JP2014075344A - 有機層をインクジェット印刷するためのアリールオキシアルキルカルボキシレート溶媒組成物 - Google Patents
有機層をインクジェット印刷するためのアリールオキシアルキルカルボキシレート溶媒組成物 Download PDFInfo
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- JP2014075344A JP2014075344A JP2013195075A JP2013195075A JP2014075344A JP 2014075344 A JP2014075344 A JP 2014075344A JP 2013195075 A JP2013195075 A JP 2013195075A JP 2013195075 A JP2013195075 A JP 2013195075A JP 2014075344 A JP2014075344 A JP 2014075344A
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- 239000002904 solvent Substances 0.000 title claims abstract description 67
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 239000012044 organic layer Substances 0.000 title claims abstract description 29
- 238000007641 inkjet printing Methods 0.000 title abstract description 17
- 239000007788 liquid Substances 0.000 claims abstract description 40
- 239000000463 material Substances 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 238000009835 boiling Methods 0.000 claims abstract description 21
- 239000004065 semiconductor Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 239000010410 layer Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical group CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 claims description 11
- BZCKRPHEZOHHBK-UHFFFAOYSA-N methyl 2-phenoxyacetate Chemical group COC(=O)COC1=CC=CC=C1 BZCKRPHEZOHHBK-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- JYDHZOIDIWUHDB-UHFFFAOYSA-N 1-(4-phenylpiperidin-4-yl)ethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)C)CCNCC1 JYDHZOIDIWUHDB-UHFFFAOYSA-N 0.000 claims 1
- 150000003384 small molecules Chemical class 0.000 abstract description 7
- 238000010129 solution processing Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 239000012530 fluid Substances 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 230000009286 beneficial effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
-
- 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
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- 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
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- 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
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Landscapes
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Abstract
【解決手段】有機電子デバイス(例えば、OLED)の有機層を形成するための液体組成物(例えば、インクジェット流体)が、溶媒に混合された低分子有機半導体材料を含み、前記溶媒の化合物は、以下の式によって表される:
(式中、R1は、C1−6アルキルであり、R2は、C1−6アルキルであり、R3は、C1−6アルキル及び低級アリールから独立して選択される1以上の任意の置換基である)。
【選択図】なし
Description
Claims (20)
- 0.01質量%〜10質量%の濃度の低分子有機半導体材料と、
25℃以下の融点を有する溶媒であって、前記溶媒の化合物が、
によって表される溶媒とを含むことを特徴とする液体組成物。 - 溶媒が、1atmで260℃以下の沸点を有する請求項1に記載の液体組成物。
- 溶媒が、1atmで150℃〜260℃の沸点を有する請求項2に記載の液体組成物。
- 溶媒の化合物が、166〜400の分子量を有する請求項1に記載の液体組成物。
- 低分子有機半導体材料が、リン光発光化合物である請求項1に記載の液体組成物。
- 低分子ホスト化合物を更に含む請求項5に記載の液体組成物。
- 有機半導体材料が、電荷輸送材料である請求項1に記載の液体組成物。
- 液体組成物が、23℃で5cPs〜15cPsの粘度を有する請求項1に記載の液体組成物。
- 溶媒が、23℃で5cPs〜15cPsの粘度を有する請求項1に記載の液体組成物。
- 溶媒が、フェノキシ酢酸メチル又はフェノキシ酢酸エチルである請求項1に記載の液体組成物。
- 有機半導体材料が、3,000以下の分子量を有する請求項1に記載の液体組成物。
- 溶媒ブレンドを形成するために別の溶媒を更に含む請求項1に記載の液体組成物。
- 別の溶媒が、3−フェノキシトルエンである請求項12に記載の液体組成物。
- 溶媒が、1atmで150℃〜260℃の沸点、23℃で5cPs〜15cPsの粘度、及び166〜400の分子量を有する請求項1に記載の液体組成物。
- 有機電子デバイス用の有機層を形成する方法であって、
請求項1に記載の液体組成物を表面に付着させる工程と、
前記液体組成物を乾燥させて、前記表面上に有機層を形成する工程とを含むことを特徴とする方法。 - 有機電子デバイスが、有機発光デバイスであり、有機層が、発光層である請求項15に記載の方法。
- 表面が、電子デバイスの別の有機層又は電極の表面である請求項16に記載の方法。
- アノードと、
カソードと、
前記アノードと前記カソードとの間に存在する有機層であって、請求項15に記載の方法によって作製される前記有機層とを含むことを特徴とする有機電子デバイス。 - 有機層が、発光層である請求項18に記載のデバイス。
- 低分子有機半導体材料が、リン光発光化合物である請求項19に記載のデバイス。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/644,480 US9252363B2 (en) | 2012-10-04 | 2012-10-04 | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
US13/644,480 | 2012-10-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014075344A true JP2014075344A (ja) | 2014-04-24 |
JP6249700B2 JP6249700B2 (ja) | 2017-12-20 |
Family
ID=50432033
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013195075A Active JP6249700B2 (ja) | 2012-10-04 | 2013-09-20 | 有機層をインクジェット印刷するためのアリールオキシアルキルカルボキシレート溶媒組成物 |
Country Status (3)
Country | Link |
---|---|
US (1) | US9252363B2 (ja) |
JP (1) | JP6249700B2 (ja) |
KR (1) | KR102092973B1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015159077A (ja) * | 2014-02-25 | 2015-09-03 | 日立化成株式会社 | 有機エレクトロニクス素子の製造方法 |
WO2016125560A1 (ja) * | 2015-02-03 | 2016-08-11 | 住友化学株式会社 | 組成物およびそれを用いた発光素子 |
JP2017098490A (ja) * | 2015-11-27 | 2017-06-01 | 東ソー株式会社 | 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ |
WO2017154882A1 (ja) * | 2016-03-10 | 2017-09-14 | 住友化学株式会社 | 発光素子 |
JP2018529223A (ja) * | 2015-07-15 | 2018-10-04 | メルク パテント ゲーエムベーハー | 有機半導体化合物を含む組成物 |
Families Citing this family (9)
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KR101666781B1 (ko) * | 2013-06-28 | 2016-10-17 | 엘지디스플레이 주식회사 | 유기 발광 소자 |
CN107690720B (zh) | 2015-06-12 | 2020-04-03 | 默克专利有限公司 | 作为用于oled制剂的溶剂的含有非芳族环的酯 |
US20180320066A1 (en) * | 2015-11-12 | 2018-11-08 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Formulation for printed electronics and use of the same in electronic device |
CN108291103B (zh) | 2015-11-12 | 2021-12-07 | 广州华睿光电材料有限公司 | 印刷组合物、包含其的电子器件及功能材料薄膜的制备方法 |
WO2017102048A1 (en) | 2015-12-15 | 2017-06-22 | Merck Patent Gmbh | Esters containing aromatic groups as solvents for organic electronic formulations |
KR102005867B1 (ko) * | 2016-06-17 | 2019-07-31 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
WO2018095381A1 (zh) | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | 印刷油墨组合物及其制备方法和用途 |
US11201299B2 (en) * | 2017-05-04 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10930864B2 (en) * | 2017-05-10 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
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KR20140044263A (ko) | 2014-04-14 |
JP6249700B2 (ja) | 2017-12-20 |
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