JP2020132549A - トリフェニレン化合物及びその用途 - Google Patents
トリフェニレン化合物及びその用途 Download PDFInfo
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- JP2020132549A JP2020132549A JP2019025688A JP2019025688A JP2020132549A JP 2020132549 A JP2020132549 A JP 2020132549A JP 2019025688 A JP2019025688 A JP 2019025688A JP 2019025688 A JP2019025688 A JP 2019025688A JP 2020132549 A JP2020132549 A JP 2020132549A
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- carbon atoms
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- phenyl
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- -1 Triphenylene compound Chemical class 0.000 title claims abstract description 400
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 30
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 92
- 239000000463 material Substances 0.000 claims description 45
- 125000002950 monocyclic group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 16
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000002521 alkyl halide group Chemical group 0.000 claims description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 230000033116 oxidation-reduction process Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 83
- 239000010410 layer Substances 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 230000005525 hole transport Effects 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000000434 field desorption mass spectrometry Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 8
- 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 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229940078552 o-xylene Drugs 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 238000002484 cyclic voltammetry Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 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
- 230000009477 glass transition Effects 0.000 description 3
- 150000004820 halides 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
- 150000004767 nitrides Chemical class 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- 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
- RFGQPOXKXWAPNQ-UHFFFAOYSA-N 1-N-phenyl-3-N,3-N-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound N(c1ccccc1)c1cccc(c1)N(c1ccc(cc1)-c1ccccc1)c1ccc(cc1)-c1ccccc1 RFGQPOXKXWAPNQ-UHFFFAOYSA-N 0.000 description 2
- NXXNBEYMRKHPKK-UHFFFAOYSA-N 1-chlorotriphenylene Chemical group C1=CC=CC2=C3C(Cl)=CC=CC3=C(C=CC=C3)C3=C21 NXXNBEYMRKHPKK-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
- CRAKIPJUCBZTDP-UHFFFAOYSA-N 3-N,3-N-diphenyl-1-N-(4-phenylphenyl)benzene-1,3-diamine Chemical compound C1=CC=CC=C1C1=CC=C(NC2=CC=CC(N(C3=CC=CC=C3)C3=CC=CC=C3)=C2)C=C1 CRAKIPJUCBZTDP-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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- YUIVYVFBRORXIO-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2 Chemical compound C1(=CC=CC=C1)NC1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2 YUIVYVFBRORXIO-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
- 239000007983 Tris buffer Substances 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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 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
- 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 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 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
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 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
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 2
- 125000000335 thiazolyl group Chemical group 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
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 125000005580 triphenylene group Chemical group 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 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
- GWQSENYKCGJTRI-UHFFFAOYSA-N 1-chloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1 GWQSENYKCGJTRI-UHFFFAOYSA-N 0.000 description 1
- QFUYDAGNUJWBSM-UHFFFAOYSA-N 1-iodo-2-phenylbenzene Chemical group IC1=CC=CC=C1C1=CC=CC=C1 QFUYDAGNUJWBSM-UHFFFAOYSA-N 0.000 description 1
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- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002524 organometallic group Chemical group 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
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- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 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
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 125000001725 pyrenyl 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
- 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
- 230000002441 reversible effect Effects 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
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 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
- 238000004528 spin coating Methods 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 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
- 239000010409 thin film Substances 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
- 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
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000001771 vacuum deposition 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
L1及びL2は、各々独立して、単結合、又は炭素数6〜20の単環、連結環、若しくは縮合環の2価芳香族炭化水素基[これらの基は、各々独立して、メチル基、エチル基、炭素数3〜18の直鎖、分岐、又は環状のアルキル基、メトキシ基、エトキシ基、炭素数3〜18の直鎖、分岐、又は環状のアルコキシ基、炭素数1〜3のハロゲン化アルキル基、炭素数1〜3のハロゲン化アルコキシ基、炭素数6〜20の単環、連結環、又は縮合環のアリール基、炭素数6〜18の単環、連結環、又は縮合環のアリールオキシ基、炭素数3〜20の単環、連結環、又は縮合環のヘテロアリール基、炭素数3〜18のトリアルキルシリル基、炭素数18〜40のトリアリールシリル基、シアノ基、ハロゲン原子、及び重水素原子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。]を表す。
R1〜R3は、各々独立して、メチル基、メトキシ基、又はシアノ基を表し、n、及びmは、各々独立して、0〜4の整数を表し、pは、0〜3の整数を表す。)
また、前記一般式(2)で表される1−ハロゲン化トリフェニレン化合物は、公知の方法(Organic Letters,2018年,第20巻,5402頁)で合成することが可能である。
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 Gemini300
[質量分析]
質量分析装置:日立製作所社製 M−80B
測定方法:FD−MS分析
[酸化還元安定性評価]
測定装置:北斗電工社製 HSV−110
[有機EL素子の発光特性]
測定装置:TOPCON社製LUMINANCEMETER(BM−9)
窒素気流下、1000mLの三口フラスコに2−ヨードビフェニル 74.1g(264.4mmol)、2,6−ジクロロ安息香酸 50.0g(261.8mmol)、炭酸カリウム 90.5g(654.5mmol)、テトラキス(トリフェニルホスフィン)パラジウム 1.5g(1.3mmol)、ジメチルスルホキシド 300mLを加え、140℃で18時間攪拌した。室温まで冷却した後、トルエンを300mL及び純水を300mL加え、水層と有機層を分液し、有機層を飽和塩化ナトリウム水溶液で洗浄した。次いで当該有機層について、無水硫酸マグネシウムで乾燥後、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:1))で精製し、さらに減圧下に濃縮して得た残渣を再結晶(トルエン/2−プロパノール)することで、化合物(7)の白色固体を54.9g(208.9mmol)単離した(収率80%)。
合成例2 化合物(8)の合成
窒素気流下、500mLの三口フラスコに合成例1で得られた化合物(7) 24.4g(92.8mmol)、ビス(ピナコラト)ジボロン 33g(130.0mmol)、酢酸カリウム 27.4(278.4mmol)、酢酸パラジウム 104mg(0.46mmol)、トリシクロヘキシルホスフィン 260mg(0.93mmol)、ジメチルスルホキシド 200mLを加え、120℃で3時間攪拌した。室温まで冷却した後、トルエンを200mL及び純水を200mL加え、水層と有機層を分液し、有機層を飽和塩化ナトリウム水溶液で洗浄した。次いで当該有機層について、無水硫酸マグネシウムで乾燥後、減圧下に濃縮することで、化合物(8)の淡黄色粘性液体 31.2g(88.2mmol)を単離した(収率95%)。
合成例3 化合物(9)の合成
窒素気流下、300mLの三口フラスコに合成例2で得られた化合物(8) 11.0g(31.0mmol)、1−クロロ−4−ヨードベンゼン 8.9g(37.2mmol)、炭酸カリウム 12.8(93.0mmol)、テトラキス(トリフェニルホスフィン)パラジウム 1.1g(0.93mmol)、ジメチルスルホキシド 100mLを加え、120℃で18時間攪拌した。室温まで冷却した後、トルエンを100mL及び純水を100mL加え、水層と有機層を分液し、有機層を飽和塩化ナトリウム水溶液で洗浄した。次いで当該有機層について、無水硫酸マグネシウムで乾燥後、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:4))で精製することにより、化合物(9)の白色固体 5.4g(15.9mmol)を単離した(収率51%)。
合成例4 化合物(10)の合成
窒素気流下、50mLの三口フラスコに、合成例1で得た1−クロロトリフェニレン(化合物(7)) 10.0g(38.1mmol)、アニリン 10.6g(114.3mmol)、ナトリウム−tert−ブトキシド 4.8g(49.5mmol)、及びo−キシレン 100mLを加え、得られたスラリー状の反応液に酢酸パラジウム 171.1mg(0.76mmol)、及びトリ−tert−ブチルホスフィン 462.5mg(2.3mmol)を添加して140℃で24時間攪拌した。室温まで冷却後、純水を100mL添加し攪拌した。水層と有機層を分液し、有機層を飽和塩化ナトリウム水溶液で洗浄した。次いで当該有機層について、無水硫酸マグネシウムで乾燥後、減圧下に濃縮した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:1))で精製し、さらに減圧下に濃縮して得た残渣を再結晶(トルエン/ブタノール)することで、化合物(10)の白色粉末を6.0g(18.8mmol)単離した(収率49%)。
実施例1 (化合物(A7)の合成)
実施例2 (化合物(A89)の合成)
実施例3 (化合物(A182)の合成)
化合物の同定はFDMSにより行った。
実施例4 (化合物(B45)の合成)
実施例5 (化合物(B49)の合成)
実施例6 (化合物(A159)の合成)
実施例7 (化合物(A182)の酸化還元安定性評価)
サイクリックボルタンメトリーで化合物(A182)の酸化還元安定性を評価した。過塩素酸テトラブチルアンモニウムの濃度が0.1mol/Lである無水ジクロロメタン溶液に化合物(A182)を0.001mol/Lの濃度で溶解させ、作用電極にグラッシーカーボン、対極に白金線、参照電極にAgNO3のアセトニトリル溶液に浸した銀線を用いて、化合物(A182)のサイクリックボルタモグラムを得た(図1)。化合物(A182)は可逆な酸化還元波を示し、二電子酸化に対して安定であった。
実施例7と同様の方法で、韓国特許出願公開第10−2017−0136915号明細書の第27頁に記載されている化合物(後段に記載の化合物(a)に相当)の酸化還元安定性を評価した。化合物(a)は第二酸化が不可逆であり(図2)、二電子酸化に対して不安定であった。
素子評価に用いた化合物の構造式およびその略称を以下に示す。
化合物(A7)の代わりに、化合物(A89)を用いた以外は実施例8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8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(A7)の代わりに、化合物(A182)を用いた以外は実施例8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8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(A7)の代わりに、化合物(B45)を用いた以外は実施例8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8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(A7)の代わりに、化合物(B49)を用いた以外は実施例8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8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(A7)の代わりに、化合物(A159)を用いた以外は実施例8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8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(A7)の代わりに、下記化合物(a)を用いた以外は実施例8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8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(A7)の代わりに、国際公開第2010/002850号パンフレットの第21頁に記載されている化合物A−1(下記の化合物(b)に相当)を用いた以外は実施例8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8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。
Claims (7)
- 一般式(1)で表されるトリフェニレン化合物。
L1及びL2は、各々独立して、単結合、又は炭素数6〜20の単環、連結環、若しくは縮合環の2価芳香族炭化水素基[これらの基は、各々独立して、メチル基、エチル基、炭素数3〜18の直鎖、分岐、又は環状のアルキル基、メトキシ基、エトキシ基、炭素数3〜18の直鎖、分岐、又は環状のアルコキシ基、炭素数1〜3のハロゲン化アルキル基、炭素数1〜3のハロゲン化アルコキシ基、炭素数6〜20の単環、連結環、又は縮合環のアリール基、炭素数6〜18の単環、連結環、又は縮合環のアリールオキシ基、炭素数3〜20の単環、連結環、又は縮合環のヘテロアリール基、炭素数3〜18のトリアルキルシリル基、炭素数18〜40のトリアリールシリル基、シアノ基、ハロゲン原子、及び重水素原子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。]を表す。
R1〜R3は、各々独立して、メチル基、メトキシ基、又はシアノ基を表し、n、及びmは、各々独立して、0〜4の整数を表し、pは、0〜3の整数を表す。) - Ar1〜Ar3が、各々独立して、炭素数6〜20の単環、連結環、若しくは縮合環の芳香族炭化水素基、又は炭素数3〜16の単環、連結環、若しくは縮合環のヘテロ芳香族基[これらの基は、各々独立して、メチル基、シアノ基、フェニル基、トリフェニルシリル基、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に記載のトリフェニレン化合物。
- Ar1〜Ar3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、ナフチルフェニル基、フルオレニル基、フェナントリル基、フェナントリルフェニル基、カルバゾリル基、ジベンゾチエニル基、又は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、シアノ基、フェニル基、トリフェニルシリル基、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又は2に記載のトリフェニレン化合物。
- Ar1〜Ar3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、ジベンゾチエニル基、ジベンゾフラニル基、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、9,9−ジフェニル−2−フルオレニル基、又はフェナントリル基であることを特徴とする請求項1乃至3のいずれか1つに記載のトリフェニレン化合物。
- L1及びL2が、各々独立して、単結合、又は炭素数6〜14の単環、連結環、若しくは縮合環の2価芳香族炭化水素基[これらの基は、各々独立して、メチル基、エチル基、炭素数3〜18の直鎖、分岐、又は環状のアルキル基、メトキシ基、エトキシ基、炭素数3〜18の直鎖、分岐、又は環状のアルコキシ基、炭素数1〜3のハロゲン化アルキル基、炭素数1〜3のハロゲン化アルコキシ基、炭素数6〜20の単環、連結環、又は縮合環のアリール基、炭素数6〜18の単環、連結環、又は縮合環のアリールオキシ基、炭素数3〜20の単環、連結環、又は縮合環のヘテロアリール基、炭素数3〜18のトリアルキルシリル基、炭素数18〜40のトリアリールシリル基、シアノ基、ハロゲン原子、及び重水素原子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乃至4のいずれか1つに記載のトリフェニレン化合物。
- L1及びL2が、各々独立して、単結合、フェニレン基、又はビフェニリレン基であることを特徴とする請求項1乃至5のいずれか1つに記載のトリフェニレン化合物。
- 請求項1乃至6のいずれか1つに記載のトリフェニレン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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