JP6825194B2 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- JP6825194B2 JP6825194B2 JP2019073261A JP2019073261A JP6825194B2 JP 6825194 B2 JP6825194 B2 JP 6825194B2 JP 2019073261 A JP2019073261 A JP 2019073261A JP 2019073261 A JP2019073261 A JP 2019073261A JP 6825194 B2 JP6825194 B2 JP 6825194B2
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- 238000004528 spin coating Methods 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
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Description
(a)イオン化ポテンシャル[Ip(LEL)]が5.5eV以上であり、
(b)EHOMO−ELUMO>2.9eV、
(c)三重項エネルギーが2.3eV以上であり、
(d)ΔEst<0.5eV(ΔEstは、前記化合物の一重項エネルギーと三重項エネルギーとの差を示す)。
Y1〜Y4は、互いに同一又は異なって、それぞれ独立に、N又はC(R1)であり、この時、複数のR1は、同様な表示であっても、それぞれ同一又は異なっており、これらは隣り合う基と縮合環を形成することができ、
X2及びX3は、互いに同一又は異なって、それぞれ独立に、N又はC(R2)であり、この時、複数のR2は、同様な表示であっても、それぞれ同一又は異なっており、これらは隣り合う基と縮合環を形成することができ、
前記R1〜R2及びAr1〜Ar5は、互いに同一又は異なって、それぞれ独立に、水素、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
前記R1〜R2及びAr1〜Ar5における、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アルキルオキシ基、アリールオキシ基、アルキルシリル基、アリールシリル基、アルキルボロン基、アリールボロン基、ホスフィン基、ホスフィンオキサイド基、及びアリールアミン基は、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C40のアリール基、核原子数5〜40のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1種以上で置換されるか又は置換されていない。
X4は、X1と同じであり、この時、複数のAr1〜Ar5は、それぞれ同一又は異なっている。
前記R3における、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アルキルオキシ基、アリールオキシ基、アルキルシリル基、アリールシリル基、アルキルボロン基、アリールボロン基、ホスフィン基、ホスフィンオキサイド基、及びアリールアミン基は、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C40のアリール基、核原子数5〜40のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1種以上で置換されるか又は置換されていない。
R1〜R3は、それぞれ独立に、水素、置換或いは非置換のC1〜C40のアルキル基、置換或いは非置換のC6〜C40のアリール基、又は、置換或いは非置換の核原子数5〜40のヘテロアリール基であることが好ましい。
Y5〜Y14は、互いに同一又は異なって、それぞれ独立にN又はC(R3)であり、いずれもC(R3)であることが好ましい。なお、複数のR3は、同一又は異なっている。
Ar6〜Ar8は、互いに同一又は異なって、それぞれ独立に、水素、重水素、C6〜C40のアリール基、及び核原子数5〜40のヘテロアリール基からなる群から選択され(但し、Ar6〜Ar8がいずれも同一である場合を除く)、
R4〜R6は、互いに同一又は異なって、それぞれ独立に、水素、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
a乃至cは、それぞれ独立に0〜3の整数であり、
前記L1〜L3、R4〜R6及びAr6〜Ar8における、アリーレン基、ヘテロアリーレン基、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アルキルオキシ基、アリールオキシ基、アルキルシリル基、アリールシリル基、アルキルボロン基、アリールボロン基、ホスフィン基、ホスフィンオキサイド基、及びアリールアミン基は、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C40のアリール基、核原子数5〜40のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1種以上で置換されるか又は置換されていない。
ITO(Indium Tin Oxide)が1500Åの厚さで薄膜コーティングされたガラス基板を蒸留水で超音波洗浄を行った。蒸留水洗浄が終わると、イソプロピルアルコール、アセトン、メタノールなどの溶剤で超音波洗浄を行い、乾燥させた後、UV OZONE洗浄機(Power Sonic 405、Hwashin Tech社製)へ移送させた後、UVを用いて前記基板を5分間洗浄し、真空蒸着機へ基板を移送した。
寿命改善層を使用せずに電子輸送層を30nmで蒸着したこと以外は、前述の実施例1と同様にして素子を製造した。
LE−01に代えて、下記の構造を有するBCPを使用する以外は、前述の実施例1と同様にして素子を製造した。
前述の実施例1〜36及び比較例1、2で製造されたそれぞれの素子について、電流密度10mA/cm2での駆動電圧、電流効率、発光波長及び寿命(T97)を測定し、その結果を下記の表3に示した。
ITO(Indium Tin Oxide)が1500Åの厚さで薄膜コーティングされたガラス基板を蒸留水で超音波洗浄を行った。蒸留水洗浄が終わると、イソプロピルアルコール、アセトン、メタノールなどの溶剤で超音波洗浄を行い、乾燥させた後、UV OZONE洗浄機(Power Sonic 405、Hwashin Tech社製)へ移送させた後、UVを用いて前記基板を5分間洗浄し、真空蒸着機へ基板を移送した。
寿命改善層を使用せずに電子輸送層を30nmで蒸着したこと以外は、前述の実施例37と同様にして素子を製造した。
LE−02に代えて、前述の比較例2で使用されたBCPを使用する以外は、前述の実施例37と同様にして素子を製造した。
前述の実施例37〜51及び比較例3、4で製造されたそれぞれの素子について、電流密度10mA/cm2での駆動電圧、電流効率、発光波長及び寿命(T97)を測定し、その結果を下記の表5に示した。
200:負極
301:正孔注入層
302:正孔輸送層
303:発光層
304:寿命改善層
305:電子輸送層
306:電子注入層
Claims (1)
- 正極;
負極;及び
前記正極と負極との間に、正孔注入層、正孔輸送層、発光層、電子輸送層及び電子注入層からなる群から選択される有機物層が1層以上設けられており、
前記発光層と電子輸送層との間に、寿命改善層(Lifetime Enhancement Layer、LEL)をさらに含む有機電界発光素子であって、
前記寿命改善層は、下記の化合物LE−33及びLE−35からなる群から選択された双極性(bipolar)化合物を含み、
前記双極性化合物は、下記の(a)〜(d)の条件を満たすことを特徴とする有機電界発光素子:
(a)イオン化ポテンシャル[Ip(LEL)]が5.5eV以上であり、
(b)EHOMO−ELUMO>2.9eV、
(c)三重項エネルギーが2.3eV以上であり、
(d)ΔEst<0.5eV(ΔEstは、前記化合物の一重項エネルギーと三重項エネルギーとの差を示す)。
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Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101742359B1 (ko) * | 2013-12-27 | 2017-05-31 | 주식회사 두산 | 유기 전계 발광 소자 |
KR102163721B1 (ko) * | 2014-01-06 | 2020-10-08 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
CN105845831B (zh) * | 2015-01-30 | 2019-07-05 | 三星显示有限公司 | 有机发光装置 |
TWI690516B (zh) | 2015-10-27 | 2020-04-11 | 南韓商Lg化學股份有限公司 | 有機發光元件 |
KR20170075122A (ko) | 2015-12-22 | 2017-07-03 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102384293B1 (ko) | 2015-12-22 | 2022-04-08 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102615637B1 (ko) * | 2015-12-22 | 2023-12-20 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102579752B1 (ko) * | 2015-12-22 | 2023-09-19 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102579753B1 (ko) * | 2015-12-22 | 2023-09-19 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102615638B1 (ko) * | 2015-12-22 | 2023-12-20 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR20170075114A (ko) | 2015-12-22 | 2017-07-03 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR20170075118A (ko) * | 2015-12-22 | 2017-07-03 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102642199B1 (ko) | 2016-04-07 | 2024-03-05 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102611320B1 (ko) * | 2016-09-21 | 2023-12-07 | 솔루스첨단소재 주식회사 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
TWI666204B (zh) | 2016-10-18 | 2019-07-21 | 南韓商Lg化學股份有限公司 | 有機發光裝置 |
CN106816539B (zh) * | 2016-12-08 | 2018-10-12 | 瑞声科技(南京)有限公司 | 量子点发光二极管装置及其制造方法 |
KR20180072245A (ko) | 2016-12-21 | 2018-06-29 | 주식회사 두산 | 유기 전계 발광 소자 |
CN107068886B (zh) * | 2017-05-12 | 2019-01-25 | 京东方科技集团股份有限公司 | 有机电致发光器件及其制作方法、发光装置 |
KR101884130B1 (ko) | 2017-08-29 | 2018-07-31 | 주식회사 두산 | 유기 전계 발광 소자 |
CN108101893B (zh) * | 2018-01-30 | 2021-01-22 | 烟台九目化学股份有限公司 | 一种以咔唑和嘧啶为核心的有机化合物制备及其在oled上的应用 |
CN108550707B (zh) * | 2018-04-12 | 2022-11-08 | 京东方科技集团股份有限公司 | 量子点发光二极管、液晶显示设备 |
US11997862B2 (en) | 2018-12-27 | 2024-05-28 | Lg Display Co., Ltd. | Display device |
KR20210001188A (ko) * | 2019-06-27 | 2021-01-06 | 솔루스첨단소재 주식회사 | 유기 전계 발광 소자 |
KR20210008979A (ko) * | 2019-07-15 | 2021-01-26 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR20210021421A (ko) * | 2019-08-16 | 2021-02-26 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함한 장치 |
KR20210031584A (ko) * | 2019-09-11 | 2021-03-22 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함한 장치 |
KR20210086228A (ko) * | 2019-12-31 | 2021-07-08 | 엘지디스플레이 주식회사 | 유기전기소자, 이를 포함하는 표시패널 및 이를 포함하는 표시장치 |
KR20210136224A (ko) | 2020-05-06 | 2021-11-17 | 삼성디스플레이 주식회사 | 발광 소자 및 이를 포함하는 전자 장치 |
Family Cites Families (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100787423B1 (ko) | 2004-11-05 | 2007-12-26 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자 |
WO2006062144A1 (en) * | 2004-12-07 | 2006-06-15 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, and light-emitting element and light-emittng device using the same |
CN101203968B (zh) | 2005-04-21 | 2010-05-19 | 株式会社半导体能源研究所 | 发光元件、发光器件和电子设备 |
US9051344B2 (en) * | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
KR20140141680A (ko) | 2006-12-20 | 2014-12-10 | 톰슨 라이센싱 | 바이폴라 재료로 만든 장벽층을 구비한 유기 발광 다이오드 |
US8207526B2 (en) * | 2007-03-23 | 2012-06-26 | Idemitsu Kosan Co., Ltd. | Organic EL device |
US8034465B2 (en) * | 2007-06-20 | 2011-10-11 | Global Oled Technology Llc | Phosphorescent oled having double exciton-blocking layers |
JPWO2010084729A1 (ja) * | 2009-01-22 | 2012-07-12 | 保土谷化学工業株式会社 | ピリジル基が連結したトリアゾール環構造を有する化合物および有機エレクトロルミネッセンス素子 |
TWI469968B (zh) * | 2009-03-31 | 2015-01-21 | Semiconductor Energy Lab | 雜環化合物及使用該雜環化合物之發光元件、發光裝置、照明裝置和電子設備 |
US9741955B2 (en) | 2009-05-29 | 2017-08-22 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, and method for manufacturing the same |
JP5238889B2 (ja) * | 2010-01-15 | 2013-07-17 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
TW201232864A (en) * | 2010-11-22 | 2012-08-01 | Idemitsu Kosan Co | Organic electroluminescence device |
KR102126087B1 (ko) | 2011-10-11 | 2020-06-23 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 기기, 조명 장치, 및 피렌계 화합물 |
KR101488565B1 (ko) * | 2011-12-07 | 2015-02-03 | 주식회사 두산 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
WO2013085339A2 (ko) * | 2011-12-07 | 2013-06-13 | 주식회사 두산 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
WO2014023388A1 (de) | 2012-08-10 | 2014-02-13 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
US20160254060A1 (en) * | 2013-03-15 | 2016-09-01 | Taqua Wbh, Llc | High Speed And Low Power Sense Amplifier |
EP2972689A4 (en) * | 2013-03-15 | 2016-11-23 | Forbes Holten 3Rd Norris | SPEECH OPTIMIZING MICROCLAVIER METHOD AND APPARATUS |
KR101667099B1 (ko) * | 2013-03-29 | 2016-10-17 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기 발광 소자 |
KR20140135525A (ko) * | 2013-05-16 | 2014-11-26 | 제일모직주식회사 | 유기 광전자 소자용 발광 재료, 유기 광전자 소자 및 표시 장치 |
KR101618683B1 (ko) * | 2013-05-16 | 2016-05-09 | 제일모직 주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
KR20140135532A (ko) * | 2013-05-16 | 2014-11-26 | 제일모직주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
KR101641404B1 (ko) * | 2013-12-17 | 2016-07-20 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101742359B1 (ko) * | 2013-12-27 | 2017-05-31 | 주식회사 두산 | 유기 전계 발광 소자 |
CN104795503B (zh) * | 2014-01-16 | 2018-07-20 | 三星显示有限公司 | 有机发光装置 |
KR102221106B1 (ko) * | 2014-01-17 | 2021-03-02 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR101729373B1 (ko) * | 2014-03-04 | 2017-04-21 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101998435B1 (ko) * | 2014-06-09 | 2019-07-09 | 주식회사 두산 | 유기 전계 발광 소자 |
KR101708097B1 (ko) * | 2014-10-22 | 2017-02-17 | 주식회사 두산 | 유기 전계 발광 소자 |
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