JP2022548195A - ヘテロ環化合物およびこれを含む有機発光素子 - Google Patents
ヘテロ環化合物およびこれを含む有機発光素子 Download PDFInfo
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- JP2022548195A JP2022548195A JP2022504171A JP2022504171A JP2022548195A JP 2022548195 A JP2022548195 A JP 2022548195A JP 2022504171 A JP2022504171 A JP 2022504171A JP 2022504171 A JP2022504171 A JP 2022504171A JP 2022548195 A JP2022548195 A JP 2022548195A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 52
- 239000012044 organic layer Substances 0.000 claims abstract description 28
- 239000010410 layer Substances 0.000 claims description 160
- 239000000463 material Substances 0.000 claims description 102
- 125000004432 carbon atom Chemical group C* 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 71
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 239000000126 substance Substances 0.000 claims description 50
- 125000000732 arylene group Chemical group 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 33
- 229910052805 deuterium Inorganic materials 0.000 claims description 32
- 230000005525 hole transport Effects 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000005549 heteroarylene group Chemical group 0.000 claims description 21
- 125000003367 polycyclic group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
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- 125000003277 amino group Chemical group 0.000 claims description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- -1 1-methylpentyl group Chemical group 0.000 description 70
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 238000002347 injection Methods 0.000 description 29
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- 239000012153 distilled water Substances 0.000 description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000000151 deposition Methods 0.000 description 7
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920000767 polyaniline Polymers 0.000 description 6
- 125000006835 (C6-C20) arylene group Chemical group 0.000 description 5
- 125000006761 (C6-C60) arylene group Chemical group 0.000 description 5
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
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- 125000003003 spiro group Chemical group 0.000 description 5
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 5
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000000434 field desorption mass spectrometry Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 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 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 239000000203 mixture Substances 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- 238000005406 washing Methods 0.000 description 2
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BHSJHAIXABJMSL-UHFFFAOYSA-N 1,1'-spirobi[benzo[b][1]benzosilole] Chemical compound C12=C3C=CC=CC3=[SiH]C2=CC=CC11C2=C3C=CC=CC3=[SiH]C2=CC=C1 BHSJHAIXABJMSL-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
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- FQJZPYXGPYJJIH-UHFFFAOYSA-N 1-bromonaphthalen-2-ol Chemical compound C1=CC=CC2=C(Br)C(O)=CC=C21 FQJZPYXGPYJJIH-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- DSQMLISBVUTWJB-UHFFFAOYSA-N 2,6-diphenylaniline Chemical group NC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 DSQMLISBVUTWJB-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QVSJCRDHNCCXFC-UHFFFAOYSA-N 3-[9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]carbazol-3-yl]-9-phenylcarbazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC(=CC=2)N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)=N1 QVSJCRDHNCCXFC-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- RFTRFDMRINNTSI-UHFFFAOYSA-N 9,9-dimethyl-n-phenylfluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1NC1=CC=CC=C1 RFTRFDMRINNTSI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YUIVYVFBRORXIO-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2 Chemical group C1(=CC=CC=C1)NC1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2 YUIVYVFBRORXIO-UHFFFAOYSA-N 0.000 description 1
- XUUDZMMIKPJQBD-UHFFFAOYSA-N CC1(C2=CC=CC=C2C=2C=CC(=CC12)NC1=CC=CC=C1)C.CC1(C2=CC=CC=C2C=2C=CC(=CC12)NC1=CC=CC=C1)C Chemical compound CC1(C2=CC=CC=C2C=2C=CC(=CC12)NC1=CC=CC=C1)C.CC1(C2=CC=CC=C2C=2C=CC(=CC12)NC1=CC=CC=C1)C XUUDZMMIKPJQBD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
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Abstract
Description
前記化学式1において、
L1~L4は、互いに同一または異なり、それぞれ独立して、直接結合;置換もしくは非置換の炭素数6~60のアリーレン基;または置換もしくは非置換の炭素数2~60のヘテロアリーレン基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換の炭素数6~40のアリール基;または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
R1およびR2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換の炭素数1~20のアルキル基;置換もしくは非置換の炭素数6~40のアリール基;または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
X1~X3は、互いに同一または異なり、それぞれ独立して、水素;重水素;置換もしくは非置換の炭素数6~20のアリール基、または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
k、l、mおよびnは、それぞれ独立して、1~3の整数であり、
aは、1~6の整数であり、
bは、1~3の整数であり、
cは、1~4の整数であり、
k、l、m、n、a、bおよびcが2以上の場合、括弧内の置換基は、互いに同一または異なる。
で表されるフェニル基において重水素の含有量20%というのは、フェニル基が有し得る置換基の総数は5(式中のT1)個であり、そのうち重水素の個数が1(式中のT2)である場合、20%で表される。すなわち、フェニル基において重水素の含有量20%というのは、下記構造式で表されてもよい。
本明細書において、前記ヘテロアリール基は、ヘテロ原子としてS、O、Se、N、またはSiを含み、炭素数2~60の単環もしくは多環を含み、他の置換基によって追加的に置換されていてもよい。ここで、前記多環とは、ヘテロアリール基が他の環基と直接連結または縮合された基を意味する。ここで、他の環基とは、ヘテロアリール基であってもよいが、他の種類の環基、例えば、シクロアルキル基、ヘテロシクロアルキル基、アリール基などであってもよい。前記ヘテロアリール基の炭素数は2~60、具体的には2~40、さらに具体的には3~25であってもよい。前記ヘテロアリール基の具体例としては、ピリジル基、ピロリル基、ピリミジル基、ピリダジニル基、フラニル基、チオフェン基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、フラザニル基、オキサジアゾリル基、チアジアゾリル基、ジチアゾリル基、テトラゾリル基、ピラニル基、チオピラニル基、ジアジニル基、オキサジニル基、チアジニル基、ジオキシニル基、トリアジニル基、テトラジニル基、キノリル基、イソキノリル基、キナゾリニル基、イソキナゾリニル基、キノゾリリル基、ナフチリジル基、アクリジニル基、フェナントリジニル基、イミダゾピリジニル基、ジアザナフタレニル基、トリアザインデン基、インドリル基、インドリジニル基、ベンゾチアゾリル基、ベンズオキサゾリル基、ベンズイミダゾリル基、ベンゾチオフェン基、ベンゾフラン基、ジベンゾチオフェン基、ジベンゾフラン基、カルバゾリル基、ベンゾカルバゾリル基、ジベンゾカルバゾリル基、フェナジニル基、ジベンゾシロール基、スピロビ(ジベンゾシロール)、ジヒドロフェナジニル基、フェノキサジニル基、フェナントリジル基、イミダゾピリジニル基、チエニル基、インドロ[2,3-a]カルバゾリル基、インドロ[2,3-b]カルバゾリル基、インドリニル基、10,11-ジヒドロ-ジベンゾ[b,f]アゼピン基、9,10-ジヒドロアクリジニル基、フェナントラジニル基、フェノチアチアジニル基、フタラジニル基、ナフチリジニル基、フェナントロリニル基、ベンゾ[c][1,2,5]チアジアゾリル基、5,10-ジヒドロジベンゾ[b,e][1,4]アザシリニル、ピラゾロ[1,5-c]キナゾリニル基、ピリド[1,2-b]インダゾリル基、ピリド[1,2-a]イミダゾ[1,2-e]インドリニル基、5,11-ジヒドロインデノ[1,2-b]カルバゾリル基などが挙げられるが、これらのみに限定されるものではない。
前記化学式1において、
L1~L4は、互いに同一または異なり、それぞれ独立して、直接結合;置換もしくは非置換の炭素数6~60のアリーレン基;または置換もしくは非置換の炭素数2~60のヘテロアリーレン基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換の炭素数6~40のアリール基;または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
R1およびR2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換の炭素数1~20のアルキル基;置換もしくは非置換の炭素数6~40のアリール基;または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
X1~X3は、互いに同一または異なり、それぞれ独立して、水素;重水素;置換もしくは非置換の炭素数6~20のアリール基、または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
k、l、mおよびnは、それぞれ独立して、1~3の整数であり、
aは、1~6の整数であり、
bは、1~3の整数であり、
cは、1~4の整数であり、
k、l、m、n、a、bおよびcが2以上の場合、括弧内の置換基は、互いに同一または異なる。
また、前記化学式1の構造に多様な置換基を導入することにより、導入された置換基の固有の特性を有する化合物を合成することができる。例えば、有機発光素子の製造時に使用される正孔注入層物質、正孔輸送層物質、発光層物質、電子輸送層物質、および電荷生成層物質に主に使用される置換基を前記コア構造に導入することにより、各有機物層で要求する条件を満たす物質を合成することができる。
1-ブロモナフタレン-2-オール(1-bromonaphthalen-2-ol)(50g、224.14mmol)とフェニルボロン酸(phenylboronic acid)(28.7g、235.35mmol)を、トルエン(Toluene)500mlとエタノール(Ethanol)100ml、H2O100mlに溶かした後、Pd(PPh3)4(12.95g、11.21mmol)とK2CO3(92.93g、672.42mmol)を入れて、5時間還流撹拌した。反応完了後、反応液にメチレンクロライド(Methylene chloride、以下、MC)を入れて溶解させた後、蒸留水で抽出し、有機層を無水MgSO4で乾燥させた後、回転蒸発器で溶媒を除去した後、ジクロロメタンとヘキサンを展開溶媒としてカラムクロマトグラフィーで精製して、化合物A-2(40g、82%)を得た。
化合物A-2(40g、181.60mmol)とトリメチルアミン(trimethylamine)(20.21g、199.76mmol)を、MC400mlに溶かした後、ice bathで撹拌しながら、トリフリック無水物(triflic anhydride)(41.96g、199.76mmol)をゆっくり滴加した。その後、室温で3時間撹拌した。反応完了後、反応液にMCを入れて溶解させた後、蒸留水で抽出し、有機層を無水MgSO4で乾燥させた後、回転蒸発器で溶媒を除去した後、ジクロロメタンとヘキサンを展開溶媒としてカラムクロマトグラフィーで精製して、化合物A-3(58.2g、91%)を得た。
化合物A-3(7g、19.87mmol)と9,9-ジメチル-N-フェニル-9H-フルオレン-2-アミン(9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)(5.67g、19.87mmol)を、トルエン(Toluene)140mlに溶かした後、Pd(dba)2(1.14g、1.99mmol)、P(t-Bu)3(1.65ml、3.97mmol)、t-BuONa(3.82g、39.74mmol)を入れて、8時間還流撹拌した。反応完了後、反応液にMCを入れて溶解させた後、蒸留水で抽出し、有機層を無水MgSO4で乾燥させた後、回転蒸発器で溶媒を除去した後、ジクロロメタンとヘキサンを展開溶媒としてカラムクロマトグラフィーで精製して、化合物1(6.98g、72%)を得た。
化合物A-3(21.7g、61.52mmol)と(4-ブロモフェニル)ボロン酸((4-bromophenyl)boronic acid)(12.97g、64.60mmol)を、トルエン(Toluene)300mlとエタノール(Ethanol)60ml、H2O60mlに溶かした後、Pd(PPh3)4(3.56g、3.08mmol)とK2CO3(25.51g、184.56mmol)を入れて、2時間還流撹拌した。反応完了後、反応液にMCを入れて溶解させた後、蒸留水で抽出し、有機層を無水MgSO4で乾燥させた後、回転蒸発器で溶媒を除去した後、ジクロロメタンとヘキサンを展開溶媒としてカラムクロマトグラフィーで精製して、化合物A-4(16.35g、74%)を得た。
化合物A-4(7.14g、19.87mmol)とN-(4-(9,9-ジメチル-9H-フルオレン-2-イル)フェニル)フェナントレン-9-アミン(N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenanthrene-9-amine)(9.17g、19.87mmol)を、トルエン(Toluene)140mlに溶かした後、Pd(dba)2(1.14g、1.99mmol)、P(t-Bu)3(1.65ml、3.97mmol)、t-BuONa(3.82g、39.74mmol)を入れて、12時間還流撹拌した。反応完了後、反応液にMCを入れて溶解させた後、蒸留水で抽出し、有機層を無水MgSO4で乾燥させた後、回転蒸発器で溶媒を除去した後、ジクロロメタンとヘキサンを展開溶媒としてカラムクロマトグラフィーで精製して、化合物125(12.79g、87%)を得た。
前記製造例と同様の方法で本明細書に記載の化合物を製造し、その製造された化合物の合成確認結果を下記表3および表4に示した。下記表3は、1H NMR(DMSO、300MHz)の測定値であり、下記表4は、FD-質量分析計(FD-MS:Field desorption mass spectrometry)の測定値である。
<実験例1>
(1)有機発光素子の製造
1,500Åの厚さにITOが薄膜コーティングされたガラス基板を、蒸留水超音波洗浄した。蒸留水洗浄が終わると、アセトン、メタノール、イソプロピルアルコールなどの溶剤で超音波洗浄をし乾燥させた後、UV洗浄機でUVを用いて5分間UVO処理した。以後、基板をプラズマ洗浄機(PT)に搬送させた後、真空状態でITOの仕事関数および残膜除去のためにプラズマ処理をして、有機蒸着用熱蒸着装置に搬送した。
次いで、チャンバ内の真空度が10-6torrに到達するまで排気させた後、セルに電流を印加して2-TNATAを蒸発させて、ITO基板上に600Åの厚さの正孔注入層を蒸着した。真空蒸着装置内の他のセルに、下記のN,N’-ビス(α-ナフチル)-N,N’-ジフェニル-4,4’-ジアミン(N,N’-bis(α-naphthyl)-N,N’-diphenyl-4,4’-diamine:NPB)を入れて、セルに電流を印加して蒸発させて、正孔注入層上に300Åの厚さの正孔輸送層を蒸着した。
その上に、発光層を次のように熱真空蒸着させた。発光層は、ホストとして9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9’-phenyl-3,3’-Bi-9H-carbazoleの化合物を400Åの厚さに蒸着し、緑色燐光ドーパントはIr(ppy)3をホスト材料の重量対比7%ドーピングして蒸着した。以後、正孔阻止層としてBCPを60Åの厚さに蒸着し、その上に電子輸送層としてAlq3を200Åの厚さに蒸着した。最後に、電子輸送層上にリチウムフルオライド(lithium fluoride:LiF)を10Åの厚さに蒸着して電子注入層を形成した後、電子注入層上にアルミニウム(Al)陰極を1,200Åの厚さに蒸着して陰極を形成することにより、有機電界発光素子を製造した。
前記のように製造された有機発光素子に対して、マックサイエンス社のM7000で電界発光(EL)特性を測定し、その測定結果をもって、マックサイエンス社製の寿命測定装置(M6000)により、基準輝度が6,000cd/m2の時の、T90を測定した。前記T90は、初期輝度対比90%になる時間の寿命(単位:h、時間)を意味する。
前記実験例1から、正孔輸送層の形成時に本出願に係る化合物を用いた実施例1~46の有機発光素子の場合、正孔輸送層の形成時に本出願に係る化合物を用いなかった比較例1~4の有機発光素子より発光効率および寿命に優れていることを確認することができた。
(1)有機発光素子の製造
有機発光素子用ガラス(サムスン・コーニング社製)から得られた透明電極ITO薄膜を、トリクロロエチレン、アセトン、エタノール、蒸留水を順次に用いて各5分間超音波洗浄を実施した後、イソプロパノールに入れて保管した後に使用した。次に、真空蒸着装置の基板フォルダにITO基板を設け、真空蒸着装置内のセルに、下記の4,4’,4”-トリス(N,N-(2-ナフチル)-フェニルアミノ)トリフェニルアミン(4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine:2-TNATA)を入れた。
次いで、チャンバ内の真空度が10-6torrに到達するまで排気させた後、セルに電流を印加して2-TNATAを蒸発させて、ITO基板上に600Åの厚さの正孔注入層を蒸着した。真空蒸着装置内の他のセルに、下記のN,N’-ビス(α-ナフチル)-N,N’-ジフェニル-4,4’-ジアミン(N,N’-bis(α-naphthyl)-N,N’-diphenyl-4,4’-diamine:NPB)を入れて、セルに電流を印加して蒸発させて、正孔注入層上に300Åの厚さの正孔輸送層を蒸着した。
このように正孔注入層および正孔輸送層を形成させた後、その上に発光層として次の構造の青色発光材料を蒸着させた。具体的には、真空蒸着装置内の一方のセルに青色発光ホスト材料であるH1を200Åの厚さに真空蒸着させ、その上に青色発光ドーパント材料であるD1をホスト材料の重量対比5%真空蒸着させた。
電子注入層としてリチウムフルオライド(lithium fluoride:LiF)を10Åの厚さに蒸着し、Al陰極を1,000Åの厚さにして有機発光素子を製造した。一方、有機発光素子の製造に必要なすべての有機化合物は、材料ごとに、それぞれ10-6~10-8torr下で真空昇華精製して有機発光素子の製造に使用した。
前記のように製造された有機発光素子に対して、マックサイエンス社のM7000で電界発光(EL)特性を測定し、その測定結果をもって、マックサイエンス社製の寿命測定装置(M6000)により、基準輝度が6,000cd/m2の時の、T95を測定した。前記T95は、初期輝度対比95%になる時間の寿命(単位:h、時間)を意味する。
前記実験例2から、正孔補助層の形成時に本出願に係る化合物を用いた実施例47~92の有機発光素子の場合、正孔補助層の形成時に本出願に係る化合物を用いなかった比較例5~7の有機発光素子より発光効率および寿命に優れていることを確認することができた。
1)有機発光素子の作製
1,500Åの厚さにインジウムチンオキシド(ITO)が薄膜コーティングされたガラス基板を、蒸留水超音波洗浄した。蒸留水洗浄が終わると、アセトン、メタノール、イソプロピルアルコールなどの溶剤で超音波洗浄をし乾燥させた後、UV洗浄機でUVを用いて5分間UVO処理した。以後、基板をプラズマ洗浄機(PT)に搬送させた後、真空状態でITOの仕事関数および残膜除去のためにプラズマ処理をして、有機蒸着用熱蒸着装置に搬送した。
最後に、電子輸送層上にリチウムフルオライド(lithium fluoride:LiF)を10Åの厚さに蒸着して電子注入層を形成した後、電子注入層上にアルミニウム(Al)陰極を1,200Åの厚さに蒸着して陰極を形成することにより、有機発光素子を製造した。
前記のように作製された有機発光素子に対して、マックサイエンス社のM7000で電界発光(EL)特性を測定し、その測定結果をもって、マックサイエンス社製の寿命測定装置(M6000)により、基準輝度が6,000cd/m2の時の、T95を測定した。本発明により製造された有機発光素子の駆動電圧、発光効率、発光色、寿命を測定した結果は、下記表7の通りであった。
前記実験例3から、本出願に係る化合物を単一ホスト物質として用いて発光層を形成した実施例93~102の有機発光素子の場合、単一ホスト物質として用いて発光層を形成する時に単一ホスト物質として本出願に係る化合物を用いなかった比較例8、10および12の有機発光素子より発光効率および寿命に優れていることを確認することができた。
200:陽極
300:有機物層
301:正孔注入層
302:正孔輸送層
303:発光層
304:正孔阻止層
305:電子輸送層
306:電子注入層
400:陰極
Claims (12)
- 下記化学式1で表されるヘテロ環化合物:
前記化学式1において、
L1~L4は、互いに同一または異なり、それぞれ独立して、直接結合;置換もしくは非置換の炭素数6~60のアリーレン基;または置換もしくは非置換の炭素数2~60のヘテロアリーレン基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換の炭素数6~40のアリール基;または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
R1およびR2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換の炭素数1~20のアルキル基;置換もしくは非置換の炭素数6~40のアリール基;または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
X1~X3は、互いに同一または異なり、それぞれ独立して、水素;重水素;置換もしくは非置換の炭素数6~20のアリール基、または置換もしくは非置換の炭素数2~40のヘテロアリール基であり、
k、l、mおよびnは、それぞれ独立して、1~3の整数であり、
aは、1~6の整数であり、
bは、1~3の整数であり、
cは、1~4の整数であり、
k、l、m、n、a、bおよびcが2以上の場合、括弧内の置換基は、互いに同一または異なる。 - 前記「置換もしくは非置換」とは、炭素数1~60の直鎖もしくは分枝鎖のアルキル基;炭素数2~60の直鎖もしくは分枝鎖のアルケニル基;炭素数2~60の直鎖もしくは分枝鎖のアルキニル基;炭素数3~60の単環もしくは多環のシクロアルキル基;炭素数2~C60の単環もしくは多環のヘテロシクロアルキル基;炭素数6~60の単環もしくは多環のアリール基;炭素数2~60の単環もしくは多環のヘテロアリール基;シリル基;ホスフィンオキシド基;およびアミン基からなる群より選択された1以上の置換基で置換もしくは非置換であるか、前記例示された置換基の中から選択された2以上の置換基が連結された置換基で置換もしくは非置換であることを意味する、請求項1に記載のヘテロ環化合物。
- 第1電極と、第2電極と、前記第1電極と前記第2電極との間に備えられた1層以上の有機物層とを含む有機発光素子であって、前記有機物層のうちの1層以上は、請求項1~6のいずれか1項に記載のヘテロ環化合物を含む有機発光素子。
- 前記有機物層は、正孔輸送層を含み、前記正孔輸送層は、前記ヘテロ環化合物を含む、請求項7に記載の有機発光素子。
- 前記有機物層は、1層以上の正孔補助層を含み、前記正孔補助層は、前記ヘテロ環化合物を含む、請求項7に記載の有機発光素子。
- 前記有機物層は、発光層を含み、前記発光層は、前記ヘテロ環化合物を発光材料のホスト物質として含む、請求項7に記載の有機発光素子。
- 前記発光層は、2つ以上のホスト物質を含むことができ、前記ホスト物質の少なくとも1つは、前記ヘテロ環化合物を発光材料のホスト物質として含む、請求項10に記載の有機発光素子。
- 前記有機発光素子は、陽極と、前記陽極上に備えられ、第1発光層を含む第1スタックと、前記第1スタック上に備えられる電荷生成層と、前記電荷生成層上に備えられ、第2発光層を含む第2スタックと、前記第2スタック上に備えられる陰極とを含む、請求項7に記載の有機発光素子。
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WO2021054714A1 (ko) | 2021-03-25 |
EP4032876A4 (en) | 2023-10-04 |
CN114080381A (zh) | 2022-02-22 |
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