CN101582487B - 有机电致发光器件和显示装置 - Google Patents
有机电致发光器件和显示装置 Download PDFInfo
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- CN101582487B CN101582487B CN2009101410727A CN200910141072A CN101582487B CN 101582487 B CN101582487 B CN 101582487B CN 2009101410727 A CN2009101410727 A CN 2009101410727A CN 200910141072 A CN200910141072 A CN 200910141072A CN 101582487 B CN101582487 B CN 101582487B
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- electroluminescence device
- organic electroluminescence
- naphthonaphthalene
- compound
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- 239000010410 layer Substances 0.000 claims abstract description 305
- -1 naphthacene compound Chemical class 0.000 claims abstract description 253
- 239000012044 organic layer Substances 0.000 claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 35
- 238000005401 electroluminescence Methods 0.000 claims description 116
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 51
- 239000000758 substrate Substances 0.000 claims description 40
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004185 ester group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 8
- 125000005577 anthracene group Chemical group 0.000 claims description 5
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 20
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
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- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 2
- KMQPLEYEXDZOJF-UHFFFAOYSA-N 1-naphthalen-2-ylanthracene Chemical compound C1=CC=C2C=C3C(C4=CC5=CC=CC=C5C=C4)=CC=CC3=CC2=C1 KMQPLEYEXDZOJF-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- YTUILTQRCVAYNB-UHFFFAOYSA-N 101686-49-1 Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=C2C4=CC=CC=C4C4=CC=C3C1=C42 YTUILTQRCVAYNB-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 2
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- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
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- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- XEXYATIPBLUGSF-UHFFFAOYSA-N phenanthro[9,10-b]pyridine-2,3,4,5,6,7-hexacarbonitrile Chemical group N1=C(C#N)C(C#N)=C(C#N)C2=C(C(C#N)=C(C(C#N)=C3)C#N)C3=C(C=CC=C3)C3=C21 XEXYATIPBLUGSF-UHFFFAOYSA-N 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
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- 230000006641 stabilisation Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
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- C—CHEMISTRY; METALLURGY
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- 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
Abstract
Description
萘并萘化合物层14d(红荧烯)的厚度 | 电压(V) | 颜色坐标(x,y) | 亮度的半衰期(hr) | |
实施例1 | 1nm | 8.0 | (0.13,0.10) | 750 |
实施例2 | 3nm | 8.0 | (0.13,0.10) | 720 |
实施例3 | 5nm | 8.1 | (0.13,0.10) | 680 |
实施例4 | 10nm | 8.2 | (0.13,0.10) | 610 |
对比例1 | 无(Alq3 28nm) | 8.1 | (0.13,0.10) | 320 |
对比例2 | 28nm | 8.8 | (0.13,0.16) | 80 |
对比例3 | 15nm | 8.4 | (0.13,0.14) | 280 |
萘并萘化合物 | 萘并萘化合物层14d的厚度 | 电压(V) | 颜色坐标(x,y) | 亮度半衰期(hr) | |
实施例5 | 105 | 1nm | 7.5 | (0.24,0.67) | 480 |
实施例6 | 105 | 5nm | 7.6 | (0.24,0.67) | 430 |
实施例7 | 106 | 1nm | 7.6 | (0.24,0.67) | 360 |
实施例8 | 106 | 5nm | 7.7 | (0.24,0.67) | 320 |
实施例9 | 107 | 1nm | 7.5 | (0.24,0.67) | 320 |
实施例10 | 107 | 5nm | 7.7 | (0.24,0.67) | 300 |
对比例4 | 无 | 无(Alq3 40nm) | 7.5 | (0.24,0.67) | 240 |
萘并萘化合物 | 萘并萘化合物层14d的厚度 | 发光效率(cd/A) | 颜色坐标(x,y) | 亮度半衰期(hr) | |
实施例11 | 105 | 1nm | 17.7 | (0.24,0.67) | 1340 |
实施例12 | 105 | 3nm | 20.0 | (0.24,0.67) | 1380 |
实施例13 | 105 | 5nm | 20.6 | (0.24,0.67) | 1410 |
实施例14 | 105 | 10nm | 18.9 | (0.21,0.67) | 1380 |
对比例5 | 无 | 无(Alq3 40nm) | 18.9 | (0.24,0.67) | 340 |
Claims (13)
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JP2008129592A JP2009277986A (ja) | 2008-05-16 | 2008-05-16 | 有機電界発光素子および表示装置 |
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JP (1) | JP2009277986A (zh) |
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KR20120112520A (ko) * | 2009-12-09 | 2012-10-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전자 응용을 위한 화합물의 배합물의 일부로서의 중수소화된 화합물 |
US9083000B2 (en) * | 2011-04-29 | 2015-07-14 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, and lighting device |
JP6128117B2 (ja) * | 2012-04-24 | 2017-05-17 | コニカミノルタ株式会社 | 透明電極の製造方法 |
JP2014007301A (ja) * | 2012-06-25 | 2014-01-16 | Seiko Epson Corp | 発光素子、発光装置、表示装置および電子機器 |
CN103382181B (zh) | 2013-07-09 | 2015-05-20 | 京东方科技集团股份有限公司 | 多芳基取代嘧啶衍生物及其制备方法、有机电致发光器件、有机电致发光显示装置 |
JP6365353B2 (ja) * | 2015-03-05 | 2018-08-01 | 株式会社デンソー | Ofdm受信装置 |
US10270055B2 (en) * | 2017-03-16 | 2019-04-23 | Wuhan China Star Optoelectronics Technology Co., Ltd. | Flexible display device and method of manufacturing the same |
US11903232B2 (en) | 2019-03-07 | 2024-02-13 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting device comprising charge-generation layer between light-emitting units |
CN111900257A (zh) * | 2020-08-12 | 2020-11-06 | 京东方科技集团股份有限公司 | 一种发光器件及其制作方法、显示装置 |
TWI776654B (zh) * | 2021-08-24 | 2022-09-01 | 友達光電股份有限公司 | 顯示裝置及其製造方法 |
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US6696177B1 (en) | 2000-08-30 | 2004-02-24 | Eastman Kodak Company | White organic electroluminescent devices with improved stability and efficiency |
US6661023B2 (en) * | 2002-02-28 | 2003-12-09 | Eastman Kodak Company | Organic element for electroluminescent devices |
US6720092B2 (en) | 2002-07-08 | 2004-04-13 | Eastman Kodak Company | White organic light-emitting devices using rubrene layer |
US20040058193A1 (en) | 2002-09-16 | 2004-03-25 | Eastman Kodak Company | White organic light-emitting devices with improved performance |
US8012602B2 (en) * | 2002-10-30 | 2011-09-06 | Basf Se | Electroluminescent device |
US6967062B2 (en) * | 2003-03-19 | 2005-11-22 | Eastman Kodak Company | White light-emitting OLED device having a blue light-emitting layer doped with an electron-transporting or a hole-transporting material or both |
US6875524B2 (en) | 2003-08-20 | 2005-04-05 | Eastman Kodak Company | White light-emitting device with improved doping |
KR20080103056A (ko) * | 2006-02-23 | 2008-11-26 | 이데미쓰 고산 가부시키가이샤 | 유기 전계 발광 소자용 재료, 그의 제조 방법 및 유기 전계발광 소자 |
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