JP3518255B2 - Organic thin film EL device - Google Patents
Organic thin film EL deviceInfo
- Publication number
- JP3518255B2 JP3518255B2 JP15521097A JP15521097A JP3518255B2 JP 3518255 B2 JP3518255 B2 JP 3518255B2 JP 15521097 A JP15521097 A JP 15521097A JP 15521097 A JP15521097 A JP 15521097A JP 3518255 B2 JP3518255 B2 JP 3518255B2
- Authority
- JP
- Japan
- Prior art keywords
- thin film
- light emitting
- organic
- emitting layer
- transporting layer
- 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.)
- Expired - Fee Related
Links
- 239000010409 thin film Substances 0.000 title claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 52
- 239000000758 substrate Substances 0.000 claims description 48
- 239000000126 substance Substances 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000010410 layer Substances 0.000 description 158
- 239000000463 material Substances 0.000 description 38
- 239000010408 film Substances 0.000 description 34
- 238000000034 method Methods 0.000 description 30
- 238000007789 sealing Methods 0.000 description 19
- 238000007740 vapor deposition Methods 0.000 description 19
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 18
- 239000011521 glass Substances 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 229910052782 aluminium Inorganic materials 0.000 description 11
- -1 as a cathode Substances 0.000 description 11
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 238000004544 sputter deposition Methods 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
- 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 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 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 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 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 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 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 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 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 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 239000002131 composite material Substances 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
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000007733 ion plating Methods 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000642 polymer 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
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- YGLVWOUNCXBPJF-UHFFFAOYSA-N (2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene Chemical compound C1=CC=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YGLVWOUNCXBPJF-UHFFFAOYSA-N 0.000 description 1
- JCXLYAWYOTYWKM-UHFFFAOYSA-N (2,3,4-triphenylcyclopenta-1,3-dien-1-yl)benzene Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JCXLYAWYOTYWKM-UHFFFAOYSA-N 0.000 description 1
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- QNZKGZMRMGIXKO-UHFFFAOYSA-N 4-(2-hydroxyphenyl)benzonitrile Chemical compound OC1=CC=CC=C1C1=CC=C(C#N)C=C1 QNZKGZMRMGIXKO-UHFFFAOYSA-N 0.000 description 1
- FLDKBNKXUGMTQU-UHFFFAOYSA-N 4-phenyl-5-[3-(trifluoromethyl)phenyl]-2H-triazole Chemical compound C1(=CC=CC=C1)C1=C(N=NN1)C1=CC(=CC=C1)C(F)(F)F FLDKBNKXUGMTQU-UHFFFAOYSA-N 0.000 description 1
- ZHBOFZNNPZNWGB-UHFFFAOYSA-N 9,10-bis(phenylethynyl)anthracene Chemical compound C1=CC=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=CC=C1 ZHBOFZNNPZNWGB-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229910016569 AlF 3 Inorganic materials 0.000 description 1
- RWEXREZYTGQDKY-UHFFFAOYSA-N C1=CC=C2C([Li])=C(C=CC=C3)C3=CC2=C1 Chemical compound C1=CC=C2C([Li])=C(C=CC=C3)C3=CC2=C1 RWEXREZYTGQDKY-UHFFFAOYSA-N 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 229910015475 FeF 2 Inorganic materials 0.000 description 1
- 229910005540 GaP Inorganic materials 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- HNIOISBFRDVSAW-UHFFFAOYSA-K [Al+3].C(#N)C1=CC=C(C=C1)C1=C(C=CC=C1)[O-].CC1=NC2=C(C=CC(=C2C=C1)C#N)[O-].CC1=NC2=C(C=CC(=C2C=C1)C#N)[O-] Chemical compound [Al+3].C(#N)C1=CC=C(C=C1)C1=C(C=CC=C1)[O-].CC1=NC2=C(C=CC(=C2C=C1)C#N)[O-].CC1=NC2=C(C=CC(=C2C=C1)C#N)[O-] HNIOISBFRDVSAW-UHFFFAOYSA-K 0.000 description 1
- 230000032900 absorption of visible light Effects 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- JYMITAMFTJDTAE-UHFFFAOYSA-N aluminum zinc oxygen(2-) Chemical compound [O-2].[Al+3].[Zn+2] JYMITAMFTJDTAE-UHFFFAOYSA-N 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000008020 evaporation Effects 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
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- HZXMRANICFIONG-UHFFFAOYSA-N gallium phosphide Chemical compound [Ga]#P HZXMRANICFIONG-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- NJWNEWQMQCGRDO-UHFFFAOYSA-N indium zinc Chemical compound [Zn].[In] NJWNEWQMQCGRDO-UHFFFAOYSA-N 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- CELAVSIYCCQNGG-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1CCCCC1)C1=CC=C(C)C=C1 CELAVSIYCCQNGG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- NQHONLWXAMXQRF-UHFFFAOYSA-K quinolin-8-olate;scandium(3+) Chemical compound [Sc+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 NQHONLWXAMXQRF-UHFFFAOYSA-K 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000013464 silicone adhesive Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052950 sphalerite Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 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
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ＥＬ素子に係り、
より詳細には、有機薄膜ＥＬ素子に関する。TECHNICAL FIELD The present invention relates to an EL device,
More specifically, it relates to an organic thin film EL device.
【０００２】[0002]
【従来の技術】有機薄膜エレクトロルミネッセンス（以
下、ＥＬという）素子は、イーストマン・コダック社の
C. W. Tangらにより開発され、特開昭５９−１９４３９
３号公報、特開昭６３−２６４６９２号公報、特開昭６
３−２９５６９５号公報、特開平６−１７２７５１号公
報、特開平６−１９８３７８号公報、アプライド・フィ
ジックス・レター第５１巻第１２号第９１３頁（１９８
７年）、及びジャーナル・オブ・アプライドフィジック
ス第６５巻第９号第３６１０頁（１９８９年）等で開示
されている。2. Description of the Related Art Organic thin film electroluminescence (hereinafter referred to as EL) devices are manufactured by Eastman Kodak Company.
Developed by CW Tang et al., JP-A-59-19439
No. 3, JP-A-63-264692, JP-A-6
JP-A-3-295695, JP-A-6-172751, JP-A-6-198378, and Applied Physics Letter Vol. 51 No. 12, page 913 (198).
7), and Journal of Applied Physics Vol. 65, No. 9, page 3610 (1989) and the like.
【０００３】これら文献によると、有機薄膜ＥＬ素子
は、一般的には、基板上に、陽極、有機正孔注入輸送
層、有機発光層、及び陰極が順次積層された構成であ
り、以下のようにして形成される。According to these documents, an organic thin film EL element is generally constructed by laminating an anode, an organic hole injecting and transporting layer, an organic light emitting layer and a cathode in this order on a substrate. Is formed.
【０００４】まず、ガラスや樹脂フィルム等の透明絶縁
性の基板上に、蒸着法またはスパッタリング法等によ
り、インジウムとスズの複合酸化物（以下、ＩＴＯとい
う）からなる透明導電性被膜を、陽極として形成する。First, a transparent conductive film made of a composite oxide of indium and tin (hereinafter referred to as ITO) is used as an anode on a transparent insulating substrate such as glass or resin film by a vapor deposition method or a sputtering method. Form.
【０００５】次に、この陽極上に、銅フタロシアニン
（以下ＣｕＰｃという）、下記化学式（１）に示す１，
１−ビス（４−ジ−ｐ−トリルアミノフェニル）シクロ
ヘキサン［融点１８１．４〜１８２．４℃、ガラス転移
温度（Ｔg ）８４℃］、下記化学式（２）に示すＮ，
Ｎ，Ｎ’，Ｎ’−テトラ−ｐ−トリル−１，１’−ビフ
ェニル−４，４’−ジアミン［融点１２０℃］、また
は、下記化学式（３）に示す４，４’−ビス［Ｎ−（１
−ナフチル）−Ｎ−フェニルアミノ］ビフェニル［融点
２７７℃、Ｔg ９６℃］等のテトラアリールジアミン
を、有機正孔注入輸送層として、蒸着法により、１００
ｎｍ程度以下の厚さで、単層または積層して形成する。Next, on the anode, copper phthalocyanine (hereinafter referred to as CuPc), 1, represented by the following chemical formula (1),
1-bis (4-di-p-tolylaminophenyl) cyclohexane [melting point 181.4-182.4 ° C., glass transition temperature (T g ) 84 ° C.], N shown in the following chemical formula (2),
N, N ′, N′-tetra-p-tolyl-1,1′-biphenyl-4,4′-diamine [melting point 120 ° C.] or 4,4′-bis [N represented by the following chemical formula (3): -(1
-Naphthyl) -N-phenylamino] biphenyl [melting point 277 [deg.] C., Tg 96 [deg.] C.] tetraaryldiamine as an organic hole injecting and transporting layer to form 100
It is formed in a single layer or a stacked layer with a thickness of approximately nm or less.
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】さらに、この正孔注入輸送層上に、例え
ば、下記化学式（４）に示すテトラフェニルブタジエ
ン、下記化学式（５）に示すビス（２−メチル−８−キ
ノリラート）（パラ−フェニル−フェノラート）アルミ
ニウム（III ）にペリレンをドープした混合物、及び、
下記化学式（６）に示すビス（２−メチル−８−キノリ
ラート）アルミニウム（III ）−μ−オキソ−ビス（２
−メチル−８−キノリラート）アルミニウム（III ）に
ペリレンをドープした混合物等の青色有機蛍光体を、１
００ｎｍ程度以下の厚さで蒸着して有機発光層を形成す
る。Further, on the hole injecting and transporting layer, for example, tetraphenyl butadiene represented by the following chemical formula (4) and bis (2-methyl-8-quinolinylate) (para-phenyl-phenolate represented by the following chemical formula (5). ) A mixture of aluminum (III) doped with perylene, and
Bis (2-methyl-8-quinolylato) aluminum (III) -μ-oxo-bis (2) represented by the following chemical formula (6):
1-methyl-8-quinolylato) aluminum (III) was doped with a blue organic phosphor such as a mixture of perylene.
An organic light emitting layer is formed by vapor deposition with a thickness of about 00 nm or less.
【０００８】[0008]
【化３】 [Chemical 3]
【０００９】この有機発光層上に、陰極として、Ｍｇ：
Ａｇ、Ａｇ：Ｅｕ、Ｍｇ：Ｃｕ、Ｍｇ：Ｉｎ、及びＭ
ｇ：Ｓｎ等の合金からなる導電性被膜を、共蒸着法を用
いて２００ｎｍ程度の厚さで形成することにより、有機
薄膜ＥＬ素子が形成される。On this organic light emitting layer, as a cathode, Mg:
Ag, Ag: Eu, Mg: Cu, Mg: In, and M
An organic thin film EL element is formed by forming a conductive coating film made of an alloy such as g: Sn with a thickness of about 200 nm using a co-evaporation method.
【００１０】なお、この有機発光層と陰極との間には、
陰極からの電子注入効率を高め低電圧駆動するために、
必要に応じて、トリス（８−キノリノール）アルミニウ
ム及び１０−ヒドロキシベンゾ［ｈ］キノリン−ベリリ
ウム錯体等からなる電子注入輸送層が形成される。Between the organic light emitting layer and the cathode,
In order to increase the electron injection efficiency from the cathode and drive at a low voltage,
If necessary, an electron injecting and transporting layer made of tris (8-quinolinol) aluminum, 10-hydroxybenzo [h] quinoline-beryllium complex, etc. is formed.
【００１１】以上のように構成される有機薄膜ＥＬ素子
においては、通常、２０〜３０Ｖ以下の直流低電圧を印
加することにより、発光層に正孔と電子とが注入され、
それらが再結合することにより青色の発光が生じる。ま
た、陰極にＭｇ：Ａｇ合金を用いた素子では、１０００
ｃｄ／ｍ2 以上の輝度が得られている。In the organic thin film EL device having the above structure, holes and electrons are injected into the light emitting layer by applying a direct current low voltage of 20 to 30 V or less,
When they recombine, blue light is emitted. Further, in the element using Mg: Ag alloy for the cathode, 1000
A luminance of cd / m 2 or more is obtained.
【００１２】しかしながら、この有機薄膜ＥＬ素子に用
いられる青色発光材料の多くは、いずれもＴg が低く、
結晶化が生じ易い等の問題がある。特に、上記化学式
（４）に示すテトラフェニルブタジエンは、室温でも容
易に結晶化してしまう。However, most of the blue light emitting materials used in this organic thin film EL element have low T g ,
There is a problem that crystallization is likely to occur. In particular, the tetraphenylbutadiene represented by the above chemical formula (4) easily crystallizes even at room temperature.
【００１３】さらに、上記化学式（５）に示す化合物
は、高純度な合成が困難であり、上記化学式（５）、
（６）に示す化合物を用いて有機発光層を形成する場
合、ペリレンの濃度を精密にコントロールしてドーピン
グさせなければ、色純度の良い青色発光が得られない。
そのため、ドーピング濃度を精密に制御することが困難
となり、高い再現性を得ることができないという問題を
生ずる。Further, the compound represented by the chemical formula (5) is difficult to synthesize in high purity, and the compound represented by the chemical formula (5)
When an organic light emitting layer is formed using the compound shown in (6), blue light emission with good color purity cannot be obtained unless the concentration of perylene is precisely controlled for doping.
Therefore, it becomes difficult to precisely control the doping concentration, which causes a problem that high reproducibility cannot be obtained.
【００１４】このように、有機発光層の耐熱性が低いた
め、素子作製プロセスや素子駆動時に生ずる熱や、夏場
の自動車内等の高温条件下に晒した場合に、有機発光層
の有機発光層と隣接する有機層との溶融・混合や、膜の
結晶化による電気的短絡が生ずると問題を有している。As described above, since the heat resistance of the organic light emitting layer is low, the organic light emitting layer is an organic light emitting layer when exposed to heat generated during the device manufacturing process or driving the device and high temperature conditions such as in an automobile in the summer. There is a problem if an electric short circuit occurs due to melting and mixing of the organic layer with the adjacent organic layer and crystallization of the film.
【００１５】[0015]
【発明が解決しようとする課題】本発明は、青色に発光
し、耐熱性が高く、電気的短絡が生じにくい有機薄膜Ｅ
Ｌ素子を提供することを目的とする。DISCLOSURE OF THE INVENTION According to the present invention, an organic thin film E that emits blue light, has high heat resistance, and is unlikely to cause an electrical short circuit.
It is intended to provide an L element.
【００１６】[0016]
【課題を解決するための手段】本発明は、基板と、前記
基板上に配置され対向する電極対と、前記電極対間に設
けられた有機発光層と、を具備し、前記電極対間に形成
される層のいずれか１層が、下記一般式（１）に示す化
合物を含有することを特徴とする有機薄膜ＥＬ素子を提
供する。The present invention comprises a substrate, a pair of electrodes arranged on the substrate and facing each other, and an organic light emitting layer provided between the pair of electrodes. Provided is an organic thin film EL device, wherein any one of the formed layers contains a compound represented by the following general formula (1).
【００１７】[0017]
【化４】 [Chemical 4]
【００１８】（式中、Ｒは、アルキル基またはアリール
基を示し、Ａｒは、縮合芳香族環を含み且つ前記一般式
（１）中のＳｉに縮合芳香族環が直接結合する置換基ま
たは縮合芳香族環とベンゼン環とを含み且つ前記一般式
（１）中のＳｉに前記縮合芳香族環が前記ベンゼン環の
みを介して結合する置換基を示す。）本発明は、上記有
機薄膜ＥＬ素子において、前記電極対の一方と前記有機
発光層との間に設けられた正孔注入輸送層を具備し、前
記有機発光層が前記一般式（１）に示す化合物を含有す
ることを特徴とする。[0018] (wherein, R represents an alkyl group or an aryl group, Ar is unrealized and Formula fused aromatic rings
(1) substituent fused aromatic ring is directly bonded to Si in or
Or a condensed aromatic ring and a benzene ring
The condensed aromatic ring is replaced with the benzene ring in Si in (1).
A substituent that is bonded via a group is shown. ) In the above organic thin film EL device, the present invention comprises a hole injecting and transporting layer provided between one of the pair of electrodes and the organic light emitting layer, wherein the organic light emitting layer is represented by the general formula (1). It is characterized by containing the compound shown.
【００１９】本発明は、上記薄膜ＥＬ素子において、前
記電極対の他方と前記有機発光層との間に設けられた電
子注入輸送層を具備することを特徴とする。本発明は、
上記薄膜ＥＬ素子において、前記電極対の一方と前記有
機発光層との間に設けられた正孔注入輸送層と、前記電
極対の他方と前記有機発光層との間に設けられた電子注
入輸送層とを具備し、前記電子注入輸送層が前記一般式
（１）に示す化合物を含有することを特徴とする。The present invention is characterized in that the above-mentioned thin film EL element is provided with an electron injecting and transporting layer provided between the other of the electrode pair and the organic light emitting layer. The present invention is
In the above thin film EL device, a hole injecting and transporting layer provided between one of the electrode pair and the organic light emitting layer, and an electron injecting and transporting layer provided between the other of the electrode pair and the organic light emitting layer. A layer, and the electron injecting and transporting layer contains the compound represented by the general formula (1).
【００２０】[0020]
【発明の実施の形態】以下、本発明の有機薄膜ＥＬ素子
について、図面を参照しながら説明する。図１に、本発
明の一態様に係る有機薄膜ＥＬ素子の一断面図を示す。
図１で、基板１上には、陽極として電極２が形成され、
電極２上には、正孔注入輸送層３、有機発光層４、及び
陰極として電極５が順次積層されて有機薄膜ＥＬ素子が
構成されている。基板１上には、電源６の陰極に配線７
を介して電気的に接続された導電部８が形成されてお
り、導電部８は、電極５に電気的に接続されている。ま
た、電源６の陽極は、配線９を介して電極２に電気的に
接続されている。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, an organic thin film EL element of the present invention will be described with reference to the drawings. FIG. 1 shows a cross-sectional view of an organic thin film EL element according to one aspect of the present invention.
In FIG. 1, an electrode 2 is formed on a substrate 1 as an anode,
A hole injecting and transporting layer 3, an organic light emitting layer 4, and an electrode 5 as a cathode are sequentially laminated on the electrode 2 to form an organic thin film EL element. On the substrate 1, the wiring 7 is connected to the cathode of the power supply 6.
A conductive portion 8 electrically connected via is formed, and the conductive portion 8 is electrically connected to the electrode 5. Further, the anode of the power source 6 is electrically connected to the electrode 2 via the wiring 9.
【００２１】さらに、この有機薄膜ＥＬ素子の電極５上
には、封止層１０が形成され、この封止層１０上に接着
性材料１１で封止板１２を接着することにより、有機薄
膜ＥＬ素子が封止されている。Further, a sealing layer 10 is formed on the electrode 5 of the organic thin film EL element, and a sealing plate 12 is adhered to the sealing layer 10 with an adhesive material 11 to form the organic thin film EL. The element is sealed.
【００２２】図１では、正孔注入輸送層が１層のみ形成
されているが、正孔注入輸送層を複数積層してもよい。
図２に、本発明の他の態様に係る有機薄膜ＥＬ素子の一
断面図を示す。Although only one hole injecting and transporting layer is formed in FIG. 1, a plurality of hole injecting and transporting layers may be laminated.
FIG. 2 shows a cross-sectional view of an organic thin film EL element according to another aspect of the present invention.
【００２３】図２に示す有機薄膜ＥＬ素子では、図１に
示す有機薄膜ＥＬ素子の正孔注入輸送層３の代わりに、
電極２上に、第１の正孔注入輸送層１３、第２の正孔注
入輸送層１４、及び第３の正孔注入輸送層１５が順次積
層されている。In the organic thin film EL element shown in FIG. 2, instead of the hole injecting and transporting layer 3 of the organic thin film EL element shown in FIG.
A first hole injecting / transporting layer 13, a second hole injecting / transporting layer 14, and a third hole injecting / transporting layer 15 are sequentially stacked on the electrode 2.
【００２４】本発明の有機薄膜ＥＬ素子は、電子注入輸
送層が設けられていてもよい。図３に、本発明のさらに
他の態様に係る有機薄膜ＥＬ素子の一断面図を示す。図
３に示す有機薄膜ＥＬ素子は、図２に示す素子の有機発
光層４と電極５との間に、電子注入輸送層１６が形成さ
れた構造を有している。The organic thin film EL device of the present invention may be provided with an electron injecting and transporting layer. FIG. 3 shows a cross-sectional view of an organic thin film EL element according to yet another aspect of the present invention. The organic thin film EL element shown in FIG. 3 has a structure in which an electron injecting and transporting layer 16 is formed between the organic light emitting layer 4 and the electrode 5 of the element shown in FIG.
【００２５】上記図１〜図３に示す本発明の有機薄膜Ｅ
Ｌ素子は、正孔注入輸送層、有機発光層、及び電子注入
輸送層の少なくとも１層に、上記一般式（１）に示す化
合物を含有することを特徴としている。The organic thin film E of the present invention shown in FIGS.
The L element is characterized in that at least one layer of the hole injecting and transporting layer, the organic light emitting layer, and the electron injecting and transporting layer contains the compound represented by the general formula (1).
【００２６】一般式（１）に示す化合物において、Ｒは
アルキル基及びアリール基を示しており、Ａｒは縮合芳
香族環を含み且つ一般式（１）中のＳｉに縮合芳香族環
が直接結合する置換基または縮合芳香族環とベンゼン環
とを含み且つ一般式（１）中のＳｉに縮合芳香族環がベ
ンゼン環のみを介して結合する置換基を示している。Ｒ
に用いられるアルキル基としては、メチル基、エチル
基、及びイソプロピル基等を挙げることができ、アリー
ル基としては、フェニル基及びトリル基等を挙げること
ができる。[0026] In the compounds represented by the general formula (1), R is an alkyl group and is an aryl group, Ar is a fused aromatic ring to Si in unrealized and formula fused aromatic ring (1)
Substituents or fused aromatic rings and benzene rings that are directly bonded to each other
And a condensed aromatic ring is included in Si in the general formula (1).
The substituents are shown which are bonded only via the Nzen ring . R
Examples of the alkyl group used for include a methyl group, ethyl group, isopropyl group, and the like, and examples of the aryl group include a phenyl group, a tolyl group, and the like.
【００２７】Ａｒに用いられる縮合芳香族環を含む置換
基としては、４−アントリルフェニル基、ナフチル基、
アントリル基、置換アントリル基、フェナントリル基、
アクリジニル基、フェナントロリニル基等を挙げること
ができる。また、上記一般式（１）に示す化合物とし
て、下記化学式（７）〜（１７）に示す化合物を挙げる
ことができる。As the substituent containing a condensed aromatic ring used for Ar, 4-anthrylphenyl group, naphthyl group,
Anthryl group, substituted anthryl group, phenanthryl group,
Examples thereof include an acridinyl group and a phenanthrolinyl group. Further, examples of the compound represented by the general formula (1) include compounds represented by the following chemical formulas (7) to (17).
【００２８】[0028]
【化５】 [Chemical 5]
【００２９】[0029]
【化６】 [Chemical 6]
【００３０】[0030]
【化７】 [Chemical 7]
【００３１】上記化学式（７）に示す化合物は、融点が
２６９℃、Ｔg が１０３℃であって（ＤＳＣ、２０℃／
ｍｉｎで測定）、上記化学式（８）〜（１７）に示す化
合物も、ほぼ同様の融点及びＴg を有している。このよ
うに、これら一般式（１）に示す化合物は、融点及びＴ
g が高いため、素子の作製時の熱や駆動時に生じる熱に
晒されても、隣接する有機薄膜層との混合や、結晶化は
生じない。すなわち、良好な耐熱性を有する有機薄膜を
形成することができるのである。The compound represented by the above chemical formula (7) has a melting point of 269 ° C. and a T g of 103 ° C. (DSC, 20 ° C. /
The compounds represented by the chemical formulas (8) to (17) also have almost the same melting point and T g . Thus, the compound represented by the general formula (1) has a melting point and T
Since the g is high, even when exposed to heat during device fabrication or heat generated during driving, neither mixing with adjacent organic thin film layers nor crystallization occurs. That is, it is possible to form an organic thin film having good heat resistance.
【００３２】また、上記一般式（１）に示す化合物は、
シリコン原子に２つの大きなＡｒ基が結合しているた
め、立体的に嵩高い分子形状となっている。そのため、
この化合物を用いて成膜する場合、アモルファスへの制
御が容易であり、かつ、形成された膜は平滑で結晶化は
生じ難い。The compound represented by the general formula (1) is
Since two large Ar groups are bonded to the silicon atom, the molecular shape is sterically bulky. for that reason,
When a film is formed using this compound, it is easy to control it to be amorphous, and the formed film is smooth and crystallization hardly occurs.
【００３３】さらに、一般式（１）に示す化合物で薄膜
を形成した場合、透明な膜が形成される。このような透
明な薄膜は、可視光の吸収が非常に少なく、有機薄膜Ｅ
Ｌ素子の材料として適している。Furthermore, when a thin film is formed from the compound represented by the general formula (1), a transparent film is formed. Such a transparent thin film has very little absorption of visible light,
Suitable as a material for L element.
【００３４】したがって、上記一般式（１）に示す化合
物を用いることにより、耐熱性が高く結晶化が生じにく
い、すなわち、電気的短絡が生じにくい、有機薄膜ＥＬ
素子に用いられる有機薄膜を作製することが可能となる
のである。Therefore, by using the compound represented by the general formula (1), the organic thin film EL has high heat resistance and is less likely to be crystallized, that is, less likely to cause an electrical short circuit.
It is possible to produce an organic thin film used for the device.
【００３５】この有機薄膜としては、上述のように、正
孔注入輸送層、有機発光層、及び電子注入輸送層が挙げ
られるが、一般式（１）に示す化合物は、いずれも青色
〜青緑色に発光する有機蛍光体として用いることができ
るので、特に、一般式（１）に示す化合物を有機発光層
に用いることが好ましい。Examples of the organic thin film include a hole injecting and transporting layer, an organic light emitting layer, and an electron injecting and transporting layer as described above. The compounds represented by the general formula (1) are all blue to blue green. It is particularly preferable to use the compound represented by the general formula (1) in the organic light emitting layer because it can be used as an organic phosphor that emits light.
【００３６】このように、上記一般式（１）に示す化合
物を用いて有機発光層を形成することにより、耐熱性が
高く、電気的短絡が生じにくい青色発光の有機薄膜ＥＬ
素子を形成することが可能となる。As described above, by forming the organic light emitting layer using the compound represented by the general formula (1), a blue light emitting organic thin film EL having high heat resistance and being less likely to cause an electrical short circuit.
It becomes possible to form an element.
【００３７】また、一般式（１）に示す化合物は、Ｓｉ
原子に結合する２つのＡｒ基がＳｉ原子を通じて共役す
る。そのため、２つのＡｒ基が炭素に結合した分子に比
べ、分子のイオン化エネルギーが小さくなる。よって、
２つのＡｒ基が炭素に結合した分子で発光層を形成した
場合には、２つのＡｒ基がＳｉに結合した一般式（１）
に示す化合物は、ＩＴＯ透明陽極と発光層との間に配置
されることにより、正孔注入輸送層として機能する。The compound represented by the general formula (1) is Si
Two Ar groups attached to the atom are conjugated through the Si atom. Therefore, the ionization energy of the molecule is smaller than that of the molecule in which two Ar groups are bonded to carbon. Therefore,
When the light emitting layer is formed by a molecule in which two Ar groups are bonded to carbon, the general formula (1) in which two Ar groups are bonded to Si is used.
The compound shown in 1 functions as a hole injecting and transporting layer by being arranged between the ITO transparent anode and the light emitting layer.
【００３８】したがって、上記一般式（１）に示す化合
物が、エネルギーレベル的に適当な関係にある発光層に
対して正孔注入輸送層に用いることができ、耐熱性が高
く、電気的短絡が生じにくい有機薄膜ＥＬ素子を形成す
ることが可能となる。同様に、後述するようにエネルギ
ーレベル的に適当な関係にある発光層に対しては、電子
注入輸送層として機能させることも可能である。なお、
上記一般式（１）に示す化合物は、下記化学反応式
（１）に示すようにして合成することができる。Therefore, the compound represented by the above general formula (1) can be used in the hole injecting and transporting layer with respect to the light emitting layer having an appropriate energy level relationship, has high heat resistance, and causes no electrical short circuit. It is possible to form an organic thin film EL element that is unlikely to occur. Similarly, as will be described later, it is also possible to function as an electron injecting and transporting layer for a light emitting layer having an appropriate energy level relationship. In addition,
The compound represented by the general formula (1) can be synthesized as shown in the following chemical reaction formula (1).
【００３９】[0039]
【化８】 [Chemical 8]
【００４０】［式中、Ｒ及びＡｒは、上記一般式（１）
のＲ及びＡｒと同様である。］
これら化合物を用いて有機薄膜を形成する場合、真空蒸
着法、スピンコート法、ディップコート法、及びロール
コート法等の方法を用いることができる。真空蒸着法で
成膜する場合は、上記一般式（１）に示す置換基Ｒを適
切に選択することにより、分子量を調節して所望の蒸気
圧を得ることができる。[In the formula, R and Ar are the above general formula (1)
And R and Ar. When forming an organic thin film using these compounds, methods such as a vacuum vapor deposition method, a spin coating method, a dip coating method, and a roll coating method can be used. When the film is formed by the vacuum vapor deposition method, a desired vapor pressure can be obtained by adjusting the molecular weight by appropriately selecting the substituent R represented by the general formula (1).
【００４１】以下、本発明の有機薄膜ＥＬ素子につい
て、より詳細に説明する。本発明の有機薄膜ＥＬ素子で
用いられる基板としては、金属基板、半導体基板、及び
絶縁性基板を挙げることができる。Hereinafter, the organic thin film EL device of the present invention will be described in more detail. Examples of the substrate used in the organic thin film EL element of the present invention include a metal substrate, a semiconductor substrate, and an insulating substrate.
【００４２】この金属基板を構成する材料としては、基
板を陽極とする場合には、金、プラチナ、パラジウム及
びニッケル等の仕事関数が４．６ｅＶ以上の金属や、こ
れら金属が放熱性の良い銅やアルミニウムの金属基板上
に成膜された基板を挙げることができ、基板を陰極とす
る場合には、アルミニウム基板や銅基板上に仕事関数が
２．５〜４ｅＶのマグネシウム合金やアルミニウム合金
を成膜した基板を挙げることができる。基板を金属基板
で構成する場合、この金属基板上に電極を形成する必要
はない。As a material for forming the metal substrate, when the substrate is used as an anode, a metal having a work function of 4.6 eV or more, such as gold, platinum, palladium, and nickel, or copper having good heat dissipation is used. And a substrate formed on a metal substrate of aluminum. When the substrate is used as a cathode, a magnesium alloy or an aluminum alloy having a work function of 2.5 to 4 eV is formed on an aluminum substrate or a copper substrate. Mention may be made of filmed substrates. When the substrate is composed of a metal substrate, it is not necessary to form electrodes on this metal substrate.
【００４３】半導体基板を構成する材料としては、シリ
コン、ガリウムリン、アモルファス炭化シリコン、及び
酸化銅等の半導体を挙げることができる。半導体基板を
構成する半導体の仕事関数は、４．６ｅＶ以上であるこ
とが好ましい。仕事関数が４．６ｅＶ以上の場合、通
常、イオン化エネルギーが５．０〜６．０ｅＶである有
機正孔注入輸送層に対して正孔注入障壁が小さくなり、
低い電圧で正孔の注入が可能となる。Examples of the material forming the semiconductor substrate include semiconductors such as silicon, gallium phosphide, amorphous silicon carbide, and copper oxide. The work function of the semiconductor forming the semiconductor substrate is preferably 4.6 eV or more. When the work function is 4.6 eV or more, the hole injection barrier is usually small with respect to the organic hole injection transport layer having an ionization energy of 5.0 to 6.0 eV,
Holes can be injected at a low voltage.
【００４４】絶縁性基板としては、酸化膜付きシリコン
基板や窒化膜付きシリコン基板等の不透明絶縁性基板、
及びガラスやポリエーテルスルホン等のプラスチックフ
ィルム等の透明絶縁性基板を挙げることができる。As the insulating substrate, an opaque insulating substrate such as a silicon substrate with an oxide film or a silicon substrate with a nitride film,
And transparent insulating substrates such as glass and plastic films such as polyethersulfone.
【００４５】この絶縁性基板上に陽極として形成される
電極としては、不透明電極、半透明電極、及び透明電極
を挙げることができる。不透明電極を構成する材料とし
ては、上述の金属基板や半導体基板を構成する材料を挙
げることができる。Examples of the electrode formed as an anode on this insulating substrate include an opaque electrode, a semitransparent electrode, and a transparent electrode. Examples of the material forming the opaque electrode include the materials forming the above-described metal substrate and semiconductor substrate.
【００４６】また、半透明電極としては、金やプラチナ
を薄く蒸着することにより形成される導電膜、及びポリ
アニリン、ポリピロール及びポリチオフェン等の高分子
からなる導電膜等を挙げることができ、透明電極として
は、ＩＴＯ（仕事関数４．６〜４．８ｅＶ）や酸化亜鉛
アルミニウムの非晶質または微結晶の透明導電膜を挙げ
ることができる。Examples of the semitransparent electrode include a conductive film formed by thinly depositing gold or platinum, a conductive film made of a polymer such as polyaniline, polypyrrole, and polythiophene. Examples thereof include ITO (work function 4.6 to 4.8 eV) and an amorphous or microcrystalline transparent conductive film of zinc aluminum oxide.
【００４７】基板として透明絶縁性基板を用い、陽極を
透明電極または半透明電極とした場合、この基板側から
表示を行うことができる。この場合、透明絶縁性基板の
少なくとも一方の主面に、コントラストや耐性向上のた
めに、着色してもよく、円偏光フィルタ、多層膜反射防
止フィルタ、紫外線吸収フィルタ、ＲＧＢカラーフィル
タ、蛍光波長変換フィルタ、及びシリカコーティング等
を設けてもよい。When a transparent insulating substrate is used as the substrate and the anode is a transparent electrode or a semitransparent electrode, display can be performed from this substrate side. In this case, at least one main surface of the transparent insulating substrate may be colored in order to improve contrast and durability, and may be circularly polarized filter, multilayer antireflection filter, ultraviolet absorption filter, RGB color filter, fluorescence wavelength conversion. A filter, silica coating, etc. may be provided.
【００４８】また、この基板側から表示を行う場合、透
明絶縁性基板上に形成する電極は、表面抵抗が１〜５０
Ω／□で、可視光線透過率が８０％以上の透明電極であ
ることが好ましい。When the display is performed from this substrate side, the electrodes formed on the transparent insulating substrate have a surface resistance of 1 to 50.
It is preferable that the transparent electrode has a visible light transmittance of 80% or more in Ω / □.
【００４９】低抵抗化のために、銀、銅、及び銀と銅と
の合金からなる１０ｎｍ程度の厚さの層を、ＩＴＯ、イ
ンジウム亜鉛複合酸化物、酸化チタン、酸化錫等からな
る非晶質または微結晶の透明導電膜で挟んだ構造の膜
を、透明電極として用いてもよい。これらの透明電極
は、真空蒸着法やスパッタリング法等の方法により、上
記基板上に形成される。In order to reduce the resistance, a layer having a thickness of about 10 nm made of silver, copper, and an alloy of silver and copper is formed of an amorphous material made of ITO, indium zinc composite oxide, titanium oxide, tin oxide or the like. A film having a structure sandwiched between transparent conductive films of high quality or microcrystals may be used as the transparent electrode. These transparent electrodes are formed on the substrate by a method such as a vacuum evaporation method or a sputtering method.
【００５０】なお、上述の透明電極を用いた有機薄膜Ｅ
Ｌ素子を、単純マトリクス駆動ディスプレイとして用い
る場合、透明電極のラインに接して、Ｃｕ、Ａｌ等の低
抵抗率金属からなる金属バスラインを設け、より低抵抗
化することが望ましい。The organic thin film E using the above-mentioned transparent electrode
When the L element is used as a simple matrix drive display, it is desirable to provide a metal bus line made of a low resistivity metal such as Cu or Al in contact with the transparent electrode line to further reduce the resistance.
【００５１】本発明の有機薄膜ＥＬ素子において、正孔
注入輸送層に用いられる材料としては、上記化学式
（１）〜（３）に示す正孔輸送材料、ＣｕＰｃ、塩素化
銅フタロシアニン、テトラ（ｔ−ブチル）銅フタロシア
ニン等の金属フタロシアニン類及び無金属フタロシアニ
ン類、キナクリドン等の低分子正孔注入輸送材料、ポリ
（パラ−フェニレンビニレン）及びポリアニリン等の高
分子正孔輸送材料、及び、その他既存の正孔注入輸送材
料を挙げることができる。In the organic thin film EL device of the present invention, as the material used for the hole injecting and transporting layer, the hole transporting materials represented by the above chemical formulas (1) to (3), CuPc, chlorinated copper phthalocyanine, tetra (t) are used. -Butyl) copper phthalocyanine and other metal phthalocyanines and metal-free phthalocyanines, quinacridone and other low-molecular hole injecting and transporting materials, poly (para-phenylene vinylene) and polyaniline and other polymeric hole transporting materials, and other existing A hole injection transport material can be mentioned.
【００５２】また、上記一般式（１）に示す化合物も、
適当なエネルギーレベルの関係にある発光層に対して正
孔注入輸送材料として機能することも可能である。例え
ば、イオン化エネルギー（Ｉｐ）が６ｅＶ以上である発
光層に対して、仕事関数が４．９ｅＶのＩＴＯから正孔
を注入する場合、Ｉｐ５．０〜５．５ｅＶの上記一般式
（１）〜（３）に示す化合物を正孔注入輸送材料として
用いることができる。The compound represented by the general formula (1) is also
It is also possible to function as a hole injecting / transporting material for a light emitting layer having a proper energy level relationship. For example, in the case of injecting holes from ITO having a work function of 4.9 eV into a light emitting layer having an ionization energy (Ip) of 6 eV or more, the above general formulas (1) to (1) to Ip of 5.0 to 5.5 eV are used. The compound shown in 3) can be used as the hole injecting / transporting material.
【００５３】本発明の正孔注入輸送層は、上述のよう
に、エネルギーレベルの調整、劣化防止、色調の補正の
目的で、正孔注入輸送材料からなる複数の膜が積層され
た積層構造であってもよい。As described above, the hole injecting and transporting layer of the present invention has a laminated structure in which a plurality of films of the hole injecting and transporting material are laminated for the purpose of adjusting the energy level, preventing deterioration, and correcting the color tone. It may be.
【００５４】例えば、正孔注入輸送層を３層構造とし、
陽極側から順に、第１の正孔注入輸送層、第２の正孔注
入輸送層、第３の正孔注入輸送層とした場合、これら正
孔注入輸送層、有機発光層、及び陽極の仕事関数または
イオン化エネルギーの値を、陽極＜第１の正孔注入輸送
層＜第２の正孔注入輸送層＜第３の正孔注入輸送層＜有
機発光層の順に制御することが好ましい。For example, the hole injecting and transporting layer has a three-layer structure,
When the first hole injecting and transporting layer, the second hole injecting and transporting layer, and the third hole injecting and transporting layer are formed in this order from the anode side, the work of these hole injecting and transporting layer, organic light emitting layer, and anode is performed. It is preferable to control the value of the function or the ionization energy in the order of anode <first hole injecting / transporting layer <second hole injecting / transporting layer <third hole injecting / transporting layer <organic light emitting layer.
【００５５】このように積層すると、陽極と有機発光層
間のエネルギーレベルの段差が小さくなり、有機発光層
への正孔注入効率が向上し、低電圧でＥＬ発光を得るこ
とができる。By stacking in this manner, the difference in energy level between the anode and the organic light emitting layer is reduced, the efficiency of hole injection into the organic light emitting layer is improved, and EL light emission can be obtained at a low voltage.
【００５６】正孔注入輸送層の積層数に特に制限はな
く、種類の異なる正孔注入輸送材料同士を混合、または
積層して用いることもできる。この正孔注入輸送層は、
真空蒸着法等により形成することができる。また、正孔
注入輸送材料をトルエンやクロロホルム等の有機溶媒に
溶かし、スピンコート法、ディップコート法、及びロー
ルコート法等の方法により、基板上に塗布・成膜するこ
とができる。The number of layers of the hole injecting and transporting layer is not particularly limited, and hole injecting and transporting materials of different types may be mixed or laminated and used. This hole injecting and transporting layer is
It can be formed by a vacuum vapor deposition method or the like. Further, the hole injecting and transporting material can be dissolved in an organic solvent such as toluene or chloroform and then applied / formed on the substrate by a method such as a spin coating method, a dip coating method, and a roll coating method.
【００５７】本発明の有機薄膜ＥＬ素子において、有機
発光層とは、素子への電圧の印加時に、可視光領域で強
い蛍光を発する任意の有機蛍光体を１種以上含む層であ
る。この有機蛍光体が、固体状態で強い蛍光を有し平滑
な膜の形成が可能であれば、有機蛍光体のみで有機発光
層を構成することが可能である。In the organic thin film EL device of the present invention, the organic light emitting layer is a layer containing one or more kinds of arbitrary organic phosphors that emit strong fluorescence in the visible light region when a voltage is applied to the device. If the organic phosphor has strong fluorescence in the solid state and can form a smooth film, the organic light emitting layer can be composed of only the organic phosphor.
【００５８】しかしながら、固体状態で蛍光が消光した
り、平滑な膜の形成が困難な場合は、有機蛍光体を、正
孔注入輸送材料、電子注入輸送材料、または所定の樹脂
バインダと混合した混合物で有機発光層を構成すること
ができる。However, when fluorescence is quenched in the solid state or it is difficult to form a smooth film, a mixture of an organic phosphor with a hole injecting / transporting material, an electron injecting / transporting material, or a predetermined resin binder is used. The organic light emitting layer can be composed of.
【００５９】本発明の有機薄膜ＥＬ素子において、有機
発光層に用いられる有機蛍光体としては、上記一般式
（１）に示す化合物、サリチル酸塩、ピレン、コロネ
ン、ペリレン、ルブレン、テトラフェニルブタジエン、
９，１０−ビス（フェニルエチニル）アントラセン、８
−キノリノラートリチウム、Ａｌｑ、トリス（５，７−
ジクロロ，８−キノリノラート）アルミニウム錯体、ト
リス（５−クロロ−８−キノリノラート）アルミニウム
錯体、ビス（８−キノリノラート）亜鉛錯体、トリス
（５−フルオロ−８−キノリノラート）アルミニウム錯
体、トリス（４−メチル−５−トリフルオロメチル−８
−キノリノラート）アルミニウム錯体、トリス（４−メ
チル−５−シアノ−８−キノリノラート）アルミニウム
錯体、ビス（２−メチル−５−トリフルオロメチル−８
−キノリノラート）（４−シアノフェニルフェノラー
ト）、ビス（２−メチル−５−シアノ−８−キノリノラ
ート）（４−シアノフェニルフェノラート）アルミニウ
ム錯体、トリス（８−キノリノラート）スカンジウム錯
体、ビス［８−（パラ−トシル）アミノキノリン］亜鉛
錯体及びカドミウム錯体、１，２，３，４−テトラフェ
ニルシクロペンタジエン、ペンタフェニルシクロペンタ
ジエン、ポリ−２，５−ジヘプリルオキシ−ｐ−フェニ
レンビニレン、特開平４−３１４８８号公報に記載され
た蛍光体、米国特許第５，１４１，６７１号公報に記載
された蛍光体、米国特許第４，７６９，２９２号公報に
記載された蛍光体、Ｎ，Ｎ’−ジアリール置換ピロロピ
ロール化合物等を挙げることができる。In the organic thin film EL device of the present invention, as the organic phosphor used in the organic light emitting layer, the compound represented by the general formula (1), salicylate, pyrene, coronene, perylene, rubrene, tetraphenylbutadiene,
9,10-bis (phenylethynyl) anthracene, 8
-Lithium quinolinolato, Alq, tris (5,7-
Dichloro, 8-quinolinolato) aluminum complex, tris (5-chloro-8-quinolinolato) aluminum complex, bis (8-quinolinolato) zinc complex, tris (5-fluoro-8-quinolinolato) aluminum complex, tris (4-methyl-) 5-trifluoromethyl-8
-Quinolinolato) aluminum complex, tris (4-methyl-5-cyano-8-quinolinolato) aluminum complex, bis (2-methyl-5-trifluoromethyl-8)
-Quinolinolate) (4-cyanophenylphenolate), bis (2-methyl-5-cyano-8-quinolinolate) (4-cyanophenylphenolate) aluminum complex, tris (8-quinolinolate) scandium complex, bis [8- (Para-tosyl) aminoquinoline] zinc complex and cadmium complex, 1,2,3,4-tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, poly-2,5-dihepryloxy-p-phenylenevinylene, JP-A-4-31488 US Pat. No. 5,141,671 phosphors, US Pat. No. 4,769,292 phosphors, N, N′-diaryl substitution. Examples thereof include a pyrrolopyrrole compound.
【００６０】本発明の有機薄膜ＥＬ素子において、有機
発光層は、種類の異なる有機蛍光体を混合して構成する
ことができる。上記一般式（１）に示す化合物を青色発
光ドーパントとして、他の適当な有機蛍光体をホストと
して、これらを混合して用いてもよい。また、有機発光
層を、種類の異なる有機蛍光体からなる複数の膜を積層
した積層構造としてもよい。In the organic thin film EL device of the present invention, the organic light emitting layer can be formed by mixing different kinds of organic phosphors. The compound represented by the general formula (1) may be used as a blue light emitting dopant, and another suitable organic phosphor may be used as a host, and these may be mixed and used. Further, the organic light emitting layer may have a laminated structure in which a plurality of films made of different kinds of organic phosphors are laminated.
【００６１】この有機発光層は、単層構造においても、
積層構造においても、１００ｎｍ以下であることが好ま
しく、５〜５０ｎｍであることがより好ましい。また、
この有機発光層に、米国ラムダフィズィック社やイース
トマンコダック社から市販されているクマリン系、キナ
クリドン系、ペリレン系、及びピラン系の有機蛍光体を
ゲスト発光体としてドーピングしてもよい。This organic light emitting layer has a single-layer structure,
Also in the laminated structure, the thickness is preferably 100 nm or less, and more preferably 5 to 50 nm. Also,
The organic light-emitting layer may be doped with a coumarin-based, quinacridone-based, perylene-based, or pyran-based organic fluorescent material commercially available from Lambda Fizzic Co., Ltd. or Eastman Kodak Co., Ltd. as a guest light-emitting body.
【００６２】このように、種類の異なる有機蛍光体を用
いることにより、発光波長の変換、発光波長領域の拡
大、及び発光効率の向上を図ることができる。なお、種
類の異なる有機蛍光体を用いる場合、少なくとも１種の
有機蛍光体が可視光領域で蛍光を発するものであれば、
他の有機蛍光体は、赤外域または紫外域で蛍光を発する
ものでもよい。As described above, by using different kinds of organic phosphors, the emission wavelength can be converted, the emission wavelength region can be expanded, and the emission efficiency can be improved. When different kinds of organic phosphors are used, if at least one kind of organic phosphor emits fluorescence in the visible light region,
The other organic phosphor may be one that emits fluorescence in the infrared region or the ultraviolet region.
【００６３】この有機発光層は、上述の有機蛍光体を、
真空蒸着法、累積膜法、または適当な樹脂バインダ中に
分散させてスピンコートすること等の方法でコーティン
グすることにより形成される。This organic light-emitting layer contains the above-mentioned organic phosphor.
It is formed by coating by a vacuum vapor deposition method, a cumulative film method, or a method such as dispersing in an appropriate resin binder and spin coating.
【００６４】本発明の有機薄膜ＥＬ素子において、有機
発光層上に陰極として設けられる電極は、低仕事関数の
材料で構成されることが好ましい。この低仕事関数の材
料としては、Ｍｇ及びＡｌ等の単体の金属、及び、Ｌ
ｉ、Ｍｇ、Ｃａ、Ａｒ、Ｌａ、Ｃｅ、Ｅｒ、Ｅｕ、Ｓ
ｃ、Ｙ、及びＹｂ等の元素を１種以上含有する合金等を
挙げることができる。In the organic thin film EL device of the present invention, the electrode provided as the cathode on the organic light emitting layer is preferably made of a material having a low work function. As the low work function material, simple metals such as Mg and Al, and L
i, Mg, Ca, Ar, La, Ce, Er, Eu, S
Examples thereof include alloys containing one or more elements such as c, Y, and Yb.
【００６５】これらの低仕事関数の材料を陰極に用いる
と、電子注入が効果的に行なわれ、特に、上記合金を用
いた場合は、低仕事関数と安定性とを両立させることが
できる。When these materials having a low work function are used for the cathode, electron injection is effectively performed, and particularly when the above alloy is used, both a low work function and stability can be achieved.
【００６６】また、陰極の厚さに特に制限はないが、陰
極を５〜２０ｎｍの厚さに形成すると、十分な可視光の
透過率が得られ、陰極側を表示面とすることができる。
上述の陰極は、用いる材料に応じて、抵抗加熱蒸着法、
電子ビーム蒸着法、反応性蒸着法、及びイオンプレーテ
ィング法等を用いたり、合金ターゲット等を用いてスパ
ッタリング法等により形成することができる。Although the thickness of the cathode is not particularly limited, when the cathode is formed to have a thickness of 5 to 20 nm, sufficient visible light transmittance can be obtained and the cathode side can be used as the display surface.
The cathode is a resistance heating vapor deposition method, depending on the material used,
It can be formed by using an electron beam vapor deposition method, a reactive vapor deposition method, an ion plating method, or the like, or a sputtering method using an alloy target or the like.
【００６７】この陰極を多成分合金で構成する場合は、
抵抗加熱法により１０-5Ｔｏｒｒオーダー以下の真空下
で、成分ごとに別々の蒸着源から、水晶振動子式膜厚計
でモニターしながら共蒸着法により形成するか、或い
は、合金材料を少量ずつフラッシュ蒸着することにより
形成することができる。When this cathode is made of a multi-component alloy,
It is formed by a co-evaporation method by a resistance heating method under a vacuum of the order of 10 -5 Torr or less and from a separate evaporation source for each component while monitoring it with a crystal oscillator type film thickness meter, or an alloy material is added little by little. It can be formed by flash vapor deposition.
【００６８】有機薄膜ＥＬ素子を、単純マトリクス駆動
ディスプレイとし、陰極をストライプ状に形成する必要
がある場合には、スリット状に穴の開いたマスクを基板
に密着させて蒸着するか、陰極形成部全面に蒸着した
後、ウェットエッチング法、レーザーアブレーション法
や、イオンビームエッチング法や、リアクティブエッチ
ング法等により、陰極金属のパターニングを行うことに
より、形成することができる。When the organic thin film EL device is used as a simple matrix drive display and the cathode needs to be formed in a stripe shape, a mask having a slit-like hole is brought into close contact with the substrate for vapor deposition, or the cathode forming portion is used. After vapor deposition on the entire surface, the cathode metal can be patterned by a wet etching method, a laser ablation method, an ion beam etching method, a reactive etching method, or the like.
【００６９】本発明の有機薄膜ＥＬ素子において、有機
発光層と陰極との間に、電子注入輸送層が設けられてい
ることが好ましい。電子注入輸送層に用いられる材料
は、電子移動度が大きく、ＬＵＭＯの状態密度が大き
く、ＬＵＭＯのエネルギーレベルが有機蛍光体のＬＵＭ
Ｏのエネルギーレベルと同程度から陰極材料のフェルミ
レベル（仕事関数）の間にあり、イオン化エネルギーが
有機蛍光体より大きく、成膜性がよいことが必要であ
る。In the organic thin film EL element of the present invention, it is preferable that an electron injecting and transporting layer is provided between the organic light emitting layer and the cathode. The material used for the electron injecting and transporting layer has a large electron mobility, a large LUMO density of states, and an LUMO energy level of LUM of the organic phosphor.
It is necessary that it be between the same level as the energy level of O and the Fermi level (work function) of the cathode material, have a larger ionization energy than the organic phosphor, and have good film forming properties.
【００７０】このような電子注入輸送層を設けると、有
機発光層への電子注入効率を高め、正孔が陰極へ到達す
るのを抑制することが期待できる。電子注入輸送層に用
いる材料として、上記一般式（１）に示す化合物を用い
る場合、この化合物と有機蛍光体とが、上記条件を満た
す必要がある。By providing such an electron injecting and transporting layer, it can be expected that the efficiency of injecting electrons into the organic light emitting layer is increased and that holes are prevented from reaching the cathode. When the compound represented by the general formula (1) is used as the material used for the electron injecting and transporting layer, the compound and the organic phosphor must satisfy the above conditions.
【００７１】電子注入輸送層に用いられる材料として
は、上記一般式（１）に示す化合物のほかに、ＢＰＢＤ
及び２，５−ビス（１−ナフチル）−１，３，４−オキ
サジアゾール等を用いることができる。As the material used for the electron injecting and transporting layer, in addition to the compound represented by the above general formula (1), BPBD
And 2,5-bis (1-naphthyl) -1,3,4-oxadiazole and the like can be used.
【００７２】また、浜田らが開示しているオキサジアゾ
ール誘導体（日本化学会誌、１５４０頁、１９９１年）
やビス（１０−ヒドロキシベンゾ［ｈ］キノリノラー
ト）ベリリウム錯体、及び特開平７−９０２６０号公報
で開示されているトリアゾール化合物等を用いることが
できる。The oxadiazole derivative disclosed by Hamada et al. (Journal of the Chemical Society of Japan, page 1540, 1991)
And bis (10-hydroxybenzo [h] quinolinolato) beryllium complex, and the triazole compounds disclosed in JP-A-7-90260 can be used.
【００７３】さらに、Ｍａｒｋｏ Ｓｔｒｕｋｅｌｊら
がサイエンス誌第２６７巻１９６９頁（１９９５年）で
開示している、ポリ（ｐ−フェニレンビニレン）発光層
上に設けられた１，２−ビス（３−ヒドロキシ）フェニ
ル−４−（３−トリフルオロメチルフェニル）トリアゾ
ールとデカフルオロビフェニルとの脱フッ化水素縮合ポ
リマー等の化合物や、炭化シリコン、アモルファスシリ
コン等の無機半導体や光導電性材料等を用いることがで
きる。Furthermore, 1,2-bis (3-hydroxy) provided on a poly (p-phenylene vinylene) light-emitting layer disclosed by Marko Strukelj et al. In Science, Vol. 267, p. 1969 (1995). A compound such as a dehydrofluorination condensation polymer of phenyl-4- (3-trifluoromethylphenyl) triazole and decafluorobiphenyl, an inorganic semiconductor such as silicon carbide or amorphous silicon, or a photoconductive material can be used. .
【００７４】また、有機発光層を、ホスト蛍光体中にゲ
スト蛍光体をドーピングした構成とする場合、ホスト蛍
光体を電子注入輸送材料として用いることも可能であ
る。有機薄膜ＥＬ素子を、陰極側から表示が行われる構
成とする場合、この電子注入輸送層は、少なくとも有機
蛍光体の蛍光波長領域において、実質的に透明である必
要がある。When the organic light emitting layer has a structure in which the guest phosphor is doped in the host phosphor, the host phosphor can be used as the electron injecting and transporting material. When the organic thin film EL element is configured to display from the cathode side, the electron injecting and transporting layer needs to be substantially transparent at least in the fluorescence wavelength region of the organic phosphor.
【００７５】電子注入輸送層は、真空蒸着法、ＣＶＤ
法、スピンコート法等の塗布法、及び累積膜法等の方法
により形成され、１ｎｍ〜１μｍの厚さに、単層、また
は多層構造として形成されることが好ましい。The electron injecting and transporting layer is formed by vacuum vapor deposition or CVD.
Method, a coating method such as a spin coating method, and a method such as a cumulative film method, and are preferably formed as a single layer or a multilayer structure with a thickness of 1 nm to 1 μm.
【００７６】以上、基板側から順に、陽極、正孔注入輸
送層、有機発光層、必要に応じて電子注入輸送層、及び
陰極を積層した構造について示したが、本発明の有機薄
膜ＥＬ素子は、基板側から順に、陰極、電子注入輸送
層、有機発光層、正孔注入輸送層、及び陽極を積層した
構造であってもよい。The structure in which the anode, the hole injecting and transporting layer, the organic light emitting layer, the electron injecting and transporting layer, and the cathode are laminated in this order from the substrate side has been described above. It may have a structure in which a cathode, an electron injecting and transporting layer, an organic light emitting layer, a hole injecting and transporting layer, and an anode are laminated in this order from the substrate side.
【００７７】本発明の有機薄膜ＥＬ素子は、有機層や電
極の酸化を防止するために、有機層及び電極上に、封止
層が形成されていてもよい。この封止層に用いられる材
料は、ガスバリア性及び水蒸気バリア性の高い材料であ
れば特に制限はないが、ＳｉＯ2 、ＳｉＯ、ＧｅＯ、Ｍ
ｇＯ、Ａｌ2 Ｏ3 、Ｂ2 Ｏ3 、ＴｉＯ2 、ＺｎＯ、及び
ＳｎＯ等の酸化物（これら酸化物の組成は、化学量論比
からずれていることもある）、ＭｇＦ2 、ＬｉＦ、Ｂａ
Ｆ2 、ＡｌＦ3 、及びＦｅＦ2 等のフッ化物、ＺｎＳ、
ＧｅＳ、及びＳｎＳ等の硫化物等の無機化合物を挙げる
ことができる。In the organic thin film EL element of the present invention, a sealing layer may be formed on the organic layer and the electrode in order to prevent oxidation of the organic layer and the electrode. The material used for this sealing layer is not particularly limited as long as it is a material having a high gas barrier property and a water vapor barrier property, but SiO 2 , SiO, GeO, M
Oxides such as gO, Al 2 O 3 , B 2 O 3 , TiO 2 , ZnO, and SnO (the composition of these oxides may deviate from the stoichiometric ratio), MgF 2 , LiF, Ba.
Fluorides such as F 2 , AlF 3 and FeF 2 , ZnS,
Inorganic compounds such as sulfides such as GeS and SnS can be mentioned.
【００７８】封止層は、これら材料を、蒸着法、反応性
蒸着法、ＣＶＤ法、スパッタリング法、及びイオンプレ
ーティング法等の方法により、単体または複合化して、
或いは、積層して成膜することにより、形成される。For the sealing layer, these materials are used alone or in combination by a method such as a vapor deposition method, a reactive vapor deposition method, a CVD method, a sputtering method and an ion plating method,
Alternatively, it is formed by stacking and forming a film.
【００７９】陰極の酸化防止のために、封止層中または
封止層表面に、Ｌｉ等のアルカリ金属、Ｃａ及びＭｇ等
のアルカリ土類金属、及びＥｕ等の希土類金属等の層を
設けることができる。また、上述の無機化合物とこれら
金属との混合層を設けてもよい。In order to prevent oxidation of the cathode, a layer of an alkali metal such as Li, an alkaline earth metal such as Ca and Mg, and a rare earth metal such as Eu is provided in or on the surface of the sealing layer. You can Further, a mixed layer of the above-mentioned inorganic compound and these metals may be provided.
【００８０】さらに、このＥＬ素子中への水蒸気の進入
を防止するために、ハーメチックシール等により素子を
真空中で密封するか、ガラス板等の封止板を素子の有機
発光層が形成された面に配置し、ガラス板と素子との間
隙を、市販の低吸湿性の光硬化性接着剤、エポキシ系接
着剤、シリコーン系接着剤、架橋エチレン−酢酸ビニル
共重合体接着剤シート等の接着性樹脂、及び低融点ガラ
ス等の接着材料で封止することが好ましい。Further, in order to prevent the entry of water vapor into the EL device, the device is hermetically sealed in vacuum or a sealing plate such as a glass plate is formed on the organic light emitting layer of the device. Placed on the surface, and the gap between the glass plate and the element is bonded to a commercially available low hygroscopic photo-curable adhesive, epoxy adhesive, silicone adhesive, cross-linked ethylene-vinyl acetate copolymer adhesive sheet, etc. It is preferable to seal with a transparent resin and an adhesive material such as low melting point glass.
【００８１】封止板としては、上述のガラス板の他に、
金属板及びプラスチック板等を用いることができる。ま
た、接着材料中に、シリカゲルやゼオライト等の乾燥剤
を混合することができ、封止層表面や、封止板の有機発
光層側の面に、シリカゲル、ゼオライト、及びカルシア
等の乾燥剤や、アルカリ金属、アルカリ土類金属、及び
希土類等からなるゲッター剤の層を形成してもよい。As the sealing plate, in addition to the above-mentioned glass plate,
A metal plate, a plastic plate, etc. can be used. In addition, a desiccant such as silica gel or zeolite can be mixed in the adhesive material, and a desiccant such as silica gel, zeolite, and calcia can be added to the sealing layer surface or the surface of the sealing plate on the organic light emitting layer side. You may form the layer of the getter agent which consists of an alkali metal, an alkaline earth metal, a rare earth, etc.
【００８２】以上のように構成される本発明の有機薄膜
ＥＬ素子は、正孔注入輸送層側を正極として直流電圧を
印加することにより発光するが、交流電圧を印加した場
合でも正孔注入輸送層側に正の電圧が印加されている間
は発光する。The organic thin-film EL device of the present invention configured as described above emits light when a DC voltage is applied with the hole injecting and transporting layer side serving as a positive electrode. It emits light while a positive voltage is applied to the layer side.
【００８３】また、本発明の有機薄膜ＥＬ素子を、基板
上に２次元的に配列することにより、文字や画像を表示
することが可能な薄型ディスプレイを形成することがで
きる。By arranging the organic thin film EL element of the present invention two-dimensionally on the substrate, a thin display capable of displaying characters and images can be formed.
【００８４】さらに、赤、青、緑の３色の発光素子を２
次元的に配列するか、或いは、白色発光素子とカラーフ
ィルタとを用いることにより、カラーディスプレイ化が
可能となる。また、上記一般式（１）に示す化合物を有
機発光層の有機蛍光体として用いた場合は、青から緑、
及び青から赤に変換する、蛍光変換フィルタを配列する
ことにより、カラーディスプレイ化が可能となる。Furthermore, two light emitting elements of three colors of red, blue and green are provided.
A color display can be realized by arranging in a dimension or using a white light emitting element and a color filter. Further, when the compound represented by the general formula (1) is used as the organic phosphor of the organic light emitting layer, blue to green,
By arranging a fluorescence conversion filter for converting from blue to red, a color display can be realized.
【００８５】[0085]
【実施例】以下、本発明の実施例について説明する。
（実施例１）上記化学式（７）に示す化合物を、以下の
ようにして合成した。EXAMPLES Examples of the present invention will be described below. (Example 1) The compound represented by the chemical formula (7) was synthesized as follows.
【００８６】まず、０．０４モルの９−リチオ−アント
ラセンを、２：１の体積比で混合したジエチルエーテル
／トルエン混合液３００ｍｌ中に溶解した。この溶液
に、０．０２モルのジクロロジフェニルシランを滴下
し、５０℃で１４時間反応させた。この反応液を、カラ
ムクロマトグラフィーで精製し、上記化学式（７）に示
す化合物を得た。First, 0.04 mol of 9-lithio-anthracene was dissolved in 300 ml of a diethyl ether / toluene mixed liquid mixed in a volume ratio of 2: 1. To this solution, 0.02 mol of dichlorodiphenylsilane was added dropwise and reacted at 50 ° C. for 14 hours. This reaction solution was purified by column chromatography to obtain the compound represented by the above chemical formula (7).
【００８７】この化合物について、マススペクトル測定
を行ったところ、分子量が５３６の分子イオンピークが
確認された。また、この化合物について、ＣＤＣｌ3 を
溶媒としてプロトンＮＭＲ測定を行った。以下に、その
結果を示す。Mass spectrum measurement of this compound confirmed a molecular ion peak with a molecular weight of 536. Further, this compound was subjected to proton NMR measurement using CDCl 3 as a solvent. The results are shown below.
【００８８】
6.80-6.83(4H,t,CH) 7.11-7.15(4H,t,CH)
7.21-7.25(6H,t,CH) 7.57-7.59(4H,w,CH)
7.94-7.96(4H,w,CH) 8.20-8.23(4H,w,CH)
8.56(2H,s,CH)
さらに、この化合物の蛍光ピーク波長を調べたところ、
４７２ｎｍであることが分かり、理研計器（株）製の表
面分析装置ＡＣ−１による測定の結果、イオン化エネル
ギーは６．０ｅＶであり、また、吸収端波長から求めた
エネルギーギャップは、２．９２ｅＶであった。6.80-6.83 (4H, t, CH) 7.11-7.15 (4H, t, CH) 7.21-7.25 (6H, t, CH) 7.57-7.59 (4H, w, CH) 7.94-7.96 (4H, w , CH) 8.20-8.23 (4H, w, CH) 8.56 (2H, s, CH) Furthermore, when the fluorescence peak wavelength of this compound was examined,
It was found to be 472 nm, and as a result of measurement by a surface analyzer AC-1 manufactured by Riken Keiki Co., Ltd., the ionization energy was 6.0 eV, and the energy gap obtained from the absorption edge wavelength was 2.92 eV. there were.
【００８９】以上のようにして合成した上記化学式
（７）に示す化合物を有機発光層に用いて、以下に示す
ようにして有機薄膜ＥＬ素子を作製した。まず、透明絶
縁性の基板として厚さ１．１ｍｍの青色ガラス板を用
い、このガラス板上に、スパッタリング法により厚さ１
２０ｎｍのＩＴＯ膜を陽極として形成した。このＩＴＯ
膜が形成されたガラス板に、水洗及びプラズマ洗浄を施
した後、真空蒸着法により、ＩＴＯ膜上に、アルドリッ
チ製のＣｕＰｃからなる厚さ１０ｎｍの第１正孔注入輸
送層を成膜した。Using the compound represented by the above chemical formula (7) synthesized as described above for the organic light emitting layer, an organic thin film EL device was prepared as follows. First, a 1.1 mm-thick blue glass plate was used as a transparent insulating substrate, and a glass plate having a thickness of 1 was formed on the glass plate by a sputtering method.
A 20 nm ITO film was formed as an anode. This ITO
The glass plate on which the film was formed was washed with water and plasma, and then a 10-nm-thick first hole injecting and transporting layer made of CuPc made of Aldrich was formed on the ITO film by a vacuum evaporation method.
【００９０】次に、この第１正孔注入輸送層上に、Ｎ，
Ｎ，Ｎ’，Ｎ’−テトラ−ｍ−トリル−１，１’−ビフ
ェニル−４，４’−ジアミンを用いて、真空蒸着法によ
り厚さ３５ｎｍで第２正孔注入輸送層を成膜し、この第
２正孔注入輸送層上に、上記化学式（１）に示す化合物
を用いて、真空蒸着法により厚さ１０ｎｍで第３正孔注
入輸送層を成膜した。Next, on the first hole injecting and transporting layer, N,
Using N, N ', N'-tetra-m-tolyl-1,1'-biphenyl-4,4'-diamine, a second hole injecting and transporting layer having a thickness of 35 nm was formed by vacuum deposition. A 10-nm-thick third hole injecting and transporting layer was formed on the second hole injecting and transporting layer using the compound represented by the chemical formula (1) by a vacuum vapor deposition method.
【００９１】この第３正孔注入輸送層上に、蒸着法によ
り、上記化学式（７）に示す化合物からなる膜を５０ｎ
ｍの厚さで成膜して有機発光層を形成した。この有機発
光層上に、ＡｌとＬｉとを蒸着速度比５：１で６０ｎｍ
の厚さで蒸着し、さらにＡｌを２００ｎｍの厚さで蒸着
して、陰極を形成した。On this third hole injecting and transporting layer, a film made of the compound represented by the above chemical formula (7) is formed in a thickness of 50 n by vapor deposition.
A film having a thickness of m was formed to form an organic light emitting layer. Al and Li are deposited on the organic light emitting layer at a deposition rate ratio of 5: 1 of 60 nm.
Was evaporated to a thickness of 200 nm, and Al was evaporated to a thickness of 200 nm to form a cathode.
【００９２】さらに、陰極上に、封止層としてＧｅＯを
１．４μｍの厚さで蒸着し、この封止層上にガラス板を
配置して、封止層とガラス板との間隙を光硬化性樹脂で
充填・接着することにより、有機薄膜ＥＬ素子を作製し
た。Further, GeO was vapor-deposited as a sealing layer to a thickness of 1.4 μm on the cathode, a glass plate was placed on the sealing layer, and the gap between the sealing layer and the glass plate was photocured. An organic thin film EL element was produced by filling and adhering with an organic resin.
【００９３】以上のようにして作製した有機薄膜ＥＬ素
子について、直流電圧を印加して発光させたところ、４
Ｖの直流電圧印加時には青色の安定発光が得られ、１４
Ｖの直流電圧印加時には、１７８８ｃｄ／ｍ2 の輝度が
得られ、この時の電流密度は３５９ｍＡ／ｃｍ2 であっ
た。When the organic thin film EL element manufactured as described above was made to emit light by applying a DC voltage, 4
When a DC voltage of V is applied, stable blue light emission is obtained.
When a DC voltage of V was applied, a luminance of 1788 cd / m 2 was obtained, and the current density at this time was 359 mA / cm 2 .
【００９４】この素子の作製時に、素子に熱が印加され
たが、作製された素子に電気的短絡等の不具合は生じな
かった。また、この素子についても、２５℃の温度条件
下で、２０ｍＡ／ｃｍ2 の直流電流を１００時間連続的
に印加して、素子特性の変化を調べたが、電気的短絡に
基づく特性の劣化は生じなかった。Heat was applied to the device during the manufacture of this device, but no defects such as electrical short circuit occurred in the manufactured device. Also, with respect to this element as well, a direct current of 20 mA / cm 2 was continuously applied for 100 hours under a temperature condition of 25 ° C., and changes in element characteristics were examined. Did not happen.
【００９５】（実施例２）上記化学式（７）に示す化合
物を電子注入輸送層に用いて、以下に示すようにして有
機薄膜ＥＬ素子を作製した。Example 2 An organic thin film EL device was manufactured as follows by using the compound represented by the above chemical formula (7) in the electron injecting and transporting layer.
【００９６】まず、透明絶縁性の基板として厚さ１．１
ｍｍの青色ガラス板を用い、このガラス板上に、スパッ
タリング法により厚さ１２０ｎｍのＩＴＯ膜を陽極とし
て形成した。このＩＴＯ膜が形成されたガラス板に、水
洗及びプラズマ洗浄を施した後、真空蒸着法により、Ｉ
ＴＯ膜上に、アルドリッチ製のＣｕＰｃからなる厚さ１
０ｎｍの第１正孔注入輸送層を成膜した。First, a transparent insulating substrate having a thickness of 1.1 is used.
An ITO film having a thickness of 120 nm was formed as an anode on this glass plate by a sputtering method using a blue glass plate having a size of mm. The glass plate on which the ITO film was formed was washed with water and plasma, and then I
Thickness of CuPc made by Aldrich on the TO film 1
A 0 nm first hole injecting and transporting layer was formed.
【００９７】次に、この第１正孔注入輸送層上に、Ｎ，
Ｎ，Ｎ’，Ｎ’−テトラ−ｍ−トリル−１，１’−ビフ
ェニル−４，４’−ジアミンを用いて、真空蒸着法によ
り厚さ３５ｎｍで第２正孔注入輸送層を成膜し、この第
２正孔注入輸送層上に、上記化学式（１）に示す化合物
を用いて、真空蒸着法により厚さ１０ｎｍで第３正孔注
入輸送層を成膜した。この第３正孔注入輸送層上に、蒸
着法により、下記化学式（１８）に示す化合物からなる
膜を４０ｎｍの厚さで成膜して有機発光層を形成した。Next, on the first hole injecting and transporting layer, N,
Using N, N ', N'-tetra-m-tolyl-1,1'-biphenyl-4,4'-diamine, a second hole injecting and transporting layer having a thickness of 35 nm was formed by vacuum deposition. A 10-nm-thick third hole injecting and transporting layer was formed on the second hole injecting and transporting layer using the compound represented by the chemical formula (1) by a vacuum vapor deposition method. On this third hole injecting and transporting layer, a film made of a compound represented by the following chemical formula (18) was formed to a thickness of 40 nm by an evaporation method to form an organic light emitting layer.
【００９８】[0098]
【化９】 [Chemical 9]
【００９９】この有機発光層上に、上記化学式（７）に
示す化合物を１０ｎｍの厚さで蒸着して電子注入輸送層
を形成した。この電子注入輸送層上に、ＡｌとＬｉとを
蒸着速度比５：１で６０ｎｍの厚さで蒸着し、さらにＡ
ｌを２００ｎｍの厚さで蒸着して、陰極を形成した。On the organic light emitting layer, the compound represented by the above chemical formula (7) was vapor-deposited to a thickness of 10 nm to form an electron injecting and transporting layer. On this electron injecting and transporting layer, Al and Li were vapor-deposited with a vapor deposition rate ratio of 5: 1 to a thickness of 60 nm, and further A
l was evaporated to a thickness of 200 nm to form a cathode.
【０１００】さらに、陰極上に、封止層としてＧｅＯを
１．４μｍの厚さで蒸着し、この封止層上にガラス板を
配置して、封止層とガラス板との間隙を光硬化性樹脂で
充填・接着することにより、有機薄膜ＥＬ素子を作製し
た。Further, GeO was vapor-deposited as a sealing layer to a thickness of 1.4 μm on the cathode, a glass plate was placed on the sealing layer, and the gap between the sealing layer and the glass plate was photocured. An organic thin film EL element was produced by filling and adhering with an organic resin.
【０１０１】以上のようにして作製した有機薄膜ＥＬ素
子について、直流電圧を印加して発光させたところ、４
Ｖの直流電圧印加時には青色の安定発光が得られ、１４
Ｖの直流電圧印加時には、１１４０ｃｄ／ｍ2 の輝度が
得られ、この時の電流密度は５８５ｍＡ／ｃｍ2 であっ
た。When the organic thin film EL element manufactured as described above was made to emit light by applying a DC voltage, it was found to be 4
When a DC voltage of V is applied, stable blue light emission is obtained.
When a DC voltage of V was applied, a brightness of 1140 cd / m 2 was obtained, and the current density at this time was 585 mA / cm 2 .
【０１０２】この素子の作製時に、素子に熱が印加され
たが、作製された素子に電気的短絡等の不具合は生じな
かった。また、この素子についても、２５℃の温度条件
下で、２０ｍＡ／ｃｍ2 の直流電流を１００時間連続的
に印加して、素子特性の変化を調べたが、電気的短絡に
基づく特性の劣化は生じなかった。Heat was applied to the device during the manufacture of this device, but no defects such as electrical short circuit occurred in the manufactured device. Also, with respect to this element as well, a direct current of 20 mA / cm 2 was continuously applied for 100 hours under a temperature condition of 25 ° C., and changes in element characteristics were examined. Did not happen.
【０１０３】（実施例３）上記化学式（７）に示す化合
物の代わりに、上記化学式（８）〜（１６）に示す化合
物を有機発光層の材料として用いたこと以外は実施例１
と同様にして、それぞれ有機薄膜ＥＬ素子を作製した。Example 3 Example 1 was repeated except that the compounds represented by the chemical formulas (8) to (16) were used as the material for the organic light emitting layer instead of the compound represented by the chemical formula (7).
Organic thin film EL devices were prepared in the same manner as in.
【０１０４】それぞれの有機薄膜ＥＬ素子について、１
４Ｖの直流電圧印加したところ、全ての素子で、１００
０ｃｄ／ｍ2 以上の輝度の安定した青色発光が得られ
た。これら素子の作製時に、素子に熱が印加されたが、
作製された素子に電気的短絡等の不具合は生じなかっ
た。また、これら素子についても、２５℃の温度条件下
で、２０ｍＡ／ｃｍ2 の直流電流を１００時間連続的に
印加して、素子特性の変化を調べたが、電気的短絡に基
づく特性の劣化は生じなかった。For each organic thin film EL element, 1
When a DC voltage of 4 V was applied, 100
Stable blue light emission with a brightness of 0 cd / m 2 or more was obtained. Heat was applied to the devices during the fabrication of these devices,
No defects such as an electrical short circuit occurred in the manufactured element. Also, regarding these elements, a direct current of 20 mA / cm 2 was continuously applied for 100 hours under a temperature condition of 25 ° C., and changes in element characteristics were examined. Did not happen.
【０１０５】（比較例）有機発光層を構成する材料とし
て、１，１，４，４，−テトラフェニル−１，３−ブタ
ジエンを用いたこと以外は実施例１と同様にして有機薄
膜ＥＬ素子を作製した。(Comparative Example) An organic thin film EL device was prepared in the same manner as in Example 1 except that 1,1,4,4-tetraphenyl-1,3-butadiene was used as the material for the organic light emitting layer. Was produced.
【０１０６】しかしながら、この素子の作製時印加され
た熱により、作製された素子に電気的短絡等の不具合が
生じた。この有機薄膜ＥＬ素子についても、１４Ｖの直
流電圧印加したところ、１００ｃｄ／ｍ2 程度の非常に
低い輝度の青色発光が得られた。However, the heat applied during the production of this element caused a defect such as an electrical short circuit in the produced element. When a DC voltage of 14 V was applied to this organic thin film EL element, blue light emission of very low brightness of about 100 cd / m 2 was obtained.
【０１０７】また、この素子について、２５℃の温度条
件下で、２０ｍＡ／ｃｍ2 の直流電流を１００時間連続
的に印加して、素子特性の変化を調べた。その結果、電
気的短絡がさらに増加し、発光輝度の大幅な低下が確認
された。With respect to this device, a change in device characteristics was examined by continuously applying a direct current of 20 mA / cm 2 for 100 hours under a temperature condition of 25 ° C. As a result, it was confirmed that the number of electrical shorts further increased and the emission luminance was significantly reduced.
【０１０８】[0108]
【発明の効果】以上示したように、本発明によると、融
点及びＴg が高く、透明で平滑なアモルファス膜の形成
が容易な上記一般式（１）に示す化合物が、有機発光層
或いは電子注入輸送層中に含有されるため、有機層の溶
融・結晶化が防止され、耐熱性が高く、電気的短絡の生
じにくい有機薄膜ＥＬ素子が提供される。As described above, according to the present invention, the compound represented by the general formula (1), which has a high melting point and T g and is easy to form a transparent and smooth amorphous film, can be used as an organic light emitting layer or an electron emitting layer. Since it is contained in the injecting and transporting layer, the organic layer is prevented from being melted and crystallized, the heat resistance is high, and the organic thin film EL element in which electrical short circuit is unlikely to occur is provided.
【図１】本発明の一実施形態に係る有機薄膜ＥＬ素子の
一断面図。FIG. 1 is a cross-sectional view of an organic thin film EL element according to an embodiment of the present invention.
【図２】本発明の他の実施形態に係る有機薄膜ＥＬ素子
の一断面図。FIG. 2 is a cross-sectional view of an organic thin film EL element according to another embodiment of the present invention.
【図３】本発明のさらに他の実施形態に係る有機薄膜Ｅ
Ｌ素子の一断面図。FIG. 3 is an organic thin film E according to another embodiment of the present invention.
FIG. 3 is a cross-sectional view of an L element.
１…基板 ２、５…電極 ３…正孔注入輸送層 ４…有機発光層 ６…電源 ７、９…配線 ８…導電部 １０…封止層 １１…接着性材料 １２…封止板 １３…第１の正孔注入輸送層 １４…第２の正孔注入輸送層 １５…第３の正孔注入輸送層 １６…電子注入輸送層 1 ... Substrate 2, 5 ... Electrodes 3 ... Hole injecting and transporting layer 4 ... Organic light emitting layer 6 ... Power supply 7, 9 ... Wiring 8 ... Conductive part 10 ... Sealing layer 11 ... Adhesive material 12 ... Sealing plate 13 ... First hole injecting and transporting layer 14 ... Second hole injecting and transporting layer 15 ... Third hole injecting and transporting layer 16 ... Electron injection transport layer
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) H05B 33/14 H05B 33/22 C09K 11/06 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)─────────────────────────────────────────────────── ─── Continuation of the front page (58) Fields surveyed (Int.Cl. 7 , DB name) H05B 33/14 H05B 33/22 C09K 11/06 CA (STN) REGISTRY (STN)
Claims (4)
般式（１）に示す化合物を含有することを特徴とする有
機薄膜ＥＬ素子。 【化１】 （式中、Ｒは、アルキル基またはアリール基を示し、Ａ
ｒは、縮合芳香族環を含み且つ前記一般式（１）中のＳ
ｉに前記縮合芳香族環が直接結合する置換基または縮合
芳香族環とベンゼン環とを含み且つ前記一般式（１）中
のＳｉに前記縮合芳香族環が前記ベンゼン環のみを介し
て結合する置換基を示す。）1. A substrate, a pair of electrodes arranged on the substrate and facing each other, and an organic light-emitting layer provided between the pair of electrodes, and any one of layers formed between the pair of electrodes. An organic thin film EL device, wherein the layer contains a compound represented by the following general formula (1). [Chemical 1] (In the formula, R represents an alkyl group or an aryl group, and
r is, S condensed aromatic ring only contains and the general formula (1)
Substituent or fused in which the fused aromatic ring is directly bonded to i
In the general formula (1), which contains an aromatic ring and a benzene ring
The condensed aromatic ring is attached to Si of only the benzene ring.
Represents a substituent bonded to each other . )
間に設けられた正孔注入輸送層を具備し、前記有機発光
層が前記一般式（１）に示す化合物を含有することを特
徴とする請求項１に記載の有機薄膜ＥＬ素子。2. A hole injecting and transporting layer provided between one of the pair of electrodes and the organic light emitting layer, wherein the organic light emitting layer contains the compound represented by the general formula (1). The organic thin film EL element according to claim 1, which is characterized in that.
間に設けられた電子注入輸送層を具備することを特徴と
する請求項２に記載の有機薄膜ＥＬ素子。3. The organic thin film EL element according to claim 2, further comprising an electron injecting and transporting layer provided between the other of the pair of electrodes and the organic light emitting layer.
間に設けられた正孔注入輸送層と、前記電極対の他方と
前記有機発光層との間に設けられた電子注入輸送層とを
具備し、前記電子注入輸送層が前記一般式（１）に示す
化合物を含有することを特徴とする請求項１に記載の有
機薄膜ＥＬ素子。4. A hole injecting and transporting layer provided between one of the electrode pairs and the organic light emitting layer, and an electron injecting and transporting layer provided between the other of the electrode pair and the organic light emitting layer. 2. The organic thin film EL device according to claim 1, wherein the electron injecting and transporting layer contains the compound represented by the general formula (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15521097A JP3518255B2 (en) | 1997-06-12 | 1997-06-12 | Organic thin film EL device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15521097A JP3518255B2 (en) | 1997-06-12 | 1997-06-12 | Organic thin film EL device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH113781A JPH113781A (en) | 1999-01-06 |
| JP3518255B2 true JP3518255B2 (en) | 2004-04-12 |
Family
ID=15600923
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15521097A Expired - Fee Related JP3518255B2 (en) | 1997-06-12 | 1997-06-12 | Organic thin film EL device |
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| Country | Link |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3865996B2 (en) | 1999-04-07 | 2007-01-10 | 富士フイルムホールディングス株式会社 | A specific silane compound, a light emitting device material comprising the same, and a light emitting device containing the same. |
| JP2000290284A (en) | 1999-04-07 | 2000-10-17 | Fuji Photo Film Co Ltd | Specific silane compound, its synthesis, and luminous element material comprising the compound and luminous element containing the same |
| JP4512217B2 (en) | 1999-08-20 | 2010-07-28 | 富士フイルム株式会社 | Arylsilane compound, light emitting device material, and light emitting device using the same |
| JP4849812B2 (en) * | 2004-03-26 | 2012-01-11 | 富士フイルム株式会社 | Organic electroluminescent device and silicon compound |
| KR101193179B1 (en) * | 2005-08-26 | 2012-10-19 | 삼성디스플레이 주식회사 | Organosiloxane compound and organic electroluminescence device comprsing the same |
| KR101193180B1 (en) | 2005-11-14 | 2012-10-19 | 삼성디스플레이 주식회사 | A conducting polymer composition and an electronic device employing the layer obtained from the conducting polymer composition |
| KR101243917B1 (en) | 2005-12-19 | 2013-03-14 | 삼성디스플레이 주식회사 | A conducting polymer composition and an electrical device employing the layer obtained from the conducting polymer composition |
| JP4722746B2 (en) * | 2006-03-29 | 2011-07-13 | 京セラ株式会社 | EL device |
| JP2009152113A (en) * | 2007-12-21 | 2009-07-09 | Rohm Co Ltd | Organic el element |
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