JP2001244075A - Hydrocarbon compound and organic electroluminescent element - Google Patents
Hydrocarbon compound and organic electroluminescent elementInfo
- Publication number
- JP2001244075A JP2001244075A JP2000054073A JP2000054073A JP2001244075A JP 2001244075 A JP2001244075 A JP 2001244075A JP 2000054073 A JP2000054073 A JP 2000054073A JP 2000054073 A JP2000054073 A JP 2000054073A JP 2001244075 A JP2001244075 A JP 2001244075A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- organic electroluminescent
- electroluminescent device
- 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.)
- Granted
Links
- 150000002430 hydrocarbons Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 202
- 125000005843 halogen group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
- 238000002347 injection Methods 0.000 claims description 65
- 239000007924 injection Substances 0.000 claims description 65
- 150000002790 naphthalenes Chemical class 0.000 claims description 15
- 125000002524 organometallic group Chemical group 0.000 claims description 10
- 125000005259 triarylamine group Chemical group 0.000 claims description 7
- 239000010410 layer Substances 0.000 description 151
- -1 1- Methylpentyl group Chemical group 0.000 description 132
- 238000007740 vapor deposition Methods 0.000 description 55
- 239000000758 substrate Substances 0.000 description 49
- 238000000151 deposition Methods 0.000 description 41
- 230000008021 deposition Effects 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 26
- 229940126062 Compound A Drugs 0.000 description 25
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 18
- 239000011521 glass Substances 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 15
- 239000011777 magnesium Substances 0.000 description 15
- 229910052749 magnesium Inorganic materials 0.000 description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 14
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 description 14
- 229910052709 silver Inorganic materials 0.000 description 14
- 239000004332 silver Substances 0.000 description 14
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 13
- 239000003599 detergent Substances 0.000 description 13
- 229910001873 dinitrogen Inorganic materials 0.000 description 13
- 230000007935 neutral effect Effects 0.000 description 13
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 239000002356 single layer Substances 0.000 description 9
- 238000010586 diagram Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000004506 ultrasonic cleaning Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000007772 electrode material Substances 0.000 description 5
- CIFSLCJJYQZADO-UHFFFAOYSA-N fluoranthen-3-yloxyboronic acid Chemical class C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3OB(O)O CIFSLCJJYQZADO-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920000123 polythiophene Polymers 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000003618 dip coating Methods 0.000 description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 4
- 239000012453 solvate Substances 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
- 238000001771 vacuum deposition Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ISZWRZGKEWQACU-UHFFFAOYSA-N Primuletin Natural products OC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1 ISZWRZGKEWQACU-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 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 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- IYBLVRRCNVHZQJ-UHFFFAOYSA-N 5-Hydroxyflavone Chemical compound C=1C(=O)C=2C(O)=CC=CC=2OC=1C1=CC=CC=C1 IYBLVRRCNVHZQJ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910000846 In alloy Inorganic materials 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-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
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004962 Polyamide-imide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- PPYIVKOTTQCYIV-UHFFFAOYSA-L beryllium;selenate Chemical compound [Be+2].[O-][Se]([O-])(=O)=O PPYIVKOTTQCYIV-UHFFFAOYSA-L 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 238000004440 column chromatography Methods 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
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000004880 oxines Chemical class 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 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
- 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 2
- 239000002985 plastic film Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000548 poly(silane) polymer Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002312 polyamide-imide Polymers 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920006380 polyphenylene oxide Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000000746 purification Methods 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
- 229920002050 silicone resin Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- GDTMIGSCWLYRHS-UHFFFAOYSA-K (2,6-diphenylphenoxy)-bis[(2-methylquinolin-8-yl)oxy]alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.[O-]C1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 GDTMIGSCWLYRHS-UHFFFAOYSA-K 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- HMWIELQAYYDAGJ-UHFFFAOYSA-N 1,2,3,4,5-pentakis-phenylcyclohexa-1,3-diene Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HMWIELQAYYDAGJ-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- ZKSVYBRJSMBDMV-UHFFFAOYSA-N 1,3-diphenyl-2-benzofuran Chemical compound C1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C=CC=CC=2)O1 ZKSVYBRJSMBDMV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- 229920001296 polysiloxane Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical class [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- XRXDCKUSXVGNCW-UHFFFAOYSA-K tris[(2-methylquinolin-8-yl)oxy]alumane Chemical compound C1=C(C)N=C2C(O[Al](OC=3C4=NC(C)=CC=C4C=CC=3)OC3=CC=CC4=CC=C(N=C43)C)=CC=CC2=C1 XRXDCKUSXVGNCW-UHFFFAOYSA-K 0.000 description 1
- SXXNJJQVBPWGTP-UHFFFAOYSA-K tris[(4-methylquinolin-8-yl)oxy]alumane Chemical compound [Al+3].C1=CC=C2C(C)=CC=NC2=C1[O-].C1=CC=C2C(C)=CC=NC2=C1[O-].C1=CC=C2C(C)=CC=NC2=C1[O-] SXXNJJQVBPWGTP-UHFFFAOYSA-K 0.000 description 1
- HSRBHVUVCOUJAC-UHFFFAOYSA-K tris[(5-methylquinolin-8-yl)oxy]alumane Chemical compound [Al+3].C1=CC=C2C(C)=CC=C([O-])C2=N1.C1=CC=C2C(C)=CC=C([O-])C2=N1.C1=CC=C2C(C)=CC=C([O-])C2=N1 HSRBHVUVCOUJAC-UHFFFAOYSA-K 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、有機電界発光素子
および該発光素子に好適に使用できる新規な炭化水素化
合物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device and a novel hydrocarbon compound which can be suitably used for the device.
【0002】[0002]
【従来の技術】従来、無機電界発光素子は、例えば、バ
ックライトなどのパネル型光源として使用されてきた
が、該発光素子を駆動させるには、交流の高電圧が必要
である。最近になり、発光材料に有機材料を用いた有機
電界発光素子(有機エレクトロルミネッセンス素子:有
機EL素子)が開発された[Appl.Phys.Lett.,51,913(19
87)]。有機電界発光素子は、蛍光性有機化合物を含む薄
膜を、陽極と陰極間に挟持された構造を有し、該薄膜に
電子および正孔(ホール)を注入して、再結合させるこ
とにより励起子(エキシトン)を生成させ、この励起子
が失活する際に放出される光を利用して発光する素子で
ある。有機電界発光素子は、数V〜数十V程度の直流の
低電圧で、発光が可能であり、また蛍光性有機化合物の
種類を選択することにより種々の色(例えば、赤色、青
色、緑色)の発光が可能である。このような特徴を有す
る有機電界発光素子は、種々の発光素子、表示素子等へ
の応用が期待されている。しかしながら、一般に、発光
輝度が低く、実用上十分ではない。2. Description of the Related Art Conventionally, an inorganic electroluminescent device has been used as a panel-type light source such as a backlight. However, driving the light emitting device requires a high AC voltage. Recently, an organic electroluminescence device using an organic material as an emission material (organic electroluminescence device: organic EL device) has been developed [Appl. Phys. Lett., 51 , 913 (19)
87)]. An organic electroluminescent element has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode, and electrons and holes are injected into the thin film and recombined to form excitons. (Exciton), and emits light using light emitted when the exciton is deactivated. The organic electroluminescent element can emit light at a low DC voltage of about several volts to several tens of volts, and can have various colors (for example, red, blue, and green) by selecting the type of the fluorescent organic compound. Light emission is possible. Organic electroluminescent devices having such characteristics are expected to be applied to various light emitting devices, display devices, and the like. However, in general, the emission luminance is low and is not practically sufficient.
【0003】発光輝度を向上させる方法として、発光層
として、例えば、トリス(8−キノリノラート)アルミ
ニウムをホスト化合物、クマリン誘導体、ピラン誘導体
をゲスト化合物(ドーパント)として用いた有機電界発
光素子が提案されている[J.Appl.Phys.,65,3610(198
9)]。また、発光層として、例えば、ビス(2−メチル
−8−キノリノラート)(4−フェニルフェノラート)
アルミニウムをホスト化合物、アクリドン誘導体(例え
ば、N−メチル−2−メトキシアクリドン)をゲスト化
合物として用いた有機電界発光素子が提案されている
(特開平8−67873号公報)。しかしながら、これ
らの発光素子も充分な発光輝度を有しているとは言い難
い。現在では、一層高輝度に発光する有機電界発光素子
が望まれている。As a method for improving light emission luminance, an organic electroluminescent device using, for example, tris (8-quinolinolato) aluminum as a host compound, a coumarin derivative, or a pyran derivative as a guest compound (dopant) has been proposed as a light emitting layer. J. Appl. Phys., 65 , 3610 (198
9)]. Further, as the light emitting layer, for example, bis (2-methyl-8-quinolinolate) (4-phenylphenolate)
An organic electroluminescent device using aluminum as a host compound and an acridone derivative (for example, N-methyl-2-methoxyacridone) as a guest compound has been proposed (JP-A-8-67873). However, it is difficult to say that these light-emitting elements also have sufficient light emission luminance. At present, an organic electroluminescent device that emits light with higher luminance is desired.
【0004】[0004]
【発明が解決しようとする課題】本発明の課題は、発光
効率に優れ、高輝度に発光する有機電界発光素子を提供
することである。さらには、該発光素子に好適に使用で
きる新規な炭化水素化合物を提供することである。SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent device which is excellent in luminous efficiency and emits light with high luminance. Another object is to provide a novel hydrocarbon compound that can be suitably used for the light-emitting element.
【0005】[0005]
【課題を解決するための手段】本発明者等は、有機電界
発光素子に関して鋭意検討した結果、本発明を完成する
に到った。すなわち本発明は、 一対の電極間に、1,4−ジ(3’−フルオランテニ
ル)ナフタレン誘導体を少なくとも一種含有する層を、
少なくとも一層挟持してなる有機電界発光素子、 1,4−ジ(3’−フルオランテニル)ナフタレン誘
導体を含有する層が、発光層である前記記載の有機電
界発光素子、 1,4−ジ(3’−フルオランテニル)ナフタレン誘
導体を含有する層が、さらに、発光性有機金属錯体を含
有することを特徴とする前記または記載の有機電界
発光素子、 1,4−ジ(3’−フルオランテニル)ナフタレン誘
導体を含有する層が、さらに、トリアリールアミン誘導
体を含有することを特徴とする前記または記載の有
機電界発光素子、 一対の電極間に、さらに、正孔注入輸送層を有する前
記〜のいずれかに記載の有機電界発光素子、 一対の電極間に、さらに、電子注入輸送層を有する前
記〜のいずれかに記載の有機電界発光素子、 1,4−ジ(3’−フルオランテニル)ナフタレン誘
導体が、一般式(1−A)(化3)で表される化合物で
ある前記〜のいずれかに記載の有機電界発光素子、
に関するものである。Means for Solving the Problems The present inventors have made intensive studies on the organic electroluminescent device, and as a result, have completed the present invention. That is, the present invention provides a layer containing at least one 1,4-di (3′-fluoranthenyl) naphthalene derivative between a pair of electrodes,
The organic electroluminescent device according to the above, wherein the layer containing the 1,4-di (3′-fluoranthenyl) naphthalene derivative is a light-emitting layer, wherein the organic electroluminescent device has at least one layer sandwiched therebetween. The organic electroluminescent device according to the above or the above, wherein the layer containing a 3′-fluoranthenyl) naphthalene derivative further contains a light-emitting organometallic complex. 1,4-di (3′-fluorane) The organic electroluminescent device according to the above or the above, wherein the layer containing the (tenyl) naphthalene derivative further contains a triarylamine derivative. The organic electroluminescent device according to any one of the above, the organic electroluminescent device according to any one of the above, further comprising an electron injecting and transporting layer between a pair of electrodes, 1,4-di (3′-fluora The organic electroluminescent device according to any one of the above, wherein the (nenyl) naphthalene derivative is a compound represented by the general formula (1-A) (Formula 3),
It is about.
【0006】[0006]
【化3】 Embedded image
【0007】(式中、X1〜X24はそれぞれ独立に、水
素原子、ハロゲン原子、直鎖、分岐または環状のアルキ
ル基、直鎖、分岐または環状のアルコキシ基、あるい
は、置換または未置換のアリール基を表す。) さらに、本発明は、一般式(1−A)(化4)で表さ
れる化合物、に関するものである。(Wherein X 1 to X 24 each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted Further, the present invention relates to a compound represented by the general formula (1-A) (Formula 4).
【0008】[0008]
【化4】 Embedded image
【0009】(式中、X1〜X24はそれぞれ独立に、水
素原子、ハロゲン原子、直鎖、分岐または環状のアルキ
ル基、直鎖、分岐または環状のアルコキシ基、あるい
は、置換または未置換のアリール基を表す。)(Wherein X 1 to X 24 each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted Represents an aryl group.)
【0010】[0010]
【発明の実施の形態】以下、本発明に関して、詳細に説
明する。本発明の有機電界発光素子は、一対の電極間
に、1,4−ジ(3’−フルオランテニル)ナフタレン
誘導体を少なくとも一種含有する層を少なくとも一層挟
持してなるものである。本発明に係る1,4−ジ(3’
−フルオランテニル)ナフタレン誘導体(以下、本発明
に係る化合物Aと略記する)とは、一般式(1)(化
5)で表される骨格を有する化合物を表すものである。
一般式(1)で表される骨格は、種々の置換基で置換さ
れていてもよく、本発明に係る化合物Aは、好ましく
は、一般式(1−A)(化5)で表される化合物であ
る。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The organic electroluminescent device of the present invention is obtained by sandwiching at least one layer containing at least one 1,4-di (3′-fluoranthenyl) naphthalene derivative between a pair of electrodes. The 1,4-di (3 ′) according to the present invention
The (-fluoranthenyl) naphthalene derivative (hereinafter abbreviated as compound A according to the present invention) is a compound having a skeleton represented by the general formula (1) (formula 5).
The skeleton represented by the general formula (1) may be substituted with various substituents, and the compound A according to the present invention is preferably represented by the general formula (1-A) Compound.
【0011】[0011]
【化5】 Embedded image
【0012】(式中、X1〜X24はそれぞれ独立に、水
素原子、ハロゲン原子、直鎖、分岐または環状のアルキ
ル基、直鎖、分岐または環状のアルコキシ基、あるいは
置換または未置換のアリール基を表す。)(Wherein X 1 to X 24 each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group) Represents a group.)
【0013】一般式(1−A)で表される化合物におい
て、X1〜X24はそれぞれ独立に、水素原子、ハロゲン
原子、直鎖、分岐または環状のアルキル基、直鎖、分岐
または環状のアルコキシ基、あるいは、置換または未置
換のアリール基を表す。尚、本発明において、アリール
基とは、例えば、フェニル基、ナフチル基などの炭素環
式芳香族基、例えば、フリル基、チエニル基、ピリジル
基などの複素環式芳香族基を表す。一般式(1−A)で
表される化合物において、好ましくは、X1〜X24は水
素原子、ハロゲン原子、炭素数1〜20の直鎖、分岐ま
たは環状のアルキル基、炭素数1〜20の直鎖、分岐ま
たは環状のアルコキシ基、あるいは炭素数4〜20の置
換または未置換のアリール基を表す。In the compound represented by the general formula (1-A), X 1 to X 24 each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkyl group. Represents an alkoxy group or a substituted or unsubstituted aryl group. In the present invention, the aryl group means a carbocyclic aromatic group such as a phenyl group and a naphthyl group, and a heterocyclic aromatic group such as a furyl group, a thienyl group and a pyridyl group. In the compound represented by the general formula (1-A), preferably, X 1 to X 24 are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, and 1 to 20 carbon atoms. Represents a linear, branched or cyclic alkoxy group or a substituted or unsubstituted aryl group having 4 to 20 carbon atoms.
【0014】一般式(1−A)における、X1〜X24の
具体例としては、例えば、水素原子、例えば、フッ素原
子、塩素原子、臭素原子などのハロゲン原子;例えば、
メチル基、エチル基、n−プロピル基、イソプロピル
基、n−ブチル基、イソブチル基、sec−ブチル基、ter
t−ブチル基、n−ペンチル基、イソペンチル基、ネオ
ペンチル基、tert−ペンチル基、n−ヘキシル基、1−
メチルペンチル基、4−メチル−2−ペンチル基、3,
3−ジメチルブチル基、2−エチルブチル基、n−ヘプ
チル基、1−メチルヘキシル基、シクロヘキシルメチル
基、n−オクチル基、tert−オクチル基、1−メチルヘ
プチル基、2−エチルヘキシル基、2−プロピルペンチ
ル基、n−ノニル基、2,2−ジメチルヘプチル基、
2,6−ジメチル−4−ヘプチル基、3,5,5−トリ
メチルヘキシル基、n−デシル基、n−ウンデシル基、
1−メチルデシル基、n−ドデシル基、n−トリデシル
基、1−ヘキシルヘプチル基、n−テトラデシル基、n
−ペンタデシル基、n−ヘキサデシル基、n−ヘプタデ
シル基、n−オクタデシル基、n−エイコシル基、シク
ロペンチル基、シクロヘキシル基、4−メチルシクロヘ
キシル基、4−tert−ブチルシクロヘキシル基、シクロ
ヘプチル基、シクロオクチル基などの直鎖、分岐または
環状のアルキル基;Specific examples of X 1 to X 24 in the general formula (1-A) include, for example, a hydrogen atom, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom;
Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, ter
t-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-
Methylpentyl group, 4-methyl-2-pentyl group, 3,
3-dimethylbutyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, cyclohexylmethyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propyl Pentyl group, n-nonyl group, 2,2-dimethylheptyl group,
2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, n-undecyl group,
1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n
-Pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-eicosyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl Linear, branched or cyclic alkyl groups such as groups;
【0015】例えば、メトキシ基、エトキシ基、n−プ
ロポキシ基、イソプロポキシ基、n−ブトキシ基、イソ
ブトキシ基、sec−ブトキシ基、tert−ブトキシ基、n
−ペンチルオキシ基、ネオペンチルオキシ基、シクロペ
ンチルオキシ基、n−ヘキシルオキシ基、3,3−ジメ
チルブチルオキシ基、2−エチルブチルオキシ基、シク
ロヘキシルオキシ基、n−ヘプチルオキシ基、n−オク
チルオキシ基、2−エチルヘキシルオキシ基、n−ノニ
ルオキシ基、n−デシルオキシ基、n−ウンデシルオキ
シ基、n−ドデシルオキシ基、n−トリデシルオキシ
基、n−テトラデシルオキシ基、n−ペンタデシルオキ
シ基、n−ヘキサデシルオキシ基、n−ヘプタデシルオ
キシ基、n−オクタデシルオキシ基、n−エイコシルオ
キシ基などの直鎖、分岐または環状のアルコキシ基;For example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n
-Pentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy Group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-undecyloxy group, n-dodecyloxy group, n-tridecyloxy group, n-tetradecyloxy group, n-pentadecyloxy A linear, branched or cyclic alkoxy group such as a group, an n-hexadecyloxy group, an n-heptadecyloxy group, an n-octadecyloxy group, an n-eicosyloxy group;
【0016】例えば、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、4−n−プロピルフェニル基、4
−イソプロピルフェニル基、4−n−ブチルフェニル
基、4−イソブチルフェニル基、4−tert−ブチルフェ
ニル基、4−イソペンチルフェニル基、4−tert−ペン
チルフェニル基、4−n−ヘキシルフェニル基、4−シ
クロヘキシルフェニル基、4−n−ヘプチルフェニル
基、4−n−オクチルフェニル基、4−n−ノニルフェ
ニル基、4−n−デシルフェニル基、4−n−ウンデシ
ルフェニル基、4−n−ドデシルフェニル基、4−n−
テトラデシルフェニル基、2,3−ジメチルフェニル
基、2,4−ジメチルフェニル基、2,5−ジメチルフ
ェニル基、2,6−ジメチルフェニル基、3,4−ジメ
チルフェニル基、3,5−ジメチルフェニル基、3,
4,5−トリメチルフェニル基、2,3,5,6−テト
ラメチルフェニル基、5−インダニル基、1,2,3,
4−テトラヒドロ−5−ナフチル基、1,2,3,4−
テトラヒドロ−6−ナフチル基、2−メトキシフェニル
基、3−メトキシフェニル基、4−メトキシフェニル
基、3−エトキシフェニル基、4−エトキシフェニル
基、4−n−プロポキシフェニル基、4−イソプロポキ
シフェニル基、4−n−ブトキシフェニル基、4−イソ
ブトキシフェニル基、4−n−ペンチルオキシフェニル
基、4−n−ヘキシルオキシフェニル基、4−シクロヘ
キシルオキシフェニル基、4−n−ヘプチルオキシフェ
ニル基、4−n−オクチルオキシフェニル基、4−n−
ノニルオキシフェニル基、4−n−デシルオキシフェニ
ル基、4−n−ウンデシルオキシフェニル基、4−n−
ドデシルオキシフェニル基、4−n−テトラデシルオキ
シフェニル基、For example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4
-Ethylphenyl group, 4-n-propylphenyl group, 4
-Isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-tert-butylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4-n-nonylphenyl group, 4-n-decylphenyl group, 4-n-undecylphenyl group, 4-n -Dodecylphenyl group, 4-n-
Tetradecylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethyl Phenyl group, 3,
4,5-trimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 5-indanyl group, 1,2,3
4-tetrahydro-5-naphthyl group, 1,2,3,4-
Tetrahydro-6-naphthyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl group, 4-n-propoxyphenyl group, 4-isopropoxyphenyl Group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 4-n-pentyloxyphenyl group, 4-n-hexyloxyphenyl group, 4-cyclohexyloxyphenyl group, 4-n-heptyloxyphenyl group , 4-n-octyloxyphenyl group, 4-n-
Nonyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-undecyloxyphenyl group, 4-n-
Dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group,
【0017】2,3−ジメトキシフェニル基、2,4−
ジメトキシフェニル基、2,5−ジメトキシフェニル
基、3,4−ジメトキシフェニル基、3,5−ジメトキ
シフェニル基、3,5−ジエトキシフェニル基、2−メ
トキシ−4−メチルフェニル基、2−メトキシ−5−メ
チルフェニル基、2−メチル−4−メトキシフェニル
基、3−メチル−4−メトキシフェニル基、3−メチル
−5−メトキシフェニル基、2−フルオロフェニル基、
3−フルオロフェニル基、4−フルオロフェニル基、2
−クロロフェニル基、3−クロロフェニル基、4−クロ
ロフェニル基、4−ブロモフェニル基、4−トリフルオ
ロメチルフェニル基、2,4−ジフルオロフェニル基、
2,4−ジクロロフェニル基、3,4−ジクロロフェニ
ル基、3,5−ジクロロフェニル基、2−メチル−4−
クロロフェニル基、2−クロロ−4−メチルフェニル
基、3−クロロ−4−メチルフェニル基、2−クロロ−
4−メトキシフェニル基、3−メトキシ−4−フルオロ
フェニル基、3−メトキシ−4−クロロフェニル基、3
−フルオロ−4−メトキシフェニル基、4−フェニルフ
ェニル基、3−フェニルフェニル基、4−(4’−メチ
ルフェニル)フェニル基、4−(4’−メトキシフェニ
ル)フェニル基、1−ナフチル基、2−ナフチル基、4
−メチル−1−ナフチル基、4−エトキシ−1−ナフチ
ル基、6−n−ブチル−2−ナフチル基、6−メトキシ
−2−ナフチル基、7−エトキシ−2−ナフチル基、2
−フリル基、2−チエニル基、3−チエニル基、2−ピ
リジル基、3−ピリジル基、4−ピリジル基などの置換
または未置換のアリール基を挙げることができる。2,3-dimethoxyphenyl group, 2,4-
Dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 2-methoxy-4-methylphenyl group, 2-methoxy -5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 2-fluorophenyl group,
3-fluorophenyl group, 4-fluorophenyl group, 2
-Chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-trifluoromethylphenyl group, 2,4-difluorophenyl group,
2,4-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-methyl-4-
Chlorophenyl group, 2-chloro-4-methylphenyl group, 3-chloro-4-methylphenyl group, 2-chloro-
4-methoxyphenyl group, 3-methoxy-4-fluorophenyl group, 3-methoxy-4-chlorophenyl group, 3
-Fluoro-4-methoxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (4'-methoxyphenyl) phenyl group, 1-naphthyl group, 2-naphthyl group, 4
-Methyl-1-naphthyl group, 4-ethoxy-1-naphthyl group, 6-n-butyl-2-naphthyl group, 6-methoxy-2-naphthyl group, 7-ethoxy-2-naphthyl group, 2
And substituted or unsubstituted aryl groups such as -furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl and 4-pyridyl.
【0018】より好ましくは、水素原子、フッ素原子、
塩素原子、炭素数1〜10のアルキル基、炭素数1〜1
0のアルコキシ基、あるいは、炭素数6〜12のアリー
ル基であり、さらに好ましくは、水素原子、フッ素原
子、塩素原子、炭素数1〜6のアルキル基、炭素数1〜
6のアルコキシ基、あるいは、炭素数6〜10のアリー
ル基である。More preferably, a hydrogen atom, a fluorine atom,
Chlorine atom, C1-C10 alkyl group, C1-C1
An alkoxy group having 0 or an aryl group having 6 to 12 carbon atoms, more preferably a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 6 carbon atoms,
It is an alkoxy group having 6 or an aryl group having 6 to 10 carbon atoms.
【0019】本発明の有機電界発光素子においては、
1,4−ジ(3’−フルオランテニル)ナフタレン誘導
体を少なくとも一種使用することが特徴であり、例え
ば、1,4−ジ(3’−フルオランテニル)ナフタレン
誘導体を発光成分として発光層に用いると、従来にはな
い、高輝度で耐久性に優れた青緑色〜黄緑色に発光する
有機電界発光素子を提供することが可能となる。また、
他の発光成分と組み合わせて発光層を形成すると、高輝
度で耐久性に優れた白色に発光する有機電界発光素子も
提供することが可能となる。In the organic electroluminescent device of the present invention,
It is characterized in that at least one 1,4-di (3′-fluoranthenyl) naphthalene derivative is used. For example, a 1,4-di (3′-fluoranthenyl) naphthalene derivative is used as a light-emitting component in a light-emitting layer. When used, it is possible to provide an organic electroluminescent element that emits blue-green to yellow-green light, which is high in brightness and has excellent durability, which has not existed conventionally. Also,
When a light-emitting layer is formed in combination with another light-emitting component, an organic electroluminescent element that emits white light with high luminance and excellent durability can be provided.
【0020】本発明に係る化合物Aの具体例としては、
例えば、以下の化合物(化6〜化35)を挙げることが
できるが、本発明はこれらに限定されるものではない。Specific examples of the compound A according to the present invention include:
For example, the following compounds (Chemical Formulas 6 to 35) can be exemplified, but the present invention is not limited thereto.
【0021】[0021]
【化6】 Embedded image
【0022】[0022]
【化7】 Embedded image
【0023】[0023]
【化8】 Embedded image
【0024】[0024]
【化9】 Embedded image
【0025】[0025]
【化10】 Embedded image
【0026】[0026]
【化11】 Embedded image
【0027】[0027]
【化12】 Embedded image
【0028】[0028]
【化13】 Embedded image
【0029】[0029]
【化14】 Embedded image
【0030】[0030]
【化15】 Embedded image
【0031】[0031]
【化16】 Embedded image
【0032】[0032]
【化17】 Embedded image
【0033】[0033]
【化18】 Embedded image
【0034】[0034]
【化19】 Embedded image
【0035】[0035]
【化20】 Embedded image
【0036】[0036]
【化21】 Embedded image
【0037】[0037]
【化22】 Embedded image
【0038】[0038]
【化23】 Embedded image
【0039】[0039]
【化24】 Embedded image
【0040】[0040]
【化25】 Embedded image
【0041】[0041]
【化26】 Embedded image
【0042】[0042]
【化27】 Embedded image
【0043】[0043]
【化28】 Embedded image
【0044】[0044]
【化29】 Embedded image
【0045】[0045]
【化30】 Embedded image
【0046】[0046]
【化31】 Embedded image
【0047】[0047]
【化32】 Embedded image
【0048】[0048]
【化33】 Embedded image
【0049】[0049]
【化34】 Embedded image
【0050】[0050]
【化35】 Embedded image
【0051】本発明に係る化合物A、例えば、一般式
(1−A)で表される化合物は、例えば、以下の方法に
より製造することができる。すなわち、例えば、一般式
(2)(化36)および一般式(3)(化36)で表さ
れる3−フルオランテニルホウ酸誘導体を、一般式
(4)(化37)で表されるジハロゲノナフタレン誘導
体と、例えば、パラジウム化合物〔例えば、テトラキス
(トリフェニルフォスフィン)パラジウム、ビス(トリ
フェニルフォスフィン)パラジウムクロライド〕および
塩基(例えば、炭酸ナトリウム、炭酸水素ナトリウム、
トリエチルアミン)の存在下で反応させる〔例えば、Ch
em.Rev.,95,2457(1995)に記載の方法を参考にすること
ができる〕ことにより製造することができる。The compound A according to the present invention, for example, the compound represented by the general formula (1-A) can be produced, for example, by the following method. That is, for example, the 3-fluoranthenyl boric acid derivative represented by the general formula (2) (Formula 36) and the general formula (3) (Formula 36) is converted into the general formula (4) (Formula 37). A dihalogenonaphthalene derivative, for example, a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium chloride] and a base (eg, sodium carbonate, sodium hydrogen carbonate,
Triethylamine) (eg, Ch
Em. Rev., 95 , 2457 (1995) can be referred to].
【0052】[0052]
【化36】 Embedded image
【0053】〔上式中、X1〜X24は、一般式(1−
A)の場合と同じ意味を表し、Z1およびZ2はハロゲン
原子を表す。〕In the above formula, X 1 to X 24 are represented by the general formula (1-
It has the same meaning as in the case of A), and Z 1 and Z 2 represent a halogen atom. ]
【0054】一般式(4)において、Z1およびZ2はハ
ロゲン原子を表し、好ましくは、塩素原子、臭素原子、
ヨウ素原子を表す。In the general formula (4), Z 1 and Z 2 represent a halogen atom, preferably a chlorine atom, a bromine atom,
Represents an iodine atom.
【0055】尚、一般式(2)および一般式(3)で表
される化合物は、例えば、一般式(5)(化37)およ
び一般式(6)(化37)で表される化合物より、例え
ば、n−ブチルリチウム、金属マグネシウムを作用させ
て調整できるリチオ化合物またはグリニヤール試薬と、
例えば、トリメトキシホウ素、トリイソプロポキシホウ
素などにより調整することができる〔例えば、Chem.Re
v.,95,2457(1995)に記載の方法を参考にすることができ
る〕。The compounds represented by the general formulas (2) and (3) are, for example, the compounds represented by the general formulas (5) and (6) and the chemical formulas (6) and (37). For example, n-butyllithium, a lithio compound or a Grignard reagent that can be adjusted by the action of metallic magnesium,
For example, it can be adjusted with trimethoxyboron, triisopropoxyboron and the like (for example, Chem.Re.
v., 95 , 2457 (1995) can be referred to].
【0056】[0056]
【化37】 Embedded image
【0057】〔上式中、X1〜X7、X12〜X20、X23お
よびX24は、一般式(1−A)の場合と同じ意味を表
し、Z3およびZ4はハロゲン原子を表す。〕[In the above formula, X 1 to X 7 , X 12 to X 20 , X 23 and X 24 have the same meanings as in the general formula (1-A), and Z 3 and Z 4 represent a halogen atom Represents ]
【0058】一般式(5)および一般式(6)におい
て、Z3およびZ4はハロゲン原子を表し、好ましくは、
塩素原子、臭素原子、ヨウ素原子を表す。In the general formulas (5) and (6), Z 3 and Z 4 each represent a halogen atom.
Represents chlorine, bromine and iodine atoms.
【0059】本発明に係る化合物Aは、場合により使用
した溶媒(例えば、トルエンなどの芳香族炭化水素系溶
媒)との溶媒和を形成した形で製造されることがある
が、本発明においては、本発明に係る化合物Aはこのよ
うな溶媒和物を包含するものである。勿論、溶媒を含有
しない無溶媒和物をも包含するものである。本発明の有
機電界発光素子には、本発明に係る化合物Aの無溶媒和
物は勿論、このような溶媒和物をも使用することができ
る。尚、本発明に係る化合物Aを有機電界発光素子に使
用する場合、再結晶法、カラムクロマトグラフィー法、
昇華精製法などの精製方法、あるいはこれらの方法を併
用して、純度を高めた化合物を使用することは好ましい
ことである。The compound A according to the present invention may be produced in the form of a solvation with a solvent (for example, an aromatic hydrocarbon solvent such as toluene) used in some cases. The compound A according to the present invention includes such a solvate. Needless to say, a non-solvate containing no solvent is also included. In the organic electroluminescent device of the present invention, not only a non-solvate of the compound A according to the present invention but also such a solvate can be used. When the compound A according to the present invention is used in an organic electroluminescent device, a recrystallization method, a column chromatography method,
It is preferable to use a purification method such as a sublimation purification method, or a compound having an increased purity by using these methods in combination.
【0060】有機電界発光素子は、通常、一対の電極間
に、少なくとも一種の発光成分を含有する発光層を、少
なくとも一層挟持してなるものである。発光層に使用す
る化合物の正孔注入および正孔輸送、電子注入および電
子輸送の各機能レベルを考慮し、所望に応じて、正孔注
入輸送成分を含有する正孔注入輸送層および/または電
子注入輸送成分を含有する電子注入輸送層を設けること
もできる。例えば、発光層に使用する化合物の正孔注入
機能、正孔輸送機能および/または電子注入機能、電子
輸送機能が良好な場合には、発光層が正孔注入輸送層お
よび/または電子注入輸送層を兼ねた型の素子の構成と
することができる。勿論、場合によっては、正孔注入輸
送層および電子注入輸送層の両方の層を設けない型の素
子(一層型の素子)の構成とすることもできる。また、
正孔注入輸送層、電子注入輸送層および発光層のそれぞ
れの層は、一層構造であっても、また、多層構造であっ
てもよく、正孔注入輸送層および電子注入輸送層は、そ
れぞれの層において、注入機能を有する層と輸送機能を
有する層を別々に設けて構成することもできる。The organic electroluminescent device generally has at least one light-emitting layer containing at least one light-emitting component sandwiched between a pair of electrodes. In consideration of the functional levels of hole injection and hole transport, electron injection and electron transport of the compound used in the light emitting layer, a hole injection transport layer containing a hole injection transport component and / or An electron injection / transport layer containing an injection / transport component can also be provided. For example, when the compound used for the light emitting layer has a good hole injection function, a hole transport function and / or an electron injection function, and an electron transport function, the light emitting layer is formed of the hole injection transport layer and / or the electron injection transport layer. The element can also be configured to serve as Needless to say, depending on the case, a structure of a device (single-layer device) in which both the hole injection transport layer and the electron injection transport layer are not provided may be employed. Also,
Each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single-layer structure or a multilayer structure, and the hole injecting and transporting layer and the electron injecting and transporting layer may have respective structures. In the layer, a layer having an injection function and a layer having a transport function may be separately provided.
【0061】本発明の有機電界発光素子において、本発
明に係る化合物Aは、正孔注入輸送成分、発光成分また
は電子注入輸送成分に用いることが好ましく、正孔注入
輸送成分または発光成分に用いることがより好ましく、
発光成分に用いることが特に好ましい。本発明の有機電
界発光素子においては、本発明に係る化合物Aは、単独
で使用してもよく、あるいは複数併用してもよい。In the organic electroluminescent device of the present invention, the compound A according to the present invention is preferably used for a hole injecting and transporting component, a light emitting component or an electron injecting and transporting component. Is more preferable,
It is particularly preferable to use it for a light emitting component. In the organic electroluminescent device of the present invention, the compound A according to the present invention may be used alone or in combination.
【0062】本発明の有機電界発光素子の構成として
は、特に限定するものではなく、例えば、(A)陽極/
正孔注入輸送層/発光層/電子注入輸送層/陰極型素子
(図1)、(B)陽極/正孔注入輸送層/発光層/陰極
型素子(図2)、(C)陽極/発光層/電子注入輸送層
/陰極型素子(図3)、(D)陽極/発光層/陰極型素
子(図4)などを挙げることができる。さらには、発光
層を電子注入輸送層で挟み込んだ型の素子である(E)
陽極/正孔注入輸送層/電子注入輸送層/発光層/電子
注入輸送層/陰極型素子(図5)とすることもできる。
(D)型の素子構成としては、発光成分を一層形態で一
対の電極間に挟持させた型の素子を包含するものである
が、さらには、例えば、(F)正孔注入輸送成分、発光
成分および電子注入輸送成分を混合させた一層形態で一
対の電極間に挟持させた型の素子(図6)、(G)正孔
注入輸送成分および発光成分を混合させた一層形態で一
対の電極間に挟持させた型の素子(図7)、(H)発光
成分および電子注入輸送成分を混合させた一層形態で一
対の電極間に挟持させた型の素子(図8)がある。The structure of the organic electroluminescent device of the present invention is not particularly limited.
(B) anode / hole injection / transport layer / light emitting layer / cathode device (FIG. 2), (C) anode / light emission Layer / electron injection / transport layer / cathode device (FIG. 3), (D) anode / light-emitting layer / cathode device (FIG. 4), and the like. Further, the device is a device of a type in which a light emitting layer is sandwiched between electron injection transport layers (E).
Anode / hole injection / transport layer / electron injection / transport layer / emission layer / electron injection / transport layer / cathode device (FIG. 5).
The element configuration of the (D) type includes an element of a type in which a light-emitting component is sandwiched between a pair of electrodes in a single layer form. Further, for example, (F) a hole injection / transport component, (FIG. 6), and a pair of electrodes in the form of a single layer in which the hole injection / transport component and the light emitting component are mixed. There is an element of the type sandwiched between (FIG. 7) and (H) an element of the type sandwiched between a pair of electrodes (FIG. 8) in the form of a single layer in which a light emitting component and an electron injection transport component are mixed.
【0063】本発明の有機電界発光素子においては、こ
れらの素子構成に限るものではなく、それぞれの型の素
子において、正孔注入輸送層、発光層、電子注入輸送層
を複数層設けたりすることができる。また、それぞれの
型の素子において、正孔注入輸送層と発光層との間に、
正孔注入輸送成分と発光成分の混合層および/または発
光層と電子注入輸送層との間に、発光成分と電子注入輸
送成分の混合層を設けることもできる。より好ましい有
機電界発光素子の構成は、(A)型素子、(B)型素
子、(C)型素子、(E)型素子、(F)型素子、
(G)型素子または(H)型素子であり、さらに好まし
くは、(A)型素子、(B)型素子、(C)型素子、
(F)型素子、または(H)型素子である。本発明の有
機電界発光素子としては、例えば、(図1)に示す
(A)陽極/正孔注入輸送層/発光層/電子注入輸送層
/陰極型素子について説明する。(図1)において、1
は基板、2は陽極、3は正孔注入輸送層、4は発光層、
5は電子注入輸送層、6は陰極、7は電源を示す。The organic electroluminescent device of the present invention is not limited to these device configurations, but may be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers in each type of device. Can be. In each type of device, between the hole injection transport layer and the light emitting layer,
A mixed layer of a light emitting component and an electron injecting and transporting component may be provided between the light emitting layer and the electron injecting and transporting layer. More preferred configurations of the organic electroluminescent element include (A) type element, (B) type element, (C) type element, (E) type element, (F) type element,
(G) type element or (H) type element, more preferably (A) type element, (B) type element, (C) type element,
(F) type element or (H) type element. As the organic electroluminescent device of the present invention, for example, (A) anode / hole injection / transport layer / emission layer / electron injection / transport layer / cathode device shown in FIG. 1 will be described. (FIG. 1)
Is a substrate, 2 is an anode, 3 is a hole injection / transport layer, 4 is a light emitting layer,
Reference numeral 5 denotes an electron injection / transport layer, 6 denotes a cathode, and 7 denotes a power supply.
【0064】本発明の電界発光素子は、基板1に支持さ
れていることが好ましく、基板としては、特に限定する
ものではないが、透明ないし半透明であることが好まし
く、例えば、ガラス板、透明プラスチックシート(例え
ば、ポリエステル、ポリカーボネート、ポリスルフォ
ン、ポリメチルメタクリレート、ポリプロピレン、ポリ
エチレンなどのシート)、半透明プラスチックシート、
石英、透明セラミクッスあるいはこれらを組み合わせた
複合シートからなるものを挙げることができる。さら
に、基板に、例えば、カラーフィルター膜、色変換膜、
誘電体反射膜を組み合わせて、発光色をコントロールす
ることもできる。The electroluminescent device of the present invention is preferably supported on a substrate 1, and the substrate is not particularly limited, but is preferably transparent or translucent. Plastic sheets (eg, sheets of polyester, polycarbonate, polysulfone, polymethyl methacrylate, polypropylene, polyethylene, etc.), translucent plastic sheets,
Quartz, transparent ceramics, or a composite sheet combining these can be used. Further, on the substrate, for example, a color filter film, a color conversion film,
Emission color can also be controlled by combining dielectric reflection films.
【0065】陽極2としては、比較的仕事関数の大きい
金属、合金または電気伝導性化合物を電極物質として使
用することが好ましい。陽極に使用する電極物質として
は、例えば、金、白金、銀、銅、コバルト、ニッケル、
パラジウム、バナジウム、タングステン、酸化錫、酸化
亜鉛、ITO(インジウム・ティン・オキサイド)、ポ
リチオフェン、ポリピロールなどを挙げることができ
る。これらの電極物質は、単独で使用してもよく、ある
いは複数併用してもよい。陽極は、これらの電極物質を
用いて、例えば、蒸着法、スパッタリング法などの方法
により、基板の上に形成することができる。また、陽極
は一層構造であってもよく、あるいは多層構造であって
もよい。陽極のシート電気抵抗は、好ましくは、数百Ω
/□以下、より好ましくは、5〜50Ω/□程度に設定
する。陽極の厚みは、使用する電極物質の材料にもよる
が、一般に、5〜1000nm程度、より好ましくは、
10〜500nm程度に設定する。As the anode 2, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively large work function as an electrode material. As the electrode material used for the anode, for example, gold, platinum, silver, copper, cobalt, nickel,
Palladium, vanadium, tungsten, tin oxide, zinc oxide, ITO (indium tin oxide), polythiophene, polypyrrole, and the like can be given. These electrode substances may be used alone or in combination of two or more. The anode can be formed on a substrate by using such an electrode material by a method such as an evaporation method or a sputtering method. Further, the anode may have a single-layer structure or a multilayer structure. The sheet electric resistance of the anode is preferably several hundred Ω.
/ □ or less, more preferably about 5 to 50Ω / □. The thickness of the anode depends on the material of the electrode substance used, but is generally about 5 to 1000 nm, more preferably,
It is set to about 10 to 500 nm.
【0066】正孔注入輸送層3は、陽極からの正孔(ホ
ール)の注入を容易にする機能、および注入された正孔
を輸送する機能を有する化合物を含有する層である。正
孔注入輸送層は、本発明に係る化合物Aおよび/または
他の正孔注入輸送機能を有する化合物(例えば、フタロ
シアニン誘導体、トリアリールメタン誘導体、トリアリ
ールアミン誘導体、オキサゾール誘導体、ヒドラゾン誘
導体、スチルベン誘導体、ピラゾリン誘導体、ポリシラ
ン誘導体、ポリフェニレンビニレンおよびその誘導体、
ポリチオフェンおよびその誘導体、ポリ−N−ビニルカ
ルバゾール誘導体など)を少なくとも一種用いて形成す
ることができる。尚、正孔注入輸送機能を有する化合物
は、単独で使用してもよく、あるいは複数併用してもよ
い。The hole injection / transport layer 3 is a layer containing a compound having a function of facilitating the injection of holes (holes) from the anode and a function of transporting the injected holes. The hole injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having a hole injecting and transporting function (for example, phthalocyanine derivative, triarylmethane derivative, triarylamine derivative, oxazole derivative, hydrazone derivative, stilbene derivative) , Pyrazoline derivatives, polysilane derivatives, polyphenylenevinylene and its derivatives,
Polythiophene and a derivative thereof, a poly-N-vinylcarbazole derivative, or the like). The compounds having a hole injection / transport function may be used alone or in combination.
【0067】本発明において用いる他の正孔注入輸送機
能を有する化合物としては、トリアリールアミン誘導体
(例えば、4,4’−ビス〔N−フェニル−N−(4”
−メチルフェニル)アミノ〕ビフェニル、4,4’−ビ
ス〔N−フェニル−N−(3”−メチルフェニル)アミ
ノ〕ビフェニル、4,4’−ビス〔N−フェニル−N−
(3”−メトキシフェニル)アミノ〕ビフェニル、4,
4’−ビス〔N−フェニル−N−(1”−ナフチル)ア
ミノ〕ビフェニル、3,3’−ジメチル−4,4’−ビ
ス〔N−フェニル−N−(3”−メチルフェニル)アミ
ノ〕ビフェニル、1,1−ビス〔4’−[N,N−ジ
(4”−メチルフェニル)アミノ]フェニル〕シクロヘ
キサン、9,10−ビス〔N−(4’−メチルフェニ
ル)−N−(4”−n−ブチルフェニル)アミノ〕フェ
ナントレン、3,8−ビス(N,N−ジフェニルアミ
ノ)−6−フェニルフェナントリジン、4−メチル−
N,N−ビス〔4”,4'''−ビス[N’,N’−ジ
(4−メチルフェニル)アミノ]ビフェニル−4−イ
ル〕アニリン、N,N’−ビス〔4−(ジフェニルアミ
ノ)フェニル〕−N,N’−ジフェニル−1,3−ジア
ミノベンゼン、N,N’−ビス〔4−(ジフェニルアミ
ノ)フェニル〕−N,N’−ジフェニル−1,4−ジア
ミノベンゼン、5,5”−ビス〔4−(ビス[4−メチ
ルフェニル]アミノ)フェニル〕−2,2’:5’,
2”−ターチオフェン、1,3,5−トリス(ジフェニ
ルアミノ)ベンゼン、4,4’,4”−トリス(N−カ
ルバゾリイル)トリフェニルアミン、4,4’,4”−
トリス〔N−(3'''−メチルフェニル)−N−フェニ
ルアミノ〕トリフェニルアミン、4,4’,4”−トリ
ス〔N,N−ビス(4'''−tert−ブチルビフェニル−
4""−イル)アミノ〕トリフェニルアミン、1,3,5
−トリス〔N−(4’−ジフェニルアミノフェニル)−
N−フェニルアミノ〕ベンゼンなど)、ポリチオフェン
およびその誘導体、ポリ−N−ビニルカルバゾール誘導
体が好ましい。本発明に係る化合物Aと他の正孔注入輸
送機能を有する化合物を併用する場合、正孔注入輸送層
中に占める本発明に係る化合物Aの割合は、好ましく
は、0.1〜40重量%程度に調製する。Other compounds having a hole injection / transport function used in the present invention include triarylamine derivatives (for example, 4,4′-bis [N-phenyl-N- (4 ″)).
-Methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N-
(3 "-methoxyphenyl) amino] biphenyl, 4,
4'-bis [N-phenyl-N- (1 "-naphthyl) amino] biphenyl, 3,3'-dimethyl-4,4'-bis [N-phenyl-N- (3" -methylphenyl) amino] Biphenyl, 1,1-bis [4 ′-[N, N-di (4 ″ -methylphenyl) amino] phenyl] cyclohexane, 9,10-bis [N- (4′-methylphenyl) -N- (4 "-N-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-
N, N-bis [4 ″, 4 ″ ′-bis [N ′, N′-di (4-methylphenyl) amino] biphenyl-4-yl] aniline, N, N′-bis [4- (diphenyl Amino) phenyl] -N, N′-diphenyl-1,3-diaminobenzene, N, N′-bis [4- (diphenylamino) phenyl] -N, N′-diphenyl-1,4-diaminobenzene, 5 , 5 "-bis [4- (bis [4-methylphenyl] amino) phenyl] -2,2 ': 5',
2 "-terthiophene, 1,3,5-tris (diphenylamino) benzene, 4,4 ', 4" -tris (N-carbazolyyl) triphenylamine, 4,4', 4 "-
Tris [N- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine, 4,4 ′, 4 ″ -tris [N, N-bis (4 ′ ″-tert-butylbiphenyl-
4 ""-yl) amino] triphenylamine, 1,3,5
-Tris [N- (4'-diphenylaminophenyl)-
N-phenylamino] benzene, etc.), polythiophene and derivatives thereof, and poly-N-vinylcarbazole derivatives are preferred. When the compound A according to the present invention is used in combination with another compound having a hole injecting and transporting function, the proportion of the compound A according to the present invention in the hole injecting and transporting layer is preferably 0.1 to 40% by weight. Prepare to about.
【0068】発光層4は、正孔および電子の注入機能、
それらの輸送機能、正孔と電子の再結合により励起子を
生成させる機能を有する化合物を含有する層である。発
光層は、本発明に係る化合物Aおよび/または他の発光
機能を有する化合物(例えば、アクリドン誘導体、キナ
クリドン誘導体、ジケトピロロピロール誘導体、多環芳
香族化合物〔例えば、ルブレン、アントラセン、テトラ
セン、ピレン、ペリレン、クリセン、デカシクレン、コ
ロネン、テトラフェニルシクロペンタジエン、ペンタフ
ェニルシクロヘキサジエン、9,10−ジフェニルアン
トラセン、9,10−ビス(フェニルエチニル)アント
ラセン、1,4−ビス(9’−エチニルアントラセニ
ル)ベンゼン、4,4’−ビス(9”−エチニルアント
ラセニル)ビフェニル〕、トリアリールアミン誘導体
〔例えば、正孔注入輸送機能を有する化合物として前述
した化合物を挙げることができる〕、有機金属錯体〔例
えば、トリス(8−キノリラート)アルミニウム、ビス
(10−ベンゾ[h]キノリノラート)ベリリウム、2−
(2’−ヒドロキシフェニル)ベンゾオキサゾールの亜
鉛塩、2−(2’−ヒドロキシフェニル)ベンゾチアゾ
ールの亜鉛塩、4−ヒドロキシアクリジンの亜鉛塩、3
−ヒドロキシフラボンの亜鉛塩、5−ヒドロキシフラボ
ンのベリリウム塩、5−ヒドロキシフラボンのアルミニ
ウム塩〕、スチルベン誘導体〔例えば、1,1,4,4
−テトラフェニル−1,3−ブタジエン、4,4’−ビ
ス(2,2−ジフェニルビニル)ビフェニル、4,4’
−ビス〔(1,1,2−トリフェニル)エテニル〕ビフ
ェニル、クマリン誘導体〔例えば、クマリン1、クマリ
ン6、クマリン7、クマリン30、クマリン106、ク
マリン138、クマリン151、クマリン152、クマ
リン153、クマリン307、クマリン311、クマリ
ン314、クマリン334、クマリン338、クマリン
343、クマリン500〕、ピラン誘導体〔例えば、D
CM1、DCM2〕、オキサゾン誘導体〔例えば、ナイ
ルレッド〕、ベンゾチアゾール誘導体、ベンゾオキサゾ
ール誘導体、ベンゾイミダゾール誘導体、ピラジン誘導
体、ケイ皮酸エステル誘導体、ポリ−N−ビニルカルバ
ゾールおよびその誘導体、ポリチオフェンおよびその誘
導体、ポリフェニレンおよびその誘導体、ポリフルオレ
ンおよびその誘導体、ポリフェニレンビニレンおよびそ
の誘導体、ポリビフェニレンビニレンおよびその誘導
体、ポリターフェニレンビニレンおよびその誘導体、ポ
リナフチレンビニレンおよびその誘導体、ポリチエニレ
ンビニレンおよびその誘導体など)を少なくとも一種用
いて形成することができる。本発明の有機電界発光素子
においては、発光層に本発明に係る化合物Aを含有して
いることが好ましい。本発明に係る化合物Aと他の発光
機能を有する化合物を併用する場合、発光層中に占める
本発明に係る化合物Aの割合は、好ましくは、0.00
1〜99.999重量%程度、より好ましくは、0.0
1〜99.99重量%程度、さらに好ましくは、0.1
〜99.9重量%程度に調製する。The light emitting layer 4 has a hole and electron injection function,
This is a layer containing a compound having a transport function thereof and a function of generating excitons by recombination of holes and electrons. The light-emitting layer is formed of the compound A according to the present invention and / or another compound having a light-emitting function (eg, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [eg, rubrene, anthracene, tetracene, pyrene). , Perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclohexadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthracenyl) ) Benzene, 4,4′-bis (9 ″ -ethynylanthracenyl) biphenyl], a triarylamine derivative [for example, the compounds described above as compounds having a hole injecting and transporting function], and organometallic complexes [For example, Tris (8- Rirato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 2-
Zinc salt of (2′-hydroxyphenyl) benzoxazole, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine,
-Hydroxyflavone zinc salt, 5-hydroxyflavone beryllium salt, 5-hydroxyflavone aluminum salt], stilbene derivatives [for example, 1,1,4,4
-Tetraphenyl-1,3-butadiene, 4,4'-bis (2,2-diphenylvinyl) biphenyl, 4,4 '
-Bis [(1,1,2-triphenyl) ethenyl] biphenyl, coumarin derivatives [for example, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138, coumarin 151, coumarin 152, coumarin 153, coumarin 307, coumarin 311, coumarin 314, coumarin 334, coumarin 338, coumarin 343, coumarin 500], pyran derivative [for example, D
CM1, DCM2], oxazone derivative [for example, Nile Red], benzothiazole derivative, benzoxazole derivative, benzimidazole derivative, pyrazine derivative, cinnamate derivative, poly-N-vinylcarbazole and its derivatives, polythiophene and its derivatives, Polyphenylene and its derivatives, polyfluorene and its derivatives, polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and its derivatives, polythienylene vinylene and its derivatives) It can be formed using at least one kind. In the organic electroluminescent device of the present invention, the light emitting layer preferably contains the compound A according to the present invention. When the compound A according to the present invention and a compound having another light-emitting function are used in combination, the ratio of the compound A according to the present invention in the light-emitting layer is preferably 0.00
About 1-99.999% by weight, more preferably 0.0
About 1 to 99.99% by weight, more preferably 0.1
It is adjusted to about 99.9% by weight.
【0069】本発明において用いる他の発光機能を有す
る化合物としては、発光性有機金属錯体が好ましい。例
えば、J.Appl.Phys.,65,3610(1989)、特開平5−214
332号公報に記載のように、発光層をホスト化合物と
ゲスト化合物(ドーパント)とより構成することもでき
る。本発明に係る化合物Aを、ホスト化合物として用い
て発光層を形成することができ、さらには、ゲスト化合
物として用いて発光層を形成することもできる。本発明
に係る化合物Aを、ゲスト化合物として用いて発光層を
形成する場合、ホスト化合物としては、例えば、前記の
他の発光機能を有する化合物を挙げることができ、例え
ば、発光性有機金属錯体またはトリアリールアミンはよ
り好ましい。この場合、発光性有機金属錯体またはトリ
アリールアミン誘導体に対して、本発明に係る化合物A
を、好ましくは、0.001〜40重量%程度、より好
ましくは、0.01〜30重量%程度、特に好ましく
は、0.1〜20重量%程度使用する。As the other compound having a light-emitting function used in the present invention, a light-emitting organic metal complex is preferable. For example, J. Appl. Phys., 65 , 3610 (1989), JP-A-5-214.
As described in JP-A-332-332, the light-emitting layer can be composed of a host compound and a guest compound (dopant). The compound A according to the present invention can be used as a host compound to form a light emitting layer, and further can be used as a guest compound to form a light emitting layer. When the compound A according to the present invention is used as a guest compound to form a light-emitting layer, examples of the host compound include the compounds having the other light-emitting functions, such as a light-emitting organometallic complex or Triarylamines are more preferred. In this case, the compound A according to the present invention is used for the luminescent organometallic complex or the triarylamine derivative.
Is preferably used in an amount of about 0.001 to 40% by weight, more preferably about 0.01 to 30% by weight, and particularly preferably about 0.1 to 20% by weight.
【0070】本発明に係る化合物Aと併用する発光性有
機金属錯体としては、特に限定するものではないが、発
光性有機アルミニウム錯体が好ましく、置換または未置
換の8−キノリノラート配位子を有する発光性有機アル
ミニウム錯体がより好ましい。好ましい発光性有機金属
錯体としては、例えば、一般式(a)〜一般式(c)で
表される発光性有機アルミニウム錯体を挙げることがで
きる。 (Q)3−Al (a) (式中、Qは置換または未置換の8−キノリノラート配
位子を表す) (Q)2−Al−O−L (b) (式中、Qは置換8−キノリノラート配位子を表し、O
−Lはフェノラート配位子であり、Lはフェニル部分を
含む炭素数6〜24の炭化水素基を表す) (Q)2−Al−O−Al−(Q)2 (c) (式中、Qは置換8−キノリノラート配位子を表す) 発光性有機金属錯体の具体例としては、例えば、トリス
(8−キノリノラート)アルミニウム、トリス(4−メ
チル−8−キノリノラート)アルミニウム、トリス(5
−メチル−8−キノリノラート)アルミニウム、トリス
(3,4−ジメチル−8−キノリノラート)アルミニウ
ム、トリス(4,5−ジメチル−8−キノリノラート)
アルミニウム、トリス(4,6−ジメチル−8−キノリ
ノラート)アルミニウム、ビス(2−メチル−8−キノ
リノラート)(フェノラート)アルミニウム、ビス(2
−メチル−8−キノリノラート)(2−メチルフェノラ
ート)アルミニウム、ビス(2−メチル−8−キノリノ
ラート)(3−メチルフェノラート)アルミニウム、ビ
ス(2−メチル−8−キノリノラート)(4−メチルフ
ェノラート)アルミニウム、ビス(2−メチル−8−キ
ノリノラート)(2−フェニルフェノラート)アルミニ
ウム、ビス(2−メチル−8−キノリノラート)(3−
フェニルフェノラート)アルミニウム、ビス(2−メチ
ル−8−キノリノラート)(4−フェニルフェノラー
ト)アルミニウム、ビス(2−メチル−8−キノリノラ
ート)(2,3−ジメチルフェノラート)アルミニウ
ム、ビス(2−メチル−8−キノリノラート)(2,6
−ジメチルフェノラート)アルミニウム、ビス(2−メ
チル−8−キノリノラート)(3,4−ジメチルフェノ
ラート)アルミニウム、ビス(2−メチル−8−キノリ
ノラート)(3,5−ジメチルフェノラート)アルミニ
ウム、ビス(2−メチル−8−キノリノラート)(3,
5−ジ−tert−ブチルフェノラート)アルミニウム、ビ
ス(2−メチル−8−キノリノラート)(2,6−ジフ
ェニルフェノラート)アルミニウム、ビス(2−メチル
−8−キノリノラート)(2,4,6−トリフェニルフ
ェノラート)アルミニウム、ビス(2−メチル−8−キ
ノリノラート)(2,4,6−トリメチルフェノラー
ト)アルミニウム、ビス(2−メチル−8−キノリノラ
ート)(2,4,5,6−テトラメチルフェノラート)
アルミニウム、ビス(2−メチル−8−キノリノラー
ト)(1−ナフトラート)アルミニウム、ビス(2−メ
チル−8−キノリノラート)(2−ナフトラート)アル
ミニウム、ビス(2,4−ジメチル−8−キノリノラー
ト)(2−フェニルフェノラート)アルミニウム、ビス
(2,4−ジメチル−8−キノリノラート)(3−フェ
ニルフェノラート)アルミニウム、ビス(2,4−ジメ
チル−8−キノリノラート)(4−フェニルフェノラー
ト)アルミニウム、ビス(2,4−ジメチル−8−キノ
リノラート)(3,5−ジメチルフェニルフェノラー
ト)アルミニウム、ビス(2,4−ジメチル−8−キノ
リノラート)(3,5−ジ−tert−ブチルフェニルフェ
ノラート)アルミニウム、ビス(2−メチル−8−キノ
リノラート)アルミニウム−μ−オキソ−ビス(2−メ
チル−8−キノリノラート)アルミニウム、ビス(2,
4−ジメチル−8−キノリノラート)アルミニウム−μ
−オキソ−ビス(2,4−ジメチル−8−キノリノラー
ト)アルミニウム、ビス(2−メチル−4−エチル−8
−キノリノラート)アルミニウム−μ−オキソ−ビス
(2−メチル−4−エチル−8−キノリノラート)アル
ミニウム、ビス(2−メチル−4−メトキシ−8−キノ
リノラート)アルミニウム−μ−オキソ−ビス(2−メ
チル−4−メトキシ−8−キノリノラート)アルミニウ
ム、ビス(2−メチル−5−シアノ−8−キノリノラー
ト)アルミニウム−μ−オキソ−ビス(2−メチル−5
−シアノ−8−キノリノラート)アルミニウム、ビス
(2−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−μ−オキソ−ビス(2−メチル
−5−トリフルオロメチル−8−キノリノラート)アル
ミニウムなどを挙げることができる。勿論、発光性有機
金属錯体は、単独で使用してもよく、あるいは複数併用
してもよい。The light-emitting organometallic complex used in combination with the compound A according to the present invention is not particularly limited, but a light-emitting organic aluminum complex is preferable, and a light-emitting having a substituted or unsubstituted 8-quinolinolate ligand. Organic aluminum complexes are more preferred. Preferred luminescent organic metal complexes include, for example, luminescent organic aluminum complexes represented by general formulas (a) to (c). (Q) 3 -Al (a) (wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand) (Q) 2 -Al-OL (b) (wherein Q represents substituted 8 -Represents a quinolinolate ligand, O
-L is a phenolate ligand, and L represents a hydrocarbon group having 6 to 24 carbon atoms including a phenyl moiety.) (Q) 2 -Al-O-Al- (Q) 2 (c) Q represents a substituted 8-quinolinolate ligand) Specific examples of the luminescent organometallic complex include, for example, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5
-Methyl-8-quinolinolate) aluminum, tris (3,4-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate)
Aluminum, tris (4,6-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolinolate) (phenolate) aluminum, bis (2
-Methyl-8-quinolinolate) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (4-methylphenolate) Late) aluminum, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-
Phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,3-dimethylphenolate) aluminum, bis (2- Methyl-8-quinolinolate) (2,6
-Dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3,
5-di-tert-butylphenolato) aluminum, bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6- Triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,5,6-tetra Methyl phenolate)
Aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholate) aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (2 -Phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di-tert-butylphenylphenolate) aluminum , Bis (2-methyl-8-quinolinolate) aluminum Mu-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2
4-dimethyl-8-quinolinolato) aluminum-μ
-Oxo-bis (2,4-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-4-ethyl-8)
-Quinolinolate) aluminum- [mu] -oxo-bis (2-methyl-4-ethyl-8-quinolinolate) aluminum, bis (2-methyl-4-methoxy-8-quinolinolate) aluminum- [mu] -oxo-bis (2-methyl -4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5)
-Cyano-8-quinolinolato) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum, etc. Can be mentioned. Of course, the luminescent organometallic complex may be used alone or in combination.
【0071】電子注入輸送層5は、陰極からの電子の注
入を容易にする機能、そして注入された電子を輸送する
機能を有する化合物を含有する層である。電子注入輸送
層は、本発明に係る化合物Aおよび/または他の電子注
入輸送機能を有する化合物(例えば、有機金属錯体〔例
えば、トリス(8−キノリノラート)アルミニウム、ビ
ス(10−ベンゾ[h]キノリノラート)ベリリウム、5
−ヒドロキシフラボンのベリリウム塩、5−ヒドロキシ
フラボンのアルミニウム塩〕、オキサジアゾール誘導体
〔例えば、1,3−ビス[5’−(p−tert−ブチルフ
ェニル)−1,3,4−オキサジアゾール−2’−イ
ル]ベンゼン〕、トリアゾール誘導体〔例えば、3−
(4’−tert−ブチルフェニル)−4−フェニル−5−
(4”−ビフェニル)−1,2,4−トリアゾール〕、
トリアジン誘導体、ペリレン誘導体、キノリン誘導体、
キノキサリン誘導体、ジフェニルキノン誘導体、ニトロ
置換フルオレノン誘導体、チオピランジオキサイド誘導
体など)を少なくとも一種用いて形成することができ
る。本発明に係る化合物Aと他の電子注入輸送機能を有
する化合物を併用する場合、電子注入輸送層中に占める
本発明に係る化合物Aの割合は、好ましくは、0.1〜
40重量%程度に調製する。本発明において、本発明に
係る化合物Aと有機金属錯体〔例えば、前記一般式
(a)〜一般式(c)で表される化合物〕を併用して、
電子注入輸送層を形成することは好ましい。The electron injecting and transporting layer 5 is a layer containing a compound having a function of facilitating the injection of electrons from the cathode and a function of transporting the injected electrons. The electron injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having an electron injecting and transporting function (eg, an organometallic complex [eg, tris (8-quinolinolate) aluminum, bis (10-benzo [h] quinolinolate) ) Beryllium, 5
Beryllium salt of -hydroxyflavone, aluminum salt of 5-hydroxyflavone], oxadiazole derivative [for example, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-oxadiazole] -2'-yl] benzene], a triazole derivative [eg, 3-
(4′-tert-butylphenyl) -4-phenyl-5-
(4 "-biphenyl) -1,2,4-triazole],
Triazine derivatives, perylene derivatives, quinoline derivatives,
Quinoxaline derivative, diphenylquinone derivative, nitro-substituted fluorenone derivative, thiopyrandioxide derivative, etc.). When the compound A according to the present invention and another compound having an electron injecting and transporting function are used in combination, the proportion of the compound A according to the present invention in the electron injecting and transporting layer is preferably from 0.1 to 0.1.
It is adjusted to about 40% by weight. In the present invention, the compound A according to the present invention and an organometallic complex [for example, the compounds represented by the general formulas (a) to (c)] are used in combination,
It is preferable to form an electron injection transport layer.
【0072】陰極6としては、比較的仕事関数の小さい
金属、合金または電気伝導性化合物を電極物質として使
用することが好ましい。陰極に使用する電極物質として
は、例えば、リチウム、リチウム−インジウム合金、ナ
トリウム、ナトリウム−カリウム合金、カルシウム、マ
グネシウム、マグネシウム−銀合金、マグネシウム−イ
ンジウム合金、インジウム、ルテニウム、チタニウム、
マンガン、イットリウム、アルミニウム、アルミニウム
−リチウム合金、アルミニウム−カルシウム合金、アル
ミニウム−マグネシウム合金、グラファイト薄膜などを
挙げることができる。これらの電極物質は、単独で使用
してもよく、あるいは、複数併用してもよい。陰極は、
これらの電極物質を用いて、例えば、蒸着法、スパッタ
リング法、イオン化蒸着法、イオンプレーティング法、
クラスターイオンビーム法などの方法により、電子注入
輸送層の上に形成することができる。また、陰極は一層
構造であってもよく、あるいは多層構造であってもよ
い。尚、陰極のシート電気抵抗は、数百Ω/□以下に設
定することが好ましい。陰極の厚みは、使用する電極物
質の材料にもよるが、一般に、5〜1000nm程度、
より好ましくは、10〜500nm程度に設定する。
尚、有機電界発光素子の発光を効率よく取り出すため
に、陽極または陰極の少なくとも一方の電極が、透明な
いし半透明であることが好ましく、一般に、発光光の透
過率が70%以上となるように陽極の材料、厚みを設定
することがより好ましい。As the cathode 6, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively small work function as an electrode material. Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium,
Manganese, yttrium, aluminum, an aluminum-lithium alloy, an aluminum-calcium alloy, an aluminum-magnesium alloy, a graphite thin film, and the like can be given. These electrode substances may be used alone or in combination. The cathode is
Using these electrode substances, for example, a vapor deposition method, a sputtering method, an ionization vapor deposition method, an ion plating method,
It can be formed on the electron injection transport layer by a method such as a cluster ion beam method. Further, the cathode may have a single-layer structure or a multilayer structure. Note that the sheet electric resistance of the cathode is preferably set to several hundred Ω / □ or less. The thickness of the cathode depends on the material of the electrode substance used, but is generally about 5 to 1000 nm,
More preferably, it is set to about 10 to 500 nm.
In order to efficiently extract the light emitted from the organic electroluminescent device, it is preferable that at least one of the anode and the cathode is transparent or translucent, and the transmittance of the emitted light is generally 70% or more. It is more preferable to set the material and thickness of the anode.
【0073】また、本発明の有機電界発光素子において
は、その少なくとも一層中に、一重項酸素クエンチャー
が含有されていてもよい。一重項酸素クエンチャーとし
ては、特に限定するものではなく、例えば、ルブレン、
ニッケル錯体、ジフェニルイソベンゾフランなどが挙げ
られ、特に好ましくは、ルブレンである。一重項酸素ク
エンチャーが含有されている層としては、特に限定する
ものではないが、好ましくは、発光層または正孔注入輸
送層であり、より好ましくは、正孔注入輸送層である。
尚、例えば、正孔注入輸送層に一重項クエンチャーを含
有させる場合、正孔注入輸送層中に均一に含有させても
よく、正孔注入輸送層と隣接する層(例えば、発光層、
発光機能を有する電子注入輸送層)の近傍に含有させて
もよい。一重項酸素クエンチャーの含有量としては、含
有される層(例えば、正孔注入輸送層)を構成する全体
量の0.01〜50重量%、好ましくは、0.05〜3
0重量%、より好ましくは、0.1〜20重量%であ
る。Further, in the organic electroluminescent device of the present invention, at least one layer may contain a singlet oxygen quencher. The singlet oxygen quencher is not particularly limited and includes, for example, rubrene,
Nickel complexes, diphenylisobenzofuran and the like can be mentioned, and rubrene is particularly preferable. The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injection transport layer, and more preferably a hole injection transport layer.
For example, when a singlet quencher is contained in the hole injecting and transporting layer, the singlet quencher may be contained uniformly in the hole injecting and transporting layer.
(An electron injection / transport layer having a light emitting function). The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.05 to 3% by weight of the total amount of the contained layer (for example, the hole injection transport layer).
0% by weight, more preferably 0.1 to 20% by weight.
【0074】正孔注入輸送層、発光層、電子注入輸送層
の形成方法に関しては、特に限定するものではなく、例
えば、真空蒸着法、イオン化蒸着法、溶液塗布法(例え
ば、スピンコート法、キャスト法、ディップコート法、
バーコート法、ロールコート法、ラングミュア・ブロゼ
ット法、インクジェット法など)により薄膜を形成する
ことにより作成することができる。真空蒸着法により、
各層を形成する場合、真空蒸着の条件は、特に限定する
ものではないが、10-5Torr程度の真空下で、50〜6
00℃程度のボート温度(蒸着源温度)、−50〜30
0℃程度の基板温度で、0.005〜50nm/sec程
度の蒸着速度で実施することが好ましい。この場合、正
孔注入輸送層、発光層、電子注入輸送層などの各層は、
真空下で、連続して形成することにより、諸特性に一層
優れた有機電界発光素子を製造することができる。真空
蒸着法により、正孔注入輸送層、発光層、電子注入輸送
層などの各層を、複数の化合物を用いて形成する場合、
化合物を入れた各ボートを個別に温度制御して、共蒸着
することが好ましい。The method for forming the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited. For example, a vacuum evaporation method, an ionization evaporation method, a solution coating method (for example, a spin coating method, a casting method, Method, dip coating method,
It can be formed by forming a thin film by a bar coating method, a roll coating method, a Langmuir-Brosette method, an inkjet method, or the like. By vacuum evaporation method,
In the case of forming each layer, the conditions of vacuum deposition are not particularly limited, but under a vacuum of about 10 -5 Torr, 50 to 6
Boat temperature of about 00 ° C (deposition source temperature), -50 to 30
It is preferable to perform the deposition at a substrate temperature of about 0 ° C. and at a deposition rate of about 0.005 to 50 nm / sec. In this case, each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer,
By continuously forming the organic electroluminescent element under vacuum, an organic electroluminescent device having more excellent various characteristics can be manufactured. When each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer is formed using a plurality of compounds by a vacuum evaporation method,
It is preferred that the temperature of each boat containing the compound be individually controlled and co-evaporated.
【0075】溶液塗布法により、各層を形成する場合、
各層を形成する成分あるいはその成分とバインダー樹脂
を、溶媒に溶解、または分散させて塗布液とする。正孔
注入輸送層、発光層、電子注入輸送層の各層に使用しう
るバインダー樹脂としては、例えば、ポリ−N−ビニル
カルバゾール、ポリアリレート、ポリスチレン、ポリエ
ステル、ポリシロキサン、ポリメチルアクリレート、ポ
リメチルメタクリレート、ポリエーテル、ポリカーボネ
ート、ポリアミド、ポリイミド、ポリアミドイミド、ポ
リパラキシレン、ポリエチレン、ポリフェニレンオキサ
イド、ポリエーテルスルフォン、ポリアニリンおよびそ
の誘導体、ポリチオフェンおよびその誘導体、ポリフェ
ニレンビニレンおよびその誘導体、ポリフルオレンおよ
びその誘導体、ポリチエニレンビニレンおよびその誘導
体などの高分子化合物が挙げられる。バインダー樹脂
は、単独で使用してもよく、あるいは、複数併用しても
よい。溶液塗布法により、各層を形成する場合、各層を
形成する成分あるいはその成分とバインダー樹脂を、適
当な有機溶媒(例えば、ヘキサン、オクタン、デカン、
トルエン、キシレン、エチルベンゼン、1−メチルナフ
タレンなどの炭化水素系溶媒、例えば、アセトン、メチ
ルエチルケトン、メチルイソブチルケトン、シクロヘキ
サノンなどのケトン系溶媒、例えば、ジクロロメタン、
クロロホルム、テトラクロロメタン、ジクロロエタン、
トリクロロエタン、テトラクロロエタン、クロロベンゼ
ン、ジクロロベンゼン、クロロトルエンなどのハロゲン
化炭化水素系溶媒、例えば、酢酸エチル、酢酸ブチル、
酢酸アミルなどのエステル系溶媒、例えば、メタノー
ル、プロパノール、ブタノール、ペンタノール、ヘキサ
ノール、シクロヘキサノール、メチルセロソルブ、エチ
ルセロソルブ、エチレングリコールなどのアルコール系
溶媒、例えば、ジブチルエーテル、テトラヒドロフラ
ン、ジオキサン、アニソールなどのエーテル系溶媒、例
えば、N,N−ジメチルホルムアミド、N,N−ジメチ
ルアセトアミド、1−メチル−2−ピロリドン、1−メ
チル−2−イミダゾリジノン、ジメチルスルフォキサイ
ドなどの極性溶媒)および/または水に溶解、または分
散させて塗布液とし、各種の塗布法により、薄膜を形成
することができる。When each layer is formed by a solution coating method,
The components forming each layer or the components and the binder resin are dissolved or dispersed in a solvent to form a coating solution. Examples of the binder resin that can be used for each of the hole injection transport layer, the light emitting layer, and the electron injection transport layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl acrylate, and polymethyl methacrylate. , Polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and its derivatives, polythiophene and its derivatives, polyphenylenevinylene and its derivatives, polyfluorene and its derivatives, polythienyl And high molecular compounds such as lenvinylene and derivatives thereof. The binder resin may be used alone or in combination of two or more. When each layer is formed by a solution coating method, a component forming each layer or the component and a binder resin are mixed with a suitable organic solvent (for example, hexane, octane, decane,
Toluene, xylene, ethylbenzene, hydrocarbon solvents such as 1-methylnaphthalene, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, ketone solvents such as cyclohexanone, for example, dichloromethane,
Chloroform, tetrachloromethane, dichloroethane,
Halogenated hydrocarbon solvents such as trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, for example, ethyl acetate, butyl acetate,
Ester solvents such as amyl acetate, for example, methanol, propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, alcohol solvents such as ethylene glycol, for example, dibutyl ether, tetrahydrofuran, dioxane, anisole and the like Ether solvents such as polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1-methyl-2-imidazolidinone, dimethylsulfoxide) and / or Alternatively, a thin film can be formed by various coating methods by dissolving or dispersing in water to form a coating solution.
【0076】尚、分散する方法としては、特に限定する
ものではないが、例えば、ボールミル、サンドミル、ペ
イントシェーカー、アトライター、ホモジナイザーなど
を用いて微粒子状に分散することができる。塗布液の濃
度に関しては、特に限定するものではなく、実施する塗
布法により、所望の厚みを作成するに適した濃度範囲に
設定することができ、一般には、0.1〜50重量%程
度、好ましくは、1〜30重量%程度の溶液濃度であ
る。尚、バインダー樹脂を使用する場合、その使用量に
関しては、特に制限するものではないが、一般には、各
層を形成する成分に対して(一層型の素子を形成する場
合には、各成分の総量に対して)、5〜99.9重量%
程度、好ましくは、10〜99.9重量%程度、より好
ましくは、15〜90重量%程度に設定する。The method of dispersion is not particularly limited. For example, the particles can be dispersed in fine particles using a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like. The concentration of the coating solution is not particularly limited, and can be set to a concentration range suitable for forming a desired thickness depending on a coating method to be performed, and is generally about 0.1 to 50% by weight. Preferably, the solution concentration is about 1 to 30% by weight. When a binder resin is used, the amount of the binder resin is not particularly limited, but is generally relative to the components forming each layer (when forming a single-layer device, the total amount of each component is 5) to 99.9% by weight
Degree, preferably about 10 to 99.9% by weight, more preferably about 15 to 90% by weight.
【0077】正孔注入輸送層、発光層、電子注入輸送層
の膜厚に関しては、特に限定するものではないが、一般
に、5nm〜5μm程度に設定することが好ましい。
尚、作製した素子に対し、酸素や水分との接触を防止す
る目的で、保護層(封止層)を設けたり、また、素子
を、例えば、パラフィン、流動パラフィン、シリコンオ
イル、フルオロカーボン油、ゼオライト含有フルオロカ
ーボン油などの不活性物質中に封入して保護することが
できる。保護層に使用する材料としては、例えば、有機
高分子材料(例えば、フッ素化樹脂、エポキシ樹脂、シ
リコーン樹脂、エポキシシリコーン樹脂、ポリスチレ
ン、ポリエステル、ポリカーボネート、ポリアミド、ポ
リイミド、ポリアミドイミド、ポリパラキシレン、ポリ
エチレン、ポリフェニレンオキサイド)、無機材料(例
えば、ダイヤモンド薄膜、アモルファスシリカ、電気絶
縁性ガラス、金属酸化物、金属窒化物、金属炭素化物、
金属硫化物)、さらには光硬化性樹脂などを挙げること
ができ、保護層に使用する材料は、単独で使用してもよ
く、あるいは複数併用してもよい。保護層は、一層構造
であってもよく、また多層構造であってもよい。The thicknesses of the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer are not particularly limited, but are generally preferably set to about 5 nm to 5 μm.
A protective layer (sealing layer) may be provided on the manufactured device for the purpose of preventing contact with oxygen or moisture, or the device may be formed of, for example, paraffin, liquid paraffin, silicon oil, fluorocarbon oil, zeolite, or the like. It can be protected by being enclosed in an inert substance such as a contained fluorocarbon oil. Examples of the material used for the protective layer include organic polymer materials (for example, fluorinated resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene) , Polyphenylene oxide), inorganic materials (for example, diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide,
Metal sulfide), and a photocurable resin. The material used for the protective layer may be used alone or in combination of two or more. The protective layer may have a single-layer structure or a multilayer structure.
【0078】また、電極に保護層として、例えば、金属
酸化膜(例えば、酸化アルミニウム膜)、金属フッ化膜
を設けることもできる。また、例えば、陽極の表面に、
例えば、有機リン化合物、ポリシラン、芳香族アミン誘
導体、フタロシアニン誘導体から成る界面層(中間層)
を設けることもできる。さらに、電極、例えば、陽極は
その表面を、例えば、酸、アンモニア/過酸化水素、あ
るいはプラズマで処理して使用することもできる。Further, for example, a metal oxide film (for example, aluminum oxide film) or a metal fluoride film can be provided as a protective layer on the electrode. Also, for example, on the surface of the anode,
For example, an interface layer (intermediate layer) composed of an organic phosphorus compound, polysilane, an aromatic amine derivative, and a phthalocyanine derivative
Can also be provided. Further, electrodes, eg, anodes, can be used by treating the surface with, eg, acid, ammonia / hydrogen peroxide, or plasma.
【0079】本発明の有機電界発光素子は、一般に、直
流駆動型の素子として使用されるが、パルス駆動型また
は交流駆動型の素子としても使用することができる。
尚、印可電圧は、一般に、2〜30V程度である。本発
明の有機電界発光素子は、例えば、パネル型光源、各種
の発光素子、各種の表示素子、各種の標識、各種のセン
サーなどに使用することができる。The organic electroluminescent device of the present invention is generally used as a DC-driven device, but can also be used as a pulse-driven or AC-driven device.
The applied voltage is generally about 2 to 30V. The organic electroluminescent device of the present invention can be used for, for example, a panel light source, various light emitting devices, various display devices, various labels, various sensors, and the like.
【0080】[0080]
【実施例】以下、製造例および実施例により、本発明を
更に詳細に説明するが、勿論、本発明はこれらにより限
定されるものではない。 製造例1 例示化合物A−1の化合物の製造 3−フルオランテニルホウ酸4.92g、1,4−ジブ
ロモナフタレン2.86g、炭酸ナトリウム4.24g
およびテトラキス(トリフェニルフォスフィン)パラジ
ウム0.69gをトルエン(100ml)および水(2
0ml)中で5時間還流した。反応混合物よりトルエン
を留去した後、析出している固体を濾取した。この固体
をアルミナカラムクロマトグラフィー(溶出液:トルエ
ン)で処理した。トルエンを減圧下留去した後、残渣を
トルエンとアセトンの混合溶媒より再結晶し、例示化合
物A−1の化合物を黄色の結晶として3.86g得た。 融点250℃以上 尚、この化合物は、500℃、10-5torrの条件下で昇
華することができた。 吸収極大(トルエン中)368nm 製造例2〜41 製造例1において、3−フルオランテニルホウ酸を使用
する代わりに、種々の3−フルオランテニルホウ酸誘導
体を使用した以外は、製造例1に記載した方法に従い、
種々の1,4−ジ(3’−フルオランテニル)ナフタレ
ン誘導体を製造した。第1表(表1〜表6)には使用し
た3−フルオランテニルホウ酸誘導体、および製造した
1,4−ジ(3’−フルオランテニル)ナフタレン誘導
体を例示化合物番号で示した。また、トルエン中の吸収
極大(nm)も併せて示した。尚、製造された化合物
は、黄色〜橙黄色の結晶であり、その化合物の融点は、
250℃以上であった。EXAMPLES The present invention will be described below in more detail with reference to Production Examples and Examples, but it should be understood that the present invention is not limited by these. Production Example 1 Production of Compound of Exemplified Compound A-1 4.92 g of 3-fluoranthenyl boric acid, 2.86 g of 1,4-dibromonaphthalene, 4.24 g of sodium carbonate
0.69 g of tetrakis (triphenylphosphine) palladium and toluene (100 ml) and water (2
0 ml) for 5 hours. After the toluene was distilled off from the reaction mixture, the precipitated solid was collected by filtration. This solid was treated by alumina column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and acetone to obtain 3.86 g of a compound of Exemplified Compound A-1 as yellow crystals. Melting point: 250 ° C. or higher This compound could be sublimated at 500 ° C. under 10 −5 torr. Absorption maximum (in toluene) 368 nm Production Examples 2-41 Production Example 1 was repeated except that, in Production Example 1, various 3-fluoranthenyl boric acid derivatives were used instead of using 3-fluoranthenyl boric acid derivative. According to the method described,
Various 1,4-di (3'-fluoranthenyl) naphthalene derivatives were produced. In Table 1 (Tables 1 to 6), the used 3-fluoranthenyl boric acid derivatives and the produced 1,4-di (3′-fluoranthenyl) naphthalene derivatives are shown by exemplified compound numbers. The maximum absorption (nm) in toluene is also shown. The produced compound is a yellow to orange-yellow crystal, and the melting point of the compound is
It was 250 ° C or higher.
【0081】[0081]
【表1】 [Table 1]
【0082】[0082]
【表2】 [Table 2]
【0083】[0083]
【表3】 [Table 3]
【0084】[0084]
【表4】 [Table 4]
【0085】[0085]
【表5】 [Table 5]
【0086】[0086]
【表6】 [Table 6]
【0087】実施例1 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’−ビス〔N−フェニ
ル−N−(3”−メチルフェニル)アミノ〕ビフェニル
を蒸着速度0.2nm/secで75nmの厚さに蒸着
し、正孔注入輸送層とした。次いで、その上に、ビス
(2−メチル−8−キノリノラート)(4−フェニルフ
ェノラート)アルミニウムと1,4−ジ(3’−フルオ
ランテニル)ナフタレン(例示化合物番号A−1の化合
物)を、異なる蒸着源から、蒸着速度0.2nm/sec
で50nmの厚さに共蒸着(重量比100:0.5)
し、発光層とした。次に、トリス(8−キノリノラー
ト)アルミニウムを、蒸着速度0.2nm/secで50
nmの厚さに蒸着し、電子注入輸送層とした。さらにそ
の上に、マグネシウムと銀を、蒸着速度0.2nm/se
cで200nmの厚さに共蒸着(重量比10:1)して
陰極とし、有機電界発光素子を作製した。尚、蒸着は、
蒸着槽の減圧状態を保ったまま実施した。作製した有機
電界発光素子に、乾燥雰囲気下、12Vの直流電圧を印
加したところ、55mA/cm2の電流が流れた。輝度2
350cd/m2の青緑色の発光が確認された。Example 1 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2-methyl-8-quinolinolate) (4-phenylphenolato) aluminum and 1,4-di (3′-fluoranthenyl) naphthalene (Exemplary Compound No. A) were formed thereon. -1) from different evaporation sources at an evaporation rate of 0.2 nm / sec.
Co-deposition to a thickness of 50 nm (weight ratio 100: 0.5)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-deposition (weight ratio: 10: 1) was performed to a thickness of 200 nm with c to obtain a cathode, thereby producing an organic electroluminescent device. In addition, evaporation is
The test was performed while maintaining the reduced pressure of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm 2 flowed. Brightness 2
Blue-green light emission of 350 cd / m 2 was confirmed.
【0088】実施例2〜41 実施例1において、発光層の形成に際して、例示化合物
A−1の化合物を使用する代わりに、例示化合物番号A
−3の化合物(実施例2)、例示化合物番号A−4の化
合物(実施例3)、例示化合物番号A−7の化合物(実
施例4)、例示化合物番号A−10の化合物(実施例
5)、例示化合物番号A−17の化合物(実施例6)、
例示化合物番号A−18の化合物(実施例7)、例示化
合物番号A−21の化合物(実施例8)、例示化合物番
号A−22の化合物(実施例9)、例示化合物番号A−
23の化合物(実施例10)、例示化合物番号A−25
の化合物(実施例11)、例示化合物番号A−29の化
合物(実施例12)、例示化合物番号A−33の化合物
(実施例13)、例示化合物番号B−3の化合物(実施
例14)、例示化合物番号B−6の化合物(実施例1
5)、例示化合物番号B−7の化合物(実施例16)、
例示化合物番号B−12の化合物(実施例17)、例示
化合物番号C−1の化合物(実施例18)、例示化合物
番号C−3の化合物(実施例19)、例示化合物番号C
−4の化合物(実施例20)、例示化合物番号C−7の
化合物(実施例21)、例示化合物番号C−11の化合
物(実施例22)、例示化合物番号C−18の化合物
(実施例23)、例示化合物番号C−19の化合物(実
施例24)、例示化合物番号C−23の化合物(実施例
25)、例示化合物番号C−25の化合物(実施例2
6)、例示化合物番号C−28の化合物(実施例2
7)、例示化合物番号C−43の化合物(実施例2
8)、例示化合物番号C−44の化合物(実施例2
9)、例示化合物番号C−47の化合物(実施例3
0)、例示化合物番号C−48の化合物(実施例3
1)、例示化合物番号C−51の化合物(実施例3
2)、例示化合物番号C−52の化合物(実施例3
3)、例示化合物番号C−54の化合物(実施例3
4)、例示化合物番号C−56の化合物(実施例3
5)、例示化合物番号C−59の化合物(実施例3
6)、例示化合物番号C−63の化合物(実施例3
7)、例示化合物番号C−66の化合物(実施例3
8)、例示化合物番号C−70の化合物(実施例3
9)、例示化合物番号C−71の化合物(実施例4
0)、例示化合物番号C−76の化合物(実施例41)
を使用した以外は、実施例1に記載の方法により有機電
界発光素子を作製した。それぞれの素子に、乾燥雰囲気
下、12Vの直流電圧を印加したところ、青緑〜黄緑色
の発光が確認された。さらにその特性を調べ、結果を第
2表(表7〜表8)に示した。Examples 2 to 41 In Example 1, instead of using the compound of Exemplified Compound A-1 in forming the light emitting layer, Exemplified Compound No. A
-3 (Example 2), Exemplified Compound No. A-4 (Example 3), Exemplified Compound No. A-7 (Example 4), Exemplified Compound No. A-10 (Example 5) ), Compound of Exemplified Compound No. A-17 (Example 6),
Compound of Exemplified Compound No. A-18 (Example 7), Compound of Exemplified Compound No. A-21 (Example 8), Compound of Exemplified Compound No. A-22 (Example 9), Exemplified Compound No. A-
Compound No. 23 (Example 10), Exemplified Compound No. A-25
(Example 11), the compound of Exemplified Compound No. A-29 (Example 12), the compound of Exemplified Compound No. A-33 (Example 13), the compound of Exemplified Compound No. B-3 (Example 14), Compound of Exemplified Compound No. B-6 (Example 1
5), Compound of Exemplified Compound No. B-7 (Example 16),
Compound of Exemplified Compound No. B-12 (Example 17), Compound of Exemplified Compound No. C-1 (Example 18), Compound of Exemplified Compound No. C-3 (Example 19), Exemplified Compound No. C
-4 (Example 20), compound of Exemplified Compound No. C-7 (Example 21), compound of Exemplified Compound No. C-11 (Example 22), compound of Exemplified Compound No. C-18 (Example 23) ), Compound of Exemplified Compound No. C-19 (Example 24), compound of Exemplified Compound No. C-23 (Example 25), compound of Exemplified Compound No. C-25 (Example 2)
6), Compound of Exemplified Compound No. C-28 (Example 2)
7), Compound of Exemplified Compound No. C-43 (Example 2)
8), Compound of Exemplified Compound No. C-44 (Example 2)
9), Compound of Exemplified Compound No. C-47 (Example 3)
0), Compound of Exemplified Compound No. C-48 (Example 3)
1), Compound of Exemplified Compound No. C-51 (Example 3)
2), Compound of Exemplified Compound No. C-52 (Example 3)
3), Compound of Exemplified Compound No. C-54 (Example 3)
4), Compound of Exemplified Compound No. C-56 (Example 3)
5), Compound of Exemplified Compound No. C-59 (Example 3)
6), Compound of Exemplified Compound No. C-63 (Example 3)
7), Compound of Exemplified Compound No. C-66 (Example 3)
8), Compound of Exemplified Compound No. C-70 (Example 3)
9), Compound of Exemplified Compound No. C-71 (Example 4)
0), Compound of Exemplified Compound No. C-76 (Example 41)
An organic electroluminescent device was produced by the method described in Example 1 except that was used. When a DC voltage of 12 V was applied to each element under a dry atmosphere, light emission of blue-green to yellow-green was confirmed. The characteristics were further examined, and the results are shown in Table 2 (Tables 7 to 8).
【0089】比較例1 実施例1において、発光層の形成に際して、例示化合物
番号A−1の化合物を使用せずに、ビス(2−メチル−
8−キノリノラート)(4−フェニルフェノラート)ア
ルミニウムだけを用いて、50nmの厚さに蒸着し、発
光層とした以外は、実施例1に記載の方法により有機電
界発光素子を作製した。この素子に、乾燥雰囲気下、1
2Vの直流電圧を印加したところ、青色の発光が確認さ
れた。さらにその特性を調べ、結果を第2表に示した。Comparative Example 1 In Example 1, when forming the light emitting layer, the compound of Exemplified Compound No. A-1 was not used and bis (2-methyl-
An organic electroluminescent device was prepared by the method described in Example 1, except that only 8-quinolinolate) (4-phenylphenolate) aluminum was used to form a light emitting layer by vapor deposition to a thickness of 50 nm. 1
When a DC voltage of 2 V was applied, blue light emission was confirmed. The characteristics were further examined, and the results are shown in Table 2.
【0090】比較例2 実施例1において、発光層の形成に際して、例示化合物
番号A−1の化合物を使用する代わりに、N−メチル−
2−メトキシアクリドンを使用した以外は、実施例1に
記載の方法により有機電界発光素子を作製した。この素
子に、乾燥雰囲気下、12Vの直流電圧を印加したとこ
ろ、青色の発光が確認された。さらにその特性を調べ、
結果を第2表に示した。Comparative Example 2 In Example 1, when forming the light emitting layer, instead of using the compound of Exemplified Compound No. A-1, N-methyl-
An organic electroluminescent device was produced by the method described in Example 1 except that 2-methoxyacridone was used. When a DC voltage of 12 V was applied to this device under a dry atmosphere, blue light emission was confirmed. Further investigate its characteristics,
The results are shown in Table 2.
【0091】[0091]
【表7】 [Table 7]
【0092】[0092]
【表8】 [Table 8]
【0093】実施例42 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’−ビス〔N−フェニ
ル−N−(3”−メチルフェニル)アミノ〕ビフェニル
を蒸着速度0.2nm/secで75nmの厚さに蒸着
し、正孔注入輸送層とした。次いで、その上に、ビス
(2−メチル−8−キノリノラート)(4−フェニルフ
ェノラート)アルミニウムと例示化合物番号A−3の化
合物を、異なる蒸着源から、蒸着速度0.2nm/sec
で50nmの厚さに共蒸着(重量比100:1.0)
し、発光層とした。次に、トリス(8−キノリノラー
ト)アルミニウムを、蒸着速度0.2nm/secで50
nmの厚さに蒸着し、電子注入輸送層とした。さらにそ
の上に、マグネシウムと銀を、蒸着速度0.2nm/se
cで200nmの厚さに共蒸着(重量比10:1)して
陰極とし、有機電界発光素子を作製した。尚、蒸着は、
蒸着槽の減圧状態を保ったまま実施した。作製した有機
電界発光素子に、乾燥雰囲気下、12Vの直流電圧を印
加したところ、58mA/cm2の電流が流れた。輝度2
380cd/m2の青緑色の発光が確認された。Example 42 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2-methyl-8-quinolinolate) (4-phenylphenolato) aluminum and the compound of Exemplified Compound No. A-3 were further deposited thereon from a different evaporation source at a deposition rate of 0. 2nm / sec
Co-deposition to a thickness of 50 nm (weight ratio 100: 1.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-deposition (weight ratio 10: 1) was performed to a thickness of 200 nm by using c to obtain a cathode, thereby producing an organic electroluminescent device. In addition, evaporation is
The test was performed while maintaining the reduced pressure of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 58 mA / cm 2 flowed. Brightness 2
Blue-green light emission of 380 cd / m 2 was confirmed.
【0094】実施例43 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’−ビス〔N−フェニ
ル−N−(3”−メチルフェニル)アミノ〕ビフェニル
を蒸着速度0.2nm/secで75nmの厚さに蒸着
し、正孔注入輸送層とした。次いで、その上に、ビス
(2−メチル−8−キノリノラート)アルミニウム−μ
−オキソ−ビス(2−メチル−8−キノリノラート)ア
ルミニウムと例示化合物番号A−4の化合物を、異なる
蒸着源から、蒸着速度0.2nm/secで50nmの厚
さに共蒸着(重量比100:2.0)し、発光層とし
た。次に、トリス(8−キノリノラート)アルミニウム
を、蒸着速度0.2nm/secで50nmの厚さに蒸着
し、電子注入輸送層とした。さらにその上に、マグネシ
ウムと銀を、蒸着速度0.2nm/secで200nmの
厚さに共蒸着(重量比10:1)して陰極とし、有機電
界発光素子を作製した。尚、蒸着は、蒸着槽の減圧状態
を保ったまま実施した。作製した有機電界発光素子に、
乾燥雰囲気下、12Vの直流電圧を印加したところ、5
7mA/cm2の電流が流れた。輝度2320cd/m2の
青緑色の発光が確認された。Example 43 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, bis (2-methyl-8-quinolinolate) aluminum-μ was formed thereon.
-Oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-4 were co-deposited from different evaporation sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio 100: 2.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. In the manufactured organic electroluminescent element,
When a DC voltage of 12 V was applied in a dry atmosphere,
A current of 7 mA / cm 2 flowed. Blue-green light emission with a luminance of 2320 cd / m 2 was confirmed.
【0095】実施例44 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’−ビス〔N−フェニ
ル−N−(3”−メチルフェニル)アミノ〕ビフェニル
を蒸着速度0.2nm/secで75nmの厚さに蒸着
し、正孔注入輸送層とした。次いで、その上に、ビス
(2,4−ジメチル−8−キノリノラート)アルミニウ
ム−μ−オキソ−ビス(2,4−ジメチル−8−キノリ
ノラート)アルミニウムと例示化合物番号A−7の化合
物を、異なる蒸着源から、蒸着速度0.2nm/secで
50nmの厚さに共蒸着(重量比100:4.0)し、
発光層とした。次に、トリス(8−キノリノラート)ア
ルミニウムを、蒸着速度0.2nm/secで50nmの
厚さに蒸着し、電子注入輸送層とした。さらにその上
に、マグネシウムと銀を、蒸着速度0.2nm/secで
200nmの厚さに共蒸着(重量比10:1)して陰極
とし、有機電界発光素子を作製した。尚、蒸着は、蒸着
槽の減圧状態を保ったまま実施した。作製した有機電界
発光素子に、乾燥雰囲気下、12Vの直流電圧を印加し
たところ、57mA/cm2の電流が流れた。輝度213
0cd/m2の青緑色の発光が確認された。Example 44 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. A-7 were formed thereon. Are co-evaporated (weight ratio 100: 4.0) from different evaporation sources to a thickness of 50 nm at an evaporation rate of 0.2 nm / sec,
It was a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm 2 flowed. Brightness 213
Blue-green light emission of 0 cd / m 2 was confirmed.
【0096】実施例45 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’−ビス〔N−フェニ
ル−N−(3”−メチルフェニル)アミノ〕ビフェニル
を蒸着速度0.2nm/secで75nmの厚さに蒸着
し、正孔注入輸送層とした。次いで、その上に、トリス
(8−キノリノラート)アルミニウムと例示化合物番号
A−10の化合物を、異なる蒸着源から、蒸着速度0.
2nm/secで50nmの厚さに共蒸着(重量比10
0:6.0)し、発光層とした。次に、トリス(8−キ
ノリノラート)アルミニウムを、蒸着速度0.2nm/
secで50nmの厚さに蒸着し、電子注入輸送層とし
た。さらにその上に、マグネシウムと銀を、蒸着速度
0.2nm/secで200nmの厚さに共蒸着(重量比
10:1)して陰極とし、有機電界発光素子を作製し
た。尚、蒸着は、蒸着槽の減圧状態を保ったまま実施し
た。作製した有機電界発光素子に、乾燥雰囲気下、12
Vの直流電圧を印加したところ、58mA/cm2の電流
が流れた。輝度2150cd/m2の青緑色の発光が確
認された。Example 45 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-10 were further deposited thereon from different evaporation sources at a deposition rate of 0.1 mm.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 6.0) to obtain a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm /
Vapor deposition was performed to a thickness of 50 nm in sec to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. The prepared organic electroluminescent device was dried under an atmosphere of 12
When a DC voltage of V was applied, a current of 58 mA / cm 2 flowed. Blue-green light emission with a luminance of 2150 cd / m 2 was confirmed.
【0097】実施例46 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’−ビス〔N−フェニ
ル−N−(3”−メチルフェニル)アミノ〕ビフェニル
を蒸着速度0.2nm/secで75nmの厚さに蒸着
し、正孔注入輸送層とした。次いで、その上に、トリス
(8−キノリノラート)アルミニウムと例示化合物番号
C−47の化合物を、異なる蒸着源から、蒸着速度0.
2nm/secで50nmの厚さに共蒸着(重量比10
0:10)し、発光層とした。次に、トリス(8−キノ
リノラート)アルミニウムを、蒸着速度0.2nm/se
cで50nmの厚さに蒸着し、電子注入輸送層とした。
さらにその上に、マグネシウムと銀を、蒸着速度0.2
nm/secで200nmの厚さに共蒸着(重量比10:
1)して陰極とし、有機電界発光素子を作製した。尚、
蒸着は、蒸着槽の減圧状態を保ったまま実施した。作製
した有機電界発光素子に、乾燥雰囲気下、12Vの直流
電圧を印加したところ、60mA/cm2の電流が流れ
た。輝度2250cd/m2の青緑色の発光が確認され
た。Example 46 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-47 were further deposited thereon from different evaporation sources at a deposition rate of 0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0:10) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / se.
The film was deposited by c to a thickness of 50 nm to form an electron injection transport layer.
Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2.
at 200 nm / sec to a thickness of 200 nm (weight ratio 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 60 mA / cm 2 flowed. Blue-green light emission with a luminance of 2250 cd / m 2 was confirmed.
【0098】実施例47 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’−ビス〔N−フェニ
ル−N−(3”−メチルフェニル)アミノ〕ビフェニル
を蒸着速度0.2nm/secで75nmの厚さに蒸着
し、正孔注入輸送層とした。次いで、その上に、トリス
(8−キノリノラート)アルミニウムと例示化合物番号
C−70の化合物を、異なる蒸着源から、蒸着速度0.
2nm/secで50nmの厚さに共蒸着(重量比10
0:1.0)し、電子注入輸送層を兼ねた発光層とし
た。さらにその上に、マグネシウムと銀を、蒸着速度
0.2nm/secで200nmの厚さに共蒸着(重量比
10:1)して陰極とし、有機電界発光素子を作製し
た。尚、蒸着は、蒸着槽の減圧状態を保ったまま実施し
た。作製した有機電界発光素子に、乾燥雰囲気下、12
Vの直流電圧を印加したところ、58mA/cm2の電流
が流れた。輝度1970cd/m2の青緑色の発光が確
認された。Example 47 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-70 were deposited thereon from different evaporation sources at a deposition rate of 0,0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 1.0) to obtain a light-emitting layer also serving as an electron injection / transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. The prepared organic electroluminescent device was dried under an atmosphere of 12
When a DC voltage of V was applied, a current of 58 mA / cm 2 flowed. Blue-green light emission with a luminance of 1970 cd / m 2 was confirmed.
【0099】実施例48 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’−ビス〔N−フェニ
ル−N−(3”−メチルフェニル)アミノ〕ビフェニル
を蒸着速度0.2nm/secで75nmの厚さに蒸着
し、正孔注入輸送層とした。次いで、その上に、例示化
合物番号C−70の化合物を、蒸着速度0.2nm/se
cで50nmの厚さに蒸着し、発光層とした。次いで、
その上に、1,3−ビス〔5’−(p−tert−ブチルフ
ェニル)−1,3,4−オキサジアゾール−2’−イ
ル〕ベンゼンを、蒸着速度0.2nm/secで50nm
の厚さに蒸着し、電子注入輸送層とした。さらにその上
に、マグネシウムと銀を、蒸着速度0.2nm/secで
200nmの厚さに共蒸着(重量比10:1)して陰極
とし、有機電界発光素子を作製した。尚、蒸着は、蒸着
槽の減圧状態を保ったまま実施した。作製した有機電界
発光素子に、乾燥雰囲気下、14Vの直流電圧を印加し
たところ、41mA/cm2の電流が流れた。輝度185
0cd/m2の青緑色の発光が確認された。Example 48 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, a compound of Exemplified Compound No. C-70 was further deposited thereon with a deposition rate of 0.2 nm / se.
Evaporated to a thickness of 50 nm with c to form a light emitting layer. Then
On top of that, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-oxadiazol-2′-yl] benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm.
To form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 41 mA / cm 2 flowed. Brightness 185
Blue-green light emission of 0 cd / m 2 was confirmed.
【0100】実施例49 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、例示化合物番号A−22の化
合物を蒸着速度0.2nm/secで55nmの厚さに蒸
着し、発光層とした。次いで、その上に、1,3−ビス
〔5’−(p−tert−ブチルフェニル)−1,3,4−
オキサジアゾール−2’−イル〕ベンゼンを、蒸着速度
0.2nm/secで75nmの厚さに蒸着し、電子注入
輸送層とした。さらにその上に、マグネシウムと銀を、
蒸着速度0.2nm/secで200nmの厚さに共蒸着
(重量比10:1)して陰極とし、有機電界発光素子を
作製した。尚、蒸着は、蒸着槽の減圧状態を保ったまま
実施した。作製した有機電界発光素子に、乾燥雰囲気
下、14Vの直流電圧を印加したところ、63mA/cm
2の電流が流れた。輝度1250cd/m2の青緑色の発
光が確認された。Example 49 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, the compound of Exemplified Compound No. A-22 was deposited on the ITO transparent electrode to a thickness of 55 nm at a deposition rate of 0.2 nm / sec to form a light emitting layer. Then, on top of that, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-
[Oxadiazol-2'-yl] benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm to form an electron injecting and transporting layer. On top of that, magnesium and silver,
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 200 nm at an evaporation rate of 0.2 nm / sec to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the produced organic electroluminescent device in a dry atmosphere, the voltage was 63 mA / cm.
Two currents flowed. Blue-green light emission with a luminance of 1250 cd / m 2 was confirmed.
【0101】実施例50 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した後、蒸着装置の基板ホルダー
に固定した後、蒸着槽を3×10-6Torrに減圧した。ま
ず、ITO透明電極上に、4,4’,4”−トリス〔N
−(3'''−メチルフェニル)−N−フェニルアミノ〕ト
リフェニルアミンを蒸着速度0.1nm/secで、50
nmの厚さに蒸着し、第一正孔注入輸送層とした。次い
で、4,4’,−ビス〔N−フェニル−N−(1”−ナ
フチル)アミノ〕ビフェニルと例示化合物番号A−1の
化合物を、異なる蒸着源から、蒸着速度0.2nm/se
cで20nmの厚さに共蒸着(重量比100:5)し、
第二正孔注入輸送層を兼ねた発光層とした。次いで、そ
の上に、トリス(8−キノリノラート)アルミニウム
を、蒸着速度0.2nm/secで50nmの厚さに蒸着
し、電子注入輸送層とした。さらにその上に、マグネシ
ウムと銀を、蒸着速度0.2nm/secで200nmの
厚さに共蒸着(重量比10:1)して陰極とし、有機電
界発光素子を作製した。尚、蒸着は、蒸着槽の減圧状態
を保ったまま実施した。作製した有機電界発光素子に、
乾燥雰囲気下、15Vの直流電圧を印加したところ、6
8mA/cm2の電流が流れた。輝度2650cd/m2の
青緑色の発光が確認された。Example 50 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr. First, 4,4 ′, 4 ″ -tris [N
-(3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine at a deposition rate of 0.1 nm / sec.
The first hole injection transport layer was deposited to a thickness of nm. Next, 4,4 ′,-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl and the compound of Exemplified Compound No. A-1 were deposited from different evaporation sources at an evaporation rate of 0.2 nm / se.
Co-deposited with c to a thickness of 20 nm (weight ratio 100: 5),
The light emitting layer also served as the second hole injection / transport layer. Next, tris (8-quinolinolate) aluminum was deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited thereon at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. In the manufactured organic electroluminescent element,
When a DC voltage of 15 V was applied in a dry atmosphere,
A current of 8 mA / cm 2 flowed. Blue-green light emission with a luminance of 2650 cd / m 2 was confirmed.
【0102】実施例51〜63 実施例50において、例示化合物番号A−1の化合物を
使用する代わりに、例示化合物番号A−2の化合物(実
施例51)、例示化合物番号A−4の化合物(実施例5
2)、例示化合物番号A−17の化合物(実施例5
3)、例示化合物番号A−21の化合物(実施例5
4)、例示化合物番号A−25の化合物(実施例5
5)、例示化合物番号A−29の化合物(実施例5
6)、例示化合物番号B−7の化合物(実施例57)、
例示化合物番号B−12の化合物(実施例58)、例示
化合物番号C−18の化合物(実施例59)、例示化合
物番号C−28の化合物(実施例60)、例示化合物番
号C−44の化合物(実施例61)、例示化合物番号C
−48の化合物(実施例62)、例示化合物番号C−5
9の化合物(実施例63)を使用した以外は、実施例5
0に記載の方法により有機電界発光素子を作製した。そ
れぞれの素子に、乾燥雰囲気下、12Vの直流電圧を印
加したところ、青緑色の発光が確認された。さらにその
特性を調べ、結果を第3表(表9)に示した。Examples 51 to 63 In Example 50, instead of using the compound of Exemplified Compound No. A-1, the compound of Exemplified Compound No. A-2 (Example 51) and the compound of Exemplified Compound No. A-4 (Example Example 5
2), Compound of Exemplified Compound No. A-17 (Example 5)
3), Compound of Exemplified Compound No. A-21 (Example 5)
4), Compound of Exemplified Compound No. A-25 (Example 5)
5), Compound of Exemplified Compound No. A-29 (Example 5)
6), Compound of Exemplified Compound No. B-7 (Example 57),
Compound of Exemplified Compound No. B-12 (Example 58), Compound of Exemplified Compound No. C-18 (Example 59), Compound of Exemplified Compound No. C-28 (Example 60), Compound of Exemplified Compound No. C-44 (Example 61), Exemplified Compound No. C
-48 (Example 62), Exemplified Compound No. C-5
Example 5 except that the compound of Example 9 (Example 63) was used.
An organic electroluminescent device was produced by the method described in No. 0. When a DC voltage of 12 V was applied to each element under a dry atmosphere, blue-green light emission was confirmed. The characteristics were further examined, and the results are shown in Table 3 (Table 9).
【0103】[0103]
【表9】 [Table 9]
【0104】実施例64 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した。次に、ITO透明電極上
に、ポリ−N−ビニルカルバゾール(重量平均分子量1
50000)、1,1,4,4,−テトラフェニル1,
3−ブタジエン(青色の発光成分)、クマリン6〔”3
−(2’−ベンゾチアゾリル)−7−ジエチルアミノク
マリン”(緑色の発光成分)〕、および例示化合物番号
A−10の化合物を、それぞれ重量比100:5:3:
2の割合で含有する3重量%のジクロロエタン溶液を用
いて、ディップコート法により、400nmの発光層を
形成した。次に、この発光層を有するガラス基板を、蒸
着装置の基板ホルダーに固定した後、蒸着槽を3×10
-6Torrに減圧した。さらに、発光層の上に、3−(4’
−tert−ブチルフェニル)−4−フェニル−5−(4”
−ビフェニル)1,2,4−トリアゾールを蒸着速度
0.2nm/secで20nmの厚さに蒸着した後、さら
にその上に、トリス(8−キノリノラート)アルミニウ
ムを、蒸着速度0.2nm/secで30nmの厚さに蒸
着し、電子注入輸送層とした。さらにその上に、マグネ
シウムと銀を、蒸着速度0.2nm/secで200nm
の厚さに共蒸着(重量比10:1)して陰極とし、有機
電界発光素子を作製した。作製した有機電界発光素子
に、乾燥雰囲気下、12Vの直流電圧を印加したとこ
ろ、68mA/cm2の電流が流れた。輝度1140cd
/m2の白色の発光が確認された。Example 64 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, poly-N-vinylcarbazole (weight average molecular weight 1
50000), 1,1,4,4, -tetraphenyl 1,
3-butadiene (blue light-emitting component), coumarin 6 ["3
-(2'-benzothiazolyl) -7-diethylaminocoumarin "(green light-emitting component)] and the compound of Exemplified Compound No. A-10 at a weight ratio of 100: 5: 3:
Using a 3% by weight dichloroethane solution containing 2 parts by weight, a 400 nm light emitting layer was formed by dip coating. Next, after fixing the glass substrate having the light emitting layer to the substrate holder of the vapor deposition apparatus, the vapor deposition tank was set to 3 × 10
The pressure was reduced to -6 Torr. Further, on the light emitting layer, 3- (4 ′
-Tert-butylphenyl) -4-phenyl-5- (4 "
-Biphenyl) 1,2,4-triazole was deposited at a deposition rate of 0.2 nm / sec to a thickness of 20 nm, and then tris (8-quinolinolate) aluminum was further deposited thereon at a deposition rate of 0.2 nm / sec. Evaporation was performed to a thickness of 30 nm to form an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 nm / sec for 200 nm.
And a cathode was formed by co-evaporation (weight ratio: 10: 1) to obtain an organic electroluminescent device. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 68 mA / cm 2 flowed. Brightness 1140cd
/ M 2 was confirmed.
【0105】実施例65〜70 実施例64において、例示化合物番号A−10の化合物
を用いる代わりに、例示化合物番号A−18の化合物
(実施例65)、例示化合物番号A−29の化合物(実
施例66)、例示化合物番号C−4の化合物(実施例6
7)、例示化合物番号C−23の化合物(実施例6
8)、例示化合物番号C−28の化合物(実施例6
9)、例示化合物番号C−54の化合物(実施例70)
を使用した以外は、実施例64に記載の方法により有機
電界発光素子を作製した。それぞれの素子に、乾燥雰囲
気下、12Vの直流電圧を印加したところ、白色の発光
が観察された。さらにその特性を調べ、結果を第4表
(表10)に示した。Examples 65 to 70 In Example 64, instead of using the compound of Exemplified Compound No. A-10, the compound of Exemplified Compound No. A-18 (Example 65) and the compound of Exemplified Compound No. A-29 (Example Example 66), Compound of Exemplified Compound No. C-4 (Example 6)
7), Compound of Exemplified Compound No. C-23 (Example 6)
8), Compound of Exemplified Compound No. C-28 (Example 6)
9), Compound of Exemplified Compound No. C-54 (Example 70)
An organic electroluminescent device was produced by the method described in Example 64 except that was used. When a DC voltage of 12 V was applied to each device under a dry atmosphere, white light emission was observed. The characteristics were further examined, and the results are shown in Table 4 (Table 10).
【0106】[0106]
【表10】 [Table 10]
【0107】実施例71 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した。次に、ITO透明電極上
に、ポリ−N−ビニルカルバゾール(重量平均分子量1
50000)、1,3−ビス〔5’−(p−tert−ブチ
ルフェニル)−1,3,4−オキサジアゾール−2’−
イル〕ベンゼンおよび例示化合物番号A−3の化合物
を、それぞれ重量比100:30:3の割合で含有する
3重量%のジクロロエタン溶液を用いて、ディップコー
ト法により、300nmの発光層を形成した。次に、こ
の発光層を有するガラス基板を、蒸着装置の基板ホルダ
ーに固定した後、蒸着槽を3×10-6Torrに減圧した。
さらに、発光層の上に、マグネシウムと銀を、蒸着速度
0.2nm/secで200nmの厚さに共蒸着(重量比
10:1)して陰極とし、有機電界発光素子を作製し
た。作製した有機電界発光素子に、乾燥雰囲気下、15
Vの直流電圧を印加したところ、74mA/cm2の電流
が流れた。輝度1420cd/m2の青緑色の発光が確
認された。Example 71 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, poly-N-vinylcarbazole (weight average molecular weight 1
50000), 1,3-bis [5 '-(p-tert-butylphenyl) -1,3,4-oxadiazole-2'-
[Il] benzene and a compound of Exemplified Compound No. A-3 were formed by dip coating using a 3 wt% dichloroethane solution containing 100: 30: 3 by weight to form a 300 nm light emitting layer. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device, the pressure in the vapor deposition tank was reduced to 3 × 10 −6 Torr.
Further, on the light emitting layer, magnesium and silver were co-deposited (weight ratio: 10: 1) at a deposition rate of 0.2 nm / sec to a thickness of 200 nm to form an organic electroluminescent device. The prepared organic electroluminescent device was dried under a dry atmosphere for 15 minutes.
When a DC voltage of V was applied, a current of 74 mA / cm 2 flowed. Blue-green light emission with a luminance of 1420 cd / m 2 was confirmed.
【0108】比較例3 実施例71において、発光層の形成に際して、例示化合
物番号A−3の化合物の代わりに、1,1,4,4−テ
トラフェニル−1,3−ブタジエンを使用した以外は、
実施例67に記載の方法により有機電界発光素子を作製
した。作製した有機電界発光素子に、乾燥雰囲気下、1
5Vの直流電圧を印加したところ、86mA/cm2の電
流が流れた。輝度750cd/m2の青色の発光が確認
された。Comparative Example 3 In Example 71, 1,1,4,4-tetraphenyl-1,3-butadiene was used instead of the compound of Exemplified Compound No. A-3 in forming the light emitting layer. ,
An organic electroluminescent device was produced by the method described in Example 67. In a dry atmosphere, add 1
When a DC voltage of 5 V was applied, a current of 86 mA / cm 2 flowed. Blue light emission with a luminance of 750 cd / m 2 was confirmed.
【0109】実施例72 厚さ200nmのITO透明電極(陽極)を有するガラ
ス基板を、中性洗剤、アセトン、エタノールを用いて超
音波洗浄した。その基板を窒素ガスを用いて乾燥し、さ
らにUV/オゾン洗浄した。次に、ITO透明電極上
に、ポリカーボネート(重量平均分子量50000)、
4,4’−ビス〔N−フェニル−N−(3”−メチルフ
ェニル)アミノ〕ビフェニル、ビス(2−メチル−8−
キノリノラート)アルミニウム−μ−オキソ−ビス(2
−メチル−8−キノリノラート)アルミニウムおよび例
示化合物番号C−18の化合物を、それぞれ重量比10
0:40:60:1の割合で含有する3重量%のジクロ
ロエタン溶液を用いて、ディップコート法により、30
0nmの発光層を形成した。次に、この発光層を有する
ガラス基板を、蒸着装置の基板ホルダーに固定した後、
蒸着槽を3×10-6Torrに減圧した。さらに、発光層の
上に、マグネシウムと銀を、蒸着速度0.2nm/sec
で200nmの厚さに共蒸着(重量比10:1)して陰
極とし、有機電界発光素子を作製した。作製した有機電
界発光素子に、乾燥雰囲気下、15Vの直流電圧を印加
したところ、65mA/cm2の電流が流れた。輝度89
0cd/m2の青緑色の発光が確認された。Example 72 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, polycarbonate (weight average molecular weight: 50,000),
4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, bis (2-methyl-8-
Quinolinolate) aluminum-μ-oxo-bis (2
-Methyl-8-quinolinolate) aluminum and the compound of Exemplified Compound No. C-18 were each added at a weight ratio of 10
Using a 3% by weight dichloroethane solution containing 0: 40: 60: 1 at a ratio of 30% by a dip coating method.
A 0 nm light emitting layer was formed. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device,
The pressure in the evaporation tank was reduced to 3 × 10 −6 Torr. Further, on the light emitting layer, magnesium and silver were deposited at a deposition rate of 0.2 nm / sec.
Then, co-evaporation (weight ratio: 10: 1) was performed to a thickness of 200 nm to form a cathode, thereby producing an organic electroluminescent device. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 65 mA / cm 2 flowed. Brightness 89
Blue-green light emission of 0 cd / m 2 was confirmed.
【0110】[0110]
【発明の効果】本発明により、発光輝度が優れた有機電
界発光素子を提供することが可能になった。さらに、該
発光素子に適した炭化水素化合物を提供することが可能
になった。According to the present invention, it has become possible to provide an organic electroluminescent device having excellent light emission luminance. Further, it has become possible to provide a hydrocarbon compound suitable for the light-emitting element.
【図1】有機電界発光素子の一例の概略構造図である。FIG. 1 is a schematic structural diagram of an example of an organic electroluminescent device.
【図2】有機電界発光素子の一例の概略構造図である。FIG. 2 is a schematic structural diagram of an example of an organic electroluminescent device.
【図3】有機電界発光素子の一例の概略構造図である。FIG. 3 is a schematic structural diagram of an example of an organic electroluminescent device.
【図4】有機電界発光素子の一例の概略構造図である。FIG. 4 is a schematic structural diagram of an example of an organic electroluminescent device.
【図5】有機電界発光素子の一例の概略構造図である。FIG. 5 is a schematic structural diagram of an example of an organic electroluminescent device.
【図6】有機電界発光素子の一例の概略構造図である。FIG. 6 is a schematic structural diagram of an example of an organic electroluminescent device.
【図7】有機電界発光素子の一例の概略構造図である。FIG. 7 is a schematic structural diagram of an example of an organic electroluminescent device.
【図8】有機電界発光素子の一例の概略構造図である。FIG. 8 is a schematic structural diagram of an example of an organic electroluminescent device.
1 :基板 2 :陽極 3 :正孔注入輸送層 3a:正孔注入輸送成分 4 :発光層 4a:発光成分 5 :電子注入輸送層 5’:電子注入輸送層 5a:電子注入輸送成分 6 :陰極 7 :電源 1: substrate 2: anode 3: hole injection / transport layer 3a: hole injection / transport component 4: light emitting layer 4a: light emitting component 5: electron injection / transport layer 5 ': electron injection / transport layer 5a: electron injection / transport component 6: cathode 7: Power supply
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 FI テーマコート゛(参考) C09K 11/06 610 C09K 11/06 610 H05B 33/22 H05B 33/22 B D Fターム(参考) 3K007 AB02 AB03 AB04 AB11 CA01 CB01 DA01 DB03 EB00 4H006 AA01 AB92 EA37 GP03 GP30──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) C09K 11/06 610 C09K 11/06 610 H05B 33/22 H05B 33/22 BD DF term (Reference) 3K007 AB02 AB03 AB04 AB11 CA01 CB01 DA01 DB03 EB00 4H006 AA01 AB92 EA37 GP03 GP30
Claims (8)
ルオランテニル)ナフタレン誘導体を少なくとも一種含
有する層を、少なくとも一層挟持してなる有機電界発光
素子。1. An organic electroluminescent device comprising at least one layer containing at least one 1,4-di (3′-fluoranthenyl) naphthalene derivative sandwiched between a pair of electrodes.
ナフタレン誘導体を含有する層が、発光層である請求項
1記載の有機電界発光素子。2. 1,4-di (3′-fluoranthenyl)
The organic electroluminescent device according to claim 1, wherein the layer containing the naphthalene derivative is a light emitting layer.
ナフタレン誘導体を含有する層が、さらに、発光性有機
金属錯体を含有することを特徴とする請求項1または2
記載の有機電界発光素子。3. A 1,4-di (3′-fluoranthenyl)
3. The layer containing a naphthalene derivative further contains a luminescent organometallic complex.
The organic electroluminescent device according to claim 1.
ナフタレン誘導体を含有する層が、さらに、トリアリー
ルアミン誘導体を含有することを特徴とする請求項1ま
たは2記載の有機電界発光素子。4. A 1,4-di (3′-fluoranthenyl)
3. The organic electroluminescent device according to claim 1, wherein the layer containing a naphthalene derivative further contains a triarylamine derivative.
層を有する請求項1〜4のいずれかに記載の有機電界発
光素子。5. The organic electroluminescent device according to claim 1, further comprising a hole injection transport layer between the pair of electrodes.
層を有する請求項1〜5のいずれかに記載の有機電界発
光素子。6. The organic electroluminescent device according to claim 1, further comprising an electron injection / transport layer between the pair of electrodes.
ナフタレン誘導体が、一般式(1−A)(化1)で表さ
れる化合物である請求項1〜6のいずれかに記載の有機
電界発光素子。 【化1】 (式中、X1〜X24はそれぞれ独立に、水素原子、ハロ
ゲン原子、直鎖、分岐または環状のアルキル基、直鎖、
分岐または環状のアルコキシ基、あるいは置換または未
置換のアリール基を表す。)7. A 1,4-di (3′-fluoranthenyl)
The organic electroluminescent device according to claim 1, wherein the naphthalene derivative is a compound represented by the general formula (1-A) (Formula 1). Embedded image (Wherein X 1 to X 24 each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. )
合物。 【化2】 (式中、X1〜X24はそれぞれ独立に、水素原子、ハロ
ゲン原子、直鎖、分岐または環状のアルキル基、直鎖、
分岐または環状のアルコキシ基、あるいは置換または未
置換のアリール基を表す。)8. A compound represented by the general formula (1-A): Embedded image (Wherein X 1 to X 24 each independently represent a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a straight-chain,
Represents a branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. )
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US8039129B2 (en) | 2009-04-06 | 2011-10-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
US8039127B2 (en) | 2009-04-06 | 2011-10-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
WO2015182547A1 (en) * | 2014-05-28 | 2015-12-03 | 東レ株式会社 | Fluoranthene derivative, electronic device containing same, light-emitting element, and photoelectric conversion element |
JPWO2015182547A1 (en) * | 2014-05-28 | 2017-04-20 | 東レ株式会社 | Fluoranthene derivative, electronic device containing the same, light emitting element and photoelectric conversion element |
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