| JP2012503867A (ja) | 2012-02-09 |
| JP5650114B2 (ja) | 2015-01-07 |
| US20110309340A1 (en) | 2011-12-22 |
| US8558223B2 (en) | 2013-10-15 |
| DE102008056391A1 (de) | 2010-04-01 |
| EP2342772A2 (de) | 2011-07-13 |
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