JP2008308685A - 組成物、薄膜の作製方法、及び発光素子の作製方法 - Google Patents
組成物、薄膜の作製方法、及び発光素子の作製方法 Download PDFInfo
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- JP2008308685A JP2008308685A JP2008129175A JP2008129175A JP2008308685A JP 2008308685 A JP2008308685 A JP 2008308685A JP 2008129175 A JP2008129175 A JP 2008129175A JP 2008129175 A JP2008129175 A JP 2008129175A JP 2008308685 A JP2008308685 A JP 2008308685A
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 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
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
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- 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
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- 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
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- 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
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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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Abstract
Description
本実施の形態では、本発明の組成物及び組成物を用いた薄膜の作製方法について説明する。
本発明のアントラセン誘導体及び溶媒を有する組成物を用いて湿式法により形成した薄膜を有する発光素子の一態様について図1(A)を用いて以下に説明する。
本実施の形態は、本発明に係る複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)の態様について、図3を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する積層型発光素子である。
本実施の形態では、本発明のアントラセン誘導体及び溶媒を有する組成物を用いて作製された発光装置について説明する。
本実施の形態では、実施の形態4に示す発光装置をその一部に含む本発明の電子機器について説明する。
まず、作製例1としてアントラセン誘導体として実施の形態1の構造式(11)で表される9−[4−(N−カルバゾリル)]フェニル−10−フェニルアントラセン(略称:CzPA)、溶媒としてトルエンを用いた例を示す。
次に、作製例2としてアントラセン誘導体として実施の形態1の構造式(17)で表される9−(4−tert−ブチルフェニル)−10−[4−(カルバゾール−9−イル)]フェニルアントラセン(略称:PTBCzPA)、溶媒としてトルエンを用いた例を示す。
比較例として9、10−ジフェニルアントラセン(略称:DPAnth)を溶媒トルエンに溶解し組成物を形成し、湿式法により薄膜を形成した例を示す。
(i)9−(4−tert−ブチルフェニル)アントラセンの合成
9−(4−tert−ブチルフェニル)アントラセンの合成スキームを(D−1)に示す。
9−ブロモ−10−(4−tert−ブチルフェニル)アントラセンの合成スキームを(D−2)に示す。
PTBCzPAの合成スキームを(D−3)に示す。
2−ブロモ−9,10−アントラキノンの合成スキームを(C−1)に示す。
2−ブロモ−9,10−ジフェニル−9,10−ジヒドロアントラセン−9,10−ジオールの合成スキームを(C−2)に示す。
2−ブロモ−9,10−ジフェニルアントラセンの合成スキームを(C−3)に示す。
3−ブロモ−9−フェニルカルバゾールの合成スキームを(C−5)に示す。
N−フェニル−(9−フェニル−9H−カルバゾール−3−イル)アミン(略称:PCA)の合成スキームを(C−6)に示す。
2PCAPAの合成スキームを(C−7)に示す。
Claims (16)
- 請求項1乃至10のいずれか一項において、前記溶媒は芳香環を有する溶媒であることを特徴とする組成物。
- 請求項1乃至11のいずれか一項に記載の組成物を基板上に塗布し、溶媒を除去することを特徴とする薄膜の作製方法。
- 請求項1乃至11のいずれか一項に記載の組成物を基板上に塗布し、加熱処理を行うことで溶媒を除去することを特徴とする薄膜の作製方法。
- 第1の電極を形成し、
請求項1乃至11のいずれか一項に記載の組成物を前記第1の電極上に塗布し、溶媒を除去し発光物質を含む層を形成し、
前記発光物質を含む層上に第2の電極を形成することを特徴とする発光素子の作製方法。 - 請求項14において、前記発光物質を含む層の前記第1の電極側か前記第2の電極側の少なくともどちらか一方に、塗布法により機能層を形成することを特徴とする発光素子の作製方法。
- 請求項14において、前記発光物質を含む層の前記第1の電極側か前記第2の電極側の少なくともどちらか一方に、蒸着法により機能層を形成することを特徴とする発光素子の作製方法。
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JP2022027777A (ja) * | 2016-02-26 | 2022-02-14 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器および照明装置 |
JP7297852B2 (ja) | 2016-02-26 | 2023-06-26 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器および照明装置 |
JPWO2018178818A1 (ja) * | 2017-03-31 | 2020-02-27 | 株式会社半導体エネルギー研究所 | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
WO2018178818A1 (ja) * | 2017-03-31 | 2018-10-04 | 株式会社半導体エネルギー研究所 | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
WO2020039708A1 (ja) | 2018-08-23 | 2020-02-27 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
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