JP7363045B2 - Triphenylene compounds and their uses - Google Patents
Triphenylene compounds and their uses Download PDFInfo
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- JP7363045B2 JP7363045B2 JP2019025688A JP2019025688A JP7363045B2 JP 7363045 B2 JP7363045 B2 JP 7363045B2 JP 2019025688 A JP2019025688 A JP 2019025688A JP 2019025688 A JP2019025688 A JP 2019025688A JP 7363045 B2 JP7363045 B2 JP 7363045B2
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- monocyclic
- ring
- phenyl
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- 125000005580 triphenylene group Chemical group 0.000 title claims description 4
- -1 triphenylene compound Chemical class 0.000 claims description 378
- 125000004432 carbon atom Chemical group C* 0.000 claims description 90
- 150000001875 compounds Chemical class 0.000 claims description 82
- 239000000463 material Substances 0.000 claims description 47
- 125000002950 monocyclic group Chemical group 0.000 claims description 43
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000005561 phenanthryl 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
- 229910052805 deuterium Inorganic materials 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- 239000010410 layer Substances 0.000 description 71
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 230000005525 hole transport Effects 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 21
- 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
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 11
- 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
- 239000000243 solution Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method 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
- 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- 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
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229940078552 o-xylene Drugs 0.000 description 5
- 229910052763 palladium Inorganic materials 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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 238000002484 cyclic voltammetry Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 125000004431 deuterium atom Chemical group 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
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000010408 film Substances 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000005412 pyrazyl group Chemical group 0.000 description 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 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
- 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
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-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
- RAPHUPWIHDYTKU-WXUKJITCSA-N 9-ethyl-3-[(e)-2-[4-[4-[(e)-2-(9-ethylcarbazol-3-yl)ethenyl]phenyl]phenyl]ethenyl]carbazole Chemical compound C1=CC=C2C3=CC(/C=C/C4=CC=C(C=C4)C4=CC=C(C=C4)/C=C/C=4C=C5C6=CC=CC=C6N(C5=CC=4)CC)=CC=C3N(CC)C2=C1 RAPHUPWIHDYTKU-WXUKJITCSA-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
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 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
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 150000004767 nitrides Chemical class 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
- 125000002971 oxazolyl group Chemical group 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
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 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
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 125000004434 sulfur atom Chemical group 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
- 125000001544 thienyl 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
- 229910052723 transition metal Inorganic materials 0.000 description 2
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- 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
- 239000007788 liquid 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
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 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
- VBQIVFTUXFKGKW-UHFFFAOYSA-N n-[4-(4-bromophenyl)phenyl]-4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 VBQIVFTUXFKGKW-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 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
- 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
- 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
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 108091008695 photoreceptors Proteins 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
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 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
- 239000002356 single layer 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
- 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 150000004882 thiopyrans Chemical class 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 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
- 238000007738 vacuum evaporation 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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- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、新規なトリフェニレン化合物及びそれを用いた有機ＥＬ素子に関するものである。 The present invention relates to a novel triphenylene compound and an organic EL device using the same.
有機ＥＬ素子は、有機薄膜を１対の電極で狭持した面発光型素子であり、薄型軽量、高視野角、高速応答性といった特徴を有し、各種表示素子への応用が期待されている。有機ＥＬ素子とは、陽極から注入された正孔と、陰極から注入された電子とが発光層で再結合する際に発する光を利用した素子であり、その構造は正孔輸送層、発光層、電子輸送層等を積層した多層積層型が特徴である。ここで、正孔輸送層や電子輸送層といった電荷輸送層は、それ自体は発光するわけではないが、発光層への電荷注入を容易にし、また、発光層に注入された電荷や発光層で生成した励起子のエネルギーを閉じ込めるといった役割を果たしている。従って、電荷輸送層は有機ＥＬ素子の低駆動電圧化および発光効率を向上させる上で非常に重要である。 Organic EL devices are surface-emitting devices in which an organic thin film is sandwiched between a pair of electrodes, and are characterized by being thin and lightweight, with a wide viewing angle, and high-speed response, and are expected to be applied to various display devices. . An organic EL device is an element that utilizes the light emitted when holes injected from the anode and electrons injected from the cathode recombine in a light emitting layer, and its structure consists of a hole transport layer, a light emitting layer. It is characterized by its multilayer structure, in which electron transport layers and the like are stacked. Here, the charge transport layers such as the hole transport layer and the electron transport layer do not emit light themselves, but they facilitate the injection of charge into the light emitting layer, and the charges injected into the light emitting layer and the light emitting layer are It plays the role of confining the energy of generated excitons. Therefore, the charge transport layer is very important in reducing the driving voltage and improving the luminous efficiency of organic EL devices.
正孔輸送材料には、適当なイオン化ポテンシャルと正孔輸送能を有するアリールアミン化合物が用いられ、そのようなアミン化合物として４，４’－ビス［Ｎ－（１－ナフチル）－Ｎ－フェニルアミノ］ビフェニル（以下、ＮＰＤと略す）が標準的材料として広く認知されている（例えば、非特許文献１）。しかし、ＮＰＤは、ガラス転移温度が十分高くないことから、素子寿命に課題があった。また、ＮＰＤを正孔輸送層に用いた素子の駆動電圧、発光効率も市場要求を満足するほどではなかった。 As the hole transport material, an arylamine compound having an appropriate ionization potential and hole transport ability is used. ] Biphenyl (hereinafter abbreviated as NPD) is widely recognized as a standard material (for example, Non-Patent Document 1). However, since NPD does not have a sufficiently high glass transition temperature, there is a problem with the device life. Furthermore, the driving voltage and luminous efficiency of devices using NPD in the hole transport layer did not meet market requirements.
このような背景から、高いガラス転移温度を確保でき、正孔輸送性に優れる縮合環を導入したアリールアミン化合物の開発が進められている。高いガラス転移温度の縮合環の一例としては、トリフェニレン環構造が知られている（例えば、特許文献１及び２）。しかし、特許文献１に開示された化合物を用いた有機ＥＬ素子の発光効率及び素子寿命は十分とは言い難く、さらなる改善が求められていた。また、有機ＥＬ素子において電荷輸送材料は電荷輸送の為に酸化還元を絶えず繰返しているが、特許文献２に開示された１－アミノトリフェニレン化合物については、酸化還元に対する安定性に改善の余地があった。 Against this background, progress is being made in the development of arylamine compounds into which condensed rings are introduced, which can ensure a high glass transition temperature and have excellent hole transport properties. A triphenylene ring structure is known as an example of a condensed ring having a high glass transition temperature (for example, Patent Documents 1 and 2). However, the luminous efficiency and device life of the organic EL device using the compound disclosed in Patent Document 1 cannot be said to be sufficient, and further improvements have been desired. Furthermore, in organic EL devices, the charge transport material constantly repeats redox for charge transport, but the 1-aminotriphenylene compound disclosed in Patent Document 2 has room for improvement in stability against redox. Ta.
本発明の目的は、従来公知のトリフェニレン化合物に比べて、酸化還元に対する安定性に優れる新規なトリフェニレン化合物、及び当該トリフェニレン化合物を用いた有機ＥＬ素子を提供することを目的とする。 An object of the present invention is to provide a novel triphenylene compound that has better stability against redox than conventionally known triphenylene compounds, and an organic EL device using the triphenylene compound.
本発明者らは鋭意検討した結果、下記一般式（１）で表されるトリフェニレン化合物が前記課題を解決することを見出し、本願発明を完成させるに至った。 As a result of extensive studies, the present inventors have found that a triphenylene compound represented by the following general formula (1) solves the above problems, and have completed the present invention.
（式中、Ａｒ１～Ａｒ３は、各々独立して、炭素数６～３０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３～２０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］を表す。
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。）
(In the formula, Ar 1 to Ar 3 are each independently a monocyclic, connected ring, or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monocyclic, connected ring having 3 to 20 carbon atoms, , or a fused-ring heteroaromatic group [each of these groups is independently a group consisting of a methyl group, a cyano group, a phenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group] may have one or more selected substituents].
L 1 and L 2 are each independently a single bond, or a monocyclic, connected ring, or fused ring divalent aromatic hydrocarbon group having 6 to 20 carbon atoms [these groups are each independently, Methyl group, ethyl group, straight chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group, ethoxy group, straight chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms, 1 to 18 carbon atoms 3, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, connected ring, or fused ring aryl group having 6 to 20 carbon atoms, a monocyclic ring, connected ring having 6 to 18 carbon atoms, or Aryloxy group with a condensed ring, monocyclic, connected ring, or heteroaryl group with fused rings having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, triarylsilyl group having 18 to 40 carbon atoms, cyano It may have one or more substituents selected from the group consisting of a group, a halogen atom, and a deuterium atom. ] represents.
R 1 to R 3 each independently represent a methyl group, methoxy group, or cyano group, n and m each independently represent an integer of 0 to 4, and p is an integer of 0 to 3. Represents an integer. )
本発明のトリフェニレン化合物は、その構造上の特徴に基づいて、酸化還元に対する安定性に優れるため、耐久性の高い正孔輸送材料を提供することができるという効果を奏する。即ち、耐久性の高い有機ＥＬ素子を提供することができるという効果を奏する。 The triphenylene compound of the present invention has excellent stability against redox based on its structural characteristics, and therefore has the effect of being able to provide a highly durable hole transport material. That is, it is possible to provide an organic EL element with high durability.
本発明のトリフェニレン化合物は、従来公知の材料に比べて、駆動電圧が低く、発光効率及び素子寿命に優れる有機ＥＬ素子を提供することができるという効果を奏する。 The triphenylene compound of the present invention has the effect of being able to provide an organic EL device with a lower driving voltage and excellent luminous efficiency and device life compared to conventionally known materials.
以下、本発明を詳細に説明する。 The present invention will be explained in detail below.
上記一般式（１）で表されるトリフェニレン化合物において、Ａｒ１～Ａｒ３は、各々独立して、炭素数６～３０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３～２０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］を表す。 In the triphenylene compound represented by the above general formula (1), Ar 1 to Ar 3 are each independently a monocyclic, connected ring, or fused ring aromatic hydrocarbon group having 6 to 30 carbon atoms, or a carbon Heteroaromatic group having 3 to 20 monocyclic rings, connected rings, or fused rings [These groups each independently include a methyl group, a cyano group, a phenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group may have one or more substituents selected from the group consisting of , and dibenzofuranyl group].
Ａｒ１～Ａｒ３における炭素数６～３０の単環、連結環、又は縮合環の芳香族炭化水素基としては、特に限定するものではないが、例えば、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、スピロビフルオレニル基、又はベンゾフルオレニル基等が挙げられる。なお、これらの基については、上述の通り、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、又はジベンゾフラニル基を有していてもよく、置換基の数については特に限定されない。 The monocyclic, connected ring, or condensed ring aromatic hydrocarbon group having 6 to 30 carbon atoms in Ar 1 to Ar 3 is not particularly limited, but includes, for example, a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group. group, naphthylphenyl group, fluorenyl group, phenanthryl group, phenanthrylphenyl group, spirobifluorenyl group, or benzofluorenyl group. Furthermore, as mentioned above, each of these groups may independently have a methyl group, a cyano group, a phenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, or a dibenzofuranyl group. , the number of substituents is not particularly limited.
Ａｒ１～Ａｒ３における炭素数３～２０の単環、連結環、又は縮合環のヘテロ芳香族基としては、特に限定するものではないが、例えば、少なくとも一つの酸素原子、窒素原子、又は硫黄原子を含有する炭素数３～２０の単環、連結環、又は縮合環のヘテロ芳香族基を挙げることができ、より好ましくは、酸素原子、窒素原子、及び硫黄原子からなる群より選ばれる原子を少なくとも一つ芳香環上に含有する炭素数３～２０の単環、連結環、又は縮合環のヘテロ芳香族基を挙げることができ、特に限定するものではないが、例えば、ピロリル基、チエニル基、フリル基、イミダゾリル基、ピラゾリル基、チアゾリル基、イソチアゾリル基、オキサゾリル基、イソオキサゾリル基、ピリジル基、ピリミジル基、ピラジル基、１，３，５－トリアジル基、インドリル基、ベンゾチエニル基、ベンゾフラニル基、ベンゾイミダゾリル基、インダゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基、２，１，３－ベンゾチアジアゾリル基、ベンゾオキサゾリル基、ベンゾイソオキサゾリル基、２，１，３－ベンゾオキサジアゾリル基、キノリル基、イソキノリル基、キノキサリル基、キナゾリル基、カルバゾリル基、ジベンゾチエニル基、ジベンゾフラニル基、フェノキサジニル基、フェノチアジニル基、フェナジン基、又はチアントレニル基等が挙げられる。なお、これらの基については、上述の通り、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、又はジベンゾフラニル基を有していてもよく、置換基の数については特に限定されない。 The monocyclic, connected ring, or condensed ring heteroaromatic group having 3 to 20 carbon atoms in Ar 1 to Ar 3 is not particularly limited, but includes, for example, at least one oxygen atom, nitrogen atom, or sulfur atom. Examples include monocyclic, connected ring, or fused ring heteroaromatic groups having 3 to 20 carbon atoms, and more preferably atoms selected from the group consisting of oxygen atoms, nitrogen atoms, and sulfur atoms. Examples include, but are not limited to, monocyclic, connected ring, or fused ring heteroaromatic groups having 3 to 20 carbon atoms containing at least one on the aromatic ring, such as pyrrolyl group, thienyl group, etc. group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, indolyl group, benzothienyl group, benzofuranyl group , benzimidazolyl group, indazolyl group, benzothiazolyl group, benzisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzisoxazolyl group, 2,1,3-benzoxadiazolyl group Examples include a lyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, a phenoxazinyl group, a phenothiazinyl group, a phenazine group, and a thianthrenyl group. Furthermore, as mentioned above, each of these groups may independently have a methyl group, a cyano group, a phenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, or a dibenzofuranyl group. , the number of substituents is not particularly limited.
Ａｒ１～Ａｒ３の具体例としては、特に限定するものではないが、各々独立して、フェニル基、４－メチルフェニル基、３－メチルフェニル基、２－メチルフェニル基、２，４－ジメチルフェニル基、２，５－ジメチルフェニル基、３，４－ジメチルフェニル基、３，５－ジメチルフェニル基、２，６－ジメチルフェニル基、２，３，５－トリメチルフェニル基、２，３，６－トリメチルフェニル基、３，４，５－トリメチルフェニル基、４－ビフェニリル基、３－ビフェニリル基、２－ビフェニリル基、２－メチル－１，１’－ビフェニル－４－イル基、３－メチル－１，１’－ビフェニル－４－イル基、２’－メチル－１，１’－ビフェニル－４－イル基、３’－メチル－１，１’－ビフェニル－４－イル基、４’－メチル－１，１’－ビフェニル－４－イル基、２，６－ジメチル－１，１’－ビフェニル－４－イル基、２，２’－ジメチル－１，１’－ビフェニル－４－イル基、２，３’－ジメチル－１，１’－ビフェニル－４－イル基、２，４’－ジメチル－１，１’－ビフェニル－４－イル基、３，２’－ジメチル－１，１’－ビフェニル－４－イル基、２’，３’－ジメチル－１，１’－ビフェニル－４－イル基、２’，４’－ジメチル－１，１’－ビフェニル－４－イル基、２’，５’－ジメチル－１，１’－ビフェニル－４－イル基、２’，６’－ジメチル－１，１’－ビフェニル－４－イル基、４－フェニルビフェニリル基、２－フェニルビフェニリル基、１－ナフチル基、２－ナフチル基、２－メチルナフタレン－１－イル基、４－メチルナフタレン－１－イル基、６－メチルナフタレン－２－イル基、４－（１－ナフチル）フェニル基、４－（２－ナフチル）フェニル基、３－（１－ナフチル）フェニル基、３－（２－ナフチル）フェニル基、３－メチル－４－（１－ナフチル）フェニル基、３－メチル－４－（２－ナフチル）フェニル基、４－（２－メチルナフタレン－１－イル）フェニル基、３－（２－メチルナフタレン－１－イル）フェニル基、４－フェニルナフタレン－１－イル基、４－（２－メチルフェニル）ナフタレン－１－イル基、４－（３－メチルフェニル）ナフタレン－１－イル基、４－（４－メチルフェニル）ナフタレン－１－イル基、６－フェニルナフタレン－２－イル基、４－（２－メチルフェニル）ナフタレン－２－イル基、４－（３－メチルフェニル）ナフタレン－２－イル基、４－（４－メチルフェニル）ナフタレン－２－イル基、テトラフェニルシラン－４－イル基、テトラフェニルシラン－３－イル基、２－フルオレニル基、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、９，９－ジフェニル－４－フルオレニル基、９，９’－スピロビフルオレニル基、９－フェナントリル基、２－フェナントリル基、１１，１１’－ジメチルベンゾ［ａ］フルオレン－９－イル基、１１，１１’－ジメチルベンゾ［ａ］フルオレン－３－イル基、１１，１１’－ジメチルベンゾ［ｂ］フルオレン－９－イル基、１１，１１’－ジメチルベンゾ［ｂ］フルオレン－３－イル基、１１，１１’－ジメチルベンゾ［ｃ］フルオレン－９－イル基、１１，１１’－ジメチルベンゾ［ｃ］フルオレン－２－イル基、３－フルオランテニル基、８－フルオランテニル基、１－イミダゾリル基、２－フェニル－１－イミダゾリル基、２－フェニル－３，４－ジメチル－１－イミダゾリル基、２，３，４－トリフェニル－１－イミダゾリル基、２－（２－ナフチル）－３，４－ジメチル－１－イミダゾリル基、２－（２－ナフチル）－３，４－ジフェニル－１－イミダゾリル基、１－メチル－２－イミダゾリル基、１－エチル－２－イミダゾリル基、１－フェニル－２－イミダゾリル基、１－メチル－４－フェニル－２－イミダゾリル基、１－メチル－４，５－ジメチル－２－イミダゾリル基、１－メチル－４，５－ジフェニル－２－イミダゾリル基、１－フェニル－４，５－ジメチル－２－イミダゾリル基、１－フェニル－４，５－ジフェニル－２－イミダゾリル基、１－フェニル－４，５－ジビフェニリル－２－イミダゾリル基、１－メチル－３－ピラゾリル基、１－フェニル－３－ピラゾリル基、１－メチル－４－ピラゾリル基、１－フェニル－４－ピラゾリル基、１－メチル－５－ピラゾリル基、１－フェニル－５－ピラゾリル基、２－チアゾリル基、４－チアゾリル基、５－チアゾリル基、３－イソチアゾリル基、４－イソチアゾリル基、５－イソチアゾリル基、２－オキサゾリル基、４－オキサゾリル基、５－オキサゾリル基、３－イソオキサゾリル基、４－イソオキサゾリル基、５－イソオキサゾリル基、２－ピリジル基、３－メチル－２－ピリジル基、４－メチル－２－ピリジル基、５－メチル－２－ピリジル基、６－メチル－２－ピリジル基、３－ピリジル基、４－メチル－３－ピリジル基、４－ピリジル基、２－ピリミジル基、２，２’－ビピリジン－３－イル基、２，２’－ビピリジン－４－イル基、２，２’－ビピリジン－５－イル基、２，３’－ビピリジン－３－イル基、２，３’－ビピリジン－４－イル基、２，３’－ビピリジン－５－イル基、５－ピリミジル基、ピラジル基、１，３，５－トリアジル基、４，６－ジフェニル－１，３，５－トリアジン－２－イル基、１－ベンゾイミダゾリル基、２－メチル－１－ベンゾイミダゾリル基、２－フェニル－１－ベンゾイミダゾリル基、１－メチル－２－ベンゾイミダゾリル基、１－フェニル－２－ベンゾイミダゾリル基、１－メチル－５－ベンゾイミダゾリル基、１，２－ジメチル－５－ベンゾイミダゾリル基、１－メチル－２－フェニル－５－ベンゾイミダゾリル基、１－フェニル－５－ベンゾイミダゾリル基、１，２－ジフェニル－５－ベンゾイミダゾリル基、１－メチル－６－ベンゾイミダゾリル基、１，２－ジメチル－６－ベンゾイミダゾリル基、１－メチル－２－フェニル－６－ベンゾイミダゾリル基、１－フェニル－６－ベンゾイミダゾリル基、１，２－ジフェニル－６－ベンゾイミダゾリル基、１－メチル－３－インダゾリル基、１－フェニル－３－インダゾリル基、２－ベンゾチアゾリル基、４－ベンゾチアゾリル基、５－ベンゾチアゾリル基、６－ベンゾチアゾリル基、７－ベンゾチアゾリル基、３－ベンゾイソチアゾリル基、４－ベンゾイソチアゾリル基、５－ベンゾイソチアゾリル基、６－ベンゾイソチアゾリル基、７－ベンゾイソチアゾリル基、２，１，３－ベンゾチアジアゾール－４－イル基、２，１，３－ベンゾチアジアゾール－５－イル基、２－ベンゾオキサゾリル基、４－ベンゾオキサゾリル基、５－ベンゾオキサゾリル基、６－ベンゾオキサゾリル基、７－ベンゾオキサゾリル基、３－ベンゾイソオキサゾリル基、４－ベンゾイソオキサゾリル基、５－ベンゾイソオキサゾリル基、６－ベンゾイソオキサゾリル基、７－ベンゾイソオキサゾリル基、２，１，３－ベンゾオキサジアゾリル－４－イル基、２，１，３－ベンゾオキサジアゾリル－５－イル基、２－キノリル基、３－キノリル基、５－キノリル基、６－キノリル基、１－イソキノリル基、４－イソキノリル基、５－イソキノリル基、２－キノキサリル基、３－フェニル－２－キノキサリル基、６－キノキサリル基、２，３－ジメチル－６－キノキサリル基、２，３－ジフェニル－６－キノキサリル基、２－キナゾリル基、４－キナゾリル基、２－アクリジニル基、９－アクリジニル基、１，１０－フェナントロリン－３－イル基、１，１０－フェナントロリン－５－イル基、２－チエニル基、３－チエニル基、２－ベンゾチエニル基、３－ベンゾチエニル基、２－ジベンゾチエニル基、４－ジベンゾチエニル基、２－フラニル基、３－フラニル基、２－ベンゾフラニル基、３－ベンゾフラニル基、２－ジベンゾフラニル基、４－ジベンゾフラニル基、９－メチルカルバゾール－２－イル基、９－メチルカルバゾール－３－イル基、９－メチルカルバゾール－４－イル基、９－フェニルカルバゾール－２－イル基、９－フェニルカルバゾール－３－イル基、９－フェニルカルバゾール－４－イル基、９－ビフェニリルカルバゾール－２－イル基、９－ビフェニリルカルバゾール－３－イル基、９－ビフェニリルカルバゾール－４－イル基、２－チアントリル基、１０－フェニルフェノチアジン－３－イル基、１０－フェニルフェノチアジン－２－イル基、１０－フェニルフェノキサジン－３－イル基、１０－フェニルフェノキサジン－２－イル基、１－メチルインドール－２－イル基、１－フェニルインドール－２－イル基、９－フェニルカルバゾール－４－イル基、１－メチルインドール－２－イル基、１－フェニルインドール－２－イル基、４－（２－ピリジル）フェニル基、４－（３－ピリジル）フェニル基、４－（４－ピリジル）フェニル基、３－（２－ピリジル）フェニル基、３－（３－ピリジル）フェニル基、３－（４－ピリジル）フェニル基、４－（２－フェニルイミダゾール－１－イル）フェニル基、４－（１－フェニルイミダゾール－２－イル）フェニル基、４－（２，３，４－トリフェニルイミダゾール－１－イル）フェニル基、４－（１－メチル－４，５－ジフェニルイミダゾール－２－イル）フェニル基、４－（２－メチルベンゾイミダゾール－１－イル）フェニル基、４－（２－フェニルベンゾイミダゾール－１－イル）フェニル基、４－（１－メチルベンゾイミダゾール－２－イル）フェニル基、４－（２－フェニルベンゾイミダゾール－１－イル）フェニル基、３－（２－メチルベンゾイミダゾール－１－イル）フェニル基、３－（２－フェニルベンゾイミダゾール－１－イル）フェニル基、３－（１－メチルベンゾイミダゾール－２－イル）フェニル基、３－（２－フェニルベンゾイミダゾール－１－イル）フェニル基、４－（３，５－ジフェニルトリアジン－１－イル）フェニル基、４－（２－チエニル）フェニル基、４－（２－フラニル）フェニル基、５－フェニルチオフェン－２－イル基、５－フェニルフラン－２－イル基、４－（５－フェニルチオフェン－２－イル）フェニル基、４－（５－フェニルフラン－２－イル）フェニル基、３－（５－フェニルチオフェン－２－イル）フェニル基、３－（５－フェニルフラン－２－イル）フェニル基、４－（２－ベンゾチエニル）フェニル基、４－（３－ベンゾチエニル）フェニル基、３－（２－ベンゾチエニル）フェニル基、３－（３－ベンゾチエニル）フェニル基、４－（２－ジベンゾチエニル）フェニル基、４－（４－ジベンゾチエニル）フェニル基、３－（２－ジベンゾチエニル）フェニル基、３－（４－ジベンゾチエニル）フェニル基、４－（２－ジベンゾフラニル）フェニル基、４－（４－ジベンゾフラニル）フェニル基、３－（２－ジベンゾフラニル）フェニル基、３－（４－ジベンゾフラニル）フェニル基、５－フェニルピリジン－２－イル基、４－フェニルピリジン－２－イル基、５－フェニルピリジン－３－イル基、４－（９－カルバゾリル）フェニル基、又は３－（９－カルバゾリル）フェニル基等を例示することができるが、これらに限定されるものではない。 Specific examples of Ar 1 to Ar 3 include, but are not particularly limited to, phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 2,4-dimethyl Phenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6 -trimethylphenyl group, 3,4,5-trimethylphenyl group, 4-biphenylyl group, 3-biphenylyl group, 2-biphenylyl group, 2-methyl-1,1'-biphenyl-4-yl group, 3-methyl- 1,1'-biphenyl-4-yl group, 2'-methyl-1,1'-biphenyl-4-yl group, 3'-methyl-1,1'-biphenyl-4-yl group, 4'-methyl -1,1'-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl-4-yl group, 2,2'-dimethyl-1,1'-biphenyl-4-yl group, 2,3'-dimethyl-1,1'-biphenyl-4-yl group, 2,4'-dimethyl-1,1'-biphenyl-4-yl group, 3,2'-dimethyl-1,1'- biphenyl-4-yl group, 2',3'-dimethyl-1,1'-biphenyl-4-yl group, 2',4'-dimethyl-1,1'-biphenyl-4-yl group, 2', 5'-dimethyl-1,1'-biphenyl-4-yl group, 2',6'-dimethyl-1,1'-biphenyl-4-yl group, 4-phenylbiphenylyl group, 2-phenylbiphenylyl group , 1-naphthyl group, 2-naphthyl group, 2-methylnaphthalen-1-yl group, 4-methylnaphthalen-1-yl group, 6-methylnaphthalen-2-yl group, 4-(1-naphthyl)phenyl group , 4-(2-naphthyl) phenyl group, 3-(1-naphthyl) phenyl group, 3-(2-naphthyl) phenyl group, 3-methyl-4-(1-naphthyl) phenyl group, 3-methyl-4 -(2-naphthyl)phenyl group, 4-(2-methylnaphthalen-1-yl)phenyl group, 3-(2-methylnaphthalen-1-yl)phenyl group, 4-phenylnaphthalen-1-yl group, 4 -(2-methylphenyl)naphthalen-1-yl group, 4-(3-methylphenyl)naphthalen-1-yl group, 4-(4-methylphenyl)naphthalen-1-yl group, 6-phenylnaphthalene-2 -yl group, 4-(2-methylphenyl)naphthalen-2-yl group, 4-(3-methylphenyl)naphthalen-2-yl group, 4-(4-methylphenyl)naphthalen-2-yl group, tetra Phenylsilan-4-yl group, tetraphenylsilan-3-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl- 4-fluorenyl group, 9,9'-spirobifluorenyl group, 9-phenanthryl group, 2-phenanthryl group, 11,11'-dimethylbenzo[a]fluoren-9-yl group, 11,11'-dimethyl Benzo[a]fluoren-3-yl group, 11,11'-dimethylbenzo[b]fluoren-9-yl group, 11,11'-dimethylbenzo[b]fluoren-3-yl group, 11,11'- Dimethylbenzo[c]fluoren-9-yl group, 11,11'-dimethylbenzo[c]fluoren-2-yl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 1-imidazolyl group, 2- Phenyl-1-imidazolyl group, 2-phenyl-3,4-dimethyl-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 2-(2-naphthyl)-3,4-dimethyl- 1-imidazolyl group, 2-(2-naphthyl)-3,4-diphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl group, 1-phenyl-2-imidazolyl group , 1-methyl-4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4, 5-dimethyl-2-imidazolyl group, 1-phenyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-diviphenyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1- Phenyl-3-pyrazolyl group, 1-methyl-4-pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-phenyl-5-pyrazolyl group, 2-thiazolyl group, 4- Thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5- Isoxazolyl group, 2-pyridyl group, 3-methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 3-pyridyl group, 4 -Methyl-3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 2,2'-bipyridin-3-yl group, 2,2'-bipyridin-4-yl group, 2,2'-bipyridin-5 -yl group, 2,3'-bipyridin-3-yl group, 2,3'-bipyridin-4-yl group, 2,3'-bipyridin-5-yl group, 5-pyrimidyl group, pyrazyl group, 1, 3,5-triazyl group, 4,6-diphenyl-1,3,5-triazin-2-yl group, 1-benzimidazolyl group, 2-methyl-1-benzimidazolyl group, 2-phenyl-1-benzimidazolyl group, 1 -Methyl-2-benzimidazolyl group, 1-phenyl-2-benzimidazolyl group, 1-methyl-5-benzimidazolyl group, 1,2-dimethyl-5-benzimidazolyl group, 1-methyl-2-phenyl-5-benzimidazolyl group, 1-phenyl-5-benzimidazolyl group, 1,2-diphenyl-5-benzimidazolyl group, 1-methyl-6-benzimidazolyl group, 1,2-dimethyl-6-benzimidazolyl group, 1-methyl-2-phenyl-6- Benzimidazolyl group, 1-phenyl-6-benzimidazolyl group, 1,2-diphenyl-6-benzimidazolyl group, 1-methyl-3-indazolyl group, 1-phenyl-3-indazolyl group, 2-benzothiazolyl group, 4-benzothiazolyl group , 5-benzothiazolyl group, 6-benzothiazolyl group, 7-benzothiazolyl group, 3-benzisothiazolyl group, 4-benzisothiazolyl group, 5-benzisothiazolyl group, 6-benzisothiazolyl group, 7- benzisothiazolyl group, 2,1,3-benzothiadiazol-4-yl group, 2,1,3-benzothiadiazol-5-yl group, 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl group, 7-benzoxazolyl group, 3-benzisoxazolyl group, 4-benzisoxazolyl group, 5-benzoisoxazolyl group , 6-benzisoxazolyl group, 7-benzisoxazolyl group, 2,1,3-benzoxadiazolyl-4-yl group, 2,1,3-benzoxadiazolyl-5-yl group , 2-quinolyl group, 3-quinolyl group, 5-quinolyl group, 6-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-quinoxalyl group, 3-phenyl-2-quinoxalyl group, 6-quinoxalyl group, 2,3-dimethyl-6-quinoxalyl group, 2,3-diphenyl-6-quinoxalyl group, 2-quinazolyl group, 4-quinazolyl group, 2-acridinyl group, 9-acridinyl group, 1,10 -phenanthrolin-3-yl group, 1,10-phenanthrolin-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzo Thienyl group, 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group, 9-methylcarbazol-2-yl group, 9-methyl Carbazol-3-yl group, 9-methylcarbazol-4-yl group, 9-phenylcarbazol-2-yl group, 9-phenylcarbazol-3-yl group, 9-phenylcarbazol-4-yl group, 9-biphenyl group Lylecarbazol-2-yl group, 9-biphenylylcarbazol-3-yl group, 9-biphenylylcarbazol-4-yl group, 2-thianthryl group, 10-phenylphenothiazin-3-yl group, 10-phenylphenothiazin-yl group 2-yl group, 10-phenylphenoxazin-3-yl group, 10-phenylphenoxazin-2-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 9-phenyl Carbazol-4-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 4-(2-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 4-( 4-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(2-phenylimidazol-1-yl)phenyl group, 4-(1-phenylimidazol-2-yl) phenyl group, 4-(2,3,4-triphenylimidazol-1-yl) phenyl group, 4-(1-methyl-4,5-diphenylimidazole) -2-yl)phenyl group, 4-(2-methylbenzimidazol-1-yl)phenyl group, 4-(2-phenylbenzimidazol-1-yl)phenyl group, 4-(1-methylbenzimidazol-2) -yl) phenyl group, 4-(2-phenylbenzimidazol-1-yl) phenyl group, 3-(2-methylbenzimidazol-1-yl) phenyl group, 3-(2-phenylbenzimidazol-1-yl) ) phenyl group, 3-(1-methylbenzimidazol-2-yl) phenyl group, 3-(2-phenylbenzimidazol-1-yl) phenyl group, 4-(3,5-diphenyltriazin-1-yl) Phenyl group, 4-(2-thienyl)phenyl group, 4-(2-furanyl)phenyl group, 5-phenylthiophen-2-yl group, 5-phenylfuran-2-yl group, 4-(5-phenylthiophene) -2-yl)phenyl group, 4-(5-phenylfuran-2-yl)phenyl group, 3-(5-phenylthiophen-2-yl)phenyl group, 3-(5-phenylfuran-2-yl) Phenyl group, 4-(2-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 3-(2-benzothienyl)phenyl group, 3-(3-benzothienyl)phenyl group, 4-( 2-dibenzothienyl) phenyl group, 4-(4-dibenzothienyl) phenyl group, 3-(2-dibenzothienyl) phenyl group, 3-(4-dibenzothienyl) phenyl group, 4-(2-dibenzofuranyl) Phenyl group, 4-(4-dibenzofuranyl) phenyl group, 3-(2-dibenzofuranyl) phenyl group, 3-(4-dibenzofuranyl) phenyl group, 5-phenylpyridin-2-yl group, 4 -Phenylpyridin-2-yl group, 5-phenylpyridin-3-yl group, 4-(9-carbazolyl)phenyl group, or 3-(9-carbazolyl)phenyl group, etc. It is not limited.
前記一般式（１）で表されるトリフェニレン化合物において、正孔輸送性に優れる点で、Ａｒ１～Ａｒ３は、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］であることが好ましく、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］であることがより好ましい。 In the triphenylene compound represented by the general formula (1), each of Ar 1 to Ar 3 independently represents a monocyclic ring, a connected ring, or a fused ring having 6 to 20 carbon atoms, since it has excellent hole transport properties. aromatic hydrocarbon group, or a monocyclic, connected ring, or fused ring heteroaromatic group having 3 to 16 carbon atoms [each of these groups independently represents a methyl group, a cyano group, a phenyl group, a triphenyl group] may have one or more substituents selected from the group consisting of a silyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group], each independently of a phenyl group, a biphenylyl group , terphenylyl group, naphthyl group, naphthylphenyl group, fluorenyl group, phenanthryl group, phenanthryl phenyl group, carbazolyl group, dibenzothienyl group, or dibenzofuranyl group [These groups each independently represent a methyl group, a cyano It is more preferable that the substituent group may have one or more substituents selected from the group consisting of a phenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.
上記の炭素数６～２０の単環、連結環、又は縮合環の芳香族炭化水素基としては、特に限定するものではないが、上記の炭素数６～３０の単環、連結環、又は縮合環の芳香族炭化水素基と同様の基（ただし、炭素数６～２０のものに限る）を例示することができる。 The above monocyclic, connected ring, or fused ring aromatic hydrocarbon group having 6 to 20 carbon atoms is not particularly limited, but the above monocyclic, connected ring, or fused ring having 6 to 30 carbon atoms is Groups similar to the ring aromatic hydrocarbon group (limited to those having 6 to 20 carbon atoms) can be exemplified.
上記の炭素数３～１６の単環、連結環、又は縮合環のヘテロ芳香族基としては、特に限定するものではないが、上記の炭素数３～２０の単環、連結環、又は縮合環のヘテロ芳香族基と同様の基（ただし、炭素数３～１６のものに限る）を例示することができる。 The above-mentioned monocyclic, connected ring, or fused ring heteroaromatic group having 3 to 16 carbon atoms is not particularly limited, but the above-mentioned monocyclic, connected ring, or fused ring having 3 to 20 carbon atoms is Groups similar to the heteroaromatic group (however, limited to those having 3 to 16 carbon atoms) can be exemplified.
また、前記一般式（１）で表されるトリフェニレン化合物において、正孔輸送性に優れる点で、Ａｒ１～Ａｒ３は、各々独立して、メチル基、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有していてもよいフェニル基、メチル基を有していてもよいビフェニリル基、メチル基を有していてもよいターフェニリル基、メチル基を有していてもよいナフチル基、メチル基を有していてもよいナフチルフェニル基、メチル基若しくはフェニル基を有していてもよいフルオレニル基、メチル基を有していてもよいフェナントリル基、メチル基を有していてもよいフェナントリルフェニル基、メチル基を有していてもよいジベンゾチエニル基、又はメチル基を有していてもよいジベンゾフラニル基であることがより好ましい。 Furthermore, in the triphenylene compound represented by the general formula (1), Ar 1 to Ar 3 each independently represent a methyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, in terms of excellent hole transport properties. and a phenyl group which may have a substituent selected from the group consisting of a dibenzofuranyl group, a biphenylyl group which may have a methyl group, a terphenylyl group which may have a methyl group, and a methyl group. Naphthyl group which may have a group, naphthylphenyl group which may have a methyl group, fluorenyl group which may have a methyl group or phenyl group, phenanthryl group which may have a methyl group , a phenanthryl phenyl group which may have a methyl group, a dibenzothienyl group which may have a methyl group, or a dibenzofuranyl group which may have a methyl group.
さらに、前記一般式（１）で表されるトリフェニレン化合物において、Ａｒ１～Ａｒ３は、正孔輸送性に優れる点で、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がさらに好ましい。 Furthermore, in the triphenylene compound represented by the general formula (1), Ar 1 to Ar 3 each independently represent a phenyl group, a 4-methylphenyl group, a 4-(9 -Carbazolyl)phenyl group, dibenzothienyl group, dibenzofuranyl group, 4-(4-dibenzothienyl)phenyl group, 4-(4-dibenzofuranyl)phenyl group, biphenylyl group, terphenylyl group, naphthyl group, 9,9 -dimethyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, or phenanthryl group is more preferable.
前記一般式（１）で表されるトリフェニレン化合物において、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。 In the triphenylene compound represented by the general formula (1), L 1 and L 2 are each independently a single bond, or a monocyclic, connected ring, or fused ring divalent aromatic group having 6 to 20 carbon atoms. Hydrocarbon group [These groups each independently include a methyl group, an ethyl group, a straight-chain, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight-chain, branched, or cyclic alkyl group having 3 to 18 carbon atoms; Chain, branched, or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, monocyclic, connected ring, or fused ring aryl group having 6 to 20 carbon atoms , a monocyclic, connected ring, or fused ring aryloxy group having 6 to 18 carbon atoms, a monocyclic, connected ring, or fused ring heteroaryl group having 3 to 20 carbon atoms, and a trialkylsilyl group having 3 to 18 carbon atoms. It may have one or more substituents selected from the group consisting of a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom. ] represents.
Ｌ１及びＬ２で示される、炭素数６～２０の単環、連結環、又は縮合環の２価芳香族炭化水素基の具体例としては、特に限定するものではないが、例えば、フェニレン基、ビフェニリレン基、ターフェニリレン基、ナフチレン基、フェニルナフタレン－ジイル基、ビナフチレン基、フルオレン－ジイル基、ベンゾフルオレン－ジイル基、ジベンゾフルオレン－ジイル基、フェナントレン－ジイル基、フルオランテン－ジイル基、アントラセン－ジイル基、クリセン－ジイル基、ピレン－ジイル基、トリフェニレン－ジイル基、又はペリレン－ジイル基等が挙げられる。 Specific examples of the monocyclic, connected ring, or condensed ring divalent aromatic hydrocarbon group having 6 to 20 carbon atoms represented by L 1 and L 2 are not particularly limited, but include, for example, a phenylene group. , biphenylylene group, terphenylylene group, naphthylene group, phenylnaphthalene-diyl group, binaphthylene group, fluorene-diyl group, benzofluorene-diyl group, dibenzofluorene-diyl group, phenanthrene-diyl group, fluoranthene-diyl group, anthracene-diyl group , chrysene-diyl group, pyrene-diyl group, triphenylene-diyl group, or perylene-diyl group.
炭素数３～１８の直鎖、分岐、又は環状のアルキル基としては、特に限定するものではないが、例えば、プロピル基、イソプロピル基、ブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ステアリル基、シクロプロピル基、又はシクロヘキシル基等が挙げられる。 The straight chain, branched, or cyclic alkyl group having 3 to 18 carbon atoms is not particularly limited, but includes, for example, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, and a pentyl group. , hexyl group, heptyl group, octyl group, stearyl group, cyclopropyl group, or cyclohexyl group.
炭素数３～１８の直鎖、分岐、又は環状のアルコキシ基としては、特に限定するものではないが、例えば、プロポキシ基、イソプロポキシ基、ｎ－ブトキシ基、ｓｅｃ－ブトキシ基、ｔｅｒｔ－ブトキシ基、ペンチルオキシ基、ヘキシルオキシ基、又はステアリルオキシ基等が挙げられる。 The straight chain, branched, or cyclic alkoxy group having 3 to 18 carbon atoms is not particularly limited, but includes, for example, a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a tert-butoxy group. , pentyloxy group, hexyloxy group, or stearyloxy group.
炭素数１～３のハロゲン化アルキル基としては、特に限定するものではないが、例えば、トリフルオロメチル基、トリクロロメチル基、又は２－フルオロエチル基等が挙げられる。 Examples of the halogenated alkyl group having 1 to 3 carbon atoms include, but are not limited to, a trifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, and the like.
炭素数１～３のハロゲン化アルコキシ基としては、特に限定するものではないが、例えば、トリフルオロメトキシ基、トリクロロメトキシ基、又は２－フルオロエトキシ基等が挙げられる。 Examples of the halogenated alkoxy group having 1 to 3 carbon atoms include, but are not limited to, a trifluoromethoxy group, a trichloromethoxy group, a 2-fluoroethoxy group, and the like.
炭素数６～２０の単環、連結環、又は縮合環のアリール基は、特に限定するものではないが、総炭素数６～２０の置換基を有していてもよい単環、連結環、又は縮合環の芳香族炭化水素基であることが好ましく、該基としては、特に限定するものではないが、例えば、フェニル基、２－メチルフェニル基、３－メチルフェニル基、４－メチルフェニル基、２－メトキシフェニル基、３－メトキシフェニル基、４－メトキシフェニル基、２－シアノフェニル基、３－シアノフェニル基、４－シアノフェニル基、３，４－ジメチルフェニル基、２，６－ジメチルフェニル基、ビフェニリル基、ナフチル基、１－メチルナフチル基、２－メチルナフチル基、１－メトキシナフチル基、２－メトキシナフチル基、又は９，９－ジメチルフルオレニル基等が挙げられる。 A monocyclic, connected ring, or fused ring aryl group having 6 to 20 carbon atoms is not particularly limited, but may include a monocyclic ring, a connected ring, which may have a substituent having a total of 6 to 20 carbon atoms, or a condensed ring aromatic hydrocarbon group, examples of which include, but are not limited to, phenyl, 2-methylphenyl, 3-methylphenyl, and 4-methylphenyl groups. , 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,4-dimethylphenyl group, 2,6-dimethyl Examples include phenyl group, biphenylyl group, naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, 1-methoxynaphthyl group, 2-methoxynaphthyl group, and 9,9-dimethylfluorenyl group.
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は、特に限定するものではないが、総炭素数６～１８の置換基を有していてもよい単環、連結環、又は縮合環の芳香族オキシ基であることが好ましく、該基としては、特に限定するものではないが、例えば、フェノキシ基、２－メチルフェノキシ基、３－メチルフェノキシ基、４－メチルフェノキシ基、２－メトキシフェノキシ基、３－メトキシフェノキシ基、４－メトキシフェノキシ基、２－シアノフェノキシ基、３－シアノフェノキシ基、４－シアノフェノキシ基、３，４－ジメチルフェノキシ基、２，６－ジメチルフェノキシ基、ビフェニルオキシ基、又はナフチルオキシ基等が挙げられる。 A monocyclic, connected ring, or condensed ring aryloxy group having 6 to 18 carbon atoms is not particularly limited, but may be a monocyclic, connected ring, which may have a substituent having a total of 6 to 18 carbon atoms. or a condensed ring aromatic oxy group, examples of which include, but are not limited to, phenoxy, 2-methylphenoxy, 3-methylphenoxy, and 4-methylphenoxy groups. , 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4-methoxyphenoxy group, 2-cyanophenoxy group, 3-cyanophenoxy group, 4-cyanophenoxy group, 3,4-dimethylphenoxy group, 2,6-dimethyl Examples include phenoxy group, biphenyloxy group, and naphthyloxy group.
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は、特に限定するものではないが、総炭素数３～２０の置換基を有していてもよい単環、連結環、又は縮合環のヘテロ芳香族基であることが好ましく、該基としては、特に限定するものではないが、例えば、ピロリル基、１－メチルピロリル基、１－フェニルピロリル基、チエニル基、２－メチルチエニル基、２－シアノチエニル基、２－フェニルチエニル基、フリル基、２－フェニルフリル基、イミダゾリル基、１－メチルイミダゾリル基、２－メチルイミダゾリル基、１－フェニルイミダゾリル基、２－フェニル－イミダゾリル基、ピラゾリル基、チアゾリル基、イソチアゾリル基、オキサゾリル基、イソオキサゾリル基、ピリジル基、ピリミジル基、ピラジル基、１，３，５－トリアジル基、２，４－ジフェニル－１，３，５－トリアジル基、インドリル基、ベンゾチエニル基、ベンゾフラニル基、ベンゾイミダゾリル基、２－メチルベンゾイミダゾリル基、２－フェニルベンゾイミダゾリル基、１－メチルベンゾイミダゾリル基、１－フェニルベンゾイミダゾリル基、１，２－ジフェニルベンゾイミダゾリル基、インダゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基、２，１，３－ベンゾチアジアゾリル基、ベンゾオキサゾリル基、ベンゾイソオキサゾリル基、２，１，３－ベンゾオキサジアゾリル基、キノリル基、イソキノリル基、キノキサリル基、キナゾリル基、カルバゾリル基、９－メチルカルバゾリル基、９－エチルカルバゾリル基、９－フェニルカルバゾリル基、ジベンゾチエニル基、ジベンゾフラニル基、フェノキサジニル基、フェノチアジニル基、アクリジニル基、フェナントロリン基、フェナジン基、又はチアントレニル基等が挙げられる。 A monocyclic, connected ring, or fused ring heteroaryl group having 3 to 20 carbon atoms is not particularly limited, but may be a monocyclic ring or connected ring that may have a substituent having a total of 3 to 20 carbon atoms. or a condensed ring heteroaromatic group, examples of which include, but are not limited to, a pyrrolyl group, a 1-methylpyrrolyl group, a 1-phenylpyrrolyl group, a thienyl group, a 2- Methylthienyl group, 2-cyanothienyl group, 2-phenylthienyl group, furyl group, 2-phenylfuryl group, imidazolyl group, 1-methylimidazolyl group, 2-methylimidazolyl group, 1-phenylimidazolyl group, 2-phenyl- imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, 2,4-diphenyl-1,3,5-triazyl group , indolyl group, benzothienyl group, benzofuranyl group, benzimidazolyl group, 2-methylbenzimidazolyl group, 2-phenylbenzimidazolyl group, 1-methylbenzimidazolyl group, 1-phenylbenzimidazolyl group, 1,2-diphenylbenzimidazolyl group, indazolyl group, benzothiazolyl group group, benzisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzisoxazolyl group, 2,1,3-benzoxadiazolyl group, quinolyl group, isoquinolyl group , quinoxalyl group, quinazolyl group, carbazolyl group, 9-methylcarbazolyl group, 9-ethylcarbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, dibenzofuranyl group, phenoxazinyl group, phenothiazinyl group, Examples include an acridinyl group, a phenanthroline group, a phenazine group, and a thianthrenyl group.
炭素数３～１８のトリアルキルシリル基としては、特に限定するものではないが、例えば、トリメチルシリル基、トリエチルシリル基、又はトリブチルシリル基等が挙げられる。 The trialkylsilyl group having 3 to 18 carbon atoms is not particularly limited, but includes, for example, a trimethylsilyl group, a triethylsilyl group, a tributylsilyl group, and the like.
炭素数１８～４０のトリアリールシリル基としては、特に限定するものではないが、例えば、トリフェニルシリル基、トリ（２－メチルフェニル）シリル基、トリ（３－メチルフェニル）シリル基、トリ（４－メチルフェニル）シリル基、又はトリ（４－ビフェニリル）シリル基等が挙げられる。 The triarylsilyl group having 18 to 40 carbon atoms is not particularly limited, but includes, for example, triphenylsilyl group, tri(2-methylphenyl)silyl group, tri(3-methylphenyl)silyl group, tri( Examples include 4-methylphenyl)silyl group and tri(4-biphenylyl)silyl group.
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、又はヨウ素原子が挙げられる。 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
前記一般式（１）で表されるトリフェニレン化合物において、正孔輸送性に優れる点で、Ｌ１及びＬ２は、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。］であることが好ましい。 In the triphenylene compound represented by the general formula (1), L 1 and L 2 each independently represent a single bond, a monocyclic ring having 6 to 14 carbon atoms, or a connected ring in terms of excellent hole transport properties. , or a condensed ring divalent aromatic hydrocarbon group [These groups each independently include a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic ring having 6 to 20 carbon atoms, Aryl group of connected ring or condensed ring, aryloxy group of monocycle, connected ring or condensed ring having 6 to 18 carbon atoms, heteroaryl group of monocycle, connected ring or condensed ring having 3 to 20 carbon atoms, It may have one or more substituents selected from the group consisting of a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom. . ] is preferable.
上記の炭素数６～１４の単環、連結環、又は縮合環の２価芳香族炭化水素基としては、特に限定するものではないが、上記の炭素数６～２０の単環、連結環、又は縮合環の２価芳香族炭化水素基と同様の基（ただし、炭素数６～１４のものに限る）を例示することができる。 The above-mentioned monocyclic, connected ring, or condensed ring divalent aromatic hydrocarbon group having 6 to 14 carbon atoms is not particularly limited; Alternatively, a group similar to a condensed ring divalent aromatic hydrocarbon group (limited to those having 6 to 14 carbon atoms) can be exemplified.
また、Ｌ１及びＬ２は、正孔輸送性に優れる点で、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（これらの基は、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）であることが好ましく、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がより好ましく、各々独立して、単結合、１，３－フェニレン基、１，４－フェニレン基、３，４’－ビフェニリレン基、又は４，４’－ビフェニリレン基であることがより好ましく、各々独立して、単結合、１，３－フェニレン基、又は１，４－フェニレン基であることがさらに好ましい。 In addition, L 1 and L 2 each independently represent a single bond, a phenylene group, or a biphenylylene group (these groups include a methyl group, an ethyl group, and a straight carbon number group of 3 to 18) because of their excellent hole transport properties. Chain, branched, or cyclic alkyl group, methoxy group, ethoxy group, straight chain, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, halogenated alkyl group having 1 to 3 carbon atoms, and halogenated alkyl group having 1 to 3 carbon atoms. Halogenated alkoxy group, monocyclic, connected ring, or fused ring aryl group having 6 to 20 carbon atoms; monocyclic, connected ring, or fused ring aryloxy group having 6 to 18 carbon atoms; From the group consisting of a monocyclic, connected ring, or fused ring heteroaryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom (which may have one or more selected substituents), each independently is more preferably a single bond, a phenylene group, or a biphenylylene group, each independently a single bond, More preferably, they are a 1,3-phenylene group, a 1,4-phenylene group, a 3,4'-biphenylylene group, or a 4,4'-biphenylylene group, each of which independently represents a single bond, 1,3-phenylene More preferably, it is a group or a 1,4-phenylene group.
前記一般式（１）で表されるトリフェニレン化合物において、Ｒ１～Ｒ３は、各々独立して、メチル基、メトキシ基、又はシアノ基を表す。正孔輸送性に優れる点で、Ｒ１～Ｒ３は、各々独立して、メチル基、又はシアノ基であることが好ましい。 In the triphenylene compound represented by the general formula (1), R 1 to R 3 each independently represent a methyl group, a methoxy group, or a cyano group. From the viewpoint of excellent hole transport properties, each of R 1 to R 3 is preferably independently a methyl group or a cyano group.
ｎ、及びｍは、各々独立して、０～４の整数を表す。ｐは、０～３の整数を表す。正孔輸送性に優れる点で、ｎ、ｍ及びｐ、各々独立して、０、１、２、又は３であることが好ましく、０、１、又は２であることがより好ましく、０、又は１であることがより好ましく、０であることがより好ましい。 n and m each independently represent an integer of 0 to 4. p represents an integer from 0 to 3. In terms of excellent hole transport properties, n, m and p are each independently preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, and 0 or It is more preferably 1, and even more preferably 0.
以下に、一般式（１）で表されるトリフェニレン化合物について、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。 Preferred examples of the triphenylene compound represented by the general formula (1) are shown below, but the present invention is not limited to these compounds.
前記一般式（１）で表されるトリフェニレン化合物は、例えばハロゲン化トリフェニレン化合物を原料として用い、公知の方法（アリールアミノ化）によって合成することができる。例えば、下記一般式（２）で表される１－ハロゲン化トリフェニレン化合物と、一般式（３）で表される二級アミン化合物とを、塩基の存在下、銅触媒又はパラジウム触媒を用いて反応させることで、一般式（１）で表されるトリフェニレン化合物を得ることができる。 The triphenylene compound represented by the general formula (1) can be synthesized by a known method (arylamination) using, for example, a halogenated triphenylene compound as a raw material. For example, a 1-halogenated triphenylene compound represented by the following general formula (2) and a secondary amine compound represented by the general formula (3) are reacted using a copper catalyst or a palladium catalyst in the presence of a base. By doing so, a triphenylene compound represented by general formula (1) can be obtained.
また、一般式（２）で表されるトリフェニレン化合物と、一般式（４）で表される一級アミン化合物とを、塩基の存在下、銅触媒又はパラジウム触媒を用いて反応させることで、一般式（５）で表される二級アミン化合物が得られる。得られた一般式（５）で表される二級アミン化合物と、一般式（６）で表されるハロゲン原子を有するアミン化合物とを、塩基の存在下、銅触媒又はパラジウム触媒を用いて反応させることで、一般式（１）で表されるトリフェニレン化合物を得ることができる。 Further, by reacting the triphenylene compound represented by the general formula (2) with the primary amine compound represented by the general formula (4) using a copper catalyst or a palladium catalyst in the presence of a base, the general formula A secondary amine compound represented by (5) is obtained. The obtained secondary amine compound represented by the general formula (5) and the amine compound having a halogen atom represented by the general formula (6) are reacted in the presence of a base using a copper catalyst or a palladium catalyst. By doing so, a triphenylene compound represented by general formula (1) can be obtained.
［式（２）、（３）、（４）、（５）、及び（６）中、Ｒ１～Ｒ３、Ａｒ１～Ａｒ３、Ｌ１、Ｌ２、ｍ、ｎ、及びｐは、前記一般式（１）と同じ定義を表す。Ｘ及びＹは、各々独立して、ハロゲン原子（ヨウ素、臭素、塩素、又はフッ素）又はトリフラート基を表す。］
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。
[In formulas (2), (3), (4), (5), and (6), R 1 to R 3 , Ar 1 to Ar 3 , L 1 , L 2 , m, n, and p are It represents the same definition as the general formula (1) above. X and Y each independently represent a halogen atom (iodine, bromine, chlorine, or fluorine) or a triflate group. ]
Further, the 1-halogenated triphenylene compound represented by the general formula (2) can be synthesized by a known method (Organic Letters, 2018, Vol. 20, p. 5402).
本発明の前記一般式（１）で表されるトリフェニレン化合物は、有機ＥＬ素子用材料として使用することができ、より具体的には、有機ＥＬ素子の発光層、正孔輸送層、又は正孔注入層として使用することができる。なお、前記一般式（１）で表されるトリフェニレン化合物は、正孔輸送特性や素子寿命の点で、高純度であることが好ましい。具体的には、ハロゲン原子や遷移金属元素による不純物や、製造原料や副生成物等の不純物が極力少ないものが好ましい。 The triphenylene compound represented by the general formula (1) of the present invention can be used as a material for an organic EL device, and more specifically, the triphenylene compound represented by the general formula (1) can be used as a material for an organic EL device. Can be used as injection layer. Note that the triphenylene compound represented by the general formula (1) is preferably highly pure in terms of hole transport properties and device life. Specifically, it is preferable that the amount of impurities such as halogen atoms, transition metal elements, manufacturing raw materials, by-products, etc. is as small as possible.
前記一般式（１）で表されるトリフェニレン化合物を有機ＥＬ素子の正孔注入層又は正孔輸送層として使用する際の発光層には、従来から使用されている公知の蛍光又は燐光発光材料、又は熱活性化遅延蛍光材料を使用することができる。発光層は１種類の発光材料のみで形成されていても、ホスト材料中に１種類以上の発光材料がドープされていてもよい。 When the triphenylene compound represented by the general formula (1) is used as a hole injection layer or a hole transport layer of an organic EL device, the light emitting layer may include conventionally used fluorescent or phosphorescent materials, Alternatively, thermally activated delayed fluorescent materials can be used. The light-emitting layer may be formed of only one type of light-emitting material, or the host material may be doped with one or more types of light-emitting material.
前記一般式（１）で表されるトリフェニレン化合物を含む正孔注入層及び／又は正孔輸送層を形成する際には、必要に応じて２種類以上の材料を含有又は積層させてもよく、例えば、酸化モリブデン等の酸化物、７，７，８，８－テトラシアノキノジメタン、２，３，５，６－テトラフルオロ－７，７，８，８－テトラシアノキノジメタン、ヘキサシアノヘキサアザトリフェニレン等の公知の電子受容性材料を含有又は積層させてもよい。 When forming the hole injection layer and/or hole transport layer containing the triphenylene compound represented by the general formula (1), two or more types of materials may be included or laminated as necessary, For example, oxides such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, hexacyanoquinodimethane, etc. A known electron-accepting material such as azatriphenylene may be contained or laminated.
また、本発明の前記一般式（１）で表されるトリフェニレン化合物は、有機ＥＬ素子の発光層としても使用することができる。前記一般式（１）で表されるトリフェニレン化合物を有機ＥＬ素子の発光層として使用する場合には、トリフェニレン化合物を単独で使用、公知の発光ホスト材料にドープして使用、又は公知の発光ドーパントをドープして使用することができる。 Further, the triphenylene compound represented by the general formula (1) of the present invention can also be used as a light emitting layer of an organic EL device. When using the triphenylene compound represented by the general formula (1) as a light-emitting layer of an organic EL device, the triphenylene compound may be used alone, doped into a known light-emitting host material, or used with a known light-emitting dopant. Can be doped and used.
前記一般式（１）で表されるトリフェニレン化合物を含有する正孔注入層、正孔輸送層又は発光層を形成する方法としては、例えば、真空蒸着法、スピンコート法、キャスト法等の公知の方法を適用することができる。 As a method for forming a hole injection layer, a hole transport layer, or a light emitting layer containing the triphenylene compound represented by the general formula (1), for example, a known method such as a vacuum evaporation method, a spin coating method, or a casting method can be used. method can be applied.
本発明の効果が得られる有機ＥＬ素子の基本的な構造としては、基板、陽極、正孔注入層、正孔輸送層、発光層、電子輸送層、及び陰極を含むものが好ましく、一部の層が省略されていても、また逆に追加されていてもよい。 The basic structure of an organic EL device that can obtain the effects of the present invention preferably includes a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode. Layers may be omitted or added.
有機ＥＬ素子の陽極及び陰極は、電気的な導体を介して電源に接続されている。陽極と陰極との間に電位を加えることにより、有機ＥＬ素子は作動、発光する。 The anode and cathode of the organic EL element are connected to a power source via an electrical conductor. By applying a potential between the anode and the cathode, the organic EL element operates and emits light.
正孔は陽極から有機ＥＬ素子内に注入され、電子は陰極で有機ＥＬ素子内に注入される。 Holes are injected into the organic EL element from the anode, and electrons are injected into the organic EL element from the cathode.
有機ＥＬ素子は典型的には基板に被せられ、陽極又は陰極は基板と接触することができる。基板と接触する電極は便宜上、下側電極と呼ばれる。一般的には、下側電極は陽極であるが、本発明の有機ＥＬ素子においては、そのような形態に限定されるものではない。 Organic EL devices are typically placed over a substrate, and an anode or a cathode can be in contact with the substrate. The electrode in contact with the substrate is conveniently referred to as the lower electrode. Generally, the lower electrode is an anode, but the organic EL element of the present invention is not limited to such a form.
基板は、意図される発光方向に応じて、光透過性又は不透明であってもよい。光透過特性は、基板を通してエレクトロルミネッセンス発光により確認できる。一般的には、透明ガラス又はプラスチックがこのような場合に基板として採用される。基板は、多重の材料層を含む複合構造であってもよい。 The substrate may be optically transparent or opaque, depending on the intended direction of light emission. The light transmission properties can be confirmed by electroluminescence emission through the substrate. Generally, transparent glass or plastic is employed as the substrate in such cases. The substrate may be a composite structure including multiple layers of materials.
エレクトロルミネッセンス発光を、陽極を通して確認する場合、陽極は当該発光を通すか又は実質的に通すもので形成される。 If the electroluminescent emission is observed through an anode, the anode is formed to be transparent or substantially transparent to the emission.
本発明において使用される一般的な透明アノード（陽極）材料は、特に限定するものではないが、インジウム－錫酸化物（ＩＴＯ）、インジウム－亜鉛酸化物（ＩＺＯ）、又は酸化錫等が挙げられる。その他の金属酸化物、例えばアルミニウム又はインジウム・ドープ型酸化錫、マグネシウム－インジウム酸化物、又はニッケル－タングステン酸化物も使用可能である。これらの酸化物に加えて、金属窒化物である、例えば窒化ガリウム、金属セレン化物である、例えばセレン化亜鉛、又は金属硫化物である、例えば硫化亜鉛を陽極として使用することができる。 Common transparent anode materials used in the present invention include, but are not limited to, indium-tin oxide (ITO), indium-zinc oxide (IZO), or tin oxide. . Other metal oxides can also be used, such as aluminum or indium doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide. In addition to these oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, or metal sulfides such as zinc sulfide can be used as anodes.
陽極は、プラズマ蒸着されたフルオロカーボンで改質することができる。陰極を通してだけエレクトロルミネッセンス発光が確認される場合、陽極の透過特性は重要ではなく、透明、不透明又は反射性の任意の導電性材料を使用することができる。この用途のための導体の一例としては、金、イリジウム、モリブデン、パラジウム、白金等が挙げられる。 The anode can be modified with plasma deposited fluorocarbons. If electroluminescent emission is seen only through the cathode, the transmission properties of the anode are not important and any conductive material, transparent, opaque or reflective, can be used. Examples of conductors for this application include gold, iridium, molybdenum, palladium, platinum, and the like.
陽極と発光層の間には、正孔注入層や正孔輸送層といった正孔輸送性の層を複数層設けることができる。正孔注入層や正孔輸送層は、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、これらの層を陽極と発光層の間に介在させることにより、より低い電界で多くの正孔を発光層に注入することができる。 A plurality of hole-transporting layers such as a hole-injection layer and a hole-transporting layer can be provided between the anode and the light-emitting layer. The hole injection layer and hole transport layer have the function of transmitting holes injected from the anode to the light emitting layer, and by interposing these layers between the anode and the light emitting layer, more holes can be transferred with a lower electric field. holes can be injected into the light emitting layer.
本発明の有機ＥＬ素子において、正孔輸送層及び／又は正孔注入層は、前記一般式（１）で表されるトリフェニレン化合物を含むものである。 In the organic EL device of the present invention, the hole transport layer and/or the hole injection layer contain a triphenylene compound represented by the general formula (1).
正孔輸送層及び／又は正孔注入層には、前記一般式（１）で表されるトリフェニレン化合物と共に、公知の正孔輸送材料及び／又は正孔注入材料の中から任意のものを選択して組み合わせて用いることができる。 In addition to the triphenylene compound represented by the general formula (1), any material selected from known hole transport materials and/or hole injection materials can be used for the hole transport layer and/or the hole injection layer. Can be used in combination.
公知の正孔注入材料、正孔輸送材料としては、例えばトリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体及びピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、アニリン系共重合体、又、導電性高分子オリゴマー、特にチオフェンオリゴマーなどが挙げられる。正孔注入材料、正孔輸送材料としては、上記のものを使用することができるが、ポルフィリン化合物、芳香族第三級アミン化合物及びスチリルアミン化合物、特に芳香族第三級アミン化合物を用いることが好ましい。 Known hole injection materials and hole transport materials include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, Examples include oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, especially thiophene oligomers. As the hole injection material and the hole transport material, the above materials can be used, but porphyrin compounds, aromatic tertiary amine compounds and styryl amine compounds, especially aromatic tertiary amine compounds can be used. preferable.
上記芳香族第三級アミン化合物及びスチリルアミン化合物の代表例としては、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラフェニル－４，４’－ジアミノフェニル、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ビス（３－メチルフェニル）－〔１，１’－ビフェニル〕－４，４’－ジアミン（ＴＰＤ）、２，２－ビス（４－ジ－ｐ－トリルアミノフェニル）プロパン、１，１－ビス（４－ジ－ｐ－トリルアミノフェニル）シクロヘキサン、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラ－ｐ－トリル－４，４’－ジアミノビフェニル、１，１－ビス（４－ジ－ｐ－トリルアミノフェニル）－４－フェニルシクロヘキサン、ビス（４－ジメチルアミノ－２－メチルフェニル）フェニルメタン、ビス（４－ジ－ｐ－トリルアミノフェニル）フェニルメタン、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ジ（４－メトキシフェニル）－４，４’－ジアミノビフェニル、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラフェニル－４，４’－ジアミノジフェニルエーテル、４，４’－ビス（ジフェニルアミノ）クオードリフェニル、Ｎ，Ｎ，Ｎ－トリ（ｐ－トリル）アミン、４－（ジ－ｐ－トリルアミノ）－４’－〔４－（ジ－ｐ－トリルアミノ）スチリル〕スチルベン、４－Ｎ，Ｎ－ジフェニルアミノ－（２－ジフェニルビニル）ベンゼン、３－メトキシ－４’－Ｎ，Ｎ－ジフェニルアミノスチルベンゼン、Ｎ－フェニルカルバゾール、４，４’－ビス〔Ｎ－（１－ナフチル）－Ｎ－フェニルアミノ〕ビフェニル（ＮＰＤ）、４，４’，４’’－トリス〔Ｎ－（３－メチルフェニル）－Ｎ－フェニルアミノ〕トリフェニルアミン（ＭＴＤＡＴＡ）などがあげられる。 Representative examples of the aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N' -Bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1- Bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p- tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N '-di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)chloride Odriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N- Diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenyl Examples include amino]biphenyl (NPD), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and the like.
又、ｐ型－Ｓｉ、ｐ型－ＳｉＣなどの無機化合物も正孔注入材料、正孔輸送材料として使用することができる。正孔注入層、正孔輸送層は、上記材料の一種又は二種以上からなる一層構造であってもよく、同一組成又は異種組成の複数層からなる積層構造であってもよい。 Inorganic compounds such as p-type Si and p-type SiC can also be used as hole injection materials and hole transport materials. The hole injection layer and the hole transport layer may have a single layer structure made of one or more of the above materials, or may have a laminated structure made of a plurality of layers having the same composition or different compositions.
有機ＥＬ素子の発光層は、燐光材料又は蛍光材料を含み、この領域で電子・正孔対が再結合された結果として発光を生ずる。 The light-emitting layer of an organic EL device contains a phosphorescent or fluorescent material, and emits light as a result of recombination of electron-hole pairs in this region.
発光層は、低分子及びポリマー双方を含む単一材料から成っていてもよいが、より一般的には、ゲスト化合物でドーピングされたホスト材料から成っており、発光は主としてドーパントから生じ、任意の色を有することができる。 The emissive layer may consist of a single material, including both small molecules and polymers, but more commonly it consists of a host material doped with a guest compound, with the emission primarily coming from the dopant and any Can have color.
発光層のホスト材料としては、例えば、ビフェニル基、フルオレニル基、トリフェニルシリル基、カルバゾール基、ピレニル基、又はアントラニル基を有する化合物が挙げられる。例えば、ＤＰＶＢｉ（４，４’－ビス（２，２－ジフェニルビニル）－１，１’－ビフェニル）、ＢＣｚＶＢｉ（４，４’－ビス（９－エチル－３－カルバゾビニレン）１，１’－ビフェニル）、ＴＢＡＤＮ（２－ターシャルブチル－９，１０－ジ（２－ナフチル）アントラセン）、ＡＤＮ（９，１０－ジ（２－ナフチル）アントラセン）、ＣＢＰ（４，４’－ビス（カルバゾール－９－イル）ビフェニル）、ＣＤＢＰ（４，４’－ビス（カルバゾール－９－イル）－２，２’－ジメチルビフェニル）、又は９，１０－ビス（ビフェニル）アントラセン等が挙げられる。 Examples of the host material for the light-emitting layer include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthranyl group. For example, DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)1,1'-biphenyl) ), TBADN (2-tert-butyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazole-9) -yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), or 9,10-bis(biphenyl)anthracene.
発光層内のホスト材料としては、下記に定義する電子輸送材料、上記に定義する正孔輸送材料、正孔・電子再結合を助ける（サポート）別の材料、又はこれら材料の組み合わせであってもよい。 The host material in the light-emitting layer may be an electron transport material defined below, a hole transport material defined above, another material that assists in hole/electron recombination (support), or a combination of these materials. good.
蛍光ドーパントの一例としては、アントラセン、ピレン、テトラセン、キサンテン、ペリレン、ルブレン、クマリン、ローダミン、キナクリドン、ジシアノメチレンピラン化合物、チオピラン化合物、ポリメチン化合物、ピリリウム又はチアピリリウム化合物、フルオレン誘導体、ペリフランテン誘導体、インデノペリレン誘導体、ビス（アジニル）アミンホウ素化合物、ビス（アジニル）メタン化合物、カルボスチリル化合物等が挙げられる。 Examples of fluorescent dopants include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium or thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, indenoperylene Examples include derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyril compounds, and the like.
燐光ドーパントの一例としては、イリジウム、白金、パラジウム、オスミウム等の遷移金属の有機金属錯体が挙げられる。 Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.
ドーパントの一例として、Ａｌｑ３（トリス（８－ヒドロキシキノリン）アルミニウム））、ＤＰＡＶＢｉ（４，４’－ビス［４－（ジ－ｐ－トリルアミノ）スチリル］ビフェニル）、ペリレン、Ｉｒ（ＰＰｙ）３（トリス（２－フェニルピリジン）イリジウム（ＩＩＩ）、又はＦｌｒＰｉｃ（ビス（３，５－ジフルオロ－２－（２－ピリジル）フェニル－（２－カルボキシピリジル）イリジウム（ＩＩＩ）等が挙げられる。 Examples of dopants include Alq 3 (tris(8-hydroxyquinoline)aluminum)), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, Ir(PPy) 3 ( Examples include tris(2-phenylpyridine)iridium(III), or FlrPic(bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III)).
電子輸送性材料としては、アルカリ金属錯体、アルカリ土類金属錯体、土類金属錯体等が挙げられる。アルカリ金属錯体、アルカリ土類金属錯体、又は土類金属錯体としては、例えば、８－ヒドロキシキノリナートリチウム（Ｌｉｑ）、ビス（８－ヒドロキシキノリナート）亜鉛、ビス（８－ヒドロキシキノリナート）銅、ビス（８－ヒドロキシキノリナート）マンガン、トリス（８－ヒドロキシキノリナート）アルミニウム、トリス（２－メチル－８－ヒドロキシキノリナート）アルミニウム、トリス（８－ヒドロキシキノリナート）ガリウム、ビス（１０－ヒドロキシベンゾ［ｈ］キノリナート）ベリリウム、ビス（１０－ヒドロキシベンゾ［ｈ］キノリナート）亜鉛、ビス（２－メチル－８－キノリナート）クロロガリウム、ビス（２－メチル－８－キノリナート）（ｏ－クレゾラート）ガリウム、ビス（２－メチル－８－キノリナート）－１－ナフトラートアルミニウム、ビス（２－メチル－８－キノリナート）－２－ナフトラートガリウム等が挙げられる。 Examples of the electron-transporting material include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Examples of the alkali metal complex, alkaline earth metal complex, or earth metal complex include lithium 8-hydroxyquinolinate (Liq), zinc bis(8-hydroxyquinolinate), and bis(8-hydroxyquinolinate). Copper, bis(8-hydroxyquinolinate) manganese, tris(8-hydroxyquinolinate) aluminum, tris(2-methyl-8-hydroxyquinolinate) aluminum, tris(8-hydroxyquinolinate) gallium, Bis(10-hydroxybenzo[h]quinolinate) beryllium, bis(10-hydroxybenzo[h]quinolinate) zinc, bis(2-methyl-8-quinolinate) chlorogallium, bis(2-methyl-8-quinolinate) ( Examples thereof include gallium (o-cresolate), aluminum bis(2-methyl-8-quinolinate)-1-naphtholate, and gallium bis(2-methyl-8-quinolinate)-2-naphtholate.
発光層と電子輸送層との間に、キャリアバランスを改善させる目的で、正孔阻止層を設けてもよい。正孔素子層として望ましい化合物は、ＢＣＰ（２，９－ジメチル－４，７－ジフェニル－１，１０－フェナントロリン）、Ｂｐｈｅｎ（４，７－ジフェニル－１，１０－フェナントロリン）、ＢＡｌｑ（ビス（２－メチル－８－キノリノラート）－４－（フェニルフェノラート）アルミニウム）、又はビス（１０－ヒドロキシベンゾ［ｈ］キノリナート）ベリリウム）等が挙げられる。 A hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance. Desirable compounds for the hole element layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), and BAlq (bis(2 -methyl-8-quinolinolate)-4-(phenylphenolate)aluminum), or bis(10-hydroxybenzo[h]quinolinate)beryllium).
本発明の有機ＥＬ素子においては、電子注入性を向上させ、素子特性（例えば、発光効率、定電圧駆動、又は高耐久性）を向上させる目的で、電子注入層を設けてもよい。 In the organic EL device of the present invention, an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, luminous efficiency, constant voltage drive, or high durability).
電子注入層として望ましい化合物としては、フルオレノン、アントラキノジメタン、ジフェノキノン、チオピランジオキシド、オキサゾール、オキサジアゾール、トリアゾール、イミダゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントラキノジメタン、アントロン等が挙げられる。また、上記に記した金属錯体やアルカリ金属酸化物、アルカリ土類酸化物、希土類酸化物、アルカリ金属ハロゲン化物、アルカリ土類ハロゲン化物、希土類ハロゲン化物、ＳｉＯ２、ＡｌＯ、ＳｉＮ、ＳｉＯＮ、ＡｌＯＮ、ＧｅＯ、ＬｉＯ、ＬｉＯＮ、ＴｉＯ、ＴｉＯＮ、ＴａＯ、ＴａＯＮ、ＴａＮ、Ｃなどの各種酸化物、窒化物、及び酸化窒化物のような無機化合物等も使用できる。 Desirable compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrane dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, etc. can be mentioned. In addition, the metal complexes described above, alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO 2 , AlO, SiN, SiON, AlON, Various oxides such as GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, and C, nitrides, and inorganic compounds such as oxynitrides can also be used.
発光が陽極を通してのみ確認される場合、本発明において使用される陰極は、任意の導電性材料から形成することができる。望ましい陰極材料としては、ナトリウム、ナトリウム－カリウム合金、マグネシウム、リチウム、マグネシウム／銅混合物、マグネシウム／銀混合物、マグネシウム／アルミニウム混合物、マグネシウム／インジウム混合物、アルミニウム／酸化アルミニウム（Ａｌ２Ｏ３）混合物、インジウム、リチウム／アルミニウム混合物、希土類金属等が挙げられる。 If light emission is only observed through the anode, the cathode used in the present invention can be formed from any electrically conductive material. Preferred cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium/copper mixture, magnesium/silver mixture, magnesium/aluminum mixture, magnesium/indium mixture, aluminum/aluminum oxide (Al 2 O 3 ) mixture, indium. , lithium/aluminum mixtures, rare earth metals, and the like.
以下、本発明を実施例に基づき、さらに詳細に説明するが、本発明はこれら実施例に何ら限定されて解釈されるものではない。 Hereinafter, the present invention will be explained in more detail based on Examples, but the present invention should not be construed as being limited to these Examples.
なお、本実施例で用いた分析機器及び測定方法を以下に列記する。 The analytical instruments and measurement methods used in this example are listed below.
［材料純度測定（ＨＰＬＣ分析）］
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）
[Material purity measurement (HPLC analysis)]
Measuring device: Tosoh Multi Station LC-8020
Measurement conditions: Column Inertsil ODS-3V (4.6mmΦ×250mm)
Detector UV detection (wavelength 254nm)
Eluent: methanol/tetrahydrofuran = 9/1 (v/v ratio)
[NMR measurement]
Measuring device: Varian Gemini300
[Mass spectrometry]
Mass spectrometer: Hitachi M-80B
Measurement method: FD-MS analysis [Redox stability evaluation]
Measuring device: HSV-110 manufactured by Hokuto Denko Co., Ltd.
[Light emission characteristics of organic EL element]
Measuring device: LUMINANCE METER (BM-9) manufactured by TOPCON
合成例１ 化合物（７）の合成
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％）。
Synthesis Example 1 Synthesis of Compound (7) Under a nitrogen stream, 74.1 g (264.4 mmol) of 2-iodobiphenyl, 50.0 g (261.8 mmol) of 2,6-dichlorobenzoic acid, and 90 g of potassium carbonate were placed in a 1000 mL three-necked flask. .5 g (654.5 mmol), tetrakis(triphenylphosphine)palladium 1.5 g (1.3 mmol), and dimethyl sulfoxide 300 mL were added, and the mixture was stirred at 140° C. for 18 hours. After cooling to room temperature, 300 mL of toluene and 300 mL of pure water were added, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1:1)), and the resulting residue was further concentrated under reduced pressure and recrystallized (toluene/2-propanol). 54.9 g (208.9 mmol) of a white solid of compound (7) was isolated (yield 80%).
化合物の同定は１Ｈ－ＮＭＲ測定により行った。 The compound was identified by 1 H-NMR measurement.
１Ｈ－ＮＭＲ（ＣＤＣｌ３）；９．５７（ｄ，１Ｈ），８．６４－８．５４（ｍ，４Ｈ），７．７３－７．６８（ｍ，１Ｈ），７．６６－７．５９（ｍ，４Ｈ），７．５２（ｔ，１Ｈ）
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％）。
1 H-NMR (CDCl 3 ); 9.57 (d, 1H), 8.64-8.54 (m, 4H), 7.73-7.68 (m, 1H), 7.66-7. 59 (m, 4H), 7.52 (t, 1H)
Synthesis Example 2 Synthesis of Compound (8) Under nitrogen flow, in a 500 mL three-necked flask, 24.4 g (92.8 mmol) of the compound (7) obtained in Synthesis Example 1, 33 g (130.0 mmol) of bis(pinacolato)diboron, Potassium acetate 27.4 (278.4 mmol), palladium acetate 104 mg (0.46 mmol), tricyclohexylphosphine 260 mg (0.93 mmol), and dimethyl sulfoxide 200 mL were added, and the mixture was stirred at 120° C. for 3 hours. After cooling to room temperature, 200 mL of toluene and 200 mL of pure water were added, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. Next, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to isolate 31.2 g (88.2 mmol) of a pale yellow viscous liquid of compound (8) (yield 95%).
化合物の同定はＦＤＭＳにより行った。 Compound identification was performed by FDMS.
ＦＤＭＳ（ｍ／ｚ）； ３５４（Ｍ＋）
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％）。
FDMS (m/z); 354 (M+)
Synthesis Example 3 Synthesis of Compound (9) Under a nitrogen stream, 11.0 g (31.0 mmol) of the compound (8) obtained in Synthesis Example 2 and 8.9 g ( 37.2 mmol), potassium carbonate 12.8 (93.0 mmol), tetrakis(triphenylphosphine)palladium 1.1 g (0.93 mmol), and dimethyl sulfoxide 100 mL, and the mixture was stirred at 120° C. for 18 hours. After cooling to room temperature, 100 mL of toluene and 100 mL of pure water were added, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. By purifying the residue with silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1:4)), 5.4 g (15.9 mmol) of a white solid of compound (9) was isolated (yield: 51%).
化合物の同定は１Ｈ－ＮＭＲ測定により行った。 The compound was identified by 1 H-NMR measurement.
１Ｈ－ＮＭＲ（ＣＤＣｌ３）；８．６６－８．５８（ｍ，３Ｈ），８．５５（ｄ，１Ｈ），７．７１（ｄ，１Ｈ），７．６９－７．６２（ｍ，３Ｈ），７．４８（ｔ，２Ｈ），７．４２－７．３４（ｍ，４Ｈ），７．１０（ｔ，１Ｈ）
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％）。
1 H-NMR (CDCl 3 ); 8.66-8.58 (m, 3H), 8.55 (d, 1H), 7.71 (d, 1H), 7.69-7.62 (m, 3H), 7.48 (t, 2H), 7.42-7.34 (m, 4H), 7.10 (t, 1H)
Synthesis Example 4 Synthesis of Compound (10) Under a nitrogen stream, 10.0 g (38.1 mmol) of 1-chlorotriphenylene (compound (7)) obtained in Synthesis Example 1 and 10.6 g (114 mmol) of aniline were placed in a 50 mL three-necked flask. .3 mmol), sodium-tert-butoxide 4.8 g (49.5 mmol), and o-xylene 100 mL were added, and to the resulting slurry-like reaction solution, palladium acetate 171.1 mg (0.76 mmol) and tri-tert-butoxide were added. -Butylphosphine 462.5 mg (2.3 mmol) was added and stirred at 140°C for 24 hours. After cooling to room temperature, 100 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1:1)), and the resulting residue was further concentrated under reduced pressure and recrystallized (toluene/butanol) to obtain the compound ( 6.0 g (18.8 mmol) of white powder of 10) was isolated (yield 49%).
化合物の同定はＦＤＭＳにより行った。 Compound identification was performed by FDMS.
ＦＤＭＳ（ｍ／ｚ）； ３１９（Ｍ＋）
実施例１ （化合物（Ａ７）の合成）
FDMS (m/z); 319 (M+)
Example 1 (Synthesis of compound (A7))
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）） １．０ｇ（３．８ｍｍｏｌ）、Ｎ－｛３－［ビス（４－ビフェニリル）アミノ］フェニル｝フェニルアミン １．９ｇ（３．９ｍｍｏｌ）、ナトリウム－ｔｅｒｔ－ブトキシド ０．４８ｇ（５．０ｍｍｏｌ）、及びｏ－キシレン １０ｍＬを加え、得られたスラリー状の反応液に酢酸パラジウム ４２．８ｍｇ（０．１９ｍｍｏｌ）、及びトリ－ｔｅｒｔ－ブチルホスフィン １１５．６ｍｇ（０．５７ｍｍｏｌ）を添加して１４０℃で２４時間攪拌した。室温まで冷却後、純水を１０ｍＬ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））で精製することにより、化合物（Ａ７）の白色粉末を１．４ｇ（２．０ｍｍｏｌ）単離した（収率５１％）。 Under a nitrogen stream, 1.0 g (3.8 mmol) of 1-chlorotriphenylene (compound (7)) obtained in Synthesis Example 1 and N-{3-[bis(4-biphenylyl)amino]phenyl were placed in a 50 mL three-necked flask. }Phenylamine 1.9 g (3.9 mmol), sodium-tert-butoxide 0.48 g (5.0 mmol), and o-xylene 10 mL were added, and palladium acetate 42.8 mg (0 .19 mmol) and 115.6 mg (0.57 mmol) of tri-tert-butylphosphine were added and stirred at 140° C. for 24 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. By purifying the residue with silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1:1)), 1.4 g (2.0 mmol) of white powder of compound (A7) was isolated (yield 51%).
化合物の同定はＦＤＭＳにより行った。 Compound identification was performed by FDMS.
ＦＤＭＳ（ｍ／ｚ）； ７１４（Ｍ＋）
実施例２ （化合物（Ａ８９）の合成）
FDMS (m/z); 714 (M+)
Example 2 (Synthesis of compound (A89))
Ｎ－｛３－［ビス（４－ビフェニリル）アミノ］フェニル｝フェニルアミン １．９ｇ（３．９ｍｍｏｌ）の代わりに、Ｎ－［３－（ジフェニルアミノ）フェニル］－４－ビフェニルアミン １．６ｇ（３．９ｍｍｏｌ）を用いた以外は実施例１と同様の操作を行って、化合物（Ａ８９）の白色粉末を１．２ｇ（１．９ｍｍｏｌ）単離した（収率４９％）。 Instead of 1.9 g (3.9 mmol) of N-{3-[bis(4-biphenylyl)amino]phenyl}phenylamine, 1.6 g ( The same operation as in Example 1 was performed except that 3.9 mmol) was used, and 1.2 g (1.9 mmol) of white powder of compound (A89) was isolated (yield: 49%).
化合物の同定はＦＤＭＳにより行った。 Compound identification was performed by FDMS.
ＦＤＭＳ（ｍ／ｚ）； ６３８（Ｍ＋）
実施例３ （化合物（Ａ１８２）の合成）
FDMS (m/z); 638 (M+)
Example 3 (Synthesis of compound (A182))
窒素気流下、５０ｍＬの三口フラスコに、合成例４で得たＮ－フェニル－１－トリフェニレニルアミン（化合物（１０）） １．４ｇ（４．５ｍｍｏｌ）、４’－ブロモトリ（４－ビフェニリル）アミン ２．４ｇ（４．３ｍｍｏｌ）、ナトリウム－ｔｅｒｔ－ブトキシド ０．５４ｇ（５．６ｍｍｏｌ）、及びｏ－キシレン ２０ｍＬを加え、得られたスラリー状の反応液に酢酸パラジウム ９．６ｍｇ（０．０４３ｍｍｏｌ）、及びトリ－ｔｅｒｔ－ブチルホスフィン ２６．１ｍｇ（０．１２９ｍｍｏｌ）を添加して１４０℃で２時間攪拌した。室温まで冷却後、純水を２０ｍＬ添加し攪拌した。析出した固体をろ過し、メタノールで洗浄後、残渣を再結晶（トルエン）することにより、化合物（Ａ１８２）の淡黄色粉末を３．１ｇ（３．９ｍｍｏｌ）単離した（収率９０％）
化合物の同定はＦＤＭＳにより行った。
Under a nitrogen stream, 1.4 g (4.5 mmol) of N-phenyl-1-triphenylenylamine (compound (10)) obtained in Synthesis Example 4 and 4'-bromotri(4-biphenylyl)amine were placed in a 50 mL three-necked flask. 2.4 g (4.3 mmol), sodium-tert-butoxide 0.54 g (5.6 mmol), and o-xylene 20 mL were added, and palladium acetate 9.6 mg (0.043 mmol) was added to the resulting slurry reaction liquid. , and 26.1 mg (0.129 mmol) of tri-tert-butylphosphine were added and stirred at 140° C. for 2 hours. After cooling to room temperature, 20 mL of pure water was added and stirred. The precipitated solid was filtered, washed with methanol, and the residue was recrystallized (toluene) to isolate 3.1 g (3.9 mmol) of pale yellow powder of compound (A182) (yield 90%).
Compound identification was performed by FDMS.
ＦＤＭＳ（ｍ／ｚ）； ７９０（Ｍ＋）
実施例４ （化合物（Ｂ４５）の合成）
FDMS (m/z); 790 (M+)
Example 4 (Synthesis of compound (B45))
窒素気流下、５０ｍＬの三口フラスコに、合成例３で得た１－（４－クロロフェニル）トリフェニレン（化合物（９）） ０．８０ｇ（２．４ｍｍｏｌ）、Ｎ－｛３－［ビス（４－ビフェニリル）アミノ］フェニル｝フェニルアミン １．２ｇ（２．４ｍｍｏｌ）、ナトリウム－ｔｅｒｔ－ブトキシド ０．２９ｇ（３．１ｍｍｏｌ）、及びｏ－キシレン １０ｍＬを加え、得られたスラリー状の反応液に酢酸パラジウム ５．３ｍｇ（０．０２４ｍｍｏｌ）、及びトリ－ｔｅｒｔ－ブチルホスフィン １４．３ｍｇ（０．０７１ｍｍｏｌ）を添加して１４０℃で３時間攪拌した。室温まで冷却後、純水を１０ｍＬ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））で精製することにより、化合物（Ｂ４５）の白色粉末を１．７ｇ（２．１ｍｍｏｌ）単離した（収率９１％）。 Under a nitrogen stream, 0.80 g (2.4 mmol) of 1-(4-chlorophenyl)triphenylene (compound (9)) obtained in Synthesis Example 3, N-{3-[bis(4-biphenylyl) )Amino]phenyl}phenylamine 1.2g (2.4mmol), sodium-tert-butoxide 0.29g (3.1mmol), and o-xylene 10mL were added, and palladium acetate 5% was added to the resulting slurry reaction liquid. .3 mg (0.024 mmol) and tri-tert-butylphosphine 14.3 mg (0.071 mmol) were added and stirred at 140° C. for 3 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. By purifying the residue with silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1:1)), 1.7 g (2.1 mmol) of white powder of compound (B45) was isolated (yield 91%).
化合物の同定はＦＤＭＳにより行った。 Compound identification was performed by FDMS.
ＦＤＭＳ（ｍ／ｚ）； ７９０（Ｍ＋）
実施例５ （化合物（Ｂ４９）の合成）
FDMS (m/z); 790 (M+)
Example 5 (Synthesis of compound (B49))
Ｎ－｛３－［ビス（４－ビフェニリル）アミノ］フェニル｝フェニルアミン ０．８０ｇ（２．４ｍｍｏｌ）の代わりに、Ｎ－［３－（ジフェニルアミノ）フェニル］－４－ビフェニルアミン ０．９９ｇ（２．４ｍｍｏｌ）を用いた以外は実施例４と同様の操作を行って、化合物（Ｂ４９）の白色粉末を１．５ｇ（２．０ｍｍｏｌ）単離した（収率８５％）。 Instead of 0.80 g (2.4 mmol) of N-{3-[bis(4-biphenylyl)amino]phenyl}phenylamine, 0.99 g ( The same operation as in Example 4 was performed except that 2.4 mmol) was used, and 1.5 g (2.0 mmol) of white powder of compound (B49) was isolated (yield: 85%).
化合物の同定はＦＤＭＳにより行った。 Compound identification was performed by FDMS.
ＦＤＭＳ（ｍ／ｚ）； ７１４（Ｍ＋）
実施例６ （化合物（Ａ１５９）の合成）
FDMS (m/z); 714 (M+)
Example 6 (Synthesis of compound (A159))
窒素気流下、５０ｍＬの三口フラスコに、合成例４で得たＮ－フェニル－１－トリフェニレニルアミン（化合物（１０）） １．６ｇ（５．２ｍｍｏｌ）、３’－クロロトリ（４－ビフェニリル）アミン ２．５ｇ（５．０ｍｍｏｌ）、ナトリウム－ｔｅｒｔ－ブトキシド ０．６２ｇ（６．５ｍｍｏｌ）、及びｏ－キシレン ２０ｍＬを加え、得られたスラリー状の反応液に酢酸パラジウム １１．２ｍｇ（０．０５ｍｍｏｌ）、及びトリ－ｔｅｒｔ－ブチルホスフィン ３０．３ｍｇ（０．１５ｍｍｏｌ）を添加して１４０℃で２時間攪拌した。室温まで冷却後、純水を２０ｍＬ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＝２：１））で精製することにより、化合物（Ａ１５９）の白色粉末を２．４ｇ（３．０ｍｍｏｌ）単離した（収率６１％）。 Under a nitrogen stream, 1.6 g (5.2 mmol) of N-phenyl-1-triphenylenylamine (compound (10)) obtained in Synthesis Example 4 and 3'-chlorotri(4-biphenylyl)amine were placed in a 50 mL three-necked flask. 2.5 g (5.0 mmol), sodium-tert-butoxide 0.62 g (6.5 mmol), and o-xylene 20 mL were added, and palladium acetate 11.2 mg (0.05 mmol) was added to the resulting slurry reaction liquid. , and 30.3 mg (0.15 mmol) of tri-tert-butylphosphine were added and stirred at 140° C. for 2 hours. After cooling to room temperature, 20 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. By purifying the residue with silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 2:1)), 2.4 g (3.0 mmol) of white powder of compound (A159) was isolated (yield 61%).
化合物の同定はＦＤＭＳにより行った。 Compound identification was performed by FDMS.
ＦＤＭＳ（ｍ／ｚ）； ７９０（Ｍ＋）
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。
FDMS (m/z); 790 (M+)
Example 7 (Redox stability evaluation of compound (A182))
The redox stability of compound (A182) was evaluated by cyclic voltammetry. Compound (A182) was dissolved at a concentration of 0.001 mol/L in an anhydrous dichloromethane solution containing tetrabutylammonium perchlorate at a concentration of 0.1 mol/L, and glassy carbon was used as the working electrode, a platinum wire was used as the counter electrode, and a platinum wire was used as the reference electrode. A cyclic voltammogram of compound (A182) was obtained using a silver wire immersed in an acetonitrile solution of AgNO3 (Figure 1). Compound (A182) exhibited reversible redox waves and was stable against two-electron oxidation.
比較例１ （化合物（ａ）の酸化還元安定性評価）
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。
Comparative Example 1 (Redox stability evaluation of compound (a))
In the same manner as in Example 7, the redox stability of the compound described on page 27 of Korean Patent Application Publication No. 10-2017-0136915 (corresponding to compound (a) described in the latter part) was determined. evaluated. Compound (a) had irreversible secondary oxidation (FIG. 2) and was unstable to two-electron oxidation.
実施例８ （化合物（Ａ７）の素子評価）
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。
Example 8 (Device evaluation of compound (A7))
The structural formulas and abbreviations of the compounds used for device evaluation are shown below.
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／オゾン洗浄を行い、真空蒸着装置へ設置後、１×１０－４Ｐａになるまで真空ポンプで排気した。まず、ＩＴＯ透明電極上にＨＩＬを０．１５ｎｍ／秒の速度で５５ｎｍ成膜し、正孔注入層を作製し、引続き、ＨＡＴを０．０５ｎｍ／秒の速度で５ｎｍ成膜し、電荷発生層を作製した。次に、ＨＴＬ－１を０．１５ｎｍ／秒の速度で１５ｎｍ成膜し、第一正孔輸送層を作製し、続いて、化合物（Ａ７）を０．１５ｎｍ／秒の速度で５０ｎｍ成膜し、第二正孔輸送層を作製した。次に、ＥＭＬ－１およびＥＭＬ－２を９７：３（質量比）になるように蒸着速度０．１５ｎｍ／秒で共蒸着し、３０ｎｍの発光層とした。続いて、ＥＴＬおよびＬｉｑを５０：５０（質量比）になるように蒸着速度０．１５ｎｍ／秒で共蒸着し、３０ｎｍの電子輸送層とした。最後に、基板上のＩＴＯストライプと直交するようにメタルマスクを配し、陰極を成膜した。陰極は、銀／マグネシウム（質量比１／１０）と銀とを、この順番で、それぞれ８０ｎｍと２０ｎｍとで成膜し、２層構造とした。銀／マグネシウムの成膜速度は０．５ｎｍ／秒、銀の成膜速度は成膜速度０．２ｎｍ／秒であった。以上により、発光面積４ｍｍ２有機電界発光素子を作製し、それぞれの膜厚は触針式膜厚測定計（ＤＥＫＴＡＫ、Ｂｒｕｋｅｒ社製）で測定した。さらに、この素子を酸素および水分濃度１ｐｐｍ以下の窒素雰囲気グローブボックス内で封止した。封止は、ガラス製の封止キャップと成膜基板（素子）とを、ビスフェノールＦ型エポキシ樹脂（ナガセケムテックス社製）を用いて行った。上記のようにして作製した有機電界発光素子に直流電流を印加し、輝度計を用いて発光特性を評価した。発光特性として、電流密度１０ｍＡ／ｃｍ２を流した時の駆動電圧（Ｖ）、電流効率（ｃｄ／Ａ）を測定した。また、素子寿命（ｈｒ）は、作製した素子を初期輝度４０００ｃｄ／ｍ２で駆動したときの連続点灯時の輝度減衰時間を測定し、輝度（ｃｄ／ｍ２）が２０％減じるまでに要した時間を測定した。得られた測定結果を表１に示す。なお、駆動電圧、電流効率及び素子寿命については、後述する比較例２における結果を基準値（１００）とした相対値で表した。なお、駆動電圧の相対値は、小さいほど駆動電圧が低く、好ましい。電流効率の相対値は、大きいほど電流効率が高く、好ましい。素子寿命の相対値は、大きいほど寿命が長く、好ましい。 A glass substrate on which a 200 nm thick ITO transparent electrode (anode) was laminated was subjected to ultrasonic cleaning with acetone and pure water and boiling cleaning with isopropyl alcohol. Furthermore, ultraviolet ray/ozone cleaning was performed, and after installation in a vacuum evaporation apparatus, it was evacuated with a vacuum pump until the pressure reached 1×10 −4 Pa. First, HIL was deposited to a thickness of 55 nm on the ITO transparent electrode at a rate of 0.15 nm/sec to form a hole injection layer, and then HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm/sec to form a charge generation layer. was created. Next, HTL-1 was deposited to a thickness of 15 nm at a rate of 0.15 nm/sec to form a first hole transport layer, and then compound (A7) was deposited to a thickness of 50 nm at a rate of 0.15 nm/sec. , a second hole transport layer was prepared. Next, EML-1 and EML-2 were co-evaporated at a deposition rate of 0.15 nm/sec at a ratio of 97:3 (mass ratio) to form a 30 nm light emitting layer. Subsequently, ETL and Liq were co-evaporated at a deposition rate of 0.15 nm/sec at a ratio of 50:50 (mass ratio) to form an electron transport layer of 30 nm. Finally, a metal mask was placed so as to be perpendicular to the ITO stripes on the substrate, and a cathode was formed. The cathode had a two-layer structure by forming films of silver/magnesium (mass ratio 1/10) and silver to have a thickness of 80 nm and 20 nm, respectively, in this order. The deposition rate of silver/magnesium was 0.5 nm/sec, and the deposition rate of silver was 0.2 nm/sec. As described above, 2 organic electroluminescent devices with a light emitting area of 4 mm were produced, and the film thickness of each was measured using a stylus film thickness meter (DEKTAK, manufactured by Bruker). Furthermore, this device was sealed in a nitrogen atmosphere glove box with an oxygen and moisture concentration of 1 ppm or less. Sealing was performed using a glass sealing cap and a film-forming substrate (element) using bisphenol F type epoxy resin (manufactured by Nagase ChemteX). A direct current was applied to the organic electroluminescent device produced as described above, and its luminescence characteristics were evaluated using a luminance meter. As luminescent characteristics, the driving voltage (V) and current efficiency (cd/A) when a current density of 10 mA/cm 2 was applied were measured. In addition, the element life (hr) was determined by measuring the brightness decay time during continuous lighting when the fabricated element was driven at an initial brightness of 4000 cd/ m2 , and was calculated as the time required for the brightness (cd/ m2 ) to decrease by 20%. The time was measured. The measurement results obtained are shown in Table 1. Note that the drive voltage, current efficiency, and element life are expressed as relative values, with the results in Comparative Example 2 described later being taken as a reference value (100). Note that the smaller the relative value of the drive voltage is, the lower the drive voltage is, which is preferable. The larger the relative value of current efficiency, the higher the current efficiency, which is preferable. The larger the relative value of the element life, the longer the life, which is preferable.
実施例９ （化合物（Ａ８９）の素子評価）
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。
Example 9 (Device evaluation of compound (A89))
An organic EL device was produced in the same manner as in Example 8 except that compound (A89) was used instead of compound (A7). Regarding the organic EL element, the driving voltage, current efficiency, and element life measured in the same manner as in Example 8 are shown in Table 1.
実施例１０ （化合物（Ａ１８２）の素子評価）
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。
Example 10 (Device evaluation of compound (A182))
An organic EL device was produced in the same manner as in Example 8 except that compound (A182) was used instead of compound (A7). Regarding the organic EL element, the driving voltage, current efficiency, and element life measured in the same manner as in Example 8 are shown in Table 1.
実施例１１ （化合物（Ｂ４５）の素子評価）
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。
Example 11 (Device evaluation of compound (B45))
An organic EL device was produced in the same manner as in Example 8 except that compound (B45) was used instead of compound (A7). Regarding the organic EL element, the driving voltage, current efficiency, and element life measured in the same manner as in Example 8 are shown in Table 1.
実施例１２ （化合物（Ｂ４９）の素子評価）
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。
Example 12 (Device evaluation of compound (B49))
An organic EL device was produced in the same manner as in Example 8 except that compound (B49) was used instead of compound (A7). Regarding the organic EL element, the driving voltage, current efficiency, and element life measured in the same manner as in Example 8 are shown in Table 1.
実施例１３ （化合物（Ａ１５９）の素子評価）
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。
Example 13 (Device evaluation of compound (A159))
An organic EL device was produced in the same manner as in Example 8 except that compound (A159) was used instead of compound (A7). Regarding the organic EL element, the driving voltage, current efficiency, and element life measured in the same manner as in Example 8 are shown in Table 1.
比較例２ （化合物（ａ）の素子評価）
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。
Comparative example 2 (device evaluation of compound (a))
An organic EL device was produced in the same manner as in Example 8 except that the following compound (a) was used instead of compound (A7). Regarding the organic EL element, the driving voltage, current efficiency, and element life measured in the same manner as in Example 8 are shown in Table 1.
比較例３ （化合物（ｂ）の素子評価）
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。
Comparative example 3 (device evaluation of compound (b))
Same method as Example 8 except that compound A-1 (corresponding to compound (b) below) described on page 21 of International Publication No. 2010/002850 pamphlet was used instead of compound (A7). An organic EL device was manufactured using the following steps. Regarding the organic EL element, the driving voltage, current efficiency, and element life measured in the same manner as in Example 8 are shown in Table 1.
本発明のトリフェニレン化合物は、有機ＥＬ素子用材料として、例えば、正孔注入材料、正孔輸送材料又は発光層のホスト材料として利用可能であり、従来公知材料を用いた有機ＥＬ素子と比較して、駆動電圧、素子効率及び寿命に優れる。さらには、有機ＥＬ素子又は電子写真感光体の正孔注入材料、正孔輸送材料又は発光材料としてのみでなく、光電変換素子、太陽電池、又はイメージセンサー等の有機光導電材料への分野にも応用可能である。 The triphenylene compound of the present invention can be used as a material for organic EL devices, for example, as a hole-injecting material, a hole-transporting material, or a host material for a light-emitting layer, and compared to organic EL devices using conventionally known materials. , excellent drive voltage, element efficiency and lifespan. Furthermore, it can be used not only as a hole injection material, hole transport material, or luminescent material for organic EL elements or electrophotographic photoreceptors, but also for organic photoconductive materials such as photoelectric conversion elements, solar cells, and image sensors. It is applicable.
Claims (6)
Ｌ１は、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。Ｌ2は、１，３－フェニレン基、又は１，４－フェニレン基を表す。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、ｍ、及びｐは、０を表す。） A triphenylene compound represented by general formula (1).
L 1 is a single bond, or a monocyclic, connected ring, or fused ring divalent aromatic hydrocarbon group having 6 to 20 carbon atoms [each of these groups independently represents a methyl group, an ethyl group, a carbon number Straight chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group, ethoxy group, straight chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms, halogenated alkyl group having 1 to 3 carbon atoms, carbon A halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, connected ring, or fused ring aryl group having 6 to 20 carbon atoms, a monocyclic, connected ring, or fused ring aryloxy group having 6 to 18 carbon atoms, carbon Monocyclic, connected ring, or fused ring heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, triarylsilyl group having 18 to 40 carbon atoms, cyano group, halogen atom, and deuterium It may have one or more substituents selected from the group consisting of atoms. ] represents. L 2 represents a 1,3 -phenylene group or a 1,4-phenylene group. R 1 to R 3 each independently represent a methyl group, a methoxy group, or a cyano group, and n, m, and p represent 0. )
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