KR100809132B1 - 유기 전자발광 소자 및 유기 발광 매체 - Google Patents
유기 전자발광 소자 및 유기 발광 매체 Download PDFInfo
- Publication number
- KR100809132B1 KR100809132B1 KR1020017006271A KR20017006271A KR100809132B1 KR 100809132 B1 KR100809132 B1 KR 100809132B1 KR 1020017006271 A KR1020017006271 A KR 1020017006271A KR 20017006271 A KR20017006271 A KR 20017006271A KR 100809132 B1 KR100809132 B1 KR 100809132B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- carbon atoms
- substituted
- light emitting
- formula
- Prior art date
Links
- 238000005401 electroluminescence Methods 0.000 title 1
- 150000001412 amines Chemical class 0.000 claims abstract description 31
- 150000001454 anthracenes Chemical class 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 30
- 125000005504 styryl group Chemical group 0.000 claims description 27
- -1 monophenylanthryl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 239000002019 doping agent Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005577 anthracene group Chemical group 0.000 claims description 6
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 150000004770 chalcogenides Chemical class 0.000 claims description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 2
- OURODNXVJUWPMZ-UHFFFAOYSA-N 1,2-diphenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 OURODNXVJUWPMZ-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- FMKFBRKHHLWKDB-UHFFFAOYSA-N rubicene Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=C1C=CC=C2C4=CC=CC=C4C3=C21 FMKFBRKHHLWKDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 239000010410 layer Substances 0.000 description 118
- 238000002347 injection Methods 0.000 description 48
- 239000007924 injection Substances 0.000 description 48
- 239000000463 material Substances 0.000 description 19
- 239000000758 substrate Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000001771 vacuum deposition Methods 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 7
- 238000000151 deposition Methods 0.000 description 6
- 239000007772 electrode material Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 229960003540 oxyquinoline Drugs 0.000 description 5
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101100037618 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ant-1 gene Proteins 0.000 description 3
- 229910052761 rare earth metal Inorganic materials 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910018068 Li 2 O Inorganic materials 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000005567 fluorenylene group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 125000005548 pyrenylene group Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 125000006836 terphenylene group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000005556 thienylene group Chemical group 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 C(c1ccccc1)=Cc(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccc(*=Cc2ccccc2)cc1 Chemical compound C(c1ccccc1)=Cc(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccc(*=Cc2ccccc2)cc1 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910007541 Zn O Inorganic materials 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005024 alkenyl aryl group Chemical group 0.000 description 1
- 239000005354 aluminosilicate glass Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 229930192474 thiophene Natural products 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- H10K50/80—Constructional details
- H10K50/805—Electrodes
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
-
- 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
-
- 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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Abstract
Description
Claims (16)
- (A) 아민 함유 모노스티릴 유도체, 아민 함유 디스티릴 유도체, 아민 함유 트리스티릴 유도체 및 아민 함유 테트라스티릴 유도체 중에서 선택된 1종 이상의 화합물, 및 (B) 하기 화학식 I의 안트라센 유도체 및 하기 화학식 II의 안트라센 유도체 중에서 선택된 1종 이상의 화합물을 포함함을 특징으로 하는 유기 발광 매체층:화학식 IA1-L-A2화학식 IIA3-An-A4상기 식들에서,A1 및 A2는 각각 치환되거나 치환되지 않은 모노페닐안트릴 기 또는 치환되거나 치환되지 않은 디페닐안트릴 기이고, 서로 동일하거나 상이할 수 있으며;L은 단일 결합이거나 또는 2가의 연결기이고;An은 치환되거나 치환되지 않은 2가의 안트라센 잔기이고;A3 및 A4는 각각 치환되거나 치환되지 않은 1가의 축합된 방향족환 기 또는 치환되거나 치환되지 않은 탄소수 12 이상의 비축합환계 아릴 기이며, 서로 동일하거나 상이할 수 있고;An, A3 및 A4중 어느 하나가 치환기를 갖는 경우, 이 치환기는 탄소수 1 내지 6의 알킬 기, 탄소수 3 내지 6의 사이클로알킬 기, 탄소수 1 내지 6의 알콕시 기, 탄소수 5 내지 18의 아릴옥시 기, 탄소수 7 내지 18의 아르알킬옥시 기, 탄소수 5 내지 16의 아릴 기로 치환된 아미노 기, 니트로 기, 시아노 기, 탄소수 1 내지 6의 에스테르 기, 및 할로겐 원자로 이루어진 군으로부터 선택된다.
- 제 1 항에 있어서,(B) 성분의 화학식 I의 안트라센 유도체가, 하기 화학식 Ia의 안트라센 유도체 또는 하기 화학식 Ib의 안트라센 유도체인 유기 발광 매체층:화학식 Ia화학식 Ib상기 식들에서,R1 내지 R10은 각각 독립적으로 수소 원자, 알킬 기, 사이클로알킬 기, 치환될 수 있는 아릴 기, 알콕시 기, 아릴옥시 기, 알킬아미노 기, 아릴아미노 기 또는 치환될 수 있는 헤테로환 기이고;a 및 b는 각각 1 내지 5의 정수이고, 이들이 2 이상의 정수인 경우, 다수의 R1, 또는 다수의 R2는 각각 동일하거나 상이할 수 있으며, 또한 다수의 R1, 또는 다수의 R2가 함께 결합하여 환을 형성할 수 있고;R3 및 R4, 또는 R5 및 R6, 또는 R7 및 R8, 또는 R9 및 R10이 함께 결합하여 환을 형성할 수 있으며;L1은 단일 결합이거나, 또는 -O-, -S-, -N(R)- 또는 아릴렌 기이고, 이때 R은 알킬 기 또는 치환될 수 있는 아릴 기이며;R11 내지 R20은 각각 독립적으로 수소 원자, 알킬 기, 사이클로알킬 기, 아릴 기, 알콕시 기, 아릴옥시 기, 알킬아미노 기, 아릴아미노 기 또는 치환될 수 있는 헤테로환 기이고;c, d, e 및 f는 각각 1 내지 5의 정수이고, 이들이 2 이상의 정수인 경우, 다수의 R11, 다수의 R12, 다수의 R16 또는 다수의 R17은 각각 동일하거나 상이할 수 있으며, 또한 다수의 R11, 또는 다수의 R12, 또는 다수의 R16, 또는 다수의 R17이 함께 결합하여 환을 형성할 수 있고;R13 및 R14, 또는 R18 및 R19가 함께 결합하여 환을 형성할 수 있으며;L2는 단일 결합이거나, 또는 -O-, -S-, -N(R)- 또는 아릴렌 기이고, 이때 R은 알킬 기 또는 치환될 수 있는 아릴 기이다.
- 제 1 항에 있어서,(B) 성분의 화학식 II의 안트라센 유도체가 하기 화학식 IIa의 안트라센 유도체인 유기 발광 매체층:화학식 IIaAr1-An-Ar2상기 식에서,An은 치환되거나 치환되지 않은 2가의 안트라센 잔기이고;Ar1 및 Ar2는 각각 독립적으로 치환되거나 치환되지 않은 나프탈렌, 페난트렌, 안트라센, 피렌, 페릴렌, 코로넨, 크리센, 피센, 플루오렌, 터페닐, 디페닐안트라센, 비페닐, N-알킬카바졸, N-아릴카바졸, 트리페닐렌, 루비센, 벤조안트라센 또는 디벤조안트라센의 1가 잔기이고,An, Ar1 및 Ar2중 어느 하나가 치환기를 갖는 경우, 이 치환기는 탄소수 1 내지 6의 알킬 기, 탄소수 3 내지 6의 사이클로알킬 기, 탄소수 1 내지 6의 알콕시 기, 탄소수 5 내지 18의 아릴옥시 기, 탄소수 7 내지 18의 아르알킬옥시 기, 탄소수 5 내지 16의 아릴 기로 치환된 아미노 기, 니트로 기, 시아노 기, 탄소수 1 내지 6의 에스테르 기, 및 할로겐 원자로 이루어진 군으로부터 선택된다.
- 제 1 항에 있어서,(A) 성분이, 하기 화학식 III의 아민 함유 스티릴 유도체 및 하기 화학식 IV의 아민 함유 스티릴 유도체 중에서 선택된 1종 이상인 유기 발광 매체층:화학식 III화학식 IV상기 식들에서,Ar3, Ar4 및 Ar5는 각각 독립적으로 치환되거나 치환되지 않은 탄소수 6 내지 40의 방향족 기이고, 이들 기 중 1개 이상은 스티릴 기를 포함하며;g는 1 내지 4의 정수이나, 스티릴 기의 총수는 1 내지 4이며;Ar6, Ar7, Ar9, Ar11 및 Ar12는 각각 독립적으로 치환되거나 치환되지 않은 탄소수 6 내지 40의 1가 방향족 기이고,Ar8 및 Ar10은 각각 독립적으로 치환되거나 치환되지 않은 탄소수 6 내지 40의 2가 방향족 기이고,Ar6 내지 Ar12 중에서 1개 이상은 스티릴 기 또는 스티릴렌 기를 포함하며;h 및 k는 각각 0 내지 2의 정수이고;i 및 j는 각각 1 또는 2의 정수이나, 스티릴 기 및 스티릴렌 기의 총수는 1 내지 4이다.
- 삭제
- 삭제
- 삭제
- 삭제
- 삭제
- 삭제
- 삭제
- 한 쌍의 전극; 및 이들 전극 사이에 배치된 제 1 항 내지 제 4 항 중 어느 한 항에 따른 유기 발광 매체층을 포함하는 유기 전자발광 소자.
- 제 12 항에 있어서,유기 발광 매체층이 (A) 성분과 (B) 성분을 2:98 내지 9:91의 중량비로 포함하는 유기 전자발광 소자.
- 제 12 항에 있어서,한 쌍의 전극중 하나 이상의 표면에 칼코제나이드(chalcogenide)층, 할로겐화 금속층 또는 금속 산화물층이 배치된 유기 전자발광 소자.
- 제 12 항에 있어서,한 쌍의 전극중 하나 이상의 표면에, 환원성 도판트(dopant)와 유기물의 혼합 영역, 또는 산화성 도판트와 유기물의 혼합 영역이 배치됨을 특징으로 하는 유기 전자발광 소자.
- 제 12 항에 있어서,유기 발광 매체층이 10 내지 400nm 두께의 것인 유기 전자발광 소자.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP99-267460 | 1999-09-21 | ||
JP26746099 | 1999-09-21 |
Related Child Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020057017620A Division KR100738762B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
KR1020077019127A Division KR100790663B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
KR1020077006875A Division KR100799799B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20010080488A KR20010080488A (ko) | 2001-08-22 |
KR100809132B1 true KR100809132B1 (ko) | 2008-02-29 |
Family
ID=17445157
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020017006271A KR100809132B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
KR1020077019127A KR100790663B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
KR1020057017620A KR100738762B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
KR1020077006875A KR100799799B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020077019127A KR100790663B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
KR1020057017620A KR100738762B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
KR1020077006875A KR100799799B1 (ko) | 1999-09-21 | 2000-09-20 | 유기 전자발광 소자 및 유기 발광 매체 |
Country Status (9)
Country | Link |
---|---|
US (1) | US6534199B1 (ko) |
EP (2) | EP1775783A3 (ko) |
JP (1) | JP5073899B2 (ko) |
KR (4) | KR100809132B1 (ko) |
CN (1) | CN1208422C (ko) |
AT (1) | ATE360892T1 (ko) |
DE (1) | DE60034560T2 (ko) |
TW (1) | TW474113B (ko) |
WO (1) | WO2001021729A1 (ko) |
Families Citing this family (155)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2270117A3 (en) * | 1998-12-28 | 2011-04-27 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
KR100721656B1 (ko) * | 2005-11-01 | 2007-05-23 | 주식회사 엘지화학 | 유기 전기 소자 |
WO2002014244A1 (fr) * | 2000-08-10 | 2002-02-21 | Mitsui Chemicals, Inc. | Compose d'hydrocarbure, materiau pour element organique electroluminescent et element organique electroluminescent |
EP1314715A4 (en) * | 2000-09-01 | 2005-03-02 | Idemitsu Kosan Co | STYRY COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICES |
JP4220669B2 (ja) * | 2000-12-26 | 2009-02-04 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
JP4046267B2 (ja) * | 2002-03-26 | 2008-02-13 | 株式会社半導体エネルギー研究所 | 表示装置 |
JP4646494B2 (ja) * | 2002-04-11 | 2011-03-09 | 出光興産株式会社 | 新規含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
JP4161262B2 (ja) * | 2002-06-26 | 2008-10-08 | ソニー株式会社 | 有機電界発光素子、及びそれを用いた発光又は表示装置 |
KR101018547B1 (ko) * | 2002-07-19 | 2011-03-03 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자 및 유기 발광 매체 |
JP4025137B2 (ja) * | 2002-08-02 | 2007-12-19 | 出光興産株式会社 | アントラセン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
DE60330696D1 (de) * | 2002-08-23 | 2010-02-04 | Idemitsu Kosan Co | Organische elektrolumineszenzvorrichtung und anthracenderivat |
CN100518424C (zh) * | 2002-11-18 | 2009-07-22 | 出光兴产株式会社 | 有机电致发光元件 |
JP4287198B2 (ja) * | 2002-11-18 | 2009-07-01 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
EP1437395B2 (en) | 2002-12-24 | 2015-08-26 | LG Display Co., Ltd. | Organic electroluminescent device |
KR100624407B1 (ko) * | 2003-01-02 | 2006-09-18 | 삼성에스디아이 주식회사 | 디페닐안트라센 유도체 및 이를 채용한 유기 전계 발광 소자 |
KR101064077B1 (ko) | 2003-01-10 | 2011-09-08 | 이데미쓰 고산 가부시키가이샤 | 질소-함유 헤테로환 유도체 및 이를 이용한 유기 전기발광소자 |
WO2004074399A1 (ja) * | 2003-02-20 | 2004-09-02 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
US7651788B2 (en) * | 2003-03-05 | 2010-01-26 | Lg Display Co., Ltd. | Organic electroluminescent device |
JP4624653B2 (ja) * | 2003-05-20 | 2011-02-02 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
JP3840235B2 (ja) * | 2003-06-27 | 2006-11-01 | キヤノン株式会社 | 有機発光素子 |
US20050079383A1 (en) * | 2003-10-14 | 2005-04-14 | Lightronik Technology Inc. | Organic light emitting medium containing 9, 9' -bianthry-10,10' -phenanthrcene and device containing the medium |
KR20100052573A (ko) | 2003-12-19 | 2010-05-19 | 이데미쓰 고산 가부시키가이샤 | 유기 전기 발광 소자용 발광 재료, 이를 이용한 유기 전기 발광 소자 및 유기 전기 발광 소자용 재료 |
US20070103055A1 (en) * | 2003-12-19 | 2007-05-10 | Idemitsu Losan Co., Ltd. | Organic electroluminescence device, conductive laminate and display |
KR100577262B1 (ko) | 2004-01-06 | 2006-05-10 | 엘지전자 주식회사 | 유기전계발광소자 |
US9085729B2 (en) * | 2004-02-09 | 2015-07-21 | Lg Display Co., Ltd. | Blue emitters for use in organic electroluminescence devices |
US7252893B2 (en) * | 2004-02-17 | 2007-08-07 | Eastman Kodak Company | Anthracene derivative host having ranges of dopants |
JPWO2005081587A1 (ja) * | 2004-02-19 | 2008-01-17 | 出光興産株式会社 | 白色系有機エレクトロルミネッセンス素子 |
JPWO2005091686A1 (ja) * | 2004-03-19 | 2008-02-07 | チッソ株式会社 | 有機電界発光素子 |
JP4734836B2 (ja) * | 2004-03-19 | 2011-07-27 | 富士ゼロックス株式会社 | 電界発光素子 |
WO2005091684A1 (ja) * | 2004-03-19 | 2005-09-29 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子 |
JP2005302667A (ja) * | 2004-04-15 | 2005-10-27 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
CN1960957A (zh) * | 2004-05-27 | 2007-05-09 | 出光兴产株式会社 | 不对称芘衍生物以及使用该衍生物的有机电致发光器件 |
TWI290582B (en) * | 2004-07-06 | 2007-12-01 | Au Optronics Corp | Anthracene compound and organic electroluminescent device including the anthracene compound |
JP4788202B2 (ja) * | 2004-07-09 | 2011-10-05 | Jnc株式会社 | 発光材料およびこれを用いた有機電界発光素子 |
US20060019116A1 (en) * | 2004-07-22 | 2006-01-26 | Eastman Kodak Company | White electroluminescent device with anthracene derivative host |
US7449830B2 (en) | 2004-08-02 | 2008-11-11 | Lg Display Co., Ltd. | OLEDs having improved luminance stability |
US7449831B2 (en) | 2004-08-02 | 2008-11-11 | Lg Display Co., Ltd. | OLEDs having inorganic material containing anode capping layer |
US7544425B2 (en) * | 2004-10-29 | 2009-06-09 | Eastman Kodak Company | Organic element for electroluminescent devices |
US7666524B2 (en) * | 2004-10-29 | 2010-02-23 | Semiconductor Energy Laboratory Co., Ltd. | Oligonaphthalene derivatives, and light-emitting element and light-emitting device using oligonaphthalene derivatives |
EP1829855A4 (en) * | 2004-11-08 | 2009-03-11 | Bando Chemical Ind | NOVEL AROMATIC TERTIARY AMINES AND USE THEREOF AS ORGANIC MATERIAL FOR ELECTRONIC APPLICATIONS |
WO2006072001A2 (en) * | 2004-12-29 | 2006-07-06 | E.I. Dupont De Nemours And Company | Active compositions and methods |
US8057916B2 (en) * | 2005-04-20 | 2011-11-15 | Global Oled Technology, Llc. | OLED device with improved performance |
US20060240281A1 (en) * | 2005-04-21 | 2006-10-26 | Eastman Kodak Company | Contaminant-scavenging layer on OLED anodes |
TWI268121B (en) | 2005-04-21 | 2006-12-01 | Au Optronics Corp | Light emission material and organic electroluminescent device using the same |
US8487527B2 (en) | 2005-05-04 | 2013-07-16 | Lg Display Co., Ltd. | Organic light emitting devices |
US7777407B2 (en) | 2005-05-04 | 2010-08-17 | Lg Display Co., Ltd. | Organic light emitting devices comprising a doped triazine electron transport layer |
US7728517B2 (en) | 2005-05-20 | 2010-06-01 | Lg Display Co., Ltd. | Intermediate electrodes for stacked OLEDs |
US7750561B2 (en) | 2005-05-20 | 2010-07-06 | Lg Display Co., Ltd. | Stacked OLED structure |
US7943244B2 (en) | 2005-05-20 | 2011-05-17 | Lg Display Co., Ltd. | Display device with metal-organic mixed layer anodes |
US7811679B2 (en) | 2005-05-20 | 2010-10-12 | Lg Display Co., Ltd. | Display devices with light absorbing metal nanoparticle layers |
US7795806B2 (en) | 2005-05-20 | 2010-09-14 | Lg Display Co., Ltd. | Reduced reflectance display devices containing a thin-layer metal-organic mixed layer (MOML) |
KR100788254B1 (ko) * | 2005-08-16 | 2007-12-27 | (주)그라쎌 | 녹색 발광 화합물 및 이를 발광재료로서 채용하고 있는발광소자 |
DE102005040411A1 (de) | 2005-08-26 | 2007-03-01 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US20070048545A1 (en) * | 2005-08-31 | 2007-03-01 | Eastman Kodak Company | Electron-transporting layer for white OLED device |
WO2007026626A1 (en) | 2005-08-31 | 2007-03-08 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, material for light emitting element, light emitting element, light emitting device, and electronic device |
US20070092754A1 (en) * | 2005-10-26 | 2007-04-26 | Eastman Kodak Company | Organic element for low voltage electroluminescent devices |
KR100828173B1 (ko) * | 2005-11-22 | 2008-05-08 | (주)그라쎌 | 유기 발광 화합물 및 이를 발광재료로 채용하고 있는 표시소자 |
DE102005058557A1 (de) * | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102005058558A1 (de) * | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
JP5420249B2 (ja) | 2005-12-08 | 2014-02-19 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネセンス素子のための新規な材料 |
KR100851739B1 (ko) | 2006-01-13 | 2008-08-11 | 주식회사 엘지화학 | 발광 물질 및 이를 이용한 유기발광소자 |
KR100670383B1 (ko) | 2006-01-18 | 2007-01-16 | 삼성에스디아이 주식회사 | 유기 발광 소자 및 이를 구비한 평판 표시 장치 |
TWI371987B (en) * | 2006-01-18 | 2012-09-01 | Lg Chemical Ltd | Oled having stacked organic light-emitting units |
KR100872692B1 (ko) * | 2006-03-06 | 2008-12-10 | 주식회사 엘지화학 | 신규한 안트라센 유도체 및 이를 이용한 유기 전자 소자 |
KR100667973B1 (ko) * | 2006-03-09 | 2007-01-11 | 주식회사 잉크테크 | 신규한 디스티릴아릴렌계 화합물 및 이를 이용한 유기전기발광 소자 |
DE102006013802A1 (de) * | 2006-03-24 | 2007-09-27 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
EP2355198B1 (en) | 2006-05-08 | 2015-09-09 | Global OLED Technology LLC | OLED electron-injecting layer |
DE102006031990A1 (de) | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US7667391B2 (en) * | 2006-08-04 | 2010-02-23 | Eastman Kodak Company | Electrically excited organic light-emitting diodes with spatial and spectral coherence |
KR100864308B1 (ko) * | 2006-12-28 | 2008-10-20 | 주식회사 두산 | 신규 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자 |
DE102007024850A1 (de) | 2007-05-29 | 2008-12-04 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US20090091242A1 (en) * | 2007-10-05 | 2009-04-09 | Liang-Sheng Liao | Hole-injecting layer in oleds |
KR100935356B1 (ko) * | 2007-11-19 | 2010-01-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 녹색 발광 화합물 및 이를 발광재료로서 채용하고 있는유기 전기 발광 소자 |
US8623520B2 (en) * | 2007-11-21 | 2014-01-07 | Idemitsu Kosan Co., Ltd. | Fused aromatic derivative and organic electroluminescence device using the same |
CN101918511A (zh) * | 2007-11-23 | 2010-12-15 | 葛来西雅帝史派有限公司 | 发光化合物和使用该化合物的电致发光器件 |
KR100940938B1 (ko) * | 2007-12-04 | 2010-02-08 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전기 발광 소자 |
KR100991416B1 (ko) * | 2007-12-31 | 2010-11-03 | 다우어드밴스드디스플레이머티리얼 유한회사 | 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
KR100974562B1 (ko) * | 2007-12-31 | 2010-08-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
DE102008008953B4 (de) | 2008-02-13 | 2019-05-09 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US8115399B2 (en) * | 2008-02-19 | 2012-02-14 | General Electric Company | OLED light source |
KR101001384B1 (ko) * | 2008-02-29 | 2010-12-14 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전기 발광 소자 |
KR100864303B1 (ko) * | 2008-03-05 | 2008-10-20 | 주식회사 두산 | 신규 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자 |
KR100901887B1 (ko) * | 2008-03-14 | 2009-06-09 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 발광소자 |
KR100989815B1 (ko) * | 2008-03-20 | 2010-10-29 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR100946411B1 (ko) * | 2008-03-28 | 2010-03-09 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR20090105495A (ko) * | 2008-04-02 | 2009-10-07 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전기 발광 소자 |
KR100910150B1 (ko) * | 2008-04-02 | 2009-08-03 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
DE102008018670A1 (de) | 2008-04-14 | 2009-10-15 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
KR101495547B1 (ko) * | 2008-04-17 | 2015-02-25 | 롬엔드하스전자재료코리아유한회사 | 신규한 전자 재료용 화합물 및 이를 포함하는 유기 전자소자 |
KR20090111915A (ko) * | 2008-04-23 | 2009-10-28 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR20100000772A (ko) * | 2008-06-25 | 2010-01-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
EP2145936A3 (en) * | 2008-07-14 | 2010-03-17 | Gracel Display Inc. | Fluorene and pyrene derivatives and organic electroluminescent device using the same |
KR20100041043A (ko) * | 2008-10-13 | 2010-04-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 |
DE102008054141A1 (de) | 2008-10-31 | 2010-05-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009005746A1 (de) | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US8147989B2 (en) * | 2009-02-27 | 2012-04-03 | Global Oled Technology Llc | OLED device with stabilized green light-emitting layer |
DE102009033371A1 (de) | 2009-07-16 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009034625A1 (de) | 2009-07-27 | 2011-02-03 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US8581262B2 (en) | 2009-08-04 | 2013-11-12 | Merck Patent Gmbh | Electronic devices comprising multi cyclic hydrocarbons |
DE102009051172A1 (de) | 2009-10-29 | 2011-05-05 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009053191A1 (de) | 2009-11-06 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009052428A1 (de) | 2009-11-10 | 2011-05-12 | Merck Patent Gmbh | Verbindung für elektronische Vorrichtungen |
US8242489B2 (en) * | 2009-12-17 | 2012-08-14 | Global Oled Technology, Llc. | OLED with high efficiency blue light-emitting layer |
EP2517278B1 (en) | 2009-12-22 | 2019-07-17 | Merck Patent GmbH | Electroluminescent formulations |
EP2517537B1 (en) | 2009-12-22 | 2019-04-03 | Merck Patent GmbH | Electroluminescent functional surfactants |
EP2517275B1 (en) | 2009-12-22 | 2018-11-07 | Merck Patent GmbH | Formulations comprising phase-separated functional materials |
DE102010005697A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
EP2545600A2 (en) | 2010-03-11 | 2013-01-16 | Merck Patent GmbH | Radiative fibers |
JP6246468B2 (ja) | 2010-03-11 | 2017-12-13 | メルク パテント ゲーエムベーハー | 治療および化粧品におけるファイバー |
KR101191644B1 (ko) | 2010-05-18 | 2012-10-17 | 삼성디스플레이 주식회사 | 유기 재료와 이를 이용한 유기 발광 장치 |
WO2011147522A1 (en) | 2010-05-27 | 2011-12-01 | Merck Patent Gmbh | Compositions comprising quantum dots |
CN103026525B (zh) | 2010-07-26 | 2016-11-09 | 默克专利有限公司 | 在器件中的纳米晶体 |
DE102010048074A1 (de) | 2010-10-09 | 2012-04-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010054316A1 (de) | 2010-12-13 | 2012-06-14 | Merck Patent Gmbh | Substituierte Tetraarylbenzole |
CN102533092A (zh) * | 2010-12-30 | 2012-07-04 | 拜耳材料科技(中国)有限公司 | 一种聚氨酯涂料成膜物、聚氨酯涂料及其应用 |
DE102011011104A1 (de) | 2011-02-12 | 2012-08-16 | Merck Patent Gmbh | Substituierte Dibenzonaphtacene |
JP6351974B2 (ja) | 2011-02-14 | 2018-07-04 | メルク パテント ゲーエムベーハー | 細胞および細胞組織の処置のためのデバイスおよび方法 |
EP2688646A1 (en) | 2011-03-24 | 2014-01-29 | Merck Patent GmbH | Organic ionic functional materials |
US9496502B2 (en) | 2011-05-12 | 2016-11-15 | Merck Patent Gmbh | Organic ionic compounds, compositions and electronic devices |
JP6174024B2 (ja) | 2011-07-25 | 2017-08-02 | メルク パテント ゲーエムベーハー | 機能性側鎖を有するコポリマー |
JP6282114B2 (ja) * | 2011-10-04 | 2018-02-21 | 株式会社Joled | 有機エレクトロルミネッセンス素子 |
KR102126877B1 (ko) | 2012-02-03 | 2020-06-25 | 이데미쓰 고산 가부시키가이샤 | 카르바졸 화합물, 유기 일렉트로루미네선스 소자용 재료 및 유기 일렉트로루미네선스 소자 |
CN103450883B (zh) * | 2012-05-30 | 2016-03-02 | 京东方科技集团股份有限公司 | 有机电子材料 |
CN103456897B (zh) * | 2012-05-30 | 2016-03-09 | 京东方科技集团股份有限公司 | 有机电致发光器件 |
CN105409022B (zh) | 2013-07-29 | 2018-06-19 | 默克专利有限公司 | 电光器件及其用途 |
US20160181537A1 (en) | 2013-07-29 | 2016-06-23 | Merck Patent Gmbh | Electroluminescence Device |
CN105408448B (zh) | 2013-07-30 | 2018-11-02 | 默克专利有限公司 | 用于电子器件的材料 |
EP3712229A1 (de) | 2013-07-30 | 2020-09-23 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
CN103664495B (zh) * | 2013-12-10 | 2016-07-06 | 京东方科技集团股份有限公司 | 蒽类衍生物及制备方法、应用和有机发光器件 |
CN106255687B (zh) | 2014-04-30 | 2020-06-05 | 默克专利有限公司 | 用于电子器件的材料 |
DE102014008722B4 (de) | 2014-06-18 | 2024-08-22 | Merck Patent Gmbh | Zusammensetzungen für elektronische Vorrichtungen, Formulierung diese enthaltend, Verwendung der Zusammensetzung, Verwendung der Formulierung sowie organische elektronische Vorrichtung enthaltend die Zusammensetzung |
KR102385227B1 (ko) * | 2014-12-02 | 2022-04-12 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
CN107406384B (zh) | 2014-12-04 | 2021-07-23 | 广州华睿光电材料有限公司 | 氘化的有机化合物、包含该化合物的混合物、组合物及有机电子器件 |
US10840450B2 (en) | 2014-12-04 | 2020-11-17 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Polymer, and mixture or formulation, and organic electronic device containing same, and monomer thereof |
WO2016091219A1 (zh) | 2014-12-11 | 2016-06-16 | 广州华睿光电材料有限公司 | 有机化合物、包含其的混合物、组合物和有机电子器件 |
WO2016091217A1 (zh) | 2014-12-11 | 2016-06-16 | 广州华睿光电材料有限公司 | 一种有机金属配合物、包含其的聚合物、混合物、组合物、有机电子器件及应用 |
CN108291103B (zh) | 2015-11-12 | 2021-12-07 | 广州华睿光电材料有限公司 | 印刷组合物、包含其的电子器件及功能材料薄膜的制备方法 |
US11248138B2 (en) | 2016-11-23 | 2022-02-15 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Printing ink formulations, preparation methods and uses thereof |
CN109791993B (zh) | 2016-11-23 | 2021-01-15 | 广州华睿光电材料有限公司 | 有机混合物、组合物以及有机电子器件 |
US11518723B2 (en) | 2016-11-23 | 2022-12-06 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Fused ring compound, high polymer, mixture, composition and organic electronic component |
US11447496B2 (en) | 2016-11-23 | 2022-09-20 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Nitrogen-containing fused heterocyclic ring compound and application thereof |
CN109791992B (zh) | 2016-11-23 | 2021-07-23 | 广州华睿光电材料有限公司 | 高聚物、包含其的混合物、组合物和有机电子器件以及用于聚合的单体 |
WO2018095382A1 (zh) | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | 芳香胺衍生物及其制备方法和用途 |
CN109790194B (zh) | 2016-11-23 | 2021-07-23 | 广州华睿光电材料有限公司 | 金属有机配合物、高聚物、组合物及有机电子器件 |
CN109790129B (zh) | 2016-12-08 | 2022-08-12 | 广州华睿光电材料有限公司 | 芘三嗪类衍生物及其在有机电子器件中的应用 |
WO2018108108A1 (zh) | 2016-12-13 | 2018-06-21 | 广州华睿光电材料有限公司 | 共轭聚合物及其在有机电子器件的应用 |
US11292875B2 (en) | 2016-12-22 | 2022-04-05 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Cross-linkable polymer based on Diels-Alder reaction and use thereof in organic electronic device |
CN109790136B (zh) | 2016-12-22 | 2024-01-12 | 广州华睿光电材料有限公司 | 含呋喃交联基团的聚合物及其应用 |
WO2018150832A1 (ja) * | 2017-02-16 | 2018-08-23 | 学校法人関西学院 | 有機電界発光素子 |
US11778907B2 (en) | 2017-04-13 | 2023-10-03 | Merck Patent Gmbh | Composition for organic electronic devices |
JP7325731B2 (ja) | 2018-08-23 | 2023-08-15 | 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 |
EP4139971A1 (en) | 2020-04-21 | 2023-03-01 | Merck Patent GmbH | Emulsions comprising organic functional materials |
CN116391006A (zh) | 2020-10-14 | 2023-07-04 | 浙江光昊光电科技有限公司 | 组合物及其在光电领域的应用 |
WO2023012084A1 (en) | 2021-08-02 | 2023-02-09 | Merck Patent Gmbh | A printing method by combining inks |
TW202411366A (zh) | 2022-06-07 | 2024-03-16 | 德商麥克專利有限公司 | 藉由組合油墨來印刷電子裝置功能層之方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01174079A (ja) * | 1987-12-28 | 1989-07-10 | Hitachi Ltd | 画像処理回路 |
EP0836366A1 (en) * | 1996-10-08 | 1998-04-15 | Idemitsu Kosan Company Limited | Organic electroluminescent device |
JPH1174079A (ja) * | 1997-06-20 | 1999-03-16 | Nec Corp | 有機エレクトロルミネッセンス素子 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01174097A (ja) * | 1987-12-28 | 1989-07-10 | Toshiba Corp | プロセス監視制御システム |
EP1056140B1 (en) * | 1992-08-28 | 2005-07-06 | Idemitsu Kosan Company Limited | Charge injection auxiliary material |
US5652067A (en) * | 1992-09-10 | 1997-07-29 | Toppan Printing Co., Ltd. | Organic electroluminescent device |
EP0681019B1 (en) * | 1994-04-26 | 1999-09-01 | TDK Corporation | Phenylanthracene derivative and organic EL element |
JP3529543B2 (ja) * | 1995-04-27 | 2004-05-24 | パイオニア株式会社 | 有機エレクトロルミネッセンス素子 |
US5981092A (en) * | 1996-03-25 | 1999-11-09 | Tdk Corporation | Organic El device |
JP3564859B2 (ja) * | 1996-04-01 | 2004-09-15 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子用材料およびそれを使用した有機エレクトロルミネッセンス素子 |
JP3228502B2 (ja) * | 1996-10-08 | 2001-11-12 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
JP3949214B2 (ja) * | 1997-03-18 | 2007-07-25 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
US5935721A (en) * | 1998-03-20 | 1999-08-10 | Eastman Kodak Company | Organic electroluminescent elements for stable electroluminescent |
US6140763A (en) * | 1998-07-28 | 2000-10-31 | Eastman Kodak Company | Interfacial electron-injecting layer formed from a doped cathode for organic light-emitting structure |
JP2000164363A (ja) * | 1998-11-25 | 2000-06-16 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP2001052870A (ja) * | 1999-06-03 | 2001-02-23 | Tdk Corp | 有機el素子 |
-
2000
- 2000-09-20 KR KR1020017006271A patent/KR100809132B1/ko active IP Right Grant
- 2000-09-20 EP EP07101123A patent/EP1775783A3/en not_active Ceased
- 2000-09-20 AT AT00961101T patent/ATE360892T1/de not_active IP Right Cessation
- 2000-09-20 WO PCT/JP2000/006402 patent/WO2001021729A1/ja active Application Filing
- 2000-09-20 KR KR1020077019127A patent/KR100790663B1/ko not_active IP Right Cessation
- 2000-09-20 TW TW089119391A patent/TW474113B/zh not_active IP Right Cessation
- 2000-09-20 DE DE60034560T patent/DE60034560T2/de not_active Expired - Lifetime
- 2000-09-20 EP EP00961101A patent/EP1167488B1/en not_active Revoked
- 2000-09-20 JP JP2001525292A patent/JP5073899B2/ja not_active Expired - Fee Related
- 2000-09-20 US US09/665,416 patent/US6534199B1/en not_active Expired - Lifetime
- 2000-09-20 KR KR1020057017620A patent/KR100738762B1/ko not_active IP Right Cessation
- 2000-09-20 CN CNB008020027A patent/CN1208422C/zh not_active Expired - Lifetime
- 2000-09-20 KR KR1020077006875A patent/KR100799799B1/ko not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01174079A (ja) * | 1987-12-28 | 1989-07-10 | Hitachi Ltd | 画像処理回路 |
EP0836366A1 (en) * | 1996-10-08 | 1998-04-15 | Idemitsu Kosan Company Limited | Organic electroluminescent device |
JPH1174079A (ja) * | 1997-06-20 | 1999-03-16 | Nec Corp | 有機エレクトロルミネッセンス素子 |
Also Published As
Publication number | Publication date |
---|---|
EP1167488A1 (en) | 2002-01-02 |
EP1167488A4 (en) | 2005-09-07 |
DE60034560T2 (de) | 2007-08-16 |
JP5073899B2 (ja) | 2012-11-14 |
KR20070042584A (ko) | 2007-04-23 |
CN1322232A (zh) | 2001-11-14 |
TW474113B (en) | 2002-01-21 |
DE60034560D1 (de) | 2007-06-06 |
KR100799799B1 (ko) | 2008-02-01 |
KR20070091375A (ko) | 2007-09-10 |
CN1208422C (zh) | 2005-06-29 |
EP1167488B1 (en) | 2007-04-25 |
KR20010080488A (ko) | 2001-08-22 |
EP1775783A3 (en) | 2008-04-16 |
WO2001021729A1 (fr) | 2001-03-29 |
EP1775783A2 (en) | 2007-04-18 |
US6534199B1 (en) | 2003-03-18 |
KR100790663B1 (ko) | 2008-01-03 |
KR100738762B1 (ko) | 2007-07-12 |
KR20050100708A (ko) | 2005-10-19 |
ATE360892T1 (de) | 2007-05-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100809132B1 (ko) | 유기 전자발광 소자 및 유기 발광 매체 | |
KR100572440B1 (ko) | 유기 전자발광 소자 및 유기 발광 매체 | |
JP2012019229A (ja) | 有機エレクトロルミネッセンス素子及び有機発光媒体 | |
WO2005101913A1 (ja) | 有機エレクトロルミネッセンス素子 | |
JP3974720B2 (ja) | 有機el素子 | |
KR100842980B1 (ko) | 유기 전기발광 소자 | |
EP1009042A2 (en) | Electroliuminescent device with arylethylene derivatives in hole transport layer | |
JP2006287248A (ja) | 有機エレクトロルミネッセンス素子及び有機発光媒体 | |
KR100660001B1 (ko) | 전자 래더층을 갖는 유기 전계 발광 소자 | |
KR100682766B1 (ko) | 전자 래더층을 갖는 유기 전계 발광 소자 | |
KR100644530B1 (ko) | 전자 래더층을 갖는 유기 전계 발광 소자 | |
KR100682824B1 (ko) | 고효율의 유기 전계 발광 소자 | |
KR100660010B1 (ko) | 전자 래더층을 갖는 유기 전계 발광 소자 | |
KR100662599B1 (ko) | 고효율의 유기 전계 발광 소자 | |
KR100682833B1 (ko) | 고효율의 유기 전계 발광 소자 | |
KR100682765B1 (ko) | 전자 래더층을 갖는 유기 전계 발광 소자 | |
KR100682764B1 (ko) | 전자 래더층을 갖는 유기 전계 발광 소자 | |
KR100746981B1 (ko) | 전자 래더층을 갖는 유기 전계 발광 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A107 | Divisional application of patent | ||
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
A107 | Divisional application of patent | ||
E902 | Notification of reason for refusal | ||
A107 | Divisional application of patent | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
G170 | Re-publication after modification of scope of protection [patent] | ||
FPAY | Annual fee payment |
Payment date: 20130201 Year of fee payment: 6 |
|
FPAY | Annual fee payment |
Payment date: 20140204 Year of fee payment: 7 |
|
FPAY | Annual fee payment |
Payment date: 20150130 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20160127 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20170202 Year of fee payment: 10 |
|
FPAY | Annual fee payment |
Payment date: 20180202 Year of fee payment: 11 |
|
FPAY | Annual fee payment |
Payment date: 20190201 Year of fee payment: 12 |
|
FPAY | Annual fee payment |
Payment date: 20200205 Year of fee payment: 13 |