JP6977330B2 - 新規なカルバゾール化合物及びその用途 - Google Patents
新規なカルバゾール化合物及びその用途 Download PDFInfo
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- JP6977330B2 JP6977330B2 JP2017122031A JP2017122031A JP6977330B2 JP 6977330 B2 JP6977330 B2 JP 6977330B2 JP 2017122031 A JP2017122031 A JP 2017122031A JP 2017122031 A JP2017122031 A JP 2017122031A JP 6977330 B2 JP6977330 B2 JP 6977330B2
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title description 6
- -1 carbazole compound Chemical class 0.000 claims description 315
- 239000000463 material Substances 0.000 claims description 59
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 229960001716 benzalkonium Drugs 0.000 claims 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 131
- 239000010410 layer Substances 0.000 description 70
- 238000000034 method Methods 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 34
- 238000000434 field desorption mass spectrometry Methods 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 238000004128 high performance liquid chromatography Methods 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- 239000000843 powder Substances 0.000 description 20
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 19
- 238000011156 evaluation Methods 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 238000005259 measurement Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 0 *(c(cccc1)c1-c1c2)c1ccc2N(c(cc1)cc2c1c1ccccc1[n]2-c(cccc1)c1-c1c2[n]c(C=CCC3)c3c2ccc1)c1ccccc1 Chemical compound *(c(cccc1)c1-c1c2)c1ccc2N(c(cc1)cc2c1c1ccccc1[n]2-c(cccc1)c1-c1c2[n]c(C=CCC3)c3c2ccc1)c1ccccc1 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 229940078552 o-xylene Drugs 0.000 description 10
- 238000007740 vapor deposition Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- KWHNHZKNXFVGGN-UHFFFAOYSA-N ClC1=CC=2N(C3=CC=CC=C3C=2C=C1)C1=C(C=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 Chemical compound ClC1=CC=2N(C3=CC=CC=C3C=2C=C1)C1=C(C=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 KWHNHZKNXFVGGN-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- OUDICVNRLYKWFB-UHFFFAOYSA-N ClC1=CC=2N(C3=CC=CC=C3C=2C=C1)C1=C(C=CC=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 Chemical compound ClC1=CC=2N(C3=CC=CC=C3C=2C=C1)C1=C(C=CC=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 OUDICVNRLYKWFB-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- BWMWHPFEZIXUNP-UHFFFAOYSA-N n-phenylphenanthren-9-amine Chemical compound C=1C2=CC=CC=C2C2=CC=CC=C2C=1NC1=CC=CC=C1 BWMWHPFEZIXUNP-UHFFFAOYSA-N 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- LOQQFCPPDBFFSO-UHFFFAOYSA-N 2-chloro-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Cl)C=C3NC2=C1 LOQQFCPPDBFFSO-UHFFFAOYSA-N 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAMLAVUKSDVTLY-UHFFFAOYSA-N ClC1=CC=2N(C3=CC=CC=C3C=2C=C1)C1=C(C=CC=C1)C1=CC2=C(SC3=C2C=CC=C3)C=C1 Chemical compound ClC1=CC=2N(C3=CC=CC=C3C=2C=C1)C1=C(C=CC=C1)C1=CC2=C(SC3=C2C=CC=C3)C=C1 IAMLAVUKSDVTLY-UHFFFAOYSA-N 0.000 description 3
- KAABELVPSMBKMP-UHFFFAOYSA-N ClC1=CC=CC=2N(C3=CC=CC=C3C1=2)C1=C(C=CC=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 Chemical compound ClC1=CC=CC=2N(C3=CC=CC=C3C1=2)C1=C(C=CC=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 KAABELVPSMBKMP-UHFFFAOYSA-N 0.000 description 3
- HNELDZHATQZASN-UHFFFAOYSA-N FC1=C(C=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 Chemical compound FC1=C(C=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 HNELDZHATQZASN-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 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 3
- 150000004767 nitrides Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 2
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 2
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 2
- LTUJKAYZIMMJEP-UHFFFAOYSA-N 9-[4-(4-carbazol-9-yl-2-methylphenyl)-3-methylphenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C)C(C)=C1 LTUJKAYZIMMJEP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YWYMNVAOTDKOQO-UHFFFAOYSA-N ClC1=CC=CC=2N(C3=CC=CC=C3C1=2)C1=C(C=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 Chemical compound ClC1=CC=CC=2N(C3=CC=CC=C3C1=2)C1=C(C=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 YWYMNVAOTDKOQO-UHFFFAOYSA-N 0.000 description 2
- MOTPOVYRRSLIMW-UHFFFAOYSA-N FC1=C(C=CC=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 Chemical compound FC1=C(C=CC=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 MOTPOVYRRSLIMW-UHFFFAOYSA-N 0.000 description 2
- GOZPTOHMTKTIQP-UHFFFAOYSA-N OC1=CC=CC2=CC=C3C=CC(=NC3=C21)C(=O)O Chemical compound OC1=CC=CC2=CC=C3C=CC(=NC3=C21)C(=O)O GOZPTOHMTKTIQP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 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
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- VWXSLLOSYCKNCF-UHFFFAOYSA-N n-phenyl-4-(4-phenylphenyl)aniline Chemical group C=1C=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 VWXSLLOSYCKNCF-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- FGYADSCZTQOAFK-UHFFFAOYSA-N 1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C=NC2=C1 FGYADSCZTQOAFK-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- WIAWDMBHXUZQGV-UHFFFAOYSA-N heptacyclo[13.10.1.12,6.011,26.017,25.018,23.010,27]heptacosa-1(25),2,4,6(27),7,9,11,13,15(26),17,19,21,23-tridecaene Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=C1C=C3C=CC=CC3=C1C2 WIAWDMBHXUZQGV-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- BBDFECYVDQCSCN-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-[4-(n-(4-methoxyphenyl)anilino)phenyl]-n-phenylaniline Chemical group C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(OC)=CC=1)C1=CC=CC=C1 BBDFECYVDQCSCN-UHFFFAOYSA-N 0.000 description 1
- MZKZCGLQGDKMBI-UHFFFAOYSA-N n-phenyldibenzothiophen-2-amine Chemical compound C=1C=C2SC3=CC=CC=C3C2=CC=1NC1=CC=CC=C1 MZKZCGLQGDKMBI-UHFFFAOYSA-N 0.000 description 1
- USPVIMZDBBWXGM-UHFFFAOYSA-N nickel;oxotungsten Chemical compound [Ni].[W]=O USPVIMZDBBWXGM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 235000011649 selenium Nutrition 0.000 description 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 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
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 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 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- NVCBVYYESHBQKS-UHFFFAOYSA-L zinc;2-carboxyquinolin-8-olate Chemical compound [Zn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 NVCBVYYESHBQKS-UHFFFAOYSA-L 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Description
以下に、一般式(1)で表されるカルバゾール化合物について、好ましい化合物を例示するが、本願発明はこれらの化合物に限定されるものではない。
一般式(5)、(6)及び(8)で表される化合物は、一般公知の方法に基づいて合成することができるし、市販されている化合物を用いることもできる。
測定装置:東ソー製 マルチステーションLC−8020
測定条件:カラム Inertsil ODS−3V(4.6mmΦ×250mm)
検出器 UV検出(波長 254nm)
溶離液 メタノール/テトラヒドロフラン=9/1(v/v比)
[NMR測定]
測定装置:バリアン社製 Gemini200
[質量分析]
質量分析装置:日立製作所 M−80B
測定方法:FD−MS分析
[有機EL素子の発光特性]
測定装置:TOPCON社製LUMINANCEMETER(BM−9)
合成例1 2−クロロ−9−(2−(4−ジベンゾチエニル)フェニル)カルバゾールの合成
1H−NMR(CDCl3);7.98(d,2H),7.89(d,1H),7.83(d,2H),7.74−7.57(m,4H),7.45−7.36(m,2H),7.20−7.04(m,5H),6.85(t,1H),6.68(d,1H)
13C−NMR(CDCl3);141.88,141.61,139.34,139.25,139.09,136.17,135.76,134.81,132.78,131.40,131.33,129.92,129.84,129.00,126.76,126.08,125.92,124.35,124.29,122.62,122.34,121.66,121.59,120.78,120.69,120.04,119.97,119.90,110.10
合成例2 2−クロロ−9−(2−(2−ジベンゾチエニル)フェニル)カルバゾールの合成
1H−NMR(CDCl3);7.92(d,1H),7.85(d,1H),7.76(d,2H),7.69(t,2H),7.60(t,1H),7.53(d,2H),7.44(d,1H),7.37−7.24(m,3H),7.18−7.09(m,5H)
13C−NMR(CDCl3);141.93,141.81,141.09,139.56,138.56,135.39,135.19,134.62,134.35,131.86,131.48,130.00,129.39,129.00,126.62,126.30,126.10,124.27,122.62,122.48,122.41,121.64,121.25,121.02,120.63,120.15,120.06,120.03,110.04,109.92
合成例3 2−クロロ−9−(2−(4−ジベンゾフラニル)フェニル)カルバゾールの合成
1H−NMR(CDCl3);1H−NMR(CDCl3);7.88(d,1H),7.82(d,1H),7.76−7.59(m,6H),7.33−7.14(m,5H),7.10−6.97(m,5H)
合成例4 4−クロロ−9−(2−(4−ジベンゾチエニル)フェニル)カルバゾールの合成
合成例5 4−クロロ−9−(2−(4−ジベンゾフラニル)フェニル)カルバゾールの合成
実施例1 (化合物(A11)の合成)
1H−NMR(CDCl3);7.98−7.81(m,5H),7.70(d,1H),7.62−7.52(m,7H),7.41(t,4H),7.32−7.17(m,11H),6.92(t,1H),6.83(d,2H),6.70−6.26(m,5H)
13C−NMR(CDCl3);148.26,147.09,145.19,142.25,140.75,139.34,139.16,139.03,136.18,135.68,135.07,134.34,133.19,131.22,129.96,129.69,128.68,127.32,126.70,126.64,126.56,126.17,125.29,124.32,124.20,123.00,122.52,121.71,120.63,120.50,119.89,119.69,119.56,118.96,109.78,107.79
実施例2 (化合物(A14)の合成)
実施例3 (化合物(A18)の合成)
1H−NMR(CDCl3);8.15(d,2H),7.94(dd,3H),7.82(t,2H),7.63(t,4H),7.44(t,2H),7.36−7.20(m,9H),7.09(d,4H),6.92−6.81(m,4H),6.78−6.60(m,5H)
13C−NMR(CDCl3);147.59,147.28,145.39,142.31,141.77,141.15,139.34,139.14,138.92,136.19,135.68,135.03,133.11,131.16,130.48,130.00,129.67,128.93,128.66,127.40,126.70,126.14,125.73,125.36,124.39,124.33,123.79,123.12,123.09,123.02,122.55,122.50,121.61,120.66,120.44,120.22,119.97,119.73,119.61,119.46,118.68,109.91,109.76,107.40
実施例4 (化合物(A31)の合成)
1H−NMR(CDCl3);8.00(d,1H),7.84(d,1H),7.75−7.65(m,3H),7.61−6.23(m,24H),7.06(d,1H),6.88−6.81(m,6H)
13C−NMR(CDCl3);147.13,145.21,142.47,141.74,140.63,140.57,139.54,138.42,135.42,135.24,134.92,134.60,134.54,131.82,130.07,129.12,128.87,128.70,127.52,126.70,126.58,126.41,125.53,124.33,123.10,122.64,122.50,121.34,121.01,120.66,120.01,119.93,119.73,119.04,109.74,107.61
実施例5 (化合物(B11)の合成)
1H−NMR(CDCl3);7.87(d,1H),7.79(dd,2H),7.68(dd,2H),7.64−7.54(m,7H),7.44−7.27(m,12H),7.23(t,1H),7.15(dd,2H)7.05(d,1H),6.98(t,1H),6.91(d,1H),6.82(d,6H)
13C−NMR(CDCl3);155.81,153.15,147.13,145.00,142.03,141.55,140.74,135.60,135.28,134.48,132.68,129.47,129.41,128.71,128.39,127.46,126.99,126.90,126.67,126.59,125.11,124.25,123.79,123.18,123.14,122.98,122.66,122.46,120.69,120.43,119.81,119.78,119.73,119.59,118.83,111.53,110.09,107.74
実施例6 (化合物(B18)の合成)
1H−NMR(CDCl3);8.15(d,2H),7.92−7.81(m,3H),7.17−7.64(m,5H),7.47−7.06(m,16H),6.94(t,2H),6.89−6.80(m,7H)
13C−NMR(CDCl3);155.84,153.14,148.28,147.58,147.33,145.13,142.08,141.52,141.15,135.51,135.23,132.70,130.52,129.56,129.39,129.08,128.39,127.50,126.90,125.77,125.22,124.31,123.83,123.14,123.06,122.98,122.67,122.60,122.51,120.78,120.41,120.23,119.86,119.80,119.63,118.72,111.56,110.07,109.87,107.64
実施例13 (化合物(A3)の合成)
実施例14 (化合物(A12)の合成)
実施例15 (化合物(A81)の合成)
実施例16 (化合物(A87)の合成)
実施例17 (化合物(A88)の合成)
実施例18 (化合物(B12)の合成)
実施例19 (化合物(A41)の合成)
実施例20 (化合物(A51)の合成)
実施例21 (化合物(B51)の合成)
実施例7 (化合物(A11)の素子評価)
厚さ200nmのITO透明電極(陽極)を積層したガラス基板を、アセトン及び純水による超音波洗浄、イソプロピルアルコールによる沸騰洗浄を行なった。さらに、紫外線/オゾン洗浄を行ない、真空蒸着装置へ設置後、1×10−4Paになるまで真空ポンプにて排気した。まず、ITO透明電極上に銅フタロシアニンを蒸着速度0.1nm/秒で蒸着し、10nmの正孔注入層とし、引続き、化合物(A11)を蒸着速度0.3nm/秒で30nm蒸着して正孔輸送層とした。続いて、燐光ドーパント材料であるトリス(2−フェニルピリジン)イリジウム(Ir(ppy)3)とホスト材料である4,4’−ビス(N−カルバゾリル)ビフェニル(CBP)を重量比が1:11.5になるように蒸着速度0.25nm/秒で共蒸着し、30nmの発光層とした。次に、BAlq(ビス(2−メチル−8−キノリノラト)(p−フェニルフェノラート)アルミニウム)を蒸着速度0.3nm/秒で蒸着し、5nmのエキシトンブロック層とした後、さらにAlq3(トリス(8−キノリノラト)アルミニウム)を0.3nm/秒で蒸着し、45nmの電子輸送層とした。引続き、電子注入層として沸化リチウムを蒸着速度0.01nm/秒で1nm蒸着し、さらにアルミニウムを蒸着速度0.25nm/秒で100nm蒸着して陰極を形成した。窒素雰囲気下、封止用のガラス板をUV硬化樹脂で接着し、評価用の有機EL素子とした。このように作製した素子に20mA/cm2の電流を印加し、駆動電圧及び電流効率を測定した。また、素子に6.25mA/cm2の電流を印加して輝度の経時変化を測定し、輝度が初期の半分になる時間(輝度半減期)を調べた。当該輝度半減期を素子寿命として評価した。結果を表1に示した。なお、素子寿命については、後述する比較例1の素子寿命(輝度半減期)を100とした相対値で表した。
化合物(A11)の代わりに、化合物(A14)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A18)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A31)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(B11)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(B18)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A3)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A12)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A81)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A87)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A88)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(B12)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A41)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(A51)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
化合物(A11)の代わりに、化合物(B51)を用いた以外は実施例7と同じ方法で有機EL素子を作製した。前記有機EL素子について、実施例7と同じ方法で測定した駆動電圧、電流効率、及び素子寿命を表1に示した。
市販品のNPD(4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル)を昇華精製した。昇華品のNPDは結晶性粉末状であることを確認した。
特開2015−071582公報の記載に基づいて、下記化合物(a)を合成し、昇華精製した。
Claims (10)
- R1が前記一般式(2)で表される基であり尚且つR2が水素原子であることを特徴とする、請求項1〜3のいずれか1項に記載のカルバゾール化合物。
- R 2 が前記一般式(2)で表される基であり尚且つR 1 が水素原子であることを特徴とする、請求項1〜3のいずれか1項に記載のカルバゾール化合物。
- Ar1及びAr2が、各々独立して、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、フルオレニル基、フェナントリル基、ジベンゾチエニル基、及びジベンゾフラニル基[これらの基は、各々独立して、メチル基、9−カルバゾリル基、ジベンゾチエニル基、及びジベンゾフラニル基からなる群より選ばれる置換基を1種以上有していてもよい]であることを特徴とする請求項1〜5のいずれか1項に記載のカルバゾール化合物。
- Ar1及びAr2が、各々独立して、フェニル基、4−メチルフェニル基、4−(9−カルバゾリル)フェニル基、4−(4−ジベンゾチエニル)フェニル基、4−(4−ジベンゾフラニル)フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、9,9−ジメチル−2−フルオレニル基、フェナントリル基、ジベンゾチエニル基、及びジベンゾフラニル基であることを特徴とする請求項1〜5のいずれか1項に記載のカルバゾール化合物。
- 請求項1〜9のいずれか1項に記載のカルバゾール化合物を含むことを特徴とする、有機EL素子用材料。
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