JP2006510230A - 有機エレクトロルミネッセンス組成物 - Google Patents
有機エレクトロルミネッセンス組成物 Download PDFInfo
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- JP2006510230A JP2006510230A JP2004571703A JP2004571703A JP2006510230A JP 2006510230 A JP2006510230 A JP 2006510230A JP 2004571703 A JP2004571703 A JP 2004571703A JP 2004571703 A JP2004571703 A JP 2004571703A JP 2006510230 A JP2006510230 A JP 2006510230A
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- Japan
- Prior art keywords
- group
- independently selected
- composition
- tertiary aromatic
- phenyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 134
- 239000000463 material Substances 0.000 claims abstract description 104
- 150000003513 tertiary aromatic amines Chemical class 0.000 claims abstract description 57
- 239000011159 matrix material Substances 0.000 claims abstract description 40
- 239000002019 doping agent Substances 0.000 claims abstract description 32
- 230000002285 radioactive effect Effects 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 125000001424 substituent group Chemical group 0.000 claims abstract description 26
- 125000000962 organic group Chemical group 0.000 claims abstract description 23
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000004305 biphenyl Substances 0.000 claims abstract description 10
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 10
- 239000000758 substrate Substances 0.000 claims description 86
- -1 (5- (p-octyloxy) Phenyl) -1,3,4-oxadiazol-2-yl Chemical group 0.000 claims description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 229920000642 polymer Polymers 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 230000005525 hole transport Effects 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000004986 diarylamino group Chemical group 0.000 claims description 12
- 239000004642 Polyimide Substances 0.000 claims description 11
- 229920001721 polyimide Polymers 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical group 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- KTBCNCJNKCTBRL-UHFFFAOYSA-N 2-[3,5-bis[5-(4-octoxyphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-5-(4-octoxyphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NN=C(C=2C=C(C=C(C=2)C=2OC(=NN=2)C=2C=CC(OCCCCCCCC)=CC=2)C=2OC(=NN=2)C=2C=CC(OCCCCCCCC)=CC=2)O1 KTBCNCJNKCTBRL-UHFFFAOYSA-N 0.000 claims description 4
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000010410 layer Substances 0.000 description 154
- 230000000052 comparative effect Effects 0.000 description 55
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 31
- 239000002120 nanofilm Substances 0.000 description 30
- 238000012546 transfer Methods 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 150000003384 small molecules Chemical class 0.000 description 28
- 239000004743 Polypropylene Substances 0.000 description 26
- 238000003384 imaging method Methods 0.000 description 26
- 229920001155 polypropylene Polymers 0.000 description 26
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 25
- 230000005855 radiation Effects 0.000 description 25
- 238000000576 coating method Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000010408 film Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229910052741 iridium Inorganic materials 0.000 description 15
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 14
- 239000011230 binding agent Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 12
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011229 interlayer Substances 0.000 description 9
- 150000002739 metals Chemical class 0.000 description 9
- 229920002223 polystyrene Polymers 0.000 description 9
- 239000006100 radiation absorber Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 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 8
- 239000000049 pigment Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 101100406338 Mycoplasma capricolum subsp. capricolum (strain California kid / ATCC 27343 / NCTC 10154) pdhC gene Proteins 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 101100462087 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) LAT1 gene Proteins 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920005992 thermoplastic resin Polymers 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000013522 chelant Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 5
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- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 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 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 5
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- IIRGMTDTYZCUFM-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-5-(4-octoxyphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NN=C(C=2C(=CC=C(Cl)C=2)Cl)O1 IIRGMTDTYZCUFM-UHFFFAOYSA-N 0.000 description 4
- BGGDZDRRHQTSPV-UHFFFAOYSA-N 4-ethenyl-n,n-diphenylaniline Chemical compound C1=CC(C=C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BGGDZDRRHQTSPV-UHFFFAOYSA-N 0.000 description 4
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- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 4
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- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
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- 238000004821 distillation Methods 0.000 description 4
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
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- MUNFOTHAFHGRIM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-oxadiazole Chemical compound C1=CC=C2C(C3=NN=C(O3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MUNFOTHAFHGRIM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QQWPLVSLXJSGMO-UHFFFAOYSA-N 4-octoxybenzohydrazide Chemical compound CCCCCCCCOC1=CC=C(C(=O)NN)C=C1 QQWPLVSLXJSGMO-UHFFFAOYSA-N 0.000 description 3
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 230000008901 benefit Effects 0.000 description 3
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 3
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- 238000005401 electroluminescence Methods 0.000 description 3
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- 238000006862 quantum yield reaction Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000007651 thermal printing Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- WSXWMOYTXDIAGA-UHFFFAOYSA-N zinc 2-(5-phenyl-1,3,4-oxadiazol-2-yl)phenol Chemical compound [Zn+2].OC1=CC=CC=C1C1=NN=C(C=2C=CC=CC=2)O1.OC1=CC=CC=C1C1=NN=C(C=2C=CC=CC=2)O1 WSXWMOYTXDIAGA-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/114—Poly-phenylenevinylene; Derivatives thereof
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
- H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/254,237 US20040062947A1 (en) | 2002-09-25 | 2002-09-25 | Organic electroluminescent compositions |
| PCT/US2003/029007 WO2004099338A2 (en) | 2002-09-25 | 2003-09-15 | Organic electroluminescent compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006510230A true JP2006510230A (ja) | 2006-03-23 |
| JP2006510230A5 JP2006510230A5 (enExample) | 2006-11-09 |
Family
ID=32029033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004571703A Withdrawn JP2006510230A (ja) | 2002-09-25 | 2003-09-15 | 有機エレクトロルミネッセンス組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20040062947A1 (enExample) |
| EP (1) | EP1554360A2 (enExample) |
| JP (1) | JP2006510230A (enExample) |
| KR (1) | KR20050053687A (enExample) |
| CN (1) | CN100357388C (enExample) |
| AU (1) | AU2003304084A1 (enExample) |
| WO (1) | WO2004099338A2 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006013482A (ja) * | 2004-06-25 | 2006-01-12 | Samsung Sdi Co Ltd | 有機電界発光素子 |
| JP2007515788A (ja) * | 2003-12-05 | 2007-06-14 | イーストマン コダック カンパニー | 添加剤を含む有機エレクトロルミネセンスデバイス |
| JP2010141008A (ja) * | 2008-12-10 | 2010-06-24 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子材料、表示装置及び照明装置 |
| JP2021040157A (ja) * | 2011-03-23 | 2021-03-11 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、照明装置及び電子機器 |
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| GB2426866C (en) * | 2002-09-13 | 2007-03-07 | Dainippon Printing Co Ltd | A display. |
| JP3900125B2 (ja) * | 2002-11-26 | 2007-04-04 | セイコーエプソン株式会社 | 有機エレクトロルミネッセンス装置の製造方法 |
| US20040191564A1 (en) * | 2002-12-17 | 2004-09-30 | Samsung Sdi Co., Ltd. | Donor film for low molecular weight full color organic electroluminescent device using laser induced thermal imaging method and method for fabricating low molecular weight full color organic electroluminescent device using the film |
| JP4401665B2 (ja) | 2003-03-20 | 2010-01-20 | 株式会社半導体エネルギー研究所 | 電界発光素子 |
| US20060186791A1 (en) * | 2003-05-29 | 2006-08-24 | Osamu Yoshitake | Organic electroluminescent element |
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| DE10333232A1 (de) * | 2003-07-21 | 2007-10-11 | Merck Patent Gmbh | Organisches Elektrolumineszenzelement |
| US7625501B2 (en) | 2004-05-18 | 2009-12-01 | Ifire Ip Corporation | Color-converting photoluminescent film |
| US7315042B2 (en) * | 2004-11-18 | 2008-01-01 | 3M Innovative Properties Company | Semiconductors containing trans-1,2-bis(acenyl)ethylene compounds |
| US20060105199A1 (en) * | 2004-11-18 | 2006-05-18 | 3M Innovative Properties Company | Electroluminescent devices containing trans-1,2-bis(acenyl)ethylene compounds |
| KR100708655B1 (ko) | 2004-11-27 | 2007-04-18 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자 |
| US7566506B2 (en) * | 2005-01-19 | 2009-07-28 | Jen-Chieh Wang | Magnetic body |
| KR100787428B1 (ko) * | 2005-03-05 | 2007-12-26 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자 |
| JP2007095759A (ja) * | 2005-09-27 | 2007-04-12 | Hitachi Displays Ltd | 有機ｅｌ表示装置 |
| WO2009055532A1 (en) * | 2007-10-23 | 2009-04-30 | E. I. Du Pont De Nemours And Company | Ternary emissive layers for luminescent applications |
| US20090142556A1 (en) * | 2007-11-29 | 2009-06-04 | E. I. Du Pont De Nemours And Company | Process for forming an organic electronic device including an organic device layer |
| US8040048B2 (en) * | 2007-12-12 | 2011-10-18 | Lang Charles D | Process for forming an organic electronic device including an organic device layer |
| DE102008050841B4 (de) * | 2008-10-08 | 2019-08-01 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
| KR20120102575A (ko) * | 2009-06-22 | 2012-09-18 | 메르크 파텐트 게엠베하 | 도전성 조성물 |
| DE102009030848A1 (de) * | 2009-06-26 | 2011-02-03 | Merck Patent Gmbh | Polymere enthaltend Struktureinheiten, die Alkylalkoxygruppen aufweisen, Blends enthaltend diese Polymere sowie optoelektronische Vorrichtungen enthaltend diese Polymere und Blends |
| KR101596918B1 (ko) * | 2009-12-11 | 2016-02-23 | 고려대학교 산학협력단 | 저가형 염료감응 태양전지용 정공수송물질 함유한 폴리에틸렌옥사이드계 고체 전해질의 제조 |
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| JP2002240437A (ja) * | 2001-02-19 | 2002-08-28 | Sharp Corp | 薄膜形成用ドナーシートの製造方法、薄膜形成用ドナーシート及び有機エレクトロルミネッセンス素子 |
| EP2276084A1 (en) * | 2001-03-14 | 2011-01-19 | The Trustees of Princeton University | Materials and devices for blue phosphorescence based organic light emitting diodes |
| US6903505B2 (en) * | 2001-12-17 | 2005-06-07 | General Electric Company | Light-emitting device with organic electroluminescent material and photoluminescent materials |
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-
2002
- 2002-09-25 US US10/254,237 patent/US20040062947A1/en not_active Abandoned
-
2003
- 2003-09-15 CN CNB038224275A patent/CN100357388C/zh not_active Expired - Fee Related
- 2003-09-15 JP JP2004571703A patent/JP2006510230A/ja not_active Withdrawn
- 2003-09-15 KR KR1020057005030A patent/KR20050053687A/ko not_active Withdrawn
- 2003-09-15 EP EP03816923A patent/EP1554360A2/en not_active Withdrawn
- 2003-09-15 AU AU2003304084A patent/AU2003304084A1/en not_active Abandoned
- 2003-09-15 WO PCT/US2003/029007 patent/WO2004099338A2/en not_active Ceased
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007515788A (ja) * | 2003-12-05 | 2007-06-14 | イーストマン コダック カンパニー | 添加剤を含む有機エレクトロルミネセンスデバイス |
| JP2011216893A (ja) * | 2003-12-05 | 2011-10-27 | Global Oled Technology Llc | 添加剤を含む有機エレクトロルミネセンスデバイス |
| JP2006013482A (ja) * | 2004-06-25 | 2006-01-12 | Samsung Sdi Co Ltd | 有機電界発光素子 |
| JP2010141008A (ja) * | 2008-12-10 | 2010-06-24 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子材料、表示装置及び照明装置 |
| JP2021040157A (ja) * | 2011-03-23 | 2021-03-11 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、照明装置及び電子機器 |
| JP7021332B2 (ja) | 2011-03-23 | 2022-02-16 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、照明装置及び電子機器 |
| JP2022058859A (ja) * | 2011-03-23 | 2022-04-12 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、照明装置および電子機器 |
| US11871592B2 (en) | 2011-03-23 | 2024-01-09 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1554360A2 (en) | 2005-07-20 |
| AU2003304084A1 (en) | 2004-11-26 |
| US20040062947A1 (en) | 2004-04-01 |
| CN100357388C (zh) | 2007-12-26 |
| AU2003304084A8 (en) | 2004-11-26 |
| WO2004099338A2 (en) | 2004-11-18 |
| WO2004099338A3 (en) | 2005-01-06 |
| CN1681903A (zh) | 2005-10-12 |
| KR20050053687A (ko) | 2005-06-08 |
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