JP2020107868A - 有機エレクトロルミネッセンス素子およびその製造方法 - Google Patents
有機エレクトロルミネッセンス素子およびその製造方法 Download PDFInfo
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- JP2020107868A JP2020107868A JP2018248433A JP2018248433A JP2020107868A JP 2020107868 A JP2020107868 A JP 2020107868A JP 2018248433 A JP2018248433 A JP 2018248433A JP 2018248433 A JP2018248433 A JP 2018248433A JP 2020107868 A JP2020107868 A JP 2020107868A
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- 125000003118 aryl group Chemical group 0.000 claims description 18
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- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-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
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Abstract
Description
前記電子輸送性化合物は下記化合物群(1)から選択される化合物である、および/または前記正孔輸送性化合物は下記化合物群(2)から選択される化合物である、有機エレクトロルミネッセンス素子を提供する。
前記電子輸送性化合物は下記化合物群(1)から選択される化合物である、および/または前記正孔輸送性化合物は下記化合物群(2)から選択される化合物である、有機エレクトロルミネッセンス素子である。
本発明に係る電子輸送性化合物は、本発明の効果を効率よく発現させる観点から、下記化合物群(1)から選択される化合物であることが好ましい。
Arは、それぞれ独立して、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基である。
本発明に係る正孔輸送性化合物は、本発明の効果を効率よく発現させる観点から、下記化合物群(2)から選択される化合物であることが好ましい。
Arは、それぞれ独立して、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基である。
本発明に係るワイドギャップ化合物は、HOMO−LUMOエネルギーギャップ(Eg)が3.3eV以上である化合物である。HOMO−LUMOエネルギーギャップ(Eg)が3.3eV未満の場合、ワイドギャップ化合物をホスト材料として適用して得られる長寿命化効果等が低下する。なお、HOMO−LUMOエネルギーギャップ(Eg)の上限は、特に制限されないが、好ましくは4eV以下である。
Ar1は、それぞれ独立して、水素原子、置換もしくは非置換のアリール基、または置換もしくは非置換の1価の窒素含有複素環基であり、ただし、2つのAr1が同時に水素原子であることはなく、
Ar2は、それぞれ独立して、フェニル基、複数の芳香族炭化水素環が単結合で直接結合している炭化水素環集合基、または置換もしくは非置換のヘテロアリール基であり、
Ar3は、それぞれ独立して、置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基であり、
Ar4は、水素原子、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基である。
以下では、図1を参照しながら、本実施形態に係る有機エレクトロルミネッセンス素子(有機EL素子)について、詳細に説明する。図1は、本実施形態に係る有機EL素子を示す模式図である。しかしながら、本実施形態に係る有機EL素子の構造は、図1に示す形態に限定されるものではない。
本実施形態に係る発光層形成用組成物は、有機EL素子の発光層を塗布法により形成するために用いられる。このような発光層形成用組成物は、本発明に係るホスト化合物と、溶媒と、を含む。
(実施例1)
国際公開第2011/159872号に記載のConpound Tの製法に準拠して、下記化学式で表されるポリマーP−1を合成した。ゲル浸透クロマトグラフィー(GPC)により測定したP−1の数平均分子量(Mn)は141,000であり、重量平均分子量(Mw)は511,000であった。
ホスト化合物の含有質量比を下記表1のように変更したこと以外は、実施例1と同様にして、有機エレクトロルミネッセンス素子を作製した。
作製した有機エレクトロルミネッセンス素子の発光効率および発光寿命を、以下の方法にて評価した。なお、発光効率は電流効率(cd/A)で評価した。
発光層のホスト化合物を下記表2に示す構成に変更したこと以外は、実施例1と同様にして、有機EL素子を作製し評価した。評価結果を下記表2に示す。
発光層のホスト化合物を下記表3に示す構成に変更したこと以外は、実施例1と同様にして、有機EL素子を作製し評価した。評価結果を下記表3に示す。
発光層のホスト化合物を下記表4に示す構成に変更したこと以外は、実施例1と同様にして、有機EL素子を作製し評価した。評価結果を下記表3に示す。
発光層のホスト化合物を下記表5に示す構成に変更し、さらにドーパント材料を下記化学式で表される白金錯体に変更したこと以外は、実施例1と同様にして、有機EL素子を作製し評価した。評価結果を下記表5に示す。
発光層のホスト化合物を下記表6に示す構成に変更し、さらに、ドーパント材料を下記化学式で表される赤燐光発光錯体(Ir(piq)2(acac))に変更したこと以外は、実施例1と同様にして、有機EL素子を作製した。性能評価は輝度2000nitの条件で行った。評価結果を下記表6に示す。
発光層のホスト化合物を下記表7に示す構成に変更し、さらに、ドーパント材料を下記化学式で表される青燐光発光錯体(FIrPic)に変更したこと以外は、実施例1と同様にして、有機EL素子を作製した。性能評価を輝度1000nitの条件で行い、寿命は初期輝度の70%になるまでの時間(LT70寿命(hrs))を評価した。評価結果を下記表7に示す。
発光層のホスト化合物を下記表8に示す構成に変更し、さらに、ドーパント材料を下記化学式で表される化合物(Blue Dopant−A)に変更したこと以外は、実施例1と同様にして、有機EL素子を作製した。性能評価は輝度1000nitの条件で行った。評価結果を下記表8に示す。
110 基板、
120 第1電極、
130 正孔注入層、
140 正孔輸送層、
150 発光層、
160 電子輸送層、
170 電子注入層、
180 第2電極。
Claims (6)
- 一対の電極間に発光層を有する有機エレクトロルミネッセンス素子であって、
前記発光層は、
少なくとも1種の電子輸送性化合物と、
少なくとも1種の正孔輸送性化合物と、
HOMO−LUMOエネルギーギャップが3.3eV以上である少なくとも1種のワイドギャップ化合物と、
を含み、
前記電子輸送性化合物は下記化合物群(1)から選択される化合物である、および/または前記正孔輸送性化合物は下記化合物群(2)から選択される化合物である、有機エレクトロルミネッセンス素子:
上記化合物群(1)および化合物群(2)中のArは、それぞれ独立して、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基である。 - 前記ワイドギャップ化合物は、下記化合物群(3)から選択される化合物である、請求項1に記載の有機エレクトロルミネッセンス素子:
上記化合物群(3)中、
Ar1は、それぞれ独立して、水素原子、置換もしくは非置換のアリール基、または置換もしくは非置換の1価の窒素含有複素環基であり、ただし、2つのAr1が同時に水素原子であることはなく、
Ar2は、それぞれ独立して、フェニル基、複数の芳香族炭化水素環が単結合で直接結合している炭化水素環集合基、または置換もしくは非置換のヘテロアリール基であり、
Ar3は、それぞれ独立して、置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基であり、
Ar4は、水素原子、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基である。 - 前記発光層は、
前記化合物群(1)から選択される少なくとも1種の電子輸送性化合物および前記化合物群(2)から選択される少なくとも1種の正孔輸送性化合物を含む、請求項1または2に記載の有機エレクトロルミネッセンス素子。 - 前記発光層中の前記正孔輸送性化合物の含有量が25質量%超である、請求項1〜3のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、蛍光発光性化合物または燐光発光性化合物を含む、請求項1〜4のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- 少なくとも1種の電子輸送性化合物と、
少なくとも1種の正孔輸送性化合物と、
HOMO−LUMOエネルギーギャップが3.3eV以上である少なくとも1種のワイドギャップ化合物と、
溶媒と、
を含む組成物を塗布することを有する、有機エレクトロルミネッセンス素子の製造方法であって、
前記電子輸送性化合物は下記化合物群(1)から選択される化合物である、および/または前記正孔輸送性化合物は下記化合物群(2)から選択される化合物である、有機エレクトロルミネッセンス素子の製造方法:
上記化合物群(1)および化合物群(2)中のArは、それぞれ独立して、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基である。
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JP2020105153A (ja) * | 2018-12-28 | 2020-07-09 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 化合物、組成物、液状組成物、有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子 |
WO2022255428A1 (ja) * | 2021-06-04 | 2022-12-08 | 三菱ケミカル株式会社 | 芳香族化合物、有機電界発光素子、組成物及び有機電界発光素子の製造方法 |
WO2022255403A1 (ja) * | 2021-06-04 | 2022-12-08 | 三菱ケミカル株式会社 | 化合物及び有機電界発光素子 |
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EP4307402A1 (en) * | 2021-04-21 | 2024-01-17 | Lg Chem, Ltd. | Organic light emitting device |
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JP2020105153A (ja) * | 2018-12-28 | 2020-07-09 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 化合物、組成物、液状組成物、有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子 |
JP7396795B2 (ja) | 2018-12-28 | 2023-12-12 | 三星電子株式会社 | 化合物、組成物、液状組成物、有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子 |
WO2022255428A1 (ja) * | 2021-06-04 | 2022-12-08 | 三菱ケミカル株式会社 | 芳香族化合物、有機電界発光素子、組成物及び有機電界発光素子の製造方法 |
WO2022255403A1 (ja) * | 2021-06-04 | 2022-12-08 | 三菱ケミカル株式会社 | 化合物及び有機電界発光素子 |
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