JP2008120696A - Novel tripyridylphenyl derivative, electron transport material comprising the same, and organic electroluminescence device including the same - Google Patents
Novel tripyridylphenyl derivative, electron transport material comprising the same, and organic electroluminescence device including the same Download PDFInfo
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- JP2008120696A JP2008120696A JP2006303131A JP2006303131A JP2008120696A JP 2008120696 A JP2008120696 A JP 2008120696A JP 2006303131 A JP2006303131 A JP 2006303131A JP 2006303131 A JP2006303131 A JP 2006303131A JP 2008120696 A JP2008120696 A JP 2008120696A
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- organic electroluminescence
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- 239000000463 material Substances 0.000 title claims abstract description 66
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 abstract description 12
- 239000010410 layer Substances 0.000 description 142
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- 238000002347 injection Methods 0.000 description 40
- 239000007924 injection Substances 0.000 description 40
- 230000005525 hole transport Effects 0.000 description 38
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 30
- 230000000052 comparative effect Effects 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- 238000000034 method Methods 0.000 description 15
- NSABRUJKERBGOU-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 NSABRUJKERBGOU-UHFFFAOYSA-N 0.000 description 14
- 0 CC1(C=NC(c2cncnc2)=CC1)c1cc(C(C=N)=CC=*C(C=N)=CN=C)cc(-c(cc2)cnc2C(C=NC=[N+])=C)c1 Chemical compound CC1(C=NC(c2cncnc2)=CC1)c1cc(C(C=N)=CC=*C(C=N)=CN=C)cc(-c(cc2)cnc2C(C=NC=[N+])=C)c1 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- -1 4,6-difluorophenyl Chemical group 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000005281 excited state Effects 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007772 electrode material Substances 0.000 description 6
- 238000001194 electroluminescence spectrum Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000000103 photoluminescence spectrum Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- XAGZJIQIVXSURR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical group C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCCC1 XAGZJIQIVXSURR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- ZRXVCYGHAUGABY-UHFFFAOYSA-O tris(4-bromophenyl)azanium Chemical compound C1=CC(Br)=CC=C1[NH+](C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 ZRXVCYGHAUGABY-UHFFFAOYSA-O 0.000 description 2
- CHBDXRNMDNRJJC-UHFFFAOYSA-N 1,2,3-triphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CHBDXRNMDNRJJC-UHFFFAOYSA-N 0.000 description 1
- LTSSSVHTLGQZAQ-UHFFFAOYSA-N 1,3,5-tribromo-2,4,6-trimethylbenzene Chemical group CC1=C(Br)C(C)=C(Br)C(C)=C1Br LTSSSVHTLGQZAQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- JPDUPGAVXNALOL-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetraphenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 JPDUPGAVXNALOL-UHFFFAOYSA-N 0.000 description 1
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NCRIDSGPLISUEU-UHFFFAOYSA-N 2-bromo-6-pyridin-2-ylpyridine Chemical group BrC1=CC=CC(C=2N=CC=CC=2)=N1 NCRIDSGPLISUEU-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NNNYHNUZYYNHCS-UHFFFAOYSA-N 3-bromo-5-pyridin-3-ylpyridine Chemical group BrC1=CN=CC(C=2C=NC=CC=2)=C1 NNNYHNUZYYNHCS-UHFFFAOYSA-N 0.000 description 1
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 1
- ZNJRONVKWRHYBF-VOTSOKGWSA-N 4-(dicyanomethylene)-2-methyl-6-julolidyl-9-enyl-4h-pyran Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-VOTSOKGWSA-N 0.000 description 1
- ILJRIAPZWHYPMK-UHFFFAOYSA-N 5-bromo-2-pyridin-3-ylpyridine Chemical compound N1=CC(Br)=CC=C1C1=CC=CN=C1 ILJRIAPZWHYPMK-UHFFFAOYSA-N 0.000 description 1
- QKWORTBZGYIMOM-UHFFFAOYSA-N 9-(2-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 QKWORTBZGYIMOM-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 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
- 150000003518 tetracenes Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
【課題】新規なトリピリジルフェニル誘導体、それよりなる電子輸送材料およびそれを含む有機エレクトロルミネッセンス素子の提供。
【解決手段】
下記一般式（１）
【化１】
（式中、Ｑは、
【化２】
よりなる群から選ばれた基であり、Ｒ１〜Ｒ１０は、水素および炭素数１〜６の直鎖または分岐のアルキル基よりなる群からそれぞれ独立して選ばれた基である。）
で示されるトリピリジルフェニル誘導体、それよりなる電子輸送材料およびそれを含む有機エレクトロルミネッセンス素子。
【選択図】なしThe present invention provides a novel tripyridylphenyl derivative, an electron transport material comprising the derivative, and an organic electroluminescence device including the material.
[Solution]
The following general formula (1)
[Chemical 1]
(Where Q is
[Chemical 2]
R 1 to R 10 are groups independently selected from the group consisting of hydrogen and a linear or branched alkyl group having 1 to 6 carbon atoms. )
A tripyridylphenyl derivative, an electron transport material comprising the same, and an organic electroluminescence device comprising the same.
[Selection figure] None
Description
本発明は、新規なトリピリジルフェニル誘導体、それよりなる電子輸送材料およびそれを含む有機エレクトロルミネッセンス素子に関する。 The present invention relates to a novel tripyridylphenyl derivative, an electron transport material comprising the same, and an organic electroluminescence device including the same.
有機エレクトロルミネッセンス素子（有機ＥＬ素子）は、電極から注入されたホールと電極の再結合によって生成した励起エネルギーが発光過程を経て基底状態に緩和されることにより自発光する。しかしながら、ホールと電子の再結合によって生成する励起状態には一重項励起状態と三重項励起状態の２種類がそれぞれ１対３の割合で存在する。これまでの多くは一重項励起状態からの発光を利用した蛍光材料が発光材料に利用されていたため、内部量子効率が最大で２５％であるので、この時取り出し効率を２０％とすると、最大外部量子効率は５％が理論限界であった。 An organic electroluminescence element (organic EL element) emits light by itself, when excitation energy generated by recombination of holes injected from an electrode and the electrode is relaxed to a ground state through a light emission process. However, there are two types of excited states generated by recombination of holes and electrons, a singlet excited state and a triplet excited state, in a ratio of 1: 3. In many cases, a fluorescent material utilizing light emission from a singlet excited state has been used as a light emitting material, and therefore, the internal quantum efficiency is 25% at the maximum. The quantum efficiency was the theoretical limit of 5%.
近年、イリジウムやプラチナなどの重原子効果を利用した錯体化合物を用い三重項励起状態からの発光、すなわちリン光発光を用いることにより発光効率の向上が報告されるようになった（例えば、非特許文献１）。一重項励起状態に加え、三重項励起状態からの発光を利用することで最大内部量子効率は理論上１００％に到達することが可能で、リン光材料は発光材料として注目を浴びている（非特許文献３）。 In recent years, improvement in luminous efficiency has been reported by using light emission from a triplet excited state, that is, phosphorescence emission, using a complex compound utilizing a heavy atom effect such as iridium or platinum (for example, non-patented) Reference 1). The maximum internal quantum efficiency can theoretically reach 100% by utilizing light emission from the triplet excited state in addition to the singlet excited state, and phosphorescent materials are attracting attention as light emitting materials (non Patent Document 3).
例えば緑色材料として、下記式
また安達らによる非特許文献２などにより青色発光材料である下記式
その結果最近ではＳ．Ｒ．Ｆｏｒｒｅｓｔらによる非特許文献１では下記式
これら発光材料を効率よく発光させるにはホールと電子の注入バランスを整えて、発光層の中で十分にこれらのキャリアーの結合が行えるようにホール輸送剤や電子輸送剤などを選択しなければならない。
特に青色リン光材料についてはエネルギーギャップが大きいためにワイドギャップ化されたホール輸送剤や電子輸送剤が必要になってくる。現在これらリン光材料については、電子輸送材料に従来から使用されているＡｌｑ３〔トリス（８−ヒドロキシキノリノラト）アルミニウム〕やＢＡｌｑ２〔ビス（２−メチル−８−キノリノラト）アルミニウムｐ−フェニルフェノラート〕等が使用されているが、リン光材料に使用するには十分なエネルギーギャップを持ち合わせていないため新規なワイドギャップな電子輸送材料の開発が必要である。
In particular, since the blue phosphorescent material has a large energy gap, a hole transport agent and an electron transport agent having a wide gap are required. As for these phosphorescent materials, Alq 3 [tris (8-hydroxyquinolinolato) aluminum] and BAlq 2 [bis (2-methyl-8-quinolinolato) aluminum p-phenyl conventionally used for electron transport materials are used. Phenolate] and the like are used, but a new wide-gap electron transport material needs to be developed because it does not have a sufficient energy gap for use in phosphorescent materials.
本発明の目的は、新規なトリピリジルフェニル誘導体、それよりなる電子輸送材料およびそれを含む有機エレクトロルミネッセンス素子を提供する点にある。 An object of the present invention is to provide a novel tripyridylphenyl derivative, an electron transport material comprising the same, and an organic electroluminescence device including the same.
本発明の第１は、下記一般式（１）
で示されるトリピリジルフェニル誘導体に関する。
本発明の第２は、請求項１記載のトリピリジルフェニル誘導体よりなる電子輸送材料に関する。
本発明の第３は、請求項１記載のトリピリジルフェニル誘導体を含有する有機エレクトロルミネッセンス素子に関する。
The first of the present invention is the following general formula (1)
It is related with the tripyridylphenyl derivative shown by these.
The second of the present invention relates to an electron transport material comprising the tripyridylphenyl derivative according to
3rd of this invention is related with the organic electroluminescent element containing the tripyridylphenyl derivative of
本発明のトリピリジルフェニル誘導体は、下記の反応により製造することができる。
本発明におけるＲ１〜Ｒ１０における炭素数１〜６の直鎖または分岐のアルキル基としては、メチル、エチル、プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｔ−ブチル、ヘプチル、イソヘプチル、ｎ−ヘキシル等を挙げることができる。 Examples of the linear or branched alkyl group having 1 to 6 carbon atoms in R 1 to R 10 in the present invention include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, heptyl, isoheptyl, and n-hexyl. Etc.
以下に本発明の化合物の具体例を示す。
Specific examples of the compound of the present invention are shown below.
本発明のトリピリジルフェニル誘導体は高い電子輸送性能を有する。従って、電子注入材料及び電子輸送材料として使用することができる。 The tripyridylphenyl derivative of the present invention has high electron transport performance. Therefore, it can be used as an electron injection material and an electron transport material.
本発明のトリピリジルフェニル誘導体を有機エレクトロルミネッセンス素子に使用する場合、適当な発光材料（ドーパント）と組み合わせて使用することもできる。 When the tripyridylphenyl derivative of the present invention is used in an organic electroluminescence device, it can also be used in combination with a suitable light emitting material (dopant).
本発明のトリピリジルフェニル誘導体を電子輸送層に用いる場合、本発明の化合物は電子注入材料や電子輸送材料として使用できる。また他の電子輸送材料と組み合わせて使用することもできる。 When the tripyridylphenyl derivative of the present invention is used for an electron transport layer, the compound of the present invention can be used as an electron injection material or an electron transport material. It can also be used in combination with other electron transport materials.
次に本発明の有機エレクトロルミネッセンス素子について説明する。本発明の有機エレクトロルミネッセンス素子は、陽極と陰極間に一層もしくは多層の有機化合物を積層した素子であり、該有機化合物層の少なくとも一層が本発明のトリピリジルフェニル誘導体を含有する。有機エレクトロルミネッセンス素子が一層の場合、陽極と陰極間に発光層を設けている。発光層は、発光材料を含有しそれに加えて陽極から注入した正孔もしくは陰極から注入した電子を発光材料まで輸送するのが目的で、正孔注入材料もしくは電子注入材料を含有していても良い。多層型の有機エレクトロルミネッセンス素子の構成例としては、例えばＩＴＯ／ホール輸送層／発光層／電子輸送層／陰極、ＩＴＯ／ホール注入層／ホール輸送層／発光層／電子輸送層／陰極、ＩＴＯ／ホール輸送層／発光層／電子輸送層／電子注入層／陰極、ＩＴＯ／ホール輸送層／発光層／ホールブロック層／電子輸送層／陰極、ＩＴＯ／ホール注入層／ホール輸送層／発光層／ホールブロック層／電子輸送層／陰極、ＩＴＯ／ホール輸送層／発光層／ホールブロック層／電子輸送層／電子注入層／陰極、ＩＴＯ／ホール注入層／ホール輸送層／発光層／ホールブロック層／電子輸送層／電子注入層／陰極等の多層構成で積層されたものがあげられる。また、必要に応じて陰極上に封止層を有していても良い。 Next, the organic electroluminescence element of the present invention will be described. The organic electroluminescence device of the present invention is a device in which a single layer or a multilayer organic compound is laminated between an anode and a cathode, and at least one layer of the organic compound layer contains the tripyridylphenyl derivative of the present invention. When the organic electroluminescence element is a single layer, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material and may contain a hole injecting material or an electron injecting material for the purpose of transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. . Examples of the configuration of the multi-layer organic electroluminescence element include, for example, ITO / hole transport layer / light-emitting layer / electron transport layer / cathode, ITO / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode, ITO / Hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode, ITO / hole transport layer / light emitting layer / hole block layer / electron transport layer / cathode, ITO / hole injection layer / hole transport layer / light emitting layer / hole Block layer / electron transport layer / cathode, ITO / hole transport layer / light emitting layer / hole block layer / electron transport layer / electron injection layer / cathode, ITO / hole injection layer / hole transport layer / light emitting layer / hole block layer / electron Examples thereof include those laminated in a multilayer structure such as a transport layer / electron injection layer / cathode. Moreover, you may have a sealing layer on a cathode as needed.
正孔輸送層、電子輸送層、および発光層のそれぞれの層は、一層構造であっても、多層構造であっても良い。また正孔輸送層、電子輸送層はそれぞれの層で注入機能を受け持つ層（正孔注入層及び電子注入層）と輸送機能を受け持つ層（正孔輸送層および電子輸送層）を別々に設けることもできる。 Each of the hole transport layer, the electron transport layer, and the light emitting layer may have a single layer structure or a multilayer structure. In addition, the hole transport layer and the electron transport layer should be provided separately with a layer responsible for the injection function (hole injection layer and electron injection layer) and a layer responsible for the transport function (hole transport layer and electron transport layer). You can also.
本発明の有機エレクトロルミネッセンス素子は、上記構成例に限らず、種々の構成とすることができる。必要に応じて、正孔輸送層成分と発光層成分、あるいは電子輸送層成分と発光層成分を混合した層を設けても良い。 The organic electroluminescence element of the present invention is not limited to the above configuration example, and can have various configurations. If necessary, a layer in which a hole transport layer component and a light emitting layer component or an electron transport layer component and a light emitting layer component are mixed may be provided.
以下本発明の有機エレクトロルミネッセンス素子の構成要素に関して、陽極／正孔輸送層／発光層／電子輸送層／陰極からなる素子構成を例として取り上げて詳細に説明する。本発明の有機エレクトロルミネッセンス素子は、基板に支持されていることが好ましい。 Hereinafter, the constituent elements of the organic electroluminescence element of the present invention will be described in detail by taking as an example an element structure comprising an anode / hole transport layer / light emitting layer / electron transport layer / cathode. The organic electroluminescence device of the present invention is preferably supported on a substrate.
基板の素材については特に制限はなく、従来の有機エレクトロルミネッセンス素子に慣用されているものであれば良く、例えばガラス、石英ガラス、透明プラスチックなどからなるものを用いることができる。 There is no restriction | limiting in particular about the raw material of a board | substrate, What is necessary is just used for the conventional organic electroluminescent element, For example, what consists of glass, quartz glass, a transparent plastic etc. can be used.
本発明の有機エレクトロルミネッセンス素子の陽極としては、仕事関数の大きな金属単体（４ｅＶ以上）、仕事関数の大きな金属同士の合金（４ｅＶ以上）または導電性物質およびこれらの混合物を電極材料とすることが好ましい。このような電極材料の具体例としては、金、銀、銅等の金属、ＩＴＯ（インジウム−スズオキサイド）、酸化スズ（ＳｎＯ２）、酸化亜鉛（ＺｎＯ）などの導電性透明材料、ポリピロール、ポリチオフェン等の導電性高分子材料が挙げられる。陽極はこれらの電極材料を、例えば蒸着、スパッタリング、塗布などの方法により基板上に形成することができる。陽極のシート電気抵抗は数百Ω／ｃｍ２以下が好ましい。陽極の膜厚は材料にもよるが、一般に５〜１，０００ｎｍ程度、好ましくは１０〜５００ｎｍである。 As an anode of the organic electroluminescence device of the present invention, an electrode material may be a single metal having a high work function (4 eV or more), an alloy of metals having a high work function (4 eV or more), a conductive substance, or a mixture thereof. preferable. Specific examples of such electrode materials include metals such as gold, silver, and copper, conductive transparent materials such as ITO (indium-tin oxide), tin oxide (SnO 2 ), and zinc oxide (ZnO), polypyrrole, and polythiophene. Examples thereof include conductive polymer materials such as For the anode, these electrode materials can be formed on the substrate by a method such as vapor deposition, sputtering, or coating. The sheet electrical resistance of the anode is preferably several hundred Ω / cm 2 or less. The thickness of the anode depends on the material, but is generally about 5 to 1,000 nm, preferably 10 to 500 nm.
陰極としては、仕事関数の小さな金属単体（４ｅＶ以下）、仕事関数の小さな金属同士の合金（４ｅＶ以下）または導電性物質およびこれらの混合物を電極材料とすることが好ましい。このような電極材料の具体例としては、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、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、アルミニウム、アルミニウム−リチウム合金、アルミニウム−マグネシウム合金などが挙げられる。陰極はこれらの電極材料を、例えば蒸着、スパッタリングなどの方法により、薄膜を形成させることにより作製することができる。陰極のシート電気抵抗は数百Ω／ｃｍ２以下が好ましい。陰極の膜厚は材料にもよるが、一般に５〜１，０００ｎｍ程度、好ましくは１０〜５００ｎｍである。本発明の有機エレクトロルミネッセンス素子の発光を効率良く取り出すために、陽極または陰極の少なくとも一方の電極は、透明もしくは半透明であることが好ましい。 As the cathode, an electrode material is preferably a single metal having a small work function (4 eV or less), an alloy of metals having a small work function (4 eV or less), a conductive substance, or a mixture thereof. Specific examples of such electrode materials include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, magnesium, magnesium-silver alloy, magnesium-indium alloy, aluminum, aluminum-lithium alloy, and aluminum-magnesium alloy. Can be mentioned. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet electrical resistance of the cathode is preferably several hundred Ω / cm 2 or less. The thickness of the cathode depends on the material, but is generally about 5 to 1,000 nm, preferably 10 to 500 nm. In order to efficiently extract light emitted from the organic electroluminescence device of the present invention, at least one of the anode and the cathode is preferably transparent or translucent.
本発明の有機エレクトロルミネッセンス素子の正孔輸送層は、正孔伝達化合物からなるもので、陽極より注入された正孔を発光層に伝達する機能を有している。電界が与えた２つの電極間に正孔伝達化合物が配置されて陽極から正孔が注入された場合、少なくとも１０−６ｃｍ２／Ｖ・秒以上の正孔移動度を有する正孔伝達物質が好ましい。本発明の有機エレクトロルミネッセンス素子に使用する正孔輸送層に使用する正孔伝達物質は、前記の好ましい性質を有するものであれば特に制限はない。従来から光導電材料において正孔の電荷注入輸送材料として慣用されているものや有機エレクトロルミネッセンス素子の正孔輸送層に使用されている公知の材料の中から任意のものを選択して用いることができる。 The hole transport layer of the organic electroluminescence device of the present invention is made of a hole transfer compound and has a function of transferring holes injected from the anode to the light emitting layer. When a hole transport compound is disposed between two electrodes to which an electric field is applied and holes are injected from the anode, a hole transport material having a hole mobility of at least 10 −6 cm 2 / V · second or more is obtained. preferable. The hole transport material used for the hole transport layer used in the organic electroluminescence device of the present invention is not particularly limited as long as it has the above-mentioned preferable properties. It is possible to select and use any of the materials conventionally used as hole charge injection / transport materials in photoconductive materials and known materials used for the hole transport layer of organic electroluminescent devices. it can.
前記の正孔伝達物質としては、例えば銅フタロシアニンなどのフタロシアニン誘導体、Ｎ，Ｎ，Ｎ′，Ｎ′−テトラフェニル−１，４−フェニレンジアミン、Ｎ，Ｎ′−ジ（ｍ−トリル）−Ｎ，Ｎ′−ジフェニル−４，４′−ジアミノビフェニル（ＴＰＤ）、Ｎ，Ｎ′−ジ（１−ナフチル）−Ｎ，Ｎ′−ジフェニル−４，４′−ジアミノビフェニル（α−ＮＰＤ）、等のトリアリールアミン誘導体、ポリフェニレンジアミン誘導体、ポリチオフェン誘導体、および水溶性のＰＥＤＯＴ−ＰＳＳ（ポリエチレンジオキサチオフェン−ポリスチレンスルホン酸）が挙げられる。正孔輸送層は、これらの他の正孔伝達化合物一種または二種以上からなる一層で構成されたもので良く、前記の正孔伝達物質とは別の化合物からなる正孔輸送層を積層したものでもよい。
正孔注入材料としては、下記化学式に示すＰＥＤＯＴ：ＰＳＳ（ポリマー混合物）やＤＮＴＰＤを挙げることができる。
Examples of the hole injection material include PEDOT: PSS (polymer mixture) and DNTPD represented by the following chemical formula.
本発明の有機エレクトロルミネッセンス素子の発光層の発光物質については特に制限されることはなく、従来の公知の化合物の中から任意のものを選択して用いることができる。 The light emitting material of the light emitting layer of the organic electroluminescence device of the present invention is not particularly limited, and any one of conventionally known compounds can be selected and used.
発光材料としては、ペリレン誘導体、ナフタセン誘導体、キナクリドン誘導体、クマリン誘導体（例えばクマリン１、クマリン５４０、クマリン５４５など）、ピラン誘導体（例えばＤＣＭ−１、ＤＣＭ−２、ＤＣＪＴＢなど）、有機金属錯体、例えばトリス（８−ヒドロキシキノリノラト）アルミニウム（Ａｌｑ３）、トリス（４−メチル−８−ヒドロキシキノリノラト）アルミニウム（Ａｌｍｑ３）等の蛍光材料やビス［２−（４，６−ジフルオロフェニル）ピリジネート−Ｎ，Ｃ′］イリジウム（III）ピコリレート（ＦＩｒｐｉｃ）、トリス｛１−［４−（トリフルオロメチル）フェニル］−１Ｈ−ピラゾラート，Ｎ，Ｃ２′｝イリジウム（III）（Ｉｒｔｆｍｐｐｚ３）、ビス［２−（４′，６′−ジフルオロフェニル）ピリジネート−Ｎ，Ｃ２′］テトラキス（１−ピラゾリル）ボレート（Ｆｉｒ６）、トリス（２−フェニルピリジナト）イリジウム（III）［Ｉｒ（ＰＰｙ）３］などのリン光材料などを挙げることができる。
Examples of the light-emitting material include perylene derivatives, naphthacene derivatives, quinacridone derivatives, coumarin derivatives (eg,
発光層は、ホスト材料とゲスト材料（ドーパント）から形成することもできる［Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．，６５ ３６１０（１９８９）］。特にリン光材料を発光層に使用する場合、ホスト材料の使用が必要でありこの時使用されるホスト材料としては４，４′−ジ（Ｎ−カルバゾリル）−１，１′−ビフェニル（ＣＢＰ）、１，４−ジ（Ｎ−カルバゾリル）ベンゼン、２，２′−ジ〔４″−（Ｎ−カルバゾリル）フェニル〕−１，１′−ビフェニル（４ＣｚＰＢＰ）等があげられる。 The light-emitting layer can also be formed of a host material and a guest material (dopant) [Appl. Phys. Lett. 65 3610 (1989)]. In particular, when a phosphorescent material is used for the light emitting layer, it is necessary to use a host material, and the host material used at this time is 4,4'-di (N-carbazolyl) -1,1'-biphenyl (CBP). 1,2-di (N-carbazolyl) benzene, 2,2′-di [4 ″-(N-carbazolyl) phenyl] -1,1′-biphenyl (4CzPBP) and the like.
ゲスト材料は、ホスト材料に対して、好ましくは０．０１〜４０重量％であり、より好ましくは０．１〜２０重量％である。ゲスト材料としては、従来公知のＦＩｒｐｉｃ（化４）、Ｉｒ（ＰＰｙ）３（化３）、Ｆｉｒ６（化６）などを挙げることができる。 The guest material is preferably 0.01 to 40% by weight, more preferably 0.1 to 20% by weight, based on the host material. Examples of guest materials include conventionally known FIrpic (Chemical Formula 4), Ir (PPy) 3 (Chemical Formula 3), and Fir6 (Chemical Formula 6).
本発明の有機エレクトロルミネッセンス素子の電子輸送層の材料としては、本発明のトリピリジルフェニル誘導体が好ましい。このものは単独で使用できるが他の電子輸送材料と併用しても構わない。 As a material for the electron transport layer of the organic electroluminescence device of the present invention, the tripyridylphenyl derivative of the present invention is preferable. Although this thing can be used independently, you may use together with another electron transport material.
本発明の有機エレクトロルミネッセンス素子は、電子注入性をさらに向上させる目的で、陰極と有機層の間に絶縁体で構成される電子注入層をさらに設けても良い。ここで使用される導電体としては、アルカリ金属ハロゲン化物、アルカリ土類金属ハロゲン化物から選択される少なくとも一つの金属化合物を使用することが好ましい。アルカリ金属ハロゲン化物としては、フッ化リチウム、フッ化ナトリウム、フッ化カリウム、フッ化セシウム、塩化リチウム等が挙げられる。アルカリ土類金属ハロゲン化物としては、フッ化マグネシウム、フッ化カルシウム、フッ化バリウム、フッ化ストロンチウム等が挙げられる。 The organic electroluminescent device of the present invention may further include an electron injection layer composed of an insulator between the cathode and the organic layer for the purpose of further improving the electron injection property. As the conductor used here, it is preferable to use at least one metal compound selected from alkali metal halides and alkaline earth metal halides. Examples of the alkali metal halide include lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, and lithium chloride. Examples of the alkaline earth metal halide include magnesium fluoride, calcium fluoride, barium fluoride, and strontium fluoride.
正孔輸送層、発光層の形成方法については特に限定されるものではない。例えば乾式成膜法（例えば真空蒸着法、イオン化蒸着法など）、湿式成膜法〔溶液塗布法（例えば、スピンコート法、キャスト法、インクジェット法など）〕を使用することができる。本発明のトリピリジルフェニル誘導体の電子輸送層の形成方法については、乾式成膜法（例えば真空蒸着法、イオン化蒸着法）が好ましい。また素子の作製については上記の成膜方法を併用しても構わない。 The method for forming the hole transport layer and the light emitting layer is not particularly limited. For example, a dry film forming method (for example, a vacuum deposition method, an ionization vapor deposition method, etc.) or a wet film forming method [a solution coating method (for example, a spin coating method, a casting method, an ink jet method, etc.)] can be used. As the method for forming the electron transport layer of the tripyridylphenyl derivative of the present invention, a dry film formation method (for example, a vacuum evaporation method or an ionization evaporation method) is preferable. In addition, the above-described film formation method may be used in combination for manufacturing the element.
真空蒸着法により正孔輸送層、発光層、電子輸送層等の各層を形成する場合、真空蒸着条件は、特に限定されるものではない。通常１０−４Ｐａ程度以下の真空下で５０〜５００℃程度のボート温度（蒸着源温度）、−５０〜３００℃程度の基板温度で、０．０１〜５０ｎｍ／ｓｅｃ．程度蒸着することが好ましい。正孔輸送層、発光層、電子輸送層の各層を複数の化合物を使用して形成する場合、化合物を入れた各ボートをそれぞれ温度制御しながら共蒸着することが好ましい。 When forming each layer such as a hole transport layer, a light emitting layer, and an electron transport layer by a vacuum deposition method, the vacuum deposition conditions are not particularly limited. Usually, a boat temperature (deposition source temperature) of about 50 to 500 ° C. under a vacuum of about 10 −4 Pa or less, a substrate temperature of about −50 to 300 ° C., and 0.01 to 50 nm / sec. Vapor deposition is preferred. When forming each layer of a positive hole transport layer, a light emitting layer, and an electron carrying layer using a some compound, it is preferable to co-evaporate each boat which put the compound, temperature-controlling each.
正孔輸送層、発光層を溶媒塗布法で形成する場合、各層を構成する成分を溶媒に溶解または分散させて塗布液とする。溶媒としては、炭化水素系溶媒（例えば、ヘプタン、トルエン、キシレン、シクロヘキサン等）、ケトン系溶媒（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等）、ハロゲン系溶媒（例えばジクロロメタン、クロロホルム、クロロベンゼン、ジクロロベンゼン等）、エステル系溶媒（例えば酢酸エチル、酢酸ブチル等）、アルコール系溶媒（例えばメタノール、エタノール、ブタノール、メチルセロソルブ、エチルセロソルブ等）、エーテル系溶媒（例えばジブチルエーテル、テトラヒドロフラン、１，４−ジオキサン、１，２−ジメトキシエタン等）、非プロトン性溶媒（例えばＮ，Ｎ′−ジメチルアセトアミド、ジメチルスルホキシド等）、水等が挙げられる。溶媒は単独で使用しても良く、複数の溶媒を併用しても良い。 When forming the hole transport layer and the light emitting layer by a solvent coating method, the components constituting each layer are dissolved or dispersed in a solvent to obtain a coating solution. Solvents include hydrocarbon solvents (eg, heptane, toluene, xylene, cyclohexane, etc.), ketone solvents (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), halogen solvents (eg, dichloromethane, chloroform, chlorobenzene, dichlorobenzene, etc.) ), Ester solvents (eg, ethyl acetate, butyl acetate, etc.), alcohol solvents (eg, methanol, ethanol, butanol, methyl cellosolve, ethyl cellosolve, etc.), ether solvents (eg, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like), aprotic solvents (for example, N, N'-dimethylacetamide, dimethyl sulfoxide and the like), water and the like. The solvent may be used alone, or a plurality of solvents may be used in combination.
正孔輸送層、発光層、電子輸送層等の各層の膜厚は、特に限定されるものではないが、通常５〜５，０００ｎｍになるようにする。 The thickness of each layer such as the hole transport layer, the light emitting layer, and the electron transport layer is not particularly limited, but is usually 5 to 5,000 nm.
本発明の有機エレクトロルミネッセンス素子は、酸素や水分等との接触を遮断する目的で保護層（封止層）を設けたり、不活性物質中に素子を封入して保護することができる。不活性物質としては、パラフィン、シリコンオイル、フルオロカーボン等が挙げられる。保護層に使用する材料としては、フッ素樹脂、エポキシ樹脂、シリコーン樹脂、ポリエステル、ポリカーボネート、光硬化性樹脂等が挙げられる。 The organic electroluminescence device of the present invention can be protected by providing a protective layer (sealing layer) for the purpose of blocking contact with oxygen, moisture, or the like, or by encapsulating the device in an inert substance. Examples of the inert substance include paraffin, silicon oil, and fluorocarbon. Examples of the material used for the protective layer include fluorine resin, epoxy resin, silicone resin, polyester, polycarbonate, and photocurable resin.
本発明の有機エレクトロルミネッセンス素子は、通常直流駆動の素子として使用できる。直流電圧を印加する場合、陽極をプラス、陰極をマイナスの極性として電圧を通常１．５〜２０Ｖ程度印加すると発光が観測される。また、本発明の有機エレクトロルミネッセンス素子は交流駆動の素子としても使用できる。交流電圧を印加する場合には、陽極がプラス、陰極がマイナスの状態になった時に発光する。本発明の有機エレクトロルミネッセンス素子は、例えば電子写真感光体、フラットパネルディスプレイなどの平面発光体、複写機、プリンター、液晶ディスプレイのバックライト、計器等の光源、各種発光素子、各種表示素子、各種標識、各種センサー、各種アクセサリーなどに使用することができる。 The organic electroluminescence device of the present invention can be used as a normal DC drive device. When a DC voltage is applied, light emission is observed when a voltage of about 1.5 to 20 V is applied with the positive polarity of the anode and the negative polarity of the cathode. Moreover, the organic electroluminescent element of this invention can be used also as an element of an alternating current drive. When an AC voltage is applied, light is emitted when the anode is in a positive state and the cathode is in a negative state. The organic electroluminescent device of the present invention is, for example, a flat light emitter such as an electrophotographic photosensitive member or a flat panel display, a copying machine, a printer, a backlight of a liquid crystal display, a light source such as an instrument, various light emitting devices, various display devices, various signs. It can be used for various sensors and various accessories.
図３５〜４８に、本発明の有機エレクトロルミネッセンス素子の好ましい例を示す。 The preferable example of the organic electroluminescent element of this invention is shown in FIGS.
図３５は、本発明の有機エレクトロルミネッセンス素子の一例を示す断面図である。図３５は、基板１上に陽極２、発光層３および陰極４を順次設けた構成のものである。ここで使用する発光素子は、それ自体が正孔輸送性、電子輸送性及び発光性の機能を単一で有している場合や、それぞれの機能を有する化合物を混合して使用する場合に有用である。
FIG. 35 is a cross-sectional view showing an example of the organic electroluminescence element of the present invention. FIG. 35 shows a structure in which an
図３６は、本発明の有機エレクトロルミネッセンス素子における他の例を示す断面図である。図３６は、基板１上に、陽極２、正孔輸送層５、発光層３及び陰極４を順次設けた構成のものである。この場合、発光層は電子輸送性の機能を有している場合に有用である。
FIG. 36 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 36 shows a configuration in which an
図３７は、本発明の有機エレクトロルミネッセンス素子における他の例を示す断面図である。図３７は、基板１上に、陽極２、発光層３、電子輸送層６及び陰極４を順次設けた構成のものである。この場合、発光層は正孔輸送性の機能を有している場合に有用である。
FIG. 37 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 37 shows a structure in which an
図３８は、本発明の有機エレクトロルミネッセンス素子における他の例を示す断面図である。図３８は、基板１上に、陽極２、正孔輸送層５、発光層３、電子輸送層６及び陰極４を順次設けた構成のものである。これは、キャリア輸送と発光の機能を分離したものであり、材料選択の自由度が増すために、発光の高効率化や発光色の自由度が増すことになる。
FIG. 38 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 38 shows a configuration in which an
図３９は、本発明の有機エレクトロルミネッセンス素子における他の例を示す断面図である。図３９は、基板１上に、陽極２、正孔注入層７、正孔輸送層５、発光層３、電子輸送層６及び陰極４を順次設けた構成のものである。この場合、正孔注入層７を設けることにより、陽極２と正孔輸送層５の密着性を高めたり、陽極から正孔の注入を良くし、発光素子の低電圧駆動に効果がある。
FIG. 39 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 39 shows a structure in which an
図４０は、本発明の有機エレクトロルミネッセンス素子における他の例を示す断面図である。図４０は、基板１上に、陽極２、正孔輸送層５、発光層３、電子輸送層６、電子注入層８及び陰極４を順次設けた構成のものである。この場合、陰極４から電子の注入を良くし、発光素子の低電圧駆動に効果がある。
FIG. 40 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 40 shows a configuration in which an
図４１は、本発明の有機エレクトロルミネッセンス素子における他の例を示す断面図である。図４１は、基板１上に、陽極２、正孔注入層７、正孔輸送層５、発光層３、電子輸送層６、電子注入層８及び陰極４を順次設けた構成のものである。この場合、陽極２から正孔の注入を良くし、陰極４からは電子の注入を良くし、最も低電圧駆動に効果がある構成である。
FIG. 41 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 41 shows a configuration in which an
図４２〜４８は、素子の中に正孔ブロック層を挿入したものの断面図である。正孔ブロック層は、陽極から注入された正孔、あるいは発光層３で再結合により生成した励起子が陰極４に抜けることを防止する効果があり、エレクトロルミネッセンス素子の発光効率の向上に効果がある。正孔ブロック層９については、発光層３と陰極４の間もしくは発光層３と電子輸送層６の間あるいは発光層３と電子注入層８の間に挿入することができる。より好ましいものは発光層３と電子輸送層６の間である。
42 to 48 are cross-sectional views of the device in which a hole blocking layer is inserted. The hole blocking layer has an effect of preventing holes injected from the anode or excitons generated by recombination in the
図４２〜４８で、正孔輸送層５、正孔注入層７、電子輸送層６、電子注入層８、発光層３、正孔ブロック層９のそれぞれの層は、一層構造であっても、多層構造であってもよい。
42 to 48, each of the
図３５〜４８は、あくまで基本的な素子構成であり、本発明の化合物を用いた有機エレクトロルミネッセンス素子の構成は、これに限定されるものではない。 35 to 48 are basic device configurations to the last, and the configuration of the organic electroluminescence device using the compound of the present invention is not limited to this.
前記電子注入層に用いる電子注入材料としては、本出願人の特願２００６−２９２０３２号にかかる化合物、例えば下記化合物群を例示することができる。
本発明のトリピリジルフェニル誘導体は、電子親和力の値が２．８〜３．０と大きく電子の閉じこめ効果が大きい。またエネルギーギャップの値が３．４〜４．１と大きな値をとるため、大きなエネルギーを必要とする青色発光材料の電子輸送材料に適している。本発明化合物の励起スペクトルを測定すると青色の領域になる。しかし、実施例で緑色に光っているのは、発光材料に緑色のリン光材料であるＩｒ（ｐｐｙ）３を使用しているからである。 The tripyridylphenyl derivative of the present invention has a large electron affinity value of 2.8 to 3.0 and a large electron confinement effect. Moreover, since the value of the energy gap is as large as 3.4 to 4.1, it is suitable for an electron transport material of a blue light emitting material that requires large energy. When the excitation spectrum of the compound of the present invention is measured, it becomes a blue region. However, the reason why it glows green in the example is that Ir (ppy) 3 that is a green phosphorescent material is used as the light emitting material.
以下に実施例を挙げて本発明を説明するが、本発明はこれにより何ら限定されるものではない。 Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited thereto.
実施例１
トリス−１，３，５−〔６′−（ピリジン−３″−イル）ピリジン−３′−イル〕ベンゼン｛Ｔｒｉｓ−１，３，５−〔６′−（ｐｙｒｉｄｉｎｅ−３″−ｙｌ）ｐｙｒｉｄｉｎｅ−３′−ｙｌ〕ｂｅｎｚｅｎｅ｝（Ｔｐ３３ＢＰＹＢ）の合成
このもののＵＶスペクトルおよびＰＬスペクトルは図１および図２に示す。
Example 1
Tris-1,3,5- [6 ′-(pyridin-3 ″ -yl) pyridin-3′-yl] benzene {Tris-1,3,5- [6 ′-(pyridine-3 ″ -yl) pyridine −3′-yl] benzene} (Tp33BPYB)
The UV spectrum and PL spectrum of this product are shown in FIGS.
実施例２
トリス−１，３，５−〔６′−（ピリジン−３″−イル）ピリジン−３′−イル〕−２，４，６−トリメチルベンゼン｛Ｔｒｉｓ−１，３，５−〔６′−（ｐｙｒｉｄｉｎｅ−３″−ｙｌ）ｐｙｒｉｄｉｎｅ−３′−ｙｌ〕−２，４，６−ｔｒｉｍｅｔｈｙｌｂｅｎｚｅｎｅ｝（Ｔｐ３３ＢＰＹＭＥＳ）の合成
このもののＵＶスペクトルおよびＰＬスペクトルは図１および図２に示す。
Example 2
Tris-1,3,5- [6 ′-(pyridin-3 ″ -yl) pyridin-3′-yl] -2,4,6-trimethylbenzene {Tris-1,3,5- [6 ′-( pyridine-3 "-yl) pyridine-3'-yl] -2,4,6-trimethylbenzene} (Tp33BPYMES)
The UV spectrum and PL spectrum of this product are shown in FIGS.
実施例３
トリス−１，３，５−〔５′−（ピリジン−３″−イル）ピリジン−３′−イル〕ベンゼン｛Ｔｒｉｓ−１，３，５−〔５′−（ｐｙｒｉｄｉｎｅ−３″−ｙｌ）ｐｙｒｉｄｉｎｅ−３′−ｙｌ〕ｂｅｎｚｅｎｅ｝（Ｔｍ３３ＢＰｙＢ）の合成
精製はカラムクロマトグラフィー法（展開溶媒：クロロホルム／メタノール＝２０／１）を行い、白い粉末を得た。収率：５６．７ｍｏｌ％。
構造確認は１Ｈ−ＮＭＲで行った。
このもののＵＶスペクトルおよびＰＬスペクトルは図１および図２に示す。
Example 3
Tris-1,3,5- [5 ′-(pyridin-3 ″ -yl) pyridin-3′-yl] benzene {Tris-1,3,5- [5 ′-(pyridine-3 ″ -yl) pyridine −3′-yl] benzene} (Tm33BPyB)
Purification was performed by column chromatography (developing solvent: chloroform / methanol = 20/1) to obtain a white powder. Yield: 56.7 mol%.
The structure was confirmed by 1 H-NMR.
The UV spectrum and PL spectrum of this product are shown in FIGS.
実施例１〜３で得られたそれぞれの化合物の電気化学特性は下記表のとおりである。
Ｅｇ＝１２４０÷Ｗ
例えば接線を引いて求めた値Ｗ（ｎｍ）が４７０ｎｍだったとしたらこの時のＥｇの値は
Ｅｇ＝１２４０÷４７０＝２．６３（ｅＶ）
と言うことになる。
Ｉｐ（イオン化ポテンシャル）は、イオン化ポテンシャル測定装置（例えば理研計器ＡＣ−１）を使用して測定し、測定するサンプルがイオン化を開始しだしたところの電圧（ｅＶ）の値を読む。
Ｅａ（電子親和力）は、ＩｐからＥｇを引いた値である。
本明細書における波長に対する強度（ｉｎｔｅｎｓｉｔｙ ａ．ｕ．）の測定は、浜松ホトニクス社製ストリークカメラを用いて、クライオスタット中で４．２Ｋにおいて測定した。
ＩＰ＝ＨＯＭＯ，Ｅａ＝ＬＵＭＯ
図１、２にそれぞれの蒸着膜のＵＶ吸収、ＰＬスペクトルを示した。表１には電気化学特性を示した。ＵＶ吸収スペクトルやＰＬスペクトルからもわかるように吸収端、発光ピークはいずれもＴｐ３３ＢＰＹＢ、Ｔｐ３３ＢＰＹＭＥＳ、Ｔｍ３３ＢＰＹＢの順にブルーシフトすることがわかる。この結果より共役系を最も制御できているのがメタ結合で結合したＴｍ３３ＢＰＹＢであるということができる。ＩｐはＴｐ３３ＢＰＹＭＥＳ、Ｔｍ３３ＢＰＹＢともに６．６ｅＶ以上と高いものであり、これら２つの化合物はホールブロック性が高い。
The electrochemical characteristics of the respective compounds obtained in Examples 1 to 3 are as shown in the following table.
Eg = 1240 ÷ W
For example, if the value W (nm) obtained by drawing a tangent is 470 nm, the value of Eg at this time is Eg = 1240 ÷ 470 = 2.63 (eV)
It will be said.
Ip (ionization potential) is measured using an ionization potential measuring apparatus (for example, Riken Keiki AC-1), and the value of the voltage (eV) at which the sample to be measured starts ionization is read.
Ea (electron affinity) is a value obtained by subtracting Eg from Ip.
Intensity au in this specification was measured at 4.2K in a cryostat using a streak camera manufactured by Hamamatsu Photonics.
IP = HOMO, Ea = LUMO
1 and 2 show the UV absorption and PL spectrum of each deposited film. Table 1 shows the electrochemical characteristics. As can be seen from the UV absorption spectrum and PL spectrum, the absorption edge and emission peak are all blue shifted in the order of Tp33BPYB, Tp33BPYMES, and Tm33BPYB. From this result, it can be said that Tm33BPYB bonded by a meta bond has the most control over the conjugated system. Ip is as high as 6.6 eV or more for both Tp33BPYMES and Tm33BPYB, and these two compounds have high hole blocking properties.
実施例４
トリス−１，３，５−〔６′−（ピリジン−３″−イル）ピリジン−２′−イル〕ベンゼン｛Ｔｒｉｓ−１，３，５−〔６′−（ｐｙｒｉｄｉｎｅ−３″−ｙｌ）ｐｙｒｉｄｉｎｅ−２′−ｙｌ〕ｂｅｎｚｅｎｅ｝（Ｔｍ２３ＢＰｙＢ）の合成
精製はカラムクロマトグラフィー法（展開溶媒：クロロホルム／メタノール＝３０／１）を行い、白い粉末を得た。収率：７４．６ｍｏｌ％。
構造確認は１Ｈ−ＮＭＲで行った。
Example 4
Tris-1,3,5- [6 ′-(pyridin-3 ″ -yl) pyridin-2′-yl] benzene {Tris-1,3,5- [6 ′-(pyridine-3 ″ -yl) pyridine -2'-yl] benzene} (Tm23BPyB)
Purification was performed by column chromatography (developing solvent: chloroform / methanol = 30/1) to obtain a white powder. Yield: 74.6 mol%.
The structure was confirmed by 1 H-NMR.
実施例５
トリス−１，３，５−〔６′−（ピリジン−２″−イル）ピリジン−２′−イル〕ベンゼン｛Ｔｒｉｓ−１，３，５−〔６′−（ｐｙｒｉｄｉｎｅ−２″−ｙｌ）ｐｙｒｉｄｉｎｅ−２′−ｙｌ〕ｂｅｎｚｅｎｅ｝（Ｔｍ２２ＢＰｙＢ）の合成
精製はカラムクロマトグラフィー法（展開溶媒：クロロホルム／酢酸エチル＝２／１）を行い、白い粉末を得た。収率：（２．２０ｇ），９０．４ｍｏｌ％。
構造確認は１Ｈ−ＮＭＲおよびＭＡＳＳで行った。
Example 5
Tris-1,3,5- [6 ′-(pyridin-2 ″ -yl) pyridin-2′-yl] benzene {Tris-1,3,5- [6 ′-(pyridine-2 ″ -yl) pyridine -2'-yl] benzene} (Tm22BPyB)
Purification was performed by column chromatography (developing solvent: chloroform / ethyl acetate = 2/1) to obtain a white powder. Yield: (2.20 g), 90.4 mol%.
The structure was confirmed by 1 H-NMR and MASS.
比較例１
下記化学構造式
ＴｍＰｙＰｈＢ、Ｔｍ２３ＢＰｙＢおよびＴｍ３３ＢＰｙＢの各蒸着膜の吸収スペクトルおよび蛍光スペクトルは、図３および４に示し、その電気化学的特性は下記表に示す。
Ｔｍ３３ＢＰｙＢの光学的エネルギーギャップ（Ｅｇ）は、吸収スペクトルの吸収端より３．８６ｅＶと見積もった。Ｔｍ２３ＢＰｙＢは長波長に吸収ピークが現れたため、吸収端より見積もった光学的エネルギーギャップ（Ｅｇ）は狭くなり、３．５８ｅＶである。大気中光電子分析装置（ＡＣ−３）の測定結果より、Ｔｍ３３ＢＰｙＢのＨＯＭＯ値は６．６８ｅＶであり、Ｅｇとの差より、ＬＵＭＯの値は２．８２ｅＶと見積もった。Ｔｍ２３ＢＰｙＢのＨＯＭＯ値は６．６６ｅＶであり、ＬＵＭＯの値は３．０８ｅＶであ５る。Ｔｍ２３ＢＰｙＢのＬＵＭＯレベルは低いため、電子注入障壁は低いと予測され、電子輸送材料として有機ＥＬ素子への応用が期待される。
Comparative Example 1
The following chemical structural formula
The absorption spectrum and fluorescence spectrum of each deposited film of TmPyPhB, Tm23BPyB, and Tm33BPyB are shown in FIGS. 3 and 4, and the electrochemical characteristics thereof are shown in the following table.
The optical energy gap (Eg) of Tm33BPyB was estimated to be 3.86 eV from the absorption edge of the absorption spectrum. Since Tm23BPyB has an absorption peak at a long wavelength, the optical energy gap (Eg) estimated from the absorption edge is narrowed to 3.58 eV. From the measurement results of the atmospheric photoelectron analyzer (AC-3), the HOMO value of Tm33BPyB was 6.68 eV, and the LUMO value was estimated to be 2.82 eV from the difference from Eg. The HOMO value of Tm23BPyB is 6.66 eV, and the LUMO value is 3.08 eV. Since the LUMO level of Tm23BPyB is low, the electron injection barrier is expected to be low, and application to an organic EL device is expected as an electron transport material.
実施例６、７、比較例２
実施例２で得られたＴｐ３３ＢＰＹＭＥＳ
実施例３で得られたＴｍ３３ＢＰｙＢ
をそれぞれ電子輸送材料として用いた有機ＥＬ素子をつくり、電子輸送材料として代表的なＡｌｑ３のみを用いた有機ＥＬ素子（比較例２）と対比した。
有機ＥＬ素子の構成
比較例２：ＩＴＯ／α−ＮＰＤ（５０ｎｍ）／Ａｌｑ３（７０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例６：ＩＴＯ／α−ＮＰＤ（５０ｎｍ）／Ａｌｑ３（４０ｎｍ）／Ｔｐ３３ＢＰＹＭＥＳ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例７：ＩＴＯ／α−ＮＰＤ（５０ｎｍ）／Ａｌｑ３（４０ｎｍ）／Ｔｍ３３ＢＰｙＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
Tp33BPYMES obtained in Example 2
Tm33BPyB obtained in Example 3
An organic EL element using each of these as an electron transporting material was produced and compared with an organic EL element using only typical Alq 3 as an electron transporting material (Comparative Example 2).
Comparative Example 2 of Organic EL Element: ITO / α-NPD (50 nm) / Alq 3 (70 nm) / LiF (0.5 nm) / Al (100 nm)
Example 6: ITO / α-NPD (50 nm) / Alq 3 (40 nm) / Tp33BPYMES (30 nm) / LiF (0.5 nm) / Al (100 nm)
Example 7: ITO / α-NPD (50 nm) / Alq 3 (40 nm) / Tm33BPyB (30 nm) / LiF (0.5 nm) / Al (100 nm)
実施例８、比較例３
実施例２で得られたＴｐ３３ＢＰＹＭＥＳを用いて緑リン光素子を作成した。
Ｔｐ３３ＢＰＹＭＥＳの代りにＢＣＰ／Ａｌｑ３を用いたものを比較例３とした。
有機ＥＬ素子の構成
比較例３：ＩＴＯ／ＴＰＤＰＥＳ：ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）３（９ｗｔ％）（３０ｎｍ）／ＢＣＰ（１０ｎｍ）／Ａｌｑ３（２０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例８：ＩＴＯ／ＴＰＤＰＥＳ：ＴＢＰＡＨ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）３（９ｗｔ％）（３０ｎｍ）／Ｔｐ３３ＢＰＹＭＥＳ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
ＴＰＤＰＥＳは、ポリ〔オキシ−１，４−フェニレンスルホニル−１，４−フェニレンオキシ−１，４−フェニレン（フェニルイミノ）（１，１′−ビフェニル）−４，４′−ジイル（フェニルイミノ）−１，４−フェニレン〕{ｐｏｌｙ〔ｏｘｙ−１，４−ｐｈｅｎｙｌｅｎｓｕｌｆｏｎｙｌ−１,４−ｐｈｅｎｙｌｅｎｅｏｘｙ−１，４−ｐｈｅｎｙｌｅｎｅ)（ｐｈｅｎｙｌｉｍｉｎｏ）（１，１′−ｂｉｐｈｅｎｙｌ）−４，４′−ｄｉｙｌ（ｐｈｅｎｙｌｉｍｉｎｏ）−１，４−ｐｈｅｎｙｌｅｎｅ〕}（９ＣＩ）（ＣＡ ＩＮＤＥＸ ＮＡＭＥ）の略称である。
ＴＢＰＡＨはトリス（４−ブロモフェニル）アミニウム ヘキサクロロアンチモネート〔Ｔｒｉｓ（４−ｂｒｏｍｏｐｈｅｎｙｌ）ａｍｉｎｉｕｍ ｈｅｘａｃｈｌｏｒｏａｎｔｉｍｏｎａｔｅ〕である。
A green phosphorescent device was prepared using Tp33BPYMES obtained in Example 2.
A comparative example 3 was prepared by using BCP / Alq 3 instead of Tp33BPYMES.
Comparative Example 3 of Organic EL Element: ITO / TPDPES: TBPAH (20 nm) / TAPC (30 nm) / CBP: Ir (ppy) 3 (9 wt%) (30 nm) / BCP (10 nm) / Alq 3 (20 nm) / LiF (0.5 nm) / Al (100 nm)
Example 8: ITO / TPDPES: TBPAH (20 nm) / TAPC (30 nm) / CBP: Ir (ppy) 3 (9 wt%) (30 nm) / Tp33BPYMES (30 nm) / LiF (0.5 nm) / Al (100 nm)
TPDPES is a poly [oxy-1,4-phenylenesulfonyl-1,4-phenyleneoxy-1,4-phenylene (phenylimino) (1,1'-biphenyl) -4,4'-diyl (phenylimino)- 1,4-phenylene] {poly [oxy-1,4-phenylsulfonyl-1,4-phenylene-1,4-phenylene) (phenylimino) (1,1′-biphenyl) -4,4′-diyl (phenylimino) -1,4-phenylene]} (9CI) (CA INDEX NAME).
TBPAH is tris (4-bromophenyl) aminium hexachloroantimonate [Tris (4-bromophenyl) aminium hexachloroantimonate].
実施例９、１０
実施例９として、実施例４で得られたＴｍ２３ＢＰｙＢを用い、実施例１０として、実施例３で得られたＴｍ３３ＢＰｙＢを用い、それぞれ下記構成の有機ＥＬ素子を作り、比較例２の有機ＥＬ素子と対比した。
有機ＥＬ素子の構成
比較例２；○：ＩＴＯ／α−ＮＰＤ（５０ｎｍ）／Ａｌｑ３（７０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例９；△：ＩＴＯ／α−ＮＰＤ（５０ｎｍ）／Ａｌｑ３（４０ｎｍ）／Ｔｍ２３ＢＰｙＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例１０；◇：ＩＴＯ／α−ＮＰＤ（５０ｎｍ）／Ａｌｑ３（４０ｎｍ）／Ｔｍ３３ＢＰｙＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
図１１に各素子の電流密度−電圧特性を、
図１２に各素子の輝度 −電圧特性を、
図１３に各素子の視感効率−電圧特性を、
図１４に各素子の電流効率−電圧特性を、
図１５に各素子の視感効率−輝度特性を、
図１６に各素子のＥＬスペクトルを
それぞれ示す。
Ｔｍ２３ＢＰｙＢとＴｍ３３ＢＰｙＢのそれぞれの電子輸送性の評価は下記表４に示す。
As Example 9, the Tm23BPyB obtained in Example 4 was used, and the Tm33BPyB obtained in Example 3 was used as Example 10, and the organic EL elements having the following constitutions were respectively produced. Contrast.
Comparative Example 2 of Organic EL Element: ○: ITO / α-NPD (50 nm) / Alq 3 (70 nm) / LiF (0.5 nm) / Al (100 nm)
Example 9; Δ: ITO / α-NPD (50 nm) / Alq 3 (40 nm) / Tm23BPyB (30 nm) / LiF (0.5 nm) / Al (100 nm)
Example 10; ◇: ITO / α-NPD (50 nm) / Alq 3 (40 nm) / Tm33BPyB (30 nm) / LiF (0.5 nm) / Al (100 nm)
FIG. 11 shows current density-voltage characteristics of each element.
FIG. 12 shows the luminance-voltage characteristics of each element.
FIG. 13 shows the luminous efficiency-voltage characteristics of each element.
FIG. 14 shows current efficiency-voltage characteristics of each element.
FIG. 15 shows the luminous efficiency-luminance characteristics of each element.
FIG. 16 shows an EL spectrum of each element.
The evaluation of the electron transport properties of Tm23BPyB and Tm33BPyB is shown in Table 4 below.
実施例１１、１２、比較例４
前記ＴｍＰｙＰｈＢに対して、実施例４で得られたＴｍ２３ＢＰｙＢと実施例３で得られたＴｍ３３ＢＰｙＢの電子輸送性を評価するため、下記の有機ＥＬ素子を作った。
有機ＥＬ素子の構成
比較例４；○：ＩＴＯ／ＴＰＤＰＥＳ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）３（８ｗｔ％）（３０ｎｍ）／ＴｍＰｙＰｈＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例１１；△：ＩＴＯ／ＴＰＤＰＥＳ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）３（８ｗｔ％）（３０ｎｍ）／Ｔｍ２３ＢＰｙＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例１２；◇：ＩＴＯ／ＴＰＤＰＥＳ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）３（８ｗｔ％）（３０ｎｍ）／Ｔｍ３３ＢＰｙＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
図１７に各素子の電流密度−電圧特性を、
図１８に各素子の輝度 −電圧特性を、
図１９に各素子の輝度 −電流密度特性を、
図２０に各素子の外部量子効率−輝度特性を、
図２１に各素子の視感効率−輝度特性を、
図２２に各素子の電流効率−電圧特性を、
図２３に各素子の視感効率−電圧特性を、
図２４に各素子の電流効率−電流密度特性を、
図２５に各素子のＥＬスペクトルを
それぞれ示す。
Examples 11 and 12 and Comparative Example 4
In order to evaluate the electron transport properties of Tm23BPyB obtained in Example 4 and Tm33BPyB obtained in Example 3 with respect to TmPyPhB, the following organic EL devices were prepared.
Comparative Example 4 of Organic EL Element; ○: ITO / TPDPES (20 nm) / TAPC (30 nm) / CBP: Ir (ppy) 3 (8 wt%) (30 nm) / TmPyPhB (30 nm) / LiF (0.5 nm) / Al (100 nm)
Example 11; Δ: ITO / TPDPES (20 nm) / TAPC (30 nm) / CBP: Ir (ppy) 3 (8 wt%) (30 nm) / Tm23BPyB (30 nm) / LiF (0.5 nm) / Al (100 nm)
Example 12: ◇: ITO / TPDPES (20 nm) / TAPC (30 nm) / CBP: Ir (ppy) 3 (8 wt%) (30 nm) / Tm33BPyB (30 nm) / LiF (0.5 nm) / Al (100 nm)
FIG. 17 shows the current density-voltage characteristics of each element.
FIG. 18 shows the luminance-voltage characteristics of each element.
FIG. 19 shows the luminance-current density characteristics of each element.
FIG. 20 shows the external quantum efficiency-luminance characteristics of each element.
FIG. 21 shows the luminous efficiency-luminance characteristics of each element.
FIG. 22 shows current efficiency-voltage characteristics of each element.
FIG. 23 shows the luminous efficiency-voltage characteristics of each element.
FIG. 24 shows the current efficiency-current density characteristics of each element.
FIG. 25 shows the EL spectrum of each element.
実施例１３、１４、比較例５
実施例１〜５に準じて、下記本発明のＴｍ２４ＢＰｙＢ［トリス−１，３，５−〔６′−（ピリジン−４″−イル）ピリジン−２′−イル〕ベンゼン｛Ｔｒｉｓ−１，３，５−〔６′−（ｐｙｒｉｄｉｎｅ−４″−ｙｌ）ｐｙｒｉｄｉｎｅ−２′−ｙｌ〕ｂｅｎｚｅｎｅ｝］およびＴｍ３４ＢＰｙＢ［トリス−１，３，５−〔６′−（ピリジン−４″−イル）ピリジン−３′−イル〕ベンゼン｛Ｔｒｉｓ−１，３，５−〔６′−（ｐｙｒｉｄｉｎｅ−４″−ｙｌ）ｐｙｒｉｄｉｎｅ−３′−ｙｌ〕ｂｅｎｚｅｎｅ｝］を作り、これらを用いた有機ＥＬ素子と、対比のための下記Ｔｍ４ＰｙＰｈＢ［トリス−１，３，５−〔３′−（ピリジン−４″−イル）フェニル〕ベンゼン｛Ｔｒｉｓ−１，３，５−〔３′−（ｐｙｒｉｄｉｎｅ−４″−ｙｌ）ｐｈｅｎｙｌ〕ｂｅｎｚｅｎｅ｝］を用いた有機ＥＬ素子を作り、その性能を評価した。
比較例５；○：ＩＴＯ／ＴＰＤＰＥＳ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）３（８ｗｔ％）（３０ｎｍ）／Ｔｍ４ＰｙＰｈＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例１３；△：ＩＴＯ／ＴＰＤＰＥＳ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）３（８ｗｔ％）（３０ｎｍ）／Ｔｍ２４ＢＰｙＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
実施例１４；◇：ＩＴＯ／ＴＰＤＰＥＳ（２０ｎｍ）／ＴＡＰＣ（３０ｎｍ）／ＣＢＰ：Ｉｒ（ｐｐｙ）３（８ｗｔ％）（３０ｎｍ）／Ｔｍ３４ＢＰｙＢ（３０ｎｍ）／ＬｉＦ（０．５ｎｍ）／Ａｌ（１００ｎｍ）
図２６に各素子の電流密度−電圧特性を、
図２７に各素子の輝度 −電圧特性を、
図２８に各素子の輝度 −電流密度特性を、
図２９に各素子の外部量子効率−輝度特性を、
図３０に各素子の視感効率−輝度特性を、
図３１に各素子の電流効率−電圧特性を、
図３２に各素子の視感効率−電圧特性を、
図３３に各素子の電流効率−電流密度特性を、
図３４に各素子のＥＬスペクトルを
それぞれ示す。
Examples 13 and 14 and Comparative Example 5
According to Examples 1 to 5, Tm24BPyB [Tris-1,3,5- [6 ′-(pyridin-4 ″ -yl) pyridin-2′-yl] benzene {Tris-1,3, 5- [6 '-(pyridine-4 "-yl) pyridine-2'-yl] benzene}] and Tm34BPyB [Tris-1,3,5- [6'-(pyridin-4" -yl) pyridine-3 ′ -Yl] benzene {Tris-1,3,5- [6 ′-(pyridine-4 ″ -yl) pyridine-3′-yl] benzene}], and comparison with an organic EL device using them Tm4PyPhB [Tris-1,3,5- [3 '-(pyridin-4 "-yl) phenyl] benzene {Tris-1,3,5- [3'-(pyridine-4" -y) ) Phenyl] benzene}] make organic EL element was used to evaluate the performance.
Example 13; Δ: ITO / TPDPES (20 nm) / TAPC (30 nm) / CBP: Ir (ppy) 3 (8 wt%) (30 nm) / Tm24BPyB (30 nm) / LiF (0.5 nm) / Al (100 nm)
Example 14; ◇: ITO / TPDPES (20 nm) / TAPC (30 nm) / CBP: Ir (ppy) 3 (8 wt%) (30 nm) / Tm34BPyB (30 nm) / LiF (0.5 nm) / Al (100 nm)
FIG. 26 shows current density-voltage characteristics of each element.
FIG. 27 shows the luminance-voltage characteristics of each element.
FIG. 28 shows the luminance-current density characteristics of each element.
FIG. 29 shows the external quantum efficiency-luminance characteristics of each element.
FIG. 30 shows the luminous efficiency-luminance characteristics of each element.
FIG. 31 shows current efficiency-voltage characteristics of each element.
FIG. 32 shows luminous efficiency-voltage characteristics of each element.
FIG. 33 shows current efficiency-current density characteristics of each element.
FIG. 34 shows the EL spectrum of each element.
つぎに、実施例１１、１２、２３、１４および比較例４、５の緑色リン光素子の物性値を表７〜９に示す。
表８のデータは、輝度１００ｃｄ／ｍ２のときのデータである。ただし、比較例４のみは輝度１３８ｃｄ／ｍ２の時のデータである。
The data in Table 8 is data when the luminance is 100 cd / m 2 . However, only the comparative example 4 is data when the luminance is 138 cd / m 2 .
１ 基板
２ 陽極（ＩＴＯ）
３ 発光層
４ 陰極
５ 正孔輸送層（ホール輸送層）
６ 電子輸送層
７ 正孔注入層（ホール注入層）
８ 電子注入層
９ 正孔ブロック層（ホールブロック層）
1
3
6
8
Claims (3)
で示されるトリピリジルフェニル誘導体。 The following general formula (1)
A tripyridylphenyl derivative represented by:
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