WO2024166615A1 - Compound and organic electroluminescent element using same - Google Patents
Compound and organic electroluminescent element using same Download PDFInfo
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- WO2024166615A1 WO2024166615A1 PCT/JP2024/000823 JP2024000823W WO2024166615A1 WO 2024166615 A1 WO2024166615 A1 WO 2024166615A1 JP 2024000823 W JP2024000823 W JP 2024000823W WO 2024166615 A1 WO2024166615 A1 WO 2024166615A1
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- substituted
- unsubstituted
- carbon atoms
- ring
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 241
- 125000004432 carbon atom Chemical group C* 0.000 claims description 407
- -1 biphenyldiyl group Chemical group 0.000 claims description 240
- 125000000623 heterocyclic group Chemical group 0.000 claims description 197
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 190
- 125000003118 aryl group Chemical group 0.000 claims description 145
- 125000000217 alkyl group Chemical group 0.000 claims description 129
- 125000006413 ring segment Chemical group 0.000 claims description 114
- 125000001424 substituent group Chemical group 0.000 claims description 112
- 239000000463 material Substances 0.000 claims description 66
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 125000003342 alkenyl group Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- 125000001624 naphthyl group Chemical group 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 125000000732 arylene group Chemical group 0.000 claims description 23
- 238000005401 electroluminescence Methods 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- MNXYJVWXMUBENA-UHFFFAOYSA-N dinaphthofuran Chemical group C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)O3)C3=CC=C21 MNXYJVWXMUBENA-UHFFFAOYSA-N 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 16
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001725 pyrenyl group Chemical group 0.000 claims description 14
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004957 naphthylene group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 191
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- 125000004429 atom Chemical group 0.000 description 35
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- 239000007924 injection Substances 0.000 description 23
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- 239000007787 solid Substances 0.000 description 14
- 150000001721 carbon Chemical group 0.000 description 13
- 229910052805 deuterium Inorganic materials 0.000 description 13
- 238000004949 mass spectrometry Methods 0.000 description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- 125000000547 substituted alkyl group Chemical group 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 239000013076 target substance Substances 0.000 description 13
- 150000001975 deuterium Chemical group 0.000 description 12
- 125000004431 deuterium atom Chemical group 0.000 description 12
- 125000005017 substituted alkenyl group Chemical group 0.000 description 12
- 125000003107 substituted aryl group Chemical group 0.000 description 12
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- 125000004434 sulfur atom Chemical group 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 125000005577 anthracene group Chemical group 0.000 description 6
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000001296 phosphorescence spectrum Methods 0.000 description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 239000002184 metal Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 150000001846 chrysenes Chemical class 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920000642 polymer Chemical class 0.000 description 4
- 150000003220 pyrenes Chemical class 0.000 description 4
- 230000000630 rising effect Effects 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 3
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 229910052790 beryllium Inorganic materials 0.000 description 3
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
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- 125000005647 linker group Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
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- 125000004426 substituted alkynyl group Chemical group 0.000 description 3
- OVTCUIZCVUGJHS-VQHVLOKHSA-N trans-dipyrrin Chemical compound C=1C=CNC=1/C=C1\C=CC=N1 OVTCUIZCVUGJHS-VQHVLOKHSA-N 0.000 description 3
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- 229910052725 zinc Inorganic materials 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 101100016516 Caenorhabditis elegans hbl-1 gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 102220475437 Vacuolar protein sorting-associated protein 33A_D33A_mutation Human genes 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 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
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
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- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
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- 230000007423 decrease Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical class [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
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- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
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- 150000002987 phenanthrenes Chemical class 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
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- WTGQALLALWYDJH-WYHSTMEOSA-N scopolamine hydrobromide Chemical compound Br.C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 WTGQALLALWYDJH-WYHSTMEOSA-N 0.000 description 2
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
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- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
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- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910017073 AlLi Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 150000000918 Europium Chemical class 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- 150000001217 Terbium Chemical class 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical class O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical class O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ILYGRCGTUMHLGR-UHFFFAOYSA-N acenaphtho[1,2-j]fluoranthene Chemical class C1=CC2=CC=CC(C=3C4=C5C=6C=CC=C7C=CC=C(C=67)C5=CC=3)=C2C4=C1 ILYGRCGTUMHLGR-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 125000005390 cinnolyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical class [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- WIAWDMBHXUZQGV-UHFFFAOYSA-N heptacyclo[13.10.1.12,6.011,26.017,25.018,23.010,27]heptacosa-1(25),2,4,6(27),7,9,11,13,15(26),17,19,21,23-tridecaene Chemical class C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=C1C=C3C=CC=CC3=C1C2 WIAWDMBHXUZQGV-UHFFFAOYSA-N 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- FQHFBFXXYOQXMN-UHFFFAOYSA-M lithium;quinolin-8-olate Chemical compound [Li+].C1=CN=C2C([O-])=CC=CC2=C1 FQHFBFXXYOQXMN-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical class [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 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
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical class O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 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
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- RAPRNSRXWWPZEV-UHFFFAOYSA-N spiro[fluorene-9,9'-thioxanthene] Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 RAPRNSRXWWPZEV-UHFFFAOYSA-N 0.000 description 1
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
- H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
Definitions
- the present invention relates to a novel compound and an organic electroluminescence device using the compound.
- an organic electroluminescence element hereinafter also referred to as an organic EL element
- holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer.
- the injected holes and electrons recombine to form excitons.
- the object of the present invention is to provide a high-performance organic EL element and a compound capable of realizing such an organic EL element.
- a compound represented by the following formula (1) [In formula (1), One of R 101 to R 105 is a single bond bonded to a group represented by the following formula (A1).
- L A1 is, Single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, a substituted or unsubstituted terphenyldiyl group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthryldiyl group, a substituted or unsubstituted benzophenanthryldiyl group, a substituted or unsubstituted benzanthracenediyl group, a substituted or unsubstituted pyrenediyl group, a substituted or unsubstituted chrysenediyl
- Ar A1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted fluorenyl group, a substitute
- nA1 is an integer of 0 to 3. When nA1 is 0, (L A1 ) nA1 is a single bond. When nA1 is 2 or 3, multiple L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the most distant from the dinaphthofuran skeleton. Multiple L A1 may be the same or different.
- One or more pairs of adjacent two or more of R 106 to R 112 and R 101 to R 105 that are not a single bond bonded to the group represented by formula (A1) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
- R 106 to R 112 which are not bonded to each other, and R 101 to R 105 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A1) each independently represent: It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A1).
- R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms. When two or more of R 41 to R 45 and R 49 to R 51 are present, the two or more of R 41 to R 45 and R 49 to R 51 may be the same or different.] 2.
- L A2 is, Single bond, It is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
- Ar A2 is It is a substituted or unsubstituted aryl group consisting of 5 or less rings and having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
- nA2 is an integer from 0 to 3. When nA2 is 0, (L A2 ) nA2 is a single bond.
- nA2 is 2 or 3
- multiple L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the most distant from the dinaphthofuran skeleton.
- Multiple L A2 may be the same or different.
- R 206 to R 212 and R 201 to R 205 that are not single bonds bonded to the group represented by formula (A2)
- one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
- R 206 to R 212 which are not bonded to each other, and R 201 to R 205 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A2) each independently represent: It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A2).
- R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
- R 41 to R 45 and R 49 to R 51 may be the same or different.
- the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms which are composed of 5 or less rings in Ar A2 are each a group which satisfies the following formula (T1). T 1 >1.81eV...(T1) (In formula (T1), T1 is the triplet energy of the group.) 3.
- L A3 is, Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
- Ar A3 is It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.
- nA3 is an integer from 0 to 3. When nA3 is 0, (L A3 ) nA3 is a single bond.
- nA3 is 2 or 3
- multiple L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the most distant from the dinaphthofuran skeleton.
- Multiple L A3 may be the same or different.
- R 306 to R 312 and R 301 to R 305 which are not single bonds bonded to the group represented by formula (A3), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
- R 306 to R 312 which are not bonded to each other, and R 301 to R 305 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A3) each independently represent: a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that is not the same as the group represented by formula (A3).
- the present invention provides a high-performance organic EL element and a compound capable of realizing the organic EL element.
- FIG. 1 is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention.
- hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.
- any possible bonding position that is not explicitly indicated with a symbol such as "R" or "D” representing a deuterium atom is assumed to have a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, bonded to it.
- the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound).
- a compound having a structure in which atoms are bonded in a ring for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound.
- the carbon contained in the substituent is not included in the number of ring carbon atoms.
- the "number of ring carbon atoms" described below is the same unless otherwise specified.
- a benzene ring has 6 ring carbon atoms
- a naphthalene ring has 10 ring carbon atoms
- a pyridine ring has 5 ring carbon atoms
- a furan ring has 4 ring carbon atoms.
- a 9,9-diphenylfluorenyl group has 13 ring carbon atoms
- a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.
- the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring.
- the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6.
- the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
- the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) with a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly).
- the number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent.
- the "number of ring atoms" described below is the same unless otherwise specified.
- the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5.
- the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6.
- the number of ring atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
- the "carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having carbon numbers XX to YY” refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted.
- "YY" is larger than “XX”
- "XX” means an integer of 1 or more
- "YY” means an integer of 2 or more.
- the "atomic number XX to YY” in the expression “substituted or unsubstituted ZZ group having atomic number XX to YY” refers to the atomic number when the ZZ group is unsubstituted, and does not include the atomic number of the substituent when the ZZ group is substituted.
- "YY" is larger than “XX”
- "XX” means an integer of 1 or more
- "YY” means an integer of 2 or more.
- unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group” is an "unsubstituted ZZ group”
- substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group” is a "substituted ZZ group”.
- unsubstituted in the case of "a substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
- the hydrogen atom in the "unsubstituted ZZ group” is a protium atom, a deuterium atom, or a tritium atom.
- substitution in the case of "a substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
- substitution in the case of "a BB group substituted with an AA group” means that one or more hydrogen atoms in the BB group are replaced with an AA group.
- the "unsubstituted aryl group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
- the "unsubstituted heterocyclic group” described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
- the "unsubstituted alkyl group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
- the number of carbon atoms in the "unsubstituted alkenyl group” described in this specification is, unless otherwise specified in this specification, 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
- the number of carbon atoms in the "unsubstituted alkynyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
- the "unsubstituted cycloalkyl group” described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification.
- the "unsubstituted arylene group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
- the number of ring atoms in the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
- the "unsubstituted alkylene group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
- Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B).
- unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is an "unsubstituted aryl group"
- substituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is a "substituted aryl group”.
- aryl group simply refers to both an "unsubstituted aryl group” and a "substituted aryl group”.
- substituted aryl group refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group” are replaced with a substituent.
- substituted aryl group include the "unsubstituted aryl group” in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below.
- the examples of the "unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are merely examples, and the "substituted aryl group” described in this specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group” in the specific example group G1B below is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group” in the specific example group G1B below is further replaced with a substituent.
- Unsubstituted aryl groups (specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, Benzanthryl group, A phenanthryl group, Benzophenanthryl group, A phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group,
- Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, A meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, triphenyls
- heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom.
- the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
- the “heterocyclic groups” described herein are either monocyclic or fused ring groups.
- the “heterocyclic group” described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group.
- Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B).
- the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group"
- the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group”.
- substituted heterocyclic group refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
- Specific examples of the "substituted heterocyclic group” include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified.
- the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are merely examples, and the “substituted heterocyclic group” described in this specification also includes the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.
- Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
- Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
- Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, A pyrimidinyl group, Pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, A quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl
- Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
- Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): A thienyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, Benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanap
- X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2 , provided that at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
- the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from the NH or CH2 .
- Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): A (9-phenyl)carbazolyl group, A (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, A phenylcarbazol-9-yl group, methylbenzimidazolyl group, Ethyl benzimidazolyl group, phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
- Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, The t-butyldibenzofuranyl group, and the monovalent radical of spiro[9H-xanthene-9,9'-[9H]fluorene].
- Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, The t-butyldibenzothiophenyl group, and the monovalent radical of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
- one or more hydrogen atoms of a monovalent heterocyclic group means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH2 .
- Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B).
- the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group"
- the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group” is a "substituted alkyl group”.
- substituted alkyl group refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group” are replaced with a substituent.
- specific examples of the "substituted alkyl group” include the following "unsubstituted alkyl group” (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B).
- the alkyl group in the "unsubstituted alkyl group” refers to a chain-like alkyl group.
- the "unsubstituted alkyl group” includes a straight-chain “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
- the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the "substituted alkyl group” described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent.
- Unsubstituted alkyl groups (specific example group G3A): Methyl group, Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-Butyl group, and t-butyl group.
- Substituted alkyl groups (specific example group G3B): Heptafluoropropyl group (including isomers), pentafluoroethyl group, A 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
- Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B).
- the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group” is an "unsubstituted alkenyl group", and the "substituted alkenyl group” refers to the case where the "substituted or unsubstituted alkenyl group” is a "substituted alkenyl group”.
- alkenyl group when the term “alkenyl group” is simply used, it includes both an "unsubstituted alkenyl group” and a "substituted alkenyl group”.
- substituted alkenyl group refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group” are replaced with a substituent.
- Specific examples of the "substituted alkenyl group” include the following "unsubstituted alkenyl group” (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B).
- the examples of the "unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” listed here are merely examples, and the "substituted alkenyl group” described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent.
- Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, A 2-butenyl group, and a 3-butenyl group.
- Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
- the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group” is an "unsubstituted alkynyl group."
- alkynyl group refers to an "unsubstituted alkynyl group” in which one or more hydrogen atoms have been replaced with a substituent.
- Specific examples of the "substituted alkynyl group” include the following "unsubstituted alkynyl group” (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.
- Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B).
- unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group” is an "unsubstituted cycloalkyl group”
- substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group” is a "substituted cycloalkyl group”.
- substituted cycloalkyl group refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group” are replaced with a substituent.
- Specific examples of the "substituted cycloalkyl group” include the following "unsubstituted cycloalkyl group” (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B).
- the examples of the "unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group” in the specific example group G6B are replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group” in the specific example group G6B is further replaced with a substituent.
- Unsubstituted cycloalkyl groups (specific example group G6A): A cyclopropyl group, A cyclobutyl group, Cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
- Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl group.
- G7 of the group represented by --Si(R 901 )(R 902 )(R 903 ) described in this specification include: -Si(G1)(G1)(G1), -Si (G1) (G2) (G2), -Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6)(G6)
- G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
- G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
- G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
- G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
- the multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.
- the multiple G2s in —Si(G1)(G2)(G2) are the same as or different from each other.
- the multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.
- the multiple G2s in —Si(G2)(G2)(G2) are the same as or different from each other.
- the multiple G3s in —Si(G3)(G3)(G3) are the same as or different from each other.
- the multiple G6s in —Si(G6)(G6)(G6) are the same as or different from each other.
- G8 of the group represented by -O-(R 904 ) described in this specification include: -O(G1), -O (G2), -O(G3) and -O(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group” described in specific example group G1. G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
- G9 A group represented by -S-(R 905 )
- Specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification include: -S (G1), -S (G2), -S(G3) and -S(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group” described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
- Specific examples (specific example group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification include: -N(G1)(G1), -N(G2)(G2), -N (G1) (G2), -N(G3)(G3), and -N(G6)(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group” described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
- G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
- G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
- the multiple G1s in -N(G1)(G1) are the same or different from each other.
- the multiple G2s in -N(G2)(G2) are the same or different from each other.
- the multiple G3s in -N(G3)(G3) are the same or different.
- the multiple G6s in -N(G6)(G6) are the same or different.
- halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- substituted or unsubstituted fluoroalkyl groups means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with fluorine atoms.
- the number of carbon atoms in the "unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification.
- substituted fluoroalkyl group means a group in which one or more hydrogen atoms in the "fluoroalkyl group” are replaced with a substituent.
- substituted fluoroalkyl group as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group” are further replaced with a substituent.
- substituents include the examples of groups in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with fluorine atoms.
- substituted or unsubstituted haloalkyl group means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
- the number of carbon atoms in the "unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification.
- substituted haloalkyl group means a group in which one or more hydrogen atoms in the "haloalkyl group” are replaced with a substituent.
- substituted haloalkyl group as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group” are further replaced with a substituent.
- substituents in the "substituted haloalkyl group” are further replaced with a substituent.
- Specific examples of the "unsubstituted haloalkyl group” include the examples of the group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
- Haloalkyl groups are sometimes referred to as halogenated alkyl groups.
- a specific example of the "substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
- the number of carbon atoms in the "unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
- Substituted or unsubstituted alkylthio group A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
- the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
- a specific example of the "substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
- the number of ring carbon atoms of the "unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
- a specific example of the "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
- the number of ring carbon atoms of the "unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
- a specific example of the "trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
- the multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.
- the number of carbon atoms in each alkyl group of the "trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.
- a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group” described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
- an “aralkyl group” is a group in which a hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one aspect of a “substituted alkyl group”.
- An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group”, and the number of carbon atoms of the "unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
- substituted or unsubstituted aralkyl group include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
- the substituted or unsubstituted aryl group described herein is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a o-terphenyl-4-yl group, a o-terphenyl-3-yl group, a o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a
- the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothi
- zadibenzothiophenyl group diazadibenzothiophenyl group
- (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group)
- (9-biphenylyl)carbazolyl group (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
- carbazolyl group is specifically any of the following groups:
- the (9-phenyl)carbazolyl group is specifically any of the following groups:
- dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.
- substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
- the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group".
- Specific examples of the "substituted or unsubstituted arylene group” include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in specific example group G1.
- Substituted or unsubstituted divalent heterocyclic group is, unless otherwise specified, a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group".
- Specific examples of the "substituted or unsubstituted divalent heterocyclic group” include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group” described in specific example group G2.
- the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group".
- Specific examples of the "substituted or unsubstituted alkylene group” include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group” described in specific example group G3.
- the substituted or unsubstituted arylene group described herein is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
- Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
- * represents a binding site.
- Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
- Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
- * represents a binding site.
- Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
- * represents a binding site.
- the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.
- Q 1 to Q 9 each independently represent a hydrogen atom or a substituent.
- Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
- the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other".
- the pair of adjacent two that constitutes one group includes the pair of R 921 and R 922 , the pair of R 922 and R 923 , the pair of R 923 and R 924 , the pair of R 924 and R 930 , the pair of R 930 and R 925 , the pair of R 925 and R 926 , the pair of R 926 and R 927 , the pair of R 927 and R 928 , the pair of R 928 and R 929 , and the pair of R 929 and R 921 .
- one or more pairs means that two or more pairs of the adjacent two or more pairs may simultaneously form a ring.
- the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
- a set of two or more adjacent rings forms a ring includes not only the case where a set of "two" adjacent rings is bonded as in the above example, but also the case where a set of "three or more adjacent rings is bonded.
- it means the case where R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , and a set of three adjacent rings (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and are condensed to the anthracene skeleton.
- the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105).
- ring Q A and ring Q C share R 922 .
- the "monocyclic ring” or “fused ring” formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even if “one of the pairs of adjacent two" forms a “monocyclic ring” or a “fused ring", the “monocyclic ring” or the “fused ring” can form a saturated ring or an unsaturated ring.
- the ring Q A and the ring Q B formed in the general formula (TEMP-104) are “monocyclic rings” or “fused rings", respectively.
- the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”.
- the ring Q A and the ring Q C in the general formula (TEMP-105) are fused rings by the fusion of the ring Q A and the ring Q C. If the ring Q A in the general formula (TMEP-104) is a benzene ring, the ring Q A is a monocyclic ring. When ring Q 1 A in the above general formula (TMEP-104) is a naphthalene ring, ring Q 1 A is a fused ring.
- the "unsaturated ring” includes aromatic hydrocarbon rings and aromatic heterocycles, as well as aliphatic hydrocarbon rings having an unsaturated bond in the ring structure, i.e., a double bond and/or a triple bond (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.).
- the "saturated ring” includes an aliphatic hydrocarbon ring having no unsaturated bond, or a non-aromatic heterocycle having no unsaturated bond.
- aromatic hydrocarbon ring examples include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom.
- aromatic heterocycle examples include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom.
- Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom.
- the ring QA formed by bonding R 921 and R 922 to each other in the general formula (TEMP-104) means a ring formed by the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and one or more arbitrary atoms.
- R 921 and R 922 form a ring QA
- the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms form a monocyclic unsaturated ring
- the ring formed by R 921 and R 922 is a benzene ring.
- the "arbitrary atom” is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
- the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below.
- the ring formed is a heterocycle.
- the "one or more any atoms" constituting the single ring or the fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.
- the "monocyclic ring” and the “condensed ring” the "monocyclic ring” is preferred.
- the "saturated ring” and the “unsaturated ring” the “unsaturated ring” is preferred.
- a "monocyclic ring” is preferably a benzene ring.
- the "unsaturated ring” is preferably a benzene ring.
- the "unsaturated ring” is preferably a benzene ring.
- one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted monocyclic ring” or “combine with each other to form a substituted or unsubstituted fused ring
- one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring” consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
- the substituent is, for example, the “optional substituent” described later.
- specific examples of the substituent are the substituents described in the above-mentioned section “Substituents described in this specification”.
- the substituent is, for example, the "optional substituent” described later.
- substituents in the case of "substituted or unsubstituted” are, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a group selected from the group consisting of an unsubstituted
- the two or more R 901 are the same or different from each other
- the two or more R 902 are present, the two or more R 902 are the same or different from each other
- the two or more R 903 are present, the two or more R 903 are the same or different from each other
- the two or more R 904 are present, the two or more R 904 are the same or different from each other
- the two or more R 905 are present, the two or more R 905 are the same or different from each other
- two or more R 906 are present, the two or more R 906 are the same or different from each other
- the two or more R 907 are present, the two or more R 907 are the same or different.
- the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 50 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
- the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 18 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
- any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.
- the optional substituent may further have a substituent.
- the substituent that the optional substituent further has is the same as the optional substituent described above.
- a numerical range expressed using "AA-BB” refers to a range that includes the number AA written before “AA-BB” as the lower limit and the number BB written after "AA-BB” as the upper limit.
- a compound according to one embodiment of the present invention is a compound represented by formula (1) or (2) described below.
- the compound according to one aspect of the present invention when used in an organic EL device, it can improve the device performance. In particular, by using the compound in one of the stacked light-emitting layers, it is possible to improve the device performance.
- the compound according to one embodiment of the present invention is represented by the following formula (1).
- One of R 101 to R 105 is a single bond bonded to a group represented by the following formula (A1).
- L A1 is, Single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, a substituted or unsubstituted terphenyldiyl group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthryldiyl group, a substituted or unsubstituted benzophenanthryldiyl group, a substituted or unsubstituted benzanthracenediyl group, a substituted or unsubstituted pyrenediyl group, a substituted or unsubstituted chrysenediy
- Ar A1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted fluorenyl group, a substitute
- nA1 is an integer of 0 to 3. When nA1 is 0, (L A1 ) nA1 is a single bond. When nA1 is 2 or 3, multiple L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the most distant from the dinaphthofuran skeleton. Multiple L A1 may be the same or different.
- One or more pairs of adjacent two or more of R 106 to R 112 and R 101 to R 105 that are not a single bond bonded to the group represented by formula (A1) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
- R 106 to R 112 which are not bonded to each other, and R 101 to R 105 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A1) each independently represent: It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A1).
- R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
- R 41 to R 45 and R 49 to R 51 may be the same or different.
- one of R 102 to R 105 is a single bond bonding to the group represented by formula (A1).
- one of R 102 , R 103 , and R 105 is a single bond bonding to the group represented by formula (A1). In one embodiment, one of R 103 and R 105 is a single bond bonding to the group represented by formula (A1). In one embodiment, R 102 is a single bond bonded to the group represented by formula (A1). In one embodiment, R 103 is a single bond bonded to the group represented by formula (A1). In one embodiment, R 105 is a single bond bonded to the group represented by formula (A1).
- L A1 is Single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzanthracenediyl group, a substituted or unsubstituted pyrenediyl group, It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
- L A1 is It is a single bond, or a substituted or unsubstituted phenylene group.
- Ar A1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthracenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
- Ar A1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthracenyl group; a substituted or unsubstituted pyrenyl group; It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
- the group represented by formula (A1) is a group represented by any one of the following formulas (A1-1) to (A1-7).
- nA1 and L A1 are as defined in formula (A1) above.
- R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently Hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
- the group represented by formula (A1) is a group represented by any one of formulas (A1-1) to (A1-5).
- the compound represented by formula (1) is a compound represented by any one of formulas (1-1) to (1-3) below. [In the formulas (1-1) to (1-3), nA1, L A1 , Ar A1 , and R 101 to R 112 are as defined in the formula (1).]
- the compound represented by formula (1) is a compound represented by formula (1-1) or formula (1-2).
- the compound represented by formula (1) is a compound represented by any one of formulas (1-11) to (1-19) below.
- nA1, L A1 , and R 101 to R 112 are as defined in formula (1).
- R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently Hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
- the compound represented by formula (1) is a compound represented by any one of formulas (1-11) to (1-14).
- R 101 to R 112 that are not single bonds are hydrogen atoms.
- R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently: Hydrogen atoms, Methyl group, It is a phenyl group or a naphthyl group.
- R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently a hydrogen atom, a methyl group, or a phenyl group.
- R A11 to R A14 and R A16 to R A19 are hydrogen atoms, and R A15 is a phenyl group.
- R A11 to R A19 are hydrogen atoms.
- R A21 to R A26 and R A28 to R A32 are hydrogen atoms.
- R A21 to R A26 and R A28 to R A31 are hydrogen atoms, and R A27 is a phenyl group.
- R A41 to R A49 and R A61 to R A71 are hydrogen atoms
- R A50 to R A51 and R A72 to R A73 are methyl groups.
- R A81 to R A89 are hydrogen atoms.
- R A91 to R A99 are hydrogen atoms.
- At least one of R A81 to R A89 which are hydrogen atoms is a deuterium atom.
- At least one of R A91 to R A99 which are hydrogen atoms is a deuterium atom.
- a hydrogen atom when a hydrogen atom is "a deuterium atom,” it means that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms in the hydrogen atom is greater than the natural abundance ratio.
- the fact that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms is greater than the natural abundance ratio can be confirmed using a nuclear magnetic resonance spectrometer.
- the substituent in the case of "substituted or unsubstituted" in formula (1) is an alkyl group having 1 to 50 carbon atoms, a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms;
- the substituent in the case of "substituted or unsubstituted" in formula (1) is an alkyl group having 1 to 18 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
- the compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions and raw materials that are suited to the target product.
- [Compound represented by formula (2)] The compound according to one embodiment of the present invention is represented by the following formula (2).
- One of R 201 to R 205 is a single bond bonded to a group represented by the following formula (A2).
- Ar A2 is It is a substituted or unsubstituted aryl group consisting of 5 or less rings and having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
- nA2 is an integer from 0 to 3. When nA2 is 0, (L A2 ) nA2 is a single bond. When nA2 is 2 or 3, multiple L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the most distant from the dinaphthofuran skeleton. Multiple L A2 may be the same or different.
- R 206 to R 212 and R 201 to R 205 that are not single bonds bonded to the group represented by formula (A2)
- one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
- R 206 to R 212 which are not bonded to each other, and R 201 to R 205 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A2) each independently represent: It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A2).
- R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
- R 41 to R 45 and R 49 to R 51 may be the same or different.
- the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms which are composed of 5 or less rings in Ar A2 are each a group which satisfies the following formula (T1). T 1 >1.81eV...(T1) (In formula (T1), T1 is the triplet energy of the group.)
- the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not identical to the group represented by formula (A2)" will be explained below. This includes cases where the “group represented by formula (A2)" and the “substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms” are different, where their chemical structural formulas (skeletons) are different, and where the chemical structural formulas (skeletons) are the same but contain different isotopes.
- An isotope means an atom with the same atomic number but a different number of neutrons. For example, benzene (C 6 H 6 ) and deuterated benzene (C 6 D 6 ) are different from each other.
- Consisting of one ring means that it is a monocyclic ring.
- a phenyl group consists of one ring.
- X rings are condensed or spiro-bonded polycyclic rings.
- substituted or unsubstituted when substituents are bonded to each other to form a ring and are condensed or spiro-bonded to a ring having the substituent, the ring formed by bonding the substituents to each other is also included in "X rings".
- the following naphthyl group is composed of two rings:
- the naphthyl group may have a substituent.
- benzofluorenyl group is composed of four rings:
- the benzofluorenyl group may have a substituent.
- spirobifluorenyl group is made up of six rings:
- “composed of five or fewer rings” means that it is a monocyclic ring, or a polycyclic ring in which two, three, four, or five rings are fused or spiro-linked.
- the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and being composed of 5 or less rings, and the substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in Ar A2 are each groups that satisfy the following formula (T1)." will be explained.
- T 1 >1.81eV...(T1) (In formula (T1), T1 is the triplet energy of the group.)
- each of the L A2 which are substituted or unsubstituted arylene groups having 6 to 21 ring carbon atoms or substituted or unsubstituted divalent oxygen-containing heterocyclic groups having 5 to 30 ring atoms satisfies the above formula (T1).
- T1 the above formula (T1)
- the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms constituted by 5 or less rings in Ar A2 are each a group satisfying the following formula (T2), each a group satisfying the following formula (T3), each a group satisfying the following formula (T4), or each a group satisfying the following formula (T5).
- T 1 >1.85eV...(T5) (wherein T1 is the triplet energy of the group.)
- the upper limit of T1 is not particularly limited, and is, for example, 2.20 eV, 2.60 eV, 3.00 eV, or 3.40 eV.
- T1 in the formulas (T1) to (T5) is calculated by the method described in the Examples.
- one of R 202 to R 205 is a single bond bonding to the group represented by formula (A2).
- one of R 202 , R 203 , and R 205 is a single bond bonding to the group represented by formula (A2).
- one of R 203 and R 205 is a single bond bonding to the group represented by formula (A2).
- L A2 is Single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzanthracenediyl group, a substituted or unsubstituted pyrenediyl group, It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
- L A2 is It is a single bond, or a substituted or unsubstituted phenylene group.
- Ar A2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
- Ar A2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
- the group represented by formula (A2) is a group represented by any one of the following formulas (A2-1) to (A2-7).
- nA2 and L A2 are as defined in formula (A2) above.
- R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently Hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
- the compound represented by formula (2) is a compound represented by any one of formulas (2-1) to (2-3) below. [In the formulas (2-1) to (2-3), nA2, L A2 , Ar A2 , and R 201 to R 212 are as defined in the formula (2).]
- the compound represented by formula (2) is a compound represented by formula (2-1) or formula (2-2).
- the compound represented by formula (2) is a compound represented by any one of the following formulas (2-11) to (2-19).
- nA2, L A2 and R 201 to R 212 are as defined in formula (2) above.
- R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently Hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
- the compound represented by formula (2) is a compound represented by any one of formulas (2-11) to (2-14).
- R 201 to R 212 that are not single bonds are hydrogen atoms.
- R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently Hydrogen atoms, Methyl group, It is a phenyl group or a naphthyl group.
- R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently a hydrogen atom, a methyl group, or a phenyl group.
- R A111 to R A114 and R A116 to R A119 are hydrogen atoms, and R A115 is a phenyl group.
- R A111 to R A119 are hydrogen atoms.
- R A121 to R A126 and R A128 to R A132 are hydrogen atoms.
- R A121 to R A126 and R A128 to R A131 are hydrogen atoms, and R A127 is a phenyl group.
- R A141 to R A149 and R A161 to R A171 are hydrogen atoms, and R A150 to R A151 and R A172 to R A173 are methyl groups.
- R A181 to R A189 are hydrogen atoms.
- R A191 to R A199 are hydrogen atoms.
- At least one of R A181 to R A189 which are hydrogen atoms is a deuterium atom.
- At least one of R A191 to R A199 which are hydrogen atoms is a deuterium atom.
- a hydrogen atom when a hydrogen atom is "a deuterium atom,” it means that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms in the hydrogen atom is greater than the natural abundance ratio.
- the fact that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms is greater than the natural abundance ratio can be confirmed using a nuclear magnetic resonance spectrometer.
- the substituent in the case of "substituted or unsubstituted" in formula (2) is an alkyl group having 1 to 50 carbon atoms, a group selected from the group consisting of an aryl group having 6 to 13 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms;
- the substituent in the case of "substituted or unsubstituted" in formula (2) is an alkyl group having 1 to 18 carbon atoms,
- the group is selected from the group consisting of an aryl group having 6 to 13 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
- the compound represented by formula (2) can be synthesized by following the examples and using known alternative reactions and raw materials that are appropriate for the target product.
- the compound according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material used in the light-emitting layer of an organic EL device.
- An organic EL element according to one embodiment of the present invention will be described.
- An organic EL element according to one aspect of the present invention includes a cathode, an anode, and an emitting layer disposed between the cathode and the anode, the emitting layer including a first emitting layer and a second emitting layer, and the first emitting layer includes a compound represented by formula (3) described below.
- the organic EL element according to one aspect of the present invention has the above-mentioned configuration, which allows for improved performance.
- An organic EL element 1 includes a substrate 2, an anode 3, an emitting layer 5, a cathode 10, a hole transporting region 4 between the anode 3 and the emitting layer 5, and an electron transporting region 6 between the emitting layer 5 and the cathode 10.
- the light-emitting layer 5 has a laminated structure and includes at least a first light-emitting layer and a second light-emitting layer.
- Representative element configurations of the organic EL element of the present invention include: (1) anode/light-emitting layer/cathode (2) anode/hole-injection layer/light-emitting layer/cathode (3) anode/light-emitting layer/electron-injection and transport layer/cathode (4) anode/hole-injection layer/light-emitting layer/electron-injection and transport layer/cathode (5) anode/organic semiconductor layer/light-emitting layer/cathode (6) anode/organic semiconductor layer/electron-blocking layer/light-emitting layer/cathode (7) anode/organic semiconductor layer/light-emitting layer/adhesion-improving layer/cathode (8) anode/hole-injection and transport layer/light-emitting layer/ Examples of structures include electron injection/transport layer/cathode (9) anode/insulating layer/light-emitting layer/insulating layer/cath
- the positions at which the first light-emitting layer and the second light-emitting layer are formed are not limited.
- the light-emitting layer has the first light-emitting layer and the second light-emitting layer in this order from the anode side.
- the first light-emitting layer and the second light-emitting layer are directly adjacent.
- hole injection/transport layer means “at least one of a hole injection layer and a hole transport layer”
- electron injection/transport layer means “at least one of an electron injection layer and an electron transport layer.”
- the organic EL element according to one aspect of the present invention has a hole transport layer between the anode and the light-emitting layer.
- the organic EL element according to one aspect of the present invention has an electron transport layer between the cathode and the light-emitting layer.
- the first light-emitting layer contains a compound represented by the following formula (3).
- One of R 301 to R 305 is a single bond bonded to a group represented by the following formula (A3).
- L A3 is, Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
- Ar A3 is It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.
- nA3 is an integer from 0 to 3. When nA3 is 0, (L A3 ) nA3 is a single bond. When nA3 is 2 or 3, multiple L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the most distant from the dinaphthofuran skeleton. Multiple L A3 may be the same or different.
- R 306 to R 312 and R 301 to R 305 which are not single bonds bonded to the group represented by formula (A3), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
- R 306 to R 312 which are not bonded to each other, and R 301 to R 305 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A3) each independently represent: a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that is not the same as the group represented by formula (A3).
- one of R 302 to R 305 is a single bond bonding to the group represented by formula (A3).
- one of R 302 , R 303 , and R 305 is a single bond bonding to the group represented by formula (A3).
- one of R 303 and R 305 is a single bond bonding to the group represented by formula (A3).
- L A3 is Single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzanthracenediyl group, a substituted or unsubstituted pyrenediyl group, It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
- L A3 is It is a single bond, or a substituted or unsubstituted phenylene group.
- Ar A3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
- Ar A3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
- the group represented by formula (A3) is a group represented by any one of the following formulas (A3-1) to (A3-7). [In formulas (A3-1) to (A3-7), nA3 and L A3 are as defined in formula (A3).
- R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently Hydrogen atom, an alkyl group having 1 to 50 carbon atoms, a haloalkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, an arylthio group having 6 to 50 ring carbon atoms, an aralkyl group having 7 to 50 carbon atoms, -Si(R 941 )(R 942 )(R 9
- R 941 to R 953 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms. When two or more of R 941 to R 953 are present, each of the two or more R 941 to R 953 may be the same or different.
- the group represented by formula (A3) is a group represented by any one of formulas (A3-1) to (A3-5).
- the compound represented by formula (3) is a compound represented by any one of formulas (3-1) to (3-3) below.
- nA3, L A3 , Ar A3 , and R 301 to R 312 are as defined in the formula (1).
- the compound represented by formula (3) is a compound represented by formula (3-1) or formula (3-2).
- the compound represented by formula (3) is a compound represented by any one of formulas (3-11) to (3-19) below.
- nA3, L A3 and R 301 to R 312 are as defined in formula (3).
- R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently Hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, a haloalkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6
- R 941 to R 953 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms. When two or more of R 941 to R 953 are present, each of the two or more R 941 to R 953 may be the same or different.
- the compound represented by formula (3) is a compound represented by any one of formulas (3-11) to (3-14).
- R 301 to R 312 that are not single bonds are hydrogen atoms.
- R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , and R A261 to R A273 are each independently: Hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
- R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , and R A261 to R A273 are each independently: Hydrogen atom, an alkyl group having 1 to 18 carbon atoms, It is an aryl group having 6 to 18 ring carbon atoms, or a monovalent heterocyclic group having 5 to 18 ring atoms.
- R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently: Hydrogen atoms, Methyl group, It is a phenyl group or a naphthyl group.
- R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently a hydrogen atom, a methyl group, or a phenyl group.
- R A211 to R A214 and R A216 to R A219 are hydrogen atoms
- R A215 is a phenyl group.
- R A211 to R A219 are hydrogen atoms.
- R A221 to R A226 and R A228 to R A232 are hydrogen atoms.
- R A221 to R A226 and R A228 to R A231 are hydrogen atoms, and R A227 is a phenyl group.
- R A241 to R A249 and R A261 to R A271 are hydrogen atoms
- R A250 to R A251 and R A272 to R A273 are methyl groups.
- R A281 to R A289 are hydrogen atoms.
- R A291 to R A299 are hydrogen atoms.
- At least one of R A281 to R A289 which are hydrogen atoms is a deuterium atom.
- At least one of R A291 to R A299 which are hydrogen atoms is a deuterium atom.
- a hydrogen atom when a hydrogen atom is "a deuterium atom,” it means that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms in the hydrogen atom is greater than the natural abundance ratio.
- the fact that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms is greater than the natural abundance ratio can be confirmed using a nuclear magnetic resonance spectrometer.
- R 41 to R 53 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms. When two or more of R 41 to R 53 are present, each of the two or more R 41 to R 53 may be the same or different.
- the substituent in the case of “substituted or unsubstituted” in the formula (3) is an alkyl group having 1 to 50 carbon atoms, It is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
- the compound represented by formula (3) is a compound represented by formula (1). In one embodiment, the compound represented by formula (3) is a compound represented by formula (2).
- the compound represented by formula (3) can be synthesized by following the examples and using known alternative reactions and raw materials that are appropriate for the target product.
- Specific examples of the compound represented by formula (3) include the specific examples of the compounds represented by formula (1) or formula (2) described above. These are merely examples, and the compound represented by formula (3) is not limited to the specific examples of the compounds represented by formula (1) or formula (2) described above.
- the first light-emitting layer contains a compound represented by formula (3) above and a second compound.
- the compound represented by the formula (3) and the second compound are different from each other.
- the second compound is an emissive material. In one embodiment, the second compound is a fluorescent compound. In one embodiment, the second compound is a compound that exhibits emission having a maximum fluorescent emission peak wavelength of 430 nm or more and 480 nm or less. In this specification, the maximum fluorescent emission peak wavelength may be referred to as the maximum fluorescent emission peak wavelength.
- the maximum fluorescence emission peak wavelength refers to the maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound to be measured is dissolved at a concentration of 10 ⁇ 6 mol/L or more and 10 ⁇ 5 mol/L or less.
- the measurement device may be a fluorescence spectrum measuring device (device name: FP-8300, manufactured by JASCO Corporation). Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.
- Examples of the second compound include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing boron atoms, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and nap
- the second compound may be, for example, one or more compounds selected from the group consisting of a compound represented by the following formula (D1), a compound represented by the following formula (D2), a compound represented by the following formula (D3), and a compound represented by the following formula (D4).
- D1 a compound represented by the following formula
- D2 a compound represented by the following formula
- D3 a compound represented by the following formula
- D4 a compound represented by the following formula (D4).
- Each Z is independently CRa or a nitrogen atom.
- Ring A1 and ring A2 each independently represent It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
- n21 and n22 each independently represent 0, 1, 2, 3, or 4.
- one or more pairs of adjacent two or more of the plurality of Rb's are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
- one or more pairs of adjacent two or more of the plurality of Rc's are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
- Ra, Rb, and Rc that are not bonded to each other are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- R 901 to R 907 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- each of the two or more R 901 to R 907 may be the same or different.
- Examples of the "aromatic hydrocarbon ring" of ring A1 and ring A2 include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms".
- the "aromatic hydrocarbon ring" of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of formula (D1) as ring-forming atoms.
- Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted aryl group” described in specific example group G1.
- Examples of the “heterocycle” of ring A1 and ring A2 include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocycle group having 5 to 50 ring atoms".
- the "heterocycle” of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of formula (D1) as ring-forming atoms.
- Specific examples of the “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted heterocyclic group” described in specific example group G2.
- Rb is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A1, or any of the atoms forming the heterocyclic ring as ring A1.
- Rc is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A2, or any of the atoms forming the heterocycle as ring A2.
- At least one of Ra, Rb, and Rc is a group represented by the following formula (D1a): In one embodiment, at least two of Ra, Rb, and Rc are a group represented by the following formula (D1a).
- LD101 is, Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
- Ar D101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (D1b): (In formula (D1b), L D102 and L D103 are each independently Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
- a pair consisting of Ar D102 and Ar D103 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
- Ar D102 and Ar D103 which are not bonded to each other are each independently A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- R 901 to R 907 are each independently It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- the compound represented by formula (D1) can be synthesized by using known reactions and raw materials that are suited to the target product.
- R D201 to R D207 and R D211 to R D217 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
- R D201 to R D207 and R D211 to R D217 that are not bonded to each other each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic
- R and R are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- R 901 to R 907 are
- One of the groups consisting of two or more adjacent pairs of R D201 to R D207 and R D211 to R D217 is, for example, a combination such as a group consisting of R D201 and R D202 , a group consisting of R D202 and R D203 , a group consisting of R D203 and R D204 , a group consisting of R D205 and R D206 , a group consisting of R D206 and R D207 , or a group consisting of R D201 , R D202 and R D203 .
- At least one of R D201 -R D207 and R D211 -R D217 is --N(R 906 )(R 907 ).
- At least two of R D201 -R D207 and R D211 -R D217 are --N(R 906 )(R 907 ).
- At least one of R D201 to R D207 is --N(R 906 )(R 907 ). In one embodiment, at least one of R D211 to R D217 is --N(R 906 )(R 907 ).
- At least one of R D201 -R D207 , and at least one of R D211 -R D217 are each independently -N(R 906 )(R 907 ).
- R D201 -R D207 and R D211 -R D217 that are not —N(R 906 )(R 907 ) are each independently Hydrogen atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- the compound represented by formula (D2) can be synthesized by using known reactions and raw materials that are suited to the target product.
- Ring a, ring b and ring c each independently represent It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
- R D301 and R D302 each independently bond to the ring a, ring b or ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.
- R and R which do not form a substituted or unsubstituted heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- the a, b, and c rings are fused to a central fused two-ring structure of formula (D3) consisting of a boron atom, two nitrogen atoms, and seven carbon atoms.
- the "aromatic hydrocarbon rings" of ring a, ring b and ring c have the same structure as the compound in which a hydrogen atom has been introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms".
- the "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of formula (D3) as ring-forming atoms.
- the "aromatic hydrocarbon ring” of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of formula (D3) as ring-forming atoms.
- substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted aryl group” described in specific example group G1.
- Examples of the "heterocyclic ring" of ring a, ring b, and ring c include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group having 5 to 50 ring atoms”.
- the "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of formula (D3) as ring-forming atoms.
- the "heterocycle” of ring b and ring c contains two carbon atoms on the central fused bicyclic structure of formula (D3) as ring-forming atoms.
- Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
- R D301 and R D302 may each independently bond to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle.
- the heterocycle in this case includes the nitrogen atom on the central fused two-ring structure of the formula (D3).
- the heterocycle in this case may include a heteroatom other than a nitrogen atom.
- R D301 or R D302 bonded to the ring a, ring b, or ring c means that an atom constituting the ring a, ring b, or ring c is bonded to an atom constituting R D301 or R D302 .
- R D301 may bond to the ring a to form a two-ring fused, three-ring fused, four-ring fused, or five-ring or more fused nitrogen-containing heterocycle in which the ring containing R D301 is fused to the ring a.
- Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two-ring or more fused heterocyclic group in the specific example group G2. The above applies when R D301 is bonded to ring b, when R D302 is bonded to ring a, and when R D302 is bonded to ring c.
- the ring a, ring b, and ring c in the formula (D3) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms. In one embodiment, the ring a, the ring b, and the ring c in the formula (D3) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
- R and R in formula (D3) are each independently It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- R D301 and R D302 in the formula (D3) each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- the compound represented by formula (D3) is a compound represented by formula (D32): (In formula (D32), R D301A combines with one or more selected from the group consisting of R D311 and R D321 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R D302A combines with one or more selected from the group consisting of R D313 and R D314 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R D301A and R D302A which do not form a substituted or unsubstituted heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- One or more pairs of adjacent two or more of R D311 to R D321 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
- R D311 to R D321 which do not form a substituted or unsubstituted heterocycle, do not form a monocycle, and do not form a fused ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon
- R D301A and R D302A in the formula (D32) correspond to R D301 and R D302 in the formula (D3), respectively.
- R D301A and R D311 may be bonded to form a nitrogen-containing heterocycle having two rings, three rings, four rings, or five or more rings, in which a ring containing them is fused with a benzene ring corresponding to the ring a.
- Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing heterocyclic group having two or more rings in specific example group G2. The same applies when R D301A and R D321 are bonded, when R D302A and R D313 are bonded, and when R D302A and R D314 are bonded.
- one or more of the sets of two or more adjacent ones of R D311 to R D321 are They may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted fused ring.
- R and R may be bonded to a 6-membered ring to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed with the 6-membered ring to which they are bonded.
- the condensed ring thus formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.
- R D311 to R D321 that do not contribute to ring formation are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- R D311 to R D321 that do not contribute to ring formation are each independently Hydrogen atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- R D311 to R D321 that do not contribute to ring formation are each independently It is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- R D311 to R D321 that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; At least one of R D311 to R D321 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- the compound represented by formula (D32) is a compound represented by formula (D33):
- R D331 combines with R D346 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R D333 combines with R D347 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R D334 combines with R D351 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R D341 combines with R D342 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- One or more pairs of adjacent two or more of R D331 to R D351 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
- R D331 to R D351 that are not bonded to each other are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring
- R D331 may be bonded to R D346 to form a substituted or unsubstituted heterocycle.
- R D331 and R D346 may be bonded to form a nitrogen-containing heterocycle having three or more condensed rings in which the benzene ring to which R D346 is bonded, the ring containing N, and the benzene ring corresponding to the a ring are condensed.
- Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing heterocyclic group having three or more condensed rings in the specific example group G2. The same applies when R D333 and R D347 are bonded, when R D334 and R D351 are bonded, and when R D341 and R D342 are bonded.
- R D331 to R D351 that do not contribute to ring formation are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- R D331 to R D351 that do not contribute to ring formation are each independently Hydrogen atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- R D331 to R D351 that do not contribute to ring formation are each independently It is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- R D331 to R D351 that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; At least one of R D331 to R D351 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- the compound represented by formula (D33) is a compound represented by formula (D33A):
- R D361 is Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- R D362 to R D365 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- R D361 to R D365 are each independently: It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- R D361 to R D365 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- the compound represented by formula (D33) is a compound represented by formula (D33B):
- R D371 and R D372 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- R D373 to R D375 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- R 906 and R 907 are as defined in formula (D1).
- the compound represented by formula (D33) is a compound represented by the following formula (D33B'):
- R D372 to R D375 are as defined in formula (D33B) above.
- R D371 to R D375 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- RD372 is Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
- R D371 and R D373 to R D375 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- the compound represented by formula (D33) is a compound represented by formula (D33C):
- R and R are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- R D383 to R D386 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- the compound represented by formula (D33) is a compound represented by the following formula (D33C'):
- R D383 to R D386 are as defined in formula (D33C) above.
- R D381 to R D386 are each independently: It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- R D381 to R D386 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- the compound represented by formula (D3) can be produced by first linking ring a, ring b, and ring c with a first linking group (a group containing N-R D301 and a group containing N-R D302 ) to produce an intermediate (first reaction), and then linking ring a, ring b, and ring c with a second linking group (a group containing a boron atom) to produce a final product (second reaction).
- amination reaction such as the Bachbult-Hartwig reaction can be applied.
- a tandem hetero Friedel-Crafts reaction or the like can be applied.
- the compound represented by formula (D3) can be synthesized by using known reactions and raw materials that are suited to the target product.
- R D4 At least one pair of R D401 and R D402 , R D402 and R D403 , and R D403 and R D404 are bonded to each other to form a divalent group represented by the following formula (D42). At least one pair of R D405 and R D406 , R D406 and R D407 , and R D407 and R D408 are bonded to each other to form a divalent group represented by the following formula (D43). At least one of R D401 to R D404 and R D411 to R D414 that do not form a divalent group represented by formula (D42) is a monovalent group represented by formula (D44) below.
- At least one of R D405 to R D408 and R D421 to R D424 that do not form a divalent group represented by formula (D43) is a monovalent group represented by formula (D44) below.
- XD4 is an oxygen atom, a sulfur atom, or NR D409 .
- R D401 to R D408 which do not form a divalent group represented by formula (D42) or formula (D43) and are not a monovalent group represented by formula (D44), R D411 to R D414 and R D421 to R D424 which are not a monovalent group represented by formula (D44), and R D409 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ),
- Ar D401 and Ar D402 are each independently It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
- L D401 to L D403 each independently represent Single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms
- the divalent linking group is formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
- L D401 is bonded to the ring structure represented by formula (D4), the group represented by formula (D42), or the group represented by formula (D43).
- the positions at which the divalent group represented by the formula (D42) and the divalent group represented by the formula (D43) are formed are not particularly limited, and the groups can be formed at any possible position of R D401 to R D408 .
- the compound represented by formula (D4) can be synthesized by using known reactions and raw materials that are suited to the target product.
- the first light-emitting layer contains the compound represented by the above formula (3) as a host material (sometimes referred to as a matrix material). In one embodiment, the first light-emitting layer further comprises a dopant material. In one embodiment, the first light-emitting layer includes the second compound as a dopant material (also sometimes referred to as a guest material, an emitter, or an emissive material).
- the first light-emitting layer contains more than 1.1 weight percent, 1.2 weight percent or more, or 1.5 weight percent or more of the dopant material based on the total weight of the first light-emitting layer. In one embodiment, the first light-emitting layer contains no more than 10 weight percent, no more than 7 weight percent, or no more than 5 weight percent of the dopant material based on the total weight of the first light-emitting layer.
- the first light-emitting layer contains 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more of the host material based on the total weight of the first light-emitting layer. In one embodiment, the first light-emitting layer contains a host material in an amount of up to 99% by weight of the total weight of the first light-emitting layer.
- the first light-emitting layer may contain materials other than the host material and the dopant material.
- the first light-emitting layer may contain only one type of host material, or may contain two or more types.
- the first light-emitting layer may contain only one type of dopant material, or may contain two or more types.
- the second light-emitting layer contains at least one compound different from the first light-emitting layer.
- the second light-emitting layer contains a host material.
- the host material in addition to the compound represented by the above formula (3), for example, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative, or 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative can be used.
- the second host material is a different compound than the first host material contained in the first light-emitting layer.
- the second light-emitting layer further includes a dopant material.
- the dopant material for example, the second compound described above can be used.
- a known phosphorescent material can also be used as the dopant material.
- the dopant material of the second light-emitting layer is a different compound than the dopant material of the first light-emitting layer.
- the dopant material of the second light-emitting layer is the same compound as the dopant material of the first light-emitting layer.
- the second light-emitting layer contains more than 1.1 weight percent, 1.2 weight percent or more, or 1.5 weight percent or more of the dopant material based on the total weight of the second light-emitting layer. In one embodiment, the second light-emitting layer contains no more than 10 weight percent, no more than 7 weight percent, or no more than 5 weight percent of the dopant material based on the total weight of the second light-emitting layer.
- the second light-emitting layer contains 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more of the host material based on the total weight of the second light-emitting layer. In one embodiment, the second light-emitting layer contains a host material in an amount of up to 99% by weight of the total weight of the second light-emitting layer.
- the second light-emitting layer may contain materials other than the host material and the dopant material.
- the second light-emitting layer may contain only one type of host material, or may contain two or more types.
- the second light-emitting layer may contain only one type of dopant material, or may contain two or more types.
- the second light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer. In one embodiment, the second light-emitting layer is a fluorescent-type light-emitting layer.
- the organic EL element according to one embodiment of the present invention, conventionally known materials and element configurations can be applied, so long as the effects of the present invention are not impaired, except that the first light-emitting layer contains the compound represented by formula (3).
- the substrate is used as a support for the light-emitting element.
- glass, quartz, plastic, etc. can be used as the substrate.
- a flexible substrate may also be used.
- a flexible substrate is a substrate that can be bent (flexible), and examples of the flexible substrate include plastic substrates made of polycarbonate and polyvinyl chloride.
- anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more).
- a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function specifically, 4.0 eV or more.
- Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene.
- ITO indium oxide-tin oxide
- ITO indium oxide-tin oxide containing silicon or silicon oxide
- indium oxide-zinc oxide silicon oxide
- tungsten oxide indium oxide containing zinc oxide
- graphene graphene
- Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride).
- the hole injection layer is a layer containing a substance having a high hole injection property.
- the substance having a high hole injection property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, and polymer compounds (oligomers, dendrimers, polymers, etc.).
- the hole transport layer is a layer containing a substance with high hole transport properties.
- an aromatic amine compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
- PVK poly(N-vinylcarbazole)
- PVTPA poly(4-vinyltriphenylamine)
- other substances may be used as long as they have a higher hole transport property than electron transport properties.
- the layer containing the substance with high hole transport properties may be not only a single layer, but also a laminate of two or more layers made of the above substances.
- the light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used.
- a compound represented by formula (D1), a compound represented by formula (D2), a compound represented by formula (D3), and a compound represented by formula (D4) as well as a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence can be used.
- a fluorescent compound is a compound that can emit light from a singlet excited state
- a phosphorescent compound is a compound that can emit light from a triplet excited state.
- blue-based fluorescent materials examples include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives.
- green-based fluorescent materials examples include aromatic amine derivatives.
- red-based fluorescent materials examples include tetracene derivatives and diamine derivatives.
- blue phosphorescent materials usable in the light-emitting layer metal complexes such as iridium complexes, osmium complexes, platinum complexes, etc. are used.
- iridium complexes As green phosphorescent materials usable in the light-emitting layer, iridium complexes, etc. are used. As red phosphorescent materials usable in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, europium complexes, etc. are used.
- the light-emitting layer may have a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material).
- a substance for dispersing the highly luminescent substance various substances can be used in addition to the above-described materials used in the present invention (the compound represented by formula (1), the compound represented by formula (2), and the compound represented by formula (3)). It is preferable to use a substance having a lower lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the highly luminescent substance.
- LUMO level lowest unoccupied molecular orbital level
- HOMO level lower highest occupied molecular orbital level
- a substance (host material) for dispersing a highly luminescent substance 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative; or 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative.
- a delayed fluorescent (thermally activated delayed fluorescent) compound can be used as the host material.
- the light-emitting layer contains the material used in the present invention described above and a delayed fluorescent host compound.
- the light-emitting layer may or may not contain the above-mentioned other substances in addition to the materials used in the present invention described above.
- the electron transport layer is a layer containing a substance having high electron transport properties, and may be formed using 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound.
- a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex
- a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound.
- the electron injection layer is a layer containing a substance with high electron injection properties, and may be made of a metal complex compound such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), or 8-hydroxyquinolinolato-lithium (Liq), an alkali metal such as lithium oxide (LiO x ), an alkaline earth metal, or a compound thereof.
- a metal complex compound such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), or 8-hydroxyquinolinolato-lithium (Liq)
- an alkali metal such as lithium oxide (LiO x ), an alkaline earth metal, or a compound thereof.
- cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a small work function (specifically, 3.8 eV or less).
- a cathode material include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
- the cathode is usually formed by a vacuum deposition method or a sputtering method. When a silver paste or the like is used, a coating method or an inkjet method can be used.
- the cathode can be formed using various conductive materials, such as aluminum, silver, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function.
- an electron blocking layer Adjacent to the light-emitting layer, an electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc. may be provided.
- the electron blocking layer is a layer having a function of preventing electrons from leaking from the light-emitting layer to the hole transport layer.
- the hole blocking layer is a layer having a function of preventing holes from leaking from the light-emitting layer to the electron transport layer.
- the exciton blocking layer is a layer having a function of preventing excitons generated in the light-emitting layer from diffusing to adjacent layers and confining the excitons within the light-emitting layer.
- the thickness of each layer is not particularly limited, but in general, a thickness in the range of several nm to 1 ⁇ m is preferable in order to suppress defects such as pinholes, keep the applied voltage low, and improve the light emission efficiency.
- each layer is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used.
- Each layer, such as the light-emitting layer can be formed by known methods such as vacuum deposition, molecular beam deposition (MBE), or coating methods such as dipping a solution dissolved in a solvent, spin coating, casting, bar coating, and roll coating.
- MBE molecular beam deposition
- An electronic device includes the organic EL element according to an aspect of the present invention.
- Specific examples of electronic devices include display components such as organic EL panel modules, display devices for televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps.
- the tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows.
- the slope of this tangent decreases and then increases repeatedly.
- the tangent drawn at the point where the slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values of 0.2 or less are not included in the maximum values on the longest wavelength side.
- the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side was drawn as follows. When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, a tangent to each point on the curve toward the long wavelength side was considered. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) was taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
- a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum was not included in the maximum value on the shortest wavelength side described above, and a tangent drawn at a point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side was defined as a tangent to the rising edge on the short wavelength side of the phosphorescence spectrum.
- the phosphorescence was measured using a Hitachi High-Tech F-7100 spectrofluorophotometer.
- Example 1 Preparation of Organic EL Element> An organic EL device was fabricated as follows. A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and compound HI1 was deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a first hole transport layer with a thickness of 5 nm.
- the compound HT1 was evaporated to form a second hole transport layer having a thickness of 80 nm.
- the compound EBL1 was evaporated to form a third hole transport layer having a thickness of 10 nm.
- the compound BH1-1 (host material) and the compound BD1 (dopant material) were co-deposited so that the ratio of the compound BD1 was 2 mass %, to form a first light-emitting layer with a thickness of 5 nm.
- the compound BH2-1 (host material) and the compound BD1 (dopant material) were co-deposited so that the ratio of the compound BD1 was 2 mass %, to form a second emitting layer having a thickness of 20 nm.
- the compound HBL1 was evaporated to form a first electron transport layer having a thickness of 10 nm.
- a compound ET1 was deposited by vapor deposition to form a second electron transport layer having a thickness of 15 nm.
- LiF was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
- Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 80 nm.
- the device configuration of the organic EL device of Example 1 is roughly shown as follows. ITO(130)/HI1(5)/HT1(80)/EBL1(10)/BH1-1:BD1(5:2%)/BH2-1:BD1(20:2%)/HBL1(10)/ET1(15)/LiF(1)/Al(80)
- the numbers in parentheses indicate the film thickness (unit: nm). Moreover, the percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the layer.
- CIE 1931 chromaticity The CIE 1931 chromaticity coordinates (x, y) when a voltage was applied to the organic EL element so that the current density was 10 mA/cm 2 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).
- Table 3 shows that the organic EL elements of Examples 1 to 13, which use a first compound having a structure represented by formula (1) as a first host material, achieve a lower device voltage and suppress deterioration in chromaticity compared to the organic EL element of Comparative Example 1, which uses BH1-Ref1.
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Abstract
The present invention provides a compound represented by formula (1). [In formula (1), one of R101 to R105 is a single bond that binds with a group represented by formula (A1).]
Description
本発明は、新規化合物及びそれを用いた有機エレクトロルミネッセンス素子に関する。
The present invention relates to a novel compound and an organic electroluminescence device using the compound.
有機エレクトロルミネッセンス素子（以下、有機ＥＬ素子ともいう。）に電圧を印加すると、陽極から正孔が、また陰極から電子が、それぞれ発光層に注入される。そして、発光層において、注入された正孔と電子とが再結合し、励起子が形成される。
When a voltage is applied to an organic electroluminescence element (hereinafter also referred to as an organic EL element), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to form excitons.
従来の有機ＥＬ素子は素子性能が未だ十分ではなかった。素子性能を高めるべく有機ＥＬ素子に用いる材料の改良は徐々に進められているが（特許文献１～６）、さらなる高性能化が求められている。
The performance of conventional organic EL elements is still insufficient. Although improvements to the materials used in organic EL elements have been gradually made to enhance element performance (Patent Documents 1 to 6), further improvements in performance are required.
本発明の目的は、高性能な有機ＥＬ素子及び当該有機ＥＬ素子を実現可能な化合物を提供することである。
The object of the present invention is to provide a high-performance organic EL element and a compound capable of realizing such an organic EL element.
本発明によれば、以下の化合物等が提供される。
１．下記式（１）で表される化合物。
［式（１）中、
Ｒ１０１～Ｒ１０５のうち１つは、下記式（Ａ１）で表される基と結合する単結合である。
（式（Ａ１）中、
ＬＡ１は、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のビフェニルジイル基、
置換もしくは無置換のターフェニルジイル基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のフェナントリルジイル基、
置換もしくは無置換のベンゾフェナントリルジイル基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のクリセンジイル基、
置換もしくは無置換のベンゾクリセンジイル基、
置換もしくは無置換のトリフェニレンジイル基、
置換もしくは無置換のベンゾトリフェニレンジイル基、
置換もしくは無置換のフルオレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、
置換もしくは無置換のジベンゾフルオレンジイル基、
置換もしくは無置換のナフトフルオレンジイル基、
置換もしくは無置換のフルオランテンジイル基、
置換もしくは無置換のベンゾフルオランテンジイル基、
置換もしくは無置換のペリレンジイル基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ１は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のビフェニル基、
置換もしくは無置換のターフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のフェナントリル基、
置換もしくは無置換のベンゾフェナントリル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のクリセニル基、
置換もしくは無置換のベンゾクリセニル基、
置換もしくは無置換のトリフェニレニル基、
置換もしくは無置換のベンゾトリフェニレニル基、
置換もしくは無置換のフルオレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトフルオレニル基、
置換もしくは無置換のフルオランテニル基、
置換もしくは無置換のベンゾフルオランテニル基、
置換もしくは無置換のペリレニル基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ１は０～３の整数である。
ｎＡ１が０である場合、（ＬＡ１）ｎＡ１は単結合である。
ｎＡ１が２又は３である場合、複数のＬＡ１は互いに直列状に連結し、ＡｒＡ１は、ジナフトフラン骨格から最も離れたＬＡ１に結合する。複数のＬＡ１は同一でもよく、異なってもよい。）
Ｒ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではないＲ１０１～Ｒ１０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではなく、互いに結合しないＲ１０１～Ｒ１０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ１）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。］
２．下記式（２）で表される化合物。
［式（２）中、
Ｒ２０１～Ｒ２０５のうち１つは、下記式（Ａ２）で表される基と結合する単結合である。
（式（Ａ２）中、
ＬＡ２は、
単結合、
置換もしくは無置換の環形成炭素数６～２１のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ２は、
５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ２は０～３の整数である。
ｎＡ２が０である場合、（ＬＡ２）ｎＡ２は単結合である。
ｎＡ２が２又は３である場合、複数のＬＡ２は互いに直列状に連結し、ＡｒＡ２は、ジナフトフラン骨格から最も離れたＬＡ２に結合する。複数のＬＡ２は同一でもよく、異なってもよい。）
Ｒ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではないＲ２０１～Ｒ２０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではなく、互いに結合しないＲ２０１～Ｒ２０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ２）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。
ただし、ＬＡ２における、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、及び置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基、並びにＡｒＡ２における、５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、及び置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基は、それぞれ下記式（Ｔ１）を満たす基である。
Ｔ１＞１．８１ｅＶ・・・（Ｔ１）
（式（Ｔ１）中、Ｔ１は、当該基の三重項エネルギーである。）］
３．陰極と、
陽極と、
前記陰極及び前記陽極の間に配置された発光層と、を有し、
前記発光層は第１の発光層及び第２の発光層を含み、
前記第１の発光層が、下記式（３）で表される化合物を含む、有機エレクトロルミネッセンス素子。
［式（３）中、
Ｒ３０１～Ｒ３０５のうち１つは、下記式（Ａ３）で表される基と結合する単結合である。
（式（Ａ３）中、
ＬＡ３は、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の複素環基である。
ＡｒＡ３は、
置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の複素環基である。
ｎＡ３は０～３の整数である。
ｎＡ３が０である場合、（ＬＡ３）ｎＡ３は単結合である。
ｎＡ３が２又は３である場合、複数のＬＡ３は互いに直列状に連結し、ＡｒＡ３は、ジナフトフラン骨格から最も離れたＬＡ３に結合する。複数のＬＡ３は同一でもよく、異なってもよい。）
Ｒ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではないＲ３０１～Ｒ３０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではなく、互いに結合しないＲ３０１～Ｒ３０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ３）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。］ According to the present invention, the following compounds and the like are provided:
1. A compound represented by the following formula (1):
[In formula (1),
One of R 101 to R 105 is a single bond bonded to a group represented by the following formula (A1).
(In formula (A1),
L A1 is,
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted biphenyldiyl group,
a substituted or unsubstituted terphenyldiyl group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted phenanthryldiyl group,
a substituted or unsubstituted benzophenanthryldiyl group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
a substituted or unsubstituted chrysenediyl group;
a substituted or unsubstituted benzochrysenediyl group,
a substituted or unsubstituted triphenylenediyl group,
a substituted or unsubstituted benzotriphenylenediyl group,
a substituted or unsubstituted fluorenediyl group;
a substituted or unsubstituted benzofluorenediyl group,
a substituted or unsubstituted dibenzofluorenediyl group,
a substituted or unsubstituted naphthofluorenediyl group,
a substituted or unsubstituted fluoranthene diyl group;
a substituted or unsubstituted benzofluoranthene diyl group;
It is a substituted or unsubstituted perylenediyl group, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted biphenyl group,
a substituted or unsubstituted terphenyl group;
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted benzophenanthryl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted chrysenyl group;
a substituted or unsubstituted benzochrysenyl group,
a substituted or unsubstituted triphenylenyl group,
a substituted or unsubstituted benzotriphenylenyl group,
a substituted or unsubstituted fluorenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
a substituted or unsubstituted naphthofluorenyl group,
a substituted or unsubstituted fluoranthenyl group;
a substituted or unsubstituted benzofluoranthenyl group;
It is a substituted or unsubstituted perylenyl group, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA1 is an integer of 0 to 3.
When nA1 is 0, (L A1 ) nA1 is a single bond.
When nA1 is 2 or 3, multiple L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the most distant from the dinaphthofuran skeleton. Multiple L A1 may be the same or different.
One or more pairs of adjacent two or more of R 106 to R 112 and R 101 to R 105 that are not a single bond bonded to the group represented by formula (A1) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R 106 to R 112 which are not bonded to each other, and R 101 to R 105 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A1) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A1).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, the two or more of R 41 to R 45 and R 49 to R 51 may be the same or different.]
2. A compound represented by the following formula (2):
[In formula (2),
One of R 201 to R 205 is a single bond bonded to a group represented by the following formula (A2).
(In formula (A2),
L A2 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A2 is
It is a substituted or unsubstituted aryl group consisting of 5 or less rings and having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA2 is an integer from 0 to 3.
When nA2 is 0, (L A2 ) nA2 is a single bond.
When nA2 is 2 or 3, multiple L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the most distant from the dinaphthofuran skeleton. Multiple L A2 may be the same or different.
Among R 206 to R 212 and R 201 to R 205 that are not single bonds bonded to the group represented by formula (A2), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 206 to R 212 which are not bonded to each other, and R 201 to R 205 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A2) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A2).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, each of the two or more R 41 to R 45 and R 49 to R 51 may be the same or different.
However, the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms which are composed of 5 or less rings in Ar A2 are each a group which satisfies the following formula (T1).
T 1 >1.81eV...(T1)
(In formula (T1), T1 is the triplet energy of the group.)
3. A cathode;
An anode;
a light-emitting layer disposed between the cathode and the anode;
the light-emitting layer includes a first light-emitting layer and a second light-emitting layer,
The organic electroluminescence device, wherein the first light-emitting layer contains a compound represented by the following formula (3):
[In formula (3),
One of R 301 to R 305 is a single bond bonded to a group represented by the following formula (A3).
(In formula (A3),
L A3 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
Ar A3 is
It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.
nA3 is an integer from 0 to 3.
When nA3 is 0, (L A3 ) nA3 is a single bond.
When nA3 is 2 or 3, multiple L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the most distant from the dinaphthofuran skeleton. Multiple L A3 may be the same or different.
Among R 306 to R 312 and R 301 to R 305 which are not single bonds bonded to the group represented by formula (A3), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 306 to R 312 which are not bonded to each other, and R 301 to R 305 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A3) each independently represent:
a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that is not the same as the group represented by formula (A3).]
１．下記式（１）で表される化合物。
Ｒ１０１～Ｒ１０５のうち１つは、下記式（Ａ１）で表される基と結合する単結合である。
ＬＡ１は、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のビフェニルジイル基、
置換もしくは無置換のターフェニルジイル基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のフェナントリルジイル基、
置換もしくは無置換のベンゾフェナントリルジイル基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のクリセンジイル基、
置換もしくは無置換のベンゾクリセンジイル基、
置換もしくは無置換のトリフェニレンジイル基、
置換もしくは無置換のベンゾトリフェニレンジイル基、
置換もしくは無置換のフルオレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、
置換もしくは無置換のジベンゾフルオレンジイル基、
置換もしくは無置換のナフトフルオレンジイル基、
置換もしくは無置換のフルオランテンジイル基、
置換もしくは無置換のベンゾフルオランテンジイル基、
置換もしくは無置換のペリレンジイル基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ１は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のビフェニル基、
置換もしくは無置換のターフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のフェナントリル基、
置換もしくは無置換のベンゾフェナントリル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のクリセニル基、
置換もしくは無置換のベンゾクリセニル基、
置換もしくは無置換のトリフェニレニル基、
置換もしくは無置換のベンゾトリフェニレニル基、
置換もしくは無置換のフルオレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトフルオレニル基、
置換もしくは無置換のフルオランテニル基、
置換もしくは無置換のベンゾフルオランテニル基、
置換もしくは無置換のペリレニル基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ１は０～３の整数である。
ｎＡ１が０である場合、（ＬＡ１）ｎＡ１は単結合である。
ｎＡ１が２又は３である場合、複数のＬＡ１は互いに直列状に連結し、ＡｒＡ１は、ジナフトフラン骨格から最も離れたＬＡ１に結合する。複数のＬＡ１は同一でもよく、異なってもよい。）
Ｒ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではないＲ１０１～Ｒ１０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではなく、互いに結合しないＲ１０１～Ｒ１０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ１）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。］
２．下記式（２）で表される化合物。
Ｒ２０１～Ｒ２０５のうち１つは、下記式（Ａ２）で表される基と結合する単結合である。
ＬＡ２は、
単結合、
置換もしくは無置換の環形成炭素数６～２１のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ２は、
５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ２は０～３の整数である。
ｎＡ２が０である場合、（ＬＡ２）ｎＡ２は単結合である。
ｎＡ２が２又は３である場合、複数のＬＡ２は互いに直列状に連結し、ＡｒＡ２は、ジナフトフラン骨格から最も離れたＬＡ２に結合する。複数のＬＡ２は同一でもよく、異なってもよい。）
Ｒ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではないＲ２０１～Ｒ２０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではなく、互いに結合しないＲ２０１～Ｒ２０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ２）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。
ただし、ＬＡ２における、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、及び置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基、並びにＡｒＡ２における、５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、及び置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基は、それぞれ下記式（Ｔ１）を満たす基である。
Ｔ１＞１．８１ｅＶ・・・（Ｔ１）
（式（Ｔ１）中、Ｔ１は、当該基の三重項エネルギーである。）］
３．陰極と、
陽極と、
前記陰極及び前記陽極の間に配置された発光層と、を有し、
前記発光層は第１の発光層及び第２の発光層を含み、
前記第１の発光層が、下記式（３）で表される化合物を含む、有機エレクトロルミネッセンス素子。
Ｒ３０１～Ｒ３０５のうち１つは、下記式（Ａ３）で表される基と結合する単結合である。
ＬＡ３は、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の複素環基である。
ＡｒＡ３は、
置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の複素環基である。
ｎＡ３は０～３の整数である。
ｎＡ３が０である場合、（ＬＡ３）ｎＡ３は単結合である。
ｎＡ３が２又は３である場合、複数のＬＡ３は互いに直列状に連結し、ＡｒＡ３は、ジナフトフラン骨格から最も離れたＬＡ３に結合する。複数のＬＡ３は同一でもよく、異なってもよい。）
Ｒ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではないＲ３０１～Ｒ３０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではなく、互いに結合しないＲ３０１～Ｒ３０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ３）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。］ According to the present invention, the following compounds and the like are provided:
1. A compound represented by the following formula (1):
One of R 101 to R 105 is a single bond bonded to a group represented by the following formula (A1).
L A1 is,
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted biphenyldiyl group,
a substituted or unsubstituted terphenyldiyl group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted phenanthryldiyl group,
a substituted or unsubstituted benzophenanthryldiyl group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
a substituted or unsubstituted chrysenediyl group;
a substituted or unsubstituted benzochrysenediyl group,
a substituted or unsubstituted triphenylenediyl group,
a substituted or unsubstituted benzotriphenylenediyl group,
a substituted or unsubstituted fluorenediyl group;
a substituted or unsubstituted benzofluorenediyl group,
a substituted or unsubstituted dibenzofluorenediyl group,
a substituted or unsubstituted naphthofluorenediyl group,
a substituted or unsubstituted fluoranthene diyl group;
a substituted or unsubstituted benzofluoranthene diyl group;
It is a substituted or unsubstituted perylenediyl group, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted biphenyl group,
a substituted or unsubstituted terphenyl group;
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted benzophenanthryl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted chrysenyl group;
a substituted or unsubstituted benzochrysenyl group,
a substituted or unsubstituted triphenylenyl group,
a substituted or unsubstituted benzotriphenylenyl group,
a substituted or unsubstituted fluorenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
a substituted or unsubstituted naphthofluorenyl group,
a substituted or unsubstituted fluoranthenyl group;
a substituted or unsubstituted benzofluoranthenyl group;
It is a substituted or unsubstituted perylenyl group, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA1 is an integer of 0 to 3.
When nA1 is 0, (L A1 ) nA1 is a single bond.
When nA1 is 2 or 3, multiple L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the most distant from the dinaphthofuran skeleton. Multiple L A1 may be the same or different.
One or more pairs of adjacent two or more of R 106 to R 112 and R 101 to R 105 that are not a single bond bonded to the group represented by formula (A1) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R 106 to R 112 which are not bonded to each other, and R 101 to R 105 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A1) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A1).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, the two or more of R 41 to R 45 and R 49 to R 51 may be the same or different.]
2. A compound represented by the following formula (2):
One of R 201 to R 205 is a single bond bonded to a group represented by the following formula (A2).
L A2 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A2 is
It is a substituted or unsubstituted aryl group consisting of 5 or less rings and having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA2 is an integer from 0 to 3.
When nA2 is 0, (L A2 ) nA2 is a single bond.
When nA2 is 2 or 3, multiple L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the most distant from the dinaphthofuran skeleton. Multiple L A2 may be the same or different.
Among R 206 to R 212 and R 201 to R 205 that are not single bonds bonded to the group represented by formula (A2), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 206 to R 212 which are not bonded to each other, and R 201 to R 205 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A2) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A2).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, each of the two or more R 41 to R 45 and R 49 to R 51 may be the same or different.
However, the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms which are composed of 5 or less rings in Ar A2 are each a group which satisfies the following formula (T1).
T 1 >1.81eV...(T1)
(In formula (T1), T1 is the triplet energy of the group.)
3. A cathode;
An anode;
a light-emitting layer disposed between the cathode and the anode;
the light-emitting layer includes a first light-emitting layer and a second light-emitting layer,
The organic electroluminescence device, wherein the first light-emitting layer contains a compound represented by the following formula (3):
One of R 301 to R 305 is a single bond bonded to a group represented by the following formula (A3).
L A3 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
Ar A3 is
It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.
nA3 is an integer from 0 to 3.
When nA3 is 0, (L A3 ) nA3 is a single bond.
When nA3 is 2 or 3, multiple L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the most distant from the dinaphthofuran skeleton. Multiple L A3 may be the same or different.
Among R 306 to R 312 and R 301 to R 305 which are not single bonds bonded to the group represented by formula (A3), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 306 to R 312 which are not bonded to each other, and R 301 to R 305 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A3) each independently represent:
a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that is not the same as the group represented by formula (A3).]
本発明によれば、高性能な有機ＥＬ素子及び当該有機ＥＬ素子を実現可能な化合物が提供できる。
The present invention provides a high-performance organic EL element and a compound capable of realizing the organic EL element.
［定義］
本明細書において、水素原子とは、中性子数が異なる同位体、即ち、軽水素（protium）、重水素（deuterium）、及び三重水素（tritium）を包含する。 [Definition]
In this specification, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.
本明細書において、水素原子とは、中性子数が異なる同位体、即ち、軽水素（protium）、重水素（deuterium）、及び三重水素（tritium）を包含する。 [Definition]
In this specification, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.
本明細書において、化学構造式中、「Ｒ」等の記号や重水素原子を表す「Ｄ」が明示されていない結合可能位置には、水素原子、即ち、軽水素原子、重水素原子、又は三重水素原子が結合しているものとする。
In this specification, in chemical structural formulas, any possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom is assumed to have a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, bonded to it.
本明細書において、環形成炭素数とは、原子が環状に結合した構造の化合物（例えば、単環化合物、縮合環化合物、架橋化合物、炭素環化合物、及び複素環化合物）の当該環自体を構成する原子のうちの炭素原子の数を表す。当該環が置換基によって置換される場合、置換基に含まれる炭素は環形成炭素数には含まない。以下で記される「環形成炭素数」については、別途記載のない限り同様とする。例えば、ベンゼン環は環形成炭素数が６であり、ナフタレン環は環形成炭素数が１０であり、ピリジン環は環形成炭素数５であり、フラン環は環形成炭素数４である。また、例えば、９，９－ジフェニルフルオレニル基の環形成炭素数は１３であり、９，９’－スピロビフルオレニル基の環形成炭素数は２５である。
また、ベンゼン環に置換基として、例えば、アルキル基が置換している場合、当該アルキル基の炭素数は、ベンゼン環の環形成炭素数に含めない。そのため、アルキル基が置換しているベンゼン環の環形成炭素数は、６である。また、ナフタレン環に置換基として、例えば、アルキル基が置換している場合、当該アルキル基の炭素数は、ナフタレン環の環形成炭素数に含めない。そのため、アルキル基が置換しているナフタレン環の環形成炭素数は、１０である。 In this specification, the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.
In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
また、ベンゼン環に置換基として、例えば、アルキル基が置換している場合、当該アルキル基の炭素数は、ベンゼン環の環形成炭素数に含めない。そのため、アルキル基が置換しているベンゼン環の環形成炭素数は、６である。また、ナフタレン環に置換基として、例えば、アルキル基が置換している場合、当該アルキル基の炭素数は、ナフタレン環の環形成炭素数に含めない。そのため、アルキル基が置換しているナフタレン環の環形成炭素数は、１０である。 In this specification, the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.
In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
本明細書において、環形成原子数とは、原子が環状に結合した構造（例えば、単環、縮合環、及び環集合）の化合物（例えば、単環化合物、縮合環化合物、架橋化合物、炭素環化合物、及び複素環化合物）の当該環自体を構成する原子の数を表す。環を構成しない原子（例えば、環を構成する原子の結合を終端する水素原子）や、当該環が置換基によって置換される場合の置換基に含まれる原子は環形成原子数には含まない。以下で記される「環形成原子数」については、別途記載のない限り同様とする。例えば、ピリジン環の環形成原子数は６であり、キナゾリン環の環形成原子数は１０であり、フラン環の環形成原子数は５である。例えば、ピリジン環に結合している水素原子、又は置換基を構成する原子の数は、ピリジン環形成原子数の数に含めない。そのため、水素原子、又は置換基が結合しているピリジン環の環形成原子数は、６である。また、例えば、キナゾリン環の炭素原子に結合している水素原子、又は置換基を構成する原子については、キナゾリン環の環形成原子数の数に含めない。そのため、水素原子、又は置換基が結合しているキナゾリン環の環形成原子数は１０である。
In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) with a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). The number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. For example, hydrogen atoms bonded to carbon atoms in a quinazoline ring or atoms constituting a substituent are not included in the number of ring atoms in the quinazoline ring. Therefore, the number of ring atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
本明細書において、「置換もしくは無置換の炭素数ＸＸ～ＹＹのＺＺ基」という表現における「炭素数ＸＸ～ＹＹ」は、ＺＺ基が無置換である場合の炭素数を表し、置換されている場合の置換基の炭素数を含めない。ここで、「ＹＹ」は、「ＸＸ」よりも大きく、「ＸＸ」は、１以上の整数を意味し、「ＹＹ」は、２以上の整数を意味する。
In this specification, the "carbon number XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon numbers XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
本明細書において、「置換もしくは無置換の原子数ＸＸ～ＹＹのＺＺ基」という表現における「原子数ＸＸ～ＹＹ」は、ＺＺ基が無置換である場合の原子数を表し、置換されている場合の置換基の原子数を含めない。ここで、「ＹＹ」は、「ＸＸ」よりも大きく、「ＸＸ」は、１以上の整数を意味し、「ＹＹ」は、２以上の整数を意味する。
In this specification, the "atomic number XX to YY" in the expression "substituted or unsubstituted ZZ group having atomic number XX to YY" refers to the atomic number when the ZZ group is unsubstituted, and does not include the atomic number of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
本明細書において、無置換のＺＺ基とは「置換もしくは無置換のＺＺ基」が「無置換のＺＺ基」である場合を表し、置換のＺＺ基とは「置換もしくは無置換のＺＺ基」が「置換のＺＺ基」である場合を表す。
本明細書において、「置換もしくは無置換のＺＺ基」という場合における「無置換」とは、ＺＺ基における水素原子が置換基と置き換わっていないことを意味する。「無置換のＺＺ基」における水素原子は、軽水素原子、重水素原子、又は三重水素原子である。
また、本明細書において、「置換もしくは無置換のＺＺ基」という場合における「置換」とは、ＺＺ基における１つ以上の水素原子が、置換基と置き換わっていることを意味する。「ＡＡ基で置換されたＢＢ基」という場合における「置換」も同様に、ＢＢ基における１つ以上の水素原子が、ＡＡ基と置き換わっていることを意味する。 In this specification, the term "unsubstituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and the term "substituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".
In the present specification, "unsubstituted" in the case of "a substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
In the present specification, "substitution" in the case of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substitution" in the case of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.
本明細書において、「置換もしくは無置換のＺＺ基」という場合における「無置換」とは、ＺＺ基における水素原子が置換基と置き換わっていないことを意味する。「無置換のＺＺ基」における水素原子は、軽水素原子、重水素原子、又は三重水素原子である。
また、本明細書において、「置換もしくは無置換のＺＺ基」という場合における「置換」とは、ＺＺ基における１つ以上の水素原子が、置換基と置き換わっていることを意味する。「ＡＡ基で置換されたＢＢ基」という場合における「置換」も同様に、ＢＢ基における１つ以上の水素原子が、ＡＡ基と置き換わっていることを意味する。 In this specification, the term "unsubstituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and the term "substituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".
In the present specification, "unsubstituted" in the case of "a substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
In the present specification, "substitution" in the case of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substitution" in the case of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.
「本明細書に記載の置換基」
以下、本明細書に記載の置換基について説明する。 "Substituents Described Herein"
The substituents described in this specification will be described below.
以下、本明細書に記載の置換基について説明する。 "Substituents Described Herein"
The substituents described in this specification will be described below.
本明細書に記載の「無置換のアリール基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
本明細書に記載の「無置換の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
本明細書に記載の「無置換のアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。
本明細書に記載の「無置換のアルケニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
本明細書に記載の「無置換のアルキニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
本明細書に記載の「無置換のシクロアルキル基」の環形成炭素数は、本明細書に別途記載のない限り、３～５０であり、好ましくは３～２０、より好ましくは３～６である。
本明細書に記載の「無置換のアリーレン基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
本明細書に記載の「無置換の２価の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
本明細書に記載の「無置換のアルキレン基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。 The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
The number of carbon atoms in the "unsubstituted alkenyl group" described in this specification is, unless otherwise specified in this specification, 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
The number of carbon atoms in the "unsubstituted alkynyl group" described in this specification, unless otherwise specified in this specification, is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification.
The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
The number of ring atoms in the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
本明細書に記載の「無置換の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
本明細書に記載の「無置換のアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。
本明細書に記載の「無置換のアルケニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
本明細書に記載の「無置換のアルキニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
本明細書に記載の「無置換のシクロアルキル基」の環形成炭素数は、本明細書に別途記載のない限り、３～５０であり、好ましくは３～２０、より好ましくは３～６である。
本明細書に記載の「無置換のアリーレン基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
本明細書に記載の「無置換の２価の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
本明細書に記載の「無置換のアルキレン基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。 The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
The number of carbon atoms in the "unsubstituted alkenyl group" described in this specification is, unless otherwise specified in this specification, 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
The number of carbon atoms in the "unsubstituted alkynyl group" described in this specification, unless otherwise specified in this specification, is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification.
The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
The number of ring atoms in the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
・「置換もしくは無置換のアリール基」
本明細書に記載の「置換もしくは無置換のアリール基」の具体例（具体例群Ｇ１）としては、以下の無置換のアリール基（具体例群Ｇ１Ａ）及び置換のアリール基（具体例群Ｇ１Ｂ）等が挙げられる。（ここで、無置換のアリール基とは「置換もしくは無置換のアリール基」が「無置換のアリール基」である場合を指し、置換のアリール基とは「置換もしくは無置換のアリール基」が「置換のアリール基」である場合を指す。）本明細書において、単に「アリール基」という場合は、「無置換のアリール基」と「置換のアリール基」の両方を含む。
「置換のアリール基」は、「無置換のアリール基」の１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアリール基」としては、例えば、下記具体例群Ｇ１Ａの「無置換のアリール基」の１つ以上の水素原子が置換基と置き換わった基、及び下記具体例群Ｇ１Ｂの置換のアリール基の例等が挙げられる。尚、ここに列挙した「無置換のアリール基」の例、及び「置換のアリール基」の例は、一例に過ぎず、本明細書に記載の「置換のアリール基」には、下記具体例群Ｇ１Ｂの「置換のアリール基」におけるアリール基自体の炭素原子に結合する水素原子がさらに置換基と置き換わった基、及び下記具体例群Ｇ１Ｂの「置換のアリール基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted aryl group"
Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the term "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group".
The term "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include the "unsubstituted aryl group" in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.
本明細書に記載の「置換もしくは無置換のアリール基」の具体例（具体例群Ｇ１）としては、以下の無置換のアリール基（具体例群Ｇ１Ａ）及び置換のアリール基（具体例群Ｇ１Ｂ）等が挙げられる。（ここで、無置換のアリール基とは「置換もしくは無置換のアリール基」が「無置換のアリール基」である場合を指し、置換のアリール基とは「置換もしくは無置換のアリール基」が「置換のアリール基」である場合を指す。）本明細書において、単に「アリール基」という場合は、「無置換のアリール基」と「置換のアリール基」の両方を含む。
「置換のアリール基」は、「無置換のアリール基」の１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアリール基」としては、例えば、下記具体例群Ｇ１Ａの「無置換のアリール基」の１つ以上の水素原子が置換基と置き換わった基、及び下記具体例群Ｇ１Ｂの置換のアリール基の例等が挙げられる。尚、ここに列挙した「無置換のアリール基」の例、及び「置換のアリール基」の例は、一例に過ぎず、本明細書に記載の「置換のアリール基」には、下記具体例群Ｇ１Ｂの「置換のアリール基」におけるアリール基自体の炭素原子に結合する水素原子がさらに置換基と置き換わった基、及び下記具体例群Ｇ１Ｂの「置換のアリール基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted aryl group"
Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the term "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group".
The term "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include the "unsubstituted aryl group" in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.
・無置換のアリール基（具体例群Ｇ１Ａ）：
フェニル基、
ｐ－ビフェニル基、
ｍ－ビフェニル基、
ｏ－ビフェニル基、
ｐ－ターフェニル－４－イル基、
ｐ－ターフェニル－３－イル基、
ｐ－ターフェニル－２－イル基、
ｍ－ターフェニル－４－イル基、
ｍ－ターフェニル－３－イル基、
ｍ－ターフェニル－２－イル基、
ｏ－ターフェニル－４－イル基、
ｏ－ターフェニル－３－イル基、
ｏ－ターフェニル－２－イル基、
１－ナフチル基、
２－ナフチル基、
アントリル基、
ベンゾアントリル基、
フェナントリル基、
ベンゾフェナントリル基、
フェナレニル基、
ピレニル基、
クリセニル基、
ベンゾクリセニル基、
トリフェニレニル基、
ベンゾトリフェニレニル基、
テトラセニル基、
ペンタセニル基、
フルオレニル基、
９，９’－スピロビフルオレニル基、
ベンゾフルオレニル基、
ジベンゾフルオレニル基、
フルオランテニル基、
ベンゾフルオランテニル基、
ペリレニル基、及び
下記一般式（ＴＥＭＰ－１）～（ＴＥＭＰ－１５）で表される環構造から１つの水素原子を除くことにより誘導される１価のアリール基。 Unsubstituted aryl groups (specific example group G1A):
Phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
p-terphenyl-4-yl group,
p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
anthryl group,
Benzanthryl group,
A phenanthryl group,
Benzophenanthryl group,
A phenalenyl group,
Pyrenyl group,
Chrysenyl group,
benzochrysenyl group,
A triphenylenyl group,
Benzotriphenylenyl group,
tetracenyl group,
Pentacenyl group,
fluorenyl group,
9,9'-spirobifluorenyl group,
Benzofluorenyl group,
Dibenzofluorenyl group,
fluoranthenyl group,
Benzofluoranthenyl group,
A perylenyl group, or a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).
フェニル基、
ｐ－ビフェニル基、
ｍ－ビフェニル基、
ｏ－ビフェニル基、
ｐ－ターフェニル－４－イル基、
ｐ－ターフェニル－３－イル基、
ｐ－ターフェニル－２－イル基、
ｍ－ターフェニル－４－イル基、
ｍ－ターフェニル－３－イル基、
ｍ－ターフェニル－２－イル基、
ｏ－ターフェニル－４－イル基、
ｏ－ターフェニル－３－イル基、
ｏ－ターフェニル－２－イル基、
１－ナフチル基、
２－ナフチル基、
アントリル基、
ベンゾアントリル基、
フェナントリル基、
ベンゾフェナントリル基、
フェナレニル基、
ピレニル基、
クリセニル基、
ベンゾクリセニル基、
トリフェニレニル基、
ベンゾトリフェニレニル基、
テトラセニル基、
ペンタセニル基、
フルオレニル基、
９，９’－スピロビフルオレニル基、
ベンゾフルオレニル基、
ジベンゾフルオレニル基、
フルオランテニル基、
ベンゾフルオランテニル基、
ペリレニル基、及び
下記一般式（ＴＥＭＰ－１）～（ＴＥＭＰ－１５）で表される環構造から１つの水素原子を除くことにより誘導される１価のアリール基。 Unsubstituted aryl groups (specific example group G1A):
Phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
p-terphenyl-4-yl group,
p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
anthryl group,
Benzanthryl group,
A phenanthryl group,
Benzophenanthryl group,
A phenalenyl group,
Pyrenyl group,
Chrysenyl group,
benzochrysenyl group,
A triphenylenyl group,
Benzotriphenylenyl group,
tetracenyl group,
Pentacenyl group,
fluorenyl group,
9,9'-spirobifluorenyl group,
Benzofluorenyl group,
Dibenzofluorenyl group,
fluoranthenyl group,
Benzofluoranthenyl group,
A perylenyl group, or a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).
・置換のアリール基（具体例群Ｇ１Ｂ）：
ｏ－トリル基、
ｍ－トリル基、
ｐ－トリル基、
パラ－キシリル基、
メタ－キシリル基、
オルト－キシリル基、
パラ－イソプロピルフェニル基、
メタ－イソプロピルフェニル基、
オルト－イソプロピルフェニル基、
パラ－ｔ－ブチルフェニル基、
メタ－ｔ－ブチルフェニル基、
オルト－ｔ－ブチルフェニル基、
３，４，５－トリメチルフェニル基、
９，９－ジメチルフルオレニル基、
９，９－ジフェニルフルオレニル基
９，９－ビス（４－メチルフェニル）フルオレニル基、
９，９－ビス（４－イソプロピルフェニル）フルオレニル基、
９，９－ビス（４－ｔ－ブチルフェニル）フルオレニル基、
シアノフェニル基、
トリフェニルシリルフェニル基、
トリメチルシリルフェニル基、
フェニルナフチル基、
ナフチルフェニル基、及び
前記一般式（ＴＥＭＰ－１）～（ＴＥＭＰ－１５）で表される環構造から誘導される１価の基の１つ以上の水素原子が置換基と置き換わった基。 Substituted aryl groups (specific example group G1B):
o-tolyl group,
m-tolyl group,
p-tolyl group,
para-xylyl group,
meta-xylyl group,
ortho-xylyl group,
para-isopropylphenyl group,
meta-isopropylphenyl group,
ortho-isopropylphenyl group,
para-t-butylphenyl group,
A meta-t-butylphenyl group,
ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group,
9,9-bis(4-isopropylphenyl)fluorenyl group,
9,9-bis(4-t-butylphenyl)fluorenyl group,
Cyanophenyl group,
triphenylsilylphenyl group,
trimethylsilylphenyl group,
phenylnaphthyl group,
naphthylphenyl group, and monovalent groups derived from the ring structures represented by the above general formulae (TEMP-1) to (TEMP-15) in which one or more hydrogen atoms are replaced with substituents.
ｏ－トリル基、
ｍ－トリル基、
ｐ－トリル基、
パラ－キシリル基、
メタ－キシリル基、
オルト－キシリル基、
パラ－イソプロピルフェニル基、
メタ－イソプロピルフェニル基、
オルト－イソプロピルフェニル基、
パラ－ｔ－ブチルフェニル基、
メタ－ｔ－ブチルフェニル基、
オルト－ｔ－ブチルフェニル基、
３，４，５－トリメチルフェニル基、
９，９－ジメチルフルオレニル基、
９，９－ジフェニルフルオレニル基
９，９－ビス（４－メチルフェニル）フルオレニル基、
９，９－ビス（４－イソプロピルフェニル）フルオレニル基、
９，９－ビス（４－ｔ－ブチルフェニル）フルオレニル基、
シアノフェニル基、
トリフェニルシリルフェニル基、
トリメチルシリルフェニル基、
フェニルナフチル基、
ナフチルフェニル基、及び
前記一般式（ＴＥＭＰ－１）～（ＴＥＭＰ－１５）で表される環構造から誘導される１価の基の１つ以上の水素原子が置換基と置き換わった基。 Substituted aryl groups (specific example group G1B):
o-tolyl group,
m-tolyl group,
p-tolyl group,
para-xylyl group,
meta-xylyl group,
ortho-xylyl group,
para-isopropylphenyl group,
meta-isopropylphenyl group,
ortho-isopropylphenyl group,
para-t-butylphenyl group,
A meta-t-butylphenyl group,
ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group,
9,9-bis(4-isopropylphenyl)fluorenyl group,
9,9-bis(4-t-butylphenyl)fluorenyl group,
Cyanophenyl group,
triphenylsilylphenyl group,
trimethylsilylphenyl group,
phenylnaphthyl group,
naphthylphenyl group, and monovalent groups derived from the ring structures represented by the above general formulae (TEMP-1) to (TEMP-15) in which one or more hydrogen atoms are replaced with substituents.
・「置換もしくは無置換の複素環基」
本明細書に記載の「複素環基」は、環形成原子にヘテロ原子を少なくとも１つ含む環状の基である。ヘテロ原子の具体例としては、窒素原子、酸素原子、硫黄原子、ケイ素原子、リン原子、及びホウ素原子が挙げられる。
本明細書に記載の「複素環基」は、単環の基であるか、又は縮合環の基である。
本明細書に記載の「複素環基」は、芳香族複素環基であるか、又は非芳香族複素環基である。
本明細書に記載の「置換もしくは無置換の複素環基」の具体例（具体例群Ｇ２）としては、以下の無置換の複素環基（具体例群Ｇ２Ａ）、及び置換の複素環基（具体例群Ｇ２Ｂ）等が挙げられる。（ここで、無置換の複素環基とは「置換もしくは無置換の複素環基」が「無置換の複素環基」である場合を指し、置換の複素環基とは「置換もしくは無置換の複素環基」が「置換の複素環基」である場合を指す。）本明細書において、単に「複素環基」という場合は、「無置換の複素環基」と「置換の複素環基」の両方を含む。
「置換の複素環基」は、「無置換の複素環基」の１つ以上の水素原子が置換基と置き換わった基を意味する。「置換の複素環基」の具体例は、下記具体例群Ｇ２Ａの「無置換の複素環基」の水素原子が置き換わった基、及び下記具体例群Ｇ２Ｂの置換の複素環基の例等が挙げられる。尚、ここに列挙した「無置換の複素環基」の例や「置換の複素環基」の例は、一例に過ぎず、本明細書に記載の「置換の複素環基」には、具体例群Ｇ２Ｂの「置換の複素環基」における複素環基自体の環形成原子に結合する水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ２Ｂの「置換の複素環基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted heterocyclic group"
The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
The "heterocyclic groups" described herein are either monocyclic or fused ring groups.
The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group.
Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when the term "heterocyclic group" is simply used, it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group".
The term "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified. The examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes the groups in the "substituted heterocyclic group" in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the groups in the "substituted heterocyclic group" in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.
本明細書に記載の「複素環基」は、環形成原子にヘテロ原子を少なくとも１つ含む環状の基である。ヘテロ原子の具体例としては、窒素原子、酸素原子、硫黄原子、ケイ素原子、リン原子、及びホウ素原子が挙げられる。
本明細書に記載の「複素環基」は、単環の基であるか、又は縮合環の基である。
本明細書に記載の「複素環基」は、芳香族複素環基であるか、又は非芳香族複素環基である。
本明細書に記載の「置換もしくは無置換の複素環基」の具体例（具体例群Ｇ２）としては、以下の無置換の複素環基（具体例群Ｇ２Ａ）、及び置換の複素環基（具体例群Ｇ２Ｂ）等が挙げられる。（ここで、無置換の複素環基とは「置換もしくは無置換の複素環基」が「無置換の複素環基」である場合を指し、置換の複素環基とは「置換もしくは無置換の複素環基」が「置換の複素環基」である場合を指す。）本明細書において、単に「複素環基」という場合は、「無置換の複素環基」と「置換の複素環基」の両方を含む。
「置換の複素環基」は、「無置換の複素環基」の１つ以上の水素原子が置換基と置き換わった基を意味する。「置換の複素環基」の具体例は、下記具体例群Ｇ２Ａの「無置換の複素環基」の水素原子が置き換わった基、及び下記具体例群Ｇ２Ｂの置換の複素環基の例等が挙げられる。尚、ここに列挙した「無置換の複素環基」の例や「置換の複素環基」の例は、一例に過ぎず、本明細書に記載の「置換の複素環基」には、具体例群Ｇ２Ｂの「置換の複素環基」における複素環基自体の環形成原子に結合する水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ２Ｂの「置換の複素環基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted heterocyclic group"
The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
The "heterocyclic groups" described herein are either monocyclic or fused ring groups.
The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group.
Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when the term "heterocyclic group" is simply used, it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group".
The term "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified. The examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes the groups in the "substituted heterocyclic group" in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the groups in the "substituted heterocyclic group" in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.
具体例群Ｇ２Ａは、例えば、以下の窒素原子を含む無置換の複素環基（具体例群Ｇ２Ａ１）、酸素原子を含む無置換の複素環基（具体例群Ｇ２Ａ２）、硫黄原子を含む無置換の複素環基（具体例群Ｇ２Ａ３）、及び下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から１つの水素原子を除くことにより誘導される１価の複素環基（具体例群Ｇ２Ａ４）を含む。
Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
具体例群Ｇ２Ｂは、例えば、以下の窒素原子を含む置換の複素環基（具体例群Ｇ２Ｂ１）、酸素原子を含む置換の複素環基（具体例群Ｇ２Ｂ２）、硫黄原子を含む置換の複素環基（具体例群Ｇ２Ｂ３）、及び下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基の１つ以上の水素原子が置換基と置き換わった基（具体例群Ｇ２Ｂ４）を含む。
Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
・窒素原子を含む無置換の複素環基（具体例群Ｇ２Ａ１）：
ピロリル基、
イミダゾリル基、
ピラゾリル基、
トリアゾリル基、
テトラゾリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ピリジル基、
ピリダジニル基、
ピリミジニル基、
ピラジニル基、
トリアジニル基、
インドリル基、
イソインドリル基、
インドリジニル基、
キノリジニル基、
キノリル基、
イソキノリル基、
シンノリル基、
フタラジニル基、
キナゾリニル基、
キノキサリニル基、
ベンゾイミダゾリル基、
インダゾリル基、
フェナントロリニル基、
フェナントリジニル基、
アクリジニル基、
フェナジニル基、
カルバゾリル基、
ベンゾカルバゾリル基、
モルホリノ基、
フェノキサジニル基、
フェノチアジニル基、
アザカルバゾリル基、及びジアザカルバゾリル基。 Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1):
Pyrrolyl group,
imidazolyl group,
A pyrazolyl group,
A triazolyl group,
Tetrazolyl group,
oxazolyl group,
an isoxazolyl group,
oxadiazolyl group,
A thiazolyl group,
isothiazolyl group,
A thiadiazolyl group,
Pyridyl group,
pyridazinyl group,
A pyrimidinyl group,
Pyrazinyl group,
Triazinyl group,
Indolyl groups,
isoindolyl group,
Indolizinyl group,
A quinolizinyl group,
A quinolyl group,
isoquinolyl group,
Cinnolyl group,
phthalazinyl group,
A quinazolinyl group,
quinoxalinyl group,
Benzimidazolyl group,
Indazolyl group,
A phenanthrolinyl group,
A phenanthridinyl group,
acridinyl group,
A phenazinyl group,
A carbazolyl group,
Benzocarbazolyl group,
morpholino group,
phenoxazinyl group,
A phenothiazinyl group,
Azacarbazolyl and diazacarbazolyl groups.
ピロリル基、
イミダゾリル基、
ピラゾリル基、
トリアゾリル基、
テトラゾリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ピリジル基、
ピリダジニル基、
ピリミジニル基、
ピラジニル基、
トリアジニル基、
インドリル基、
イソインドリル基、
インドリジニル基、
キノリジニル基、
キノリル基、
イソキノリル基、
シンノリル基、
フタラジニル基、
キナゾリニル基、
キノキサリニル基、
ベンゾイミダゾリル基、
インダゾリル基、
フェナントロリニル基、
フェナントリジニル基、
アクリジニル基、
フェナジニル基、
カルバゾリル基、
ベンゾカルバゾリル基、
モルホリノ基、
フェノキサジニル基、
フェノチアジニル基、
アザカルバゾリル基、及びジアザカルバゾリル基。 Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1):
Pyrrolyl group,
imidazolyl group,
A pyrazolyl group,
A triazolyl group,
Tetrazolyl group,
oxazolyl group,
an isoxazolyl group,
oxadiazolyl group,
A thiazolyl group,
isothiazolyl group,
A thiadiazolyl group,
Pyridyl group,
pyridazinyl group,
A pyrimidinyl group,
Pyrazinyl group,
Triazinyl group,
Indolyl groups,
isoindolyl group,
Indolizinyl group,
A quinolizinyl group,
A quinolyl group,
isoquinolyl group,
Cinnolyl group,
phthalazinyl group,
A quinazolinyl group,
quinoxalinyl group,
Benzimidazolyl group,
Indazolyl group,
A phenanthrolinyl group,
A phenanthridinyl group,
acridinyl group,
A phenazinyl group,
A carbazolyl group,
Benzocarbazolyl group,
morpholino group,
phenoxazinyl group,
A phenothiazinyl group,
Azacarbazolyl and diazacarbazolyl groups.
・酸素原子を含む無置換の複素環基（具体例群Ｇ２Ａ２）：
フリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
キサンテニル基、
ベンゾフラニル基、
イソベンゾフラニル基、
ジベンゾフラニル基、
ナフトベンゾフラニル基、
ベンゾオキサゾリル基、
ベンゾイソキサゾリル基、
フェノキサジニル基、
モルホリノ基、
ジナフトフラニル基、
アザジベンゾフラニル基、
ジアザジベンゾフラニル基、
アザナフトベンゾフラニル基、及び
ジアザナフトベンゾフラニル基。 Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2):
Furyl group,
oxazolyl group,
an isoxazolyl group,
oxadiazolyl group,
xanthenyl group,
benzofuranyl group,
isobenzofuranyl group,
Dibenzofuranyl group,
naphthobenzofuranyl group,
benzoxazolyl group,
benzoisoxazolyl group,
phenoxazinyl group,
morpholino group,
Dinaphthofuranyl group,
azadibenzofuranyl group,
diazadibenzofuranyl group,
Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
フリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
キサンテニル基、
ベンゾフラニル基、
イソベンゾフラニル基、
ジベンゾフラニル基、
ナフトベンゾフラニル基、
ベンゾオキサゾリル基、
ベンゾイソキサゾリル基、
フェノキサジニル基、
モルホリノ基、
ジナフトフラニル基、
アザジベンゾフラニル基、
ジアザジベンゾフラニル基、
アザナフトベンゾフラニル基、及び
ジアザナフトベンゾフラニル基。 Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2):
Furyl group,
oxazolyl group,
an isoxazolyl group,
oxadiazolyl group,
xanthenyl group,
benzofuranyl group,
isobenzofuranyl group,
Dibenzofuranyl group,
naphthobenzofuranyl group,
benzoxazolyl group,
benzoisoxazolyl group,
phenoxazinyl group,
morpholino group,
Dinaphthofuranyl group,
azadibenzofuranyl group,
diazadibenzofuranyl group,
Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
・硫黄原子を含む無置換の複素環基（具体例群Ｇ２Ａ３）：
チエニル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ベンゾチオフェニル基（ベンゾチエニル基）、
イソベンゾチオフェニル基（イソベンゾチエニル基）、
ジベンゾチオフェニル基（ジベンゾチエニル基）、
ナフトベンゾチオフェニル基（ナフトベンゾチエニル基）、
ベンゾチアゾリル基、
ベンゾイソチアゾリル基、
フェノチアジニル基、
ジナフトチオフェニル基（ジナフトチエニル基）、
アザジベンゾチオフェニル基（アザジベンゾチエニル基）、
ジアザジベンゾチオフェニル基（ジアザジベンゾチエニル基）、
アザナフトベンゾチオフェニル基（アザナフトベンゾチエニル基）、及び
ジアザナフトベンゾチオフェニル基（ジアザナフトベンゾチエニル基）。 Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3):
A thienyl group,
A thiazolyl group,
isothiazolyl group,
A thiadiazolyl group,
Benzothiophenyl group (benzothienyl group),
isobenzothiophenyl group (isobenzothienyl group),
Dibenzothiophenyl group (dibenzothienyl group),
Naphthobenzothiophenyl group (naphthobenzothienyl group),
benzothiazolyl group,
Benzisothiazolyl group,
A phenothiazinyl group,
Dinaphthothiophenyl group (dinaphthothienyl group),
Azadibenzothiophenyl group (azadibenzothienyl group),
Diazadibenzothiophenyl group (diazadibenzothienyl group),
Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
チエニル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ベンゾチオフェニル基（ベンゾチエニル基）、
イソベンゾチオフェニル基（イソベンゾチエニル基）、
ジベンゾチオフェニル基（ジベンゾチエニル基）、
ナフトベンゾチオフェニル基（ナフトベンゾチエニル基）、
ベンゾチアゾリル基、
ベンゾイソチアゾリル基、
フェノチアジニル基、
ジナフトチオフェニル基（ジナフトチエニル基）、
アザジベンゾチオフェニル基（アザジベンゾチエニル基）、
ジアザジベンゾチオフェニル基（ジアザジベンゾチエニル基）、
アザナフトベンゾチオフェニル基（アザナフトベンゾチエニル基）、及び
ジアザナフトベンゾチオフェニル基（ジアザナフトベンゾチエニル基）。 Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3):
A thienyl group,
A thiazolyl group,
isothiazolyl group,
A thiadiazolyl group,
Benzothiophenyl group (benzothienyl group),
isobenzothiophenyl group (isobenzothienyl group),
Dibenzothiophenyl group (dibenzothienyl group),
Naphthobenzothiophenyl group (naphthobenzothienyl group),
benzothiazolyl group,
Benzisothiazolyl group,
A phenothiazinyl group,
Dinaphthothiophenyl group (dinaphthothienyl group),
Azadibenzothiophenyl group (azadibenzothienyl group),
Diazadibenzothiophenyl group (diazadibenzothienyl group),
Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
・下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から１つの水素原子を除くことにより誘導される１価の複素環基（具体例群Ｇ２Ａ４）：
- Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):
前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）において、ＸＡ及びＹＡは、それぞれ独立に、酸素原子、硫黄原子、ＮＨ、又はＣＨ２である。ただし、ＸＡ及びＹＡのうち少なくとも１つは、酸素原子、硫黄原子、又はＮＨである。
前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）において、ＸＡ及びＹＡの少なくともいずれかがＮＨ、又はＣＨ２である場合、前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基には、これらＮＨ、又はＣＨ２から１つの水素原子を除いて得られる１価の基が含まれる。 In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2 , provided that at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
In the general formulae (TEMP-16) to (TEMP-33), when at least one of XA and YA is NH or CH2 , the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from the NH or CH2 .
前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）において、ＸＡ及びＹＡの少なくともいずれかがＮＨ、又はＣＨ２である場合、前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基には、これらＮＨ、又はＣＨ２から１つの水素原子を除いて得られる１価の基が含まれる。 In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2 , provided that at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
In the general formulae (TEMP-16) to (TEMP-33), when at least one of XA and YA is NH or CH2 , the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from the NH or CH2 .
・窒素原子を含む置換の複素環基（具体例群Ｇ２Ｂ１）：
（９－フェニル）カルバゾリル基、
（９－ビフェニリル）カルバゾリル基、
（９－フェニル）フェニルカルバゾリル基、
（９－ナフチル）カルバゾリル基、
ジフェニルカルバゾール－９－イル基、
フェニルカルバゾール－９－イル基、
メチルベンゾイミダゾリル基、
エチルベンゾイミダゾリル基、
フェニルトリアジニル基、
ビフェニリルトリアジニル基、
ジフェニルトリアジニル基、
フェニルキナゾリニル基、及び
ビフェニリルキナゾリニル基。 Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1):
A (9-phenyl)carbazolyl group,
A (9-biphenylyl)carbazolyl group,
(9-phenyl)phenylcarbazolyl group,
(9-naphthyl)carbazolyl group,
diphenylcarbazol-9-yl group,
A phenylcarbazol-9-yl group,
methylbenzimidazolyl group,
Ethyl benzimidazolyl group,
phenyltriazinyl group,
Biphenylyltriazinyl group,
Diphenyltriazinyl group,
a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
（９－フェニル）カルバゾリル基、
（９－ビフェニリル）カルバゾリル基、
（９－フェニル）フェニルカルバゾリル基、
（９－ナフチル）カルバゾリル基、
ジフェニルカルバゾール－９－イル基、
フェニルカルバゾール－９－イル基、
メチルベンゾイミダゾリル基、
エチルベンゾイミダゾリル基、
フェニルトリアジニル基、
ビフェニリルトリアジニル基、
ジフェニルトリアジニル基、
フェニルキナゾリニル基、及び
ビフェニリルキナゾリニル基。 Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1):
A (9-phenyl)carbazolyl group,
A (9-biphenylyl)carbazolyl group,
(9-phenyl)phenylcarbazolyl group,
(9-naphthyl)carbazolyl group,
diphenylcarbazol-9-yl group,
A phenylcarbazol-9-yl group,
methylbenzimidazolyl group,
Ethyl benzimidazolyl group,
phenyltriazinyl group,
Biphenylyltriazinyl group,
Diphenyltriazinyl group,
a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
・酸素原子を含む置換の複素環基（具体例群Ｇ２Ｂ２）：
フェニルジベンゾフラニル基、
メチルジベンゾフラニル基、
ｔ－ブチルジベンゾフラニル基、及び
スピロ［９Ｈ－キサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基。 Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2):
phenyldibenzofuranyl group,
methyldibenzofuranyl group,
The t-butyldibenzofuranyl group, and the monovalent radical of spiro[9H-xanthene-9,9'-[9H]fluorene].
フェニルジベンゾフラニル基、
メチルジベンゾフラニル基、
ｔ－ブチルジベンゾフラニル基、及び
スピロ［９Ｈ－キサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基。 Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2):
phenyldibenzofuranyl group,
methyldibenzofuranyl group,
The t-butyldibenzofuranyl group, and the monovalent radical of spiro[9H-xanthene-9,9'-[9H]fluorene].
・硫黄原子を含む置換の複素環基（具体例群Ｇ２Ｂ３）：
フェニルジベンゾチオフェニル基、
メチルジベンゾチオフェニル基、
ｔ－ブチルジベンゾチオフェニル基、及び
スピロ［９Ｈ－チオキサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基。 Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3):
Phenyldibenzothiophenyl group,
methyldibenzothiophenyl group,
The t-butyldibenzothiophenyl group, and the monovalent radical of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
フェニルジベンゾチオフェニル基、
メチルジベンゾチオフェニル基、
ｔ－ブチルジベンゾチオフェニル基、及び
スピロ［９Ｈ－チオキサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基。 Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3):
Phenyldibenzothiophenyl group,
methyldibenzothiophenyl group,
The t-butyldibenzothiophenyl group, and the monovalent radical of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
・前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基の１つ以上の水素原子が置換基と置き換わった基（具体例群Ｇ２Ｂ４）：
- Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):
前記「１価の複素環基の１つ以上の水素原子」とは、該１価の複素環基の環形成炭素原子に結合している水素原子、ＸＡ及びＹＡの少なくともいずれかがＮＨである場合の窒素原子に結合している水素原子、及びＸＡ及びＹＡの一方がＣＨ２である場合のメチレン基の水素原子から選ばれる１つ以上の水素原子を意味する。
The above "one or more hydrogen atoms of a monovalent heterocyclic group" means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH2 .
・「置換もしくは無置換のアルキル基」
本明細書に記載の「置換もしくは無置換のアルキル基」の具体例（具体例群Ｇ３）としては、以下の無置換のアルキル基（具体例群Ｇ３Ａ）及び置換のアルキル基（具体例群Ｇ３Ｂ）が挙げられる。（ここで、無置換のアルキル基とは「置換もしくは無置換のアルキル基」が「無置換のアルキル基」である場合を指し、置換のアルキル基とは「置換もしくは無置換のアルキル基」が「置換のアルキル基」である場合を指す。）以下、単に「アルキル基」という場合は、「無置換のアルキル基」と「置換のアルキル基」の両方を含む。
「置換のアルキル基」は、「無置換のアルキル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルキル基」の具体例としては、下記の「無置換のアルキル基」（具体例群Ｇ３Ａ）における１つ以上の水素原子が置換基と置き換わった基、及び置換のアルキル基（具体例群Ｇ３Ｂ）の例等が挙げられる。本明細書において、「無置換のアルキル基」におけるアルキル基は、鎖状のアルキル基を意味する。そのため、「無置換のアルキル基」は、直鎖である「無置換のアルキル基」、及び分岐状である「無置換のアルキル基」が含まれる。尚、ここに列挙した「無置換のアルキル基」の例や「置換のアルキル基」の例は、一例に過ぎず、本明細書に記載の「置換のアルキル基」には、具体例群Ｇ３Ｂの「置換のアルキル基」におけるアルキル基自体の水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ３Ｂの「置換のアルキル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted alkyl group"
Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when the term "alkyl group" is simply mentioned, it includes both the "unsubstituted alkyl group" and the "substituted alkyl group".
The term "substituted alkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent.
本明細書に記載の「置換もしくは無置換のアルキル基」の具体例（具体例群Ｇ３）としては、以下の無置換のアルキル基（具体例群Ｇ３Ａ）及び置換のアルキル基（具体例群Ｇ３Ｂ）が挙げられる。（ここで、無置換のアルキル基とは「置換もしくは無置換のアルキル基」が「無置換のアルキル基」である場合を指し、置換のアルキル基とは「置換もしくは無置換のアルキル基」が「置換のアルキル基」である場合を指す。）以下、単に「アルキル基」という場合は、「無置換のアルキル基」と「置換のアルキル基」の両方を含む。
「置換のアルキル基」は、「無置換のアルキル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルキル基」の具体例としては、下記の「無置換のアルキル基」（具体例群Ｇ３Ａ）における１つ以上の水素原子が置換基と置き換わった基、及び置換のアルキル基（具体例群Ｇ３Ｂ）の例等が挙げられる。本明細書において、「無置換のアルキル基」におけるアルキル基は、鎖状のアルキル基を意味する。そのため、「無置換のアルキル基」は、直鎖である「無置換のアルキル基」、及び分岐状である「無置換のアルキル基」が含まれる。尚、ここに列挙した「無置換のアルキル基」の例や「置換のアルキル基」の例は、一例に過ぎず、本明細書に記載の「置換のアルキル基」には、具体例群Ｇ３Ｂの「置換のアルキル基」におけるアルキル基自体の水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ３Ｂの「置換のアルキル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted alkyl group"
Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when the term "alkyl group" is simply mentioned, it includes both the "unsubstituted alkyl group" and the "substituted alkyl group".
The term "substituted alkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent.
・無置換のアルキル基（具体例群Ｇ３Ａ）：
メチル基、
エチル基、
ｎ－プロピル基、
イソプロピル基、
ｎ－ブチル基、
イソブチル基、
ｓ－ブチル基、及び
ｔ－ブチル基。 Unsubstituted alkyl groups (specific example group G3A):
Methyl group,
Ethyl group,
n-propyl group,
isopropyl group,
n-butyl group,
isobutyl group,
s-Butyl group, and t-butyl group.
メチル基、
エチル基、
ｎ－プロピル基、
イソプロピル基、
ｎ－ブチル基、
イソブチル基、
ｓ－ブチル基、及び
ｔ－ブチル基。 Unsubstituted alkyl groups (specific example group G3A):
Methyl group,
Ethyl group,
n-propyl group,
isopropyl group,
n-butyl group,
isobutyl group,
s-Butyl group, and t-butyl group.
・置換のアルキル基（具体例群Ｇ３Ｂ）：
ヘプタフルオロプロピル基（異性体を含む）、
ペンタフルオロエチル基、
２，２，２－トリフルオロエチル基、及び
トリフルオロメチル基。 Substituted alkyl groups (specific example group G3B):
Heptafluoropropyl group (including isomers),
pentafluoroethyl group,
A 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
ヘプタフルオロプロピル基（異性体を含む）、
ペンタフルオロエチル基、
２，２，２－トリフルオロエチル基、及び
トリフルオロメチル基。 Substituted alkyl groups (specific example group G3B):
Heptafluoropropyl group (including isomers),
pentafluoroethyl group,
A 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
・「置換もしくは無置換のアルケニル基」
本明細書に記載の「置換もしくは無置換のアルケニル基」の具体例（具体例群Ｇ４）としては、以下の無置換のアルケニル基（具体例群Ｇ４Ａ）、及び置換のアルケニル基（具体例群Ｇ４Ｂ）等が挙げられる。（ここで、無置換のアルケニル基とは「置換もしくは無置換のアルケニル基」が「無置換のアルケニル基」である場合を指し、「置換のアルケニル基」とは「置換もしくは無置換のアルケニル基」が「置換のアルケニル基」である場合を指す。）本明細書において、単に「アルケニル基」という場合は、「無置換のアルケニル基」と「置換のアルケニル基」の両方を含む。
「置換のアルケニル基」は、「無置換のアルケニル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルケニル基」の具体例としては、下記の「無置換のアルケニル基」（具体例群Ｇ４Ａ）が置換基を有する基、及び置換のアルケニル基（具体例群Ｇ４Ｂ）の例等が挙げられる。尚、ここに列挙した「無置換のアルケニル基」の例や「置換のアルケニル基」の例は、一例に過ぎず、本明細書に記載の「置換のアルケニル基」には、具体例群Ｇ４Ｂの「置換のアルケニル基」におけるアルケニル基自体の水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ４Ｂの「置換のアルケニル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted alkenyl group"
Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when the term "alkenyl group" is simply used, it includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group".
The term "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B). Note that the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent.
本明細書に記載の「置換もしくは無置換のアルケニル基」の具体例（具体例群Ｇ４）としては、以下の無置換のアルケニル基（具体例群Ｇ４Ａ）、及び置換のアルケニル基（具体例群Ｇ４Ｂ）等が挙げられる。（ここで、無置換のアルケニル基とは「置換もしくは無置換のアルケニル基」が「無置換のアルケニル基」である場合を指し、「置換のアルケニル基」とは「置換もしくは無置換のアルケニル基」が「置換のアルケニル基」である場合を指す。）本明細書において、単に「アルケニル基」という場合は、「無置換のアルケニル基」と「置換のアルケニル基」の両方を含む。
「置換のアルケニル基」は、「無置換のアルケニル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルケニル基」の具体例としては、下記の「無置換のアルケニル基」（具体例群Ｇ４Ａ）が置換基を有する基、及び置換のアルケニル基（具体例群Ｇ４Ｂ）の例等が挙げられる。尚、ここに列挙した「無置換のアルケニル基」の例や「置換のアルケニル基」の例は、一例に過ぎず、本明細書に記載の「置換のアルケニル基」には、具体例群Ｇ４Ｂの「置換のアルケニル基」におけるアルケニル基自体の水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ４Ｂの「置換のアルケニル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted alkenyl group"
Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when the term "alkenyl group" is simply used, it includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group".
The term "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B). Note that the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent.
・無置換のアルケニル基（具体例群Ｇ４Ａ）：
ビニル基、
アリル基、
１－ブテニル基、
２－ブテニル基、及び
３－ブテニル基。 Unsubstituted alkenyl groups (specific example group G4A):
Vinyl group,
Allyl groups,
1-butenyl group,
A 2-butenyl group, and a 3-butenyl group.
ビニル基、
アリル基、
１－ブテニル基、
２－ブテニル基、及び
３－ブテニル基。 Unsubstituted alkenyl groups (specific example group G4A):
Vinyl group,
Allyl groups,
1-butenyl group,
A 2-butenyl group, and a 3-butenyl group.
・置換のアルケニル基（具体例群Ｇ４Ｂ）：
１，３－ブタンジエニル基、
１－メチルビニル基、
１－メチルアリル基、
１，１－ジメチルアリル基、
２－メチルアリル基、及び
１，２－ジメチルアリル基。 Substituted alkenyl groups (specific example group G4B):
1,3-butadienyl group,
1-methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-methylallyl group, and 1,2-dimethylallyl group.
１，３－ブタンジエニル基、
１－メチルビニル基、
１－メチルアリル基、
１，１－ジメチルアリル基、
２－メチルアリル基、及び
１，２－ジメチルアリル基。 Substituted alkenyl groups (specific example group G4B):
1,3-butadienyl group,
1-methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-methylallyl group, and 1,2-dimethylallyl group.
・「置換もしくは無置換のアルキニル基」
本明細書に記載の「置換もしくは無置換のアルキニル基」の具体例（具体例群Ｇ５）としては、以下の無置換のアルキニル基（具体例群Ｇ５Ａ）等が挙げられる。（ここで、無置換のアルキニル基とは、「置換もしくは無置換のアルキニル基」が「無置換のアルキニル基」である場合を指す。）以下、単に「アルキニル基」という場合は、「無置換のアルキニル基」と「置換のアルキニル基」の両方を含む。
「置換のアルキニル基」は、「無置換のアルキニル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルキニル基」の具体例としては、下記の「無置換のアルキニル基」（具体例群Ｇ５Ａ）における１つ以上の水素原子が置換基と置き換わった基等が挙げられる。 - "Substituted or unsubstituted alkynyl group"
Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when the term "alkynyl group" is simply used, it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group."
The term "substituted alkynyl group" refers to an "unsubstituted alkynyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include the following "unsubstituted alkynyl group" (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.
本明細書に記載の「置換もしくは無置換のアルキニル基」の具体例（具体例群Ｇ５）としては、以下の無置換のアルキニル基（具体例群Ｇ５Ａ）等が挙げられる。（ここで、無置換のアルキニル基とは、「置換もしくは無置換のアルキニル基」が「無置換のアルキニル基」である場合を指す。）以下、単に「アルキニル基」という場合は、「無置換のアルキニル基」と「置換のアルキニル基」の両方を含む。
「置換のアルキニル基」は、「無置換のアルキニル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルキニル基」の具体例としては、下記の「無置換のアルキニル基」（具体例群Ｇ５Ａ）における１つ以上の水素原子が置換基と置き換わった基等が挙げられる。 - "Substituted or unsubstituted alkynyl group"
Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when the term "alkynyl group" is simply used, it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group."
The term "substituted alkynyl group" refers to an "unsubstituted alkynyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include the following "unsubstituted alkynyl group" (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.
・無置換のアルキニル基（具体例群Ｇ５Ａ）：
エチニル基 Unsubstituted alkynyl groups (specific example group G5A):
Ethynyl group
エチニル基 Unsubstituted alkynyl groups (specific example group G5A):
Ethynyl group
・「置換もしくは無置換のシクロアルキル基」
本明細書に記載の「置換もしくは無置換のシクロアルキル基」の具体例（具体例群Ｇ６）としては、以下の無置換のシクロアルキル基（具体例群Ｇ６Ａ）、及び置換のシクロアルキル基（具体例群Ｇ６Ｂ）等が挙げられる。（ここで、無置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「無置換のシクロアルキル基」である場合を指し、置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「置換のシクロアルキル基」である場合を指す。）本明細書において、単に「シクロアルキル基」という場合は、「無置換のシクロアルキル基」と「置換のシクロアルキル基」の両方を含む。
「置換のシクロアルキル基」は、「無置換のシクロアルキル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のシクロアルキル基」の具体例としては、下記の「無置換のシクロアルキル基」（具体例群Ｇ６Ａ）における１つ以上の水素原子が置換基と置き換わった基、及び置換のシクロアルキル基（具体例群Ｇ６Ｂ）の例等が挙げられる。尚、ここに列挙した「無置換のシクロアルキル基」の例や「置換のシクロアルキル基」の例は、一例に過ぎず、本明細書に記載の「置換のシクロアルキル基」には、具体例群Ｇ６Ｂの「置換のシクロアルキル基」におけるシクロアルキル基自体の炭素原子に結合する１つ以上の水素原子が置換基と置き換わった基、及び具体例群Ｇ６Ｂの「置換のシクロアルキル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted cycloalkyl groups"
Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group".
The term "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group" in the specific example group G6B are replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group" in the specific example group G6B is further replaced with a substituent.
本明細書に記載の「置換もしくは無置換のシクロアルキル基」の具体例（具体例群Ｇ６）としては、以下の無置換のシクロアルキル基（具体例群Ｇ６Ａ）、及び置換のシクロアルキル基（具体例群Ｇ６Ｂ）等が挙げられる。（ここで、無置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「無置換のシクロアルキル基」である場合を指し、置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「置換のシクロアルキル基」である場合を指す。）本明細書において、単に「シクロアルキル基」という場合は、「無置換のシクロアルキル基」と「置換のシクロアルキル基」の両方を含む。
「置換のシクロアルキル基」は、「無置換のシクロアルキル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のシクロアルキル基」の具体例としては、下記の「無置換のシクロアルキル基」（具体例群Ｇ６Ａ）における１つ以上の水素原子が置換基と置き換わった基、及び置換のシクロアルキル基（具体例群Ｇ６Ｂ）の例等が挙げられる。尚、ここに列挙した「無置換のシクロアルキル基」の例や「置換のシクロアルキル基」の例は、一例に過ぎず、本明細書に記載の「置換のシクロアルキル基」には、具体例群Ｇ６Ｂの「置換のシクロアルキル基」におけるシクロアルキル基自体の炭素原子に結合する１つ以上の水素原子が置換基と置き換わった基、及び具体例群Ｇ６Ｂの「置換のシクロアルキル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 - "Substituted or unsubstituted cycloalkyl groups"
Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group".
The term "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group" in the specific example group G6B are replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group" in the specific example group G6B is further replaced with a substituent.
・無置換のシクロアルキル基（具体例群Ｇ６Ａ）：
シクロプロピル基、
シクロブチル基、
シクロペンチル基、
シクロヘキシル基、
１－アダマンチル基、
２－アダマンチル基、
１－ノルボルニル基、及び
２－ノルボルニル基。 Unsubstituted cycloalkyl groups (specific example group G6A):
A cyclopropyl group,
A cyclobutyl group,
Cyclopentyl group,
cyclohexyl group,
1-adamantyl group,
2-adamantyl group,
1-norbornyl group, and 2-norbornyl group.
シクロプロピル基、
シクロブチル基、
シクロペンチル基、
シクロヘキシル基、
１－アダマンチル基、
２－アダマンチル基、
１－ノルボルニル基、及び
２－ノルボルニル基。 Unsubstituted cycloalkyl groups (specific example group G6A):
A cyclopropyl group,
A cyclobutyl group,
Cyclopentyl group,
cyclohexyl group,
1-adamantyl group,
2-adamantyl group,
1-norbornyl group, and 2-norbornyl group.
・置換のシクロアルキル基（具体例群Ｇ６Ｂ）：
４－メチルシクロヘキシル基。 Substituted cycloalkyl groups (specific example group G6B):
4-Methylcyclohexyl group.
４－メチルシクロヘキシル基。 Substituted cycloalkyl groups (specific example group G6B):
4-Methylcyclohexyl group.
・「－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）で表される基」
本明細書に記載の－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）で表される基の具体例（具体例群Ｇ７）としては、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）、
－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）、
－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）、及び
－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）
が挙げられる。ここで、
Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）における複数のＧ１は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）における複数のＧ１は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）における複数のＧ６は、互いに同一であるか、又は異なる。 - "A group represented by -Si( R901 )( R902 )( R903 )"
Specific examples (specific example group G7) of the group represented by --Si(R 901 )(R 902 )(R 903 ) described in this specification include:
-Si(G1)(G1)(G1),
-Si (G1) (G2) (G2),
-Si (G1) (G1) (G2),
-Si(G2)(G2)(G2),
-Si(G3)(G3)(G3), and -Si(G6)(G6)(G6)
Here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.
The multiple G2s in —Si(G1)(G2)(G2) are the same as or different from each other.
The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.
The multiple G2s in —Si(G2)(G2)(G2) are the same as or different from each other.
The multiple G3s in —Si(G3)(G3)(G3) are the same as or different from each other.
The multiple G6s in —Si(G6)(G6)(G6) are the same as or different from each other.
本明細書に記載の－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）で表される基の具体例（具体例群Ｇ７）としては、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）、
－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）、
－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）、及び
－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）
が挙げられる。ここで、
Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）における複数のＧ１は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）における複数のＧ１は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。
－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）における複数のＧ６は、互いに同一であるか、又は異なる。 - "A group represented by -Si( R901 )( R902 )( R903 )"
Specific examples (specific example group G7) of the group represented by --Si(R 901 )(R 902 )(R 903 ) described in this specification include:
-Si(G1)(G1)(G1),
-Si (G1) (G2) (G2),
-Si (G1) (G1) (G2),
-Si(G2)(G2)(G2),
-Si(G3)(G3)(G3), and -Si(G6)(G6)(G6)
Here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.
The multiple G2s in —Si(G1)(G2)(G2) are the same as or different from each other.
The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.
The multiple G2s in —Si(G2)(G2)(G2) are the same as or different from each other.
The multiple G3s in —Si(G3)(G3)(G3) are the same as or different from each other.
The multiple G6s in —Si(G6)(G6)(G6) are the same as or different from each other.
・「－Ｏ－（Ｒ９０４）で表される基」
本明細書に記載の－Ｏ－（Ｒ９０４）で表される基の具体例（具体例群Ｇ８）としては、
－Ｏ（Ｇ１）、
－Ｏ（Ｇ２）、
－Ｏ（Ｇ３）、及び
－Ｏ（Ｇ６）
が挙げられる。
ここで、
Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。 - "A group represented by -O-(R 904 )"
Specific examples (specific example group G8) of the group represented by -O-(R 904 ) described in this specification include:
-O(G1),
-O (G2),
-O(G3) and -O(G6)
Examples include:
Where:
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
本明細書に記載の－Ｏ－（Ｒ９０４）で表される基の具体例（具体例群Ｇ８）としては、
－Ｏ（Ｇ１）、
－Ｏ（Ｇ２）、
－Ｏ（Ｇ３）、及び
－Ｏ（Ｇ６）
が挙げられる。
ここで、
Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。 - "A group represented by -O-(R 904 )"
Specific examples (specific example group G8) of the group represented by -O-(R 904 ) described in this specification include:
-O(G1),
-O (G2),
-O(G3) and -O(G6)
Examples include:
Where:
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
・「－Ｓ－（Ｒ９０５）で表される基」
本明細書に記載の－Ｓ－（Ｒ９０５）で表される基の具体例（具体例群Ｇ９）としては、
－Ｓ（Ｇ１）、
－Ｓ（Ｇ２）、
－Ｓ（Ｇ３）、及び
－Ｓ（Ｇ６）
が挙げられる。
ここで、
Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。 - "A group represented by -S-(R 905 )"
Specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification include:
-S (G1),
-S (G2),
-S(G3) and -S(G6)
Examples include:
Where:
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
本明細書に記載の－Ｓ－（Ｒ９０５）で表される基の具体例（具体例群Ｇ９）としては、
－Ｓ（Ｇ１）、
－Ｓ（Ｇ２）、
－Ｓ（Ｇ３）、及び
－Ｓ（Ｇ６）
が挙げられる。
ここで、
Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。 - "A group represented by -S-(R 905 )"
Specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification include:
-S (G1),
-S (G2),
-S(G3) and -S(G6)
Examples include:
Where:
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
・「－Ｎ（Ｒ９０６）（Ｒ９０７）で表される基」
本明細書に記載の－Ｎ（Ｒ９０６）（Ｒ９０７）で表される基の具体例（具体例群Ｇ１０）としては、
－Ｎ（Ｇ１）（Ｇ１）、
－Ｎ（Ｇ２）（Ｇ２）、
－Ｎ（Ｇ１）（Ｇ２）、
－Ｎ（Ｇ３）（Ｇ３）、及び
－Ｎ（Ｇ６）（Ｇ６）
が挙げられる。
ここで、
Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。
－Ｎ（Ｇ１）（Ｇ１）における複数のＧ１は、互いに同一であるか、又は異なる。
－Ｎ（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
－Ｎ（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。
－Ｎ（Ｇ６）（Ｇ６）における複数のＧ６は、互いに同一であるか、又は異なる。 - "A group represented by -N(R 906 )(R 907 )"
Specific examples (specific example group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification include:
-N(G1)(G1),
-N(G2)(G2),
-N (G1) (G2),
-N(G3)(G3), and -N(G6)(G6)
Examples include:
Where:
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
The multiple G1s in -N(G1)(G1) are the same or different from each other.
The multiple G2s in -N(G2)(G2) are the same or different from each other.
The multiple G3s in -N(G3)(G3) are the same or different.
The multiple G6s in -N(G6)(G6) are the same or different.
本明細書に記載の－Ｎ（Ｒ９０６）（Ｒ９０７）で表される基の具体例（具体例群Ｇ１０）としては、
－Ｎ（Ｇ１）（Ｇ１）、
－Ｎ（Ｇ２）（Ｇ２）、
－Ｎ（Ｇ１）（Ｇ２）、
－Ｎ（Ｇ３）（Ｇ３）、及び
－Ｎ（Ｇ６）（Ｇ６）
が挙げられる。
ここで、
Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。
－Ｎ（Ｇ１）（Ｇ１）における複数のＧ１は、互いに同一であるか、又は異なる。
－Ｎ（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
－Ｎ（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。
－Ｎ（Ｇ６）（Ｇ６）における複数のＧ６は、互いに同一であるか、又は異なる。 - "A group represented by -N(R 906 )(R 907 )"
Specific examples (specific example group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification include:
-N(G1)(G1),
-N(G2)(G2),
-N (G1) (G2),
-N(G3)(G3), and -N(G6)(G6)
Examples include:
Where:
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
The multiple G1s in -N(G1)(G1) are the same or different from each other.
The multiple G2s in -N(G2)(G2) are the same or different from each other.
The multiple G3s in -N(G3)(G3) are the same or different.
The multiple G6s in -N(G6)(G6) are the same or different.
・「ハロゲン原子」
本明細書に記載の「ハロゲン原子」の具体例（具体例群Ｇ１１）としては、フッ素原子、塩素原子、臭素原子、及びヨウ素原子等が挙げられる。 ・"Halogen atoms"
Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
本明細書に記載の「ハロゲン原子」の具体例（具体例群Ｇ１１）としては、フッ素原子、塩素原子、臭素原子、及びヨウ素原子等が挙げられる。 ・"Halogen atoms"
Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
・「置換もしくは無置換のフルオロアルキル基」
本明細書に記載の「置換もしくは無置換のフルオロアルキル基」は、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している少なくとも１つの水素原子がフッ素原子と置き換わった基を意味し、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している全ての水素原子がフッ素原子で置き換わった基（パーフルオロ基）も含む。「無置換のフルオロアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。「置換のフルオロアルキル基」は、「フルオロアルキル基」の１つ以上の水素原子が置換基と置き換わった基を意味する。尚、本明細書に記載の「置換のフルオロアルキル基」には、「置換のフルオロアルキル基」におけるアルキル鎖の炭素原子に結合する１つ以上の水素原子がさらに置換基と置き換わった基、及び「置換のフルオロアルキル基」における置換基の１つ以上の水素原子がさらに置換基と置き換わった基も含まれる。「無置換のフルオロアルキル基」の具体例としては、前記「アルキル基」（具体例群Ｇ３）における１つ以上の水素原子がフッ素原子と置き換わった基の例等が挙げられる。 - "Substituted or unsubstituted fluoroalkyl groups"
The term "substituted or unsubstituted fluoroalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of groups in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with fluorine atoms.
本明細書に記載の「置換もしくは無置換のフルオロアルキル基」は、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している少なくとも１つの水素原子がフッ素原子と置き換わった基を意味し、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している全ての水素原子がフッ素原子で置き換わった基（パーフルオロ基）も含む。「無置換のフルオロアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。「置換のフルオロアルキル基」は、「フルオロアルキル基」の１つ以上の水素原子が置換基と置き換わった基を意味する。尚、本明細書に記載の「置換のフルオロアルキル基」には、「置換のフルオロアルキル基」におけるアルキル鎖の炭素原子に結合する１つ以上の水素原子がさらに置換基と置き換わった基、及び「置換のフルオロアルキル基」における置換基の１つ以上の水素原子がさらに置換基と置き換わった基も含まれる。「無置換のフルオロアルキル基」の具体例としては、前記「アルキル基」（具体例群Ｇ３）における１つ以上の水素原子がフッ素原子と置き換わった基の例等が挙げられる。 - "Substituted or unsubstituted fluoroalkyl groups"
The term "substituted or unsubstituted fluoroalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of groups in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with fluorine atoms.
・「置換もしくは無置換のハロアルキル基」
本明細書に記載の「置換もしくは無置換のハロアルキル基」は、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している少なくとも１つの水素原子がハロゲン原子と置き換わった基を意味し、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している全ての水素原子がハロゲン原子で置き換わった基も含む。「無置換のハロアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。「置換のハロアルキル基」は、「ハロアルキル基」の１つ以上の水素原子が置換基と置き換わった基を意味する。尚、本明細書に記載の「置換のハロアルキル基」には、「置換のハロアルキル基」におけるアルキル鎖の炭素原子に結合する１つ以上の水素原子がさらに置換基と置き換わった基、及び「置換のハロアルキル基」における置換基の１つ以上の水素原子がさらに置換基と置き換わった基も含まれる。「無置換のハロアルキル基」の具体例としては、前記「アルキル基」（具体例群Ｇ３）における１つ以上の水素原子がハロゲン原子と置き換わった基の例等が挙げられる。ハロアルキル基をハロゲン化アルキル基と称する場合がある。 - "Substituted or unsubstituted haloalkyl group"
The term "substituted or unsubstituted haloalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.
本明細書に記載の「置換もしくは無置換のハロアルキル基」は、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している少なくとも１つの水素原子がハロゲン原子と置き換わった基を意味し、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している全ての水素原子がハロゲン原子で置き換わった基も含む。「無置換のハロアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。「置換のハロアルキル基」は、「ハロアルキル基」の１つ以上の水素原子が置換基と置き換わった基を意味する。尚、本明細書に記載の「置換のハロアルキル基」には、「置換のハロアルキル基」におけるアルキル鎖の炭素原子に結合する１つ以上の水素原子がさらに置換基と置き換わった基、及び「置換のハロアルキル基」における置換基の１つ以上の水素原子がさらに置換基と置き換わった基も含まれる。「無置換のハロアルキル基」の具体例としては、前記「アルキル基」（具体例群Ｇ３）における１つ以上の水素原子がハロゲン原子と置き換わった基の例等が挙げられる。ハロアルキル基をハロゲン化アルキル基と称する場合がある。 - "Substituted or unsubstituted haloalkyl group"
The term "substituted or unsubstituted haloalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.
・「置換もしくは無置換のアルコキシ基」
本明細書に記載の「置換もしくは無置換のアルコキシ基」の具体例としては、－Ｏ（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。「無置換のアルコキシ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。 - "Substituted or unsubstituted alkoxy group"
A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
本明細書に記載の「置換もしくは無置換のアルコキシ基」の具体例としては、－Ｏ（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。「無置換のアルコキシ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。 - "Substituted or unsubstituted alkoxy group"
A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
・「置換もしくは無置換のアルキルチオ基」
本明細書に記載の「置換もしくは無置換のアルキルチオ基」の具体例としては、－Ｓ（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。「無置換のアルキルチオ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。 - "Substituted or unsubstituted alkylthio group"
A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
本明細書に記載の「置換もしくは無置換のアルキルチオ基」の具体例としては、－Ｓ（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。「無置換のアルキルチオ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。 - "Substituted or unsubstituted alkylthio group"
A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
・「置換もしくは無置換のアリールオキシ基」
本明細書に記載の「置換もしくは無置換のアリールオキシ基」の具体例としては、－Ｏ（Ｇ１）で表される基であり、ここで、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。「無置換のアリールオキシ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０であり、より好ましくは６～１８である。 - "Substituted or unsubstituted aryloxy group"
A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
本明細書に記載の「置換もしくは無置換のアリールオキシ基」の具体例としては、－Ｏ（Ｇ１）で表される基であり、ここで、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。「無置換のアリールオキシ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０であり、より好ましくは６～１８である。 - "Substituted or unsubstituted aryloxy group"
A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
・「置換もしくは無置換のアリールチオ基」
本明細書に記載の「置換もしくは無置換のアリールチオ基」の具体例としては、－Ｓ（Ｇ１）で表される基であり、ここで、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。「無置換のアリールチオ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０であり、より好ましくは６～１８である。 - "Substituted or unsubstituted arylthio group"
A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
本明細書に記載の「置換もしくは無置換のアリールチオ基」の具体例としては、－Ｓ（Ｇ１）で表される基であり、ここで、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。「無置換のアリールチオ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０であり、より好ましくは６～１８である。 - "Substituted or unsubstituted arylthio group"
A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
・「置換もしくは無置換のトリアルキルシリル基」
本明細書に記載の「トリアルキルシリル基」の具体例としては、－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。「トリアルキルシリル基」の各アルキル基の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０であり、より好ましくは１～６である。 - "Substituted or unsubstituted trialkylsilyl group"
A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.
本明細書に記載の「トリアルキルシリル基」の具体例としては、－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。「トリアルキルシリル基」の各アルキル基の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０であり、より好ましくは１～６である。 - "Substituted or unsubstituted trialkylsilyl group"
A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.
・「置換もしくは無置換のアラルキル基」
本明細書に記載の「置換もしくは無置換のアラルキル基」の具体例としては、－（Ｇ３）－（Ｇ１）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」であり、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。従って、「アラルキル基」は、「アルキル基」の水素原子が置換基としての「アリール基」と置き換わった基であり、「置換のアルキル基」の一態様である。「無置換のアラルキル基」は、「無置換のアリール基」が置換した「無置換のアルキル基」であり、「無置換のアラルキル基」の炭素数は、本明細書に別途記載のない限り、７～５０であり、好ましくは７～３０であり、より好ましくは７～１８である。
「置換もしくは無置換のアラルキル基」の具体例としては、ベンジル基、１－フェニルエチル基、２－フェニルエチル基、１－フェニルイソプロピル基、２－フェニルイソプロピル基、フェニル－ｔ－ブチル基、α－ナフチルメチル基、１－α－ナフチルエチル基、２－α－ナフチルエチル基、１－α－ナフチルイソプロピル基、２－α－ナフチルイソプロピル基、β－ナフチルメチル基、１－β－ナフチルエチル基、２－β－ナフチルエチル基、１－β－ナフチルイソプロピル基、及び２－β－ナフチルイソプロピル基等が挙げられる。 - "Substituted or unsubstituted aralkyl group"
A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one aspect of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
Specific examples of the "substituted or unsubstituted aralkyl group" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.
本明細書に記載の「置換もしくは無置換のアラルキル基」の具体例としては、－（Ｇ３）－（Ｇ１）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」であり、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。従って、「アラルキル基」は、「アルキル基」の水素原子が置換基としての「アリール基」と置き換わった基であり、「置換のアルキル基」の一態様である。「無置換のアラルキル基」は、「無置換のアリール基」が置換した「無置換のアルキル基」であり、「無置換のアラルキル基」の炭素数は、本明細書に別途記載のない限り、７～５０であり、好ましくは７～３０であり、より好ましくは７～１８である。
「置換もしくは無置換のアラルキル基」の具体例としては、ベンジル基、１－フェニルエチル基、２－フェニルエチル基、１－フェニルイソプロピル基、２－フェニルイソプロピル基、フェニル－ｔ－ブチル基、α－ナフチルメチル基、１－α－ナフチルエチル基、２－α－ナフチルエチル基、１－α－ナフチルイソプロピル基、２－α－ナフチルイソプロピル基、β－ナフチルメチル基、１－β－ナフチルエチル基、２－β－ナフチルエチル基、１－β－ナフチルイソプロピル基、及び２－β－ナフチルイソプロピル基等が挙げられる。 - "Substituted or unsubstituted aralkyl group"
A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one aspect of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
Specific examples of the "substituted or unsubstituted aralkyl group" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.
本明細書に記載の置換もしくは無置換のアリール基は、本明細書に別途記載のない限り、好ましくはフェニル基、ｐ－ビフェニル基、ｍ－ビフェニル基、ｏ－ビフェニル基、ｐ－ターフェニル－４－イル基、ｐ－ターフェニル－３－イル基、ｐ－ターフェニル－２－イル基、ｍ－ターフェニル－４－イル基、ｍ－ターフェニル－３－イル基、ｍ－ターフェニル－２－イル基、ｏ－ターフェニル－４－イル基、ｏ－ターフェニル－３－イル基、ｏ－ターフェニル－２－イル基、１－ナフチル基、２－ナフチル基、アントリル基、フェナントリル基、ピレニル基、クリセニル基、トリフェニレニル基、フルオレニル基、９，９’－スピロビフルオレニル基、９，９－ジメチルフルオレニル基、及び９，９－ジフェニルフルオレニル基等である。
Unless otherwise specified herein, the substituted or unsubstituted aryl group described herein is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a o-terphenyl-4-yl group, a o-terphenyl-3-yl group, a o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, and a 9,9-diphenylfluorenyl group.
本明細書に記載の置換もしくは無置換の複素環基は、本明細書に別途記載のない限り、好ましくはピリジル基、ピリミジニル基、トリアジニル基、キノリル基、イソキノリル基、キナゾリニル基、ベンゾイミダゾリル基、フェナントロリニル基、カルバゾリル基（１－カルバゾリル基、２－カルバゾリル基、３－カルバゾリル基、４－カルバゾリル基、又は９－カルバゾリル基）、ベンゾカルバゾリル基、アザカルバゾリル基、ジアザカルバゾリル基、ジベンゾフラニル基、ナフトベンゾフラニル基、アザジベンゾフラニル基、ジアザジベンゾフラニル基、ジベンゾチオフェニル基、ナフトベンゾチオフェニル基、アザジベンゾチオフェニル基、ジアザジベンゾチオフェニル基、（９－フェニル）カルバゾリル基（（９－フェニル）カルバゾール－１－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、又は（９－フェニル）カルバゾール－４－イル基）、（９－ビフェニリル）カルバゾリル基、（９－フェニル）フェニルカルバゾリル基、ジフェニルカルバゾール－９－イル基、フェニルカルバゾール－９－イル基、フェニルトリアジニル基、ビフェニリルトリアジニル基、ジフェニルトリアジニル基、フェニルジベンゾフラニル基、及びフェニルジベンゾチオフェニル基等である。
Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzofuranyl group, a dibenzothiophenyl group, a ... These include zadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
本明細書において、カルバゾリル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。
In this specification, unless otherwise specified, the carbazolyl group is specifically any of the following groups:
本明細書において、（９－フェニル）カルバゾリル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。
In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:
前記一般式（ＴＥＭＰ－Ｃｚ１）～（ＴＥＭＰ－Ｃｚ９）中、＊は、結合部位を表す。
In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a binding site.
本明細書において、ジベンゾフラニル基、及びジベンゾチオフェニル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。
In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.
前記一般式（ＴＥＭＰ－３４）～（ＴＥＭＰ－４１）中、＊は、結合部位を表す。
In the above general formulas (TEMP-34) to (TEMP-41), * represents a binding site.
本明細書に記載の置換もしくは無置換のアルキル基は、本明細書に別途記載のない限り、好ましくはメチル基、エチル基、プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、及びｔ－ブチル基等である。
Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
・「置換もしくは無置換のアリーレン基」
本明細書に記載の「置換もしくは無置換のアリーレン基」は、別途記載のない限り、上記「置換もしくは無置換のアリール基」からアリール環上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換のアリーレン基」の具体例（具体例群Ｇ１２）としては、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」からアリール環上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 - "Substituted or unsubstituted arylene group"
Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.
本明細書に記載の「置換もしくは無置換のアリーレン基」は、別途記載のない限り、上記「置換もしくは無置換のアリール基」からアリール環上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換のアリーレン基」の具体例（具体例群Ｇ１２）としては、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」からアリール環上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 - "Substituted or unsubstituted arylene group"
Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.
・「置換もしくは無置換の２価の複素環基」
本明細書に記載の「置換もしくは無置換の２価の複素環基」は、別途記載のない限り、上記「置換もしくは無置換の複素環基」から複素環上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換の２価の複素環基」の具体例（具体例群Ｇ１３）としては、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」から複素環上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 - "Substituted or unsubstituted divalent heterocyclic group"
The "substituted or unsubstituted divalent heterocyclic group" described in this specification is, unless otherwise specified, a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
本明細書に記載の「置換もしくは無置換の２価の複素環基」は、別途記載のない限り、上記「置換もしくは無置換の複素環基」から複素環上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換の２価の複素環基」の具体例（具体例群Ｇ１３）としては、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」から複素環上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 - "Substituted or unsubstituted divalent heterocyclic group"
The "substituted or unsubstituted divalent heterocyclic group" described in this specification is, unless otherwise specified, a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
・「置換もしくは無置換のアルキレン基」
本明細書に記載の「置換もしくは無置換のアルキレン基」は、別途記載のない限り、上記「置換もしくは無置換のアルキル基」からアルキル鎖上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換のアルキレン基」の具体例（具体例群Ｇ１４）としては、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」からアルキル鎖上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 - "Substituted or unsubstituted alkylene group"
Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.
本明細書に記載の「置換もしくは無置換のアルキレン基」は、別途記載のない限り、上記「置換もしくは無置換のアルキル基」からアルキル鎖上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換のアルキレン基」の具体例（具体例群Ｇ１４）としては、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」からアルキル鎖上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 - "Substituted or unsubstituted alkylene group"
Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.
本明細書に記載の置換もしくは無置換のアリーレン基は、本明細書に別途記載のない限り、好ましくは下記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－６８）のいずれかの基である。
Unless otherwise specified herein, the substituted or unsubstituted arylene group described herein is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
前記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－５２）中、Ｑ１～Ｑ１０は、それぞれ独立に、水素原子、又は置換基である。
前記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－５２）中、＊は、結合部位を表す。 In the above general formulas (TEMP-42) to (TEMP-52), Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
In the above general formulae (TEMP-42) to (TEMP-52), * represents a binding site.
前記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－５２）中、＊は、結合部位を表す。 In the above general formulas (TEMP-42) to (TEMP-52), Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
In the above general formulae (TEMP-42) to (TEMP-52), * represents a binding site.
前記一般式（ＴＥＭＰ－５３）～（ＴＥＭＰ－６２）中、Ｑ１～Ｑ１０は、それぞれ独立に、水素原子、又は置換基である。
式Ｑ９及びＱ１０は、単結合を介して互いに結合して環を形成してもよい。
前記一般式（ＴＥＭＰ－５３）～（ＴＥＭＰ－６２）中、＊は、結合部位を表す。 In the above general formulas (TEMP-53) to (TEMP-62), Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
In the above general formulae (TEMP-53) to (TEMP-62), * represents a binding site.
式Ｑ９及びＱ１０は、単結合を介して互いに結合して環を形成してもよい。
前記一般式（ＴＥＭＰ－５３）～（ＴＥＭＰ－６２）中、＊は、結合部位を表す。 In the above general formulas (TEMP-53) to (TEMP-62), Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
In the above general formulae (TEMP-53) to (TEMP-62), * represents a binding site.
前記一般式（ＴＥＭＰ－６３）～（ＴＥＭＰ－６８）中、Ｑ１～Ｑ８は、それぞれ独立に、水素原子、又は置換基である。
前記一般式（ＴＥＭＰ－６３）～（ＴＥＭＰ－６８）中、＊は、結合部位を表す。 In the above general formulas (TEMP-63) to (TEMP-68), Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
In the above general formulas (TEMP-63) to (TEMP-68), * represents a binding site.
前記一般式（ＴＥＭＰ－６３）～（ＴＥＭＰ－６８）中、＊は、結合部位を表す。 In the above general formulas (TEMP-63) to (TEMP-68), Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
In the above general formulas (TEMP-63) to (TEMP-68), * represents a binding site.
本明細書に記載の置換もしくは無置換の２価の複素環基は、本明細書に別途記載のない限り、好ましくは下記一般式（ＴＥＭＰ－６９）～（ＴＥＭＰ－１０２）のいずれかの基である。
The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.
前記一般式（ＴＥＭＰ－６９）～（ＴＥＭＰ－８２）中、Ｑ１～Ｑ９は、それぞれ独立に、水素原子、又は置換基である。
In the above general formulas (TEMP-69) to (TEMP-82), Q 1 to Q 9 each independently represent a hydrogen atom or a substituent.
前記一般式（ＴＥＭＰ－８３）～（ＴＥＭＰ－１０２）中、Ｑ１～Ｑ８は、それぞれ独立に、水素原子、又は置換基である。
In the above general formulas (TEMP-83) to (TEMP-102), Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
以上が、「本明細書に記載の置換基」についての説明である。
The above is an explanation of "the substituents described in this specification."
・「結合して環を形成する場合」
本明細書において、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合せず」という場合は、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合と、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合と、「隣接する２つ以上からなる組の１組以上が、互いに結合しない」場合と、を意味する。
本明細書における、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合、及び「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合（以下、これらの場合をまとめて「結合して環を形成する場合」と称する場合がある。）について、以下、説明する。母骨格がアントラセン環である下記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物の場合を例として説明する。 ・"When bonded to form a ring"
In this specification, the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other".
In this specification, the cases where "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocyclic ring" and "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they are bonded to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the mother skeleton is an anthracene ring, will be explained as an example.
本明細書において、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合せず」という場合は、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合と、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合と、「隣接する２つ以上からなる組の１組以上が、互いに結合しない」場合と、を意味する。
本明細書における、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合、及び「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合（以下、これらの場合をまとめて「結合して環を形成する場合」と称する場合がある。）について、以下、説明する。母骨格がアントラセン環である下記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物の場合を例として説明する。 ・"When bonded to form a ring"
In this specification, the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other".
In this specification, the cases where "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocyclic ring" and "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they are bonded to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the mother skeleton is an anthracene ring, will be explained as an example.
例えば、Ｒ９２１～Ｒ９３０のうちの「隣接する２つ以上からなる組の１組以上が、互いに結合して、環を形成する」場合において、１組となる隣接する２つからなる組とは、Ｒ９２１とＲ９２２との組、Ｒ９２２とＲ９２３との組、Ｒ９２３とＲ９２４との組、Ｒ９２４とＲ９３０との組、Ｒ９３０とＲ９２５との組、Ｒ９２５とＲ９２６との組、Ｒ９２６とＲ９２７との組、Ｒ９２７とＲ９２８との組、Ｒ９２８とＲ９２９との組、並びにＲ９２９とＲ９２１との組である。
For example, in the case where "one or more pairs of adjacent two or more of R 921 to R 930 are bonded to each other to form a ring", the pair of adjacent two that constitutes one group includes the pair of R 921 and R 922 , the pair of R 922 and R 923 , the pair of R 923 and R 924 , the pair of R 924 and R 930 , the pair of R 930 and R 925 , the pair of R 925 and R 926 , the pair of R 926 and R 927 , the pair of R 927 and R 928 , the pair of R 928 and R 929 , and the pair of R 929 and R 921 .
上記「１組以上」とは、上記隣接する２つ以上からなる組の２組以上が同時に環を形成してもよいことを意味する。例えば、Ｒ９２１とＲ９２２とが互いに結合して環ＱＡを形成し、同時にＲ９２５とＲ９２６とが互いに結合して環ＱＢを形成した場合は、前記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物は、下記一般式（ＴＥＭＰ－１０４）で表される。
The above "one or more pairs" means that two or more pairs of the adjacent two or more pairs may simultaneously form a ring. For example, when R 921 and R 922 are bonded to each other to form a ring Q A , and R 925 and R 926 are bonded to each other to form a ring Q B , the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
「隣接する２つ以上からなる組」が環を形成する場合とは、前述の例のように隣接する「２つ」からなる組が結合する場合だけではなく、隣接する「３つ以上」からなる組が結合する場合も含む。例えば、Ｒ９２１とＲ９２２とが互いに結合して環ＱＡを形成し、かつ、Ｒ９２２とＲ９２３とが互いに結合して環ＱＣを形成し、互いに隣接する３つ（Ｒ９２１、Ｒ９２２及びＲ９２３）からなる組が互いに結合して環を形成して、アントラセン母骨格に縮合する場合を意味し、この場合、前記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物は、下記一般式（ＴＥＭＰ－１０５）で表される。下記一般式（ＴＥＭＰ－１０５）において、環ＱＡ及び環ＱＣは、Ｒ９２２を共有する。
The case where "a set of two or more adjacent rings" forms a ring includes not only the case where a set of "two" adjacent rings is bonded as in the above example, but also the case where a set of "three or more adjacent rings is bonded. For example, it means the case where R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , and a set of three adjacent rings (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and are condensed to the anthracene skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .
形成される「単環」、又は「縮合環」は、形成された環のみの構造として、飽和の環であっても不飽和の環であってもよい。「隣接する２つからなる組の１組」が「単環」、又は「縮合環」を形成する場合であっても、当該「単環」、又は「縮合環」は、飽和の環、又は不飽和の環を形成することができる。例えば、前記一般式（ＴＥＭＰ－１０４）において形成された環ＱＡ及び環ＱＢは、それぞれ、「単環」又は「縮合環」である。また、前記一般式（ＴＥＭＰ－１０５）において形成された環ＱＡ、及び環ＱＣは、「縮合環」である。前記一般式（ＴＥＭＰ－１０５）の環ＱＡと環ＱＣとは、環ＱＡと環ＱＣとが縮合することによって縮合環となっている。前記一般式（ＴＭＥＰ－１０４）の環ＱＡがベンゼン環であれば、環ＱＡは、単環である。前記一般式（ＴＭＥＰ－１０４）の環ＱＡがナフタレン環であれば、環ＱＡは、縮合環である。
The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even if "one of the pairs of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" can form a saturated ring or an unsaturated ring. For example, the ring Q A and the ring Q B formed in the general formula (TEMP-104) are "monocyclic rings" or "fused rings", respectively. Furthermore, the ring Q A and the ring Q C formed in the general formula (TEMP-105) are "fused rings". The ring Q A and the ring Q C in the general formula (TEMP-105) are fused rings by the fusion of the ring Q A and the ring Q C. If the ring Q A in the general formula (TMEP-104) is a benzene ring, the ring Q A is a monocyclic ring. When ring Q 1 A in the above general formula (TMEP-104) is a naphthalene ring, ring Q 1 A is a fused ring.
「不飽和の環」には、芳香族炭化水素環、芳香族複素環の他、環構造中に不飽和結合、即ち、二重結合及び／又は三重結合を有する脂肪族炭化水素環（例えば、シクロヘキセン、シクロヘキサジエン等）、及び不飽和結合を有する非芳香族複素環（例えば、ジヒドロピラン、イミダゾリン、ピラゾリン、キノリジン、インドリン、イソインドリン等）が含まれる。「飽和の環」には、不飽和結合を有しない脂肪族炭化水素環、又は不飽和結合を有しない非芳香族複素環が含まれる。
芳香族炭化水素環の具体例としては、具体例群Ｇ１において具体例として挙げられた基が水素原子によって終端された構造が挙げられる。
芳香族複素環の具体例としては、具体例群Ｇ２において具体例として挙げられた芳香族複素環基が水素原子によって終端された構造が挙げられる。
脂肪族炭化水素環の具体例としては、具体例群Ｇ６において具体例として挙げられた基が水素原子によって終端された構造が挙げられる。
「環を形成する」とは、母骨格の複数の原子のみ、あるいは母骨格の複数の原子とさらに１以上の任意の原子で環を形成することを意味する。例えば、前記一般式（ＴＥＭＰ－１０４）に示す、Ｒ９２１とＲ９２２とが互いに結合して形成された環ＱＡは、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２が結合するアントラセン骨格の炭素原子と、１以上の任意の原子とで形成する環を意味する。具体例としては、Ｒ９２１とＲ９２２とで環ＱＡを形成する場合において、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２とが結合するアントラセン骨格の炭素原子と、４つの炭素原子とで単環の不飽和の環を形成する場合、Ｒ９２１とＲ９２２とで形成する環は、ベンゼン環である。 The "unsaturated ring" includes aromatic hydrocarbon rings and aromatic heterocycles, as well as aliphatic hydrocarbon rings having an unsaturated bond in the ring structure, i.e., a double bond and/or a triple bond (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The "saturated ring" includes an aliphatic hydrocarbon ring having no unsaturated bond, or a non-aromatic heterocycle having no unsaturated bond.
Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom.
Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom.
"Forming a ring" means forming a ring only with a plurality of atoms of the mother skeleton, or a plurality of atoms of the mother skeleton and one or more arbitrary atoms. For example, the ring QA formed by bonding R 921 and R 922 to each other in the general formula (TEMP-104) means a ring formed by the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and one or more arbitrary atoms. As a specific example, when R 921 and R 922 form a ring QA , when the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.
芳香族炭化水素環の具体例としては、具体例群Ｇ１において具体例として挙げられた基が水素原子によって終端された構造が挙げられる。
芳香族複素環の具体例としては、具体例群Ｇ２において具体例として挙げられた芳香族複素環基が水素原子によって終端された構造が挙げられる。
脂肪族炭化水素環の具体例としては、具体例群Ｇ６において具体例として挙げられた基が水素原子によって終端された構造が挙げられる。
「環を形成する」とは、母骨格の複数の原子のみ、あるいは母骨格の複数の原子とさらに１以上の任意の原子で環を形成することを意味する。例えば、前記一般式（ＴＥＭＰ－１０４）に示す、Ｒ９２１とＲ９２２とが互いに結合して形成された環ＱＡは、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２が結合するアントラセン骨格の炭素原子と、１以上の任意の原子とで形成する環を意味する。具体例としては、Ｒ９２１とＲ９２２とで環ＱＡを形成する場合において、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２とが結合するアントラセン骨格の炭素原子と、４つの炭素原子とで単環の不飽和の環を形成する場合、Ｒ９２１とＲ９２２とで形成する環は、ベンゼン環である。 The "unsaturated ring" includes aromatic hydrocarbon rings and aromatic heterocycles, as well as aliphatic hydrocarbon rings having an unsaturated bond in the ring structure, i.e., a double bond and/or a triple bond (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The "saturated ring" includes an aliphatic hydrocarbon ring having no unsaturated bond, or a non-aromatic heterocycle having no unsaturated bond.
Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom.
Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom.
"Forming a ring" means forming a ring only with a plurality of atoms of the mother skeleton, or a plurality of atoms of the mother skeleton and one or more arbitrary atoms. For example, the ring QA formed by bonding R 921 and R 922 to each other in the general formula (TEMP-104) means a ring formed by the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and one or more arbitrary atoms. As a specific example, when R 921 and R 922 form a ring QA , when the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.
ここで、「任意の原子」は、本明細書に別途記載のない限り、好ましくは、炭素原子、窒素原子、酸素原子、及び硫黄原子からなる群から選択される少なくとも１種の原子である。任意の原子において（例えば、炭素原子、又は窒素原子の場合）、環を形成しない結合は、水素原子等で終端されてもよいし、後述する「任意の置換基」で置換されてもよい。炭素原子以外の任意の原子を含む場合、形成される環は複素環である。
単環又は縮合環を構成する「１以上の任意の原子」は、本明細書に別途記載のない限り、好ましくは２個以上１５個以下であり、より好ましくは３個以上１２個以下であり、さらに好ましくは３個以上５個以下である。
本明細書に別途記載のない限り、「単環」、及び「縮合環」のうち、好ましくは「単環」である。
本明細書に別途記載のない限り、「飽和の環」、及び「不飽和の環」のうち、好ましくは「不飽和の環」である。
本明細書に別途記載のない限り、「単環」は、好ましくはベンゼン環である。
本明細書に別途記載のない限り、「不飽和の環」は、好ましくはベンゼン環である。
「隣接する２つ以上からなる組の１組以上」が、「互いに結合して、置換もしくは無置換の単環を形成する」場合、又は「互いに結合して、置換もしくは無置換の縮合環を形成する」場合、本明細書に別途記載のない限り、好ましくは、隣接する２つ以上からなる組の１組以上が、互いに結合して、母骨格の複数の原子と、１個以上１５個以下の炭素原子、窒素原子、酸素原子、及び硫黄原子からなる群から選択される少なくとも１種の原子とからなる置換もしくは無置換の「不飽和の環」を形成する。 Here, unless otherwise specified in the present specification, the "arbitrary atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In the arbitrary atom (for example, in the case of a carbon atom or a nitrogen atom), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary atom other than a carbon atom is included, the ring formed is a heterocycle.
Unless otherwise specified in this specification, the "one or more any atoms" constituting the single ring or the fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.
Unless otherwise specified in this specification, of the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred.
Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred.
Unless otherwise specified in this specification, a "monocyclic ring" is preferably a benzene ring.
Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.
When "one or more of a set consisting of two or more adjacent rings""combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring", unless otherwise specified in this specification, preferably, one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
単環又は縮合環を構成する「１以上の任意の原子」は、本明細書に別途記載のない限り、好ましくは２個以上１５個以下であり、より好ましくは３個以上１２個以下であり、さらに好ましくは３個以上５個以下である。
本明細書に別途記載のない限り、「単環」、及び「縮合環」のうち、好ましくは「単環」である。
本明細書に別途記載のない限り、「飽和の環」、及び「不飽和の環」のうち、好ましくは「不飽和の環」である。
本明細書に別途記載のない限り、「単環」は、好ましくはベンゼン環である。
本明細書に別途記載のない限り、「不飽和の環」は、好ましくはベンゼン環である。
「隣接する２つ以上からなる組の１組以上」が、「互いに結合して、置換もしくは無置換の単環を形成する」場合、又は「互いに結合して、置換もしくは無置換の縮合環を形成する」場合、本明細書に別途記載のない限り、好ましくは、隣接する２つ以上からなる組の１組以上が、互いに結合して、母骨格の複数の原子と、１個以上１５個以下の炭素原子、窒素原子、酸素原子、及び硫黄原子からなる群から選択される少なくとも１種の原子とからなる置換もしくは無置換の「不飽和の環」を形成する。 Here, unless otherwise specified in the present specification, the "arbitrary atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In the arbitrary atom (for example, in the case of a carbon atom or a nitrogen atom), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary atom other than a carbon atom is included, the ring formed is a heterocycle.
Unless otherwise specified in this specification, the "one or more any atoms" constituting the single ring or the fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.
Unless otherwise specified in this specification, of the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred.
Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred.
Unless otherwise specified in this specification, a "monocyclic ring" is preferably a benzene ring.
Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.
When "one or more of a set consisting of two or more adjacent rings""combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring", unless otherwise specified in this specification, preferably, one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
上記の「単環」、又は「縮合環」が置換基を有する場合の置換基は、例えば後述する「任意の置換基」である。上記の「単環」、又は「縮合環」が置換基を有する場合の置換基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基である。
上記の「飽和の環」、又は「不飽和の環」が置換基を有する場合の置換基は、例えば後述する「任意の置換基」である。上記の「単環」、又は「縮合環」が置換基を有する場合の置換基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基である。
以上が、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合、及び「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合（「結合して環を形成する場合」）についての説明である。 When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned section "Substituents described in this specification".
When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification".
The above is an explanation of the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring"("combined to form a ring").
上記の「飽和の環」、又は「不飽和の環」が置換基を有する場合の置換基は、例えば後述する「任意の置換基」である。上記の「単環」、又は「縮合環」が置換基を有する場合の置換基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基である。
以上が、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合、及び「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合（「結合して環を形成する場合」）についての説明である。 When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned section "Substituents described in this specification".
When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification".
The above is an explanation of the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring"("combined to form a ring").
・「置換もしくは無置換の」という場合の置換基
本明細書における一実施形態においては、前記「置換もしくは無置換の」という場合の置換基（本明細書において、「任意の置換基」と呼ぶことがある。）は、例えば、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、及び
無置換の環形成原子数５～５０の複素環基
からなる群から選択される基等であり、
ここで、Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の複素環基である。
Ｒ９０１が２個以上存在する場合、２個以上のＲ９０１は、互いに同一であるか、又は異なり、
Ｒ９０２が２個以上存在する場合、２個以上のＲ９０２は、互いに同一であるか、又は異なり、
Ｒ９０３が２個以上存在する場合、２個以上のＲ９０３は、互いに同一であるか、又は異なり、
Ｒ９０４が２個以上存在する場合、２個以上のＲ９０４は、互いに同一であるか、又は異なり、
Ｒ９０５が２個以上存在する場合、２個以上のＲ９０５は、互いに同一であるか、又は異なり、
Ｒ９０６が２個以上存在する場合、２個以上のＲ９０６は、互いに同一であるか、又は異なり、
Ｒ９０７が２個以上存在する場合、２個以上のＲ９０７は、互いに同一であるか又は異なる。 Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) are, for example,
an unsubstituted alkyl group having 1 to 50 carbon atoms;
an unsubstituted alkenyl group having 2 to 50 carbon atoms,
an unsubstituted alkynyl group having 2 to 50 carbon atoms,
an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring atoms,
In the formula, R 901 to R 907 each independently represent
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
When two or more R 901 are present, the two or more R 901 are the same or different from each other,
When two or more R 902 are present, the two or more R 902 are the same or different from each other,
When two or more R 903 are present, the two or more R 903 are the same or different from each other,
When two or more R 904 are present, the two or more R 904 are the same or different from each other,
When two or more R 905 are present, the two or more R 905 are the same or different from each other,
When two or more R 906 are present, the two or more R 906 are the same or different from each other,
When two or more R 907 are present, the two or more R 907 are the same or different.
本明細書における一実施形態においては、前記「置換もしくは無置換の」という場合の置換基（本明細書において、「任意の置換基」と呼ぶことがある。）は、例えば、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、及び
無置換の環形成原子数５～５０の複素環基
からなる群から選択される基等であり、
ここで、Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の複素環基である。
Ｒ９０１が２個以上存在する場合、２個以上のＲ９０１は、互いに同一であるか、又は異なり、
Ｒ９０２が２個以上存在する場合、２個以上のＲ９０２は、互いに同一であるか、又は異なり、
Ｒ９０３が２個以上存在する場合、２個以上のＲ９０３は、互いに同一であるか、又は異なり、
Ｒ９０４が２個以上存在する場合、２個以上のＲ９０４は、互いに同一であるか、又は異なり、
Ｒ９０５が２個以上存在する場合、２個以上のＲ９０５は、互いに同一であるか、又は異なり、
Ｒ９０６が２個以上存在する場合、２個以上のＲ９０６は、互いに同一であるか、又は異なり、
Ｒ９０７が２個以上存在する場合、２個以上のＲ９０７は、互いに同一であるか又は異なる。 Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) are, for example,
an unsubstituted alkyl group having 1 to 50 carbon atoms;
an unsubstituted alkenyl group having 2 to 50 carbon atoms,
an unsubstituted alkynyl group having 2 to 50 carbon atoms,
an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring atoms,
In the formula, R 901 to R 907 each independently represent
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
When two or more R 901 are present, the two or more R 901 are the same or different from each other,
When two or more R 902 are present, the two or more R 902 are the same or different from each other,
When two or more R 903 are present, the two or more R 903 are the same or different from each other,
When two or more R 904 are present, the two or more R 904 are the same or different from each other,
When two or more R 905 are present, the two or more R 905 are the same or different from each other,
When two or more R 906 are present, the two or more R 906 are the same or different from each other,
When two or more R 907 are present, the two or more R 907 are the same or different.
一実施形態においては、前記「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the above "substituted or unsubstituted" is:
an alkyl group having 1 to 50 carbon atoms,
The group is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the above "substituted or unsubstituted" is:
an alkyl group having 1 to 50 carbon atoms,
The group is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
一実施形態においては、前記「置換もしくは無置換の」という場合の置換基は、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、及び
環形成原子数５～１８の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the above "substituted or unsubstituted" is:
an alkyl group having 1 to 18 carbon atoms,
The group is selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、及び
環形成原子数５～１８の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the above "substituted or unsubstituted" is:
an alkyl group having 1 to 18 carbon atoms,
The group is selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
上記任意の置換基の各基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基の具体例である。
Specific examples of each of the optional substituents are the specific examples of the substituents described in the above section "Substituents described in this specification."
本明細書において別途記載のない限り、隣接する任意の置換基同士で、「飽和の環」、又は「不飽和の環」を形成してもよく、好ましくは、置換もしくは無置換の飽和の５員環、置換もしくは無置換の飽和の６員環、置換もしくは無置換の不飽和の５員環、又は置換もしくは無置換の不飽和の６員環を形成し、より好ましくは、ベンゼン環を形成する。
本明細書において別途記載のない限り、任意の置換基は、さらに置換基を有してもよい。任意の置換基がさらに有する置換基としては、上記任意の置換基と同様である。 Unless otherwise specified in this specification, any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.
Unless otherwise specified in the present specification, the optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.
本明細書において別途記載のない限り、任意の置換基は、さらに置換基を有してもよい。任意の置換基がさらに有する置換基としては、上記任意の置換基と同様である。 Unless otherwise specified in this specification, any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.
Unless otherwise specified in the present specification, the optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.
本明細書において、「ＡＡ～ＢＢ」を用いて表される数値範囲は、「ＡＡ～ＢＢ」の前に記載される数値ＡＡを下限値とし、「ＡＡ～ＢＢ」の後に記載される数値ＢＢを上限値として含む範囲を意味する。
In this specification, a numerical range expressed using "AA-BB" refers to a range that includes the number AA written before "AA-BB" as the lower limit and the number BB written after "AA-BB" as the upper limit.
［新規な化合物］
本発明の一態様に係る化合物は、後述する式（１）又は式（２）で表される化合物である。 [New Compounds]
A compound according to one embodiment of the present invention is a compound represented by formula (1) or (2) described below.
本発明の一態様に係る化合物は、後述する式（１）又は式（２）で表される化合物である。 [New Compounds]
A compound according to one embodiment of the present invention is a compound represented by formula (1) or (2) described below.
本発明の一態様に係る化合物は、有機ＥＬ素子に用いた場合に、その素子性能を向上させることができる。特に、積層発光層のうちの１層の発光層に当該化合物を使用することにより、素子性能を向上させることができる。
When the compound according to one aspect of the present invention is used in an organic EL device, it can improve the device performance. In particular, by using the compound in one of the stacked light-emitting layers, it is possible to improve the device performance.
［式（１）で表される化合物］
本発明の一態様に係る化合物は、下記式（１）で表される。
［式（１）中、
Ｒ１０１～Ｒ１０５のうち１つは、下記式（Ａ１）で表される基と結合する単結合である。
（式（Ａ１）中、
ＬＡ１は、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のビフェニルジイル基、
置換もしくは無置換のターフェニルジイル基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のフェナントリルジイル基、
置換もしくは無置換のベンゾフェナントリルジイル基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のクリセンジイル基、
置換もしくは無置換のベンゾクリセンジイル基、
置換もしくは無置換のトリフェニレンジイル基、
置換もしくは無置換のベンゾトリフェニレンジイル基、
置換もしくは無置換のフルオレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、
置換もしくは無置換のジベンゾフルオレンジイル基、
置換もしくは無置換のナフトフルオレンジイル基、
置換もしくは無置換のフルオランテンジイル基、
置換もしくは無置換のベンゾフルオランテンジイル基、
置換もしくは無置換のペリレンジイル基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ１は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のビフェニル基、
置換もしくは無置換のターフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のフェナントリル基、
置換もしくは無置換のベンゾフェナントリル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のクリセニル基、
置換もしくは無置換のベンゾクリセニル基、
置換もしくは無置換のトリフェニレニル基、
置換もしくは無置換のベンゾトリフェニレニル基、
置換もしくは無置換のフルオレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトフルオレニル基、
置換もしくは無置換のフルオランテニル基、
置換もしくは無置換のベンゾフルオランテニル基、
置換もしくは無置換のペリレニル基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ１は０～３の整数である。
ｎＡ１が０である場合、（ＬＡ１）ｎＡ１は単結合である。
ｎＡ１が２又は３である場合、複数のＬＡ１は互いに直列状に連結し、ＡｒＡ１は、ジナフトフラン骨格から最も離れたＬＡ１に結合する。複数のＬＡ１は同一でもよく、異なってもよい。）
Ｒ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではないＲ１０１～Ｒ１０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではなく、互いに結合しないＲ１０１～Ｒ１０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ１）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。］ [Compound represented by formula (1)]
The compound according to one embodiment of the present invention is represented by the following formula (1).
[In formula (1),
One of R 101 to R 105 is a single bond bonded to a group represented by the following formula (A1).
(In formula (A1),
L A1 is,
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted biphenyldiyl group,
a substituted or unsubstituted terphenyldiyl group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted phenanthryldiyl group,
a substituted or unsubstituted benzophenanthryldiyl group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
a substituted or unsubstituted chrysenediyl group;
a substituted or unsubstituted benzochrysenediyl group,
a substituted or unsubstituted triphenylenediyl group,
a substituted or unsubstituted benzotriphenylenediyl group,
a substituted or unsubstituted fluorenediyl group;
a substituted or unsubstituted benzofluorenediyl group,
a substituted or unsubstituted dibenzofluorenediyl group,
a substituted or unsubstituted naphthofluorenediyl group,
a substituted or unsubstituted fluoranthene diyl group;
a substituted or unsubstituted benzofluoranthene diyl group;
It is a substituted or unsubstituted perylenediyl group, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted biphenyl group,
a substituted or unsubstituted terphenyl group;
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted benzophenanthryl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted chrysenyl group;
a substituted or unsubstituted benzochrysenyl group,
a substituted or unsubstituted triphenylenyl group,
a substituted or unsubstituted benzotriphenylenyl group,
a substituted or unsubstituted fluorenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
a substituted or unsubstituted naphthofluorenyl group,
a substituted or unsubstituted fluoranthenyl group;
a substituted or unsubstituted benzofluoranthenyl group;
It is a substituted or unsubstituted perylenyl group, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA1 is an integer of 0 to 3.
When nA1 is 0, (L A1 ) nA1 is a single bond.
When nA1 is 2 or 3, multiple L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the most distant from the dinaphthofuran skeleton. Multiple L A1 may be the same or different.
One or more pairs of adjacent two or more of R 106 to R 112 and R 101 to R 105 that are not a single bond bonded to the group represented by formula (A1) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R 106 to R 112 which are not bonded to each other, and R 101 to R 105 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A1) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A1).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, each of the two or more R 41 to R 45 and R 49 to R 51 may be the same or different.]
本発明の一態様に係る化合物は、下記式（１）で表される。
Ｒ１０１～Ｒ１０５のうち１つは、下記式（Ａ１）で表される基と結合する単結合である。
ＬＡ１は、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のビフェニルジイル基、
置換もしくは無置換のターフェニルジイル基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のフェナントリルジイル基、
置換もしくは無置換のベンゾフェナントリルジイル基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のクリセンジイル基、
置換もしくは無置換のベンゾクリセンジイル基、
置換もしくは無置換のトリフェニレンジイル基、
置換もしくは無置換のベンゾトリフェニレンジイル基、
置換もしくは無置換のフルオレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、
置換もしくは無置換のジベンゾフルオレンジイル基、
置換もしくは無置換のナフトフルオレンジイル基、
置換もしくは無置換のフルオランテンジイル基、
置換もしくは無置換のベンゾフルオランテンジイル基、
置換もしくは無置換のペリレンジイル基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ１は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のビフェニル基、
置換もしくは無置換のターフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のフェナントリル基、
置換もしくは無置換のベンゾフェナントリル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のクリセニル基、
置換もしくは無置換のベンゾクリセニル基、
置換もしくは無置換のトリフェニレニル基、
置換もしくは無置換のベンゾトリフェニレニル基、
置換もしくは無置換のフルオレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトフルオレニル基、
置換もしくは無置換のフルオランテニル基、
置換もしくは無置換のベンゾフルオランテニル基、
置換もしくは無置換のペリレニル基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ１は０～３の整数である。
ｎＡ１が０である場合、（ＬＡ１）ｎＡ１は単結合である。
ｎＡ１が２又は３である場合、複数のＬＡ１は互いに直列状に連結し、ＡｒＡ１は、ジナフトフラン骨格から最も離れたＬＡ１に結合する。複数のＬＡ１は同一でもよく、異なってもよい。）
Ｒ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではないＲ１０１～Ｒ１０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではなく、互いに結合しないＲ１０１～Ｒ１０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ１）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。］ [Compound represented by formula (1)]
The compound according to one embodiment of the present invention is represented by the following formula (1).
One of R 101 to R 105 is a single bond bonded to a group represented by the following formula (A1).
L A1 is,
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted biphenyldiyl group,
a substituted or unsubstituted terphenyldiyl group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted phenanthryldiyl group,
a substituted or unsubstituted benzophenanthryldiyl group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
a substituted or unsubstituted chrysenediyl group;
a substituted or unsubstituted benzochrysenediyl group,
a substituted or unsubstituted triphenylenediyl group,
a substituted or unsubstituted benzotriphenylenediyl group,
a substituted or unsubstituted fluorenediyl group;
a substituted or unsubstituted benzofluorenediyl group,
a substituted or unsubstituted dibenzofluorenediyl group,
a substituted or unsubstituted naphthofluorenediyl group,
a substituted or unsubstituted fluoranthene diyl group;
a substituted or unsubstituted benzofluoranthene diyl group;
It is a substituted or unsubstituted perylenediyl group, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted biphenyl group,
a substituted or unsubstituted terphenyl group;
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted benzophenanthryl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted chrysenyl group;
a substituted or unsubstituted benzochrysenyl group,
a substituted or unsubstituted triphenylenyl group,
a substituted or unsubstituted benzotriphenylenyl group,
a substituted or unsubstituted fluorenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
a substituted or unsubstituted naphthofluorenyl group,
a substituted or unsubstituted fluoranthenyl group;
a substituted or unsubstituted benzofluoranthenyl group;
It is a substituted or unsubstituted perylenyl group, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA1 is an integer of 0 to 3.
When nA1 is 0, (L A1 ) nA1 is a single bond.
When nA1 is 2 or 3, multiple L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the most distant from the dinaphthofuran skeleton. Multiple L A1 may be the same or different.
One or more pairs of adjacent two or more of R 106 to R 112 and R 101 to R 105 that are not a single bond bonded to the group represented by formula (A1) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R 106 to R 112 which are not bonded to each other, and R 101 to R 105 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A1) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A1).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, each of the two or more R 41 to R 45 and R 49 to R 51 may be the same or different.]
式（１）において、「ｎＡ１が２又は３である場合、複数のＬＡ１は互いに直列状に連結し、ＡｒＡ１は、ジナフトフラン骨格から最も離れたＬＡ１に結合する。」について説明する。
定義から自明であるが、ｎＡ１が２又は３である場合、複数のＬＡ１は、ジナフトフラン骨格とＡｒＡ１との間で直列状に連結し、分岐しない。 In formula (1), "when nA1 is 2 or 3, a plurality of L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the furthest from the dinaphthofuran skeleton." will be explained.
As is obvious from the definition, when nA1 is 2 or 3, a plurality of L A1 are linked in series between the dinaphthofuran skeleton and Ar A1 , and are not branched.
定義から自明であるが、ｎＡ１が２又は３である場合、複数のＬＡ１は、ジナフトフラン骨格とＡｒＡ１との間で直列状に連結し、分岐しない。 In formula (1), "when nA1 is 2 or 3, a plurality of L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the furthest from the dinaphthofuran skeleton." will be explained.
As is obvious from the definition, when nA1 is 2 or 3, a plurality of L A1 are linked in series between the dinaphthofuran skeleton and Ar A1 , and are not branched.
例えば、Ｒ１０５が、式（Ａ１）で表される基と結合する単結合であり、ｎＡ１が３である場合、式（１）で表される化合物は、下記式（Ｅ１）で表される構造となる。
For example, when R 105 is a single bond bonded to the group represented by formula (A1) and nA1 is 3, the compound represented by formula (1) has a structure represented by the following formula (E1).
式（１）において、式（Ａ１）のＬＡ１が単結合である場合、ＡｒＡ１は、ジナフトフラン骨格に直接結合する。
In formula (1), when L A1 in formula (A1) is a single bond, Ar A1 is directly bonded to the dinaphthofuran skeleton.
「前記式（Ａ１）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基」について説明する。
「前記式（Ａ１）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが異なる場合、化学構造式（骨格）が互いに異なる場合と、化学構造式（骨格）は同一であるが異なる同位体を含む場合と、を含む。同位体とは、原子番号が等しく、中性子数が異なる原子を意味する。例えば、ベンゼン（Ｃ６Ｈ６）と重水素化ベンゼン（Ｃ６Ｄ６）とは互いに異なる。
また、「前記式（Ａ１）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが、同一の骨格の置換基を有するが、当該置換基の置換位置がそれぞれ異なる場合、「前記式（Ａ１）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とは同一ではない。 The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not identical to the group represented by formula (A1)" will now be described.
This includes cases where the "group represented by formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are different, where their chemical structural formulas (skeletons) are different, and where the chemical structural formulas (skeletons) are the same but contain different isotopes. An isotope means an atom with the same atomic number but a different number of neutrons. For example, benzene (C 6 H 6 ) and deuterated benzene (C 6 D 6 ) are different from each other.
Furthermore, when the "group represented by the formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" have substituents in the same skeleton but the substitution positions of the substituents are different, the "group represented by the formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are not identical to each other.
「前記式（Ａ１）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが異なる場合、化学構造式（骨格）が互いに異なる場合と、化学構造式（骨格）は同一であるが異なる同位体を含む場合と、を含む。同位体とは、原子番号が等しく、中性子数が異なる原子を意味する。例えば、ベンゼン（Ｃ６Ｈ６）と重水素化ベンゼン（Ｃ６Ｄ６）とは互いに異なる。
また、「前記式（Ａ１）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが、同一の骨格の置換基を有するが、当該置換基の置換位置がそれぞれ異なる場合、「前記式（Ａ１）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とは同一ではない。 The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not identical to the group represented by formula (A1)" will now be described.
This includes cases where the "group represented by formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are different, where their chemical structural formulas (skeletons) are different, and where the chemical structural formulas (skeletons) are the same but contain different isotopes. An isotope means an atom with the same atomic number but a different number of neutrons. For example, benzene (C 6 H 6 ) and deuterated benzene (C 6 D 6 ) are different from each other.
Furthermore, when the "group represented by the formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" have substituents in the same skeleton but the substitution positions of the substituents are different, the "group represented by the formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are not identical to each other.
例えば、下記化合物は、「前記式（Ａ１）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とがいずれもフェナントレン－９－イル基であるため、式（１）には含まれない。
For example, the compound below is not included in formula (1) because both the “group represented by formula (A1)” and the “substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms” are phenanthren-9-yl groups.
一実施形態において、Ｒ１０２～Ｒ１０５のうち１つは、前記式（Ａ１）で表される基と結合する単結合である。
In one embodiment, one of R 102 to R 105 is a single bond bonding to the group represented by formula (A1).
一実施形態において、Ｒ１０２、Ｒ１０３、及びＲ１０５のうち１つは、前記式（Ａ１）で表される基と結合する単結合である。
一実施形態において、Ｒ１０３及びＲ１０５のうち１つは、前記式（Ａ１）で表される基と結合する単結合である。
一実施形態において、Ｒ１０２は、前記式（Ａ１）で表される基と結合する単結合である。
一実施形態において、Ｒ１０３は、前記式（Ａ１）で表される基と結合する単結合である。
一実施形態において、Ｒ１０５は、前記式（Ａ１）で表される基と結合する単結合である。 In one embodiment, one of R 102 , R 103 , and R 105 is a single bond bonding to the group represented by formula (A1).
In one embodiment, one of R 103 and R 105 is a single bond bonding to the group represented by formula (A1).
In one embodiment, R 102 is a single bond bonded to the group represented by formula (A1).
In one embodiment, R 103 is a single bond bonded to the group represented by formula (A1).
In one embodiment, R 105 is a single bond bonded to the group represented by formula (A1).
一実施形態において、Ｒ１０３及びＲ１０５のうち１つは、前記式（Ａ１）で表される基と結合する単結合である。
一実施形態において、Ｒ１０２は、前記式（Ａ１）で表される基と結合する単結合である。
一実施形態において、Ｒ１０３は、前記式（Ａ１）で表される基と結合する単結合である。
一実施形態において、Ｒ１０５は、前記式（Ａ１）で表される基と結合する単結合である。 In one embodiment, one of R 102 , R 103 , and R 105 is a single bond bonding to the group represented by formula (A1).
In one embodiment, one of R 103 and R 105 is a single bond bonding to the group represented by formula (A1).
In one embodiment, R 102 is a single bond bonded to the group represented by formula (A1).
In one embodiment, R 103 is a single bond bonded to the group represented by formula (A1).
In one embodiment, R 105 is a single bond bonded to the group represented by formula (A1).
一実施形態において、ＬＡ１は、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である。 In one embodiment, L A1 is
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である。 In one embodiment, L A1 is
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
一実施形態において、ＬＡ１は、
単結合、又は
置換もしくは無置換のフェニレン基である。 In one embodiment, L A1 is
It is a single bond, or a substituted or unsubstituted phenylene group.
単結合、又は
置換もしくは無置換のフェニレン基である。 In one embodiment, L A1 is
It is a single bond, or a substituted or unsubstituted phenylene group.
一実施形態において、ＡｒＡ１は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である。 In one embodiment, Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group; a substituted or unsubstituted pyrenyl group;
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である。 In one embodiment, Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group; a substituted or unsubstituted pyrenyl group;
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
一実施形態において、ＡｒＡ１は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、又は
置換もしくは無置換のジベンゾフルオレニル基である。 In one embodiment, Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group; a substituted or unsubstituted pyrenyl group;
It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、又は
置換もしくは無置換のジベンゾフルオレニル基である。 In one embodiment, Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group; a substituted or unsubstituted pyrenyl group;
It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
一実施形態において、前記式（Ａ１）で表される基は、下記式（Ａ１－１）～式（Ａ１－７）のいずれかで表される基である。
［式（Ａ１－１）～式（Ａ１－７）中、ｎＡ１及びＬＡ１は、前記式（Ａ１）で定義した通りである。
ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ In one embodiment, the group represented by formula (A1) is a group represented by any one of the following formulas (A1-1) to (A1-7).
[In formulas (A1-1) to (A1-7), nA1 and L A1 are as defined in formula (A1) above.
R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.]
ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ In one embodiment, the group represented by formula (A1) is a group represented by any one of the following formulas (A1-1) to (A1-7).
R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.]
一実施形態において、前記式（Ａ１）で表される基は、前記式（Ａ１－１）～式（Ａ１－５）のいずれかで表される基である。
In one embodiment, the group represented by formula (A1) is a group represented by any one of formulas (A1-1) to (A1-5).
一実施形態において、前記式（１）で表される化合物は、下記式（１－１）～式（１－３）のいずれかで表される化合物である。
［式（１－１）～式（１－３）中、ｎＡ１、ＬＡ１、ＡｒＡ１、Ｒ１０１～Ｒ１１２は、前記式（１）で定義した通りである。］
In one embodiment, the compound represented by formula (1) is a compound represented by any one of formulas (1-1) to (1-3) below.
[In the formulas (1-1) to (1-3), nA1, L A1 , Ar A1 , and R 101 to R 112 are as defined in the formula (1).]
一実施形態において、前記式（１）で表される化合物は、前記式（１－１）又は式（１－２）で表される化合物である。
In one embodiment, the compound represented by formula (1) is a compound represented by formula (1-1) or formula (1-2).
一実施形態において、前記式（１）で表される化合物は、下記式（１－１１）～式（１－１９）のいずれかで表される化合物である。
［式（１－１１）～式（１－１９）中、ｎＡ１、ＬＡ１、Ｒ１０１～Ｒ１１２は、前記式（１）で定義した通りである。
ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ In one embodiment, the compound represented by formula (1) is a compound represented by any one of formulas (1-11) to (1-19) below.
[In formulas (1-11) to (1-19), nA1, L A1 , and R 101 to R 112 are as defined in formula (1).
R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.]
ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ In one embodiment, the compound represented by formula (1) is a compound represented by any one of formulas (1-11) to (1-19) below.
R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.]
一実施形態において、前記式（１）で表される化合物は、前記式（１－１１）～式（１－１４）のいずれかで表される化合物である。
In one embodiment, the compound represented by formula (1) is a compound represented by any one of formulas (1-11) to (1-14).
一実施形態において、単結合ではないＲ１０１～Ｒ１１２は、水素原子である。
In one embodiment, R 101 to R 112 that are not single bonds are hydrogen atoms.
一実施形態において、ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９が、それぞれ独立に、
水素原子、
メチル基、
フェニル基、又は
ナフチル基である。 In one embodiment, R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently:
Hydrogen atoms,
Methyl group,
It is a phenyl group or a naphthyl group.
水素原子、
メチル基、
フェニル基、又は
ナフチル基である。 In one embodiment, R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently:
Hydrogen atoms,
Methyl group,
It is a phenyl group or a naphthyl group.
一実施形態において、ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９は、それぞれ独立に、水素原子、メチル基、又はフェニル基である。
In one embodiment, R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently a hydrogen atom, a methyl group, or a phenyl group.
一実施形態において、ＲＡ１１～ＲＡ１４及びＲＡ１６～ＲＡ１９は、水素原子であり、ＲＡ１５は、フェニル基である。
In one embodiment, R A11 to R A14 and R A16 to R A19 are hydrogen atoms, and R A15 is a phenyl group.
一実施形態において、ＲＡ１１～ＲＡ１９は、水素原子である。
In one embodiment, R A11 to R A19 are hydrogen atoms.
一実施形態において、ＲＡ２１～ＲＡ２６及びＲＡ２８～ＲＡ３２は、水素原子である。
In one embodiment, R A21 to R A26 and R A28 to R A32 are hydrogen atoms.
一実施形態において、ＲＡ２１～ＲＡ２６及びＲＡ２８～ＲＡ３１は、水素原子であり、ＲＡ２７は、フェニル基である。
In one embodiment, R A21 to R A26 and R A28 to R A31 are hydrogen atoms, and R A27 is a phenyl group.
一実施形態において、ＲＡ４１～ＲＡ４９及びＲＡ６１～ＲＡ７１は、水素原子であり、ＲＡ５０～ＲＡ５１及びＲＡ７２～ＲＡ７３は、メチル基である。
In one embodiment, R A41 to R A49 and R A61 to R A71 are hydrogen atoms, and R A50 to R A51 and R A72 to R A73 are methyl groups.
一実施形態において、ＲＡ８１～ＲＡ８９は、水素原子である。
In one embodiment, R A81 to R A89 are hydrogen atoms.
一実施形態において、ＲＡ９１～ＲＡ９９は、水素原子である。
In one embodiment, R A91 to R A99 are hydrogen atoms.
一実施形態において、水素原子であるＲＡ８１～ＲＡ８９のうち少なくとも１つは、重水素原子である。
In one embodiment, at least one of R A81 to R A89 which are hydrogen atoms is a deuterium atom.
一実施形態において、水素原子であるＲＡ９１～ＲＡ９９のうち少なくとも１つは、重水素原子である。
In one embodiment, at least one of R A91 to R A99 which are hydrogen atoms is a deuterium atom.
本明細書において、水素原子が「重水素原子である」とは、当該水素原子において、軽水素原子と重水素原子の合計に対して、重水素原子の割合が天然存在比より多いことを意味する。軽水素原子と重水素原子の合計に対して、重水素原子の割合が天然存在比より多いことは、核磁気共鳴装置により確認することができる。
In this specification, when a hydrogen atom is "a deuterium atom," it means that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms in the hydrogen atom is greater than the natural abundance ratio. The fact that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms is greater than the natural abundance ratio can be confirmed using a nuclear magnetic resonance spectrometer.
一実施形態において、式（１）における「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の１価の複素環基
からなる群から選択される基である、 In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) is
an alkyl group having 1 to 50 carbon atoms,
a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms;
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の１価の複素環基
からなる群から選択される基である、 In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) is
an alkyl group having 1 to 50 carbon atoms,
a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms;
一実施形態において、式（１）における「置換もしくは無置換の」という場合の置換基は、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、及び
環形成原子数５～１８の１価の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) is
an alkyl group having 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、及び
環形成原子数５～１８の１価の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) is
an alkyl group having 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
式（１）で表される化合物は、実施例に倣い、目的物に合わせた既知の代替反応や原料を用いることで合成することができる。
The compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions and raw materials that are suited to the target product.
以下に、式（１）で表される化合物の具体例を記載するが、これらは例示に過ぎず、式（１）で表される化合物は下記具体例に限定されるものではない。
Specific examples of compounds represented by formula (1) are listed below, but these are merely examples, and compounds represented by formula (1) are not limited to the specific examples below.
［式（２）で表される化合物］
本発明の一態様に係る化合物は、下記式（２）で表される。
［式（２）中、
Ｒ２０１～Ｒ２０５のうち１つは、下記式（Ａ２）で表される基と結合する単結合である。
（式（Ａ２）中、
ＬＡ２は、
単結合、
置換もしくは無置換の環形成炭素数６～２１のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ２は、
５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ２は０～３の整数である。
ｎＡ２が０である場合、（ＬＡ２）ｎＡ２は単結合である。
ｎＡ２が２又は３である場合、複数のＬＡ２は互いに直列状に連結し、ＡｒＡ２は、ジナフトフラン骨格から最も離れたＬＡ２に結合する。複数のＬＡ２は同一でもよく、異なってもよい。）
Ｒ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではないＲ２０１～Ｒ２０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではなく、互いに結合しないＲ２０１～Ｒ２０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ２）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。
ただし、ＬＡ２における、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、及び置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基、並びにＡｒＡ２における、５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、及び置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基は、それぞれ下記式（Ｔ１）を満たす基である。
Ｔ１＞１．８１ｅＶ・・・（Ｔ１）
（式（Ｔ１）中、Ｔ１は、当該基の三重項エネルギーである。）］ [Compound represented by formula (2)]
The compound according to one embodiment of the present invention is represented by the following formula (2).
[In formula (2),
One of R 201 to R 205 is a single bond bonded to a group represented by the following formula (A2).
(In formula (A2),
L A2 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A2 is
It is a substituted or unsubstituted aryl group consisting of 5 or less rings and having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA2 is an integer from 0 to 3.
When nA2 is 0, (L A2 ) nA2 is a single bond.
When nA2 is 2 or 3, multiple L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the most distant from the dinaphthofuran skeleton. Multiple L A2 may be the same or different.
Among R 206 to R 212 and R 201 to R 205 that are not single bonds bonded to the group represented by formula (A2), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 206 to R 212 which are not bonded to each other, and R 201 to R 205 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A2) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A2).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, each of the two or more R 41 to R 45 and R 49 to R 51 may be the same or different.
However, the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms which are composed of 5 or less rings in Ar A2 are each a group which satisfies the following formula (T1).
T 1 >1.81eV...(T1)
(In formula (T1), T1 is the triplet energy of the group.)
本発明の一態様に係る化合物は、下記式（２）で表される。
Ｒ２０１～Ｒ２０５のうち１つは、下記式（Ａ２）で表される基と結合する単結合である。
ＬＡ２は、
単結合、
置換もしくは無置換の環形成炭素数６～２１のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ２は、
５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ２は０～３の整数である。
ｎＡ２が０である場合、（ＬＡ２）ｎＡ２は単結合である。
ｎＡ２が２又は３である場合、複数のＬＡ２は互いに直列状に連結し、ＡｒＡ２は、ジナフトフラン骨格から最も離れたＬＡ２に結合する。複数のＬＡ２は同一でもよく、異なってもよい。）
Ｒ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではないＲ２０１～Ｒ２０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではなく、互いに結合しないＲ２０１～Ｒ２０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ２）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。
ただし、ＬＡ２における、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、及び置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基、並びにＡｒＡ２における、５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、及び置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基は、それぞれ下記式（Ｔ１）を満たす基である。
Ｔ１＞１．８１ｅＶ・・・（Ｔ１）
（式（Ｔ１）中、Ｔ１は、当該基の三重項エネルギーである。）］ [Compound represented by formula (2)]
The compound according to one embodiment of the present invention is represented by the following formula (2).
One of R 201 to R 205 is a single bond bonded to a group represented by the following formula (A2).
L A2 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A2 is
It is a substituted or unsubstituted aryl group consisting of 5 or less rings and having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA2 is an integer from 0 to 3.
When nA2 is 0, (L A2 ) nA2 is a single bond.
When nA2 is 2 or 3, multiple L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the most distant from the dinaphthofuran skeleton. Multiple L A2 may be the same or different.
Among R 206 to R 212 and R 201 to R 205 that are not single bonds bonded to the group represented by formula (A2), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 206 to R 212 which are not bonded to each other, and R 201 to R 205 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A2) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A2).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, each of the two or more R 41 to R 45 and R 49 to R 51 may be the same or different.
However, the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms which are composed of 5 or less rings in Ar A2 are each a group which satisfies the following formula (T1).
T 1 >1.81eV...(T1)
(In formula (T1), T1 is the triplet energy of the group.)
式（２）において、「ｎＡ２が２又は３である場合、複数のＬＡ２は互いに直列状に連結し、ＡｒＡ２は、ジナフトフラン骨格から最も離れたＬＡ２に結合する。」について説明する。
定義から自明であるが、ｎＡ２が２又は３である場合、複数のＬＡ２は、ジナフトフラン骨格とＡｒＡ２との間で直列状に連結し、分岐しない。 In formula (2), "when nA2 is 2 or 3, a plurality of L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the furthest from the dinaphthofuran skeleton." will be explained.
As is obvious from the definition, when nA2 is 2 or 3, a plurality of L A2 are linked in series between the dinaphthofuran skeleton and Ar A2 , and are not branched.
定義から自明であるが、ｎＡ２が２又は３である場合、複数のＬＡ２は、ジナフトフラン骨格とＡｒＡ２との間で直列状に連結し、分岐しない。 In formula (2), "when nA2 is 2 or 3, a plurality of L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the furthest from the dinaphthofuran skeleton." will be explained.
As is obvious from the definition, when nA2 is 2 or 3, a plurality of L A2 are linked in series between the dinaphthofuran skeleton and Ar A2 , and are not branched.
例えば、Ｒ２０５が、式（Ａ２）で表される基と結合する単結合であり、ｎＡ２が３である場合、式（２）で表される化合物は、下記式（Ｅ２）で表される構造となる。
For example, when R 205 is a single bond bonded to the group represented by formula (A2) and nA2 is 3, the compound represented by formula (2) has a structure represented by the following formula (E2).
式（２）において、式（Ａ２）のＬＡ２が単結合である場合、ＡｒＡ２は、ジナフトフラン骨格に直接結合する。
In formula (2), when L A2 in formula (A2) is a single bond, Ar A2 is directly bonded to the dinaphthofuran skeleton.
「前記式（Ａ２）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基」について説明する。
「前記式（Ａ２）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが異なる場合、化学構造式（骨格）が互いに異なる場合と、化学構造式（骨格）は同一であるが異なる同位体を含む場合と、を含む。同位体とは、原子番号が等しく、中性子数が異なる原子を意味する。例えば、ベンゼン（Ｃ６Ｈ６）と重水素化ベンゼン（Ｃ６Ｄ６）とは互いに異なる。
また、「前記式（Ａ２）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが、同一の骨格の置換基を有するが、当該置換基の置換位置がそれぞれ異なる場合、「前記式（Ａ２）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とは同一ではない。 The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not identical to the group represented by formula (A2)" will be explained below.
This includes cases where the "group represented by formula (A2)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are different, where their chemical structural formulas (skeletons) are different, and where the chemical structural formulas (skeletons) are the same but contain different isotopes. An isotope means an atom with the same atomic number but a different number of neutrons. For example, benzene (C 6 H 6 ) and deuterated benzene (C 6 D 6 ) are different from each other.
Furthermore, when the "group represented by the formula (A2)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" have substituents in the same skeleton but the substitution positions of the substituents are different, the "group represented by the formula (A2)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are not identical to each other.
「前記式（Ａ２）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが異なる場合、化学構造式（骨格）が互いに異なる場合と、化学構造式（骨格）は同一であるが異なる同位体を含む場合と、を含む。同位体とは、原子番号が等しく、中性子数が異なる原子を意味する。例えば、ベンゼン（Ｃ６Ｈ６）と重水素化ベンゼン（Ｃ６Ｄ６）とは互いに異なる。
また、「前記式（Ａ２）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが、同一の骨格の置換基を有するが、当該置換基の置換位置がそれぞれ異なる場合、「前記式（Ａ２）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とは同一ではない。 The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not identical to the group represented by formula (A2)" will be explained below.
This includes cases where the "group represented by formula (A2)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are different, where their chemical structural formulas (skeletons) are different, and where the chemical structural formulas (skeletons) are the same but contain different isotopes. An isotope means an atom with the same atomic number but a different number of neutrons. For example, benzene (C 6 H 6 ) and deuterated benzene (C 6 D 6 ) are different from each other.
Furthermore, when the "group represented by the formula (A2)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" have substituents in the same skeleton but the substitution positions of the substituents are different, the "group represented by the formula (A2)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are not identical to each other.
例えば、下記化合物は、「前記式（Ａ２）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とがいずれもフェナントレン－９－イル基であるため、式（２）には含まれない。
For example, the compound below is not included in formula (2) because both the "group represented by formula (A2)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are phenanthren-9-yl groups.
式（２）において、「５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基」について説明する。
In formula (2), we will explain the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and consisting of 5 or less rings."
「１個の環で構成される」とは、単環であることを意味する。
例えば、フェニル基は、１個の環で構成される。 "Consisting of one ring" means that it is a monocyclic ring.
For example, a phenyl group consists of one ring.
例えば、フェニル基は、１個の環で構成される。 "Consisting of one ring" means that it is a monocyclic ring.
For example, a phenyl group consists of one ring.
「Ｘ個の環で構成される（Ｘは２以上の整数）」とは、Ｘ個の環が、縮合又はスピロ結合した多環であることを意味する。
なお、「置換もしくは無置換の」という場合の置換基同士が互いに結合して環を形成し、当該置換基を有する環と縮合するか、あるいはスピロ結合する場合、置換基同士が互いに結合して形成した環も「Ｘ個の環」に含む。 The phrase "composed of X rings (X is an integer of 2 or more)" means that the X rings are condensed or spiro-bonded polycyclic rings.
In the case of "substituted or unsubstituted", when substituents are bonded to each other to form a ring and are condensed or spiro-bonded to a ring having the substituent, the ring formed by bonding the substituents to each other is also included in "X rings".
なお、「置換もしくは無置換の」という場合の置換基同士が互いに結合して環を形成し、当該置換基を有する環と縮合するか、あるいはスピロ結合する場合、置換基同士が互いに結合して形成した環も「Ｘ個の環」に含む。 The phrase "composed of X rings (X is an integer of 2 or more)" means that the X rings are condensed or spiro-bonded polycyclic rings.
In the case of "substituted or unsubstituted", when substituents are bonded to each other to form a ring and are condensed or spiro-bonded to a ring having the substituent, the ring formed by bonding the substituents to each other is also included in "X rings".
例えば、以下のナフチル基は、２つの環で構成される。当該ナフチル基は、置換基を有してもよい。
For example, the following naphthyl group is composed of two rings: The naphthyl group may have a substituent.
例えば、以下のベンゾフルオレニル基は、４つの環で構成される。当該ベンゾフルオレニル基は、置換基を有してもよい。
For example, the following benzofluorenyl group is composed of four rings: The benzofluorenyl group may have a substituent.
例えば、以下のスピロビフルオレニル基は、６つの環で構成される。
For example, the following spirobifluorenyl group is made up of six rings:
すなわち、「５個以下の環で構成される」とは、単環であるか、あるいは２つ、３つ、４つ、又は５つの環が、縮合又はスピロ結合した多環であることを意味する。
In other words, "composed of five or fewer rings" means that it is a monocyclic ring, or a polycyclic ring in which two, three, four, or five rings are fused or spiro-linked.
式（２）において、「ＬＡ２における、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、及び置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基、並びにＡｒＡ２における、５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、及び置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基は、それぞれ下記式（Ｔ１）を満たす基である。」について説明する。
Regarding formula (2), "the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and being composed of 5 or less rings, and the substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in Ar A2 are each groups that satisfy the following formula (T1)." will be explained.
Ｔ１＞１．８１ｅＶ・・・（Ｔ１）
（式（Ｔ１）中、Ｔ１は、当該基の三重項エネルギーである。） T 1 >1.81eV...(T1)
(In formula (T1), T1 is the triplet energy of the group.)
（式（Ｔ１）中、Ｔ１は、当該基の三重項エネルギーである。） T 1 >1.81eV...(T1)
(In formula (T1), T1 is the triplet energy of the group.)
式（２）において、ＬＡ２が、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、又は置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である場合、当該基は、上記式（Ｔ１）を満たす。
換言すれば、単結合ではないＬＡ２は、上記式（Ｔ１）を満たす。 In formula (2), when L A2 is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, the group satisfies the above formula (T1).
In other words, L A2 that is not a single bond satisfies the above formula (T1).
換言すれば、単結合ではないＬＡ２は、上記式（Ｔ１）を満たす。 In formula (2), when L A2 is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, the group satisfies the above formula (T1).
In other words, L A2 that is not a single bond satisfies the above formula (T1).
置換もしくは無置換の環形成炭素数６～２１のアリーレン基、又は置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基であるＬＡ２が複数存在する場合、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、又は置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基であるＬＡ２は、それぞれ上記式（Ｔ１）を満たす。
換言すれば、単結合ではないＬＡ２が複数存在する場合、単結合ではないＬＡ２は、それぞれ上記式（Ｔ１）を満たす。 When a plurality of L A2 which are substituted or unsubstituted arylene groups having 6 to 21 ring carbon atoms or substituted or unsubstituted divalent oxygen-containing heterocyclic groups having 5 to 30 ring atoms are present, each of the L A2 which are substituted or unsubstituted arylene groups having 6 to 21 ring carbon atoms or substituted or unsubstituted divalent oxygen-containing heterocyclic groups having 5 to 30 ring atoms satisfies the above formula (T1).
In other words, when a plurality of L A2 which is not a single bond is present, each of the L A2 which is not a single bond satisfies the above formula (T1).
換言すれば、単結合ではないＬＡ２が複数存在する場合、単結合ではないＬＡ２は、それぞれ上記式（Ｔ１）を満たす。 When a plurality of L A2 which are substituted or unsubstituted arylene groups having 6 to 21 ring carbon atoms or substituted or unsubstituted divalent oxygen-containing heterocyclic groups having 5 to 30 ring atoms are present, each of the L A2 which are substituted or unsubstituted arylene groups having 6 to 21 ring carbon atoms or substituted or unsubstituted divalent oxygen-containing heterocyclic groups having 5 to 30 ring atoms satisfies the above formula (T1).
In other words, when a plurality of L A2 which is not a single bond is present, each of the L A2 which is not a single bond satisfies the above formula (T1).
式（２）において、ＡｒＡ２は、上記式（Ｔ１）を満たす。
In formula (2), Ar A2 satisfies the above formula (T1).
一実施形態において、ＬＡ２における、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、及び置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基、並びにＡｒＡ２における、５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、及び置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基は、それぞれ下記式（Ｔ２）を満たす基であるか、それぞれ下記式（Ｔ３）を満たす基であるか、それぞれ下記式（Ｔ４）を満たす基であるか、あるいはそれぞれ下記式（Ｔ５）を満たす基である。
Ｔ１＞１．８２ｅＶ・・・（Ｔ２）
Ｔ１＞１．８３ｅＶ・・・（Ｔ３）
Ｔ１＞１．８４ｅＶ・・・（Ｔ４）
Ｔ１＞１．８５ｅＶ・・・（Ｔ５）
（式中、Ｔ１は、当該基の三重項エネルギーである。） In one embodiment, the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms constituted by 5 or less rings in Ar A2 are each a group satisfying the following formula (T2), each a group satisfying the following formula (T3), each a group satisfying the following formula (T4), or each a group satisfying the following formula (T5).
T 1 >1.82eV...(T2)
T 1 >1.83eV...(T3)
T 1 >1.84eV...(T4)
T 1 >1.85eV...(T5)
(wherein T1 is the triplet energy of the group.)
Ｔ１＞１．８２ｅＶ・・・（Ｔ２）
Ｔ１＞１．８３ｅＶ・・・（Ｔ３）
Ｔ１＞１．８４ｅＶ・・・（Ｔ４）
Ｔ１＞１．８５ｅＶ・・・（Ｔ５）
（式中、Ｔ１は、当該基の三重項エネルギーである。） In one embodiment, the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms constituted by 5 or less rings in Ar A2 are each a group satisfying the following formula (T2), each a group satisfying the following formula (T3), each a group satisfying the following formula (T4), or each a group satisfying the following formula (T5).
T 1 >1.82eV...(T2)
T 1 >1.83eV...(T3)
T 1 >1.84eV...(T4)
T 1 >1.85eV...(T5)
(wherein T1 is the triplet energy of the group.)
Ｔ１の上限値は特に限定されないが、例えば、２．２０ｅＶ、２．６０ｅＶ、３．００ｅＶ、あるいは３．４０ｅＶである。
The upper limit of T1 is not particularly limited, and is, for example, 2.20 eV, 2.60 eV, 3.00 eV, or 3.40 eV.
式（Ｔ１）～（Ｔ５）におけるＴ１は、実施例に記載の方法で計算する。
T1 in the formulas (T1) to (T5) is calculated by the method described in the Examples.
一実施形態において、Ｒ２０２～Ｒ２０５のうち１つは、前記式（Ａ２）で表される基と結合する単結合である。
In one embodiment, one of R 202 to R 205 is a single bond bonding to the group represented by formula (A2).
一実施形態において、Ｒ２０２、Ｒ２０３、及びＲ２０５のうち１つは、前記式（Ａ２）で表される基と結合する単結合である。
In one embodiment, one of R 202 , R 203 , and R 205 is a single bond bonding to the group represented by formula (A2).
一実施形態において、Ｒ２０３及びＲ２０５のうち１つは、前記式（Ａ２）で表される基と結合する単結合である。
In one embodiment, one of R 203 and R 205 is a single bond bonding to the group represented by formula (A2).
一実施形態において、ＬＡ２は、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である。 In one embodiment, L A2 is
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である。 In one embodiment, L A2 is
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
一実施形態において、ＬＡ２は、
単結合、又は
置換もしくは無置換のフェニレン基である。 In one embodiment, L A2 is
It is a single bond, or a substituted or unsubstituted phenylene group.
単結合、又は
置換もしくは無置換のフェニレン基である。 In one embodiment, L A2 is
It is a single bond, or a substituted or unsubstituted phenylene group.
一実施形態において、ＡｒＡ２は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である。 In one embodiment, Ar A2 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である。 In one embodiment, Ar A2 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
一実施形態において、ＡｒＡ２は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、又は
置換もしくは無置換のジベンゾフルオレニル基である。 In one embodiment, Ar A2 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、又は
置換もしくは無置換のジベンゾフルオレニル基である。 In one embodiment, Ar A2 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
一実施形態において、前記式（Ａ２）で表される基は、下記式（Ａ２－１）～式（Ａ２－７）のいずれかで表される基である。
［式（Ａ２－１）～式（Ａ２－７）中、ｎＡ２及びＬＡ２は、前記式（Ａ２）で定義した通りである。
ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ In one embodiment, the group represented by formula (A2) is a group represented by any one of the following formulas (A2-1) to (A2-7).
[In formulas (A2-1) to (A2-7), nA2 and L A2 are as defined in formula (A2) above.
R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.]
ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ In one embodiment, the group represented by formula (A2) is a group represented by any one of the following formulas (A2-1) to (A2-7).
R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.]
一実施形態において、前記式（２）で表される化合物は、下記式（２－１）～式（２－３）のいずれかで表される化合物である。
［式（２－１）～式（２－３）中、ｎＡ２、ＬＡ２、ＡｒＡ２、Ｒ２０１～Ｒ２１２は、前記式（２）で定義した通りである。］
In one embodiment, the compound represented by formula (2) is a compound represented by any one of formulas (2-1) to (2-3) below.
[In the formulas (2-1) to (2-3), nA2, L A2 , Ar A2 , and R 201 to R 212 are as defined in the formula (2).]
一実施形態において、前記式（２）で表される化合物は、前記式（２－１）又は式（２－２）で表される化合物である。
In one embodiment, the compound represented by formula (2) is a compound represented by formula (2-1) or formula (2-2).
一実施形態において、前記式（２）で表される化合物は、下記式（２－１１）～式（２－１９）のいずれかで表される化合物である。
［式（２－１１）～式（２－１９）中、ｎＡ２、ＬＡ２、Ｒ２０１～Ｒ２１２は、前記式（２）で定義した通りである。
ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ In one embodiment, the compound represented by formula (2) is a compound represented by any one of the following formulas (2-11) to (2-19).
[In formulas (2-11) to (2-19), nA2, L A2 and R 201 to R 212 are as defined in formula (2) above.
R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.]
ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ In one embodiment, the compound represented by formula (2) is a compound represented by any one of the following formulas (2-11) to (2-19).
R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.]
一実施形態において、前記式（２）で表される化合物は、前記式（２－１１）～式（２－１４）のいずれかで表される化合物である。
In one embodiment, the compound represented by formula (2) is a compound represented by any one of formulas (2-11) to (2-14).
一実施形態において、単結合ではないＲ２０１～Ｒ２１２は、水素原子である。
In one embodiment, R 201 to R 212 that are not single bonds are hydrogen atoms.
一実施形態において、ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９は、それぞれ独立に、
水素原子、
メチル基、
フェニル基、又は
ナフチル基である。 In one embodiment, R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
Methyl group,
It is a phenyl group or a naphthyl group.
水素原子、
メチル基、
フェニル基、又は
ナフチル基である。 In one embodiment, R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
Methyl group,
It is a phenyl group or a naphthyl group.
一実施形態において、ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９は、それぞれ独立に、水素原子、メチル基、又はフェニル基である。
In one embodiment, R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently a hydrogen atom, a methyl group, or a phenyl group.
一実施形態において、ＲＡ１１１～ＲＡ１１４及びＲＡ１１６～ＲＡ１１９は、水素原子であり、ＲＡ１１５は、フェニル基である。
In one embodiment, R A111 to R A114 and R A116 to R A119 are hydrogen atoms, and R A115 is a phenyl group.
一実施形態において、ＲＡ１１１～ＲＡ１１９は、水素原子である。
In one embodiment, R A111 to R A119 are hydrogen atoms.
一実施形態において、ＲＡ１２１～ＲＡ１２６及びＲＡ１２８～ＲＡ１３２は、水素原子である。
In one embodiment, R A121 to R A126 and R A128 to R A132 are hydrogen atoms.
一実施形態において、ＲＡ１２１～ＲＡ１２６及びＲＡ１２８～ＲＡ１３１は、水素原子であり、ＲＡ１２７は、フェニル基である。
In one embodiment, R A121 to R A126 and R A128 to R A131 are hydrogen atoms, and R A127 is a phenyl group.
一実施形態において、ＲＡ１４１～ＲＡ１４９及びＲＡ１６１～ＲＡ１７１は、水素原子であり、ＲＡ１５０～ＲＡ１５１及びＲＡ１７２～ＲＡ１７３は、メチル基である。
In one embodiment, R A141 to R A149 and R A161 to R A171 are hydrogen atoms, and R A150 to R A151 and R A172 to R A173 are methyl groups.
一実施形態において、ＲＡ１８１～ＲＡ１８９は、水素原子である。
In one embodiment, R A181 to R A189 are hydrogen atoms.
一実施形態において、ＲＡ１９１～ＲＡ１９９は、水素原子である。
In one embodiment, R A191 to R A199 are hydrogen atoms.
一実施形態において、水素原子であるＲＡ１８１～ＲＡ１８９のうち少なくとも１つは、重水素原子である。
In one embodiment, at least one of R A181 to R A189 which are hydrogen atoms is a deuterium atom.
一実施形態において、水素原子であるＲＡ１９１～ＲＡ１９９のうち少なくとも１つは、重水素原子である。
In one embodiment, at least one of R A191 to R A199 which are hydrogen atoms is a deuterium atom.
本明細書において、水素原子が「重水素原子である」とは、当該水素原子において、軽水素原子と重水素原子の合計に対して、重水素原子の割合が天然存在比より多いことを意味する。軽水素原子と重水素原子の合計に対して、重水素原子の割合が天然存在比より多いことは、核磁気共鳴装置により確認することができる。
In this specification, when a hydrogen atom is "a deuterium atom," it means that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms in the hydrogen atom is greater than the natural abundance ratio. The fact that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms is greater than the natural abundance ratio can be confirmed using a nuclear magnetic resonance spectrometer.
一実施形態において、式（２）における「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
環形成炭素数６～１３のアリール基、及び
環形成原子数５～５０の１価の複素環基
からなる群から選択される基である、 In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (2) is
an alkyl group having 1 to 50 carbon atoms,
a group selected from the group consisting of an aryl group having 6 to 13 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms;
炭素数１～５０のアルキル基、
環形成炭素数６～１３のアリール基、及び
環形成原子数５～５０の１価の複素環基
からなる群から選択される基である、 In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (2) is
an alkyl group having 1 to 50 carbon atoms,
a group selected from the group consisting of an aryl group having 6 to 13 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms;
一実施形態において、式（２）における「置換もしくは無置換の」という場合の置換基は、
炭素数１～１８のアルキル基、
環形成炭素数６～１３のアリール基、及び
環形成原子数５～１８の１価の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (2) is
an alkyl group having 1 to 18 carbon atoms,
The group is selected from the group consisting of an aryl group having 6 to 13 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
炭素数１～１８のアルキル基、
環形成炭素数６～１３のアリール基、及び
環形成原子数５～１８の１価の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (2) is
an alkyl group having 1 to 18 carbon atoms,
The group is selected from the group consisting of an aryl group having 6 to 13 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
式（２）で表される化合物は、実施例に倣い、目的物に合わせた既知の代替反応や原料を用いることで合成することができる。
The compound represented by formula (2) can be synthesized by following the examples and using known alternative reactions and raw materials that are appropriate for the target product.
式（２）で表される化合物の具体例としては、上述した式（１）で表される化合物の具体例のほか、以下の化合物が挙げられる。これらは例示に過ぎず、式（２）で表される化合物は下記具体例に限定されるものではない。
Specific examples of compounds represented by formula (2) include the following compounds in addition to the specific examples of compounds represented by formula (1) described above. These are merely examples, and compounds represented by formula (2) are not limited to the specific examples below.
［有機エレクトロルミネッセンス素子用材料］
本発明の一態様に係る化合物は、有機ＥＬ素子用材料として有用であり、例えば、有機ＥＬ素子の発光層に用いる材料として有用である。 [Materials for organic electroluminescence devices]
The compound according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material used in the light-emitting layer of an organic EL device.
本発明の一態様に係る化合物は、有機ＥＬ素子用材料として有用であり、例えば、有機ＥＬ素子の発光層に用いる材料として有用である。 [Materials for organic electroluminescence devices]
The compound according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material used in the light-emitting layer of an organic EL device.
［有機ＥＬ素子］
本発明の一態様に係る有機ＥＬ素子について説明する。
本発明の一態様に係る有機ＥＬ素子は、陰極と、陽極と、前記陰極及び前記陽極の間に配置された発光層と、を有し、前記発光層は第１の発光層及び第２の発光層を含み、前記第１の発光層は、後述する式（３）で表される化合物を含む。 [Organic EL element]
An organic EL element according to one embodiment of the present invention will be described.
An organic EL element according to one aspect of the present invention includes a cathode, an anode, and an emitting layer disposed between the cathode and the anode, the emitting layer including a first emitting layer and a second emitting layer, and the first emitting layer includes a compound represented by formula (3) described below.
本発明の一態様に係る有機ＥＬ素子について説明する。
本発明の一態様に係る有機ＥＬ素子は、陰極と、陽極と、前記陰極及び前記陽極の間に配置された発光層と、を有し、前記発光層は第１の発光層及び第２の発光層を含み、前記第１の発光層は、後述する式（３）で表される化合物を含む。 [Organic EL element]
An organic EL element according to one embodiment of the present invention will be described.
An organic EL element according to one aspect of the present invention includes a cathode, an anode, and an emitting layer disposed between the cathode and the anode, the emitting layer including a first emitting layer and a second emitting layer, and the first emitting layer includes a compound represented by formula (3) described below.
本発明の一態様に係る有機ＥＬ素子は、上記構成を有することにより、性能を向上させることができる。
The organic EL element according to one aspect of the present invention has the above-mentioned configuration, which allows for improved performance.
本発明の一態様の有機ＥＬ素子の概略構成を、図１を参照して説明する。
本発明の一態様に係る有機ＥＬ素子１は、基板２と、陽極３と、発光層５と、陰極１０と、陽極３と発光層５との間にある正孔輸送帯域４と、発光層５と陰極１０との間にある電子輸送帯域６とを有する。
発光層５は積層構造を有し、少なくとも第１の発光層と、第２の発光層と、を含む。 The schematic configuration of an organic EL element according to one embodiment of the present invention will be described with reference to FIG.
Anorganic EL element 1 according to one embodiment of the present invention includes a substrate 2, an anode 3, an emitting layer 5, a cathode 10, a hole transporting region 4 between the anode 3 and the emitting layer 5, and an electron transporting region 6 between the emitting layer 5 and the cathode 10.
The light-emittinglayer 5 has a laminated structure and includes at least a first light-emitting layer and a second light-emitting layer.
本発明の一態様に係る有機ＥＬ素子１は、基板２と、陽極３と、発光層５と、陰極１０と、陽極３と発光層５との間にある正孔輸送帯域４と、発光層５と陰極１０との間にある電子輸送帯域６とを有する。
発光層５は積層構造を有し、少なくとも第１の発光層と、第２の発光層と、を含む。 The schematic configuration of an organic EL element according to one embodiment of the present invention will be described with reference to FIG.
An
The light-emitting
本発明の有機ＥＬ素子の代表的な素子構成としては、
（１）陽極／発光層／陰極
（２）陽極／正孔注入層／発光層／陰極
（３）陽極／発光層／電子注入・輸送層／陰極
（４）陽極／正孔注入層／発光層／電子注入・輸送層／陰極
（５）陽極／有機半導体層／発光層／陰極
（６）陽極／有機半導体層／電子障壁層／発光層／陰極
（７）陽極／有機半導体層／発光層／付着改善層／陰極
（８）陽極／正孔注入・輸送層／発光層／電子注入・輸送層／陰極
（９）陽極／絶縁層／発光層／絶縁層／陰極
（１０）陽極／無機半導体層／絶縁層／発光層／絶縁層／陰極
（１１）陽極／有機半導体層／絶縁層／発光層／絶縁層／陰極
（１２）陽極／絶縁層／正孔注入・輸送層／発光層／絶縁層／陰極
（１３）陽極／絶縁層／正孔注入・輸送層／発光層／電子注入・輸送層／陰極
等の構造を挙げることができる。
上記の中で（８）の構成が好ましく用いられるが、これらに限定されるものではない。 Representative element configurations of the organic EL element of the present invention include:
(1) anode/light-emitting layer/cathode (2) anode/hole-injection layer/light-emitting layer/cathode (3) anode/light-emitting layer/electron-injection and transport layer/cathode (4) anode/hole-injection layer/light-emitting layer/electron-injection and transport layer/cathode (5) anode/organic semiconductor layer/light-emitting layer/cathode (6) anode/organic semiconductor layer/electron-blocking layer/light-emitting layer/cathode (7) anode/organic semiconductor layer/light-emitting layer/adhesion-improving layer/cathode (8) anode/hole-injection and transport layer/light-emitting layer/ Examples of structures include electron injection/transport layer/cathode (9) anode/insulating layer/light-emitting layer/insulating layer/cathode (10) anode/inorganic semiconductor layer/insulating layer/light-emitting layer/insulating layer/cathode (11) anode/organic semiconductor layer/insulating layer/light-emitting layer/insulating layer/cathode (12) anode/insulating layer/hole injection/transport layer/light-emitting layer/insulating layer/cathode (13) anode/insulating layer/hole injection/transport layer/light-emitting layer/electron injection/transport layer/cathode.
Among the above, the configuration (8) is preferably used, but the present invention is not limited thereto.
（１）陽極／発光層／陰極
（２）陽極／正孔注入層／発光層／陰極
（３）陽極／発光層／電子注入・輸送層／陰極
（４）陽極／正孔注入層／発光層／電子注入・輸送層／陰極
（５）陽極／有機半導体層／発光層／陰極
（６）陽極／有機半導体層／電子障壁層／発光層／陰極
（７）陽極／有機半導体層／発光層／付着改善層／陰極
（８）陽極／正孔注入・輸送層／発光層／電子注入・輸送層／陰極
（９）陽極／絶縁層／発光層／絶縁層／陰極
（１０）陽極／無機半導体層／絶縁層／発光層／絶縁層／陰極
（１１）陽極／有機半導体層／絶縁層／発光層／絶縁層／陰極
（１２）陽極／絶縁層／正孔注入・輸送層／発光層／絶縁層／陰極
（１３）陽極／絶縁層／正孔注入・輸送層／発光層／電子注入・輸送層／陰極
等の構造を挙げることができる。
上記の中で（８）の構成が好ましく用いられるが、これらに限定されるものではない。 Representative element configurations of the organic EL element of the present invention include:
(1) anode/light-emitting layer/cathode (2) anode/hole-injection layer/light-emitting layer/cathode (3) anode/light-emitting layer/electron-injection and transport layer/cathode (4) anode/hole-injection layer/light-emitting layer/electron-injection and transport layer/cathode (5) anode/organic semiconductor layer/light-emitting layer/cathode (6) anode/organic semiconductor layer/electron-blocking layer/light-emitting layer/cathode (7) anode/organic semiconductor layer/light-emitting layer/adhesion-improving layer/cathode (8) anode/hole-injection and transport layer/light-emitting layer/ Examples of structures include electron injection/transport layer/cathode (9) anode/insulating layer/light-emitting layer/insulating layer/cathode (10) anode/inorganic semiconductor layer/insulating layer/light-emitting layer/insulating layer/cathode (11) anode/organic semiconductor layer/insulating layer/light-emitting layer/insulating layer/cathode (12) anode/insulating layer/hole injection/transport layer/light-emitting layer/insulating layer/cathode (13) anode/insulating layer/hole injection/transport layer/light-emitting layer/electron injection/transport layer/cathode.
Among the above, the configuration (8) is preferably used, but the present invention is not limited thereto.
発光層において、第１の発光層と第２の発光層の形成位置は限定されない。一実施形態において、前記発光層は、前記陽極の側から前記第１の発光層と前記第２の発光層とをこの順で有する。
In the light-emitting layer, the positions at which the first light-emitting layer and the second light-emitting layer are formed are not limited. In one embodiment, the light-emitting layer has the first light-emitting layer and the second light-emitting layer in this order from the anode side.
一実施形態において、前記第１の発光層と、前記第２の発光層とは、直接隣接する。
In one embodiment, the first light-emitting layer and the second light-emitting layer are directly adjacent.
本明細書中で「正孔注入・輸送層」は「正孔注入層及び正孔輸送層のうちの少なくともいずれか一方」を意味し、「電子注入・輸送層」は「電子注入層及び電子輸送層のうちの少なくともいずれか一方」を意味する。
In this specification, "hole injection/transport layer" means "at least one of a hole injection layer and a hole transport layer," and "electron injection/transport layer" means "at least one of an electron injection layer and an electron transport layer."
一実施形態において、本発明の一態様にかかる有機ＥＬ素子は、前記陽極と前記発光層との間に正孔輸送層を有する。
In one embodiment, the organic EL element according to one aspect of the present invention has a hole transport layer between the anode and the light-emitting layer.
一実施形態において、本発明の一態様にかかる有機ＥＬ素子は、前記陰極と前記発光層との間に電子輸送層を有する。
In one embodiment, the organic EL element according to one aspect of the present invention has an electron transport layer between the cathode and the light-emitting layer.
以下、本発明の一態様に係る有機ＥＬ素子で用いることができる部材、及び各層を構成する材料等について説明する。
The following describes the components that can be used in the organic EL element according to one embodiment of the present invention, as well as the materials that make up each layer.
（第１の発光層）
第１の発光層は、下記式（３）で表される化合物を含む。
［式（３）中、
Ｒ３０１～Ｒ３０５のうち１つは、下記式（Ａ３）で表される基と結合する単結合である。
（式（Ａ３）中、
ＬＡ３は、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の複素環基である。
ＡｒＡ３は、
置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の複素環基である。
ｎＡ３は０～３の整数である。
ｎＡ３が０である場合、（ＬＡ３）ｎＡ３は単結合である。
ｎＡ３が２又は３である場合、複数のＬＡ３は互いに直列状に連結し、ＡｒＡ３は、ジナフトフラン骨格から最も離れたＬＡ３に結合する。複数のＬＡ３は同一でもよく、異なってもよい。）
Ｒ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではないＲ３０１～Ｒ３０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではなく、互いに結合しないＲ３０１～Ｒ３０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ３）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。］ (First Light-Emitting Layer)
The first light-emitting layer contains a compound represented by the following formula (3).
[In formula (3),
One of R 301 to R 305 is a single bond bonded to a group represented by the following formula (A3).
(In formula (A3),
L A3 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
Ar A3 is
It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.
nA3 is an integer from 0 to 3.
When nA3 is 0, (L A3 ) nA3 is a single bond.
When nA3 is 2 or 3, multiple L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the most distant from the dinaphthofuran skeleton. Multiple L A3 may be the same or different.
Among R 306 to R 312 and R 301 to R 305 which are not single bonds bonded to the group represented by formula (A3), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 306 to R 312 which are not bonded to each other, and R 301 to R 305 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A3) each independently represent:
a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that is not the same as the group represented by formula (A3).]
第１の発光層は、下記式（３）で表される化合物を含む。
Ｒ３０１～Ｒ３０５のうち１つは、下記式（Ａ３）で表される基と結合する単結合である。
ＬＡ３は、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の複素環基である。
ＡｒＡ３は、
置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の複素環基である。
ｎＡ３は０～３の整数である。
ｎＡ３が０である場合、（ＬＡ３）ｎＡ３は単結合である。
ｎＡ３が２又は３である場合、複数のＬＡ３は互いに直列状に連結し、ＡｒＡ３は、ジナフトフラン骨格から最も離れたＬＡ３に結合する。複数のＬＡ３は同一でもよく、異なってもよい。）
Ｒ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではないＲ３０１～Ｒ３０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではなく、互いに結合しないＲ３０１～Ｒ３０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ３）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。］ (First Light-Emitting Layer)
The first light-emitting layer contains a compound represented by the following formula (3).
One of R 301 to R 305 is a single bond bonded to a group represented by the following formula (A3).
L A3 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
Ar A3 is
It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.
nA3 is an integer from 0 to 3.
When nA3 is 0, (L A3 ) nA3 is a single bond.
When nA3 is 2 or 3, multiple L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the most distant from the dinaphthofuran skeleton. Multiple L A3 may be the same or different.
Among R 306 to R 312 and R 301 to R 305 which are not single bonds bonded to the group represented by formula (A3), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 306 to R 312 which are not bonded to each other, and R 301 to R 305 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A3) each independently represent:
a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that is not the same as the group represented by formula (A3).]
式（３）において、「ｎＡ３が２又は３である場合、複数のＬＡ３は互いに直列状に連結し、ＡｒＡ３は、ジナフトフラン骨格から最も離れたＬＡ３に結合する。」について説明する。
定義から自明であるが、ｎＡ３が２又は３である場合、複数のＬＡ３は、ジナフトフラン骨格とＡｒＡ３との間で直列状に連結し、分岐しない。 In formula (3), "when nA3 is 2 or 3, a plurality of L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the furthest from the dinaphthofuran skeleton." will be explained.
As is obvious from the definition, when nA3 is 2 or 3, a plurality of L A3 are linked in series between the dinaphthofuran skeleton and Ar A3 , and are not branched.
定義から自明であるが、ｎＡ３が２又は３である場合、複数のＬＡ３は、ジナフトフラン骨格とＡｒＡ３との間で直列状に連結し、分岐しない。 In formula (3), "when nA3 is 2 or 3, a plurality of L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the furthest from the dinaphthofuran skeleton." will be explained.
As is obvious from the definition, when nA3 is 2 or 3, a plurality of L A3 are linked in series between the dinaphthofuran skeleton and Ar A3 , and are not branched.
例えば、Ｒ３０５が、式（Ａ３）で表される基と結合する単結合であり、ｎＡ３が３である場合、式（３）で表される化合物は、下記式（Ｅ３）で表される構造となる。
For example, when R 305 is a single bond bonded to the group represented by formula (A3), and nA3 is 3, the compound represented by formula (3) has a structure represented by the following formula (E3).
式（３）において、式（Ａ３）のＬＡ３が単結合である場合、ＡｒＡ３は、ジナフトフラン骨格に直接結合する。
In formula (3), when L A3 in formula (A3) is a single bond, Ar A3 is directly bonded to the dinaphthofuran skeleton.
「前記式（Ａ３）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基」について説明する。
「前記式（Ａ３）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが異なる場合、化学構造式（骨格）が互いに異なる場合と、化学構造式（骨格）は同一であるが異なる同位体を含む場合と、を含む。同位体とは、原子番号が等しく、中性子数が異なる原子を意味する。例えば、ベンゼン（Ｃ６Ｈ６）と重水素化ベンゼン（Ｃ６Ｄ６）とは互いに異なる。
また、「前記式（Ａ３）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが、同一の骨格の置換基を有するが、当該置換基の置換位置がそれぞれ異なる場合、「前記式（Ａ３）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とは同一ではない。 The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not identical to the group represented by formula (A3)" will now be described.
This includes cases where the "group represented by formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are different, where their chemical structural formulas (skeletons) are different, and where their chemical structural formulas (skeletons) are the same but contain different isotopes. An isotope means an atom with the same atomic number but a different number of neutrons. For example, benzene (C 6 H 6 ) and deuterated benzene (C 6 D 6 ) are different from each other.
Furthermore, when the "group represented by the formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" have substituents in the same skeleton but the substitution positions of the substituents are different, the "group represented by the formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are not identical to each other.
「前記式（Ａ３）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが異なる場合、化学構造式（骨格）が互いに異なる場合と、化学構造式（骨格）は同一であるが異なる同位体を含む場合と、を含む。同位体とは、原子番号が等しく、中性子数が異なる原子を意味する。例えば、ベンゼン（Ｃ６Ｈ６）と重水素化ベンゼン（Ｃ６Ｄ６）とは互いに異なる。
また、「前記式（Ａ３）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とが、同一の骨格の置換基を有するが、当該置換基の置換位置がそれぞれ異なる場合、「前記式（Ａ３）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とは同一ではない。 The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not identical to the group represented by formula (A3)" will now be described.
This includes cases where the "group represented by formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are different, where their chemical structural formulas (skeletons) are different, and where their chemical structural formulas (skeletons) are the same but contain different isotopes. An isotope means an atom with the same atomic number but a different number of neutrons. For example, benzene (C 6 H 6 ) and deuterated benzene (C 6 D 6 ) are different from each other.
Furthermore, when the "group represented by the formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" have substituents in the same skeleton but the substitution positions of the substituents are different, the "group represented by the formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are not identical to each other.
例えば、下記化合物は、「前記式（Ａ３）で表される基」と「置換もしくは無置換の環形成炭素数６～３０のアリール基」とがいずれもフェナントレン－９－イル基であるため、式（３）には含まれない。
For example, the compound below is not included in formula (3) because both the "group represented by formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are phenanthren-9-yl groups.
一実施形態において、Ｒ３０２～Ｒ３０５のうち１つは、前記式（Ａ３）で表される基と結合する単結合である。
In one embodiment, one of R 302 to R 305 is a single bond bonding to the group represented by formula (A3).
一実施形態において、Ｒ３０２、Ｒ３０３、及びＲ３０５のうち１つは、前記式（Ａ３）で表される基と結合する単結合である。
In one embodiment, one of R 302 , R 303 , and R 305 is a single bond bonding to the group represented by formula (A3).
一実施形態において、Ｒ３０３及びＲ３０５のうち１つは、前記式（Ａ３）で表される基と結合する単結合である。
In one embodiment, one of R 303 and R 305 is a single bond bonding to the group represented by formula (A3).
一実施形態において、ＬＡ３は、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である。 In one embodiment, L A3 is
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である。 In one embodiment, L A3 is
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
It is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group.
一実施形態において、ＬＡ３は、
単結合、又は
置換もしくは無置換のフェニレン基である。 In one embodiment, L A3 is
It is a single bond, or a substituted or unsubstituted phenylene group.
単結合、又は
置換もしくは無置換のフェニレン基である。 In one embodiment, L A3 is
It is a single bond, or a substituted or unsubstituted phenylene group.
一実施形態において、ＡｒＡ３は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である。 In one embodiment, Ar A3 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である。 In one embodiment, Ar A3 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
It is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group.
一実施形態において、ＡｒＡ３は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、又は
置換もしくは無置換のジベンゾフルオレニル基である。 In one embodiment, Ar A3 is
a substituted or unsubstituted phenyl group;
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、又は
置換もしくは無置換のジベンゾフルオレニル基である。 In one embodiment, Ar A3 is
a substituted or unsubstituted phenyl group;
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
It is a substituted or unsubstituted benzofluorenyl group, or a substituted or unsubstituted dibenzofluorenyl group.
一実施形態において、前記式（Ａ３）で表される基は、下記式（Ａ３－１）～式（Ａ３－７）のいずれかで表される基である。
［式（Ａ３－１）～式（Ａ３－７）中、ｎＡ３及びＬＡ３は、前記式（Ａ３）で定義した通りである。
ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルコキシ基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９４１）（Ｒ９４２）（Ｒ９４３）、
－Ｃ（＝Ｏ）Ｒ９４４、－ＣＯＯＲ９４５、
－Ｓ（＝Ｏ）２Ｒ９４６、
－Ｐ（＝Ｏ）（Ｒ９４７）（Ｒ９４８）、
－Ｇｅ（Ｒ９４９）（Ｒ９５０）（Ｒ９５１）、
－Ｎ（Ｒ９５２）（Ｒ９５３）、
ヒドロキシ基、
ハロゲン原子、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３が２以上存在する場合、２以上のＲ９４１～Ｒ９５３のそれぞれは同一でもよく、異なっていてもよい。］ In one embodiment, the group represented by formula (A3) is a group represented by any one of the following formulas (A3-1) to (A3-7).
[In formulas (A3-1) to (A3-7), nA3 and L A3 are as defined in formula (A3).
R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently
Hydrogen atom,
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkoxy group having 1 to 50 carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 941 )(R 942 )(R 943 ),
-C(=O)R 944 , -COOR 945 ,
-S(=O) 2 R 946 ,
-P(=O)(R 947 )(R 948 ),
-Ge(R 949 )(R 950 )(R 951 ),
-N(R 952 )(R 953 ),
Hydroxy groups,
Halogen atoms,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 941 to R 953 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 941 to R 953 are present, each of the two or more R 941 to R 953 may be the same or different.]
ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルコキシ基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９４１）（Ｒ９４２）（Ｒ９４３）、
－Ｃ（＝Ｏ）Ｒ９４４、－ＣＯＯＲ９４５、
－Ｓ（＝Ｏ）２Ｒ９４６、
－Ｐ（＝Ｏ）（Ｒ９４７）（Ｒ９４８）、
－Ｇｅ（Ｒ９４９）（Ｒ９５０）（Ｒ９５１）、
－Ｎ（Ｒ９５２）（Ｒ９５３）、
ヒドロキシ基、
ハロゲン原子、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３が２以上存在する場合、２以上のＲ９４１～Ｒ９５３のそれぞれは同一でもよく、異なっていてもよい。］ In one embodiment, the group represented by formula (A3) is a group represented by any one of the following formulas (A3-1) to (A3-7).
R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently
Hydrogen atom,
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkoxy group having 1 to 50 carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 941 )(R 942 )(R 943 ),
-C(=O)R 944 , -COOR 945 ,
-S(=O) 2 R 946 ,
-P(=O)(R 947 )(R 948 ),
-Ge(R 949 )(R 950 )(R 951 ),
-N(R 952 )(R 953 ),
Hydroxy groups,
Halogen atoms,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 941 to R 953 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 941 to R 953 are present, each of the two or more R 941 to R 953 may be the same or different.]
一実施形態において、前記式（Ａ３）で表される基は、前記式（Ａ３－１）～式（Ａ３－５）のいずれかで表される基である。
In one embodiment, the group represented by formula (A3) is a group represented by any one of formulas (A3-1) to (A3-5).
一実施形態において、前記式（３）で表される化合物は、下記式（３－１）～式（３－３）のいずれかで表される化合物である。
［式（３－１）～式（３－３）中、ｎＡ３、ＬＡ３、ＡｒＡ３、及びＲ３０１～Ｒ３１２は、前記式（１）で定義した通りである。］
In one embodiment, the compound represented by formula (3) is a compound represented by any one of formulas (3-1) to (3-3) below.
[In the formulas (3-1) to (3-3), nA3, L A3 , Ar A3 , and R 301 to R 312 are as defined in the formula (1).]
一実施形態において、前記式（３）で表される化合物は、前記式（３－１）又は式（３－２）で表される化合物である。
In one embodiment, the compound represented by formula (3) is a compound represented by formula (3-1) or formula (3-2).
一実施形態において、前記式（３）で表される化合物は、下記式（３－１１）～式（３－１９）のいずれかで表される化合物である。
［式（３－１１）～式（３－１９）中、ｎＡ３、ＬＡ３、Ｒ３０１～Ｒ３１２は、前記式（３）で定義した通りである。
ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルコキシ基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９４１）（Ｒ９４２）（Ｒ９４３）、
－Ｃ（＝Ｏ）Ｒ９４４、－ＣＯＯＲ９４５、
－Ｓ（＝Ｏ）２Ｒ９４６、
－Ｐ（＝Ｏ）（Ｒ９４７）（Ｒ９４８）、
－Ｇｅ（Ｒ９４９）（Ｒ９５０）（Ｒ９５１）、
－Ｎ（Ｒ９５２）（Ｒ９５３）、
ヒドロキシ基、
ハロゲン原子、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３が２以上存在する場合、２以上のＲ９４１～Ｒ９５３のそれぞれは同一でもよく、異なっていてもよい。］ In one embodiment, the compound represented by formula (3) is a compound represented by any one of formulas (3-11) to (3-19) below.
In formulas (3-11) to (3-19), nA3, L A3 and R 301 to R 312 are as defined in formula (3).
R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkoxy group having 1 to 50 carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 941 )(R 942 )(R 943 ),
-C(=O)R 944 , -COOR 945 ,
-S(=O) 2 R 946 ,
-P(=O)(R 947 )(R 948 ),
-Ge(R 949 )(R 950 )(R 951 ),
-N(R 952 )(R 953 ),
Hydroxy groups,
Halogen atoms,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 941 to R 953 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 941 to R 953 are present, each of the two or more R 941 to R 953 may be the same or different.]
ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルコキシ基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９４１）（Ｒ９４２）（Ｒ９４３）、
－Ｃ（＝Ｏ）Ｒ９４４、－ＣＯＯＲ９４５、
－Ｓ（＝Ｏ）２Ｒ９４６、
－Ｐ（＝Ｏ）（Ｒ９４７）（Ｒ９４８）、
－Ｇｅ（Ｒ９４９）（Ｒ９５０）（Ｒ９５１）、
－Ｎ（Ｒ９５２）（Ｒ９５３）、
ヒドロキシ基、
ハロゲン原子、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３が２以上存在する場合、２以上のＲ９４１～Ｒ９５３のそれぞれは同一でもよく、異なっていてもよい。］ In one embodiment, the compound represented by formula (3) is a compound represented by any one of formulas (3-11) to (3-19) below.
R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkoxy group having 1 to 50 carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 941 )(R 942 )(R 943 ),
-C(=O)R 944 , -COOR 945 ,
-S(=O) 2 R 946 ,
-P(=O)(R 947 )(R 948 ),
-Ge(R 949 )(R 950 )(R 951 ),
-N(R 952 )(R 953 ),
Hydroxy groups,
Halogen atoms,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 941 to R 953 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 941 to R 953 are present, each of the two or more R 941 to R 953 may be the same or different.]
一実施形態において、前記式（３）で表される化合物は、前記式（３－１１）～式（３－１４）のいずれかで表される化合物である。
In one embodiment, the compound represented by formula (3) is a compound represented by any one of formulas (3-11) to (3-14).
一実施形態において、単結合ではないＲ３０１～Ｒ３１２は、水素原子である。
In one embodiment, R 301 to R 312 that are not single bonds are hydrogen atoms.
一実施形態において、ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、及びＲＡ２６１～ＲＡ２７３は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。 In one embodiment, R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , and R A261 to R A273 are each independently:
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。 In one embodiment, R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , and R A261 to R A273 are each independently:
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
一実施形態において、ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、及びＲＡ２６１～ＲＡ２７３は、それぞれ独立に、
水素原子、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、又は
環形成原子数５～１８の１価の複素環基である。 In one embodiment, R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , and R A261 to R A273 are each independently:
Hydrogen atom,
an alkyl group having 1 to 18 carbon atoms,
It is an aryl group having 6 to 18 ring carbon atoms, or a monovalent heterocyclic group having 5 to 18 ring atoms.
水素原子、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、又は
環形成原子数５～１８の１価の複素環基である。 In one embodiment, R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , and R A261 to R A273 are each independently:
Hydrogen atom,
an alkyl group having 1 to 18 carbon atoms,
It is an aryl group having 6 to 18 ring carbon atoms, or a monovalent heterocyclic group having 5 to 18 ring atoms.
一実施形態において、ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９は、それぞれ独立に、
水素原子、
メチル基、
フェニル基、又は
ナフチル基である。 In one embodiment, R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently:
Hydrogen atoms,
Methyl group,
It is a phenyl group or a naphthyl group.
水素原子、
メチル基、
フェニル基、又は
ナフチル基である。 In one embodiment, R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently:
Hydrogen atoms,
Methyl group,
It is a phenyl group or a naphthyl group.
一実施形態において、ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９は、それぞれ独立に、水素原子、メチル基、又はフェニル基である。
In one embodiment, R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently a hydrogen atom, a methyl group, or a phenyl group.
一実施形態において、ＲＡ２１１～ＲＡ２１４及びＲＡ２１６～ＲＡ２１９は、水素原子であり、ＲＡ２１５は、フェニル基である。
In one embodiment, R A211 to R A214 and R A216 to R A219 are hydrogen atoms, and R A215 is a phenyl group.
一実施形態において、ＲＡ２１１～ＲＡ２１９は、水素原子である。
In one embodiment, R A211 to R A219 are hydrogen atoms.
一実施形態において、ＲＡ２２１～ＲＡ２２６及びＲＡ２２８～ＲＡ２３２は、水素原子である。
In one embodiment, R A221 to R A226 and R A228 to R A232 are hydrogen atoms.
一実施形態において、ＲＡ２２１～ＲＡ２２６及びＲＡ２２８～ＲＡ２３１は、水素原子であり、ＲＡ２２７は、フェニル基である。
In one embodiment, R A221 to R A226 and R A228 to R A231 are hydrogen atoms, and R A227 is a phenyl group.
一実施形態において、ＲＡ２４１～ＲＡ２４９及びＲＡ２６１～ＲＡ２７１は、水素原子であり、ＲＡ２５０～ＲＡ２５１及びＲＡ２７２～ＲＡ２７３は、メチル基である。
In one embodiment, R A241 to R A249 and R A261 to R A271 are hydrogen atoms, and R A250 to R A251 and R A272 to R A273 are methyl groups.
一実施形態において、ＲＡ２８１～ＲＡ２８９は、水素原子である。
In one embodiment, R A281 to R A289 are hydrogen atoms.
一実施形態において、ＲＡ２９１～ＲＡ２９９は、水素原子である。
In one embodiment, R A291 to R A299 are hydrogen atoms.
一実施形態において、水素原子であるＲＡ２８１～ＲＡ２８９のうち少なくとも１つは、重水素原子である。
In one embodiment, at least one of R A281 to R A289 which are hydrogen atoms is a deuterium atom.
一実施形態において、水素原子であるＲＡ２９１～ＲＡ２９９のうち少なくとも１つは、重水素原子である。
In one embodiment, at least one of R A291 to R A299 which are hydrogen atoms is a deuterium atom.
本明細書において、水素原子が「重水素原子である」とは、当該水素原子において、軽水素原子と重水素原子の合計に対して、重水素原子の割合が天然存在比より多いことを意味する。軽水素原子と重水素原子の合計に対して、重水素原子の割合が天然存在比より多いことは、核磁気共鳴装置により確認することができる。
In this specification, when a hydrogen atom is "a deuterium atom," it means that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms in the hydrogen atom is greater than the natural abundance ratio. The fact that the ratio of deuterium atoms to the total of light hydrogen atoms and deuterium atoms is greater than the natural abundance ratio can be confirmed using a nuclear magnetic resonance spectrometer.
一実施形態において、前記式（３）における「置換もしくは無置換の」という場合における置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルコキシ基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｓ（＝Ｏ）２Ｒ４６、
－Ｐ（＝Ｏ）（Ｒ４７）（Ｒ４８）、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
－Ｎ（Ｒ５２）（Ｒ５３）、
ヒドロキシ基、
ハロゲン原子、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の１価の複素環基からなる群から選択される。
Ｒ４１～Ｒ５３は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ５３が２以上存在する場合、２以上のＲ４１～Ｒ５３のそれぞれは同一でもよく、異なっていてもよい。 In one embodiment, the substituent in the case of “substituted or unsubstituted” in the formula (3) is
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkoxy group having 1 to 50 carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-S(=O) 2 R 46 ,
-P(=O)(R 47 )(R 48 ),
-Ge(R 49 )(R 50 )(R 51 ),
-N(R 52 )(R 53 ),
Hydroxy groups,
Halogen atoms,
Cyano group,
Nitro group,
It is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 53 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 53 are present, each of the two or more R 41 to R 53 may be the same or different.
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルコキシ基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｓ（＝Ｏ）２Ｒ４６、
－Ｐ（＝Ｏ）（Ｒ４７）（Ｒ４８）、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
－Ｎ（Ｒ５２）（Ｒ５３）、
ヒドロキシ基、
ハロゲン原子、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の１価の複素環基からなる群から選択される。
Ｒ４１～Ｒ５３は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ５３が２以上存在する場合、２以上のＲ４１～Ｒ５３のそれぞれは同一でもよく、異なっていてもよい。 In one embodiment, the substituent in the case of “substituted or unsubstituted” in the formula (3) is
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkoxy group having 1 to 50 carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-S(=O) 2 R 46 ,
-P(=O)(R 47 )(R 48 ),
-Ge(R 49 )(R 50 )(R 51 ),
-N(R 52 )(R 53 ),
Hydroxy groups,
Halogen atoms,
Cyano group,
Nitro group,
It is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 53 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 53 are present, each of the two or more R 41 to R 53 may be the same or different.
一実施形態において、前記式（３）における「置換もしくは無置換の」という場合における置換基は、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の１価の複素環基からなる群から選択される。 In one embodiment, the substituent in the case of “substituted or unsubstituted” in the formula (3) is
an alkyl group having 1 to 50 carbon atoms,
It is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の１価の複素環基からなる群から選択される。 In one embodiment, the substituent in the case of “substituted or unsubstituted” in the formula (3) is
an alkyl group having 1 to 50 carbon atoms,
It is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
一実施形態において、前記式（３）で表される化合物は、前記式（１）で表される化合物である。
一実施形態において、前記式（３）で表される化合物は、前記式（２）で表される化合物である。 In one embodiment, the compound represented by formula (3) is a compound represented by formula (1).
In one embodiment, the compound represented by formula (3) is a compound represented by formula (2).
一実施形態において、前記式（３）で表される化合物は、前記式（２）で表される化合物である。 In one embodiment, the compound represented by formula (3) is a compound represented by formula (1).
In one embodiment, the compound represented by formula (3) is a compound represented by formula (2).
式（３）で表される化合物は、実施例に倣い、目的物に合わせた既知の代替反応や原料を用いることで合成することができる。
The compound represented by formula (3) can be synthesized by following the examples and using known alternative reactions and raw materials that are appropriate for the target product.
式（３）で表される化合物の具体例としては、上述した式（１）又は式（２）で表される化合物の具体例が挙げられる。これらは例示に過ぎず、式（３）で表される化合物は、上述した式（１）又は式（２）で表される化合物の具体例に限定されるものではない。
Specific examples of the compound represented by formula (3) include the specific examples of the compounds represented by formula (1) or formula (2) described above. These are merely examples, and the compound represented by formula (3) is not limited to the specific examples of the compounds represented by formula (1) or formula (2) described above.
式（３）で表される化合物の具体例としては、上述した式（１）又は式（２）で表される化合物の具体例のほか、以下の化合物が挙げられる。これらは例示に過ぎず、式（３）で表される化合物は下記具体例に限定されるものではない。
Specific examples of compounds represented by formula (3) include the following compounds in addition to the specific examples of compounds represented by formula (1) or formula (2) described above. These are merely examples, and compounds represented by formula (3) are not limited to the specific examples below.
一実施形態において、第１の発光層は、上記式（３）で表される化合物と、第２の化合物と、を含む。
上記式（３）で表される化合物と、第２の化合物と、は、互いに異なる。 In one embodiment, the first light-emitting layer contains a compound represented by formula (3) above and a second compound.
The compound represented by the formula (3) and the second compound are different from each other.
上記式（３）で表される化合物と、第２の化合物と、は、互いに異なる。 In one embodiment, the first light-emitting layer contains a compound represented by formula (3) above and a second compound.
The compound represented by the formula (3) and the second compound are different from each other.
（第２の化合物）
一実施形態において、第２の化合物は、発光材料である。
一実施形態において、第２の化合物は、蛍光発光性の化合物である。
一実施形態において、第２の化合物は、蛍光発光最大ピーク波長が４３０ｎｍ以上４８０ｎｍ以下の発光を示す化合物である。本明細書において、蛍光発光の最大ピーク波長を、蛍光発光最大ピーク波長と称する場合がある。 (Second Compound)
In one embodiment, the second compound is an emissive material.
In one embodiment, the second compound is a fluorescent compound.
In one embodiment, the second compound is a compound that exhibits emission having a maximum fluorescent emission peak wavelength of 430 nm or more and 480 nm or less. In this specification, the maximum fluorescent emission peak wavelength may be referred to as the maximum fluorescent emission peak wavelength.
一実施形態において、第２の化合物は、発光材料である。
一実施形態において、第２の化合物は、蛍光発光性の化合物である。
一実施形態において、第２の化合物は、蛍光発光最大ピーク波長が４３０ｎｍ以上４８０ｎｍ以下の発光を示す化合物である。本明細書において、蛍光発光の最大ピーク波長を、蛍光発光最大ピーク波長と称する場合がある。 (Second Compound)
In one embodiment, the second compound is an emissive material.
In one embodiment, the second compound is a fluorescent compound.
In one embodiment, the second compound is a compound that exhibits emission having a maximum fluorescent emission peak wavelength of 430 nm or more and 480 nm or less. In this specification, the maximum fluorescent emission peak wavelength may be referred to as the maximum fluorescent emission peak wavelength.
本明細書において、蛍光発光最大ピーク波長とは、測定対象となる化合物が、１０－６モル／リットル以上、１０－５モル／リットル以下の濃度で溶解しているトルエン溶液について、測定した蛍光スペクトルにおける発光強度が最大となる蛍光スペクトルの最大ピーク波長をいう。測定装置は、蛍光スペクトル測定装置（装置名：ＦＰ－８３００、日本分光株式会社製）を用いることができる。なお、蛍光スペクトル測定装置は、ここで例示した装置に限定されない。
In this specification, the maximum fluorescence emission peak wavelength refers to the maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound to be measured is dissolved at a concentration of 10 −6 mol/L or more and 10 −5 mol/L or less. The measurement device may be a fluorescence spectrum measuring device (device name: FP-8300, manufactured by JASCO Corporation). Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.
第２の化合物としては、例えば、ビスアリールアミノナフタレン誘導体、アリール置換ナフタレン誘導体、ビスアリールアミノアントラセン誘導体、アリール置換アントラセン誘導体、ビスアリールアミノピレン誘導体、アリール置換ピレン誘導体、ビスアリールアミノクリセン誘導体、アリール置換クリセン誘導体、ビスアリールアミノフルオランテン誘導体、アリール置換フルオランテン誘導体、インデノペリレン誘導体、アセナフトフルオランテン誘導体、ホウ素原子を含む化合物、ピロメテンホウ素錯体化合物、ピロメテン骨格を有する化合物、ピロメテン骨格を有する化合物の金属錯体、ジケトピロロピロール誘導体、ペリレン誘導体、及びナフタセン誘導体等が挙げられる。
Examples of the second compound include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing boron atoms, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.
第２の化合物としては、例えば、下記式（Ｄ１）で表される化合物、下記式（Ｄ２）で表される化合物、下記式（Ｄ３）で表される化合物、及び下記式（Ｄ４）で表される化合物からなる群から選択される１以上の化合物が挙げられる。
The second compound may be, for example, one or more compounds selected from the group consisting of a compound represented by the following formula (D1), a compound represented by the following formula (D2), a compound represented by the following formula (D3), and a compound represented by the following formula (D4).
（式（Ｄ１）で表される化合物）
式（Ｄ１）で表される化合物について説明する。 (Compound represented by formula (D1))
The compound represented by formula (D1) will be described.
式（Ｄ１）で表される化合物について説明する。 (Compound represented by formula (D1))
The compound represented by formula (D1) will be described.
Ｚは、それぞれ独立に、ＣＲａ又は窒素原子である。
Ａ１環及びＡ２環は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０の芳香族炭化水素環、又は
置換もしくは無置換の環形成原子数５～５０の複素環である。
Ｒａが複数存在する場合、複数のＲａのうちの隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
ｎ２１及びｎ２２は、それぞれ独立に、０、１、２、３、又は４である。
Ｒｂが複数存在する場合、複数のＲｂのうちの隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
Ｒｃが複数存在する場合、複数のＲｃのうちの隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲａ、Ｒｂ、及びＲｃは、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｒ９０１～Ｒ９０７が２以上存在する場合、２以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。）
Each Z is independently CRa or a nitrogen atom.
Ring A1 and ring A2 each independently represent
It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
When a plurality of Ra's are present, one or more pairs of adjacent two or more of the plurality of Ra's are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
n21 and n22 each independently represent 0, 1, 2, 3, or 4.
When a plurality of Rb's are present, one or more pairs of adjacent two or more of the plurality of Rb's are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
When a plurality of Rc's are present, one or more pairs of adjacent two or more of the plurality of Rc's are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
Ra, Rb, and Rc that are not bonded to each other are each independently
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 each independently represent
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 901 to R 907 are present, each of the two or more R 901 to R 907 may be the same or different.
Ａ１環及びＡ２環の「芳香族炭化水素環」としては、例えば、上述した「環形成炭素数６～５０のアリール基」に水素原子を導入した化合物と同じ構造が挙げられる。
Ａ１環及びＡ２環の「芳香族炭化水素環」は、前記式（Ｄ１）の中央の縮合２環構造上の炭素原子２つを環形成原子として含む。
「置換もしくは無置換の環形成炭素数６～５０の芳香族炭化水素環」の具体例としては、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」に水素原子を導入した化合物等が挙げられる。 Examples of the "aromatic hydrocarbon ring" of ring A1 and ring A2 include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms".
The "aromatic hydrocarbon ring" of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of formula (D1) as ring-forming atoms.
Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted aryl group” described in specific example group G1.
Ａ１環及びＡ２環の「芳香族炭化水素環」は、前記式（Ｄ１）の中央の縮合２環構造上の炭素原子２つを環形成原子として含む。
「置換もしくは無置換の環形成炭素数６～５０の芳香族炭化水素環」の具体例としては、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」に水素原子を導入した化合物等が挙げられる。 Examples of the "aromatic hydrocarbon ring" of ring A1 and ring A2 include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms".
The "aromatic hydrocarbon ring" of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of formula (D1) as ring-forming atoms.
Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted aryl group” described in specific example group G1.
Ａ１環及びＡ２環の「複素環」としては、例えば、上述した「環形成原子数５～５０の複素環基」に水素原子を導入した化合物と同じ構造が挙げられる。
Ａ１環及びＡ２環の「複素環」は、前記式（Ｄ１）の中央の縮合２環構造上の炭素原子２つを環形成原子として含む。
「置換もしくは無置換の環形成原子数５～５０の複素環」の具体例としては、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」に水素原子を導入した化合物等が挙げられる。 Examples of the "heterocycle" of ring A1 and ring A2 include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocycle group having 5 to 50 ring atoms".
The "heterocycle" of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of formula (D1) as ring-forming atoms.
Specific examples of the “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted heterocyclic group” described in specific example group G2.
Ａ１環及びＡ２環の「複素環」は、前記式（Ｄ１）の中央の縮合２環構造上の炭素原子２つを環形成原子として含む。
「置換もしくは無置換の環形成原子数５～５０の複素環」の具体例としては、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」に水素原子を導入した化合物等が挙げられる。 Examples of the "heterocycle" of ring A1 and ring A2 include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocycle group having 5 to 50 ring atoms".
The "heterocycle" of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of formula (D1) as ring-forming atoms.
Specific examples of the “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted heterocyclic group” described in specific example group G2.
Ｒｂは、Ａ１環としての芳香族炭化水素環を形成する炭素原子のいずれか、又は、Ａ１環としての複素環を形成する原子のいずれかに結合する。
Rb is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A1, or any of the atoms forming the heterocyclic ring as ring A1.
Ｒｃは、Ａ２環としての芳香族炭化水素環を形成する炭素原子のいずれか、又は、Ａ２環としての複素環を形成する原子のいずれかに結合する。
Rc is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A2, or any of the atoms forming the heterocycle as ring A2.
一実施形態において、Ｒａ、Ｒｂ、及びＲｃのうち、少なくとも１つは、下記式（Ｄ１ａ）で表される基である。
一実施形態において、Ｒａ、Ｒｂ、及びＲｃのうち、少なくとも２つは、下記式（Ｄ１ａ）で表される基である。 In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D1a):
In one embodiment, at least two of Ra, Rb, and Rc are a group represented by the following formula (D1a).
一実施形態において、Ｒａ、Ｒｂ、及びＲｃのうち、少なくとも２つは、下記式（Ｄ１ａ）で表される基である。 In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D1a):
In one embodiment, at least two of Ra, Rb, and Rc are a group represented by the following formula (D1a).
ＬＤ１０１は、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の複素環基である。
ＡｒＤ１０１は、
置換もしくは無置換の環形成炭素数６～５０のアリール基、
置換もしくは無置換の環形成原子数５～５０の１価の複素環基、又は
下記式（Ｄ１ｂ）で表される基である。）
ＬＤ１０２及びＬＤ１０３は、それぞれ独立に、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の複素環基である。
ＡｒＤ１０２及びＡｒＤ１０３からなる組は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＡｒＤ１０２及びＡｒＤ１０３は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。）
LD101 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
Ar D101 is
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (D1b):
L D102 and L D103 are each independently
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
A pair consisting of Ar D102 and Ar D103 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
Ar D102 and Ar D103 which are not bonded to each other are each independently
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
一実施形態において、Ｒ９０１～Ｒ９０７は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, R 901 to R 907 are each independently
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
置換もしくは無置換の炭素数１～５０のアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, R 901 to R 907 are each independently
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
式（Ｄ１）で表される化合物は、目的物に合わせた既知の反応や原料を用いることで合成することができる。
The compound represented by formula (D1) can be synthesized by using known reactions and raw materials that are suited to the target product.
式（Ｄ１）で表される化合物の具体例としては、以下の化合物が挙げられる。これらは例示に過ぎず、式（Ｄ１）で表される化合物は下記具体例に限定されるものではない。
Specific examples of compounds represented by formula (D1) include the following compounds. These are merely examples, and compounds represented by formula (D1) are not limited to the following specific examples.
（式（Ｄ２）で表される化合物）
式（Ｄ２）で表される化合物について説明する。 (Compound represented by formula (D2))
The compound represented by formula (D2) will be described.
式（Ｄ２）で表される化合物について説明する。 (Compound represented by formula (D2))
The compound represented by formula (D2) will be described.
ＲＤ２０１～ＲＤ２０７及びＲＤ２１１～ＲＤ２１７のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲＤ２０１～ＲＤ２０７及びＲＤ２１１～ＲＤ２１７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
ＲＤ２２１及びＲＤ２２２は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｒ９０１～Ｒ９０７は、前記式（Ｄ１）で定義した通りである。）
One or more pairs of adjacent two or more of R D201 to R D207 and R D211 to R D217 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R D201 to R D207 and R D211 to R D217 that are not bonded to each other each independently represent
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 )
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R and R are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in formula (D1).
「ＲＤ２０１～ＲＤ２０７及びＲＤ２１１～ＲＤ２１７のうちの隣接する２つ以上からなる組の１組」は、例えば、ＲＤ２０１とＲＤ２０２からなる組、ＲＤ２０２とＲＤ２０３からなる組、ＲＤ２０３とＲＤ２０４からなる組、ＲＤ２０５とＲＤ２０６からなる組、ＲＤ２０６とＲＤ２０７からなる組、ＲＤ２０１とＲＤ２０２とＲＤ２０３からなる組等の組合せである。
"One of the groups consisting of two or more adjacent pairs of R D201 to R D207 and R D211 to R D217 " is, for example, a combination such as a group consisting of R D201 and R D202 , a group consisting of R D202 and R D203 , a group consisting of R D203 and R D204 , a group consisting of R D205 and R D206 , a group consisting of R D206 and R D207 , or a group consisting of R D201 , R D202 and R D203 .
一実施形態において、ＲＤ２０１～ＲＤ２０７及びＲＤ２１１～ＲＤ２１７の少なくとも１つは、－Ｎ（Ｒ９０６）（Ｒ９０７）である。
In one embodiment, at least one of R D201 -R D207 and R D211 -R D217 is --N(R 906 )(R 907 ).
一実施形態において、ＲＤ２０１～ＲＤ２０７及びＲＤ２１１～ＲＤ２１７の少なくとも２つは、－Ｎ（Ｒ９０６）（Ｒ９０７）である。
In one embodiment, at least two of R D201 -R D207 and R D211 -R D217 are --N(R 906 )(R 907 ).
一実施形態において、ＲＤ２０１～ＲＤ２０７の少なくとも１つは、－Ｎ（Ｒ９０６）（Ｒ９０７）である。
一実施形態において、ＲＤ２１１～ＲＤ２１７の少なくとも１つは、－Ｎ（Ｒ９０６）（Ｒ９０７）である。 In one embodiment, at least one of R D201 to R D207 is --N(R 906 )(R 907 ).
In one embodiment, at least one of R D211 to R D217 is --N(R 906 )(R 907 ).
一実施形態において、ＲＤ２１１～ＲＤ２１７の少なくとも１つは、－Ｎ（Ｒ９０６）（Ｒ９０７）である。 In one embodiment, at least one of R D201 to R D207 is --N(R 906 )(R 907 ).
In one embodiment, at least one of R D211 to R D217 is --N(R 906 )(R 907 ).
一実施形態において、ＲＤ２０１～ＲＤ２０７の少なくとも１つ、及びＲＤ２１１～ＲＤ２１７の少なくとも１つは、それぞれ独立に、－Ｎ（Ｒ９０６）（Ｒ９０７）である。
In one embodiment, at least one of R D201 -R D207 , and at least one of R D211 -R D217 are each independently -N(R 906 )(R 907 ).
一実施形態において、－Ｎ（Ｒ９０６）（Ｒ９０７）ではないＲＤ２０１～ＲＤ２０７及びＲＤ２１１～ＲＤ２１７は、それぞれ独立に、
水素原子、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D201 -R D207 and R D211 -R D217 that are not —N(R 906 )(R 907 ) are each independently
Hydrogen atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
水素原子、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D201 -R D207 and R D211 -R D217 that are not —N(R 906 )(R 907 ) are each independently
Hydrogen atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
式（Ｄ２）で表される化合物は、目的物に合わせた既知の反応や原料を用いることで合成することができる。
The compound represented by formula (D2) can be synthesized by using known reactions and raw materials that are suited to the target product.
式（Ｄ２）で表される化合物の具体例としては、以下の化合物が挙げられる。これらは例示に過ぎず、式（Ｄ２）で表される化合物は下記具体例に限定されるものではない。
Specific examples of compounds represented by formula (D2) include the following compounds. These are merely examples, and compounds represented by formula (D2) are not limited to the following specific examples.
（式（Ｄ３）で表される化合物）
式（Ｄ３）で表される化合物について説明する。 (Compound represented by formula (D3))
The compound represented by formula (D3) will be described.
式（Ｄ３）で表される化合物について説明する。 (Compound represented by formula (D3))
The compound represented by formula (D3) will be described.
ａ環、ｂ環及びｃ環は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０の芳香族炭化水素環、又は
置換もしくは無置換の環形成原子数５～５０の複素環である。
ＲＤ３０１及びＲＤ３０２は、それぞれ独立に、前記ａ環、ｂ環、又はｃ環と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
前記置換もしくは無置換の複素環を形成しないＲＤ３０１及びＲＤ３０２は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。）
Ring a, ring b and ring c each independently represent
It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
R D301 and R D302 each independently bond to the ring a, ring b or ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.
R and R which do not form a substituted or unsubstituted heterocycle are each independently
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
ａ環、ｂ環、及びｃ環は、ホウ素原子、２つの窒素原子、及び７つの炭素原子から構成される前記式（Ｄ３）の中央の縮合２環構造に縮合する。
The a, b, and c rings are fused to a central fused two-ring structure of formula (D3) consisting of a boron atom, two nitrogen atoms, and seven carbon atoms.
ａ環、ｂ環及びｃ環の「芳香族炭化水素環」は、上述した「環形成炭素数６～５０のアリール基」に水素原子を導入した化合物と同じ構造である。
ａ環の「芳香族炭化水素環」は、前記式（Ｄ３）の中央の縮合２環構造上の炭素原子３つを環形成原子として含む。
ｂ環及びｃ環の「芳香族炭化水素環」は、前記式（Ｄ３）の中央の縮合２環構造上の炭素原子２つを環形成原子として含む。 The "aromatic hydrocarbon rings" of ring a, ring b and ring c have the same structure as the compound in which a hydrogen atom has been introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms".
The "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of formula (D3) as ring-forming atoms.
The "aromatic hydrocarbon ring" of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of formula (D3) as ring-forming atoms.
ａ環の「芳香族炭化水素環」は、前記式（Ｄ３）の中央の縮合２環構造上の炭素原子３つを環形成原子として含む。
ｂ環及びｃ環の「芳香族炭化水素環」は、前記式（Ｄ３）の中央の縮合２環構造上の炭素原子２つを環形成原子として含む。 The "aromatic hydrocarbon rings" of ring a, ring b and ring c have the same structure as the compound in which a hydrogen atom has been introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms".
The "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of formula (D3) as ring-forming atoms.
The "aromatic hydrocarbon ring" of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of formula (D3) as ring-forming atoms.
「置換もしくは無置換の環形成炭素数６～５０の芳香族炭化水素環」の具体例としては、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」に水素原子を導入した化合物等が挙げられる。
ａ環、ｂ環、及びｃ環の「複素環」としては、例えば、上述した「環形成原子数５～５０の複素環基」に水素原子を導入した化合物と同じ構造が挙げられる。
ａ環の「複素環」は、前記式（Ｄ３）の中央の縮合２環構造上の炭素原子３つを環形成原子として含む。ｂ環及びｃ環の「複素環」は、前記式（Ｄ３）の中央の縮合２環構造上の炭素原子２つを環形成原子として含む。「置換もしくは無置換の環形成原子数５～５０の複素環」の具体例としては、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」に水素原子を導入した化合物等が挙げられる。 Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted aryl group” described in specific example group G1.
Examples of the "heterocyclic ring" of ring a, ring b, and ring c include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group having 5 to 50 ring atoms".
The "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of formula (D3) as ring-forming atoms. The "heterocycle" of ring b and ring c contains two carbon atoms on the central fused bicyclic structure of formula (D3) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
ａ環、ｂ環、及びｃ環の「複素環」としては、例えば、上述した「環形成原子数５～５０の複素環基」に水素原子を導入した化合物と同じ構造が挙げられる。
ａ環の「複素環」は、前記式（Ｄ３）の中央の縮合２環構造上の炭素原子３つを環形成原子として含む。ｂ環及びｃ環の「複素環」は、前記式（Ｄ３）の中央の縮合２環構造上の炭素原子２つを環形成原子として含む。「置換もしくは無置換の環形成原子数５～５０の複素環」の具体例としては、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」に水素原子を導入した化合物等が挙げられる。 Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “substituted or unsubstituted aryl group” described in specific example group G1.
Examples of the "heterocyclic ring" of ring a, ring b, and ring c include the same structures as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group having 5 to 50 ring atoms".
The "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of formula (D3) as ring-forming atoms. The "heterocycle" of ring b and ring c contains two carbon atoms on the central fused bicyclic structure of formula (D3) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
ＲＤ３０１及びＲＤ３０２は、それぞれ独立に、ａ環、ｂ環、又はｃ環と結合して、置換もしくは無置換の複素環を形成してもよい。この場合における複素環は、前記式（Ｄ３）の中央の縮合２環構造上の窒素原子を含む。この場合における複素環は、窒素原子以外のヘテロ原子を含んでいてもよい。ＲＤ３０１又はＲＤ３０２がａ環、ｂ環又はｃ環と結合するとは、具体的には、ａ環、ｂ環、又はｃ環を構成する原子と、ＲＤ３０１又はＲＤ３０２を構成する原子と、が結合することを意味する。例えば、ＲＤ３０１がａ環と結合して、ＲＤ３０１を含む環とａ環が縮合した２環縮合、３環縮合、４環縮合、又は５環以上縮合の含窒素複素環を形成してもよい。当該含窒素複素環の具体例としては、具体例群Ｇ２のうち、窒素を含む２環縮合以上の複素環基に対応する化合物等が挙げられる。
ＲＤ３０１がｂ環と結合する場合、ＲＤ３０２がａ環と結合する場合、及びＲＤ３０２がｃ環と結合する場合も上記と同じである。 R D301 and R D302 may each independently bond to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle. The heterocycle in this case includes the nitrogen atom on the central fused two-ring structure of the formula (D3). The heterocycle in this case may include a heteroatom other than a nitrogen atom. Specifically, R D301 or R D302 bonded to the ring a, ring b, or ring c means that an atom constituting the ring a, ring b, or ring c is bonded to an atom constituting R D301 or R D302 . For example, R D301 may bond to the ring a to form a two-ring fused, three-ring fused, four-ring fused, or five-ring or more fused nitrogen-containing heterocycle in which the ring containing R D301 is fused to the ring a. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two-ring or more fused heterocyclic group in the specific example group G2.
The above applies when R D301 is bonded to ring b, when R D302 is bonded to ring a, and when R D302 is bonded to ring c.
ＲＤ３０１がｂ環と結合する場合、ＲＤ３０２がａ環と結合する場合、及びＲＤ３０２がｃ環と結合する場合も上記と同じである。 R D301 and R D302 may each independently bond to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle. The heterocycle in this case includes the nitrogen atom on the central fused two-ring structure of the formula (D3). The heterocycle in this case may include a heteroatom other than a nitrogen atom. Specifically, R D301 or R D302 bonded to the ring a, ring b, or ring c means that an atom constituting the ring a, ring b, or ring c is bonded to an atom constituting R D301 or R D302 . For example, R D301 may bond to the ring a to form a two-ring fused, three-ring fused, four-ring fused, or five-ring or more fused nitrogen-containing heterocycle in which the ring containing R D301 is fused to the ring a. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two-ring or more fused heterocyclic group in the specific example group G2.
The above applies when R D301 is bonded to ring b, when R D302 is bonded to ring a, and when R D302 is bonded to ring c.
一実施形態において、前記式（Ｄ３）におけるａ環、ｂ環、及びｃ環は、それぞれ独立に、置換もしくは無置換の環形成炭素数６～５０の芳香族炭化水素環である。
一実施形態において、前記式（Ｄ３）におけるａ環、ｂ環、及びｃ環は、それぞれ独立に、置換もしくは無置換のベンゼン環又はナフタレン環である。 In one embodiment, the ring a, ring b, and ring c in the formula (D3) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
In one embodiment, the ring a, the ring b, and the ring c in the formula (D3) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
一実施形態において、前記式（Ｄ３）におけるａ環、ｂ環、及びｃ環は、それぞれ独立に、置換もしくは無置換のベンゼン環又はナフタレン環である。 In one embodiment, the ring a, ring b, and ring c in the formula (D3) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
In one embodiment, the ring a, the ring b, and the ring c in the formula (D3) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
一実施形態において、前記式（Ｄ３）におけるＲＤ３０１及びＲＤ３０２は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R and R in formula (D3) are each independently
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R and R in formula (D3) are each independently
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
一実施形態において、前記式（Ｄ３）におけるＲＤ３０１及びＲＤ３０２は、それぞれ独立に、置換もしくは無置換の環形成炭素数６～５０のアリール基である。
In one embodiment, R D301 and R D302 in the formula (D3) each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
一実施形態において、前記式（Ｄ３）で表される化合物は、下記式（Ｄ３２）で表される化合物である。
（式（Ｄ３２）中、
ＲＤ３０１Ａは、ＲＤ３１１及びＲＤ３２１からなる群から選択される１以上と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３０２Ａは、ＲＤ３１３及びＲＤ３１４からなる群から選択される１以上と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
前記置換もしくは無置換の複素環を形成しないＲＤ３０１Ａ及びＲＤ３０２Ａは、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
ＲＤ３１１～ＲＤ３２１のうちの隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
前記置換もしくは無置換の複素環を形成せず、前記単環を形成せず、かつ前記縮合環を形成しないＲＤ３１１～ＲＤ３２１は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｒ９０１～Ｒ９０７は、前記式（Ｄ１）で定義した通りである。） In one embodiment, the compound represented by formula (D3) is a compound represented by formula (D32):
(In formula (D32),
R D301A combines with one or more selected from the group consisting of R D311 and R D321 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D302A combines with one or more selected from the group consisting of R D313 and R D314 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D301A and R D302A which do not form a substituted or unsubstituted heterocycle are each independently
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
One or more pairs of adjacent two or more of R D311 to R D321 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R D311 to R D321 which do not form a substituted or unsubstituted heterocycle, do not form a monocycle, and do not form a fused ring are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in formula (D1).
ＲＤ３０１Ａは、ＲＤ３１１及びＲＤ３２１からなる群から選択される１以上と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３０２Ａは、ＲＤ３１３及びＲＤ３１４からなる群から選択される１以上と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
前記置換もしくは無置換の複素環を形成しないＲＤ３０１Ａ及びＲＤ３０２Ａは、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
ＲＤ３１１～ＲＤ３２１のうちの隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
前記置換もしくは無置換の複素環を形成せず、前記単環を形成せず、かつ前記縮合環を形成しないＲＤ３１１～ＲＤ３２１は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｒ９０１～Ｒ９０７は、前記式（Ｄ１）で定義した通りである。） In one embodiment, the compound represented by formula (D3) is a compound represented by formula (D32):
R D301A combines with one or more selected from the group consisting of R D311 and R D321 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D302A combines with one or more selected from the group consisting of R D313 and R D314 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D301A and R D302A which do not form a substituted or unsubstituted heterocycle are each independently
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
One or more pairs of adjacent two or more of R D311 to R D321 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R D311 to R D321 which do not form a substituted or unsubstituted heterocycle, do not form a monocycle, and do not form a fused ring are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in formula (D1).
前記式（Ｄ３２）のＲＤ３０１Ａ及びＲＤ３０２Ａは、それぞれ、前記式（Ｄ３）のＲＤ３０１及びＲＤ３０２に対応する。
例えば、ＲＤ３０１ＡとＲＤ３１１が結合して、これらを含む環とａ環に対応するベンゼン環が縮合した２環縮合、３環縮合、４環縮合、又は５環以上縮合の含窒素複素環を形成してもよい。当該含窒素複素環の具体例としては、具体例群Ｇ２のうち、窒素を含む２環以上縮合の複素環基に対応する化合物等が挙げられる。ＲＤ３０１ＡとＲＤ３２１が結合する場合、ＲＤ３０２ＡとＲＤ３１３が結合する場合、及びＲＤ３０２ＡとＲＤ３１４が結合する場合も上記と同じである。 R D301A and R D302A in the formula (D32) correspond to R D301 and R D302 in the formula (D3), respectively.
For example, R D301A and R D311 may be bonded to form a nitrogen-containing heterocycle having two rings, three rings, four rings, or five or more rings, in which a ring containing them is fused with a benzene ring corresponding to the ring a. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing heterocyclic group having two or more rings in specific example group G2. The same applies when R D301A and R D321 are bonded, when R D302A and R D313 are bonded, and when R D302A and R D314 are bonded.
例えば、ＲＤ３０１ＡとＲＤ３１１が結合して、これらを含む環とａ環に対応するベンゼン環が縮合した２環縮合、３環縮合、４環縮合、又は５環以上縮合の含窒素複素環を形成してもよい。当該含窒素複素環の具体例としては、具体例群Ｇ２のうち、窒素を含む２環以上縮合の複素環基に対応する化合物等が挙げられる。ＲＤ３０１ＡとＲＤ３２１が結合する場合、ＲＤ３０２ＡとＲＤ３１３が結合する場合、及びＲＤ３０２ＡとＲＤ３１４が結合する場合も上記と同じである。 R D301A and R D302A in the formula (D32) correspond to R D301 and R D302 in the formula (D3), respectively.
For example, R D301A and R D311 may be bonded to form a nitrogen-containing heterocycle having two rings, three rings, four rings, or five or more rings, in which a ring containing them is fused with a benzene ring corresponding to the ring a. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing heterocyclic group having two or more rings in specific example group G2. The same applies when R D301A and R D321 are bonded, when R D302A and R D313 are bonded, and when R D302A and R D314 are bonded.
一実施形態において、ＲＤ３１１～ＲＤ３２１のうちの隣接する２つ以上からなる組の１組以上は、
互いに結合して、置換もしくは無置換の単環を形成するか、又は
互いに結合して、置換もしくは無置換の縮合環を形成する。
例えば、ＲＤ３１１とＲＤ３１２が結合して、これらが結合する６員環に対して、ベンゼン環、インドール環、ピロール環、ベンゾフラン環、又はベンゾチオフェン環等が縮合した構造を形成してもよい。形成された縮合環は、それぞれ、ナフタレン環、カルバゾール環、インドール環、ベンゾフラン環、ジベンゾフラン環、又はジベンゾチオフェン環となる。 In one embodiment, one or more of the sets of two or more adjacent ones of R D311 to R D321 are
They may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted fused ring.
For example, R and R may be bonded to a 6-membered ring to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed with the 6-membered ring to which they are bonded. The condensed ring thus formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.
互いに結合して、置換もしくは無置換の単環を形成するか、又は
互いに結合して、置換もしくは無置換の縮合環を形成する。
例えば、ＲＤ３１１とＲＤ３１２が結合して、これらが結合する６員環に対して、ベンゼン環、インドール環、ピロール環、ベンゾフラン環、又はベンゾチオフェン環等が縮合した構造を形成してもよい。形成された縮合環は、それぞれ、ナフタレン環、カルバゾール環、インドール環、ベンゾフラン環、ジベンゾフラン環、又はジベンゾチオフェン環となる。 In one embodiment, one or more of the sets of two or more adjacent ones of R D311 to R D321 are
They may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted fused ring.
For example, R and R may be bonded to a 6-membered ring to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed with the 6-membered ring to which they are bonded. The condensed ring thus formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.
一実施形態において、環形成に寄与しないＲＤ３１１～ＲＤ３２１は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D311 to R D321 that do not contribute to ring formation are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D311 to R D321 that do not contribute to ring formation are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
一実施形態において、環形成に寄与しないＲＤ３１１～ＲＤ３２１は、それぞれ独立に、
水素原子、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D311 to R D321 that do not contribute to ring formation are each independently
Hydrogen atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
水素原子、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D311 to R D321 that do not contribute to ring formation are each independently
Hydrogen atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
一実施形態において、環形成に寄与しないＲＤ３１１～ＲＤ３２１は、それぞれ独立に、
水素原子、又は
置換もしくは無置換の炭素数１～５０のアルキル基である。 In one embodiment, R D311 to R D321 that do not contribute to ring formation are each independently
It is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
水素原子、又は
置換もしくは無置換の炭素数１～５０のアルキル基である。 In one embodiment, R D311 to R D321 that do not contribute to ring formation are each independently
It is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
一実施形態において、環形成に寄与しないＲＤ３１１～ＲＤ３２１は、それぞれ独立に、
水素原子、又は
置換もしくは無置換の炭素数１～５０のアルキル基であり、
ＲＤ３１１～ＲＤ３２１のうち少なくとも１つは、置換もしくは無置換の炭素数１～５０のアルキル基である。 In one embodiment, R D311 to R D321 that do not contribute to ring formation are each independently
a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms;
At least one of R D311 to R D321 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
水素原子、又は
置換もしくは無置換の炭素数１～５０のアルキル基であり、
ＲＤ３１１～ＲＤ３２１のうち少なくとも１つは、置換もしくは無置換の炭素数１～５０のアルキル基である。 In one embodiment, R D311 to R D321 that do not contribute to ring formation are each independently
a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms;
At least one of R D311 to R D321 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
一実施形態において、前記式（Ｄ３２）で表される化合物は、下記式（Ｄ３３）で表される化合物である。
（式（Ｄ３３）中、
ＲＤ３３１は、ＲＤ３４６と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３３３は、ＲＤ３４７と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３３４は、ＲＤ３５１と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３４１は、ＲＤ３４２と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３３１～ＲＤ３５１のうちの隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲＤ３３１～ＲＤ３５１は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｒ９０１～Ｒ９０７は、前記式（Ｄ１）で定義した通りである。） In one embodiment, the compound represented by formula (D32) is a compound represented by formula (D33):
(In formula (D33),
R D331 combines with R D346 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D333 combines with R D347 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D334 combines with R D351 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D341 combines with R D342 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
One or more pairs of adjacent two or more of R D331 to R D351 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R D331 to R D351 that are not bonded to each other are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in formula (D1).
ＲＤ３３１は、ＲＤ３４６と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３３３は、ＲＤ３４７と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３３４は、ＲＤ３５１と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３４１は、ＲＤ３４２と結合して、置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成しない。
ＲＤ３３１～ＲＤ３５１のうちの隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲＤ３３１～ＲＤ３５１は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｒ９０１～Ｒ９０７は、前記式（Ｄ１）で定義した通りである。） In one embodiment, the compound represented by formula (D32) is a compound represented by formula (D33):
R D331 combines with R D346 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D333 combines with R D347 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D334 combines with R D351 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
R D341 combines with R D342 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
One or more pairs of adjacent two or more of R D331 to R D351 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R D331 to R D351 that are not bonded to each other are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in formula (D1).
ＲＤ３３１は、ＲＤ３４６と結合して、置換もしくは無置換の複素環を形成してもよい。例えば、ＲＤ３３１とＲＤ３４６が結合して、ＲＤ３４６が結合するベンゼン環と、Ｎを含む環と、ａ環に対応するベンゼン環とが縮合した３環縮合以上の含窒素複素環を形成してもよい。当該含窒素複素環の具体例としては、具体例群Ｇ２のうち、窒素を含む３環縮合以上の複素環基に対応する化合物等が挙げられる。ＲＤ３３３とＲＤ３４７が結合する場合、ＲＤ３３４とＲＤ３５１が結合する場合、及びＲＤ３４１とＲＤ３４２が結合する場合も上記と同じである。
R D331 may be bonded to R D346 to form a substituted or unsubstituted heterocycle. For example, R D331 and R D346 may be bonded to form a nitrogen-containing heterocycle having three or more condensed rings in which the benzene ring to which R D346 is bonded, the ring containing N, and the benzene ring corresponding to the a ring are condensed. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing heterocyclic group having three or more condensed rings in the specific example group G2. The same applies when R D333 and R D347 are bonded, when R D334 and R D351 are bonded, and when R D341 and R D342 are bonded.
一実施形態において、環形成に寄与しないＲＤ３３１～ＲＤ３５１は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D331 to R D351 that do not contribute to ring formation are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D331 to R D351 that do not contribute to ring formation are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
一実施形態において、環形成に寄与しないＲＤ３３１～ＲＤ３５１は、それぞれ独立に、
水素原子、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D331 to R D351 that do not contribute to ring formation are each independently
Hydrogen atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
水素原子、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。 In one embodiment, R D331 to R D351 that do not contribute to ring formation are each independently
Hydrogen atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
一実施形態において、環形成に寄与しないＲＤ３３１～ＲＤ３５１は、それぞれ独立に、
水素原子、又は
置換もしくは無置換の炭素数１～５０のアルキル基である。 In one embodiment, R D331 to R D351 that do not contribute to ring formation are each independently
It is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
水素原子、又は
置換もしくは無置換の炭素数１～５０のアルキル基である。 In one embodiment, R D331 to R D351 that do not contribute to ring formation are each independently
It is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
一実施形態において、環形成に寄与しないＲＤ３３１～ＲＤ３５１は、それぞれ独立に、
水素原子、又は
置換もしくは無置換の炭素数１～５０のアルキル基であり、
ＲＤ３３１～ＲＤ３５１のうち少なくとも１つは置換もしくは無置換の炭素数１～５０のアルキル基である。 In one embodiment, R D331 to R D351 that do not contribute to ring formation are each independently
a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms;
At least one of R D331 to R D351 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
水素原子、又は
置換もしくは無置換の炭素数１～５０のアルキル基であり、
ＲＤ３３１～ＲＤ３５１のうち少なくとも１つは置換もしくは無置換の炭素数１～５０のアルキル基である。 In one embodiment, R D331 to R D351 that do not contribute to ring formation are each independently
a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms;
At least one of R D331 to R D351 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
一実施形態において、前記式（Ｄ３３）で表される化合物は、下記式（Ｄ３３Ａ）で表される化合物である。
In one embodiment, the compound represented by formula (D33) is a compound represented by formula (D33A):
（式（Ｄ３３Ａ）中、
ＲＤ３６１は、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。
ＲＤ３６２～ＲＤ３６５は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。） (In formula (D33A),
R D361 is
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R D362 to R D365 each independently represent
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
ＲＤ３６１は、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。
ＲＤ３６２～ＲＤ３６５は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。） (In formula (D33A),
R D361 is
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R D362 to R D365 each independently represent
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
一実施形態において、ＲＤ３６１～ＲＤ３６５は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, R D361 to R D365 are each independently:
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
置換もしくは無置換の炭素数１～５０のアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, R D361 to R D365 are each independently:
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
一実施形態において、ＲＤ３６１～ＲＤ３６５は、それぞれ独立に、置換もしくは無置換の炭素数１～５０のアルキル基である。
In one embodiment, R D361 to R D365 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
一実施形態において、前記式（Ｄ３３）で表される化合物は、下記式（Ｄ３３Ｂ）で表される化合物である。
In one embodiment, the compound represented by formula (D33) is a compound represented by formula (D33B):
ＲＤ３７１及びＲＤ３７２は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｎ（Ｒ９０６）（Ｒ９０７）、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。
ＲＤ３７３～ＲＤ３７５は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｎ（Ｒ９０６）（Ｒ９０７）、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。
Ｒ９０６及びＲ９０７は、前記式（Ｄ１）で定義した通りである。）
R D371 and R D372 are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R D373 to R D375 each independently represent
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R 906 and R 907 are as defined in formula (D1).
一実施形態において、前記式（Ｄ３３）で表される化合物は、下記式（Ｄ３３Ｂ’）で表される化合物である。
In one embodiment, the compound represented by formula (D33) is a compound represented by the following formula (D33B'):
一実施形態において、ＲＤ３７１～ＲＤ３７５のうち少なくとも１つは、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｎ（Ｒ９０６）（Ｒ９０７）、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, at least one of R D371 to R D375 is
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｎ（Ｒ９０６）（Ｒ９０７）、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, at least one of R D371 to R D375 is
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
一実施形態において、ＲＤ３７２は、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
－Ｎ（Ｒ９０６）（Ｒ９０７）、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基であり、
ＲＤ３７１及びＲＤ３７３～ＲＤ３７５は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
－Ｎ（Ｒ９０６）（Ｒ９０７）、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, RD372 is
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
-N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
R D371 and R D373 to R D375 each independently represent
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
-N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
－Ｎ（Ｒ９０６）（Ｒ９０７）、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基であり、
ＲＤ３７１及びＲＤ３７３～ＲＤ３７５は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
－Ｎ（Ｒ９０６）（Ｒ９０７）、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, RD372 is
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
-N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
R D371 and R D373 to R D375 each independently represent
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
-N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
一実施形態において、前記式（Ｄ３３）で表される化合物は、下記式（Ｄ３３Ｃ）で表される化合物である。
In one embodiment, the compound represented by formula (D33) is a compound represented by formula (D33C):
ＲＤ３８１及びＲＤ３８２は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。
ＲＤ３８３～ＲＤ３８６は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。）
R and R are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R D383 to R D386 are each independently
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
一実施形態において、前記式（Ｄ３３）で表される化合物は、下記式（Ｄ３３Ｃ’）で表される化合物である。
In one embodiment, the compound represented by formula (D33) is a compound represented by the following formula (D33C'):
（式（Ｄ３３Ｃ’）中、ＲＤ３８３～ＲＤ３８６は、前記式（Ｄ３３Ｃ）で定義した通りである。）
(In formula (D33C'), R D383 to R D386 are as defined in formula (D33C) above.)
一実施形態において、ＲＤ３８１～ＲＤ３８６は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, R D381 to R D386 are each independently:
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
置換もしくは無置換の炭素数１～５０のアルキル基、又は
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, R D381 to R D386 are each independently:
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
一実施形態において、ＲＤ３８１～ＲＤ３８６は、それぞれ独立に、置換もしくは無置換の環形成炭素数６～５０のアリール基である。
In one embodiment, R D381 to R D386 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
前記式（Ｄ３）で表される化合物は、まずａ環、ｂ環、及びｃ環を第１の連結基（Ｎ－ＲＤ３０１を含む基及びＮ－ＲＤ３０２を含む基）で結合させることで中間体を製造し（第１反応）、ａ環、ｂ環、及びｃ環を第２の連結基（ホウ素原子を含む基）で結合させることで最終生成物を製造することができる（第２反応）。第１反応ではバッハブルト－ハートウィッグ反応等のアミノ化反応を適用できる。第２反応では、タンデムヘテロフリーデルクラフツ反応等を適用できる。
The compound represented by formula (D3) can be produced by first linking ring a, ring b, and ring c with a first linking group (a group containing N-R D301 and a group containing N-R D302 ) to produce an intermediate (first reaction), and then linking ring a, ring b, and ring c with a second linking group (a group containing a boron atom) to produce a final product (second reaction). In the first reaction, an amination reaction such as the Bachbult-Hartwig reaction can be applied. In the second reaction, a tandem hetero Friedel-Crafts reaction or the like can be applied.
式（Ｄ３）で表される化合物は、目的物に合わせた既知の反応や原料を用いることで合成することができる。
The compound represented by formula (D3) can be synthesized by using known reactions and raw materials that are suited to the target product.
式（Ｄ３）で表される化合物の具体例としては、以下の化合物が挙げられる。これらは例示に過ぎず、式（Ｄ３）で表される化合物は下記具体例に限定されるものではない。
Specific examples of compounds represented by formula (D3) include the following compounds. These are merely examples, and compounds represented by formula (D3) are not limited to the following specific examples.
（式（Ｄ４）で表される化合物）
式（Ｄ４）で表される化合物について説明する。 (Compound represented by formula (D4))
The compound represented by formula (D4) will be described.
式（Ｄ４）で表される化合物について説明する。 (Compound represented by formula (D4))
The compound represented by formula (D4) will be described.
（式（Ｄ４）中、
ＲＤ４０１とＲＤ４０２の組、ＲＤ４０２とＲＤ４０３の組、及びＲＤ４０３とＲＤ４０４の組のうち少なくとも一組は、互いに結合して下記式（Ｄ４２）で示される２価の基を形成する。
ＲＤ４０５とＲＤ４０６の組、ＲＤ４０６とＲＤ４０７の組、及びＲＤ４０７とＲＤ４０８の組のうち少なくとも一組は、互いに結合して下記式（Ｄ４３）で示される２価の基を形成する。
前記式（Ｄ４２）で示される２価の基を形成しないＲＤ４０１～ＲＤ４０４及びＲＤ４１１～ＲＤ４１４の少なくとも１つは、下記式（Ｄ４４）で表される１価の基である。
前記式（Ｄ４３）で示される２価の基を形成しないＲＤ４０５～ＲＤ４０８及びＲＤ４２１～ＲＤ４２４の少なくとも１つは、下記式（Ｄ４４）で表される１価の基である。
ＸＤ４は、酸素原子、硫黄原子、又はＮＲＤ４０９である。
前記式（Ｄ４２）及び式（Ｄ４３）で表される２価の基を形成せず、かつ、前記式（Ｄ４４）で表される１価の基ではないＲＤ４０１～ＲＤ４０８、前記式（Ｄ４４）で表される１価の基ではないＲＤ４１１～ＲＤ４１４及びＲＤ４２１～ＲＤ４２４、並びにＲＤ４０９は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の複素環基である。
(In formula (D4),
At least one pair of R D401 and R D402 , R D402 and R D403 , and R D403 and R D404 are bonded to each other to form a divalent group represented by the following formula (D42).
At least one pair of R D405 and R D406 , R D406 and R D407 , and R D407 and R D408 are bonded to each other to form a divalent group represented by the following formula (D43).
At least one of R D401 to R D404 and R D411 to R D414 that do not form a divalent group represented by formula (D42) is a monovalent group represented by formula (D44) below.
At least one of R D405 to R D408 and R D421 to R D424 that do not form a divalent group represented by formula (D43) is a monovalent group represented by formula (D44) below.
XD4 is an oxygen atom, a sulfur atom, or NR D409 .
R D401 to R D408 which do not form a divalent group represented by formula (D42) or formula (D43) and are not a monovalent group represented by formula (D44), R D411 to R D414 and R D421 to R D424 which are not a monovalent group represented by formula (D44), and R D409 are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
ＲＤ４０１とＲＤ４０２の組、ＲＤ４０２とＲＤ４０３の組、及びＲＤ４０３とＲＤ４０４の組のうち少なくとも一組は、互いに結合して下記式（Ｄ４２）で示される２価の基を形成する。
ＲＤ４０５とＲＤ４０６の組、ＲＤ４０６とＲＤ４０７の組、及びＲＤ４０７とＲＤ４０８の組のうち少なくとも一組は、互いに結合して下記式（Ｄ４３）で示される２価の基を形成する。
前記式（Ｄ４３）で示される２価の基を形成しないＲＤ４０５～ＲＤ４０８及びＲＤ４２１～ＲＤ４２４の少なくとも１つは、下記式（Ｄ４４）で表される１価の基である。
ＸＤ４は、酸素原子、硫黄原子、又はＮＲＤ４０９である。
前記式（Ｄ４２）及び式（Ｄ４３）で表される２価の基を形成せず、かつ、前記式（Ｄ４４）で表される１価の基ではないＲＤ４０１～ＲＤ４０８、前記式（Ｄ４４）で表される１価の基ではないＲＤ４１１～ＲＤ４１４及びＲＤ４２１～ＲＤ４２４、並びにＲＤ４０９は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の複素環基である。
At least one pair of R D401 and R D402 , R D402 and R D403 , and R D403 and R D404 are bonded to each other to form a divalent group represented by the following formula (D42).
At least one pair of R D405 and R D406 , R D406 and R D407 , and R D407 and R D408 are bonded to each other to form a divalent group represented by the following formula (D43).
At least one of R D405 to R D408 and R D421 to R D424 that do not form a divalent group represented by formula (D43) is a monovalent group represented by formula (D44) below.
XD4 is an oxygen atom, a sulfur atom, or NR D409 .
R D401 to R D408 which do not form a divalent group represented by formula (D42) or formula (D43) and are not a monovalent group represented by formula (D44), R D411 to R D414 and R D421 to R D424 which are not a monovalent group represented by formula (D44), and R D409 are each independently
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atoms, cyano groups, nitro groups,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
式（Ｄ４４）中、
ＡｒＤ４０１及びＡｒＤ４０２は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
ＬＤ４０１～ＬＤ４０３は、それぞれ独立に、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、
置換もしくは無置換の環形成原子数５～３０の２価の複素環基、又は
置換もしくは無置換の環形成炭素数６～３０のアリーレン基及び置換もしくは無置換の環形成原子数５～３０の２価の複素環基からなる群から選択される２～４個の基が結合して形成される２価の連結基である。
ＬＤ４０１は、前記式（Ｄ４）で表される環構造、式（Ｄ４２）で表される基、又は式（Ｄ４３）で表される基に結合する。） In formula (D44),
Ar D401 and Ar D402 are each independently
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L D401 to L D403 each independently represent
Single bond,
a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,
The divalent linking group is formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
L D401 is bonded to the ring structure represented by formula (D4), the group represented by formula (D42), or the group represented by formula (D43).
ＡｒＤ４０１及びＡｒＤ４０２は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
ＬＤ４０１～ＬＤ４０３は、それぞれ独立に、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、
置換もしくは無置換の環形成原子数５～３０の２価の複素環基、又は
置換もしくは無置換の環形成炭素数６～３０のアリーレン基及び置換もしくは無置換の環形成原子数５～３０の２価の複素環基からなる群から選択される２～４個の基が結合して形成される２価の連結基である。
ＬＤ４０１は、前記式（Ｄ４）で表される環構造、式（Ｄ４２）で表される基、又は式（Ｄ４３）で表される基に結合する。） In formula (D44),
Ar D401 and Ar D402 are each independently
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L D401 to L D403 each independently represent
Single bond,
a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,
The divalent linking group is formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
L D401 is bonded to the ring structure represented by formula (D4), the group represented by formula (D42), or the group represented by formula (D43).
前記式（Ｄ４）において、前記式（Ｄ４２）で示される２価の基及び式（Ｄ４３）で示される２価の基が形成される位置は特に限定されず、ＲＤ４０１～ＲＤ４０８の可能な位置において当該基を形成し得る。
In the formula (D4), the positions at which the divalent group represented by the formula (D42) and the divalent group represented by the formula (D43) are formed are not particularly limited, and the groups can be formed at any possible position of R D401 to R D408 .
式（Ｄ４）で表される化合物は、目的物に合わせた既知の反応や原料を用いることで合成することができる。
The compound represented by formula (D4) can be synthesized by using known reactions and raw materials that are suited to the target product.
前記式（Ｄ４）で表される化合物としては、国際公開第２０１４／１０４１４４号に記載の化合物の他、例えば、以下に示す化合物が具体例として挙げられる。これらは例示に過ぎず、式（Ｄ４）で表される化合物は下記具体例に限定されるものではない。
Specific examples of the compound represented by formula (D4) include the compounds described in WO 2014/104144, as well as the compounds shown below. These are merely examples, and the compound represented by formula (D4) is not limited to the specific examples below.
上述した式（Ｄ１）、式（Ｄ２）、式（Ｄ３）、及び式（Ｄ４）で表される化合物以外にも、例えば以下に示す化合物を第２の化合物として使用することができる。
In addition to the compounds represented by the above-mentioned formulas (D1), (D2), (D3), and (D4), for example, the compounds shown below can be used as the second compound.
一実施形態において、第１の発光層はホスト材料（マトリックス材料と称する場合もある。）として、上記式（３）で表される化合物を含む。
一実施形態において、第１の発光層はさらにドーパント材料を含む。
一実施形態において、第１の発光層はドーパント材料（ゲスト材料、エミッター、又は発光材料と称する場合もある。）として、上記第２の化合物を含む。 In one embodiment, the first light-emitting layer contains the compound represented by the above formula (3) as a host material (sometimes referred to as a matrix material).
In one embodiment, the first light-emitting layer further comprises a dopant material.
In one embodiment, the first light-emitting layer includes the second compound as a dopant material (also sometimes referred to as a guest material, an emitter, or an emissive material).
一実施形態において、第１の発光層はさらにドーパント材料を含む。
一実施形態において、第１の発光層はドーパント材料（ゲスト材料、エミッター、又は発光材料と称する場合もある。）として、上記第２の化合物を含む。 In one embodiment, the first light-emitting layer contains the compound represented by the above formula (3) as a host material (sometimes referred to as a matrix material).
In one embodiment, the first light-emitting layer further comprises a dopant material.
In one embodiment, the first light-emitting layer includes the second compound as a dopant material (also sometimes referred to as a guest material, an emitter, or an emissive material).
一実施形態において、第１の発光層はドーパント材料を、第１の発光層の全質量の１．１質量％を超えて、１．２質量％以上、又は１．５質量％以上、含有する。
一実施形態において、第１の発光層はドーパント材料を、第１の発光層の全質量の１０質量％以下、７質量％以下、又は５質量％以下、含有する。 In one embodiment, the first light-emitting layer contains more than 1.1 weight percent, 1.2 weight percent or more, or 1.5 weight percent or more of the dopant material based on the total weight of the first light-emitting layer.
In one embodiment, the first light-emitting layer contains no more than 10 weight percent, no more than 7 weight percent, or no more than 5 weight percent of the dopant material based on the total weight of the first light-emitting layer.
一実施形態において、第１の発光層はドーパント材料を、第１の発光層の全質量の１０質量％以下、７質量％以下、又は５質量％以下、含有する。 In one embodiment, the first light-emitting layer contains more than 1.1 weight percent, 1.2 weight percent or more, or 1.5 weight percent or more of the dopant material based on the total weight of the first light-emitting layer.
In one embodiment, the first light-emitting layer contains no more than 10 weight percent, no more than 7 weight percent, or no more than 5 weight percent of the dopant material based on the total weight of the first light-emitting layer.
一実施形態において、第１の発光層はホスト材料を、第１の発光層の全質量の６０質量％以上、７０質量％以上、８０質量％以上、９０質量％以上、又は９５質量％以上、含有する。
一実施形態において、第１の発光層はホスト材料を、第１の発光層の全質量の９９質量％以下、含有する。 In one embodiment, the first light-emitting layer contains 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more of the host material based on the total weight of the first light-emitting layer.
In one embodiment, the first light-emitting layer contains a host material in an amount of up to 99% by weight of the total weight of the first light-emitting layer.
一実施形態において、第１の発光層はホスト材料を、第１の発光層の全質量の９９質量％以下、含有する。 In one embodiment, the first light-emitting layer contains 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more of the host material based on the total weight of the first light-emitting layer.
In one embodiment, the first light-emitting layer contains a host material in an amount of up to 99% by weight of the total weight of the first light-emitting layer.
第１の発光層に、ホスト材料とドーパント材料以外の材料が含まれていてもよい。
The first light-emitting layer may contain materials other than the host material and the dopant material.
第１の発光層は、ホスト材料を１種のみ含んでもよいし、２種以上含んでもよい。第１の発光層は、ドーパント材料を１種のみ含んでもよいし、２種以上含んでもよい。
The first light-emitting layer may contain only one type of host material, or may contain two or more types. The first light-emitting layer may contain only one type of dopant material, or may contain two or more types.
（第２の発光層）
第２の発光層は、上述した第１の発光層とは異なる化合物を少なくとも1種含む。一実施形態において、第２の発光層はホスト材料を含む。ホスト材料としては、上述した式（３）で表される化合物の他、例えば、１）アルミニウム錯体、ベリリウム錯体、若しくは亜鉛錯体等の金属錯体、２）オキサジアゾール誘導体、ベンゾイミダゾール誘導体、若しくはフェナントロリン誘導体等の複素環化合物、３）カルバゾール誘導体、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、若しくはクリセン誘導体等の縮合芳香族化合物、４）トリアリールアミン誘導体、若しくは縮合多環芳香族アミン誘導体等の芳香族アミン化合物を用いることができる。
一実施形態において、第２のホスト材料は、第１の発光層が含有する第１のホスト材料とは、異なる化合物である。 (Second Light-Emitting Layer)
The second light-emitting layer contains at least one compound different from the first light-emitting layer. In one embodiment, the second light-emitting layer contains a host material. As the host material, in addition to the compound represented by the above formula (3), for example, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative, or 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative can be used.
In one embodiment, the second host material is a different compound than the first host material contained in the first light-emitting layer.
第２の発光層は、上述した第１の発光層とは異なる化合物を少なくとも1種含む。一実施形態において、第２の発光層はホスト材料を含む。ホスト材料としては、上述した式（３）で表される化合物の他、例えば、１）アルミニウム錯体、ベリリウム錯体、若しくは亜鉛錯体等の金属錯体、２）オキサジアゾール誘導体、ベンゾイミダゾール誘導体、若しくはフェナントロリン誘導体等の複素環化合物、３）カルバゾール誘導体、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、若しくはクリセン誘導体等の縮合芳香族化合物、４）トリアリールアミン誘導体、若しくは縮合多環芳香族アミン誘導体等の芳香族アミン化合物を用いることができる。
一実施形態において、第２のホスト材料は、第１の発光層が含有する第１のホスト材料とは、異なる化合物である。 (Second Light-Emitting Layer)
The second light-emitting layer contains at least one compound different from the first light-emitting layer. In one embodiment, the second light-emitting layer contains a host material. As the host material, in addition to the compound represented by the above formula (3), for example, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative, or 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative can be used.
In one embodiment, the second host material is a different compound than the first host material contained in the first light-emitting layer.
一実施形態において、第２の発光層はさらにドーパント材料を含む。ドーパント材料としては、例えば、上述した第２の化合物を用いることができる。また、ドーパント材料として公知の燐光発光性材料を用いることもできる。
一実施形態において、第２の発光層のドーパント材料は、第１の発光層のドーパント材料とは、異なる化合物である。
一実施形態において、第２の発光層のドーパント材料は、第１の発光層のドーパント材料と、同じ化合物である。 In one embodiment, the second light-emitting layer further includes a dopant material. As the dopant material, for example, the second compound described above can be used. In addition, a known phosphorescent material can also be used as the dopant material.
In one embodiment, the dopant material of the second light-emitting layer is a different compound than the dopant material of the first light-emitting layer.
In one embodiment, the dopant material of the second light-emitting layer is the same compound as the dopant material of the first light-emitting layer.
一実施形態において、第２の発光層のドーパント材料は、第１の発光層のドーパント材料とは、異なる化合物である。
一実施形態において、第２の発光層のドーパント材料は、第１の発光層のドーパント材料と、同じ化合物である。 In one embodiment, the second light-emitting layer further includes a dopant material. As the dopant material, for example, the second compound described above can be used. In addition, a known phosphorescent material can also be used as the dopant material.
In one embodiment, the dopant material of the second light-emitting layer is a different compound than the dopant material of the first light-emitting layer.
In one embodiment, the dopant material of the second light-emitting layer is the same compound as the dopant material of the first light-emitting layer.
一実施形態において、第２の発光層はドーパント材料を、第２の発光層の全質量の１．１質量％を超えて、１．２質量％以上、又は１．５質量％以上、含有する。
一実施形態において、第２の発光層はドーパント材料を、第２の発光層の全質量の１０質量％以下、７質量％以下、又は５質量％以下、含有する。 In one embodiment, the second light-emitting layer contains more than 1.1 weight percent, 1.2 weight percent or more, or 1.5 weight percent or more of the dopant material based on the total weight of the second light-emitting layer.
In one embodiment, the second light-emitting layer contains no more than 10 weight percent, no more than 7 weight percent, or no more than 5 weight percent of the dopant material based on the total weight of the second light-emitting layer.
一実施形態において、第２の発光層はドーパント材料を、第２の発光層の全質量の１０質量％以下、７質量％以下、又は５質量％以下、含有する。 In one embodiment, the second light-emitting layer contains more than 1.1 weight percent, 1.2 weight percent or more, or 1.5 weight percent or more of the dopant material based on the total weight of the second light-emitting layer.
In one embodiment, the second light-emitting layer contains no more than 10 weight percent, no more than 7 weight percent, or no more than 5 weight percent of the dopant material based on the total weight of the second light-emitting layer.
一実施形態において、第２の発光層はホスト材料を、第２の発光層の全質量の６０質量％以上、７０質量％以上、８０質量％以上、９０質量％以上、又は９５質量％以上、含有する。
一実施形態において、第２の発光層はホスト材料を、第２の発光層の全質量の９９質量％以下、含有する。 In one embodiment, the second light-emitting layer contains 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more of the host material based on the total weight of the second light-emitting layer.
In one embodiment, the second light-emitting layer contains a host material in an amount of up to 99% by weight of the total weight of the second light-emitting layer.
一実施形態において、第２の発光層はホスト材料を、第２の発光層の全質量の９９質量％以下、含有する。 In one embodiment, the second light-emitting layer contains 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more of the host material based on the total weight of the second light-emitting layer.
In one embodiment, the second light-emitting layer contains a host material in an amount of up to 99% by weight of the total weight of the second light-emitting layer.
第２の発光層に、ホスト材料とドーパント材料以外の材料が含まれていてもよい。
The second light-emitting layer may contain materials other than the host material and the dopant material.
第２の発光層はホスト材料を１種のみ含んでもよいし、２種以上含んでもよい。第２の発光層はドーパント材料を１種のみ含んでもよいし、２種以上含んでもよい。
The second light-emitting layer may contain only one type of host material, or may contain two or more types. The second light-emitting layer may contain only one type of dopant material, or may contain two or more types.
第２の発光層は、蛍光発光型の発光層であっても、燐光発光型の発光層であってもよい。
一実施形態において、第２の発光層は、蛍光発光型の発光層である。 The second light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer.
In one embodiment, the second light-emitting layer is a fluorescent-type light-emitting layer.
一実施形態において、第２の発光層は、蛍光発光型の発光層である。 The second light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer.
In one embodiment, the second light-emitting layer is a fluorescent-type light-emitting layer.
本発明の一態様に係る有機ＥＬ素子は、第１の発光層が、式（３）で表される化合物を含有する以外は、本発明の効果を損なわない限りにおいて、従来公知の材料、素子構成を適用することができる。
In the organic EL element according to one embodiment of the present invention, conventionally known materials and element configurations can be applied, so long as the effects of the present invention are not impaired, except that the first light-emitting layer contains the compound represented by formula (3).
（基板）
基板は、発光素子の支持体として用いられる。基板としては、例えば、ガラス、石英、プラスチック等を用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる（フレキシブル）基板のことであり、例えば、ポリカーボネート、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。 (substrate)
The substrate is used as a support for the light-emitting element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples of the flexible substrate include plastic substrates made of polycarbonate and polyvinyl chloride.
基板は、発光素子の支持体として用いられる。基板としては、例えば、ガラス、石英、プラスチック等を用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる（フレキシブル）基板のことであり、例えば、ポリカーボネート、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。 (substrate)
The substrate is used as a support for the light-emitting element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples of the flexible substrate include plastic substrates made of polycarbonate and polyvinyl chloride.
（陽極）
基板上に形成される陽極には、仕事関数の大きい（具体的には４．０ｅＶ以上）金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。具体的には、例えば、酸化インジウム－酸化スズ（ＩＴＯ：Ｉｎｄｉｕｍ Ｔｉｎ Ｏｘｉｄｅ）、珪素若しくは酸化珪素を含有した酸化インジウム－酸化スズ、酸化インジウム－酸化亜鉛、酸化タングステン、酸化亜鉛を含有した酸化インジウム、及びグラフェン等が挙げられる。この他、金（Ａｕ）、白金（Ｐｔ）、又は金属材料の窒化物（例えば、窒化チタン）等が挙げられる。 (anode)
For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride).
基板上に形成される陽極には、仕事関数の大きい（具体的には４．０ｅＶ以上）金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。具体的には、例えば、酸化インジウム－酸化スズ（ＩＴＯ：Ｉｎｄｉｕｍ Ｔｉｎ Ｏｘｉｄｅ）、珪素若しくは酸化珪素を含有した酸化インジウム－酸化スズ、酸化インジウム－酸化亜鉛、酸化タングステン、酸化亜鉛を含有した酸化インジウム、及びグラフェン等が挙げられる。この他、金（Ａｕ）、白金（Ｐｔ）、又は金属材料の窒化物（例えば、窒化チタン）等が挙げられる。 (anode)
For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride).
（正孔注入層）
正孔注入層は、正孔注入性の高い物質を含む層である。正孔注入性の高い物質としては、モリブデン酸化物、チタン酸化物、バナジウム酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、タンタル酸化物、銀酸化物、タングステン酸化物、マンガン酸化物、芳香族アミン化合物、又は高分子化合物（オリゴマー、デンドリマー、ポリマー等）等も使用できる。 (Hole Injection Layer)
The hole injection layer is a layer containing a substance having a high hole injection property. Examples of the substance having a high hole injection property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, and polymer compounds (oligomers, dendrimers, polymers, etc.).
正孔注入層は、正孔注入性の高い物質を含む層である。正孔注入性の高い物質としては、モリブデン酸化物、チタン酸化物、バナジウム酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、タンタル酸化物、銀酸化物、タングステン酸化物、マンガン酸化物、芳香族アミン化合物、又は高分子化合物（オリゴマー、デンドリマー、ポリマー等）等も使用できる。 (Hole Injection Layer)
The hole injection layer is a layer containing a substance having a high hole injection property. Examples of the substance having a high hole injection property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, and polymer compounds (oligomers, dendrimers, polymers, etc.).
（正孔輸送層）
正孔輸送層は、正孔輸送性の高い物質を含む層である。正孔輸送層には、芳香族アミン化合物、カルバゾール誘導体、アントラセン誘導体等を使用する事ができる。ポリ（Ｎ－ビニルカルバゾール）（略称：ＰＶＫ）やポリ（４－ビニルトリフェニルアミン）（略称：ＰＶＴＰＡ）等の高分子化合物を用いることもできる。但し、電子よりも正孔の輸送性の高い物質であれば、これら以外のものを用いてもよい。尚、正孔輸送性の高い物質を含む層は、単層のものだけでなく、上記物質からなる層が二層以上積層したものとしてもよい。 (Hole transport layer)
The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, other substances may be used as long as they have a higher hole transport property than electron transport properties. The layer containing the substance with high hole transport properties may be not only a single layer, but also a laminate of two or more layers made of the above substances.
正孔輸送層は、正孔輸送性の高い物質を含む層である。正孔輸送層には、芳香族アミン化合物、カルバゾール誘導体、アントラセン誘導体等を使用する事ができる。ポリ（Ｎ－ビニルカルバゾール）（略称：ＰＶＫ）やポリ（４－ビニルトリフェニルアミン）（略称：ＰＶＴＰＡ）等の高分子化合物を用いることもできる。但し、電子よりも正孔の輸送性の高い物質であれば、これら以外のものを用いてもよい。尚、正孔輸送性の高い物質を含む層は、単層のものだけでなく、上記物質からなる層が二層以上積層したものとしてもよい。 (Hole transport layer)
The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, other substances may be used as long as they have a higher hole transport property than electron transport properties. The layer containing the substance with high hole transport properties may be not only a single layer, but also a laminate of two or more layers made of the above substances.
（発光層のゲスト（ドーパント）材料）
発光層は、発光性の高い物質を含む層であり、種々の材料を用いることができる。例えば、発光性の高い物質としては、式（Ｄ１）で表される化合物、式（Ｄ２）で表される化合物、式（Ｄ３）で表される化合物、及び式（Ｄ４）で表される化合物の他、蛍光を発光する蛍光性化合物や燐光を発光する燐光性化合物を用いることができる。蛍光性化合物は一重項励起状態から発光可能な化合物であり、燐光性化合物は三重項励起状態から発光可能な化合物である。
発光層に用いることができる青色系の蛍光発光材料として、ピレン誘導体、スチリルアミン誘導体、クリセン誘導体、フルオランテン誘導体、フルオレン誘導体、ジアミン誘導体、トリアリールアミン誘導体等が使用できる。発光層に用いることができる緑色系の蛍光発光材料として、芳香族アミン誘導体等を使用できる。発光層に用いることができる赤色系の蛍光発光材料として、テトラセン誘導体、ジアミン誘導体等が使用できる。
発光層に用いることができる青色系の燐光発光材料として、イリジウム錯体、オスミウム錯体、白金錯体等の金属錯体が使用される。発光層に用いることができる緑色系の燐光発光材料としてイリジウム錯体等が使用される。発光層に用いることができる赤色系の燐光発光材料として、イリジウム錯体、白金錯体、テルビウム錯体、ユーロピウム錯体等の金属錯体が使用される。 (Guest (dopant) material in the emitting layer)
The light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used. For example, as the highly light-emitting substance, a compound represented by formula (D1), a compound represented by formula (D2), a compound represented by formula (D3), and a compound represented by formula (D4), as well as a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.
Examples of blue-based fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Examples of green-based fluorescent materials that can be used in the light-emitting layer include aromatic amine derivatives. Examples of red-based fluorescent materials that can be used in the light-emitting layer include tetracene derivatives and diamine derivatives.
As blue phosphorescent materials usable in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, platinum complexes, etc. are used. As green phosphorescent materials usable in the light-emitting layer, iridium complexes, etc. are used. As red phosphorescent materials usable in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, europium complexes, etc. are used.
発光層は、発光性の高い物質を含む層であり、種々の材料を用いることができる。例えば、発光性の高い物質としては、式（Ｄ１）で表される化合物、式（Ｄ２）で表される化合物、式（Ｄ３）で表される化合物、及び式（Ｄ４）で表される化合物の他、蛍光を発光する蛍光性化合物や燐光を発光する燐光性化合物を用いることができる。蛍光性化合物は一重項励起状態から発光可能な化合物であり、燐光性化合物は三重項励起状態から発光可能な化合物である。
発光層に用いることができる青色系の蛍光発光材料として、ピレン誘導体、スチリルアミン誘導体、クリセン誘導体、フルオランテン誘導体、フルオレン誘導体、ジアミン誘導体、トリアリールアミン誘導体等が使用できる。発光層に用いることができる緑色系の蛍光発光材料として、芳香族アミン誘導体等を使用できる。発光層に用いることができる赤色系の蛍光発光材料として、テトラセン誘導体、ジアミン誘導体等が使用できる。
発光層に用いることができる青色系の燐光発光材料として、イリジウム錯体、オスミウム錯体、白金錯体等の金属錯体が使用される。発光層に用いることができる緑色系の燐光発光材料としてイリジウム錯体等が使用される。発光層に用いることができる赤色系の燐光発光材料として、イリジウム錯体、白金錯体、テルビウム錯体、ユーロピウム錯体等の金属錯体が使用される。 (Guest (dopant) material in the emitting layer)
The light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used. For example, as the highly light-emitting substance, a compound represented by formula (D1), a compound represented by formula (D2), a compound represented by formula (D3), and a compound represented by formula (D4), as well as a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.
Examples of blue-based fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Examples of green-based fluorescent materials that can be used in the light-emitting layer include aromatic amine derivatives. Examples of red-based fluorescent materials that can be used in the light-emitting layer include tetracene derivatives and diamine derivatives.
As blue phosphorescent materials usable in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, platinum complexes, etc. are used. As green phosphorescent materials usable in the light-emitting layer, iridium complexes, etc. are used. As red phosphorescent materials usable in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, europium complexes, etc. are used.
（発光層のホスト材料）
発光層としては、上述した発光性の高い物質（ゲスト材料）を他の物質（ホスト材料）に分散させた構成としてもよい。発光性の高い物質を分散させるための物質としては、上記で説明した本発明で用いる材料（式（１）で表される化合物、式（２）で表される化合物、及び式（３）で表される化合物）の他、各種のものを用いることができ、発光性の高い物質よりも最低空軌道準位（ＬＵＭＯ準位）が高く、最高被占有軌道準位（ＨＯＭＯ準位）が低い物質を用いることが好ましい。
発光性の高い物質を分散させるための物質（ホスト材料）としては、１）アルミニウム錯体、ベリリウム錯体、若しくは亜鉛錯体等の金属錯体、２）オキサジアゾール誘導体、ベンゾイミダゾール誘導体、若しくはフェナントロリン誘導体等の複素環化合物、３）カルバゾール誘導体、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、若しくはクリセン誘導体等の縮合芳香族化合物、４）トリアリールアミン誘導体、若しくは縮合多環芳香族アミン誘導体等の芳香族アミン化合物が使用される。
また、ホスト材料として遅延蛍光性（熱活性化遅延蛍光性）の化合物を用いることもできる。発光層が、上記で説明した本発明で用いる材料と、遅延蛍光性のホスト化合物と、を含むことも好ましい。
発光層は、上記で説明した本発明で用いる材料に加えて、上記の他の物質を含んでもよいし、含まなくてもよい。 (Host material of the light-emitting layer)
The light-emitting layer may have a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material). As a substance for dispersing the highly luminescent substance, various substances can be used in addition to the above-described materials used in the present invention (the compound represented by formula (1), the compound represented by formula (2), and the compound represented by formula (3)). It is preferable to use a substance having a lower lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the highly luminescent substance.
As a substance (host material) for dispersing a highly luminescent substance, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative; or 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative.
In addition, a delayed fluorescent (thermally activated delayed fluorescent) compound can be used as the host material. It is also preferable that the light-emitting layer contains the material used in the present invention described above and a delayed fluorescent host compound.
The light-emitting layer may or may not contain the above-mentioned other substances in addition to the materials used in the present invention described above.
発光層としては、上述した発光性の高い物質（ゲスト材料）を他の物質（ホスト材料）に分散させた構成としてもよい。発光性の高い物質を分散させるための物質としては、上記で説明した本発明で用いる材料（式（１）で表される化合物、式（２）で表される化合物、及び式（３）で表される化合物）の他、各種のものを用いることができ、発光性の高い物質よりも最低空軌道準位（ＬＵＭＯ準位）が高く、最高被占有軌道準位（ＨＯＭＯ準位）が低い物質を用いることが好ましい。
発光性の高い物質を分散させるための物質（ホスト材料）としては、１）アルミニウム錯体、ベリリウム錯体、若しくは亜鉛錯体等の金属錯体、２）オキサジアゾール誘導体、ベンゾイミダゾール誘導体、若しくはフェナントロリン誘導体等の複素環化合物、３）カルバゾール誘導体、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、若しくはクリセン誘導体等の縮合芳香族化合物、４）トリアリールアミン誘導体、若しくは縮合多環芳香族アミン誘導体等の芳香族アミン化合物が使用される。
また、ホスト材料として遅延蛍光性（熱活性化遅延蛍光性）の化合物を用いることもできる。発光層が、上記で説明した本発明で用いる材料と、遅延蛍光性のホスト化合物と、を含むことも好ましい。
発光層は、上記で説明した本発明で用いる材料に加えて、上記の他の物質を含んでもよいし、含まなくてもよい。 (Host material of the light-emitting layer)
The light-emitting layer may have a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material). As a substance for dispersing the highly luminescent substance, various substances can be used in addition to the above-described materials used in the present invention (the compound represented by formula (1), the compound represented by formula (2), and the compound represented by formula (3)). It is preferable to use a substance having a lower lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the highly luminescent substance.
As a substance (host material) for dispersing a highly luminescent substance, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative; or 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative.
In addition, a delayed fluorescent (thermally activated delayed fluorescent) compound can be used as the host material. It is also preferable that the light-emitting layer contains the material used in the present invention described above and a delayed fluorescent host compound.
The light-emitting layer may or may not contain the above-mentioned other substances in addition to the materials used in the present invention described above.
（電子輸送層）
電子輸送層は、電子輸送性の高い物質を含む層である。電子輸送層には、１）アルミニウム錯体、ベリリウム錯体、亜鉛錯体等の金属錯体、２）イミダゾール誘導体、ベンゾイミダゾール誘導体、アジン誘導体、カルバゾール誘導体、フェナントロリン誘導体等の複素芳香族化合物、３）高分子化合物を使用することができる。 (Electron Transport Layer)
The electron transport layer is a layer containing a substance having high electron transport properties, and may be formed using 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound.
電子輸送層は、電子輸送性の高い物質を含む層である。電子輸送層には、１）アルミニウム錯体、ベリリウム錯体、亜鉛錯体等の金属錯体、２）イミダゾール誘導体、ベンゾイミダゾール誘導体、アジン誘導体、カルバゾール誘導体、フェナントロリン誘導体等の複素芳香族化合物、３）高分子化合物を使用することができる。 (Electron Transport Layer)
The electron transport layer is a layer containing a substance having high electron transport properties, and may be formed using 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound.
（電子注入層）
電子注入層は、電子注入性の高い物質を含む層である。電子注入層には、リチウム（Ｌｉ）、イッテルビウム（Ｙｂ）、フッ化リチウム（ＬｉＦ）、フッ化セシウム（ＣｓＦ）、フッ化カルシウム（ＣａＦ２）、８－ヒドロキシキノリノラト－リチウム（Ｌｉｑ）等の金属錯体化合物、リチウム酸化物（ＬｉＯｘ）等のアルカリ金属、アルカリ土類金属、又はそれらの化合物を用いることができる。 (Electron Injection Layer)
The electron injection layer is a layer containing a substance with high electron injection properties, and may be made of a metal complex compound such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), or 8-hydroxyquinolinolato-lithium (Liq), an alkali metal such as lithium oxide (LiO x ), an alkaline earth metal, or a compound thereof.
電子注入層は、電子注入性の高い物質を含む層である。電子注入層には、リチウム（Ｌｉ）、イッテルビウム（Ｙｂ）、フッ化リチウム（ＬｉＦ）、フッ化セシウム（ＣｓＦ）、フッ化カルシウム（ＣａＦ２）、８－ヒドロキシキノリノラト－リチウム（Ｌｉｑ）等の金属錯体化合物、リチウム酸化物（ＬｉＯｘ）等のアルカリ金属、アルカリ土類金属、又はそれらの化合物を用いることができる。 (Electron Injection Layer)
The electron injection layer is a layer containing a substance with high electron injection properties, and may be made of a metal complex compound such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), or 8-hydroxyquinolinolato-lithium (Liq), an alkali metal such as lithium oxide (LiO x ), an alkaline earth metal, or a compound thereof.
（陰極）
陰極には、仕事関数の小さい（具体的には３．８ｅＶ以下）金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。このような陰極材料の具体例としては、元素周期表の第１族又は第２族に属する元素、即ち、リチウム（Ｌｉ）やセシウム（Ｃｓ）等のアルカリ金属、及びマグネシウム（Ｍｇ）、カルシウム（Ｃａ）、ストロンチウム（Ｓｒ）等のアルカリ土類金属、及びこれらを含む合金（例えば、ＭｇＡｇ、ＡｌＬｉ）、ユーロピウム（Ｅｕ）、イッテルビウム（Ｙｂ）等の希土類金属及びこれらを含む合金等が挙げられる。
陰極は、通常、真空蒸着法やスパッタリング法で形成される。また、銀ペースト等を用いる場合は、塗布法やインクジェット法等を用いることができる。 (cathode)
For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging toGroup 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
The cathode is usually formed by a vacuum deposition method or a sputtering method. When a silver paste or the like is used, a coating method or an inkjet method can be used.
陰極には、仕事関数の小さい（具体的には３．８ｅＶ以下）金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。このような陰極材料の具体例としては、元素周期表の第１族又は第２族に属する元素、即ち、リチウム（Ｌｉ）やセシウム（Ｃｓ）等のアルカリ金属、及びマグネシウム（Ｍｇ）、カルシウム（Ｃａ）、ストロンチウム（Ｓｒ）等のアルカリ土類金属、及びこれらを含む合金（例えば、ＭｇＡｇ、ＡｌＬｉ）、ユーロピウム（Ｅｕ）、イッテルビウム（Ｙｂ）等の希土類金属及びこれらを含む合金等が挙げられる。
陰極は、通常、真空蒸着法やスパッタリング法で形成される。また、銀ペースト等を用いる場合は、塗布法やインクジェット法等を用いることができる。 (cathode)
For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to
The cathode is usually formed by a vacuum deposition method or a sputtering method. When a silver paste or the like is used, a coating method or an inkjet method can be used.
また、電子注入層が設けられる場合、仕事関数の大小に関わらず、アルミニウム、銀、ＩＴＯ、グラフェン、ケイ素もしくは酸化ケイ素を含有する酸化インジウム－酸化スズ等、種々の導電性材料を用いて陰極を形成することができる。
In addition, when an electron injection layer is provided, the cathode can be formed using various conductive materials, such as aluminum, silver, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function.
（電子阻止層、正孔阻止層、励起子阻止層）
発光層に隣接して、電子阻止層、正孔阻止層、励起子（トリプレット）阻止層等を設けてもよい。
電子阻止層とは、発光層から正孔輸送層へ電子が漏出することを阻止する機能を有する層である。正孔阻止層とは、発光層から電子輸送層へ正孔が漏出することを阻止する機能を有する層である。励起子阻止層は、発光層で生成した励起子が隣接する層へ拡散することを阻止し、励起子を発光層内に閉じ込める機能を有する層である。 (Electron Blocking Layer, Hole Blocking Layer, Exciton Blocking Layer)
Adjacent to the light-emitting layer, an electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc. may be provided.
The electron blocking layer is a layer having a function of preventing electrons from leaking from the light-emitting layer to the hole transport layer. The hole blocking layer is a layer having a function of preventing holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer is a layer having a function of preventing excitons generated in the light-emitting layer from diffusing to adjacent layers and confining the excitons within the light-emitting layer.
発光層に隣接して、電子阻止層、正孔阻止層、励起子（トリプレット）阻止層等を設けてもよい。
電子阻止層とは、発光層から正孔輸送層へ電子が漏出することを阻止する機能を有する層である。正孔阻止層とは、発光層から電子輸送層へ正孔が漏出することを阻止する機能を有する層である。励起子阻止層は、発光層で生成した励起子が隣接する層へ拡散することを阻止し、励起子を発光層内に閉じ込める機能を有する層である。 (Electron Blocking Layer, Hole Blocking Layer, Exciton Blocking Layer)
Adjacent to the light-emitting layer, an electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc. may be provided.
The electron blocking layer is a layer having a function of preventing electrons from leaking from the light-emitting layer to the hole transport layer. The hole blocking layer is a layer having a function of preventing holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer is a layer having a function of preventing excitons generated in the light-emitting layer from diffusing to adjacent layers and confining the excitons within the light-emitting layer.
本発明の一態様に係る有機ＥＬ素子において、各層の膜厚は特に制限されないが、一般にピンホール等の欠陥を抑制し、印加電圧を低く抑え、発光効率をよくするため、通常は数ｎｍから１μｍの範囲が好ましい。
In the organic EL element according to one embodiment of the present invention, the thickness of each layer is not particularly limited, but in general, a thickness in the range of several nm to 1 μm is preferable in order to suppress defects such as pinholes, keep the applied voltage low, and improve the light emission efficiency.
本発明の一態様に係る有機ＥＬ素子において、各層の形成方法は特に限定されない。従来公知の真空蒸着法、スピンコーティング法等による形成方法を用いることができる。発光層等の各層は、真空蒸着法、分子線蒸着法（ＭＢＥ法）あるいは溶媒に溶かした溶液のディッピング法、スピンコーティング法、キャスティング法、バーコート法、ロールコート法等の塗布法による公知の方法で形成することができる。
In the organic EL element according to one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by known methods such as vacuum deposition, molecular beam deposition (MBE), or coating methods such as dipping a solution dissolved in a solvent, spin coating, casting, bar coating, and roll coating.
［電子機器］
本発明の一態様に係る電子機器は、本発明の一態様に係る有機ＥＬ素子を備えることを特徴とする。
電子機器の具体例としては、有機ＥＬパネルモジュール等の表示部品、テレビ、携帯電話、又はパーソナルコンピュータ等の表示装置、及び、照明、又は車両用灯具等の発光装置等が挙げられる。 [Electronic devices]
An electronic device according to an aspect of the present invention includes the organic EL element according to an aspect of the present invention.
Specific examples of electronic devices include display components such as organic EL panel modules, display devices for televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps.
本発明の一態様に係る電子機器は、本発明の一態様に係る有機ＥＬ素子を備えることを特徴とする。
電子機器の具体例としては、有機ＥＬパネルモジュール等の表示部品、テレビ、携帯電話、又はパーソナルコンピュータ等の表示装置、及び、照明、又は車両用灯具等の発光装置等が挙げられる。 [Electronic devices]
An electronic device according to an aspect of the present invention includes the organic EL element according to an aspect of the present invention.
Specific examples of electronic devices include display components such as organic EL panel modules, display devices for televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps.
＜化合物＞
実施例の有機ＥＬ素子の製造に用いた、式（１）、式（２）、又は式（３）で表される化合物を以下に示す。
<Compound>
The compounds represented by formula (1), formula (2), or formula (3) used in the production of the organic EL devices of the examples are shown below.
実施例の有機ＥＬ素子の製造に用いた、式（１）、式（２）、又は式（３）で表される化合物を以下に示す。
The compounds represented by formula (1), formula (2), or formula (3) used in the production of the organic EL devices of the examples are shown below.
比較例の有機ＥＬ素子の製造に用いた化合物を以下に示す。
The compounds used in the production of the organic EL device of the comparative example are shown below.
実施例及び比較例の有機ＥＬ素子の製造に用いた他の化合物の構造を以下に示す。
The structures of other compounds used in the production of the organic EL devices of the Examples and Comparative Examples are shown below.
（基のＴ１の評価）
表１に示す基について、Ｂ３ＬＹＰ／６－３１Ｇ（ｄ）で計算した最安定構造に対して、時間依存密度汎関数法（ＴＤ－Ｂ３ＬＹＰ／６－３１Ｇ（ｄ））により三重項励起状態のエネルギー（Ｔ１）を計算した。ソフトウェア、汎関数、及び基底関数として、以下のものを用いた。
・ソフトウェア：Ｇａｕｓｓｉａｎ １６，Ｒｅｖｉｓｉｏｎ Ｂ．０１
・汎関数：Ｂ３ＬＹＰ
・基底関数：６－３１Ｇ（ｄ）
評価結果を表１に示す。 (Evaluation of Group T1 )
For the groups shown in Table 1, the triplet excited state energy (T 1 ) was calculated by the time-dependent density functional method (TD-B3LYP/6-31G(d)) for the most stable structures calculated by B3LYP/6-31G(d). The following software, functionals, and basis functions were used.
Software: Gaussian 16, Revision B.01
Functional function: B3LYP
Basis function: 6-31G(d)
The evaluation results are shown in Table 1.
表１に示す基について、Ｂ３ＬＹＰ／６－３１Ｇ（ｄ）で計算した最安定構造に対して、時間依存密度汎関数法（ＴＤ－Ｂ３ＬＹＰ／６－３１Ｇ（ｄ））により三重項励起状態のエネルギー（Ｔ１）を計算した。ソフトウェア、汎関数、及び基底関数として、以下のものを用いた。
・ソフトウェア：Ｇａｕｓｓｉａｎ １６，Ｒｅｖｉｓｉｏｎ Ｂ．０１
・汎関数：Ｂ３ＬＹＰ
・基底関数：６－３１Ｇ（ｄ）
評価結果を表１に示す。 (Evaluation of Group T1 )
For the groups shown in Table 1, the triplet excited state energy (T 1 ) was calculated by the time-dependent density functional method (TD-B3LYP/6-31G(d)) for the most stable structures calculated by B3LYP/6-31G(d). The following software, functionals, and basis functions were used.
Software: Gaussian 16, Revision B.01
Functional function: B3LYP
Basis function: 6-31G(d)
The evaluation results are shown in Table 1.
（化合物の評価）
実施例及び比較例の有機ＥＬ素子の製造においてホスト材料又はドーパント材料として用いた化合物について、一重項エネルギー（Ｓ１）と三重項エネルギー（Ｔ１）を以下のとおり測定した。結果を表２に示す。 (Evaluation of Compounds)
The singlet energy (S 1 ) and triplet energy (T 1 ) of the compounds used as host materials or dopant materials in the production of the organic EL devices of the Examples and Comparative Examples were measured as follows. The results are shown in Table 2.
実施例及び比較例の有機ＥＬ素子の製造においてホスト材料又はドーパント材料として用いた化合物について、一重項エネルギー（Ｓ１）と三重項エネルギー（Ｔ１）を以下のとおり測定した。結果を表２に示す。 (Evaluation of Compounds)
The singlet energy (S 1 ) and triplet energy (T 1 ) of the compounds used as host materials or dopant materials in the production of the organic EL devices of the Examples and Comparative Examples were measured as follows. The results are shown in Table 2.
・一重項エネルギーＳ１
測定対象となる化合物の１０μｍｏｌ／Ｌトルエン溶液を調製して石英セルに入れ、常温（３００Ｋ）でこの試料の吸収スペクトル（縦軸：吸収強度、横軸：波長とする。）を測定した。この吸収スペクトルの長波長側の立ち下がりに対して接線を引き、その接線と横軸との交点の波長値λｅｄｇｅ［ｎｍ］を次に示す換算式（Ｆ２）に代入して一重項エネルギーを算出した。
換算式（Ｆ２）：Ｓ１［ｅＶ］＝１２３９．８５／λｅｄｇｅ
吸収スペクトル測定装置としては、日立社製の分光光度計（装置名：Ｕ３３１０）を用いた。 Singlet energy S 1
A 10 μmol/L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). A tangent line was drawn to the trailing edge on the long wavelength side of this absorption spectrum, and the wavelength value λ edge [nm] at the intersection of the tangent line and the horizontal axis was substituted into the following conversion formula (F2) to calculate the singlet energy.
Conversion formula (F2): S 1 [eV] = 1239.85/λ edge
The absorption spectrum measuring device used was a spectrophotometer manufactured by Hitachi Ltd. (device name: U3310).
測定対象となる化合物の１０μｍｏｌ／Ｌトルエン溶液を調製して石英セルに入れ、常温（３００Ｋ）でこの試料の吸収スペクトル（縦軸：吸収強度、横軸：波長とする。）を測定した。この吸収スペクトルの長波長側の立ち下がりに対して接線を引き、その接線と横軸との交点の波長値λｅｄｇｅ［ｎｍ］を次に示す換算式（Ｆ２）に代入して一重項エネルギーを算出した。
換算式（Ｆ２）：Ｓ１［ｅＶ］＝１２３９．８５／λｅｄｇｅ
吸収スペクトル測定装置としては、日立社製の分光光度計（装置名：Ｕ３３１０）を用いた。 Singlet energy S 1
A 10 μmol/L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). A tangent line was drawn to the trailing edge on the long wavelength side of this absorption spectrum, and the wavelength value λ edge [nm] at the intersection of the tangent line and the horizontal axis was substituted into the following conversion formula (F2) to calculate the singlet energy.
Conversion formula (F2): S 1 [eV] = 1239.85/λ edge
The absorption spectrum measuring device used was a spectrophotometer manufactured by Hitachi Ltd. (device name: U3310).
吸収スペクトルの長波長側の立ち下がりに対する接線は以下のように引く。吸収スペクトルの極大値のうち、最も長波長側の極大値から長波長方向にスペクトル曲線上を移動する際に、曲線上の各点における接線を考える。この接線は、曲線が立ち下がるにつれ（つまり縦軸の値が減少するにつれ）、傾きが減少しその後増加することを繰り返す。傾きの値が最も長波長側（ただし、吸光度が０．１以下となる場合は除く）で極小値をとる点において引いた接線を当該吸収スペクトルの長波長側の立ち下がりに対する接線とする。
なお、吸光度の値が０．２以下の極大点は、上記最も長波長側の極大値には含めない。 The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving on the spectral curve from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum in the direction towards longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the fall on the long wavelength side of the absorption spectrum.
Note that maximum points with absorbance values of 0.2 or less are not included in the maximum values on the longest wavelength side.
なお、吸光度の値が０．２以下の極大点は、上記最も長波長側の極大値には含めない。 The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving on the spectral curve from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum in the direction towards longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the fall on the long wavelength side of the absorption spectrum.
Note that maximum points with absorbance values of 0.2 or less are not included in the maximum values on the longest wavelength side.
・三重項エネルギーＴ１
測定対象となる化合物をＥＰＡ（ジエチルエーテル：イソペンタン：エタノール＝５：５：２（容積比））中に、１０－５ｍｏｌ／Ｌ以上１０－４ｍｏｌ／Ｌ以下となるように溶解し、この溶液を石英セル中に入れて測定試料とした。この測定試料について、低温（７７［Ｋ］）で燐光スペクトル（縦軸：燐光発光強度、横軸：波長とする。）を測定し、この燐光スペクトルの短波長側の立ち上がりに対して接線を引き、その接線と横軸との交点の波長値λｅｄｇｅ［ｎｍ］に基づいて、次の換算式（Ｆ１）から算出されるエネルギー量を三重項エネルギーＴ１とした。
換算式（Ｆ１）：Ｔ１［ｅＶ］＝１２３９．８５／λｅｄｇｅ Triplet energy T 1
The compound to be measured was dissolved in EPA (diethyl ether:isopentane:ethanol=5:5:2 (volume ratio)) to a concentration of 10 -5 mol/L or more and 10 -4 mol/L or less, and this solution was placed in a quartz cell to prepare a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), a tangent was drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the amount of energy calculated from the following conversion formula (F1) based on the wavelength value λ edge [nm] at the intersection of the tangent and the horizontal axis was defined as the triplet energy T1 .
Conversion formula (F1): T 1 [eV] = 1239.85/λ edge
測定対象となる化合物をＥＰＡ（ジエチルエーテル：イソペンタン：エタノール＝５：５：２（容積比））中に、１０－５ｍｏｌ／Ｌ以上１０－４ｍｏｌ／Ｌ以下となるように溶解し、この溶液を石英セル中に入れて測定試料とした。この測定試料について、低温（７７［Ｋ］）で燐光スペクトル（縦軸：燐光発光強度、横軸：波長とする。）を測定し、この燐光スペクトルの短波長側の立ち上がりに対して接線を引き、その接線と横軸との交点の波長値λｅｄｇｅ［ｎｍ］に基づいて、次の換算式（Ｆ１）から算出されるエネルギー量を三重項エネルギーＴ１とした。
換算式（Ｆ１）：Ｔ１［ｅＶ］＝１２３９．８５／λｅｄｇｅ Triplet energy T 1
The compound to be measured was dissolved in EPA (diethyl ether:isopentane:ethanol=5:5:2 (volume ratio)) to a concentration of 10 -5 mol/L or more and 10 -4 mol/L or less, and this solution was placed in a quartz cell to prepare a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), a tangent was drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the amount of energy calculated from the following conversion formula (F1) based on the wavelength value λ edge [nm] at the intersection of the tangent and the horizontal axis was defined as the triplet energy T1 .
Conversion formula (F1): T 1 [eV] = 1239.85/λ edge
燐光スペクトルの短波長側の立ち上がりに対する接線は以下のように引いた。燐光スペクトルの短波長側から、スペクトルの極大値のうち、最も短波長側の極大値までスペクトル曲線上を移動する際に、長波長側に向けて曲線上の各点における接線を考える。この接線は、曲線が立ち上がるにつれ（つまり縦軸が増加するにつれ）、傾きが増加する。この傾きの値が極大値をとる点において引いた接線（すなわち変曲点における接線）が、当該燐光スペクトルの短波長側の立ち上がりに対する接線とした。
なお、スペクトルの最大ピーク強度の１５％以下のピーク強度をもつ極大点は、上述の最も短波長側の極大値には含めず、最も短波長側の極大値に最も近い、傾きの値が極大値をとる点において引いた接線を当該燐光スペクトルの短波長側の立ち上がりに対する接線とした。
燐光の測定には、株式会社日立ハイテク製のＦ－７１００形分光蛍光光度計本体を用いた。 The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side was drawn as follows. When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, a tangent to each point on the curve toward the long wavelength side was considered. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) was taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
Note that a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum was not included in the maximum value on the shortest wavelength side described above, and a tangent drawn at a point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side was defined as a tangent to the rising edge on the short wavelength side of the phosphorescence spectrum.
The phosphorescence was measured using a Hitachi High-Tech F-7100 spectrofluorophotometer.
なお、スペクトルの最大ピーク強度の１５％以下のピーク強度をもつ極大点は、上述の最も短波長側の極大値には含めず、最も短波長側の極大値に最も近い、傾きの値が極大値をとる点において引いた接線を当該燐光スペクトルの短波長側の立ち上がりに対する接線とした。
燐光の測定には、株式会社日立ハイテク製のＦ－７１００形分光蛍光光度計本体を用いた。 The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side was drawn as follows. When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, a tangent to each point on the curve toward the long wavelength side was considered. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) was taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
Note that a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum was not included in the maximum value on the shortest wavelength side described above, and a tangent drawn at a point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side was defined as a tangent to the rising edge on the short wavelength side of the phosphorescence spectrum.
The phosphorescence was measured using a Hitachi High-Tech F-7100 spectrofluorophotometer.
実施例１
＜有機ＥＬ素子の作製＞
有機ＥＬ素子を以下のように作製した。
２５ｍｍ×７５ｍｍ×１．１ｍｍ厚のＩＴＯ透明電極（陽極）付きガラス基板（ジオマティック株式会社製）をイソプロピルアルコール中で超音波洗浄を５分間行なった後、ＵＶオゾン洗浄を３０分間行なった。ＩＴＯの膜厚は１３０ｎｍとした。
洗浄後の透明電極付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極が形成されている側の面上に透明電極を覆うようにして化合物ＨＩ１を蒸着し、膜厚５ｎｍの第１正孔輸送層を成膜した。
第１正孔輸送層上に、化合物ＨＴ１を蒸着し、膜厚８０ｎｍの第２正孔輸送層を成膜した。
第２正孔輸送層上に、化合物ＥＢＬ１を蒸着し、膜厚１０ｎｍの第３正孔輸送層を成膜した。
第３正孔輸送層上に化合物ＢＨ１－１（ホスト材料）及び化合物ＢＤ１（ドーパント材料）を、化合物ＢＤ１の割合が２質量％となるように共蒸着し、膜厚５ｎｍの第１の発光層を成膜した。
第１の発光層上に、化合物ＢＨ２－１（ホスト材料）及び化合物ＢＤ１（ドーパント材料）を、化合物ＢＤ１の割合が２質量％となるように共蒸着し、膜厚２０ｎｍの第２の発光層を成膜した。
第２の発光層上に、化合物ＨＢＬ１を蒸着し、膜厚１０ｎｍの第１電子輸送層を形成した。
第１電子輸送層上に、化合物ＥＴ１を蒸着し、膜厚１５ｎｍの第２電子輸送層を形成した。
第２電子輸送層上に、ＬｉＦを蒸着し、膜厚１ｎｍの電子注入層を形成した。
電子注入層上に、金属Ａｌを蒸着し、膜厚８０ｎｍの陰極を成膜した。 Example 1
<Preparation of Organic EL Element>
An organic EL device was fabricated as follows.
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and compound HI1 was deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a first hole transport layer with a thickness of 5 nm.
On the first hole transport layer, the compound HT1 was evaporated to form a second hole transport layer having a thickness of 80 nm.
On the second hole transport layer, the compound EBL1 was evaporated to form a third hole transport layer having a thickness of 10 nm.
On the third hole transport layer, the compound BH1-1 (host material) and the compound BD1 (dopant material) were co-deposited so that the ratio of the compound BD1 was 2 mass %, to form a first light-emitting layer with a thickness of 5 nm.
On the first emitting layer, the compound BH2-1 (host material) and the compound BD1 (dopant material) were co-deposited so that the ratio of the compound BD1 was 2 mass %, to form a second emitting layer having a thickness of 20 nm.
On the second light-emitting layer, the compound HBL1 was evaporated to form a first electron transport layer having a thickness of 10 nm.
On the first electron transport layer, a compound ET1 was deposited by vapor deposition to form a second electron transport layer having a thickness of 15 nm.
LiF was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 80 nm.
＜有機ＥＬ素子の作製＞
有機ＥＬ素子を以下のように作製した。
２５ｍｍ×７５ｍｍ×１．１ｍｍ厚のＩＴＯ透明電極（陽極）付きガラス基板（ジオマティック株式会社製）をイソプロピルアルコール中で超音波洗浄を５分間行なった後、ＵＶオゾン洗浄を３０分間行なった。ＩＴＯの膜厚は１３０ｎｍとした。
洗浄後の透明電極付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極が形成されている側の面上に透明電極を覆うようにして化合物ＨＩ１を蒸着し、膜厚５ｎｍの第１正孔輸送層を成膜した。
第１正孔輸送層上に、化合物ＨＴ１を蒸着し、膜厚８０ｎｍの第２正孔輸送層を成膜した。
第２正孔輸送層上に、化合物ＥＢＬ１を蒸着し、膜厚１０ｎｍの第３正孔輸送層を成膜した。
第３正孔輸送層上に化合物ＢＨ１－１（ホスト材料）及び化合物ＢＤ１（ドーパント材料）を、化合物ＢＤ１の割合が２質量％となるように共蒸着し、膜厚５ｎｍの第１の発光層を成膜した。
第１の発光層上に、化合物ＢＨ２－１（ホスト材料）及び化合物ＢＤ１（ドーパント材料）を、化合物ＢＤ１の割合が２質量％となるように共蒸着し、膜厚２０ｎｍの第２の発光層を成膜した。
第２の発光層上に、化合物ＨＢＬ１を蒸着し、膜厚１０ｎｍの第１電子輸送層を形成した。
第１電子輸送層上に、化合物ＥＴ１を蒸着し、膜厚１５ｎｍの第２電子輸送層を形成した。
第２電子輸送層上に、ＬｉＦを蒸着し、膜厚１ｎｍの電子注入層を形成した。
電子注入層上に、金属Ａｌを蒸着し、膜厚８０ｎｍの陰極を成膜した。 Example 1
<Preparation of Organic EL Element>
An organic EL device was fabricated as follows.
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and compound HI1 was deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a first hole transport layer with a thickness of 5 nm.
On the first hole transport layer, the compound HT1 was evaporated to form a second hole transport layer having a thickness of 80 nm.
On the second hole transport layer, the compound EBL1 was evaporated to form a third hole transport layer having a thickness of 10 nm.
On the third hole transport layer, the compound BH1-1 (host material) and the compound BD1 (dopant material) were co-deposited so that the ratio of the compound BD1 was 2 mass %, to form a first light-emitting layer with a thickness of 5 nm.
On the first emitting layer, the compound BH2-1 (host material) and the compound BD1 (dopant material) were co-deposited so that the ratio of the compound BD1 was 2 mass %, to form a second emitting layer having a thickness of 20 nm.
On the second light-emitting layer, the compound HBL1 was evaporated to form a first electron transport layer having a thickness of 10 nm.
On the first electron transport layer, a compound ET1 was deposited by vapor deposition to form a second electron transport layer having a thickness of 15 nm.
LiF was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 80 nm.
実施例１の有機ＥＬ素子の素子構成を略式的に示すと、次の通りである。
ITO(130)/HI1(5)/HT1(80)/EBL1(10)/BH1-1:BD1(5:2%)/BH2-1:BD1(20:2%)/HBL1(10)/ET1(15)/LiF(1)/Al(80)
括弧内の数字は膜厚（単位：ｎｍ）を表す。
また、括弧内においてパーセント表示された数字は、当該層における後者の化合物の割合（質量％）を示す。 The device configuration of the organic EL device of Example 1 is roughly shown as follows.
ITO(130)/HI1(5)/HT1(80)/EBL1(10)/BH1-1:BD1(5:2%)/BH2-1:BD1(20:2%)/HBL1(10)/ET1(15)/LiF(1)/Al(80)
The numbers in parentheses indicate the film thickness (unit: nm).
Moreover, the percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the layer.
ITO(130)/HI1(5)/HT1(80)/EBL1(10)/BH1-1:BD1(5:2%)/BH2-1:BD1(20:2%)/HBL1(10)/ET1(15)/LiF(1)/Al(80)
括弧内の数字は膜厚（単位：ｎｍ）を表す。
また、括弧内においてパーセント表示された数字は、当該層における後者の化合物の割合（質量％）を示す。 The device configuration of the organic EL device of Example 1 is roughly shown as follows.
ITO(130)/HI1(5)/HT1(80)/EBL1(10)/BH1-1:BD1(5:2%)/BH2-1:BD1(20:2%)/HBL1(10)/ET1(15)/LiF(1)/Al(80)
The numbers in parentheses indicate the film thickness (unit: nm).
Moreover, the percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the layer.
＜有機ＥＬ素子の評価＞
作製した有機ＥＬ素子について以下の評価を行った。結果を表３に示す。
・駆動電圧
実施例及び比較例で作製した有機ＥＬ素子について、電流密度が１０ｍＡ／ｃｍ２となるように有機ＥＬ素子に電圧を印加したときの電圧（単位：Ｖ）を計測した。
・最大ピーク波長λｐ
電流密度が１０ｍＡ／ｃｍ２となるように素子に電圧を印加した時の分光放射輝度スペクトルを分光放射輝度計ＣＳ－２０００（コニカミノルタ株式会社製）で計測した。得られた分光放射輝度スペクトルから、最大ピーク波長λｐ（単位：ｎｍ）を求めた。
・ＣＩＥ１９３１色度
電流密度が１０ｍＡ／ｃｍ２となるように有機ＥＬ素子に電圧を印加した時のＣＩＥ１９３１色度座標（ｘ、ｙ）を分光放射輝度計ＣＳ－２０００（コニカミノルタ株式会社製）で計測した。 <Evaluation of Organic EL Device>
The organic EL devices thus fabricated were subjected to the following evaluations. The results are shown in Table 3.
Driving Voltage For the organic EL elements produced in the examples and comparative examples, a voltage (unit: V) was measured when a voltage was applied to the organic EL element so that the current density was 10 mA/cm 2 .
Maximum peak wavelength λ p
The spectral radiance spectrum when a voltage was applied to the element so that the current density was 10 mA/ cm2 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the maximum peak wavelength λ p (unit: nm) was obtained.
CIE 1931 chromaticity The CIE 1931 chromaticity coordinates (x, y) when a voltage was applied to the organic EL element so that the current density was 10 mA/cm 2 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).
作製した有機ＥＬ素子について以下の評価を行った。結果を表３に示す。
・駆動電圧
実施例及び比較例で作製した有機ＥＬ素子について、電流密度が１０ｍＡ／ｃｍ２となるように有機ＥＬ素子に電圧を印加したときの電圧（単位：Ｖ）を計測した。
・最大ピーク波長λｐ
電流密度が１０ｍＡ／ｃｍ２となるように素子に電圧を印加した時の分光放射輝度スペクトルを分光放射輝度計ＣＳ－２０００（コニカミノルタ株式会社製）で計測した。得られた分光放射輝度スペクトルから、最大ピーク波長λｐ（単位：ｎｍ）を求めた。
・ＣＩＥ１９３１色度
電流密度が１０ｍＡ／ｃｍ２となるように有機ＥＬ素子に電圧を印加した時のＣＩＥ１９３１色度座標（ｘ、ｙ）を分光放射輝度計ＣＳ－２０００（コニカミノルタ株式会社製）で計測した。 <Evaluation of Organic EL Device>
The organic EL devices thus fabricated were subjected to the following evaluations. The results are shown in Table 3.
Driving Voltage For the organic EL elements produced in the examples and comparative examples, a voltage (unit: V) was measured when a voltage was applied to the organic EL element so that the current density was 10 mA/cm 2 .
Maximum peak wavelength λ p
The spectral radiance spectrum when a voltage was applied to the element so that the current density was 10 mA/ cm2 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the maximum peak wavelength λ p (unit: nm) was obtained.
CIE 1931 chromaticity The CIE 1931 chromaticity coordinates (x, y) when a voltage was applied to the organic EL element so that the current density was 10 mA/cm 2 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).
実施例２～１３、比較例１
ＢＨ１－１の代わりに表３に記載の化合物を用いた以外は、実施例１と同じ方法で有機ＥＬ素子を作製し、評価した。結果を表３に示す。 Examples 2 to 13, Comparative Example 1
Except for using the compound shown in Table 3 instead of BH1-1, an organic EL device was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 3.
ＢＨ１－１の代わりに表３に記載の化合物を用いた以外は、実施例１と同じ方法で有機ＥＬ素子を作製し、評価した。結果を表３に示す。 Examples 2 to 13, Comparative Example 1
Except for using the compound shown in Table 3 instead of BH1-1, an organic EL device was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 3.
表３によれば、式（１）で表される構造を有する第一の化合物を第一のホスト材料として用いた実施例１～１３の有機ＥＬ素子は、ＢＨ１－Ｒｅｆ１を用いた比較例１の有機ＥＬ素子に比べて、素子の低電圧化を達成し、色度悪化が抑制されていることが分かる。
Table 3 shows that the organic EL elements of Examples 1 to 13, which use a first compound having a structure represented by formula (1) as a first host material, achieve a lower device voltage and suppress deterioration in chromaticity compared to the organic EL element of Comparative Example 1, which uses BH1-Ref1.
＜化合物の合成＞
（合成実施例１）ＢＨ１－１の合成
下記合成経路で、ＢＨ１－１を合成した。
中間体１（２．６７ｇ）、中間体２（２．３０ｇ）、Ｐｄ２（ｄｂａ）３（０．１２ｇ）、ＳＰｈｏｓ（０．２１ｇ）、及び炭酸セシウム（４．２０ｇ）をフラスコに入れ、フラスコ内をアルゴンガスで置換した後、１，４－ジオキサン（２８ｍＬ）、及び水（４．６ｍＬ）を加え、還流条件下で６時間加熱撹拌した。反応溶液を冷却後、メタノールを加えて析出した固体を濾取し、メタノールと水で洗浄した。得られた粗生成物をシリカゲルクロマトグラフィーにより精製することで、ＢＨ１－１を淡黄色固体（２．５３ｇ、収率７２％）として得た。
マススペクトル分析の結果、分子量５４４．６５に対してｍ／ｅ＝５４５であり、目的物であると同定した。 <Synthesis of Compounds>
(Synthesis Example 1) Synthesis of BH1-1 BH1-1 was synthesized according to the following synthesis route.
Intermediate 1 (2.67 g), intermediate 2 (2.30 g), Pd 2 (dba) 3 (0.12 g), SPhos (0.21 g), and cesium carbonate (4.20 g) were placed in a flask, and the flask was replaced with argon gas. Then, 1,4-dioxane (28 mL) and water (4.6 mL) were added, and the mixture was heated and stirred under reflux conditions for 6 hours. After cooling the reaction solution, methanol was added, and the precipitated solid was filtered and washed with methanol and water. The obtained crude product was purified by silica gel chromatography to obtain BH1-1 as a pale yellow solid (2.53 g, yield 72%).
Mass spectrometry revealed that the molecular weight was 544.65 with m/e=545, and the product was identified as the target substance.
（合成実施例１）ＢＨ１－１の合成
下記合成経路で、ＢＨ１－１を合成した。
マススペクトル分析の結果、分子量５４４．６５に対してｍ／ｅ＝５４５であり、目的物であると同定した。 <Synthesis of Compounds>
(Synthesis Example 1) Synthesis of BH1-1 BH1-1 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 544.65 with m/e=545, and the product was identified as the target substance.
（合成実施例２）ＢＨ１－２の合成
下記合成経路で、ＢＨ１－２を合成した。
ＢＨ１－１の合成において、中間体１の代わりに中間体３を用いた以外は同様の方法で合成し、ＢＨ１－２を淡黄色固体（１．８１ｇ、収率５２％）として得た。
マススペクトル分析の結果、分子量５４４．６５に対してｍ／ｅ＝５４５であり、目的物であると同定した。 (Synthesis Example 2) Synthesis of BH1-2 BH1-2 was synthesized according to the following synthesis route.
BH1-2 was obtained as a pale yellow solid (1.81 g, yield 52%) in the same manner as in the synthesis of BH1-1, except that intermediate 3 was used instead of intermediate 1.
Mass spectrometry revealed that the molecular weight was 544.65 with m/e=545, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－２を合成した。
マススペクトル分析の結果、分子量５４４．６５に対してｍ／ｅ＝５４５であり、目的物であると同定した。 (Synthesis Example 2) Synthesis of BH1-2 BH1-2 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 544.65 with m/e=545, and the product was identified as the target substance.
（合成実施例３）ＢＨ１－３の合成
下記合成経路で、ＢＨ１－３を合成した。
中間体１（５．０４ｇ）、中間体４（４．００ｇ）、Ｐｄ２（ｄｂａ）３（０．２２ｇ）、及びＳＰｈｏｓ（０．４０ｇ）をフラスコに入れ、フラスコ内をアルゴンガスで置換した後、１，４－ジオキサン（１２２ｍＬ）、及び２Ｍ炭酸ナトリウム水溶液（１５．２ｍＬ）を加え、還流条件下で６時間加熱撹拌した。溶媒を留去し、得られた粗生成物をシリカゲルクロマトグラフィーにより精製し、トルエンとジメトキシエタンで洗浄することでＢＨ１－３を白色固体（４．０２ｇ、収率５９％）として得た。
マススペクトル分析の結果、分子量５６０．６９に対してｍ／ｅ＝５６１であり、目的物であると同定した。 (Synthesis Example 3) Synthesis of BH1-3 BH1-3 was synthesized according to the following synthesis route.
Intermediate 1 (5.04 g), intermediate 4 (4.00 g), Pd 2 (dba) 3 (0.22 g), and SPhos (0.40 g) were placed in a flask, and the atmosphere in the flask was replaced with argon gas. Then, 1,4-dioxane (122 mL) and 2 M aqueous sodium carbonate solution (15.2 mL) were added, and the mixture was heated and stirred under reflux conditions for 6 hours. The solvent was removed, and the resulting crude product was purified by silica gel chromatography and washed with toluene and dimethoxyethane to obtain BH1-3 as a white solid (4.02 g, yield 59%).
Mass spectrometry revealed that the molecular weight was 560.69 with m/e=561, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－３を合成した。
マススペクトル分析の結果、分子量５６０．６９に対してｍ／ｅ＝５６１であり、目的物であると同定した。 (Synthesis Example 3) Synthesis of BH1-3 BH1-3 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 560.69 with m/e=561, and the product was identified as the target substance.
（合成実施例４）ＢＨ１－４の合成
下記合成経路で、ＢＨ１－４を合成した。
ＢＨ１－３の合成において、中間体４の代わりに中間体５を用いた以外は同様の方法で合成し、ＢＨ１－４を白色固体（３．１９ｇ、収率４９％）として得た。
マススペクトル分析の結果、分子量５１０．６３に対してｍ／ｅ＝５１１であり、目的物であると同定した。 (Synthesis Example 4) Synthesis of BH1-4 BH1-4 was synthesized according to the following synthesis route.
BH1-4 was obtained as a white solid (3.19 g, yield 49%) in the same manner as in the synthesis of BH1-3, except that intermediate 5 was used instead of intermediate 4.
Mass spectrometry revealed that the molecular weight was 510.63 with m/e=511, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－４を合成した。
マススペクトル分析の結果、分子量５１０．６３に対してｍ／ｅ＝５１１であり、目的物であると同定した。 (Synthesis Example 4) Synthesis of BH1-4 BH1-4 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 510.63 with m/e=511, and the product was identified as the target substance.
（合成実施例５）ＢＨ１－５の合成
下記合成経路で、ＢＨ１－５を合成した。
ＢＨ１－１の合成において、中間体２の代わりに中間体６を用いた以外は同様の方法で合成し、ＢＨ１－５を白色固体（１．４３ｇ、収率４０％）として得た。
マススペクトル分析の結果、分子量４６８．５５に対してｍ／ｅ＝４６９であり、目的物であると同定した。 (Synthesis Example 5) Synthesis of BH1-5 BH1-5 was synthesized according to the following synthesis route.
BH1-5 was obtained as a white solid (1.43 g, yield 40%) in the same manner as in the synthesis of BH1-1, except that intermediate 6 was used instead of intermediate 2.
Mass spectrometry revealed that the molecular weight was 468.55 with m/e=469, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－５を合成した。
マススペクトル分析の結果、分子量４６８．５５に対してｍ／ｅ＝４６９であり、目的物であると同定した。 (Synthesis Example 5) Synthesis of BH1-5 BH1-5 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 468.55 with m/e=469, and the product was identified as the target substance.
（合成実施例６）ＢＨ１－６の合成
下記合成経路で、ＢＨ１－６を合成した。
ＢＨ１－１の合成において、中間体１の代わりに中間体３を、中間体２の代わりに中間体６を用いた以外は同様の方法で合成し、ＢＨ１－６を白色固体（１．１９ｇ、収率３３％）として得た。
マススペクトル分析の結果、分子量４６８．５５に対してｍ／ｅ＝４６９であり、目的物であると同定した。 (Synthesis Example 6) Synthesis of BH1-6 BH1-6 was synthesized according to the following synthesis route.
BH1-6 was obtained as a white solid (1.19 g, yield 33%) in the same manner as in the synthesis of BH1-1, except that intermediate 3 was used instead of intermediate 1 and intermediate 6 was used instead of intermediate 2.
Mass spectrometry revealed that the molecular weight was 468.55 with m/e=469, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－６を合成した。
マススペクトル分析の結果、分子量４６８．５５に対してｍ／ｅ＝４６９であり、目的物であると同定した。 (Synthesis Example 6) Synthesis of BH1-6 BH1-6 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 468.55 with m/e=469, and the product was identified as the target substance.
（合成実施例７）ＢＨ１－７の合成
下記合成経路で、ＢＨ１－７を合成した。
ＢＨ１－３の合成において、中間体４の代わりに中間体７を用いた以外は同様の方法で合成し、ＢＨ１－７を白色固体（１．７８ｇ、収率７１％）として得た。
マススペクトル分析の結果、分子量４９４．５９に対してｍ／ｅ＝４９５であり、目的物であると同定した。 (Synthesis Example 7) Synthesis of BH1-7 BH1-7 was synthesized according to the following synthesis route.
BH1-7 was obtained as a white solid (1.78 g, yield 71%) in the same manner as in the synthesis of BH1-3, except that intermediate 7 was used instead of intermediate 4.
Mass spectrometry revealed that the molecular weight was 494.59 with m/e=495, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－７を合成した。
マススペクトル分析の結果、分子量４９４．５９に対してｍ／ｅ＝４９５であり、目的物であると同定した。 (Synthesis Example 7) Synthesis of BH1-7 BH1-7 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 494.59 with m/e=495, and the product was identified as the target substance.
（合成実施例８）ＢＨ１－８の合成
下記合成経路で、ＢＨ１－８を合成した。
ＢＨ１－３の合成において、中間体４の代わりに中間体８を用いた以外は同様の方法で合成し、ＢＨ１－８を白色固体（１．３２ｇ、収率５４％）として得た。
マススペクトル分析の結果、分子量４８４．５５に対してｍ／ｅ＝４８５であり、目的物であると同定した。 (Synthesis Example 8) Synthesis of BH1-8 BH1-8 was synthesized according to the following synthesis route.
BH1-8 was obtained as a white solid (1.32 g, yield 54%) in the same manner as in the synthesis of BH1-3, except that intermediate 8 was used instead of intermediate 4.
Mass spectrometry revealed that the molecular weight was 484.55 with m/e=485, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－８を合成した。
マススペクトル分析の結果、分子量４８４．５５に対してｍ／ｅ＝４８５であり、目的物であると同定した。 (Synthesis Example 8) Synthesis of BH1-8 BH1-8 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 484.55 with m/e=485, and the product was identified as the target substance.
（合成実施例９）ＢＨ１－９の合成
下記合成経路で、ＢＨ１－９を合成した。
ＢＨ１－３の合成において、中間体４の代わりに中間体９を用いた以外は同様の方法で合成し、ＢＨ１－９を白色固体（１．６６ｇ、収率６３％）として得た。
マススペクトル分析の結果、分子量４８４．５５に対してｍ／ｅ＝４８５であり、目的物であると同定した。 (Synthesis Example 9) Synthesis of BH1-9 BH1-9 was synthesized according to the following synthesis route.
BH1-9 was obtained as a white solid (1.66 g, yield 63%) in the same manner as in the synthesis of BH1-3, except that intermediate 9 was used instead of intermediate 4.
Mass spectrometry revealed that the molecular weight was 484.55 with m/e=485, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－９を合成した。
マススペクトル分析の結果、分子量４８４．５５に対してｍ／ｅ＝４８５であり、目的物であると同定した。 (Synthesis Example 9) Synthesis of BH1-9 BH1-9 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 484.55 with m/e=485, and the product was identified as the target substance.
（合成実施例１０）ＢＨ１－１０の合成
下記合成経路で、ＢＨ１－１０を合成した。
ＢＨ１－１の合成において、中間体２の代わりに中間体１０を用いた以外は同様の方法で合成し、ＢＨ１－１０を白色固体（１．２５ｇ、収率３２％）として得た。
マススペクトル分析の結果、分子量５７０．６９に対してｍ／ｅ＝５７１であり、目的物であると同定した。 (Synthesis Example 10) Synthesis of BH1-10 BH1-10 was synthesized according to the following synthesis route.
BH1-10 was obtained as a white solid (1.25 g, yield 32%) in the same manner as in the synthesis of BH1-1, except that intermediate 10 was used instead of intermediate 2.
Mass spectrometry revealed that the molecular weight was 570.69 with m/e=571, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－１０を合成した。
マススペクトル分析の結果、分子量５７０．６９に対してｍ／ｅ＝５７１であり、目的物であると同定した。 (Synthesis Example 10) Synthesis of BH1-10 BH1-10 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 570.69 with m/e=571, and the product was identified as the target substance.
（合成実施例１１）ＢＨ１－１１の合成
下記合成経路で、ＢＨ１－１１を合成した。
中間体１１（５．０ｇ）をジクロロメタン（３００ｍＬ）に加え、ピリジン（２．７８ｇ）をさらに加えてから氷冷して撹拌した。次いで、トリフルオロメタンスルホン酸無水物（５．９５ｇ）を滴下して、滴下終了後に室温で３時間撹拌した。水を加えて有機相を分取した後、溶媒を留去して得られた粗生成物をシリカゲルカラムクロマトグラフィーにより精製することで、中間体１２（４．５ｇ、収率６１％）を得た。この中間体１２を使って、ＢＨ１－１の合成における方法と同様に合成を実施することで、ＢＨ１－１１を白色固体（３．９ｇ、収率７７％）として得た。
マススペクトル分析の結果、分子量４６８．５５に対してｍ／ｅ＝４６９であり、目的物であると同定した。 (Synthesis Example 11) Synthesis of BH1-11 BH1-11 was synthesized according to the following synthesis route.
Intermediate 11 (5.0 g) was added to dichloromethane (300 mL), pyridine (2.78 g) was further added, and the mixture was stirred under ice cooling. Next, trifluoromethanesulfonic anhydride (5.95 g) was added dropwise, and after the completion of the dropwise addition, the mixture was stirred at room temperature for 3 hours. Water was added to separate the organic phase, and the solvent was distilled off to obtain a crude product, which was purified by silica gel column chromatography to obtain intermediate 12 (4.5 g, yield 61%). This intermediate 12 was used to perform synthesis in the same manner as in the synthesis of BH1-1, to obtain BH1-11 as a white solid (3.9 g, yield 77%).
Mass spectrometry revealed that the molecular weight was 468.55 with m/e=469, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－１１を合成した。
マススペクトル分析の結果、分子量４６８．５５に対してｍ／ｅ＝４６９であり、目的物であると同定した。 (Synthesis Example 11) Synthesis of BH1-11 BH1-11 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 468.55 with m/e=469, and the product was identified as the target substance.
（合成実施例１２）ＢＨ１－１２の合成
下記合成経路で、ＢＨ１－１２を合成した。
ＢＨ１－１の合成において、中間体２の代わりに中間体１３を用いた以外は同様の方法で合成し、ＢＨ１－１２を白色固体（１．３８ｇ、収率４３％）として得た。
マススペクトル分析の結果、分子量４７７．６１に対してｍ／ｅ＝４７８であり、目的物であると同定した。 (Synthesis Example 12) Synthesis of BH1-12 BH1-12 was synthesized according to the following synthesis route.
BH1-12 was obtained as a white solid (1.38 g, yield 43%) in the same manner as in the synthesis of BH1-1, except that intermediate 13 was used instead of intermediate 2.
Mass spectrometry revealed that the molecular weight was 477.61 with m/e=478, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－１２を合成した。
マススペクトル分析の結果、分子量４７７．６１に対してｍ／ｅ＝４７８であり、目的物であると同定した。 (Synthesis Example 12) Synthesis of BH1-12 BH1-12 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 477.61 with m/e=478, and the product was identified as the target substance.
（合成実施例１３）ＢＨ１－１３の合成
下記合成経路で、ＢＨ１－１３を合成した。
ＢＨ１－１の合成において、中間体２の代わりに中間体１４を用いた以外は同様の方法で合成し、ＢＨ１－１３を白色固体（１．６１ｇ、収率４７％）として得た。
マススペクトル分析の結果、分子量５０５．６６に対してｍ／ｅ＝５０６であり、目的物であると同定した。 (Synthesis Example 13) Synthesis of BH1-13 BH1-13 was synthesized according to the following synthesis route.
BH1-13 was obtained as a white solid (1.61 g, yield 47%) in the same manner as in the synthesis of BH1-1, except that intermediate 14 was used instead of intermediate 2.
Mass spectrometry revealed that the molecular weight was 505.66 with m/e=506, and the product was identified as the target substance.
下記合成経路で、ＢＨ１－１３を合成した。
マススペクトル分析の結果、分子量５０５．６６に対してｍ／ｅ＝５０６であり、目的物であると同定した。 (Synthesis Example 13) Synthesis of BH1-13 BH1-13 was synthesized according to the following synthesis route.
Mass spectrometry revealed that the molecular weight was 505.66 with m/e=506, and the product was identified as the target substance.
上記に本発明の実施形態及び／又は実施例を幾つか詳細に説明したが、当業者は、本発明の新規な教示及び効果から実質的に離れることなく、これら例示である実施形態及び／又は実施例に多くの変更を加えることが容易である。従って、これらの多くの変更は本発明の範囲に含まれる。
この明細書に記載の文献、及び本願のパリ条約による優先権の基礎となる出願の内容を全て援用する。 Although some embodiments and/or examples of the present invention have been described in detail above, those skilled in the art can easily make many modifications to these exemplary embodiments and/or examples without substantially departing from the novel teachings and advantages of the present invention, and therefore many such modifications are within the scope of the present invention.
The contents of all documents cited in this specification and of the application from which this application claims priority under the Paris Convention are incorporated by reference in their entirety.
この明細書に記載の文献、及び本願のパリ条約による優先権の基礎となる出願の内容を全て援用する。 Although some embodiments and/or examples of the present invention have been described in detail above, those skilled in the art can easily make many modifications to these exemplary embodiments and/or examples without substantially departing from the novel teachings and advantages of the present invention, and therefore many such modifications are within the scope of the present invention.
The contents of all documents cited in this specification and of the application from which this application claims priority under the Paris Convention are incorporated by reference in their entirety.
Claims (41)
- 下記式（１）で表される化合物。
Ｒ１０１～Ｒ１０５のうち１つは、下記式（Ａ１）で表される基と結合する単結合である。
ＬＡ１は、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のビフェニルジイル基、
置換もしくは無置換のターフェニルジイル基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のフェナントリルジイル基、
置換もしくは無置換のベンゾフェナントリルジイル基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のクリセンジイル基、
置換もしくは無置換のベンゾクリセンジイル基、
置換もしくは無置換のトリフェニレンジイル基、
置換もしくは無置換のベンゾトリフェニレンジイル基、
置換もしくは無置換のフルオレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、
置換もしくは無置換のジベンゾフルオレンジイル基、
置換もしくは無置換のナフトフルオレンジイル基、
置換もしくは無置換のフルオランテンジイル基、
置換もしくは無置換のベンゾフルオランテンジイル基、
置換もしくは無置換のペリレンジイル基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ１は、
置換もしくは無置換のフェニル基、
置換もしくは無置換のビフェニル基、
置換もしくは無置換のターフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のフェナントリル基、
置換もしくは無置換のベンゾフェナントリル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のクリセニル基、
置換もしくは無置換のベンゾクリセニル基、
置換もしくは無置換のトリフェニレニル基、
置換もしくは無置換のベンゾトリフェニレニル基、
置換もしくは無置換のフルオレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトフルオレニル基、
置換もしくは無置換のフルオランテニル基、
置換もしくは無置換のベンゾフルオランテニル基、
置換もしくは無置換のペリレニル基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ１は０～３の整数である。
ｎＡ１が０である場合、（ＬＡ１）ｎＡ１は単結合である。
ｎＡ１が２又は３である場合、複数のＬＡ１は互いに直列状に連結し、ＡｒＡ１は、ジナフトフラン骨格から最も離れたＬＡ１に結合する。複数のＬＡ１は同一でもよく、異なってもよい。）
Ｒ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではないＲ１０１～Ｒ１０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ１０６～Ｒ１１２、及び前記式（Ａ１）で表される基と結合する単結合ではなく、互いに結合しないＲ１０１～Ｒ１０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ１）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。］ A compound represented by the following formula (1):
One of R 101 to R 105 is a single bond bonded to a group represented by the following formula (A1).
L A1 is,
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted biphenyldiyl group,
a substituted or unsubstituted terphenyldiyl group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted phenanthryldiyl group,
a substituted or unsubstituted benzophenanthryldiyl group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
a substituted or unsubstituted chrysenediyl group;
a substituted or unsubstituted benzochrysenediyl group,
a substituted or unsubstituted triphenylenediyl group,
a substituted or unsubstituted benzotriphenylenediyl group,
a substituted or unsubstituted fluorenediyl group;
a substituted or unsubstituted benzofluorenediyl group,
a substituted or unsubstituted dibenzofluorenediyl group,
a substituted or unsubstituted naphthofluorenediyl group,
a substituted or unsubstituted fluoranthene diyl group;
a substituted or unsubstituted benzofluoranthene diyl group;
It is a substituted or unsubstituted perylenediyl group, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted biphenyl group,
a substituted or unsubstituted terphenyl group;
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted benzophenanthryl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted chrysenyl group;
a substituted or unsubstituted benzochrysenyl group,
a substituted or unsubstituted triphenylenyl group,
a substituted or unsubstituted benzotriphenylenyl group,
a substituted or unsubstituted fluorenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
a substituted or unsubstituted naphthofluorenyl group,
a substituted or unsubstituted fluoranthenyl group;
a substituted or unsubstituted benzofluoranthenyl group;
It is a substituted or unsubstituted perylenyl group, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA1 is an integer of 0 to 3.
When nA1 is 0, (L A1 ) nA1 is a single bond.
When nA1 is 2 or 3, multiple L A1 are linked to each other in series, and Ar A1 is bonded to the L A1 that is the most distant from the dinaphthofuran skeleton. Multiple L A1 may be the same or different.
One or more pairs of adjacent two or more of R 106 to R 112 and R 101 to R 105 that are not a single bond bonded to the group represented by formula (A1) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
R 106 to R 112 which are not bonded to each other, and R 101 to R 105 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A1) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A1).
The substituents in the term "substituted or unsubstituted" are:
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, each of the two or more R 41 to R 45 and R 49 to R 51 may be the same or different.] - Ｒ１０２～Ｒ１０５のうち１つが、前記式（Ａ１）で表される基と結合する単結合である、請求項１に記載の化合物。 The compound according to claim 1, wherein one of R 102 to R 105 is a single bond bonded to the group represented by formula (A1).
- Ｒ１０２、Ｒ１０３、及びＲ１０５のうち１つが、前記式（Ａ１）で表される基と結合する単結合である、請求項１又は２に記載の化合物。 The compound according to claim 1 or 2, wherein one of R 102 , R 103 , and R 105 is a single bond bonded to the group represented by formula (A1).
- ＬＡ１が、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である、請求項１～３のいずれかに記載の化合物。 L A1 is
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
The compound according to any one of claims 1 to 3, which is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group. - ＬＡ１が、
単結合、又は
置換もしくは無置換のフェニレン基である、請求項１～４のいずれかに記載の化合物。 L A1 is
The compound according to any one of claims 1 to 4, which is a single bond, or a substituted or unsubstituted phenylene group. - ＡｒＡ１が、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である、請求項１～５のいずれかに記載の化合物。 Ar A1 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group; a substituted or unsubstituted pyrenyl group;
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
The compound according to any one of claims 1 to 5, which is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group. - 前記式（Ａ１）で表される基が、下記式（Ａ１－１）～式（Ａ１－７）のいずれかで表される基である、請求項１～６のいずれかに記載の化合物。
ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ The compound according to any one of claims 1 to 6, wherein the group represented by formula (A1) is a group represented by any one of the following formulas (A1-1) to (A1-7):
R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.] - 前記式（１）で表される化合物が、下記式（１－１）～式（１－３）のいずれかで表される化合物である、請求項１～７のいずれかに記載の化合物。
- 前記式（１）で表される化合物が、下記式（１－１１）～式（１－１９）のいずれかで表される化合物である、請求項１～８のいずれかに記載の化合物。
ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ The compound according to any one of claims 1 to 8, wherein the compound represented by formula (1) is a compound represented by any one of the following formulas (1-11) to (1-19):
R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.] - 単結合ではないＲ１０１～Ｒ１１２が、水素原子である、請求項１～９のいずれかに記載の化合物。 The compound according to any one of claims 1 to 9, wherein R 101 to R 112 that are not single bonds are hydrogen atoms.
- ＲＡ１１～ＲＡ１９、ＲＡ２１～ＲＡ３２、ＲＡ４１～ＲＡ５１、ＲＡ６１～ＲＡ７３、ＲＡ８１～ＲＡ８９、及びＲＡ９１～ＲＡ９９が、それぞれ独立に、
水素原子、
メチル基、
フェニル基、又は
ナフチル基である、請求項７～１０のいずれかに記載の化合物。 R A11 to R A19 , R A21 to R A32 , R A41 to R A51 , R A61 to R A73 , R A81 to R A89 , and R A91 to R A99 are each independently
Hydrogen atoms,
Methyl group,
The compound according to any one of claims 7 to 10, which is a phenyl group or a naphthyl group. - 下記式（２）で表される化合物。
Ｒ２０１～Ｒ２０５のうち１つは、下記式（Ａ２）で表される基と結合する単結合である。
ＬＡ２は、
単結合、
置換もしくは無置換の環形成炭素数６～２１のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基である。
ＡｒＡ２は、
５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基である。
ｎＡ２は０～３の整数である。
ｎＡ２が０である場合、（ＬＡ２）ｎＡ２は単結合である。
ｎＡ２が２又は３である場合、複数のＬＡ２は互いに直列状に連結し、ＡｒＡ２は、ジナフトフラン骨格から最も離れたＬＡ２に結合する。複数のＬＡ２は同一でもよく、異なってもよい。）
Ｒ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではないＲ２０１～Ｒ２０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ２０６～Ｒ２１２、及び前記式（Ａ２）で表される基と結合する単結合ではなく、互いに結合しないＲ２０１～Ｒ２０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ２）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。
「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ４１）（Ｒ４２）（Ｒ４３）、
－Ｃ（＝Ｏ）Ｒ４４、－ＣＯＯＲ４５、
－Ｇｅ（Ｒ４９）（Ｒ５０）（Ｒ５１）、
ヒドロキシ基、
シアノ基、
ニトロ基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ４１～Ｒ４５及びＲ４９～Ｒ５１が２以上存在する場合、２以上のＲ４１～Ｒ４５及びＲ４９～Ｒ５１のそれぞれは同一でもよく、異なっていてもよい。
ただし、ＬＡ２における、置換もしくは無置換の環形成炭素数６～２１のアリーレン基、及び置換もしくは無置換の環形成原子数５～３０の２価の含酸素複素環基、並びにＡｒＡ２における、５個以下の環で構成される置換もしくは無置換の環形成炭素数６～３０のアリール基、及び置換もしくは無置換の環形成原子数５～３０の１価の含酸素複素環基は、それぞれ下記式（Ｔ１）を満たす基である。
Ｔ１＞１．８１ｅＶ・・・（Ｔ１）
（式（Ｔ１）中、Ｔ１は、当該基の三重項エネルギーである。）］ A compound represented by the following formula (2):
One of R 201 to R 205 is a single bond bonded to a group represented by the following formula (A2).
L A2 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
Ar A2 is
It is a substituted or unsubstituted aryl group consisting of 5 or less rings and having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.
nA2 is an integer from 0 to 3.
When nA2 is 0, (L A2 ) nA2 is a single bond.
When nA2 is 2 or 3, multiple L A2 are linked to each other in series, and Ar A2 is bonded to the L A2 that is the most distant from the dinaphthofuran skeleton. Multiple L A2 may be the same or different.
Among R 206 to R 212 and R 201 to R 205 that are not single bonds bonded to the group represented by formula (A2), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 206 to R 212 which are not bonded to each other, and R 201 to R 205 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A2) each independently represent:
It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and not the same as the group represented by formula (A2).
In the case of "substituted or unsubstituted", the substituents are
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 41 )(R 42 )(R 43 ),
-C(=O)R 44 , -COOR 45 ,
-Ge(R 49 )(R 50 )(R 51 ),
Hydroxy groups,
Cyano group,
Nitro group,
It is an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 41 to R 45 and R 49 to R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 41 to R 45 and R 49 to R 51 are present, each of the two or more R 41 to R 45 and R 49 to R 51 may be the same or different.
However, the substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and the substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in L A2 , and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms which are composed of 5 or less rings in Ar A2 are each a group which satisfies the following formula (T1).
T 1 >1.81eV...(T1)
(In formula (T1), T1 is the triplet energy of the group.) - Ｒ２０２～Ｒ２０５のうち１つが、前記式（Ａ２）で表される基と結合する単結合である、請求項１２に記載の化合物。 The compound according to claim 12, wherein one of R 202 to R 205 is a single bond bonded to the group represented by formula (A2).
- Ｒ２０２、Ｒ２０３、及びＲ２０５のうち１つが、前記式（Ａ２）で表される基と結合する単結合である、請求項１２又は１３に記載の化合物。 The compound according to claim 12 or 13, wherein one of R 202 , R 203 and R 205 is a single bond bonded to the group represented by formula (A2).
- ＬＡ２が、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である、請求項１２～１４のいずれかに記載の化合物。 L A2 is
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
The compound according to any one of claims 12 to 14, which is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group. - ＬＡ２が、
単結合、又は
置換もしくは無置換のフェニレン基である、請求項１２～１５のいずれかに記載の化合物。 L A2 is
The compound according to any one of claims 12 to 15, which is a single bond, or a substituted or unsubstituted phenylene group. - ＡｒＡ２が、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である、請求項１２～１６のいずれかに記載の化合物。 Ar A2 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
The compound according to any one of claims 12 to 16, which is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group. - 前記式（Ａ２）で表される基が、下記式（Ａ２－１）～式（Ａ２－７）のいずれかで表される基である、請求項１２～１７のいずれかに記載の化合物。
ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ The compound according to any one of claims 12 to 17, wherein the group represented by formula (A2) is a group represented by any one of the following formulas (A2-1) to (A2-7):
R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.] - 前記式（２）で表される化合物が、下記式（２－１）～式（２－３）のいずれかで表される化合物である、請求項１２～１８のいずれかに記載の化合物。
- 前記式（２）で表される化合物が、下記式（２－１１）～式（２－１９）のいずれかで表される化合物である、請求項１２～１９のいずれかに記載の化合物。
ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～１３のアリール基、又は
環形成原子数５～５０の１価の複素環基である。］ The compound according to any one of claims 12 to 19, wherein the compound represented by formula (2) is a compound represented by any one of the following formulas (2-11) to (2-19):
R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.] - 単結合ではないＲ２０１～Ｒ２１２が、水素原子である、請求項１２～２０のいずれかに記載の化合物。 The compound according to any one of claims 12 to 20, wherein R 201 to R 212 that are not single bonds are hydrogen atoms.
- ＲＡ１１１～ＲＡ１１９、ＲＡ１２１～ＲＡ１３２、ＲＡ１４１～ＲＡ１５１、ＲＡ１６１～ＲＡ１７３、ＲＡ１８１～ＲＡ１８９、及びＲＡ１９１～ＲＡ１９９が、それぞれ独立に、
水素原子、
メチル基、
フェニル基、又は
ナフチル基である、請求項１８～２１のいずれかに記載の化合物。 R A111 to R A119 , R A121 to R A132 , R A141 to R A151 , R A161 to R A173 , R A181 to R A189 , and R A191 to R A199 are each independently
Hydrogen atoms,
Methyl group,
The compound according to any one of claims 18 to 21, which is a phenyl group or a naphthyl group. - 有機エレクトロルミネッセンス素子用材料である、請求項１～２２のいずれかに記載の化合物。 The compound according to any one of claims 1 to 22, which is a material for an organic electroluminescence device.
- 陰極と、
陽極と、
前記陰極及び前記陽極の間に配置された発光層と、を有し、
前記発光層は第１の発光層及び第２の発光層を含み、
前記第１の発光層が、下記式（３）で表される化合物を含む、有機エレクトロルミネッセンス素子。
Ｒ３０１～Ｒ３０５のうち１つは、下記式（Ａ３）で表される基と結合する単結合である。
ＬＡ３は、
単結合、
置換もしくは無置換の環形成炭素数６～３０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～３０の２価の複素環基である。
ＡｒＡ３は、
置換もしくは無置換の環形成炭素数６～３０のアリール基、又は
置換もしくは無置換の環形成原子数５～３０の１価の複素環基である。
ｎＡ３は０～３の整数である。
ｎＡ３が０である場合、（ＬＡ３）ｎＡ３は単結合である。
ｎＡ３が２又は３である場合、複数のＬＡ３は互いに直列状に連結し、ＡｒＡ３は、ジナフトフラン骨格から最も離れたＬＡ３に結合する。複数のＬＡ３は同一でもよく、異なってもよい。）
Ｒ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではないＲ３０１～Ｒ３０５のうち隣接する２つ以上からなる組の１組以上は、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。
互いに結合しないＲ３０６～Ｒ３１２、及び前記式（Ａ３）で表される基と結合する単結合ではなく、互いに結合しないＲ３０１～Ｒ３０５は、それぞれ独立に、
水素原子、又は
前記式（Ａ３）で表される基と同一ではない置換もしくは無置換の環形成炭素数６～３０のアリール基である。］ A cathode;
An anode;
a light-emitting layer disposed between the cathode and the anode;
the light-emitting layer includes a first light-emitting layer and a second light-emitting layer,
The organic electroluminescence device, wherein the first light-emitting layer contains a compound represented by the following formula (3):
One of R 301 to R 305 is a single bond bonded to a group represented by the following formula (A3).
L A3 is,
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
Ar A3 is
It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.
nA3 is an integer from 0 to 3.
When nA3 is 0, (L A3 ) nA3 is a single bond.
When nA3 is 2 or 3, multiple L A3 are linked to each other in series, and Ar A3 is bonded to the L A3 that is the most distant from the dinaphthofuran skeleton. Multiple L A3 may be the same or different.
Among R 306 to R 312 and R 301 to R 305 which are not single bonds bonded to the group represented by formula (A3), one or more pairs of adjacent two or more pairs are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
R 306 to R 312 which are not bonded to each other, and R 301 to R 305 which are not bonded to each other and are not a single bond bonded to the group represented by formula (A3) each independently represent:
a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that is not the same as the group represented by formula (A3).] - Ｒ３０２～Ｒ３０５のうち１つが、前記式（Ａ３）で表される基と結合する単結合である、請求項２４に記載の有機エレクトロルミネッセンス素子。 25. The organic electroluminescence device according to claim 24, wherein one of R 302 to R 305 is a single bond bonded to the group represented by formula (A3).
- Ｒ３０２、Ｒ３０３、及びＲ３０５のうち１つが、前記式（Ａ３）で表される基と結合する単結合である、請求項２４又は２５に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to claim 24 or 25, wherein one of R 302 , R 303 , and R 305 is a single bond bonded to the group represented by formula (A3).
- ＬＡ３が、
単結合、
置換もしくは無置換のフェニレン基、
置換もしくは無置換のナフチレン基、
置換もしくは無置換のベンズアントラセンジイル基、
置換もしくは無置換のピレンジイル基、
置換もしくは無置換のベンゾフルオレンジイル基、又は
置換もしくは無置換のジベンゾフルオレンジイル基である、請求項２４～２６のいずれかに記載の有機エレクトロルミネッセンス素子。 L A3 ,
Single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted benzanthracenediyl group,
a substituted or unsubstituted pyrenediyl group,
The organic electroluminescence device according to any one of claims 24 to 26, wherein the group is a substituted or unsubstituted benzofluorenediyl group, or a substituted or unsubstituted dibenzofluorenediyl group. - ＬＡ３が、
単結合、又は
置換もしくは無置換のフェニレン基である、請求項２４～２７のいずれかに記載の有機エレクトロルミネッセンス素子。 L A3 ,
The organic electroluminescence device according to any one of claims 24 to 27, wherein the group is a single bond, or a substituted or unsubstituted phenylene group. - ＡｒＡ３が、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のベンズアントラセニル基、
置換もしくは無置換のピレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフルオレニル基、
置換もしくは無置換のナフトベンゾフラニル基、又は
置換もしくは無置換のベンゾキサンテニル基である、請求項２４～２８のいずれかに記載の有機エレクトロルミネッセンス素子。 Ar A3 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted benzanthracenyl group,
a substituted or unsubstituted pyrenyl group,
a substituted or unsubstituted benzofluorenyl group,
a substituted or unsubstituted dibenzofluorenyl group,
The organic electroluminescence device according to any one of claims 24 to 28, wherein the group is a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted benzoxanthenyl group. - 前記式（Ａ３）で表される基が、下記式（Ａ３－１）～式（Ａ３－７）のいずれかで表される基である、請求項２４～２９のいずれかに記載の有機エレクトロルミネッセンス素子。
ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルコキシ基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９４１）（Ｒ９４２）（Ｒ９４３）、
－Ｃ（＝Ｏ）Ｒ９４４、－ＣＯＯＲ９４５、
－Ｓ（＝Ｏ）２Ｒ９４６、
－Ｐ（＝Ｏ）（Ｒ９４７）（Ｒ９４８）、
－Ｇｅ（Ｒ９４９）（Ｒ９５０）（Ｒ９５１）、
－Ｎ（Ｒ９５２）（Ｒ９５３）、
ヒドロキシ基、
ハロゲン原子、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３が２以上存在する場合、２以上のＲ９４１～Ｒ９５３のそれぞれは同一でもよく、異なっていてもよい。］ The organic electroluminescence device according to any one of claims 24 to 29, wherein the group represented by the formula (A3) is a group represented by any one of the following formulas (A3-1) to (A3-7):
R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkoxy group having 1 to 50 carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 941 )(R 942 )(R 943 ),
-C(=O)R 944 , -COOR 945 ,
-S(=O) 2 R 946 ,
-P(=O)(R 947 )(R 948 ),
-Ge(R 949 )(R 950 )(R 951 ),
-N(R 952 )(R 953 ),
Hydroxy groups,
Halogen atoms,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 941 to R 953 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 941 to R 953 are present, each of the two or more R 941 to R 953 may be the same or different.] - 前記式（３）で表される化合物が、下記式（３－１）～式（３－３）のいずれかで表される化合物である、請求項２４～３０のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記式（３）で表される化合物が、下記式（３－１１）～式（３－１９）のいずれかで表される化合物である、請求項２４～３１のいずれかに記載の有機エレクトロルミネッセンス素子。
ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９は、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
炭素数１～５０のハロアルキル基、
炭素数２～５０のアルケニル基、
炭素数２～５０のアルキニル基、
環形成炭素数３～５０のシクロアルキル基、
炭素数１～５０のアルコキシ基、
炭素数１～５０のアルキルチオ基、
環形成炭素数６～５０のアリールオキシ基、
環形成炭素数６～５０のアリールチオ基、
炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９４１）（Ｒ９４２）（Ｒ９４３）、
－Ｃ（＝Ｏ）Ｒ９４４、－ＣＯＯＲ９４５、
－Ｓ（＝Ｏ）２Ｒ９４６、
－Ｐ（＝Ｏ）（Ｒ９４７）（Ｒ９４８）、
－Ｇｅ（Ｒ９４９）（Ｒ９５０）（Ｒ９５１）、
－Ｎ（Ｒ９５２）（Ｒ９５３）、
ヒドロキシ基、
ハロゲン原子、
シアノ基、
ニトロ基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３は、それぞれ独立に、水素原子、炭素数１～５０のアルキル基、環形成炭素数６～５０のアリール基、又は環形成原子数５～５０の１価の複素環基である。
Ｒ９４１～Ｒ９５３が２以上存在する場合、２以上のＲ９４１～Ｒ９５３のそれぞれは同一でもよく、異なっていてもよい。］ The organic electroluminescence device according to any one of claims 24 to 31, wherein the compound represented by the formula (3) is a compound represented by any one of the following formulas (3-11) to (3-19):
R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
a haloalkyl group having 1 to 50 carbon atoms,
an alkenyl group having 2 to 50 carbon atoms,
an alkynyl group having 2 to 50 carbon atoms,
a cycloalkyl group having 3 to 50 ring carbon atoms,
an alkoxy group having 1 to 50 carbon atoms,
an alkylthio group having 1 to 50 carbon atoms,
an aryloxy group having 6 to 50 ring carbon atoms,
an arylthio group having 6 to 50 ring carbon atoms,
an aralkyl group having 7 to 50 carbon atoms,
-Si(R 941 )(R 942 )(R 943 ),
-C(=O)R 944 , -COOR 945 ,
-S(=O) 2 R 946 ,
-P(=O)(R 947 )(R 948 ),
-Ge(R 949 )(R 950 )(R 951 ),
-N(R 952 )(R 953 ),
Hydroxy groups,
Halogen atoms,
Cyano group,
Nitro group,
It is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
R 941 to R 953 each independently represent a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more of R 941 to R 953 are present, each of the two or more R 941 to R 953 may be the same or different.] - 単結合ではないＲ３０１～Ｒ３１２が、水素原子である、請求項２４～３２のいずれかに記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to any one of claims 24 to 32, wherein R 301 to R 312 that are not single bonds are hydrogen atoms.
- ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、ＲＡ２６１～ＲＡ２７３、ＲＡ２８１～ＲＡ２８９、及びＲＡ２９１～ＲＡ２９９が、それぞれ独立に、
水素原子、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、又は
環形成原子数５～５０の１価の複素環基である、請求項３０～３３のいずれかに記載の有機エレクトロルミネッセンス素子。 R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , R A261 to R A273 , R A281 to R A289 , and R A291 to R A299 are each independently
Hydrogen atoms,
an alkyl group having 1 to 50 carbon atoms,
34. The organic electroluminescence device according to claim 30, wherein the ring is an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms. - ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、及びＲＡ２６１～ＲＡ２７３が、それぞれ独立に、
水素原子、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、又は
環形成原子数５～１８の１価の複素環基である、請求項３０～３４のいずれかに記載の有機エレクトロルミネッセンス素子。 R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , and R A261 to R A273 are each independently
Hydrogen atoms,
an alkyl group having 1 to 18 carbon atoms,
35. The organic electroluminescence device according to claim 30, wherein the ring is an aryl group having 6 to 18 ring carbon atoms, or a monovalent heterocyclic group having 5 to 18 ring atoms. - ＲＡ２１１～ＲＡ２１９、ＲＡ２２１～ＲＡ２３２、ＲＡ２４１～ＲＡ２５１、及びＲＡ２６１～ＲＡ２７３が、それぞれ独立に、
水素原子、
メチル基、
フェニル基、又は
ナフチル基である、請求項３０～３５のいずれかに記載の有機エレクトロルミネッセンス素子。 R A211 to R A219 , R A221 to R A232 , R A241 to R A251 , and R A261 to R A273 are each independently
Hydrogen atoms,
Methyl group,
The organic electroluminescence device according to any one of claims 30 to 35, wherein the group is a phenyl group or a naphthyl group. - 前記発光層が、前記陽極の側から前記第１の発光層と前記第２の発光層とをこの順で有する、請求項２４～３６のいずれかに記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence element according to any one of claims 24 to 36, wherein the light-emitting layer has the first light-emitting layer and the second light-emitting layer in this order from the anode side.
- 前記第１の発光層と、前記第２の発光層とが、直接隣接する、請求項２４～３７のいずれかに記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence element according to any one of claims 24 to 37, wherein the first light-emitting layer and the second light-emitting layer are directly adjacent to each other.
- 前記陽極と前記発光層との間に正孔輸送層を有する、請求項２４～３８のいずれかに記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to any one of claims 24 to 38, comprising a hole transport layer between the anode and the light-emitting layer.
- 前記陰極と前記発光層との間に電子輸送層を有する、請求項２４～３９のいずれに記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to any one of claims 24 to 39, comprising an electron transport layer between the cathode and the light-emitting layer.
- 請求項２４～４０のいずれかに記載の有機エレクトロルミネッセンス素子を備える電子機器。 An electronic device comprising an organic electroluminescence element according to any one of claims 24 to 40.
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