JP5733294B2 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
- Publication number
- JP5733294B2 JP5733294B2 JP2012264325A JP2012264325A JP5733294B2 JP 5733294 B2 JP5733294 B2 JP 5733294B2 JP 2012264325 A JP2012264325 A JP 2012264325A JP 2012264325 A JP2012264325 A JP 2012264325A JP 5733294 B2 JP5733294 B2 JP 5733294B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- organic
- layer
- light emitting
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000005401 electroluminescence Methods 0.000 title claims description 24
- 239000010410 layer Substances 0.000 claims description 168
- 150000001875 compounds Chemical class 0.000 claims description 101
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052741 iridium Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 2
- -1 2-ethyl-hexyl group Chemical group 0.000 description 119
- 238000000034 method Methods 0.000 description 67
- 239000000463 material Substances 0.000 description 45
- 238000002347 injection Methods 0.000 description 30
- 239000007924 injection Substances 0.000 description 30
- 230000005525 hole transport Effects 0.000 description 25
- 239000000758 substrate Substances 0.000 description 25
- 239000010408 film Substances 0.000 description 24
- 239000002019 doping agent Substances 0.000 description 23
- 230000000903 blocking effect Effects 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- 239000000872 buffer Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 238000007740 vapor deposition Methods 0.000 description 16
- 239000011159 matrix material Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000975 dye Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 238000010586 diagram Methods 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 239000003086 colorant Substances 0.000 description 9
- 239000007772 electrode material Substances 0.000 description 9
- 229910052749 magnesium Inorganic materials 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 238000006862 quantum yield reaction Methods 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 238000005286 illumination Methods 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003990 capacitor Substances 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000000059 patterning Methods 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 238000005266 casting Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000002883 imidazolyl group Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000006798 recombination Effects 0.000 description 5
- 238000005215 recombination Methods 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 229910052738 indium Inorganic materials 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 125000004623 carbolinyl group Chemical group 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 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 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical class [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000003828 azulenyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 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 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005581 pyrene group Chemical group 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- SULWTXOWAFVWOY-PHEQNACWSA-N 2,3-bis[(E)-2-phenylethenyl]pyrazine Chemical class C=1C=CC=CC=1/C=C/C1=NC=CN=C1\C=C\C1=CC=CC=C1 SULWTXOWAFVWOY-PHEQNACWSA-N 0.000 description 1
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical class O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- ZJSMHFNBMMAKRI-UHFFFAOYSA-N 4-[4-(4-methoxyanilino)phenyl]aniline Chemical group COC1=CC=C(C=C1)NC1=CC=C(C=C1)C1=CC=C(C=C1)N ZJSMHFNBMMAKRI-UHFFFAOYSA-N 0.000 description 1
- AHDTYXOIJHCGKH-UHFFFAOYSA-N 4-[[4-(dimethylamino)-2-methylphenyl]-phenylmethyl]-n,n,3-trimethylaniline Chemical compound CC1=CC(N(C)C)=CC=C1C(C=1C(=CC(=CC=1)N(C)C)C)C1=CC=CC=C1 AHDTYXOIJHCGKH-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- DUSWRTUHJVJVRY-UHFFFAOYSA-N 4-methyl-n-[4-[2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]propan-2-yl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C(C)(C)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 DUSWRTUHJVJVRY-UHFFFAOYSA-N 0.000 description 1
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-UHFFFAOYSA-N 0.000 description 1
- XIQGFRHAIQHZBD-UHFFFAOYSA-N 4-methyl-n-[4-[[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]-phenylmethyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 XIQGFRHAIQHZBD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical class C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- BZHCVCNZIJZMRN-UHFFFAOYSA-N 9h-pyridazino[3,4-b]indole Chemical group N1=CC=C2C3=CC=CC=C3NC2=N1 BZHCVCNZIJZMRN-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YLYLXUBEHRALPT-UHFFFAOYSA-N [Ir].C1=CN=C2C3=CC=CC=C3C=CC2=C1.C1=CN=C2C3=CC=CC=C3C=CC2=C1.C1=CN=C2C3=CC=CC=C3C=CC2=C1 Chemical compound [Ir].C1=CN=C2C3=CC=CC=C3C=CC2=C1.C1=CN=C2C3=CC=CC=C3C=CC2=C1.C1=CN=C2C3=CC=CC=C3C=CC2=C1 YLYLXUBEHRALPT-UHFFFAOYSA-N 0.000 description 1
- DEGMMTKFCIBVIE-UHFFFAOYSA-N [Ir].Cc1ccc(cc1)-c1ccccn1.Cc1ccc(cc1)-c1ccccn1.Cc1ccc(cc1)-c1ccccn1 Chemical compound [Ir].Cc1ccc(cc1)-c1ccccn1.Cc1ccc(cc1)-c1ccccn1.Cc1ccc(cc1)-c1ccccn1 DEGMMTKFCIBVIE-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006309 butyl amino group Chemical group 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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- HKQOBOMRSSHSTC-UHFFFAOYSA-N cellulose acetate Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 HKQOBOMRSSHSTC-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000005578 chrysene group Chemical group 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000005583 coronene group Chemical group 0.000 description 1
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000005366 cycloalkylthio group Chemical group 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 229920000775 emeraldine polymer Polymers 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 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 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
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([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
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
- 125000005582 pentacene group Chemical group 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 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
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 150000004841 phenylimidazoles Chemical class 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- LNKHTYQPVMAJSF-UHFFFAOYSA-N pyranthrene Chemical group C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 LNKHTYQPVMAJSF-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000001022 rhodamine dye Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
- 241000894007 species Species 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003756 stirring 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
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000004525 thiadiazinyl group Chemical group S1NN=C(C=C1)* 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Images
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
- 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
- H10K50/00—Organic light-emitting devices
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- 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
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/348—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Description
具体的に本発明は、下記構成1、2、6において、一般式(A)中、A1は、6員芳香族炭化水素環を形成するのに必要な原子群を表し、一般式(3)中、RA、RBは、各々アルキル基、シクロアルキル基、芳香族基または複素環基を表す。
2.前記ゲスト化合物が、下記一般式(A)で表されることを特徴とする前記1に記載の有機エレクトロルミネッセンス素子。
3.前記ゲスト化合物が、下記一般式(B)で表される化合物であることを特徴とする前記1に記載の有機エレクトロルミネッセンス素子。
4.前記ゲスト化合物が、下記一般式(C)で表される化合物であることを特徴とする前記1に記載の有機エレクトロルミネッセンス素子。
5.前記ホスト化合物が、下記一般式(2)で表される化合物であることを特徴とする前記1に記載の有機エレクトロルミネッセンス素子。
6.前記ホスト化合物が、下記一般式(3)で表される化合物であることを特徴とする前記1に記載の有機エレクトロルミネッセンス素子。
7.前記一般式(A)で表されるゲスト化合物のA1で形成される芳香族炭化水素環がベンゼン環であることを特徴とする前記2〜4のいずれか1項に記載の有機エレクトロルミネッセンス素子。
(ii)陽極/正孔輸送層/発光層/電子輸送層/陰極
(iii)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極
(iv)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(v)陽極/陽極バッファー層/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
《陽極》
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としてはAu等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3−ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に膜厚は材料にもよるが、通常10〜1000nm、好ましくは10〜200nmの範囲で選ばれる。
一方、陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム−カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm〜5μm、好ましくは50nm〜200nmの範囲で選ばれる。尚、発光した光を透過させるため、有機EL素子の陽極または陰極のいずれか一方が、透明または半透明であれば発光輝度が向上し好都合である。
注入層は必要に応じて設け、電子注入層と正孔注入層があり、上記のごとく陽極と発光層または正孔輸送層の間、及び陰極と発光層または電子輸送層との間に存在させてもよい。
阻止層は、上記のごとく有機化合物薄膜の基本構成層の他に必要に応じて設けられるものである。例えば、特開平11−204258号公報、同11−204359号公報の各公報、及び「有機EL素子とその工業化最前線(1998年11月30日エヌ・ティー・エス社発行)」の237頁等に記載されている正孔阻止(ホールブロック)層がある。
本発明に係る発光層は、電極または電子輸送層、正孔輸送層から注入されてくる電子及び正孔が再結合して発光する層であり、発光する部分は発光層の層内であっても発光層と隣接層との界面であってもよい。
本発明の有機EL素子の発光層には、上記のホスト化合物と発光ドーパント(リン光発光性化合物ともいう)が含有されることが好ましく、本発明においては、ホスト化合物として前述した本発明に係る化合物を用いることが好ましい。これにより、より一層発光効率を高くすることができる。またホスト化合物として、上記の本発明に係る化合物以外の化合物を含有してもよい。
本発明に係るゲスト化合物(発光ドーパントともいう)は、励起三重項からの発光が観測される化合物であり、室温(25℃)にてリン光発光する化合物であり、リン光量子収率が、25℃において0.01以上の化合物である。リン光量子収率は好ましくは0.1以上である。上記リン光量子収率は、第4版実験化学講座7の分光IIの398頁(1992年版、丸善)に記載の方法により測定できる。溶液中でのリン光量子収率は種々の溶媒を用いて測定できるが、本発明に係るゲスト化合物は、任意の溶媒のいずれかにおいて上記リン光量子収率が達成されればよい。
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料からなり、広い意味で正孔注入層、電子阻止層も正孔輸送層に含まれる。正孔輸送層は単層または複数層設けることができる。
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入層、正孔阻止層も電子輸送層に含まれる。電子輸送層は単層または複数層設けることができる。
本発明の有機EL素子は、基体上に形成されているのが好ましい。
本発明の有機EL素子の作製方法の一例として、陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極からなる有機EL素子の作製法について説明する。
本発明の有機EL素子は、照明用や露光光源のような1種のランプとして使用してもよいし、画像を投影するタイプのプロジェクション装置や静止画像や動画像を直接視認するタイプの表示装置(ディスプレイ)として使用してもよい。動画再生用の表示装置として使用する場合の駆動方式は単純マトリクス(パッシブマトリクス)方式でもアクティブマトリクス方式でもどちらでもよい。または、異なる発光色を有する本発明の有機EL素子を3種以上使用することにより、フルカラー表示装置を作製することが可能である。または一色の発光色、例えば、白色発光をカラーフィルターを用いてBGRにし、フルカラー化することも可能である。更に有機ELの発光色を色変換フィルターを用いて他色に変換しフルカラー化することも可能であるが、その場合、有機EL発光のλmaxは480nm以下であることが好ましい。
《有機EL素子1−1の作製》
陽極として100mm×100mm×1.1mmのガラス基板上にITO(インジウムチンオキシド)を100nm製膜した基板(NHテクノグラス社製NA45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行なった。この透明支持基板を市販の真空蒸着装置の基板ホルダーに固定し、一方モリブデン製抵抗加熱ボートにα−NPDを200mg入れ、別のモリブデン製抵抗加熱ボートにホスト化合物としてCBPを200mg入れ、別のモリブデン製抵抗加熱ボートにバソキュプロイン(BCP)を200mg入れ、別のモリブデン製抵抗加熱ボートにD−1を100mg入れ、更に別のモリブデン製抵抗加熱ボートにAlq3を200mg入れ、真空蒸着装置に取付けた。
有機EL素子1−1の作製において、発光層のホスト化合物として用いているCBPを表1に示す化合物に置き換えてホスト化合物とし、発光層の発光ドーパントとして用いているD−1を表1に示す化合物に置き換えて発光ドーパントとした以外は、有機EL素子1−1と同じ方法で1−2〜1−20を作製した。上記で使用した化合物の構造を以下に示す。
以下のようにして作製した有機EL素子1−1〜1−20の評価を行い、その結果を表1に示す。
作製した有機EL素子について、23℃、乾燥窒素ガス雰囲気下で2.5mA/cm2定電流を印加した時の外部取り出し量子効率(%)を測定した。尚、測定には同様に分光放射輝度計CS−1000(コニカミノルタセンシング社製)を用いた。表1の外部取り出し量子効率の測定結果は、有機EL素子1−1の測定値を100とした時の相対値で表した。
2.5mA/cm2の一定電流で駆動したときに、輝度が発光開始直後の輝度(初期輝度)の半分に低下するのに要した時間を測定し、これを半減寿命時間(τ0.5)として寿命の指標とした。尚、測定には分光放射輝度計CS−1000(コニカミノルタセンシング社製)を用いた。表1の寿命の測定結果は、有機EL素子1−1を100とした時の相対値で表した。
実施例1の透明電極基板の電極を20mm×20mmにパターニングし、その上に実施例1と同様に正孔注入/輸送層としてα−NPDを50nmの厚さで製膜し、更にH−1の入った前記加熱ボートとD−1の入ったボート及びIr−9の入ったボートをそれぞれ独立に通電して、ホスト化合物である化合物H−1と発光ドーパントであるD−1及びIr−9の蒸着速度が100:5:0.6になるように調節し、膜厚30nmの厚さになるように蒸着し、発光層を設けた。
《フルカラー表示装置の作製》
(青色発光素子の作製)
実施例1の有機EL素子1−3を青色発光素子として用いた。
実施例1の有機EL素子1−3において、ホスト化合物をCBP、ドーパントをIr−1に変更した以外は同様にして、緑色発光素子を作製し、これを緑色発光素子として用いた。
実施例1の有機EL素子1−3において、ホスト化合物をCBP、ドーパントをIr−1に変更した以外は同様にして、赤色発光素子を作製し、これを赤色発光素子として用いた。
《照明装置の作製》
参考例2で作製した青色発光、緑色発光及び赤色発光の有機EL素子の各々の非発光面をガラスケースで覆い、照明装置とした。照明装置は発光効率が高く、発光寿命の長い白色光を発する薄型の照明装置として使用することができた。図5は照明装置の概略図で、図6は照明装置の断面図である。有機EL素子101をガラスカバー102で覆った。
3 画素
5 走査線
6 データ線
7 電源ライン
10 有機EL素子
11 スイッチングトランジスタ
12 駆動トランジスタ
13 コンデンサ
A 表示部
B 制御部
102 ガラスカバー
105 陰極
106 有機EL層
107 透明電極付きガラス基板
108 窒素ガス
109 捕水剤
Claims (2)
- 陽極と陰極により挟まれた少なくとも発光層を含有する有機エレクトロルミネッセンス素子において、
該発光層が、少なくとも一つの下記一般式(A)で表される部分構造を含むゲスト化合物及び、少なくとも一つの下記一般式(3)で表されるホスト化合物を含有することを特徴とする有機エレクトロルミネッセンス素子。
- 前記一般式(3)中、RA、RBがメチル基であることを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012264325A JP5733294B2 (ja) | 2005-06-09 | 2012-12-03 | 有機エレクトロルミネッセンス素子 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005169227 | 2005-06-09 | ||
JP2005169227 | 2005-06-09 | ||
JP2012264325A JP5733294B2 (ja) | 2005-06-09 | 2012-12-03 | 有機エレクトロルミネッセンス素子 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007520029A Division JPWO2006132012A1 (ja) | 2005-06-09 | 2006-03-03 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013102165A JP2013102165A (ja) | 2013-05-23 |
JP5733294B2 true JP5733294B2 (ja) | 2015-06-10 |
Family
ID=37498221
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007520029A Pending JPWO2006132012A1 (ja) | 2005-06-09 | 2006-03-03 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP2011268592A Active JP5790463B2 (ja) | 2005-06-09 | 2011-12-08 | 有機エレクトロルミネッセンス素子 |
JP2011268590A Pending JP2012109575A (ja) | 2005-06-09 | 2011-12-08 | 有機エレクトロルミネッセンス素子 |
JP2012264325A Active JP5733294B2 (ja) | 2005-06-09 | 2012-12-03 | 有機エレクトロルミネッセンス素子 |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007520029A Pending JPWO2006132012A1 (ja) | 2005-06-09 | 2006-03-03 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP2011268592A Active JP5790463B2 (ja) | 2005-06-09 | 2011-12-08 | 有機エレクトロルミネッセンス素子 |
JP2011268590A Pending JP2012109575A (ja) | 2005-06-09 | 2011-12-08 | 有機エレクトロルミネッセンス素子 |
Country Status (4)
Country | Link |
---|---|
US (3) | US8808874B2 (ja) |
JP (4) | JPWO2006132012A1 (ja) |
GB (2) | GB2476003B (ja) |
WO (1) | WO2006132012A1 (ja) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006132012A1 (ja) * | 2005-06-09 | 2006-12-14 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP5017858B2 (ja) * | 2005-12-27 | 2012-09-05 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
JP5233081B2 (ja) * | 2006-05-17 | 2013-07-10 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5556014B2 (ja) * | 2006-09-20 | 2014-07-23 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子 |
EP1918349A1 (en) * | 2006-10-12 | 2008-05-07 | SOLVAY (Société Anonyme) | Light-emitting material |
CN101679857B (zh) * | 2007-07-27 | 2012-11-28 | 东丽株式会社 | 发光元件材料和发光元件 |
KR100882911B1 (ko) * | 2007-08-16 | 2009-02-10 | 삼성모바일디스플레이주식회사 | 유기전계발광소자 및 그의 제조방법 |
WO2009085344A2 (en) * | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
WO2009133753A1 (ja) * | 2008-04-30 | 2009-11-05 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
US20120037889A1 (en) * | 2008-12-08 | 2012-02-16 | Konica Minolta Holdings, Inc. | Organic electroluminescence element, display device and illumination device |
WO2010119891A1 (ja) * | 2009-04-14 | 2010-10-21 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
JP5719125B2 (ja) * | 2010-06-10 | 2015-05-13 | ユー・ディー・シー アイルランド リミテッド | 特定構造のカルバゾール系化合物、並びにそれを用いた電荷輸送材料及び有機電界発光素子 |
US10243023B2 (en) | 2013-01-18 | 2019-03-26 | Universal Display Corporation | Top emission AMOLED displays using two emissive layers |
US9590017B2 (en) | 2013-01-18 | 2017-03-07 | Universal Display Corporation | High resolution low power consumption OLED display with extended lifetime |
US10304906B2 (en) | 2013-01-18 | 2019-05-28 | Universal Display Corporation | High resolution low power consumption OLED display with extended lifetime |
US9385168B2 (en) * | 2013-01-18 | 2016-07-05 | Universal Display Corporation | High resolution low power consumption OLED display with extended lifetime |
US10229956B2 (en) | 2013-01-18 | 2019-03-12 | Universal Display Corporation | High resolution low power consumption OLED display with extended lifetime |
US10580832B2 (en) | 2013-01-18 | 2020-03-03 | Universal Display Corporation | High resolution low power consumption OLED display with extended lifetime |
JP2014227399A (ja) * | 2013-05-24 | 2014-12-08 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | アリールアミン誘導体及びそれを正孔輸送材料に用いた有機電界発光素子 |
US10700134B2 (en) | 2014-05-27 | 2020-06-30 | Universal Display Corporation | Low power consumption OLED display |
US10672995B2 (en) * | 2014-07-24 | 2020-06-02 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US10263050B2 (en) | 2015-09-18 | 2019-04-16 | Universal Display Corporation | Hybrid display |
US9818804B2 (en) | 2015-09-18 | 2017-11-14 | Universal Display Corporation | Hybrid display |
US10797112B2 (en) | 2018-07-25 | 2020-10-06 | Universal Display Corporation | Energy efficient OLED TV |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020022588A1 (en) * | 1998-06-23 | 2002-02-21 | James Wilkie | Methods and compositions for sealing tissue leaks |
US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
EP2270895A3 (en) | 1999-12-01 | 2011-03-30 | The Trustees of Princeton University | Complexes for OLEDs |
US6660410B2 (en) * | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
EP2566302B1 (en) | 2000-08-11 | 2015-12-16 | The Trustees of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorence |
US6939624B2 (en) | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
GB0021513D0 (en) * | 2000-09-01 | 2000-10-18 | E2 One Uk Ltd | Method and system for dynamic web-page generation and computer-readable storage medium storing a program for performing the method |
JP4086499B2 (ja) | 2000-11-29 | 2008-05-14 | キヤノン株式会社 | 金属配位化合物、発光素子及び表示装置 |
JP4086498B2 (ja) | 2000-11-29 | 2008-05-14 | キヤノン株式会社 | 金属配位化合物、発光素子及び表示装置 |
JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP4438042B2 (ja) | 2001-03-08 | 2010-03-24 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
JP4307001B2 (ja) | 2001-03-14 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
JP5135660B2 (ja) * | 2001-09-27 | 2013-02-06 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
US6863997B2 (en) * | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
JP4316387B2 (ja) | 2002-03-22 | 2009-08-19 | 出光興産株式会社 | 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 |
CN1656194A (zh) * | 2002-03-25 | 2005-08-17 | 出光兴产株式会社 | 用于有机电致发光元件的材料和应用该材料的有机电致发光元件 |
JP2003317946A (ja) * | 2002-04-23 | 2003-11-07 | Konica Minolta Holdings Inc | 有機el素子及び有機el素子の製造方法 |
JP4103491B2 (ja) * | 2002-08-07 | 2008-06-18 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
US20060257684A1 (en) | 2002-10-09 | 2006-11-16 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
EP2248870B1 (en) * | 2002-11-26 | 2018-12-26 | Konica Minolta Holdings, Inc. | Organic electroluminscent element and display and illuminator |
JP4707082B2 (ja) * | 2002-11-26 | 2011-06-22 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子および表示装置 |
JP4254211B2 (ja) * | 2002-11-26 | 2009-04-15 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
JP4356363B2 (ja) * | 2002-11-26 | 2009-11-04 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及びそれを有する表示装置 |
JPWO2004074399A1 (ja) * | 2003-02-20 | 2006-06-01 | 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 |
JP4590825B2 (ja) * | 2003-02-21 | 2010-12-01 | コニカミノルタホールディングス株式会社 | 白色発光有機エレクトロルミネッセンス素子 |
JP2004273128A (ja) * | 2003-03-05 | 2004-09-30 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子 |
JP4158562B2 (ja) * | 2003-03-12 | 2008-10-01 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
JP4506086B2 (ja) * | 2003-03-19 | 2010-07-21 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
JP2004311404A (ja) * | 2003-03-26 | 2004-11-04 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、照明装置および表示装置 |
JP4525190B2 (ja) * | 2003-06-09 | 2010-08-18 | 日立化成工業株式会社 | 金属配位化合物、ポリマー組成物、およびこれらを用いた有機エレクトロルミネセンス素子 |
JP4203732B2 (ja) * | 2003-06-12 | 2009-01-07 | ソニー株式会社 | 有機電界発光材料、有機電界発光素子および含複素環イリジウム錯体化合物 |
JP4891615B2 (ja) * | 2003-07-22 | 2012-03-07 | 出光興産株式会社 | 金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
JP4082297B2 (ja) * | 2003-07-29 | 2008-04-30 | 三菱化学株式会社 | 有機化合物、電荷輸送材料、有機電界発光素子材料および有機電界発光素子 |
JP4198654B2 (ja) * | 2003-08-07 | 2008-12-17 | 三星エスディアイ株式会社 | イリジウム化合物及びそれを採用した有機電界発光素子 |
JP4337475B2 (ja) * | 2003-08-27 | 2009-09-30 | 三菱化学株式会社 | 有機金属錯体、発光材料、および有機電界発光素子 |
CN100335462C (zh) * | 2003-09-05 | 2007-09-05 | 清华大学 | 咔唑衍生物及其在电致发光器件中的应用 |
TWI245068B (en) * | 2003-11-18 | 2005-12-11 | Chi Mei Optoelectronics Corp | Iridium complex as light emitting material and organic light emitting diode device |
JP2005169227A (ja) * | 2003-12-10 | 2005-06-30 | Showa Aircraft Ind Co Ltd | 溶剤回収装置 |
US20060008670A1 (en) * | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
US7504657B2 (en) | 2004-07-23 | 2009-03-17 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display and illuminator |
WO2006132012A1 (ja) * | 2005-06-09 | 2006-12-14 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
-
2006
- 2006-03-03 WO PCT/JP2006/304064 patent/WO2006132012A1/ja active Application Filing
- 2006-03-03 GB GB1104120A patent/GB2476003B/en active Active
- 2006-03-03 JP JP2007520029A patent/JPWO2006132012A1/ja active Pending
- 2006-03-03 GB GB0723474A patent/GB2442885B/en active Active
- 2006-06-01 US US11/444,590 patent/US8808874B2/en active Active
-
2010
- 2010-12-07 US US12/961,703 patent/US8728633B2/en active Active
- 2010-12-10 US US12/964,738 patent/US9428687B2/en active Active
-
2011
- 2011-12-08 JP JP2011268592A patent/JP5790463B2/ja active Active
- 2011-12-08 JP JP2011268590A patent/JP2012109575A/ja active Pending
-
2012
- 2012-12-03 JP JP2012264325A patent/JP5733294B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
US20060280966A1 (en) | 2006-12-14 |
JPWO2006132012A1 (ja) | 2009-01-08 |
JP2012109576A (ja) | 2012-06-07 |
JP5790463B2 (ja) | 2015-10-07 |
GB2442885B (en) | 2011-07-13 |
JP2013102165A (ja) | 2013-05-23 |
GB2476003B (en) | 2011-09-14 |
US9428687B2 (en) | 2016-08-30 |
GB201104120D0 (en) | 2011-04-27 |
GB2442885A (en) | 2008-04-16 |
US8728633B2 (en) | 2014-05-20 |
GB0723474D0 (en) | 2008-01-09 |
JP2012109575A (ja) | 2012-06-07 |
WO2006132012A1 (ja) | 2006-12-14 |
US20110073851A1 (en) | 2011-03-31 |
US20110073850A1 (en) | 2011-03-31 |
US8808874B2 (en) | 2014-08-19 |
GB2476003A (en) | 2011-06-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5733294B2 (ja) | 有機エレクトロルミネッセンス素子 | |
JP5741636B2 (ja) | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 | |
JP5594384B2 (ja) | 有機エレクトロルミネッセンス素子、表示装置および照明装置 | |
JP5679017B2 (ja) | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 | |
JP4887731B2 (ja) | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 | |
JP5273052B2 (ja) | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 | |
JP4626613B2 (ja) | 有機エレクトロルミネッセンス素子 | |
JPWO2006082742A1 (ja) | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 | |
JP2006143845A (ja) | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 | |
JP2006120762A (ja) | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 | |
JP2006131783A (ja) | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 | |
JP5055689B2 (ja) | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置および表示装置 | |
JP2006131782A (ja) | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 | |
JP2006080271A (ja) | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 | |
JP5040062B2 (ja) | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 | |
JP2006156635A (ja) | 有機エレクトロルミネッセンス素子及び表示装置 | |
JP2005317314A (ja) | 有機エレクトロルミネッセンス素子、照明装置および表示装置 | |
JP4968392B2 (ja) | 有機エレクトロルミネッセンス素子及び表示装置 | |
JP4900521B2 (ja) | 有機エレクトロルミネッセンス素子及び表示装置 | |
JP6112166B2 (ja) | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20131120 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131210 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140203 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140902 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150317 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150330 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5733294 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |