JPH1072579A - Luminescent material for organic electroluminescent element - Google Patents
Luminescent material for organic electroluminescent elementInfo
- Publication number
- JPH1072579A JPH1072579A JP8244491A JP24449196A JPH1072579A JP H1072579 A JPH1072579 A JP H1072579A JP 8244491 A JP8244491 A JP 8244491A JP 24449196 A JP24449196 A JP 24449196A JP H1072579 A JPH1072579 A JP H1072579A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- group
- unsubstituted
- general formula
- organic
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 68
- 125000003118 aryl group Chemical group 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 238000005401 electroluminescence Methods 0.000 claims description 60
- -1 C = O Inorganic materials 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000010410 layer Substances 0.000 abstract description 69
- 238000002347 injection Methods 0.000 abstract description 37
- 239000007924 injection Substances 0.000 abstract description 37
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 10
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 4
- 230000005525 hole transport Effects 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000002356 single layer Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 41
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 8
- 239000000758 substrate Substances 0.000 description 8
- 239000010409 thin film Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 229910052733 gallium Inorganic materials 0.000 description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 description 3
- MUNFOTHAFHGRIM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-oxadiazole Chemical compound C1=CC=C2C(C3=NN=C(O3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MUNFOTHAFHGRIM-UHFFFAOYSA-N 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229910000861 Mg alloy Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 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 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000013365 molecular weight analysis method Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- QLDRRLPJXGEMNS-UHFFFAOYSA-N 9,10-diiodoanthracene Chemical compound C1=CC=C2C(I)=C(C=CC=C3)C3=C(I)C2=C1 QLDRRLPJXGEMNS-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004697 chelate complex Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 125000005156 substituted alkylene group Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- BSHSCWRTJSBWLY-UHFFFAOYSA-N 1-cyclohexyl-4-phenylbenzene Chemical group C1CCCCC1C1=CC=C(C=2C=CC=CC=2)C=C1 BSHSCWRTJSBWLY-UHFFFAOYSA-N 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- GUPMCMZMDAGSPF-UHFFFAOYSA-N 1-phenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1[C](C=C[CH2])C1=CC=CC=C1 GUPMCMZMDAGSPF-UHFFFAOYSA-N 0.000 description 1
- NLXDFCLCNCWKND-UHFFFAOYSA-N 10-n-(4-butylphenyl)phenanthrene-9,10-diamine Chemical compound C1=CC(CCCC)=CC=C1NC1=C(N)C2=CC=CC=C2C2=CC=CC=C12 NLXDFCLCNCWKND-UHFFFAOYSA-N 0.000 description 1
- NIDFGXDXQKPZMA-UHFFFAOYSA-N 14h-benz[4,5]isoquino[2,1-a]perimidin-14-one Chemical compound C1=CC(N2C(=O)C=3C4=C(C2=N2)C=CC=C4C=CC=3)=C3C2=CC=CC3=C1 NIDFGXDXQKPZMA-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- PQYIVUDIIIJJDM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-thiadiazole Chemical compound C1=CC=C2C(C3=NN=C(S3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 PQYIVUDIIIJJDM-UHFFFAOYSA-N 0.000 description 1
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 1
- CKZLPIIZKXDBNM-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid naphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=CC2=C1.C1=CC=C(C(O)=O)C2=NC(C)=CC=C21.C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 CKZLPIIZKXDBNM-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- CGOZKBULMOZKHE-UHFFFAOYSA-N 2H-pyran 2H-thiopyran Chemical compound S1CC=CC=C1.O1CC=CC=C1 CGOZKBULMOZKHE-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- MWKLOMOIKCPLOY-UHFFFAOYSA-N 3,5-dinaphthalen-1-yl-1h-1,2,4-triazole Chemical compound C1=CC=C2C(C3=NN=C(N3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MWKLOMOIKCPLOY-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- RIERSGULWXEJKL-UHFFFAOYSA-N 3-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(O)C=CC=C1C(O)=O RIERSGULWXEJKL-UHFFFAOYSA-N 0.000 description 1
- UAPNUNDZDVNTDQ-UHFFFAOYSA-N 4,5-diphenyl-1,2,3-triazole Chemical compound C1=CC=CC=C1C1=NNN=C1C1=CC=CC=C1 UAPNUNDZDVNTDQ-UHFFFAOYSA-N 0.000 description 1
- YOPJQOLALJLPBS-UHFFFAOYSA-N 4,5-diphenyloxadiazole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)ON=N1 YOPJQOLALJLPBS-UHFFFAOYSA-N 0.000 description 1
- QVGVWLHVMVQIQI-UHFFFAOYSA-N 4,5-diphenylthiadiazole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)SN=N1 QVGVWLHVMVQIQI-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MERYTWSEJJITMM-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-[4-(4-phenylcyclohexyl)phenyl]aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1CCC(CC1)C=1C=CC=CC=1)C1=CC=C(C)C=C1 MERYTWSEJJITMM-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- VESMRDNBVZOIEN-UHFFFAOYSA-N 9h-carbazole-1,2-diamine Chemical compound C1=CC=C2C3=CC=C(N)C(N)=C3NC2=C1 VESMRDNBVZOIEN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 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
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 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
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LBGCRGLFTKVXDZ-UHFFFAOYSA-M ac1mc2aw Chemical compound [Al+3].[Cl-].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LBGCRGLFTKVXDZ-UHFFFAOYSA-M 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- CRZCUKCOUAZREG-UHFFFAOYSA-K aluminum;naphthalen-1-olate Chemical compound [Al+3].C1=CC=C2C([O-])=CC=CC2=C1.C1=CC=C2C([O-])=CC=CC2=C1.C1=CC=C2C([O-])=CC=CC2=C1 CRZCUKCOUAZREG-UHFFFAOYSA-K 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzoquinoline Natural products C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 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
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 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
- 150000007857 hydrazones Chemical class 0.000 description 1
- NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YERRTOUSFSZICJ-UHFFFAOYSA-N methyl 2-amino-2-(4-bromophenyl)acetate Chemical compound COC(=O)C(N)C1=CC=C(Br)C=C1 YERRTOUSFSZICJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 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 1
- 239000003921 oil Substances 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229940031826 phenolate Drugs 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide 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
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 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
- 239000011241 protective layer Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000001308 synthesis method Methods 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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical class C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 125000005033 thiopyranyl group Chemical group 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Luminescent Compositions (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は平面光源や表示に使用さ
れる有機エレクトロルミネッセンス（ＥＬ）素子用発光
材料および高輝度の発光素子に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a light emitting material for an organic electroluminescence (EL) device used for a flat light source or display and a light emitting device having a high luminance.
【０００２】[0002]
【従来の技術】有機物質を使用したＥＬ素子は、固体発
光型の安価な大面積フルカラー表示素子としての用途が
有望視され、多くの開発が行われている。一般にＥＬ
は、発光層および該層をはさんだ一対の対向電極から構
成されている。発光は、両電極間に電界が印加される
と、陰極側から電子が注入され、陽極側から正孔が注入
される。さらに、この電子が発光層において正孔と再結
合し、エネルギー準位が伝導帯から価電子帯に戻る際に
エネルギーを光として放出する現象である。2. Description of the Related Art An EL device using an organic substance is expected to be used as an inexpensive, large-area, full-color display device of a solid light emitting type, and many developments have been made. Generally EL
Is composed of a light-emitting layer and a pair of opposed electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons are recombined with holes in the light emitting layer, and energy is emitted as light when the energy level returns from the conduction band to the valence band.
【０００３】従来の有機ＥＬ素子は、無機ＥＬ素子に比
べて駆動電圧が高く、発光輝度や発光効率も低かった。
また、特性劣化も著しく実用化には至っていなかった。
近年、１０Ｖ以下の低電圧で発光する高い蛍光量子効率
を持った有機化合物を含有した薄膜を積層した有機ＥＬ
素子が報告され、関心を集めている（アプライド・フィ
ジクス・レターズ、５１巻、９１３ページ、１９８７年
参照）。この方法は、金属キレート錯体を発光層、アミ
ン系化合物を正孔注入層に使用して、高輝度の緑色発光
を得ており、６〜７Ｖの直流電圧で輝度は数１００ｃｄ
／ｍ2 、最大発光効率は１．５ｌｍ／Ｗを達成して、実
用領域に近い性能を持っている。[0003] Conventional organic EL devices have a higher driving voltage and lower luminous brightness and luminous efficiency than inorganic EL devices.
In addition, the characteristic deterioration was remarkable, and it had not been put to practical use.
2. Description of the Related Art In recent years, an organic EL in which a thin film containing an organic compound having high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less is laminated.
Devices have been reported and are of interest (see Applied Physics Letters, vol. 51, p. 913, 1987). This method uses a metal chelate complex for a light emitting layer and an amine compound for a hole injection layer to obtain high-luminance green light emission. The luminance is several hundred cd at a DC voltage of 6 to 7 V.
/ M 2 , and a maximum luminous efficiency of 1.5 lm / W, which is close to the practical range.
【０００４】しかしながら、現在までの有機ＥＬ素子
は、構成の改善により発光強度は改良されているが、未
だ充分な発光輝度は有していない。また、繰り返し使用
時の安定性に劣るという大きな問題を持っている。これ
は、例えば、トリス（８−ヒドロキシキノリナート）ア
ルミニウム錯体等の金属キレート錯体が、電界発光時に
化学的に不安定であり、陰極との密着性も悪く、短時間
の発光で大きく劣化していた。以上の理由により、大き
な発光輝度を持ち、繰り返し使用時での安定性の優れた
有機ＥＬ素子の開発のために、優れた発光能力を有し、
耐久性のある発光材料の開発が望まれている。[0004] However, organic EL devices up to now have improved luminous intensity due to the improved structure, but do not yet have sufficient luminous brightness. In addition, there is a major problem that the stability upon repeated use is poor. This is because, for example, a metal chelate complex such as a tris (8-hydroxyquinolinato) aluminum complex is chemically unstable during electroluminescence, has poor adhesion to a cathode, and is greatly deteriorated by short-time light emission. I was For the above reasons, for the development of an organic EL device having a large light emission luminance and excellent stability in repeated use, it has an excellent light emission ability,
The development of a durable light-emitting material is desired.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、発光輝度が
高く、繰り返し使用時での安定性の優れた有機ＥＬ素子
の提供にある。本発明者らが鋭意検討した結果、下記一
般式で示される有機ＥＬ素子用発光材料を発光層に使用
した有機ＥＬ素子の発光輝度が高く、繰り返し使用時で
の安定性も優れていることを見いだし本発明を成すに至
った。SUMMARY OF THE INVENTION An object of the present invention is to provide an organic EL device having a high emission luminance and excellent stability when used repeatedly. As a result of extensive studies by the present inventors, it has been found that the organic EL device using the light emitting material for an organic EL device represented by the following general formula for the light emitting layer has a high light emission luminance and excellent stability in repeated use. The inventors have found the present invention.
【０００６】[0006]
【課題を解決するための手段】本発明は、下記一般式
［１］で示される有機エレクトロルミネッセンス素子用
発光材料に関する。 一般式［１］The present invention relates to a luminescent material for an organic electroluminescence device represented by the following general formula [1]. General formula [1]
【０００７】[0007]
【化６】 Embedded image
【０００８】［式中、Ａ1 〜Ａ4 は、置換もしくは未置
換の炭素数６〜１６のアリール基を表す。Ｒ1 〜Ｒ
8 は、それぞれ独立に、水素原子、ハロゲン原子、置換
もしくは未置換のアルキル基、置換もしくは未置換のア
ルコキシ基、置換もしくは未置換のアリール基、置換も
しくは未置換のアミノ基を表す（隣接した置換基同志で
結合して新たな６員アリール環を形成してもよ
い。）。］[Wherein, A 1 to A 4 represent a substituted or unsubstituted aryl group having 6 to 16 carbon atoms. R 1 to R
8 independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group (neighboring substituted Groups may be joined together to form a new 6-membered aryl ring.). ]
【０００９】さらに本発明は、下記一般式［２］で示さ
れる有機エレクトロルミネッセンス素子用発光材料であ
る。 一般式［２］Further, the present invention is a light emitting material for an organic electroluminescence device represented by the following general formula [2]. General formula [2]
【００１０】[0010]
【化７】 Embedded image
【００１１】［式中、Ｒ1 〜Ｒ28は、それぞれ独立に、
水素原子、ハロゲン原子、置換もしくは未置換のアルキ
ル基、置換もしくは未置換のアルコキシ基、置換もしく
は未置換のアリール基、置換もしくは未置換のアミノ基
を表す。Ｒ1〜Ｒ4もしくはＲ5〜Ｒ8は隣接した置換基同
志で結合して新たな６員アリール環を形成してもよ
い。］Wherein R 1 to R 28 are each independently
A hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted amino group. R 1 to R 4 or R 5 to R 8 may be bonded by adjacent substituents to form a new 6-membered aryl ring. ]
【００１２】さらに本発明は、下記一般式［３］で示さ
れる有機エレクトロルミネッセンス素子用発光材料であ
る。 一般式［３］Further, the present invention is a light emitting material for an organic electroluminescence device represented by the following general formula [3]. General formula [3]
【００１３】[0013]
【化８】 Embedded image
【００１４】［式中、Ｒ1 〜Ｒ8 およびＲ29〜Ｒ48は、
それぞれ独立に、水素原子、ハロゲン原子、置換もしく
は未置換のアルキル基、置換もしくは未置換のアルコキ
シ基、置換もしくは未置換のアリール基、置換もしくは
未置換のアミノ基を表す。Ｘ1〜Ｘ4 は、それぞれ独立
に、Ｏ、Ｓ、Ｃ＝Ｏ、ＳＯ2 、（ＣＨ2 ）ｘ−Ｏ−（Ｃ
Ｈ2 ）ｙ、置換もしくは未置換のアルキレン基、置換も
しくは未置換の脂肪族環残基を表す。ここで、ｘおよび
ｙは、それぞれ独立に、０〜２０の正の整数を表すが、
ｘ＋ｙ＝０となることはない。Ｒ1〜Ｒ4もしくはＲ5〜
Ｒ8は隣接した置換基同志で結合して新たな６員アリー
ル環を形成してもよい。］Wherein R 1 to R 8 and R 29 to R 48 are
Each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted amino group. X 1 to X 4 are each independently O, S, C ＝ O, SO 2 , (CH 2 ) x-O- (C
H 2 ) y represents a substituted or unsubstituted alkylene group or a substituted or unsubstituted aliphatic ring residue. Here, x and y each independently represent a positive integer of 0 to 20,
x + y = 0 never occurs. R 1 to R 4 or R 5 to
R 8 may be linked by adjacent substituents to form a new 6-membered aryl ring. ]
【００１５】さらに本発明は、下記一般式［４］で示さ
れる有機エレクトロルミネッセンス素子用発光材料であ
る。 一般式［４］Further, the present invention is a light emitting material for an organic electroluminescence device represented by the following general formula [4]. General formula [4]
【００１６】[0016]
【化９】 Embedded image
【００１７】［式中、Ｒ1 〜Ｒ8 およびＲ29〜Ｒ48は、
それぞれ独立に、水素原子、ハロゲン原子、置換もしく
は未置換のアルキル基、置換もしくは未置換のアルコキ
シ基、置換もしくは未置換のアリール基、置換もしくは
未置換のアミノ基を表す。Ｘ1〜Ｘ4 は、それぞれ独立
に、Ｏ、Ｓ、Ｃ＝Ｏ、ＳＯ2 、（ＣＨ2 ）ｘ−Ｏ−（Ｃ
Ｈ2 ）ｙ、置換もしくは未置換のアルキレン基、置換も
しくは未置換の脂肪族環残基を表す。ここで、ｘおよび
ｙは、それぞれ独立に、０〜２０の正の整数を表すが、
ｘ＋ｙ＝０となることはない。Ｒ1〜Ｒ4もしくはＲ5〜
Ｒ8は隣接した置換基同志で結合して新たな６員アリー
ル環を形成してもよい。］Wherein R 1 to R 8 and R 29 to R 48 are
Each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted amino group. X 1 to X 4 are each independently O, S, C ＝ O, SO 2 , (CH 2 ) x-O- (C
H 2 ) y represents a substituted or unsubstituted alkylene group or a substituted or unsubstituted aliphatic ring residue. Here, x and y each independently represent a positive integer of 0 to 20,
x + y = 0 never occurs. R 1 to R 4 or R 5 to
R 8 may be linked by adjacent substituents to form a new 6-membered aryl ring. ]
【００１８】さらに本発明は、下記一般式［５］で示さ
れる有機エレクトロルミネッセンス素子用発光材料であ
る。 一般式［５］Further, the present invention is a light emitting material for an organic electroluminescence device represented by the following general formula [5]. General formula [5]
【００１９】[0019]
【化１０】 Embedded image
【００２０】［式中、Ｒ1 〜Ｒ8 およびＲ29〜Ｒ48は、
それぞれ独立に、水素原子、ハロゲン原子、置換もしく
は未置換のアルキル基、置換もしくは未置換のアルコキ
シ基、置換もしくは未置換のアリール基、置換もしくは
未置換のアミノ基を表す。Ｙ1〜Ｙ8 は、置換もしくは
未置換の炭素数１〜２０のアルキル基、置換もしくは未
置換の炭素数６〜１６のアリール基を表す。Ｒ1〜Ｒ4も
しくはＲ5〜Ｒ8は隣接した置換基同志で結合して新たな
６員アリール環を形成してもよい。］Wherein R 1 to R 8 and R 29 to R 48 are
Each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted amino group. Y 1 to Y 8 represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and a substituted or unsubstituted aryl group having 6 to 16 carbon atoms. R 1 to R 4 or R 5 to R 8 may be bonded by adjacent substituents to form a new 6-membered aryl ring. ]
【００２１】さらに本発明は、一対の電極間に発光層も
しくは発光層を含む複数層の有機化合物薄膜層を備えた
有機エレクトロルミネッセンス素子において、発光層が
上記有機エレクトロルミネッセンス素子用発光材料を含
有する層である有機エレクトロルミネッセンス素子であ
る。Further, the present invention provides an organic electroluminescence device having a light emitting layer or a plurality of organic compound thin film layers including the light emitting layer between a pair of electrodes, wherein the light emitting layer contains the light emitting material for an organic electroluminescent device. The organic electroluminescent device is a layer.
【００２２】さらに本発明は、芳香族三級アミン誘導体
もしくはフタロシアニン誘導体を含有する層を、発光層
と陽極との間に形成してなる上記有機エレクトロルミネ
ッセンス素子である。Further, the present invention is the above-mentioned organic electroluminescence device, wherein a layer containing an aromatic tertiary amine derivative or a phthalocyanine derivative is formed between the light emitting layer and the anode.
【００２３】さらに本発明は、金属錯体化合物もしくは
含窒素五員環誘導体を含有する層を、発光層と陰極との
間に形成してなる上記有機エレクトロルミネッセンス素
子である。Furthermore, the present invention is the above-mentioned organic electroluminescence device, wherein a layer containing a metal complex compound or a nitrogen-containing five-membered ring derivative is formed between the light-emitting layer and the cathode.
【００２４】[0024]
【００２５】本発明における一般式［１］で示される化
合物のＡ1 〜Ａ4 における置換もしくは未置換の炭素数
６〜１６のアリール基としては、フェニル基、ビフェニ
ル基、ターフェニル基、ナフチル基、アントリル基、フ
ェナントリル基、フルオレニル基、ピレニル基等のアリ
ール基であり、それぞれのアリール基は置換基を有して
いても良い。本発明においてアリール基の芳香族炭素原
子は窒素原子、酸素原子およびまたは硫黄原子により置
換されていてもよい。このような、異種原子を含むアリ
ール基としては、例えばフラニル基、チオフェニル基、
ピロニル基、ピリジン基等がある。又、Ａ1 とＡ2 また
はＡ3 とＡ4 とが一体となってカルバゾール基のような
窒素原子を含むアリール基を形成してもよい。The substituted or unsubstituted aryl group having 6 to 16 carbon atoms in A 1 to A 4 of the compound represented by the general formula [1] in the present invention includes a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group. , Anthryl group, phenanthryl group, fluorenyl group, pyrenyl group and the like, and each aryl group may have a substituent. In the present invention, the aromatic carbon atom of the aryl group may be substituted by a nitrogen atom, an oxygen atom and / or a sulfur atom. Examples of such an aryl group containing a heteroatom include a furanyl group, a thiophenyl group,
Examples include a pyronyl group and a pyridine group. Further, A 1 and A 2 or A 3 and A 4 may be combined to form an aryl group containing a nitrogen atom such as a carbazole group.
【００２６】本発明における一般式［１］〜［５］で示
される化合物のＲ1 〜Ｒ48は、それぞれ独立に、水素原
子、ハロゲン原子、置換もしくは未置換のアルキル基、
置換もしくは未置換のアルコキシ基、置換もしくは未置
換のアリール基、置換もしくは未置換のアミノ基を表
す。Ａ1 〜Ａ4 の有する置換基、およびＲ1 〜Ｒ48の具
体例は、ハロゲン原子としては弗素、塩素、臭素、ヨウ
素であり、置換もしくは未置換のアルキル基としては、
メチル基、エチル基、プロピル基、ブチル基、ｓｅｃ−
ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル
基、ヘプチル基、オクチル基、ステアリル基等の炭素数
１〜２０の未置換直鎖状又は分枝状アルキル基の他、２
−フェニルイソプロピル基、トリクロロメチル基、トリ
フルオロメチル基、ベンジル基、α−フェノキシベンジ
ル基、α，α−ジメチルベンジル基、α，α−メチルフ
ェニルベンジル基、α，α−ジトリフルオロメチルベン
ジル基、トリフェニルメチル基、α−ベンジルオキシベ
ンジル基等の炭素数１〜２０のアルキル基の置換体があ
り、置換もしくは未置換のアルコキシル基としては、メ
トキシ基、エトキシ基、プロポキシ基、ｎ−ブトキシ
基、ｔ−ブトキシ基、ｎ−オクチルオキシ基、ｔ−オク
チルオキシ基等の炭素数１〜２０の未置換アルコキシル
基の他、１，１，１−テトラフルオロエトキシ基、フェ
ノキシ基、ベンジルオキシ基、オクチルフェノキシ基等
の炭素数１〜２０のアルコキシル基の置換体があり、置
換もしくは未置換のアリール基としては、フェニル基、
２−メチルフェニル基、３−メチルフェニル基、４−メ
チルフェニル基、４−エチルフェニル基、ビフェニル
基、４−メチルビフェニル基、４−エチルビフェニル
基、４−シクロヘキシルビフェニル基、ターフェニル
基、３，５−ジクロロフェニル基、ナフチル基、５−メ
チルナフチル基、アントリル基、ピレニル基等の芳香族
炭素数６〜１８の置換もしくは未置換のアリール基があ
り、窒素原子、酸素原子およびまたは硫黄原子により芳
香族炭素原子が置換されていてもよいアリール基として
は、フラニル基、チオフェニル基、ピロール基、ピラニ
ル基、チオピラニル基、ピリジニル基、チアゾリル基、
イミダゾール基、ピリミジニル基、ピリジニル基、トリ
アジニル基、インドリニル基、キノリル基、プリニル基
等があり、置換もしくは未置換のアミノ基としては、ア
ミノ基、ジメチルアミノ基、ジエチルアミノ基等のジア
ルキルアミノ基、フェニルメチルアミノ基、ジフェニル
アミノ基、ジトリルアミノ基、ジベンジルアミノ基等が
ある。また、隣接する置換基同士で、それぞれ互いに結
合して、フェニル基、ナフチル基、アントリル基、ピレ
ニル基等を形成しても良い。In the present invention, R 1 to R 48 of the compounds represented by the general formulas [1] to [5] each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group,
Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted amino group. Specific examples of the substituents of A 1 to A 4 and R 1 to R 48 include fluorine, chlorine, bromine and iodine as the halogen atom, and a substituted or unsubstituted alkyl group as the halogen atom.
Methyl group, ethyl group, propyl group, butyl group, sec-
An unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms such as a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group and a stearyl group;
-Phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α, α-ditrifluoromethylbenzyl group, There are substituents of alkyl groups having 1 to 20 carbon atoms such as triphenylmethyl group and α-benzyloxybenzyl group, and substituted or unsubstituted alkoxyl groups include methoxy group, ethoxy group, propoxy group and n-butoxy group. , A t-butoxy group, an n-octyloxy group, an unsubstituted alkoxyl group having 1 to 20 carbon atoms such as a t-octyloxy group, a 1,1,1-tetrafluoroethoxy group, a phenoxy group, a benzyloxy group, There is a substituted or unsubstituted aryl having an alkoxyl group having 1 to 20 carbon atoms such as an octylphenoxy group. Phenyl group,
2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, terphenyl group, 3 , 5-dichlorophenyl, naphthyl, 5-methylnaphthyl, anthryl, pyrenyl and the like, and substituted or unsubstituted aryl groups having 6 to 18 aromatic carbon atoms, and are represented by nitrogen atom, oxygen atom and / or sulfur atom. The aryl group which may be substituted with an aromatic carbon atom includes a furanyl group, a thiophenyl group, a pyrrole group, a pyranyl group, a thiopyranyl group, a pyridinyl group, a thiazolyl group,
There are imidazole group, pyrimidinyl group, pyridinyl group, triazinyl group, indolinyl group, quinolyl group, purinyl group, etc., and substituted or unsubstituted amino groups include amino group, dimethylamino group, dialkylamino group such as diethylamino group, Examples include a methylamino group, a diphenylamino group, a ditolylamino group, and a dibenzylamino group. Adjacent substituents may be bonded to each other to form a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, or the like.
【００２７】本発明における一般式［３］および［４］
で示される化合物のＸ1 〜Ｘ4 は、それぞれ独立に、
Ｏ、Ｓ、Ｃ＝Ｏ、ＳＯ2 、（ＣＨ2 ）ｘ−Ｏ−（Ｃ
Ｈ2 ）ｙ、置換もしくは未置換のアルキレン基、置換も
しくは未置換の脂肪族環残基を表す。ここで、ｘおよび
ｙは、それぞれ特立に、０〜２０の正の整数を表すが、
ｘ＋ｙ＝０となることはない。置換または未置換のアル
キレン基としては炭素数１〜２０のアルキレン基もしく
はその置換体、置換または未置換の脂肪族環残基として
は、シクロペンチル環、シクロヘキシル環、４−メチル
シクロヘキシル環、シクロヘプチル環等の炭素数５〜７
の脂肪族環の二価の残基が挙げられる。Ｘ1〜Ｘ4の置換
アルキレン基又は置換脂肪族環残基の置換基としてはＲ
1〜Ｒ4 8で示した置換基がある。Ｘ1〜Ｘ4の置換アルキ
レン基として好ましいものは、２−フェニルイソプロピ
レン基、ジクロロメチレン基、ジフルオロメチレン基、
ベンジレン基、α−フェノキシベンジレン基、α，α−
ジメチルベンジレン基、α，α−メチルフェニルベンジ
レン基、ジフェニルメチレン基、α−ベンジルオキシベ
ンジレン基などが挙げられる。The general formulas [3] and [4] in the present invention
X 1 to X 4 of the compound represented by are each independently
O, S, C = O, SO 2, (CH 2) x-O- (C
H 2 ) y represents a substituted or unsubstituted alkylene group or a substituted or unsubstituted aliphatic ring residue. Here, x and y each independently represent a positive integer of 0 to 20,
x + y = 0 never occurs. As a substituted or unsubstituted alkylene group, an alkylene group having 1 to 20 carbon atoms or a substituted product thereof, and as a substituted or unsubstituted aliphatic ring residue, a cyclopentyl ring, a cyclohexyl ring, a 4-methylcyclohexyl ring, a cycloheptyl ring 5-7 carbon atoms such as
And a divalent residue of an aliphatic ring. The substituent of the substituted alkylene group or the substituted aliphatic ring residue of X 1 to X 4 is R
It is a substituent shown in 1 to R 4 8. Preferred as the substituted alkylene group for X 1 to X 4 are a 2-phenylisopropylene group, a dichloromethylene group, a difluoromethylene group,
Benzylene group, α-phenoxybenzylene group, α, α-
Examples thereof include a dimethylbenzylene group, an α, α-methylphenylbenzylene group, a diphenylmethylene group, and an α-benzyloxybenzylene group.
【００２８】本発明における一般式［５］で示される化
合物のＹ1 〜Ｙ8 は、置換もしくは未置換の炭素数１〜
２０のアルキル基、置換もしくは未置換の炭素数６〜１
６のアリール基を表す。アルキル基およびアリール基の
具体例は、前記のＲ1 〜Ｒ48で記述したアルキル基およ
びアリール基が挙げられる。In the present invention, Y 1 to Y 8 of the compound represented by the general formula [5] may be substituted or unsubstituted having 1 to 1 carbon atoms.
20 alkyl groups, substituted or unsubstituted 6-1 carbon atoms
6 represents an aryl group. Specific examples of the alkyl group and the aryl group include the alkyl groups and the aryl groups described for R 1 to R 48 above.
【００２９】この化合物の中で、一般式［３］〜［５］
で表されるような芳香族環を有している置換基を持つ化
合物、もしくは一般式［１］〜［５］のＲ1 〜Ｒ48の隣
接する置換基同士で芳香族環を形成している化合物は、
ガラス転移点や融点が高くなり電界発光時における有機
層中、有機層間もしくは、有機層と金属電極間で発生す
るジュール熱に対する耐性（耐熱性）が向上するので、
有機ＥＬ素子の発光材料として使用した場合、高い発光
輝度を示し、長時間発光させる際にも有利である。本発
明の化合物は、これらの置換基に限定されるものではな
い。Among these compounds, general formulas [3] to [5]
Or a compound having a substituent having an aromatic ring represented by the general formula [1] to [5], wherein adjacent substituents of R 1 to R 48 form an aromatic ring. Compounds are
Since the glass transition point and melting point increase, the resistance (heat resistance) to Joule heat generated in the organic layer, between the organic layers, or between the organic layer and the metal electrode during electroluminescence improves.
When used as a light-emitting material for an organic EL element, it exhibits high light emission luminance and is advantageous for long-term light emission. The compounds of the present invention are not limited to these substituents.
【００３０】以下に、本発明の一般式［１］〜［５］の
化合物の代表例を、表１に具体的に例示するが、本発明
は、この代表例に限定されるものではない。Hereinafter, typical examples of the compounds of the general formulas [1] to [5] of the present invention are specifically shown in Table 1, but the present invention is not limited to these typical examples.
【００３１】[0031]
【表１】 [Table 1]
【００３２】 [0032]
【００３３】 [0033]
【００３４】 [0034]
【００３５】 [0035]
【００３６】 [0036]
【００３７】 [0037]
【００３８】 [0038]
【００３９】 [0039]
【００４０】 [0040]
【００４１】 [0041]
【００４２】 [0042]
【００４３】本発明の一般式で示される化合物の合成方
法の一例を以下に示す。９，１０−ジハロゲノアントラ
セン、置換基を有しても良いジフェニルアミン誘導体、
炭酸カリウムおよび触媒を溶媒中で反応させるて、一般
式［１］の化合物を合成することができる。アントラセ
ン誘導体に代えてアントラキノン誘導体からも合成する
ことができる。炭酸カリウムに代えて、炭酸ナトリウ
ム、水酸化カリウム、水酸化ナトリウムまたはアンモニ
ア水等を使用することができる。触媒としては、銅紛、
塩化第一銅、スズ、塩化第一スズ、ピリジン、三塩化ア
ルミニウムまたは四塩化チタンがある。溶媒は、ベンゼ
ン、トルエンまたはキシレンがある。以上の合成法は、
限定されるものではない。An example of a method for synthesizing the compound represented by the general formula of the present invention is shown below. 9,10-dihalogenoanthracene, a diphenylamine derivative optionally having a substituent,
The compound of the general formula [1] can be synthesized by reacting potassium carbonate and a catalyst in a solvent. It can also be synthesized from an anthraquinone derivative instead of an anthracene derivative. Instead of potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, aqueous ammonia or the like can be used. Copper powder,
There are cuprous chloride, tin, stannous chloride, pyridine, aluminum trichloride or titanium tetrachloride. Solvents include benzene, toluene or xylene. The above synthesis method
It is not limited.
【００４４】本発明の一般式で示される化合物は、固体
状態において強い蛍光を持つ化合物であり電場発光性に
優れている。また、優れた正孔注入性や正孔輸送性も併
せて持ち合わせているので、正孔輸送型発光材料として
有効に使用することができ、他の正孔輸送性材料、電子
輸送性材料もしくはドーピング材料を使用してもさしつ
かえない。The compound represented by the general formula of the present invention has strong fluorescence in a solid state and has excellent electroluminescence. It also has excellent hole injecting and hole transporting properties, so it can be effectively used as a hole transporting luminescent material, and can be used for other hole transporting materials, electron transporting materials or doping. You can use materials.
【００４５】有機ＥＬ素子は、陽極と陰極間に一層もし
くは多層の有機薄膜を形成した素子である。一層型の場
合、陽極と陰極との間に発光層を設けている。発光層
は、発光材料を含有し、それに加えて陽極から注入した
正孔、もしくは陰極から注入した電子を発光材料まで輸
送させるために正孔注入材料もしくは電子注入材料を含
有しても良い。多層型は、（陽極／正孔注入層／発光層
／陰極）、（陽極／発光層／電子注入層／陰極）、（陽
極／正孔注入層／発光層／電子注入層／陰極）の多層構
成で積層した有機ＥＬ素子がある。一般式［１］の化合
物は、高い発光特性を持ち、正孔注入性、正孔輸送特性
をもっているので、正孔注入型発光材料として発光層に
使用できる。An organic EL device is a device in which a single or multilayer organic thin film is formed between an anode and a cathode. In the case of a single layer type, a light emitting layer is provided between an anode and a cathode. The light emitting layer contains a light emitting material and may further contain a hole injection material or an electron injection material for transporting holes injected from an anode or electrons injected from a cathode to the light emitting material. The multilayer type includes (anode / hole injection layer / electron injection layer / cathode), (anode / hole injection layer / electron injection layer / cathode), and (anode / hole injection layer / light emission layer / electron injection layer / cathode) multilayer. There is an organic EL element stacked in a configuration. Since the compound of the general formula [1] has high light-emitting properties, and has hole-injecting properties and hole-transporting properties, it can be used in a light-emitting layer as a hole-injecting light-emitting material.
【００４６】発光層には、必要があれば、本発明の一般
式の化合物に加えて、さらなる発光材料、発光補助材
料、正孔注入材料や電子注入材料を使用することもでき
る。有機ＥＬ素子は、多層構造にすることにより、クエ
ンチングによる輝度や寿命の低下を防ぐことができる。
必要があれば、発光材料、発光補助材料、正孔注入材料
や電子注入材料を組み合わせて使用することが出来る。
また、発光補助材料をドーピングして、発光輝度や発光
効率の向上、およびドーピング材料により赤色や青色の
発光を得ることもできる。また、正孔注入層、発光層、
電子注入層は、それぞれ二層以上の層構成により形成さ
れても良い。In the light emitting layer, if necessary, in addition to the compound of the general formula of the present invention, a further light emitting material, light emitting auxiliary material, hole injection material or electron injection material can be used. When the organic EL element has a multilayer structure, it is possible to prevent a decrease in luminance and life due to quenching.
If necessary, a combination of a light emitting material, a light emission auxiliary material, a hole injection material, and an electron injection material can be used.
In addition, doping with a light emission auxiliary material can improve light emission luminance and light emission efficiency, and can obtain red and blue light emission by the doping material. Also, a hole injection layer, a light emitting layer,
The electron injection layer may be formed with two or more layers.
【００４７】有機ＥＬ素子の陽極に使用される導電性材
料としては、４ｅＶより大きな仕事関数を持つものが適
しており、炭素、アルミニウム、バナジウム、鉄、コバ
ルト、ニッケル、タングステン、銀、金、白金、パラジ
ウム等およびそれらの合金、ＩＴＯ基板、ＮＥＳＡ基板
に使用される酸化スズ、酸化インジウム等の酸化金属、
さらにはポリチオフェンやポリピロール等の有機導電性
樹脂が用いられる。陰極に使用される導電性物質として
は、４ｅＶより小さな仕事関数を持つものが適してお
り、マグネシウム、カルシウム、錫、鉛、チタニウム、
イットリウム、リチウム、ルテニウム、マンガン等およ
びそれらの合金が用いられるが、これらに限定されるも
のではない。陽極および陰極は、必要があれば二層以上
の層構成により形成されていても良い。As the conductive material used for the anode of the organic EL device, those having a work function of more than 4 eV are suitable, and include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, and platinum. , Palladium and their alloys, tin oxide used for ITO substrate, NESA substrate, metal oxide such as indium oxide,
Further, an organic conductive resin such as polythiophene or polypyrrole is used. As the conductive material used for the cathode, those having a work function smaller than 4 eV are suitable, and magnesium, calcium, tin, lead, titanium,
Yttrium, lithium, ruthenium, manganese, and the like and alloys thereof are used, but are not limited thereto. The anode and the cathode may be formed by two or more layers if necessary.
【００４８】有機ＥＬ素子では、効率良く発光させるた
めに、少なくとも一方は素子の発光波長領域において充
分透明にすることが望ましい。また、基板も透明である
ことが望ましい。透明電極は、上記の導電性材料を使用
して、蒸着やスパッタリング等の方法で所定の透光性が
確保するように設定する。発光面の電極は、光透過率を
１０％以上にすることが望ましい。基板は、機械的、熱
的強度を有し、透明なものであれば限定されるものでは
ないが、例示すると、ガラス基板、ポリエチレン板、ポ
リエーテルサルフォン板、ポリプロピレン板等の透明樹
脂があげられる。In the organic EL device, it is desirable that at least one of the organic EL devices is sufficiently transparent in the emission wavelength region of the device in order to emit light efficiently. Further, it is desirable that the substrate is also transparent. The transparent electrode is set using the above-described conductive material so as to secure a predetermined translucency by a method such as vapor deposition or sputtering. The electrode on the light emitting surface desirably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and is transparent, but examples thereof include transparent resins such as a glass substrate, a polyethylene plate, a polyether sulfone plate, and a polypropylene plate. Can be
【００４９】本発明に係わる有機ＥＬ素子の各層の形成
は、真空蒸着、スパッタリング等の乾式成膜法やスピン
コーティング、ディッピング等の湿式成膜法のいずれの
方法を適用することができる。膜厚は特に限定されるも
のではないが、各層は適切な膜厚に設定する必要があ
る。膜厚が厚すぎると、一定の光出力を得るために大き
な印加電圧が必要になり効率が悪くなる。膜厚が薄すぎ
るとピンホール等が発生して、電界を印加しても充分な
発光輝度が得られない。通常の膜厚は５ｎｍから１０μ
ｍの範囲が好適であるが、１０ｎｍから０．２μｍの範
囲がさらに好ましい。Each layer of the organic EL device according to the present invention can be formed by any of dry film forming methods such as vacuum evaporation and sputtering and wet film forming methods such as spin coating and dipping. The thickness is not particularly limited, but each layer needs to be set to an appropriate thickness. If the film thickness is too large, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too small, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. Normal thickness is 5nm to 10μ
The range of m is suitable, but the range of 10 nm to 0.2 μm is more preferable.
【００５０】湿式成膜法の場合、各層を形成する材料
を、エタノール、クロロホルム、テトラヒドロフラン、
ジオキサン等の適切な溶媒に溶解または分散させて薄膜
を形成するが、その溶媒はいずれであっても良い。ま
た、いずれの有機薄膜層においても、成膜性向上、膜の
ピンホール防止等のため適切な樹脂や添加剤を使用して
も良い。使用の可能な樹脂としては、ポリスチレン、ポ
リカーボネート、ポリアリレート、ポリエステル、ポリ
アミド、ポリウレタン、ポリスルフォン、ポリメチルメ
タクリレート、ポリメチルアクリレート、セルロース等
の絶縁性樹脂、ポリ−Ｎ−ビニルカルバゾール、ポリシ
ラン等の光導電性樹脂、ポリチオフェン、ポリピロール
等の導電性樹脂を挙げることができる。また、添加剤と
しては、酸化防止剤、紫外線吸収剤、可塑剤等を挙げる
ことができる。In the case of the wet film forming method, the material forming each layer is made of ethanol, chloroform, tetrahydrofuran,
The thin film is formed by dissolving or dispersing in a suitable solvent such as dioxane, and any solvent may be used. In any of the organic thin film layers, a suitable resin or additive may be used for improving film forming properties, preventing pinholes in the film, and the like. Examples of usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose; and light-sensitive resins such as poly-N-vinyl carbazole and polysilane. Examples of the conductive resin include conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
【００５１】本有機ＥＬ素子は、発光層、正孔注入層、
電子注入層において、必要があれば公知の発光材料、発
光補助材料、正孔注入材料、電子注入材料を使用するこ
とができる。The present organic EL device has a light emitting layer, a hole injection layer,
In the electron injection layer, if necessary, a known light emitting material, light emission auxiliary material, hole injection material, and electron injection material can be used.
【００５２】本発明の一般式の化合物を発光層に使用で
きる発光材料またはドーピング材料としては、アントラ
セン、ナフタレン、フェナントレン、ピレン、テトラセ
ン、コロネン、クリセン、フルオレセイン、ペリレン、
フタロペリレン、ナフタロペリレン、ペリノン、フタロ
ペリノン、ナフタロペリノン、ジフェニルブタジエン、
テトラフェニルブタジエン、クマリン、オキサジアゾー
ル、アルダジン、ビスベンゾキサゾリン、ビススチリ
ル、ピラジン、シクロペンタジエン、キノリン金属錯
体、アミノキノリン金属錯体、ベンゾキノリン金属錯
体、イミン、ジフェニルエチレン、ビニルアントラセ
ン、ジアミノカルバゾール、ピラン、チオピラン、ポリ
メチン、メロシアニン、イミダゾールキレート化オキシ
ノイド化合物、キナクリドン、ルブレンおよび蛍光色素
等があるが、これらに限定されるものではない。The light emitting material or doping material which can use the compound of the general formula of the present invention in the light emitting layer includes anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene,
Phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene,
Tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran Thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compounds, quinacridone, rubrene, and fluorescent dyes, but are not limited thereto.
【００５３】正孔注入材料としては、正孔を輸送する能
力を持ち、陽極からの正孔注入効果、発光層または発光
材料に対して優れた正孔注入効果を有し、発光層で生成
した励起子の電子注入層または電子注入材料への移動を
防止し、かつ薄膜形成能力の優れた化合物が挙げられ
る。具体的には、フタロシアニン誘導体、ナフタロシア
ニン誘導体、ポルフィリン誘導体、オキサゾール、オキ
サジアゾール、トリアゾール、イミダゾール、イミダゾ
ロン、イミダゾールチオン、ピラゾリン、ピラゾロン、
テトラヒドロイミダゾール、オキサゾール、オキサジア
ゾール、ヒドラゾン、アシルヒドラゾン、ポリアリール
アルカン、スチルベン、ブタジエン、ベンジジン型トリ
フェニルアミン、スチリルアミン型トリフェニルアミ
ン、ジアミン型トリフェニルアミン等と、それらの誘導
体、およびポリビニルカルバゾール、ポリシラン、導電
性高分子等の高分子材料等があるが、これらに限定され
るものではない。The hole injecting material has the ability to transport holes, has the effect of injecting holes from the anode, and has an excellent hole injecting effect on the light emitting layer or the light emitting material. Compounds that prevent excitons from migrating to the electron injection layer or the electron injection material and have excellent thin film forming ability are exemplified. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone,
Tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine, and derivatives thereof, and polyvinyl carbazole , Polysilane, and a polymer material such as a conductive polymer, but are not limited thereto.
【００５４】本発明の有機ＥＬ素子において、さらに効
果的な正孔注入材料は、芳香族三級アミン誘導体もしく
はフタロシアニン誘導体である。具体的には、芳香族三
級アミン誘導体としては、トリフェニルアミン、トリト
リルアミン、トリルジフェニルアミン、Ｎ，Ｎ’−ジフ
ェニル−Ｎ，Ｎ’−（３−メチルフェニル）−１，１’
−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ，Ｎ’Ｎ’
−（４−メチルフェニル）−１，１’−フェニル−４，
４’−ジアミン、Ｎ，Ｎ，Ｎ’Ｎ’−（４−メチルフェ
ニル）−１，１’−ビフェニル−４，４’−ジアミン、
Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジナフチル−１，
１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ’−
（メチルフェニル）−Ｎ，Ｎ’−（４−ｎ−ブチルフェ
ニル）−フェナントレン−９，１０−ジアミン、Ｎ，Ｎ
−ビス（４−ジ−４−トリルアミノフェニル）−４−フ
ェニル−シクロヘキサン等、もしくはこれらの芳香族三
級アミン骨格を有したオリゴマーもしくはポリマー等が
あるが、これらに限定されるものではない。フタロシア
ニン（Ｐｃ）誘導体としては、Ｈ2 Ｐｃ、ＣｕＰｃ、Ｃ
ｏＰｃ、ＮｉＰｃ、ＺｎＰｃ、ＰｄＰｃ、ＦｅＰｃ、Ｍ
ｎＰｃ、ＣｌＡｌＰｃ、ＣｌＧａＰｃ、ＣｌＩｎＰｃ、
ＣｌＳｎＰｃ、Ｃｌ2 ＳｉＰｃ、（ＨＯ）ＡｌＰｃ、
（ＨＯ）ＧａＰｃ、ＶＯＰｃ、ＴｉＯＰｃ、ＭｏＯＰ
ｃ、ＧａＰｃ−Ｏ−ＧａＰｃ等のフタロシアニン誘導体
およびナフタロシアニン誘導体等があるが、これらに限
定されるものではない。In the organic EL device of the present invention, a more effective hole injection material is an aromatic tertiary amine derivative or a phthalocyanine derivative. Specifically, examples of the aromatic tertiary amine derivative include triphenylamine, tolylamine, tolylphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1 ′.
-Biphenyl-4,4'-diamine, N, N, N'N '
-(4-methylphenyl) -1,1′-phenyl-4,
4′-diamine, N, N, N′N ′-(4-methylphenyl) -1,1′-biphenyl-4,4′-diamine,
N, N'-diphenyl-N, N'-dinaphthyl-1,
1'-biphenyl-4,4'-diamine, N, N'-
(Methylphenyl) -N, N ′-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N
Examples include, but are not limited to, -bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane and the like, and oligomers and polymers having an aromatic tertiary amine skeleton. As phthalocyanine (Pc) derivatives, H 2 Pc, CuPc, C
oPc, NiPc, ZnPc, PdPc, FePc, M
nPc, ClAlPc, ClGaPc, ClInPc,
ClSnPc, Cl 2 SiPc, (HO) AlPc,
(HO) GaPc, VOPc, TiOPc, MoOP
c, a phthalocyanine derivative such as GaPc-O-GaPc, a naphthalocyanine derivative, and the like, but are not limited thereto.
【００５５】電子注入材料としては、電子を輸送する能
力を持ち、陰極からの電子注入効果、発光層または発光
材料に対して優れた電子輸送効果を有し、発光層で生成
した励起子の正孔注入層への移動を防止し、かつ薄膜形
成能力の優れた化合物が挙げられる。例えば、フルオレ
ノン、アントラキノジメタン、ジフェノキノン、チオピ
ランジオキシド、オキサゾール、オキサジアゾール、ト
リアゾール、イミダゾール、ペリレンテトラカルボン
酸、フレオレニリデンメタン、アントラキノジメタン、
アントロン等とそれらの誘導体があるが、これらに限定
されるものではない。また、正孔注入材料に電子受容物
質を、電子注入材料に電子供与性物質を添加することに
より増感させることもできる。The electron injecting material has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron transporting effect on the light emitting layer or the light emitting material, and has a positive effect on excitons generated in the light emitting layer. Compounds that prevent migration to the hole injection layer and have excellent thin film forming ability are mentioned. For example, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane,
Examples include, but are not limited to, anthrones and derivatives thereof. In addition, sensitization can be performed by adding an electron accepting substance to the hole injecting material and adding an electron donating substance to the electron injecting material.
【００５６】本発明の有機ＥＬ素子において、さらに効
果的な電子注入材料は、金属錯体化合物もしくは含窒素
五員環誘導体である。具体的には、金属錯体化合物とし
ては、８−ヒドロキシキノリナートリチウム、ビス（８
−ヒドロキシキノリナート）亜鉛、ビス（８−ヒドロキ
シキノリナート）銅、ビス（８−ヒドロキシキノリナー
ト）マンガン、トリス（８−ヒドロキシキノリナート）
アルミニウム、トリス（２−メチル−８−ヒドロキシキ
ノリナート）アルミニウム、トリス（８−ヒドロキシキ
ノリナート）ガリウム、ビス（１０−ヒドロキシベンゾ
［ｈ］キノリナート）ベリリウム、ビス（１０−ヒドロ
キシベンゾ［ｈ］キノリナート）亜鉛、ビス（２−メチ
ル−８−キノリナート）クロロガリウム、ビス（２−メ
チル−８−キノリナート）（ｏ−クレゾラート）ガリウ
ム、ビス（２−メチル−８−キノリナート）（１−ナフ
トラート）アルミニウム、ビス（２−メチル−８−キノ
リナート）（２−ナフトラート）ガリウム等があるが、
これらに限定されるものではない。また、含窒素五員誘
導体としては、オキサゾール、チアゾール、オキサジア
ゾール、チアジアゾールもしくはトリアゾール誘導体が
好ましい。具体的には、２，５−ビス（１−フェニル）
−１，３，４−オキサゾール、ジメチルＰＯＰＯＰ、
２，５−ビス（１−フェニル）−１，３，４−チアゾー
ル、２，５−ビス（１−フェニル）−１，３，４−オキ
サジアゾール、２−（４’−ｔｅｒｔ−ブチルフェニ
ル）−５−( ４”−ビフェニル) １，３，４−オキサジ
アゾール、２，５−ビス（１−ナフチル）−１，３，４
−オキサジアゾール、１，４−ビス［２−( ５−フェニ
ルオキサジアゾリル) ］ベンゼン、１，４−ビス［２−
( ５−フェニルオキサジアゾリル) −４−ｔｅｒｔ−ブ
チルベンゼン］、２−（４’−ｔｅｒｔ−ブチルフェニ
ル）−５−( ４”−ビフェニル) −１，３，４−チアジ
アゾール、２，５−ビス（１−ナフチル）−１，３，４
−チアジアゾール、１，４−ビス［２−( ５−フェニル
チアジアゾリル) ］ベンゼン、２−（４’−ｔｅｒｔ−
ブチルフェニル）−５−( ４”−ビフェニル) −１，
３，４−トリアゾール、２，５−ビス（１−ナフチル）
−１，３，４−トリアゾール、１，４−ビス［２−( ５
−フェニルトリアゾリル) ］ベンゼン等があるが、これ
らに限定されるものではない。In the organic EL device of the present invention, a more effective electron injecting material is a metal complex compound or a nitrogen-containing five-membered ring derivative. Specifically, as the metal complex compound, lithium 8-hydroxyquinolinate, bis (8
-Hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato)
Aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] (Quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl-8-quinolinato) (1-naphtholate) aluminum , Bis (2-methyl-8-quinolinato) (2-naphtholate) gallium and the like,
It is not limited to these. As the nitrogen-containing five-membered derivative, an oxazole, thiazole, oxadiazole, thiadiazole or triazole derivative is preferable. Specifically, 2,5-bis (1-phenyl)
-1,3,4-oxazole, dimethyl POPOP,
2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) -1,3,4-oxadiazole, 2- (4′-tert-butylphenyl) ) -5- (4 "-biphenyl) 1,3,4-oxadiazole, 2,5-bis (1-naphthyl) -1,3,4
-Oxadiazole, 1,4-bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2-
(5-phenyloxadiazolyl) -4-tert-butylbenzene], 2- (4'-tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-thiadiazole, 2,5- Bis (1-naphthyl) -1,3,4
-Thiadiazole, 1,4-bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4'-tert-
(Butylphenyl) -5- (4 "-biphenyl) -1,
3,4-triazole, 2,5-bis (1-naphthyl)
-1,3,4-triazole, 1,4-bis [2- (5
-Phenyltriazolyl)] benzene and the like, but are not limited thereto.
【００５７】本発明の有機ＥＬ素子において、本発明の
一般式の化合物の他に、発光材料、発光補助材料、正孔
注入材料および電子注入材料の少なくとも１種が同一層
に含有されてもよい。また、本発明により得られた有機
ＥＬ素子の、温度、湿度、雰囲気等に対する安定性の向
上のために、素子の表面に保護層を設けたり、シリコン
オイル等を封入して素子全体を保護することも可能であ
る。In the organic EL device of the present invention, in addition to the compound of the general formula of the present invention, at least one of a luminescent material, a luminescent auxiliary material, a hole injection material and an electron injection material may be contained in the same layer. . In order to improve the stability of the organic EL device obtained according to the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device, or silicon oil or the like is sealed to protect the entire device. It is also possible.
【００５８】以上のように、本発明では有機ＥＬ素子に
一般式の化合物を用いたため、発光効率と発光輝度を高
くできた。また、この素子は熱や電流に対して非常に安
定であり、さらには低い駆動電圧で実用的に使用可能の
発光輝度が得られるため、従来まで大きな問題であった
劣化も大幅に低下させることができた。As described above, in the present invention, since the compound of the general formula was used for the organic EL device, the luminous efficiency and the luminous brightness could be increased. In addition, this device is extremely stable against heat and current, and furthermore, it can emit light that can be practically used at a low driving voltage, so that the deterioration, which has been a major problem until now, can be significantly reduced. Was completed.
【００５９】本発明の有機ＥＬ素子は、壁掛けテレビ等
のフラットパネルディスプレイや、平面発光体として、
複写機やプリンター等の光源、液晶ディスプレイや計器
類等の光源、表示板、標識灯等へ応用が考えられ、その
工業的価値は非常に大きい。The organic EL device of the present invention can be used as a flat panel display such as a wall-mounted television or a flat luminous body.
It can be applied to light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and sign lamps, and its industrial value is extremely large.
【００６０】本発明の材料は、有機ＥＬ素子、電子写真
感光体、光電変換素子、太陽電池、イメージセンサー等
の分野においても好適に使用できる。The material of the present invention can be suitably used in the fields of organic EL devices, electrophotographic photosensitive members, photoelectric conversion devices, solar cells, image sensors and the like.
【００６１】[0061]
【実施例】以下、本発明を実施例に基づきさらに詳細に
説明する。 化合物（１）の合成方法 ベンゼン２００部中に、アントラキノン１０部、ジフェ
ニルアミン３５部、およびピリジン１５部を入れ、１０
℃にて四塩化チタン４０部を滴下し、２０時間室温で撹
拌した。その後、５００部の水で希釈し、希水酸化ナト
リウム水溶液で中和した。この後、酢酸エチルで抽出を
行い、濃縮し、シリカゲルを用いたカラムクロマトグラ
フィーにより精製して黄色の蛍光を有する針状結晶８部
を得た。分子量分析の結果、化合物（１）であることを
確認した。以下に生成物の元素分析結果を示す。 元素分析結果 Ｃ38Ｈ28Ｎ2 として 計算値（％）：Ｃ：８９．０６ Ｈ：５．４７ Ｎ：５．４７ 実測値（％）：Ｃ：８９．１１ Ｈ：５．５５ Ｎ：５．３４The present invention will be described in more detail with reference to the following examples. Method for synthesizing compound (1) 10 parts of anthraquinone, 35 parts of diphenylamine and 15 parts of pyridine were placed in 200 parts of benzene, and
At 40 ° C., 40 parts of titanium tetrachloride was added dropwise, and the mixture was stirred at room temperature for 20 hours. Thereafter, the mixture was diluted with 500 parts of water and neutralized with a dilute aqueous sodium hydroxide solution. Thereafter, extraction was performed with ethyl acetate, the mixture was concentrated, and purified by column chromatography using silica gel to obtain 8 parts of needle crystals having yellow fluorescence. As a result of molecular weight analysis, it was confirmed that the product was Compound (1). The results of elemental analysis of the product are shown below. Elemental analysis result: C 38 H 28 N 2 Calculated value (%): C: 89.06 H: 5.47 N: 5.47 Actual value (%): C: 89.11 H: 5.55 N: 5 .34
【００６２】化合物（８）の合成方法 ９，１０−ジヨードアントラセン１５部、４，４−ジイ
ソプロピル（２−フェニル）ジフェニルアミン２７部、
および炭酸カリウム１２部、銅粉末０．８部を入れ、２
００℃にて３０時間加熱撹拌した。その後、５００部の
水で希釈し、クロロホルムを用いて、抽出をおこなっ
た。このクロロホルム層を濃縮し、シリカゲルを用いた
カラムクロマトグラフィーにより精製を行い、ｎ−ヘキ
サンで再沈澱をして黄色の蛍光を有する粉末１８部を得
た。分子量分析の結果、化合物（９）であることを確認
した。以下に生成物の元素分析結果を示す。 元素分析結果 Ｃ74Ｈ68Ｎ2 として 計算値（％）：Ｃ：９０．２４ Ｈ：６．９１ Ｎ：２．８５ 実測値（％）：Ｃ：９０．５９ Ｈ：６．８１ Ｎ：２．６０Method for synthesizing compound (8) 15 parts of 9,10-diiodoanthracene, 27 parts of 4,4-diisopropyl (2-phenyl) diphenylamine,
And 12 parts of potassium carbonate and 0.8 parts of copper powder.
The mixture was heated and stirred at 00 ° C. for 30 hours. Thereafter, the mixture was diluted with 500 parts of water and extracted with chloroform. The chloroform layer was concentrated, purified by column chromatography using silica gel, and reprecipitated with n-hexane to obtain 18 parts of a powder having yellow fluorescence. As a result of molecular weight analysis, it was confirmed to be compound (9). The results of elemental analysis of the product are shown below. Elemental analysis result: C 74 H 68 N 2 Calculated value (%): C: 90.24 H: 6.91 N: 2.85 Actual value (%): C: 90.59 H: 6.81 N: 2 .60
【００６３】化合物（１１）の合成方法 ９，１０−ジヨードアントラセン１２部、１−ナフチル
−フェニルアミン２５部、および炭酸カリウム２０部、
銅粉末０．６部を入れ、２００℃にて３０時間加熱撹拌
した。その後、６００部の水で希釈し、クロロホルムを
用いて、抽出をおこなった。このクロロホルム層を濃縮
し、シリカゲルを用いたカラムクロマトグラフィーによ
り精製を行い、ｎ−ヘキサンで再結晶をして黄色の蛍光
を有する針条結晶２７部を得た。分子量分析の結果、化
合物（１１）であることを確認した。以下に生成物の元
素分析結果を示す。 元素分析結果 Ｃ46Ｈ32Ｎ2 として 計算値（％）：Ｃ：９０．２０ Ｈ：５．２３ Ｎ：４．５７ 実測値（％）：Ｃ：９０．３９ Ｈ：５．３１ Ｎ：４．３０Method for synthesizing compound (11) 12 parts of 9,10-diiodoanthracene, 25 parts of 1-naphthyl-phenylamine, 20 parts of potassium carbonate,
0.6 part of copper powder was added and heated and stirred at 200 ° C. for 30 hours. Then, the mixture was diluted with 600 parts of water and extracted with chloroform. The chloroform layer was concentrated, purified by column chromatography using silica gel, and recrystallized with n-hexane to obtain 27 parts of needle crystals having yellow fluorescence. As a result of molecular weight analysis, it was confirmed to be Compound (11). The results of elemental analysis of the product are shown below. Elemental analysis result: C 46 H 32 N 2 Calculated value (%): C: 90.20 H: 5.23 N: 4.57 Actual value (%): C: 90.39 H: 5.31 N: 4 .30
【００６４】実施例１ 洗浄したＩＴＯ電極付きガラス板上に、化合物（３）、
２，５−ビス（１−ナフチル）−１，３，４−オキサジ
アゾール、ポリカーボネート樹脂（帝人化成：パンライ
トＫ−１３００）を２：３：５の比率でテトラヒドロフ
ランに溶解させ、スピンコーティング法により膜厚１０
０ｎｍの発光層を得た。その上に、マグネシウムと銀を
１０：１で混合した合金で膜厚１５０ｎｍの電極を形成
して有機ＥＬ素子を得た。この素子は、直流電圧５Ｖで
１２０（ｃｄ／ｍ2 ）、発光効率０．７０（ｌｍ／Ｗ）
の緑色発光が得られた。Example 1 Compound (3) was placed on a washed glass plate with an ITO electrode.
2,5-bis (1-naphthyl) -1,3,4-oxadiazole and polycarbonate resin (Teijin Kasei: Panlite K-1300) are dissolved in tetrahydrofuran at a ratio of 2: 3: 5, and spin coating is performed. 10
A light emitting layer of 0 nm was obtained. An electrode having a thickness of 150 nm was formed thereon with an alloy of magnesium and silver mixed at a ratio of 10: 1 to obtain an organic EL device. This element has a direct current voltage of 5 V, 120 (cd / m 2 ), and a luminous efficiency of 0.70 (lm / W).
Green light emission was obtained.
【００６５】実施例２ 洗浄したＩＴＯ電極付きガラス板上に、化合物（６）を
塩化メチレンに溶解させ、スピンコーティング法により
膜厚５０ｎｍの正孔輸送型発光層を得た。次いで、ビス
（２−メチル−８−キノリナート）（１−ナフトラー
ト）ガリウム錯体を真空蒸着して膜厚１０ｎｍの電子注
入層を作成し、その上に、マグネシウムと銀を１０：１
で混合した合金で膜厚１００ｎｍの電極を形成して有機
ＥＬ素子を得た。電子注入層は１０-6Ｔｏｒｒの真空中
で、基板温度室温の条件下で蒸着した。この素子は、直
流電圧５Ｖで約３００ｃｄ／ｍ2 、最高輝度２２００ｃ
ｄ／ｍ2 、発光効率０．９０（ｌｍ／Ｗ）の緑色発光が
得られた。Example 2 A compound (6) was dissolved in methylene chloride on a washed glass plate with an ITO electrode, and a 50 nm-thick hole transport type light emitting layer was obtained by spin coating. Then, a bis (2-methyl-8-quinolinato) (1-naphtholate) gallium complex was vacuum-deposited to form an electron injection layer having a thickness of 10 nm, and magnesium and silver were added thereto in a ratio of 10: 1.
An electrode having a thickness of 100 nm was formed from the alloy mixed in the above step to obtain an organic EL device. The electron injection layer was deposited at a substrate temperature of room temperature in a vacuum of 10 -6 Torr. This element has a DC voltage of 5 V, about 300 cd / m 2 , and a maximum luminance of 2200 c
Green light having a d / m 2 and a luminous efficiency of 0.90 (lm / W) was obtained.
【００６６】実施例３ 洗浄したＩＴＯ電極付きガラス板上に、化合物（６）を
真空蒸着して、膜厚５０ｎｍに正孔輸送型発光層を形成
した。次いで、ビス（２−メチル−８−キノリナート）
（１−ナフトラート）ガリウム錯体を真空蒸着して膜厚
１０ｎｍの電子注入層を作成し、その上に、マグネシウ
ムと銀を１０：１で混合した合金で膜厚１００ｎｍの電
極を形成して有機ＥＬ素子を得た。電子注入層は１０
- 6 Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着
した。この素子は、直流電圧５Ｖで約３５０ｃｄ／
ｍ2 、最高輝度１１０００ｃｄ／ｍ2 、発光効率１．０
５（ｌｍ／Ｗ）の緑色発光が得られた。Example 3 A compound (6) was vacuum-deposited on a washed glass plate with an ITO electrode to form a hole-transporting luminescent layer with a thickness of 50 nm. Then, bis (2-methyl-8-quinolinate)
(1-Naphtholate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 10 nm, and an electrode having a thickness of 100 nm is formed on the electron injection layer with an alloy of magnesium and silver mixed at a ratio of 10: 1. An element was obtained. The electron injection layer is 10
- of 6 Torr in vacuum, and deposited under a substrate temperature of room temperature. This element has about 350 cd /
m 2 , maximum luminance 11,000 cd / m 2 , luminous efficiency 1.0
Green light emission of 5 (lm / W) was obtained.
【００６７】実施例４〜２２ 洗浄したＩＴＯ電極付きガラス板上に、下記化学構造で
示される化合物（５０）を真空蒸着して、膜厚２０ｎｍ
の正孔注入層を得た。次いで、発光材料として表２の化
合物を真空蒸着して膜厚２０ｎｍの発光層を得た。さら
に、ビス（２−メチル−８−キノリナート）（１−フェ
ノラート）ガリウム錯体を真空蒸着して膜厚２０ｎｍの
電子注入層を作成し、その上に、マグネシウムと銀を１
０：１で混合した合金で膜厚１５０ｎｍの膜厚の電極を
形成して有機ＥＬ素子を得た。各層は１０-6Ｔｏｒｒの
真空中で、基板温度室温の条件下で蒸着した。この素子
の発光特性を表２に示す。ここでの発光輝度は、直流電
圧５Ｖ印可時の輝度であり、本実施例の有機ＥＬ素子
は、全て最高輝度１００００ｃｄ／ｍ2 以上であった。 化合物（５０）Examples 4 to 22 A compound (50) represented by the following chemical structure was vacuum-deposited on a washed glass plate with an ITO electrode to form a film having a thickness of 20 nm.
Was obtained. Next, the compounds shown in Table 2 were vacuum-deposited as light-emitting materials to obtain a light-emitting layer having a thickness of 20 nm. Further, a bis (2-methyl-8-quinolinate) (1-phenolate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 20 nm, and magnesium and silver are further deposited on the electron injection layer.
An electrode having a thickness of 150 nm was formed from an alloy mixed at 0: 1 to obtain an organic EL device. Each layer was deposited at a substrate temperature of room temperature in a vacuum of 10 -6 Torr. Table 2 shows the light emission characteristics of this device. The light emission luminance here is the luminance when a DC voltage of 5 V is applied, and all the organic EL elements of this example had a maximum luminance of 10,000 cd / m 2 or more. Compound (50)
【００６８】[0068]
【化１１】 Embedded image
【００６９】[0069]
【表２】 [Table 2]
【００７０】実施例２４ 洗浄したＩＴＯ電極付きガラス板上に、化合物（５０）
を真空蒸着して、膜厚２０ｎｍの正孔注入層を得た。次
いで、発光材料として化合物（２３）を真空蒸着して膜
厚２０ｎｍの発光層を得た。さらに、２，５−ビス（１
−ナフチル）−１，３，４−オキサジアゾールを真空蒸
着して、膜厚２０ｎｍの電子注入層を得た。その上に、
マグネシウムと銀を１０：１で混合した合金で膜厚１５
０ｎｍの電極を形成して有機ＥＬ素子を得た。この素子
は、直流電圧５Ｖで７７０ｃｄ／ｍ2 、最高輝度２７０
００ｃｄ／ｍ2 、発光効率１．８０（ｌｍ／Ｗ）の緑色
発光が得られた。Example 24 Compound (50) was placed on a washed glass plate with an ITO electrode.
Was vacuum-deposited to obtain a hole injection layer having a thickness of 20 nm. Next, the compound (23) was vacuum-deposited as a light emitting material to obtain a light emitting layer having a thickness of 20 nm. Further, 2,5-bis (1
-Naphthyl) -1,3,4-oxadiazole was vacuum-deposited to obtain a 20 nm-thick electron injection layer. in addition,
An alloy of magnesium and silver mixed at a ratio of 10: 1 with a film thickness of 15
An 0 nm electrode was formed to obtain an organic EL device. This device has a DC voltage of 5 V, 770 cd / m 2 , and a maximum luminance of 270
Green light emission with a luminance of 00 cd / m 2 and a luminous efficiency of 1.80 (lm / W) was obtained.
【００７１】実施例２５ ＩＴＯ電極と化合物（５０）との間に、無金属フタロシ
アニンの膜厚５ｎｍの正孔注入層を設ける以外は、実施
例２４と同様の方法で有機ＥＬ素子を作製した。この素
子は、直流電圧５Ｖで１２００ｃｄ／ｍ2 、最高輝度２
９０００ｃｄ／ｍ2 、発光効率１．７０（ｌｍ／Ｗ）の
緑色発光が得られた。実施例２４の有機ＥＬ素子に比べ
て、低電圧側での発光輝度が高かった。Example 25 An organic EL device was manufactured in the same manner as in Example 24 except that a hole injection layer having a thickness of 5 nm made of metal-free phthalocyanine was provided between the ITO electrode and the compound (50). This device has 1200 cd / m 2 at a DC voltage of 5 V and a maximum luminance of 2
Green light having a luminance of 9000 cd / m 2 and a luminous efficiency of 1.70 (lm / W) was obtained. The emission luminance on the low voltage side was higher than that of the organic EL device of Example 24.
【００７２】実施例２６ 化合物（５０）の代わりに無金属フタロシアニンの膜厚
２０ｎｍの正孔注入層を設ける以外は、実施例２４と同
様の方法で有機ＥＬ素子を作製した。この素子は、直流
電圧５Ｖで６５０ｃｄ／ｍ2 、最高輝度１５０００ｃｄ
／ｍ2 、発光効率１．３０（ｌｍ／Ｗ）の緑色発光が得
られた。Example 26 An organic EL device was manufactured in the same manner as in Example 24, except that a hole injection layer of metal-free phthalocyanine having a thickness of 20 nm was provided instead of the compound (50). This device has 650 cd / m 2 at a DC voltage of 5 V and a maximum luminance of 15000 cd.
/ M 2 , and green light emission with a luminous efficiency of 1.30 (lm / W) was obtained.
【００７３】実施例２７ 発光層として、化合物（２３）：化合物（５１）を１０
０：１の重量比で蒸着した膜厚１０ｎｍの発光層を使用
する以外は、実施例１１と同様の方法で有機ＥＬ素子を
作製した。この素子は、直流電圧５Ｖで７００ｃｄ／ｍ
2 、最高輝度３５０００ｃｄ／ｍ2 、発光効率２．７０
（ｌｍ／Ｗ）の緑色発光が得られた。 化合物（５１）Example 27 As a light emitting layer, compound (23): compound (51)
An organic EL device was manufactured in the same manner as in Example 11, except that a 10 nm-thick light emitting layer deposited at a weight ratio of 0: 1 was used. This element is 700 cd / m at 5 VDC.
2 , maximum luminance 35000 cd / m 2 , luminous efficiency 2.70
Green light emission of (lm / W) was obtained. Compound (51)
【００７４】[0074]
【化１２】 Embedded image
【００７５】実施例２８ 発光層として、化合物（２３）：化合物（５２）を１０
０：１の重量比で蒸着した膜厚１０ｎｍの発光層を使用
する以外は、実施例１１と同様の方法で有機ＥＬ素子を
作製した。この素子は、直流電圧５Ｖで５００ｃｄ／ｍ
2 、最高輝度１８０００ｃｄ／ｍ2 、発光効率１．６５
（ｌｍ／Ｗ）の化合物（２２）からの橙色発光が得られ
た。 化合物（５２）Example 28 As a light emitting layer, compound (23): compound (52)
An organic EL device was manufactured in the same manner as in Example 11, except that a 10 nm-thick light emitting layer deposited at a weight ratio of 0: 1 was used. This element is 500 cd / m at 5 VDC.
2 , maximum luminance 18000 cd / m 2 , luminous efficiency 1.65
Orange light emission from (lm / W) compound (22) was obtained. Compound (52)
【００７６】[0076]
【化１３】 Embedded image
【００７７】本実施例で示された有機ＥＬ素子は、二層
型以上の素子構成において、最大発光輝度１００００ｃ
ｄ／ｍ2 以上の発光が得られ、全て高い発光効率を得る
ことができた。本実施例で示された有機ＥＬ素子につい
て、３ｍＡ／ｃｍ2 で連続発光させたところ、１０００
時間以上安定な発光を観測することができた。本発明の
有機ＥＬ素子は発光効率、発光輝度の向上と長寿命化を
達成するものであり、併せて使用される発光材料、発光
補助材料、正孔輸送材料、電子輸送材料、増感剤、樹
脂、電極材料等および素子作製方法を限定するものでは
ない。The organic EL device shown in this example has a maximum light emission luminance of 10,000 c
Light emission of d / m 2 or more was obtained, and high luminous efficiency was obtained in all cases. When the organic EL device shown in this example was continuously emitted at 3 mA / cm 2 ,
Light emission stable for more than an hour could be observed. The organic EL device of the present invention achieves improvement of luminous efficiency, luminous luminance and long life, and is used together with a luminescent material, a luminescent auxiliary material, a hole transport material, an electron transport material, a sensitizer, It does not limit the resin, the electrode material and the like, and the element manufacturing method.
【発明の効果】本発明の有機ＥＬ素子材料を発光材料と
して使用した有機ＥＬ素子は、従来に比べて高い発光効
率で高輝度の発光を示し、長寿命の有機ＥＬ素子を得る
ことができた。According to the organic EL device using the organic EL device material of the present invention as a light-emitting material, the device emits light with high luminous efficiency and high luminance as compared with the prior art, and a long-life organic EL device can be obtained. .
Claims (5)
トロルミネッセンス素子用発光材料。 一般式［１］ 【化１】 ［式中、Ａ1 〜Ａ4 は、それぞれ独立に、置換もしくは
未置換の炭素数６〜１６のアリール基を表す。Ｒ1 〜Ｒ
8 は、それぞれ独立に、水素原子、ハロゲン原子、置換
もしくは未置換のアルキル基、置換もしくは未置換のア
ルコキシ基、置換もしくは未置換のアリール基、置換も
しくは未置換のアミノ基を表す（隣接した置換基同志で
結合して新たな６員アリール環を形成しても良
い。）。］1. A light-emitting material for an organic electroluminescence device represented by the following general formula [1]. General formula [1] [Wherein, A 1 to A 4 each independently represent a substituted or unsubstituted aryl group having 6 to 16 carbon atoms. R 1 to R
8 independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group (neighboring substituted The groups may be bonded to form a new 6-membered aryl ring.). ]
トロルミネッセンス素子用発光材料。 一般式［２］ 【化２】 ［式中、Ｒ1 〜Ｒ28は、それぞれ独立に、水素原子、ハ
ロゲン原子、置換もしくは未置換のアルキル基、置換も
しくは未置換のアルコキシ基、置換もしくは未置換のア
リール基、置換もしくは未置換のアミノ基を表す。Ｒ1
〜Ｒ4もしくはＲ5〜Ｒ8は隣接した置換基同志で結合し
て新たな６員アリール環を形成してもよい。］2. A light emitting material for an organic electroluminescence device represented by the following general formula [2]. General formula [2] [Wherein, R 1 to R 28 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted Represents an amino group. R 1
To R 4 or R 5 to R 8 may form a new 6-membered aryl ring bonded with a substituent each other adjacent. ]
トロルミネッセンス素子用発光材料。 一般式［３］ 【化３】 ［式中、Ｒ1 〜Ｒ8 およびＲ29〜Ｒ48は、それぞれ独立
に、水素原子、ハロゲン原子、置換もしくは未置換のア
ルキル基、置換もしくは未置換のアルコキシ基、置換も
しくは未置換のアリール基、置換もしくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ4 は、それぞれ特立に、Ｏ、Ｓ、
Ｃ＝Ｏ、ＳＯ2 、（ＣＨ2 ）ｘ−Ｏ−（ＣＨ2 ）ｙ、置
換もしくは未置換のアルキレン基、置換もしくは未置換
の脂肪族環残基を表す。ここで、ｘおよびｙは、それぞ
れ０〜２０の正の整数を表すが、ｘ＋ｙ＝０となること
はない。Ｒ1〜Ｒ4もしくはＲ5〜Ｒ8は隣接した置換基同
志で結合して新たな６員アリール環を形成してもよ
い。］3. A light-emitting material for an organic electroluminescence device represented by the following general formula [3]. General formula [3] [Wherein, R 1 to R 8 and R 29 to R 48 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group Represents a substituted or unsubstituted amino group. X 1 to X 4 are O, S,
C = O, SO 2, represents a (CH 2) x-O- ( CH 2) y, a substituted or unsubstituted alkylene, substituted or unsubstituted aliphatic ring residue. Here, x and y each represent a positive integer of 0 to 20; however, x + y = 0 does not occur. R 1 to R 4 or R 5 to R 8 may be bonded by adjacent substituents to form a new 6-membered aryl ring. ]
トロルミネッセンス素子用発光材料。 一般式［４］ 【化４】 ［式中、Ｒ1 〜Ｒ8 およびＲ29〜Ｒ48は、それぞれ独立
に、水素原子、ハロゲン原子、置換もしくは未置換のア
ルキル基、置換もしくは未置換のアルコキシ基、置換も
しくは未置換のアリール基、置換もしくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ4 は、それぞれ独立に、Ｏ、Ｓ、
Ｃ＝Ｏ、ＳＯ2 、（ＣＨ2 ）ｘ−Ｏ−（ＣＨ2 ）ｙ、置
換もしくは未置換のアルキレン基、置換もしくは未置換
の脂肪族環残基を表す。ここで、ｘおよびｙは、それぞ
れ０〜２０の正の整数を表すが、ｘ＋ｙ＝０となること
はない。Ｒ1〜Ｒ4もしくはＲ5〜Ｒ8は隣接した置換基同
志で結合して新たな６員アリール環を形成してもよ
い。］4. A light emitting material for an organic electroluminescence device represented by the following general formula [4]. General formula [4] [Wherein, R 1 to R 8 and R 29 to R 48 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group Represents a substituted or unsubstituted amino group. X 1 to X 4 are each independently O, S,
C = O, SO 2, represents a (CH 2) x-O- ( CH 2) y, a substituted or unsubstituted alkylene, substituted or unsubstituted aliphatic ring residue. Here, x and y each represent a positive integer of 0 to 20; however, x + y = 0 does not occur. R 1 to R 4 or R 5 to R 8 may be bonded by adjacent substituents to form a new 6-membered aryl ring. ]
トロルミネッセンス素子用発光材料。 一般式［５］ 【化５】 ［式中、Ｒ1 〜Ｒ8 およびＲ29〜Ｒ48は、それぞれ独立
に、水素原子、ハロゲン原子、置換もしくは未置換のア
ルキル基、置換もしくは未置換のアルコキシ基、置換も
しくは未置換のアリール基、置換もしくは未置換のアミ
ノ基を表す。Ｙ1〜Ｙ8 は、置換もしくは未置換の炭素
数１〜２０のアルキル基、置換もしくは未置換の炭素数
６〜１６のアリール基を表す。Ｒ1〜Ｒ4もしくはＲ5〜
Ｒ8は隣接した置換基同志で結合して新たな６員アリー
ル環を形成してもよい。］5. A light emitting material for an organic electroluminescence device represented by the following general formula [5]. General formula [5] [Wherein, R 1 to R 8 and R 29 to R 48 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group Represents a substituted or unsubstituted amino group. Y 1 to Y 8 represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and a substituted or unsubstituted aryl group having 6 to 16 carbon atoms. R 1 to R 4 or R 5 to
R 8 may be linked by adjacent substituents to form a new 6-membered aryl ring. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8244491A JP2924809B2 (en) | 1995-09-25 | 1996-09-17 | Light-emitting materials for organic electroluminescence devices |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24560795 | 1995-09-25 | ||
| JP1243096 | 1996-01-29 | ||
| JP8-170810 | 1996-07-01 | ||
| JP17081096 | 1996-07-01 | ||
| JP8-12430 | 1996-07-01 | ||
| JP7-245607 | 1996-07-01 | ||
| JP8244491A JP2924809B2 (en) | 1995-09-25 | 1996-09-17 | Light-emitting materials for organic electroluminescence devices |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1072579A true JPH1072579A (en) | 1998-03-17 |
| JP2924809B2 JP2924809B2 (en) | 1999-07-26 |
Family
ID=27455803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8244491A Expired - Lifetime JP2924809B2 (en) | 1995-09-25 | 1996-09-17 | Light-emitting materials for organic electroluminescence devices |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2924809B2 (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2002020693A1 (en) * | 2000-09-07 | 2004-01-15 | 出光興産株式会社 | Organic electroluminescence device |
| WO2004078872A2 (en) | 2003-03-05 | 2004-09-16 | Lg Electronics Inc. | Organic electroluminescent device |
| EP1491610A2 (en) | 2003-06-27 | 2004-12-29 | Canon Kabushiki Kaisha | Organic electroluminescent device |
| US7129386B2 (en) | 2003-06-27 | 2006-10-31 | Canon Kabushiki Kaisha | Substituted anthryl derivative and electroluminescence device using the same |
| US7173131B2 (en) | 2003-06-27 | 2007-02-06 | Canon Kabushiki Kaisha | Anthryl derivative group substituted compound, and organic luminescent device making use of same |
| US7365198B2 (en) | 2006-03-02 | 2008-04-29 | Canon Kabushiki Kaisha | Silyl compound, light emitting material, and organic light emitting device using the same |
| US7375250B2 (en) | 2003-06-27 | 2008-05-20 | Canon Kabushiki Kaisha | Aminoanthryl derivative substitution compound and organic electroluminescence device using the same |
| JP2009242806A (en) * | 1998-12-28 | 2009-10-22 | Idemitsu Kosan Co Ltd | Material for organic electroluminescent element and organic electroluminescent element using the same |
| US7709104B2 (en) | 2004-11-26 | 2010-05-04 | Canon Kabushiki Kaisha | Aminoanthryl derivative-substituted pyrene compound and organic light-emitting device |
| WO2011033753A1 (en) * | 2009-09-18 | 2011-03-24 | 富士電機ホールディングス株式会社 | Pendant type polymer, color-conversion films including pendant type polymer, and organic el device for multicolor light emission |
| US7929209B2 (en) | 2006-02-28 | 2011-04-19 | Canon Kabushiki Kaisha | Optical element and method of manufacturing optical element with each of first and second layers having a repetition structure |
| US7952269B2 (en) | 2004-11-26 | 2011-05-31 | Canon Kabushiki Kaisha | Organic light-emitting device |
-
1996
- 1996-09-17 JP JP8244491A patent/JP2924809B2/en not_active Expired - Lifetime
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009242806A (en) * | 1998-12-28 | 2009-10-22 | Idemitsu Kosan Co Ltd | Material for organic electroluminescent element and organic electroluminescent element using the same |
| JP4630378B2 (en) * | 1998-12-28 | 2011-02-09 | 出光興産株式会社 | Material for organic electroluminescence device and organic electroluminescence device using the same |
| US8841003B2 (en) | 2000-09-07 | 2014-09-23 | Idemitsu Kosan Co., Ltd. | Organic electric-field light-emitting element |
| JP2011054981A (en) * | 2000-09-07 | 2011-03-17 | Idemitsu Kosan Co Ltd | Organic electric-field light-emitting element |
| JP4632628B2 (en) * | 2000-09-07 | 2011-02-16 | 出光興産株式会社 | Organic electroluminescence device |
| JPWO2002020693A1 (en) * | 2000-09-07 | 2004-01-15 | 出光興産株式会社 | Organic electroluminescence device |
| US7879465B2 (en) | 2000-09-07 | 2011-02-01 | Idemitsu Kosan Co., Ltd. | Organic electric-field light-emitting element |
| WO2004078872A2 (en) | 2003-03-05 | 2004-09-16 | Lg Electronics Inc. | Organic electroluminescent device |
| WO2004078872A3 (en) * | 2003-03-05 | 2004-12-16 | Lg Electronics Inc | Organic electroluminescent device |
| US7651788B2 (en) | 2003-03-05 | 2010-01-26 | Lg Display Co., Ltd. | Organic electroluminescent device |
| US7309533B2 (en) | 2003-06-27 | 2007-12-18 | Canon Kabushiki Kaisha | Substituted anthryl derivative and electroluminescence device using the same |
| US7491450B2 (en) | 2003-06-27 | 2009-02-17 | Canon Kabushiki Kaisha | Organic electroluminescent device |
| US7375250B2 (en) | 2003-06-27 | 2008-05-20 | Canon Kabushiki Kaisha | Aminoanthryl derivative substitution compound and organic electroluminescence device using the same |
| EP1491610A2 (en) | 2003-06-27 | 2004-12-29 | Canon Kabushiki Kaisha | Organic electroluminescent device |
| US7358409B2 (en) | 2003-06-27 | 2008-04-15 | Canon Kabushiki Kaisha | Substituted anthryl derivative and electroluminescence device using the same |
| US7173131B2 (en) | 2003-06-27 | 2007-02-06 | Canon Kabushiki Kaisha | Anthryl derivative group substituted compound, and organic luminescent device making use of same |
| US7129386B2 (en) | 2003-06-27 | 2006-10-31 | Canon Kabushiki Kaisha | Substituted anthryl derivative and electroluminescence device using the same |
| US7709104B2 (en) | 2004-11-26 | 2010-05-04 | Canon Kabushiki Kaisha | Aminoanthryl derivative-substituted pyrene compound and organic light-emitting device |
| US7952269B2 (en) | 2004-11-26 | 2011-05-31 | Canon Kabushiki Kaisha | Organic light-emitting device |
| US7929209B2 (en) | 2006-02-28 | 2011-04-19 | Canon Kabushiki Kaisha | Optical element and method of manufacturing optical element with each of first and second layers having a repetition structure |
| US7365198B2 (en) | 2006-03-02 | 2008-04-29 | Canon Kabushiki Kaisha | Silyl compound, light emitting material, and organic light emitting device using the same |
| JP2011063763A (en) * | 2009-09-18 | 2011-03-31 | Fuji Electric Holdings Co Ltd | Pendant-type polymer compound, color conversion film using pendant-type polymer compound, and organic el device for multicolor light emission |
| WO2011033753A1 (en) * | 2009-09-18 | 2011-03-24 | 富士電機ホールディングス株式会社 | Pendant type polymer, color-conversion films including pendant type polymer, and organic el device for multicolor light emission |
| US8785007B2 (en) | 2009-09-18 | 2014-07-22 | Adeka Corporation | Pendant-type polymeric compound, color conversion film using pendant-type polymeric compound, and multicolor emission organic EL device |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2924809B2 (en) | 1999-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3503403B2 (en) | Light emitting material for organic electroluminescent device and organic electroluminescent device using the same | |
| EP0786926B1 (en) | Light-emitting material for organo-electroluminescence device and organo-electroluminescence devive for which the light-emitting material is adapted | |
| JP3511825B2 (en) | Light emitting material for organic electroluminescent device and organic electroluminescent device using the same | |
| JP4205059B2 (en) | Material for organic electroluminescence device and organic electroluminescence device using the same | |
| JP4188369B2 (en) | Aromatic amine derivatives | |
| JP3498533B2 (en) | Light emitting material for organic electroluminescent device and organic electroluminescent device using the same | |
| JP3666086B2 (en) | Luminescent material for organic electroluminescence device and organic electroluminescence device using the same | |
| JP3924943B2 (en) | Organic electroluminescent device material and organic electroluminescent device using the same | |
| JPH11135261A (en) | Organic electroluminescent element material, and organic electroluminescent element using it | |
| JPH11111458A (en) | Organic electroluminescent element material and organic electroluminescent element using the same | |
| JPH11273860A (en) | Luminous material for organic electroluminescence and organic electroluminescent element using the same | |
| JP2000294373A (en) | Material for organic electroluminescence element and organic electroluminescence element using the material | |
| JP2924809B2 (en) | Light-emitting materials for organic electroluminescence devices | |
| JP3899698B2 (en) | Organic electroluminescent device material and organic electroluminescent device using the same | |
| JP3924799B2 (en) | Luminescent material for organic electroluminescence device and organic electroluminescence device using the same | |
| JP2000290645A (en) | Material for organic electroluminescent element and organic electroluminescent element using the same | |
| JP3945032B2 (en) | Luminescent material for organic electroluminescence device and organic electroluminescence device using the same | |
| JPH1072581A (en) | Luminescent material for organic electroluminescent element and organic electroluminescent element produced by using the same | |
| JP2924810B2 (en) | Organic electroluminescence device | |
| JP2001207167A (en) | Light-emission material for organic electro-luminescent element and organic electro-luminescent element using the same | |
| JP4211191B2 (en) | Material for organic electroluminescence device and organic electroluminescence device using the same | |
| JP3572903B2 (en) | Organic electroluminescent device material and organic electroluminescent device using the same | |
| JP2001011031A (en) | Compound for organic electroluminescence element and luminescent material for organic electroluminescence element using the same | |
| JP3340687B2 (en) | Organic electroluminescence device | |
| JP3508353B2 (en) | Light emitting material for organic electroluminescent device and organic electroluminescent device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110507 Year of fee payment: 12 |
|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120507 Year of fee payment: 13 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130507 Year of fee payment: 14 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140507 Year of fee payment: 15 |
|
| EXPY | Cancellation because of completion of term |