WO2015190400A1 - ピリミジン誘導体および有機エレクトロルミネッセンス素子 - Google Patents
ピリミジン誘導体および有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2015190400A1 WO2015190400A1 PCT/JP2015/066251 JP2015066251W WO2015190400A1 WO 2015190400 A1 WO2015190400 A1 WO 2015190400A1 JP 2015066251 W JP2015066251 W JP 2015066251W WO 2015190400 A1 WO2015190400 A1 WO 2015190400A1
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- Prior art keywords
- group
- formula
- compound
- phenyl
- pyrimidine derivative
- Prior art date
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- 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 55
- 239000000463 material Substances 0.000 claims abstract description 67
- 239000012044 organic layer Substances 0.000 claims abstract description 14
- 239000000470 constituent Substances 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 132
- -1 azafluorenyl group Chemical group 0.000 claims description 94
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 230000000903 blocking effect Effects 0.000 claims description 42
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 38
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 36
- 238000002347 injection Methods 0.000 claims description 33
- 239000007924 injection Substances 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000004431 deuterium atom Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000005493 quinolyl group Chemical group 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 238000005401 electroluminescence Methods 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 372
- 238000005160 1H NMR spectroscopy Methods 0.000 description 69
- 239000000843 powder Substances 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 31
- 238000005259 measurement Methods 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- PBYJMSFYALCTAK-UHFFFAOYSA-N 2-chloro-4-(4-phenylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound ClC1=NC(=CC(=N1)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C=1C=NC=CC=1 PBYJMSFYALCTAK-UHFFFAOYSA-N 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 23
- 239000001257 hydrogen Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- HFXYUCJLQZCNPD-UHFFFAOYSA-N (3-naphthalen-1-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C3=CC=CC=C3C=CC=2)=C1 HFXYUCJLQZCNPD-UHFFFAOYSA-N 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 16
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 13
- 239000010408 film Substances 0.000 description 13
- 239000010409 thin film Substances 0.000 description 13
- 125000001624 naphthyl group Chemical group 0.000 description 12
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 11
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 11
- 125000001725 pyrenyl group Chemical group 0.000 description 11
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 11
- 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 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 10
- 125000002541 furyl group Chemical group 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 125000001544 thienyl group Chemical group 0.000 description 10
- WGUQVZDSHMCHKO-UHFFFAOYSA-N N1=CC(=CC=C1)C1=CC=C(C=C1)C1=NC=CC=N1 Chemical compound N1=CC(=CC=C1)C1=CC=C(C=C1)C1=NC=CC=N1 WGUQVZDSHMCHKO-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 8
- OMFPHPKRNHPLKZ-UHFFFAOYSA-N 2,4-bis(4-naphthalen-1-ylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1(=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C=1C=NC=CC=1 OMFPHPKRNHPLKZ-UHFFFAOYSA-N 0.000 description 8
- WBCQECXDNKKDNT-UHFFFAOYSA-N 2-(4-naphthalen-1-ylphenyl)-4-(3-phenanthren-9-ylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1(=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC(=CC=C1)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1)C1=CC=C(C=C1)C=1C=NC=CC=1 WBCQECXDNKKDNT-UHFFFAOYSA-N 0.000 description 8
- YSVQBZQKOHFGHL-UHFFFAOYSA-N 3-[4-[2-(4-naphthalen-1-ylphenyl)-6-(4-phenylphenyl)pyrimidin-4-yl]phenyl]quinoline Chemical compound C1(=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C=1C=NC2=CC=CC=C2C=1 YSVQBZQKOHFGHL-UHFFFAOYSA-N 0.000 description 8
- NJHNDPAQQNKZMH-UHFFFAOYSA-N 4-(3-naphthalen-1-ylphenyl)-2-(4-phenanthren-9-ylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1=CC=CC=2C3=CC=CC=C3C(=CC1=2)C1=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC(=CC=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C=1C=NC=CC=1 NJHNDPAQQNKZMH-UHFFFAOYSA-N 0.000 description 8
- IDSGDUMRGPAEPN-UHFFFAOYSA-N 4-(3-naphthalen-2-ylphenyl)-2-(3-phenanthren-9-ylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1=CC=CC=2C3=CC=CC=C3C(=CC1=2)C=1C=C(C=CC=1)C1=NC(=CC(=N1)C1=CC(=CC=C1)C1=CC2=CC=CC=C2C=C1)C1=CC=C(C=C1)C=1C=NC=CC=1 IDSGDUMRGPAEPN-UHFFFAOYSA-N 0.000 description 8
- JFNSEQZCFNYWFY-UHFFFAOYSA-N 4-(4-naphthalen-1-ylphenyl)-2-(4-naphthalen-2-ylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1=C(C=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C=1C=NC=CC=1 JFNSEQZCFNYWFY-UHFFFAOYSA-N 0.000 description 8
- WPDGCQGCYZPRPS-UHFFFAOYSA-N 4-(4-naphthalen-1-ylphenyl)-2-(4-phenylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C=1C=NC=CC=1)C1=CC=CC=C1 WPDGCQGCYZPRPS-UHFFFAOYSA-N 0.000 description 8
- LCLQCYOWBGCARM-UHFFFAOYSA-N 4-(4-phenanthren-9-ylphenyl)-2-(3-phenylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1(=CC(=CC=C1)C1=NC(=CC(=N1)C1=CC=C(C=C1)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1)C1=CC=C(C=C1)C=1C=NC=CC=1)C1=CC=CC=C1 LCLQCYOWBGCARM-UHFFFAOYSA-N 0.000 description 8
- XUGKTBJJBNFJPU-UHFFFAOYSA-N 4-(4-phenanthren-9-ylphenyl)-2-(4-phenylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC=C(C=C1)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1)C1=CC=C(C=C1)C=1C=NC=CC=1)C1=CC=CC=C1 XUGKTBJJBNFJPU-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 8
- 239000002356 single layer Substances 0.000 description 8
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 7
- IJMVAKGIQNBCES-UHFFFAOYSA-N 2-(3-naphthalen-2-ylphenyl)-4-(3-phenylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1(=CC(=CC=C1)C1=NC(=NC(=C1)C1=CC=C(C=C1)C=1C=NC=CC=1)C1=CC(=CC=C1)C1=CC2=CC=CC=C2C=C1)C1=CC=CC=C1 IJMVAKGIQNBCES-UHFFFAOYSA-N 0.000 description 7
- BITUKAGQLFZPLL-UHFFFAOYSA-N 2-(3-naphthalen-2-ylphenyl)-4-(4-phenanthren-9-ylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1=C(C=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1=NC(=CC(=N1)C1=CC=C(C=C1)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1)C1=CC=C(C=C1)C=1C=NC=CC=1 BITUKAGQLFZPLL-UHFFFAOYSA-N 0.000 description 7
- GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 description 7
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 7
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 7
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XMVVTVOFHBWWCO-UHFFFAOYSA-N N1=CC(=CC=C1)C1=CC=C(C=C1)C1=CC=NC=N1 Chemical compound N1=CC(=CC=C1)C1=CC=C(C=C1)C1=CC=NC=N1 XMVVTVOFHBWWCO-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 125000004623 carbolinyl group Chemical group 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- 125000004306 triazinyl group Chemical group 0.000 description 5
- 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 4
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- 125000003342 alkenyl group Chemical group 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
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 150000004322 quinolinols Chemical class 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- WDDLHUWVLROJLA-UHFFFAOYSA-N 9,9'-spirobi[fluorene]-2-ylboronic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(B(O)O)C=C12 WDDLHUWVLROJLA-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003609 aryl vinyl group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- WLKQDOGZCIYEOM-UHFFFAOYSA-N (3-naphthalen-2-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=C3C=CC=CC3=CC=2)=C1 WLKQDOGZCIYEOM-UHFFFAOYSA-N 0.000 description 2
- NGZGJCQVEUFTHA-UHFFFAOYSA-N (3-phenanthren-9-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C3=CC=CC=C3C3=CC=CC=C3C=2)=C1 NGZGJCQVEUFTHA-UHFFFAOYSA-N 0.000 description 2
- BRMXCUCHGKWTIO-UHFFFAOYSA-N (4-phenanthren-9-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC2=CC=CC=C2C2=CC=CC=C12 BRMXCUCHGKWTIO-UHFFFAOYSA-N 0.000 description 2
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- MLTDJZYTQQUPPO-UHFFFAOYSA-N 2-(3-naphthalen-1-ylphenyl)-4-(4-phenanthren-9-ylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1(=CC=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1=NC(=CC(=N1)C1=CC=C(C=C1)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1)C1=CC=C(C=C1)C=1C=NC=CC=1 MLTDJZYTQQUPPO-UHFFFAOYSA-N 0.000 description 2
- GFGFAQPSTODNLI-UHFFFAOYSA-N 2-(3-naphthalen-1-ylphenyl)-4-(4-phenylphenyl)-6-(4-pyridin-3-ylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=C1)C1=CC=C(C=C1)C=1C=NC=CC=1)C1=CC(=CC=C1)C1=CC=CC2=CC=CC=C12)C1=CC=CC=C1 GFGFAQPSTODNLI-UHFFFAOYSA-N 0.000 description 2
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IHCHOVVAJBADAH-UHFFFAOYSA-N n-[2-hydroxy-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1C2=CC(OC)=CC=C2OCC1C(=O)NC(C(=C1)O)=CC=C1C=1C=NNC=1 IHCHOVVAJBADAH-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- VMFMUJZRXZXYAH-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl]prop-2-enamide Chemical compound C=CC(=O)NC=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)N(C)C)C(Cl)=CN=2)C(OC)=CC=1N1CCN(C)CC1 VMFMUJZRXZXYAH-UHFFFAOYSA-N 0.000 description 1
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- XEXYATIPBLUGSF-UHFFFAOYSA-N phenanthro[9,10-b]pyridine-2,3,4,5,6,7-hexacarbonitrile Chemical group N1=C(C#N)C(C#N)=C(C#N)C2=C(C(C#N)=C(C(C#N)=C3)C#N)C3=C(C=CC=C3)C3=C21 XEXYATIPBLUGSF-UHFFFAOYSA-N 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 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 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/00—Organic light-emitting devices
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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Definitions
- the present invention relates to a compound and an element suitable for an organic electroluminescence element, and more particularly to a pyrimidine derivative and an organic electroluminescence element using the derivative (hereinafter abbreviated as an organic EL element).
- the organic EL element is a self-luminous element, it is brighter and more visible than a liquid crystal element, and a clear display is possible. Therefore, active research has been done.
- an electroluminescent device in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on the substrate. Durability has been achieved.
- the light emitting layer can also be produced by doping a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence.
- a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence.
- the selection of the organic material in the organic EL element greatly affects various characteristics such as the efficiency and durability of the element.
- an organic EL element In an organic EL element, light injected from both electrodes is recombined in the light emitting layer to obtain light emission. However, it is important how efficiently both holes and electrons are transferred to the light emitting layer. High emission efficiency can be obtained by enhancing the electron injection property, increasing its mobility, improving the probability of recombination of holes and electrons, and confining excitons generated in the light emitting layer. it can. Therefore, the role played by the electron transport material is important, and there is a demand for an electron transport material that has high electron injectability, high electron mobility, high hole blocking properties, and high durability against holes. .
- the heat resistance and amorphousness of the material are also important.
- thermal decomposition occurs even at a low temperature due to heat generated when the element is driven, and the material deteriorates.
- the material to be used is required to have high heat resistance and good amorphous properties.
- a typical light emitting material tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq) is generally used as an electron transporting material. However, its hole blocking performance is insufficient.
- a hole blocking layer As a measure for preventing a part of holes from passing through the light emitting layer and improving the probability of charge recombination in the light emitting layer, there is a method of inserting a hole blocking layer.
- hole blocking materials triazole derivatives (see Patent Document 3), bathocuproine (hereinafter abbreviated as BCP), mixed ligand complexes of aluminum [aluminum (III) bis (2-methyl-8-quinolinate) ) -4-phenylphenolate (hereinafter abbreviated as BAlq)] and the like have been proposed.
- TAZ 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole
- TAZ has a large work function of 6.6 eV and high hole blocking ability, it is laminated on the cathode side of a fluorescent light emitting layer or phosphorescent light emitting layer produced by vacuum deposition or coating, and has an electron transporting hole blocking layer. It contributes to high efficiency of the organic EL element.
- TAZ has a low electron transport property
- BCP also has a high work function of 6.7 eV and a high hole blocking ability, but its glass transition point (Tg) is as low as 83 ° C., so that the stability of the thin film is poor.
- any material has an insufficient element lifetime or an insufficient function of blocking holes. Therefore, in order to improve the device characteristics of the organic EL device, an organic compound having excellent electron injection / transport performance and hole blocking capability and a long device lifetime is required.
- JP-A-8-48656 Japanese Patent No. 3194657 Japanese Patent No. 2734341 International Publication No. 2003/060956 International Publication No. 2014/009310
- An object of the present invention is to provide an organic compound having excellent electron injection / transport performance, hole blocking ability, and excellent characteristics as a material for a highly efficient and durable organic EL device. is there.
- Another object of the present invention is to provide an organic EL device having high efficiency, high durability and long life using this compound.
- the present inventors have paid attention to the fact that the nitrogen atom of the pyrimidine ring having electron affinity has the ability to coordinate to the metal, and is also excellent in heat resistance.
- a compound having a pyrimidine ring structure was designed and chemically synthesized.
- various organic EL devices were prototyped using the compound, and the characteristics of the devices were earnestly evaluated. As a result, the present invention has been completed.
- a pyrimidine derivative represented by the following general formula (1) is provided.
- Ar 1 represents an aromatic hydrocarbon group, a condensed polycyclic aromatic group or an aromatic heterocyclic group
- Ar 2 and Ar 3 may be the same or different and each represents a hydrogen atom, an aromatic hydrocarbon group, a condensed polycyclic aromatic group or an aromatic heterocyclic group, Ar 2 and Ar 3 are not simultaneously hydrogen atoms
- A represents a monovalent group represented by the following structural formula (2).
- R 1 to R 4 may be the same or different, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, or an aromatic hydrocarbon group.
- R 1 to R 4 and Ar 4 may be bonded to each other via a single bond, a methylene group, an oxygen atom or a sulfur atom to form a ring.
- a pyrimidine derivative represented by the following general formula (1-1) Where Ar 1 to Ar 3 and A have the same meanings as described in the general formula (1). 2) It is a pyrimidine derivative represented by the following general formula (1-2), Where Ar 1 to Ar 3 and A have the same meanings as described in the general formula (1). 3) A is a monovalent group represented by the following structural formula (2-1), Where Ar 4 and R 1 to R 4 have the same meanings as described in the structural formula (2). 4) A is a monovalent group represented by the following structural formula (2-2), Where Ar 4 and R 1 to R 4 have the same meanings as described in the structural formula (2).
- Ar 1 represents an aromatic hydrocarbon group or a condensed polycyclic aromatic group
- Ar 2 and Ar 3 may be the same or different, and represent a hydrogen atom, an aromatic hydrocarbon group or a condensed polycyclic aromatic group.
- Ar 4 is a pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, indolyl group, azafluorenyl group, diazafluorenyl group, quinoxalinyl group, benzoimidazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, azaspiro Be a bifluorenyl group or a diazaspirobifluorenyl group, 7)
- Ar 2 is a phenyl group having a substituent, 8)
- Ar 2 is a phenyl group having a substituent, and the substituent is an aromatic hydrocarbon group or a condensed polycyclic aromatic
- the pyrimidine derivative is used as a constituent material of at least one organic layer.
- An organic EL element is provided.
- the organic layer in which the pyrimidine derivative is used is preferably an electron transport layer, a hole blocking layer, a light emitting layer, or an electron injection layer.
- the pyrimidine derivative of the present invention is a novel compound and has the following characteristics. (1) Electron injection characteristics are good. (2) Electron moving speed is fast. (3) Excellent hole blocking ability. (4) The thin film state is stable. (5) Excellent heat resistance.
- the organic EL device of the present invention has the following characteristics. (6) High luminous efficiency. (7) The light emission start voltage is low. (8) The practical drive voltage is low. (9) Long life.
- the pyrimidine derivative of the present invention has a high electron injection / movement speed. Therefore, in an organic EL device having an electron injection layer and / or an electron transport layer manufactured using the pyrimidine derivative of the present invention, the electron transport efficiency from the electron transport layer to the light emitting layer is improved, and the light emission efficiency is improved. In addition, the driving voltage is low, and the durability of the organic EL element is improved.
- the pyrimidine derivative of the present invention is excellent in electron transportability as well as excellent hole blocking ability and stable in a thin film state. Therefore, the organic EL device having a hole blocking layer produced using the pyrimidine induction of the present invention has high emission efficiency, low driving voltage, improved current resistance, and maximum emission luminance. .
- the pyrimidine derivative of the present invention has an excellent electron transport property and a wide band gap. Therefore, by using the pyrimidine derivative of the present invention as the host material of the light-emitting layer and forming the light-emitting layer by supporting a fluorescent light-emitting material called a dopant, a phosphorescent light-emitting material, or a delayed fluorescent light-emitting material, driving voltage is low and light emission efficiency An organic EL element with improved can be realized.
- the pyrimidine derivative of the present invention is useful as a constituent material for an electron injection layer, an electron transport layer, a hole blocking layer, or a light emitting layer of an organic EL device.
- excitons generated in the light emitting layer can be confined, and further, the probability of recombination of holes and electrons can be improved and high luminous efficiency can be obtained.
- the driving voltage is low and high durability can be realized.
- FIG. 1 is a 1 H-NMR chart of the compound of Example 1 (Compound 74).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 2 (Compound 84).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 3 (Compound 89).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 4 (Compound 130).
- FIG. FIG. 3 is a 1 H-NMR chart of the compound of Example 5 (Compound 131).
- 2 is a 1 H-NMR chart of the compound of Example 6 (Compound 92).
- FIG. FIG. 2 is a 1 H-NMR chart of the compound of Example 7 (Compound 136).
- 2 is a 1 H-NMR chart of the compound of Example 8 (Compound 125).
- FIG. 3 is a 1 H-NMR chart of the compound of Example 9 (Compound 138).
- 2 is a 1 H-NMR chart of the compound of Example 10 (Compound 78).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 11 (Compound 76).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 12 (Compound 126).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 13 (Compound 124).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 14 (Compound 123).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 15 (Compound 146).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 16 (Compound 98).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 17 (Compound 153).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 18 (Compound 155).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 19 (Compound 82).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 20 (Compound 182).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 21 (Compound 227).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 22 (Compound 234).
- FIG. 2 is a 1 H-NMR chart of the compound of Example 23 (Compound 235).
- FIG. FIG. 2 is a diagram showing the EL element configurations of organic EL element examples 1 to 20 and organic EL element comparative example 1.
- the pyrimidine derivative of the present invention is a novel compound having a pyrimidine ring structure, and is represented by the following general formula (1).
- the pyrimidine derivative of the present invention has a structure represented by the following general formula (1-1) or (1-2).
- Ar 1 represents an aromatic hydrocarbon group, a condensed polycyclic aromatic group or an aromatic heterocyclic group
- Ar 2 and Ar 3 may be the same or different and each represents a hydrogen atom, an aromatic hydrocarbon group, a condensed polycyclic aromatic group or an aromatic heterocyclic group.
- Ar 2 and Ar 3 are not hydrogen atoms at the same time.
- A represents a monovalent group represented by Structural Formula (2) described later.
- Ar 1 to Ar 3 Specific examples of the aromatic hydrocarbon group or condensed polycyclic aromatic group represented by Ar 1 to Ar 3 include a phenyl group, a biphenylyl group, a terphenylyl group, a tetrakisphenyl group, a styryl group, a naphthyl group, an anthracenyl group, Examples include acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, and spirobifluorenyl group.
- aromatic heterocyclic group represented by Ar 1 to Ar 3 include an oxygen-containing aromatic hydrocarbon group such as a furyl group, a benzofuranyl group, a dibenzofuranyl group; a sulfur-containing aromatic heterocyclic group, For example, a thienyl group, a benzothienyl group, a dibenzothienyl group;
- the aromatic hydrocarbon group, condensed polycyclic aromatic group or aromatic heterocyclic group represented by Ar 1 to Ar 3 may be unsubstituted or may have a substituent.
- substituents include the following. Deuterium atom; A cyano group; A nitro group; Halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, iodine atoms; Alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert- Butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; An alkyloxy group having 1 to 6 carbon atoms, such as a methyloxy group, an ethyloxy group, a propyloxy group; An alkenyl group, such as a vinyl group, an ally
- substituents may be further substituted with the substituents exemplified above. These substituents may be present independently of each other, but may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. .
- Ar 1 , Ar 2 or Ar 3 to which the substituent and the substituent are bonded may be bonded to each other via an oxygen atom or a sulfur atom to form a ring, but exist independently. Thus, the ring may not be formed.
- A represents a monovalent group represented by the following structural formula (2).
- Ar 4 represents an aromatic heterocyclic group
- R 1 to R 4 may be the same or different, and are a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, or an aromatic hydrocarbon group.
- R 1 to R 4 and Ar 4 may exist independently of each other, They may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- Ar 4 Specific examples of the aromatic heterocyclic group represented by Ar 4 include triazinyl group, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group.
- the aromatic heterocyclic group represented by Ar 4 may be unsubstituted or may have a substituent.
- substituents include the same substituents as those which the aromatic hydrocarbon group, condensed polycyclic aromatic group or aromatic heterocyclic group represented by Ar 1 to Ar 3 may have. Can do. The aspect which a substituent can take is also the same.
- R 1 to R 4 Specific examples of the alkyl group having 1 to 6 carbon atoms represented by R 1 to R 4 include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, and 2-methylpropyl. Group, t-butyl group, n-pentyl group, 3-methylbutyl group, tert-pentyl group, n-hexyl group, iso-hexyl group, tert-hexyl group and the like.
- the alkyl group having 1 to 6 carbon atoms may be linear or branched.
- the alkyl group having 1 to 6 carbon atoms represented by R 1 to R 4 may be unsubstituted or may have a substituent.
- substituents include the following. Deuterium atom; A cyano group; A nitro group; A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc .; An alkyloxy group having 1 to 6 carbon atoms, such as a methyloxy group, an ethyloxy group, a propyloxy group; An alkenyl group, such as a vinyl group, an allyl group; An aryloxy group such as a phenyloxy group, a tolyloxy group and the like; Arylalkyloxy groups such as benzyloxy group, phenethyloxy group, etc .; Aromatic hydrocarbon group or condensed polycyclic aromatic group such as phenyl group, biphenylyl group, terphen
- substituents may be further substituted with the substituents exemplified above.
- the substituents may be present independently of each other, but may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- aromatic hydrocarbon group or condensed polycyclic aromatic group represented by R 1 to R 4 include a phenyl group, a biphenylyl group, a terphenylyl group, a tetrakisphenyl group, a styryl group, a naphthyl group, an anthracenyl group, Examples include acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, and spirobifluorenyl group.
- aromatic heterocyclic group represented by R 1 to R 4 include triazinyl group, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group.
- indolyl group carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, azafluorenyl group, diazafluorenyl group, naphthyridinyl group, phenanthate
- examples include a rolinyl group, an acridinyl group, a carbolinyl group, an azaspirobifluorenyl group, a diazaspirobifluorenyl group, and the like.
- the aromatic hydrocarbon group, condensed polycyclic aromatic group or aromatic heterocyclic group represented by R 1 to R 4 may be unsubstituted or may have a substituent.
- substituents include the same substituents as those which the aromatic hydrocarbon group, condensed polycyclic aromatic group or aromatic heterocyclic group represented by Ar 1 to Ar 3 may have. Can do. The aspect which a substituent can take is also the same.
- Suitable Ar 1 may include an aromatic hydrocarbon group or a condensed polycyclic aromatic group. Both the aromatic hydrocarbon group and the condensed polycyclic aromatic group may be unsubstituted or may have a substituent.
- suitable Ar 1 may include a phenyl group, a condensed polycyclic aromatic group, or an oxygen-containing or sulfur-containing aromatic heterocyclic group.
- a benzofuranyl group, a dibenzofuranyl group, a thienyl group, a benzothienyl group, and a dibenzothienyl group are preferable.
- Particularly preferred Ar 1 includes a phenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a spirobifluorenyl group, a dibenzofuranyl group, and a dibenzothienyl group. It can.
- a suitable or particularly preferred Ar 1 fused polycyclic aromatic group and oxygen-containing or sulfur-containing aromatic heterocyclic group may be unsubstituted or may have a substituent.
- the phenyl group which is the preferable or particularly preferable Ar 1 may be unsubstituted, but preferably has a substituent.
- a phenyl group, a biphenyl group, and a condensed polycyclic aromatic group are preferable.
- a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, and a spirobifluorenyl group are preferable as the substituent that the phenyl group has.
- the condensed polycyclic aromatic group that is a substituent of the phenyl group may further have a substituent or may be unsubstituted.
- the phenyl group and the substituent may be bonded to each other via an oxygen atom or a sulfur atom to form a ring, but they may be independently present to form no ring.
- Suitable Ar 2 includes a hydrogen atom, an aromatic hydrocarbon group, or a condensed polycyclic aromatic group. Both the aromatic hydrocarbon group and the condensed polycyclic aromatic group may be unsubstituted or may have a substituent.
- the spirobifluorenyl group and the oxygen-containing or sulfur-containing aromatic heterocyclic group may have a substituent or may be unsubstituted.
- the phenyl group preferably has a substituent.
- the substituent that the phenyl group has is preferably an aromatic hydrocarbon group, a condensed polycyclic aromatic group, or an oxygen-containing or sulfur-containing aromatic heterocyclic group.
- aromatic hydrocarbon groups such as phenyl group, biphenylyl group, terphenyl group; naphthyl group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group
- Condensed polycyclic aromatic groups such as spirobifluorenyl group; oxygen-containing aromatic heterocyclic groups such as furyl group, benzofuranyl group and dibenzofuranyl group; sulfur-containing groups such as thienyl group, benzothienyl group and dibenzothienyl group
- An aromatic heterocyclic group is preferable; a phenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group
- a suitable substituent that the above-mentioned phenyl group has may further have a substituent, but may be unsubstituted. Moreover, the phenyl group and the substituent may be bonded to each other via an oxygen atom or a sulfur atom to form a ring, but they may be independently present to form no ring.
- Ar 2 may have a substituent other than an aromatic heterocyclic group, that is, a deuterium atom, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, or the number of carbon atoms 1-6 alkyloxy groups, alkenyl groups, aryloxy groups, arylalkyloxy groups, aromatic hydrocarbon groups or condensed polycyclic aromatic groups, arylvinyl groups or acyl groups are preferred.
- a substituent other than an aromatic heterocyclic group that is, a deuterium atom, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, or the number of carbon atoms 1-6 alkyloxy groups, alkenyl groups, aryloxy groups, arylalkyloxy groups, aromatic hydrocarbon groups or condensed polycyclic aromatic groups, arylvinyl groups or acyl groups are preferred
- Suitable Ar 3 includes a hydrogen atom, an aromatic hydrocarbon group, or a condensed polycyclic aromatic group. Both the aromatic hydrocarbon group and the condensed polycyclic aromatic group may be unsubstituted or may have a substituent.
- suitable Ar 3 may include a hydrogen atom, a phenyl group, a spirobifluorenyl group, or an oxygen-containing or sulfur-containing aromatic heterocyclic group.
- More preferable Ar 3 includes a hydrogen atom, a phenyl group, a spirobifluorenyl group, a furyl group, a benzofuranyl group, a dibenzofuranyl group, a thienyl group, a benzothienyl group, and a dibenzothienyl group.
- a suitable or more preferable Ar 3 spirobifluorenyl group, oxygen-containing or sulfur-containing aromatic heterocyclic group may have a substituent or may be unsubstituted.
- the phenyl group which is preferable or more preferable Ar 3 preferably has a substituent.
- the substituent that the phenyl group has is preferably an aromatic hydrocarbon group, a condensed polycyclic aromatic group, an oxygen-containing or sulfur-containing aromatic heterocyclic group.
- the substituents of the phenyl group include a phenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a spirobifluorenyl group, a dibenzofuranyl group, and a dibenzothienyl group.
- the substituent and the phenyl group may be bonded to each other via an oxygen atom or a sulfur atom to form a ring, but each independently exists to form a ring. You don't have to.
- Particularly suitable Ar 3 includes a hydrogen atom.
- Ar 3 may have a substituent other than an aromatic heterocyclic group, that is, a deuterium atom, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, or the number of carbon atoms 1-6 alkyloxy groups, alkenyl groups, aryloxy groups, arylalkyloxy groups, aromatic hydrocarbon groups or condensed polycyclic aromatic groups, arylvinyl groups or acyl groups are preferred.
- a substituent other than an aromatic heterocyclic group that is, a deuterium atom, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, or the number of carbon atoms 1-6 alkyloxy groups, alkenyl groups, aryloxy groups, arylalkyloxy groups, aromatic hydrocarbon groups or condensed polycyclic aromatic groups, arylvinyl groups or acyl groups are preferred
- Ar 1 and Ar 2 may be the same, but are preferably different from the viewpoint of the stability of the thin film.
- Ar 1 and Ar 2 may have different substituents, or may have the same substituent at different substitution positions.
- Ar 2 and Ar 3 may be the same group, but they may be easily crystallized when the symmetry of the whole molecule is increased. Therefore, they are preferably different groups from the viewpoint of the stability of the thin film.
- One of Ar 2 and Ar 3 is preferably a hydrogen atom, and Ar 3 is particularly preferably a hydrogen atom. As already mentioned, in the present invention, Ar 2 and Ar 3 are not simultaneously hydrogen atoms.
- the group A is preferably represented by the following structural formula (2-1), that is, the group Ar 4 is a benzene ring with respect to the pyrimidine ring represented by the general formula (1). And are preferably bonded at the meta position.
- the group A is preferably represented by the following structural formula (2-2) from the viewpoint of synthesis, that is, the group Ar 4 is a benzene ring with respect to the pyrimidine ring represented by the general formula (1). And are preferably bonded at the para position.
- Suitable Ar 4 includes nitrogen-containing heterocyclic groups such as triazinyl group, pyridyl group, pyrimidinyl group, pyrrolyl group, quinolyl group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, List benzoimidazolyl, pyrazolyl, azafluorenyl, diazafluorenyl, naphthyridinyl, phenanthrolinyl, acridinyl, carbolinyl, azaspirobifluorenyl, diazaspirobifluorenyl Can do.
- nitrogen-containing heterocyclic groups such as triazinyl group, pyridyl group, pyrimidinyl group, pyrrolyl group, quinolyl group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group,
- Ar 4 includes triazinyl group, pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, indolyl group, quinoxalinyl group, azafluorenyl group, diazafluorenyl group, benzoimidazolyl group, naphthyridinyl group, phenanthrolinyl group , An acridinyl group, an azaspirobifluorenyl group, and a diazaspirobifluorenyl group.
- the most preferred Ar 4 includes pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, indolyl group, azafluorenyl group, diazafluorenyl group, quinoxalinyl group, benzoimidazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group And azaspirobifluorenyl group and diazaspirobifluorenyl group.
- the pyridyl group is preferably a pyridin-3-yl group.
- R 1 to R 4 are preferably a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, trifluoromethyl group, alkyl group having 1 to 6 carbon atoms, aromatic hydrocarbon group or condensed polycyclic ring.
- An aromatic group can be exemplified, and more preferable R 1 to R 4 include a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, or an alkyl group having 1 to 6 carbon atoms.
- Particularly preferred examples of R 1 to R 4 include a hydrogen atom or a deuterium atom.
- the pyrimidine derivative of the present invention can be produced, for example, by the following method. That is, a Suzuki coupling reaction between 2,4,6-trichloropyrimidine and an arylboronic acid or arylboronic acid ester having a group corresponding to the 4-position is performed, and then the corresponding heteroaryl group is used as a substituent. Add phenylboronic acid or phenylboronic acid ester and perform Suzuki coupling reaction. By such a two-stage Suzuki coupling reaction, a corresponding group is introduced into the 4-position of the pyrimidine ring, and a phenyl group having a corresponding heteroaryl group as a substituent is introduced into the 6-position.
- the order of introducing the groups at the 2-position, 4-position, and 6-position of the pyrimidine ring may be appropriately changed. Furthermore, in the above production method, when a pyrimidine substituted with a halogen atom such as a chloro group, such as 2,4,5-trichloropyrimidine, is used instead of 2,4,6-trichloropyrimidine, the substitution position differs. Pyrimidine derivatives can be produced.
- the resulting compound can be purified by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization or crystallization using a solvent, sublimation purification, and the like.
- the compound can be identified by NMR analysis. As physical properties, work function and glass transition point (Tg) can be measured.
- the work function is an indicator of hole blocking properties.
- the work function can be measured using an ionization potential measuring apparatus (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) by forming a 100 nm thin film on the ITO substrate.
- PYS-202 manufactured by Sumitomo Heavy Industries, Ltd.
- the glass transition point (Tg) is an indicator of the stability of the thin film state.
- the glass transition point (Tg) can be measured, for example, with a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S) using powder.
- An organic EL element having at least one organic layer formed by using the above-described pyrimidine derivative of the present invention between a pair of electrodes (hereinafter sometimes referred to as the organic EL element of the present invention) is, for example, The layer structure shown in FIG. That is, in the organic EL device of the present invention, for example, the anode 2, the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, the hole blocking layer 6, the electron transport layer 7, and the electron injection are sequentially formed on the substrate. Layer 8 and cathode 9 are provided.
- the organic EL device of the present invention is not limited to such a structure.
- an electron blocking layer (not shown) may be provided between the hole transport layer 4 and the light emitting layer 5.
- the positive hole injection layer 3 between the anode 2 and the hole transport layer 4 and the positive layer between the light emitting layer 5 and the electron transport layer 7 may be omitted.
- the hole blocking layer 6, the electron injection layer 8 between the electron transport layer 7 and the cathode 9 are omitted, and the anode 2, the hole transport layer 4, the light emitting layer 5, the electron transport layer 7, and the cathode 9 are sequentially formed on the substrate 1. It can also be set as the structure which has.
- the anode 2 may be composed of a known electrode material, for example, an electrode material having a large work function such as ITO or gold.
- the hole injection layer 3 may be made of a material known per se having hole injection properties, and can be formed using, for example, the following materials. Porphyrin compounds represented by copper phthalocyanine; Starburst type triphenylamine derivatives; Triphenylamine trimer and tetramer, for example, an arylamine compound having a structure in which three or more triphenylamine structures are linked by a divalent group containing no single bond or heteroatom in the molecule; Acceptor heterocyclic compounds such as hexacyanoazatriphenylene; Coating type polymer material;
- the hole injection layer 3 (thin film) can be formed by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method. Similarly, various layers described below can be formed by known methods such as vapor deposition, spin coating, and ink jet.
- the hole transport layer 4 may be made of a material known per se having hole transport properties, and can be formed using, for example, the following materials.
- Benzidine derivatives such as N, N′-diphenyl-N, N′-di (m-tolyl) -benzidine (hereinafter abbreviated as TPD), N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) -benzidine (hereinafter abbreviated as NPD), N, N, N ′, N′-tetrabiphenylylbenzidine; 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC); Various triphenylamine trimers and tetramers;
- the above-described hole transport material may be used alone for film formation, but may be mixed with other materials to form a film, and the hole transport layer may be formed by mixing the layers formed alone. Alternatively
- a layer serving as the hole injection layer 3 and the hole transport layer 4 can also be formed.
- Such a hole injection / transport layer is coated with poly (3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT) / poly (styrene sulfonate) (hereinafter abbreviated as PSS).
- PEDOT poly (3,4-ethylenedioxythiophene)
- PSS poly (styrene sulfonate)
- a type of polymeric material can be used.
- the electron blocking layer (not shown) can be formed using a known compound having an electron blocking action.
- known electron blocking compounds include the following. Carbazole derivatives such as 4,4 ′, 4 ′′ -tri (N-carbazolyl) triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis [4- (carbazol-9-yl) phenyl] fluorene, 1,3-bis (carbazol-9-yl) benzene (hereinafter, mCP Abbreviated), 2,2-bis (4-carbazol-9-ylphenyl) adamantane (hereinafter abbreviated as Ad-Cz); A compound having a triphenylsilyl group and a triarylamine structure, for example, 9- [4- (carbazol-9-yl) phenyl] -9- [4- ( Triphenylsilyl) phenyl] -9H-fluorene;
- TCTA N-carbazoly
- the light-emitting layer 5 can be formed using a known material in addition to the pyrimidine derivative of the present invention.
- known materials include the following. Metal complexes of quinolinol derivatives including Alq 3 ; Various metal complexes; Anthracene derivatives; Bisstyrylbenzene derivatives; Pyrene derivatives; An oxazole derivative; Polyparaphenylene vinylene derivatives;
- the light emitting layer 5 may be composed of a host material and a dopant material.
- a host material in addition to the pyrimidine derivative of the present invention and the light emitting material, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or the like can be used.
- the dopant material quinacridone, coumarin, rubrene, perylene, and derivatives thereof; benzopyran derivatives; rhodamine derivatives; aminostyryl derivatives;
- the light emitting layer material may be used alone for film formation, but may be mixed with other materials to form a film, and the light emitting layer may be formed by mixing layers formed independently.
- a stacked structure may be used in which layers are formed separately or mixed with a layer formed alone.
- a phosphorescent emitter As the phosphorescent emitter, a phosphorescent emitter of a metal complex such as iridium or platinum can be used. In particular, Green phosphorescent emitters, such as Ir (ppy) 3 ; Blue phosphorescent emitters such as FIrpic, FIr6; A red phosphorescent emitter, such as Btp 2 Ir (acac); Etc. are used.
- Carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP), TCTA, mCP; Can be used.
- CBP 4,4′-di (N-carbazolyl) biphenyl
- TCTA 4,4′-di (N-carbazolyl) biphenyl
- mCP mCP
- UGH2 p-bis (triphenylsilyl) benzene
- TPBI 1,3,5-phenylene
- TPBI 1,3,5-phenylene
- the doping of the phosphorescent light-emitting material into the host material is preferably performed by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer in order to avoid concentration quenching.
- CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN, etc.
- the hole blocking layer 6 can be formed using a known compound having hole blocking properties in addition to the pyrimidine derivative of the present invention.
- known compounds having hole blocking properties include the following. Phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP); Metal complexes of quinolinol derivatives, such as BAlq; Various rare earth complexes; An oxazole derivative; Triazole derivatives; Triazine derivatives;
- BCP bathocuproine
- the hole blocking material may be used alone for film formation, it may be formed by mixing with other materials, and the hole blocking layer may be mixed with the layers formed independently.
- a stacked structure may be employed in which the formed layers or a layer formed by mixing with a single layer is stacked.
- the above-described known materials having hole blocking properties can also be used for forming the electron transport layer 7 described below. That is, a layer that is the hole blocking layer 6 and the electron transporting layer 7 can be formed by using a known material having the hole blocking property.
- the electron transport layer 7 is formed using a known compound having an electron transport property in addition to the pyrimidine derivative of the present invention.
- known compounds having an electron transporting property include the following. Metal complexes of quinolinol derivatives including Alq 3 and BAlq; Various metal complexes; Triazole derivatives; Triazine derivatives; Oxadiazole derivatives; Pyridine derivatives; Benzimidazole derivatives; Thiadiazole derivatives; Anthracene derivatives; Carbodiimide derivatives; Quinoxaline derivatives; Pyridoindole derivatives; Phenanthroline derivatives; Silole derivatives;
- the electron transport material may be used alone for film formation, but may be mixed with other materials for film formation, and the electron transport layer may be formed by mixing the layers formed independently with each other. Alternatively, a stacked structure may be used in which stacked layers or layers formed by mixing with a single layer are stacked.
- the electron injection layer 8 can be formed using a material known per se, such as the following. Alkali metal salts such as lithium fluoride and cesium fluoride; Alkaline earth metal salts such as magnesium fluoride; Metal complexes of quinolinol derivatives such as lithium quinolinol;
- the metal oxide electron injection layer 8 such as aluminum oxide can be omitted in the preferred selection of the electron transport layer and the cathode.
- a material further doped with a metal such as cesium can be used.
- an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
- Example 1 Synthesis of Compound 74 Synthesis of 4- (biphenyl-4-yl) -2- ⁇ 3- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 74) In a reaction vessel purged with nitrogen, 3- (naphthalen-1-yl) phenylboronic acid 5.0 g, 7.0 g of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine, 0.96 g of tetrakistriphenylphosphine, 6.9 g of potassium carbonate, 35 ml of toluene, 70 ml of 1,4-dioxane and 35 ml of water The mixture was heated and stirred at 85 ° C.
- Example 2 Synthesis of compound 84> 4- (biphenyl-3-yl) -2- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 84) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 4- (naphthalen-1-yl) phenylboronic acid was used, Instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine 2-chloro-4- (biphenyl-3-yl) -6- ⁇ 4 The reaction was performed using-(pyridin-3-yl) phenyl ⁇ pyrimidine under the same conditions.
- Example 3 Synthesis of Compound 89 4- (biphenyl-3-yl) -2- ⁇ 3- (naphthalen-2-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 89) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 3- (naphthalen-2-yl) phenylboronic acid was used, Instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine 2-chloro-4- (biphenyl-3-yl) -6- ⁇ 4 The reaction was performed using-(pyridin-3-yl) phenyl ⁇ pyrimidine under the same conditions.
- Example 4 Synthesis of compound 130> 2- ⁇ 3- (naphthalen-1-yl) phenyl ⁇ -4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine;
- the reaction was performed under the same conditions using 6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 5 Synthesis of Compound 131 2- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 131) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 4- (naphthalen-1-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine - The reaction was performed under the same conditions using 6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 6 Synthesis of Compound 92 2- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -4- ⁇ 3- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 92) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 4- (naphthalen-1-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 3- (naphthalen-1-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6- The reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 7 Synthesis of Compound 136 2- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ -4- ⁇ 3- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 136)
- 4- (phenanthrene-9-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 3- (naphthalen-1-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6-
- the reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 8 Synthesis of Compound 125 2- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 125) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 4- (naphthalen-1-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6- The reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 9 Synthesis of Compound 138 2- ⁇ 4- (naphthalen-2-yl) phenyl ⁇ -4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 138) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 4- (naphthalen-2-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6- The reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 10 Synthesis of Compound 78 2- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ -4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 78) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 4- (phenanthrene-9-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6- The reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 11 Synthesis of Compound 76 2- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -4- ⁇ 3- (naphthalen-2-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 76) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 4- (naphthalen-1-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 3- (naphthalen-2-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6- The reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 12 Synthesis of Compound 126 2- (biphenyl-4-yl) -4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 126)
- 4-biphenylboronic acid was used, 2-chloro-4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -
- the reaction was performed under the same conditions using 6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 13 Synthesis of Compound 124 2- (biphenyl-4-yl) -4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 124)
- 2-chloro-4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6-
- the reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 14 Synthesis of Compound 123 2- (biphenyl-3-yl) -4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 123)
- 3-biphenylboronic acid was used, 2-chloro-4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -
- the reaction was performed under the same conditions using 6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 15 Synthesis of Compound 146 2- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -4- (biphenyl-4-yl) -6- ⁇ 4- (quinolin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 146)
- Example 1 instead of 3- (naphthalen-1-yl) phenylboronic acid, 4- (naphthalen-1-yl) phenylboronic acid was used, Instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4 The reaction was carried out under the same conditions using-(quinolin-3-yl) phenyl ⁇ pyrimidine.
- Example 16 Synthesis of Compound 98 2- ⁇ 3- (phenanthren-9-yl) phenyl ⁇ -4- ⁇ 3- (naphthalen-2-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 98) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 3- (phenanthren-9-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 3- (naphthalen-2-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6- The reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 17 Synthesis of compound 153> 2- ⁇ 3- (naphthalen-2-yl) phenyl ⁇ -4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine;
- 3- (naphthalen-1-yl) phenylboronic acid 3- (naphthalen-2-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 4- (phenanthren-9-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -
- the reaction was performed under the same conditions using 6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 18 Synthesis of Compound 155 2- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -4- ⁇ 3- (phenanthren-9-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 155)
- 4- (naphthalen-1-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 3- (phenanthren-9-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -
- the reaction was performed under the same conditions using 6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 19 Synthesis of Compound 82 2- ⁇ 3- (phenanthren-9-yl) phenyl ⁇ -4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine; Formula (1-1) A: Formula (2-2) Ar 3 : H (Compound 82) In Example 1, Instead of 3- (naphthalen-1-yl) phenylboronic acid, 3- (phenanthren-9-yl) phenylboronic acid was used, 2-chloro-4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6- The reaction was performed under the same conditions using ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine.
- Example 20 Synthesis of compound 182> 2- ⁇ 3- (naphthalen-1-yl) phenyl ⁇ -4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 4- (quinolin-3-yl) phenyl ⁇ pyrimidine;
- the reaction was carried out under the same conditions using ⁇ 4- (quinolin-3-yl) phenyl ⁇ pyrimidine.
- Example 21 Synthesis of Compound 227 2- (9,9′-spirobi [9H-fluoren] -2-yl) -4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ -6- ⁇ 3- (pyridin-3-yl) phenyl ⁇ pyrimidine ; Formula (1-1) A: Formula (2-1) Ar 3 : H (Compound 227)
- 9,9′-spirobi [9H-fluorene] -2-boronic acid was used instead of 3- (naphthalen-1-yl) phenylboronic acid, 2-chloro-4- ⁇ 4- (naphthalen-1-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6-
- the reaction was carried out under the same conditions using ⁇ 3- (pyridin-3-yl) phenyl ⁇ pyrimidine
- Example 23 Synthesis of Compound 235 2- (9,9′-spirobi [9H-fluoren] -2-yl) -4- ⁇ 4- (naphthalen-2-yl) phenyl ⁇ -6- ⁇ 3- (pyridin-3-yl) phenyl ⁇ pyrimidine ; Formula (1-1) A: Formula (2-1) Ar 3 : H (Compound 235)
- 9,9′-spirobi [9H-fluorene] -2-boronic acid was used instead of 3- (naphthalen-1-yl) phenylboronic acid, 2-chloro-4- ⁇ 4- (naphthalen-2-yl) phenyl ⁇ instead of 2-chloro-4- (biphenyl-4-yl) -6- ⁇ 4- (pyridin-3-yl) phenyl ⁇ pyrimidine -6-
- the reaction was carried out under the same conditions using ⁇ 3- (pyridin-3-yl) phenyl ⁇ pyrim
- a deposited film having a thickness of 100 nm was formed on an ITO substrate, and the work function was measured with an ionization potential measuring device (PYS-202 type, manufactured by Sumitomo Heavy Industries, Ltd.).
- Compound of Example 23 (Compound 235) 146 ° C.
- the compound of the present invention has a glass transition point of 100 ° C. or higher, particularly 140 ° C. or higher. This indicates that the thin film state is stable in the compound of the present invention.
- the organic EL element has a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, and a hole blocking layer on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2.
- the layer 6, the electron transport layer 7, the electron injection layer 8, and the cathode (aluminum electrode) 9 were deposited in this order.
- the glass substrate 1 formed with ITO having a thickness of 150 nm was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 200 ° C. for 10 minutes. Then, after performing UV ozone treatment for 15 minutes, this glass substrate with ITO was attached in a vacuum evaporation machine, and pressure was reduced to 0.001 Pa or less. Subsequently, a compound HIM-1 having the following structural formula was formed to a thickness of 5 nm as a hole injection layer 3 so as to cover the transparent anode 2. On the hole injection layer 3, a compound HTM-1 having the following structural formula was formed as the hole transport layer 4 so as to have a film thickness of 65 nm.
- Binary vapor deposition was performed at a vapor deposition rate to form a film thickness of 20 nm.
- the compound of Example 1 (Compound 74) and the compound ETM-1 of the following structural formula as the hole blocking layer 6 and electron transport layer 7 were deposited.
- 74): binary deposition was performed at a deposition rate of ETM-1 50: 50 to form a film thickness of 30 nm.
- lithium fluoride was formed as the electron injection layer 8 to a thickness of 1 nm.
- aluminum was deposited to 100 nm to form the cathode 9.
- Example 1 of the organic EL device instead of the compound (Compound 74) of Example 1 as the material of the hole blocking layer 6 and the electron transport layer 7, Compound ETM-2 (patent) Other than that, an organic EL element was produced under the same conditions as in Example 1. (ETM-2)
- the element lifetimes of the organic EL elements produced in organic EL element examples 1 to 20 and organic EL element comparative example 1 were measured. Specifically, when constant current driving is performed with the light emission luminance (initial luminance) at the start of light emission being 2000 cd / m 2 , the light emission luminance is 1900 cd / m 2 (corresponding to 95% when the initial luminance is 100%). : 95% attenuation). The results are shown in Table 1.
- the luminous efficiency when a current having a current density of 10 mA / cm 2 was passed was 6.35 cd / A in the organic EL element comparative example 1, whereas the organic EL element examples 1 to 20 Then, it was greatly improved to 6.86 to 8.23 cd / A.
- the organic EL element comparative example 1 was 5.20 lm / W, while the organic EL element examples 1 to 20 were greatly improved to 5.76 to 6.98 lm / W.
- the life of the organic EL element examples 1 to 20 was significantly increased to 128 to 276 hours compared to 55 hours in the organic EL element comparative example 1.
- the long life can be realized in this way because the pyrimidine derivative of the present invention has a stable thin film state and superior heat resistance compared to conventional organic EL device materials. Further, it is presumed that the carrier balance of the pyrimidine derivative of the present invention is excellent. Further, regarding the drive voltage, the values of the organic EL element examples 1 to 20 were the same as or lower than those of the organic EL element comparative example 1.
- the organic EL device of the present invention is superior in luminous efficiency and power efficiency as compared with a device using the compound ETM-2 which is a general electron transport material, and realizes a long-life organic EL device. I understood that I can do it.
- the pyrimidine derivative of the present invention is excellent as a compound for an organic EL device because it has good electron injection characteristics, excellent hole blocking ability, and a stable thin film state.
- By producing an organic EL element using the compound high efficiency can be obtained, driving voltage can be lowered, and durability can be improved. For example, it has become possible to develop home appliances and lighting.
Abstract
Description
Ar1は、芳香族炭化水素基、縮合多環芳香族基または芳香族複素環
基を表し、
Ar2、Ar3は同一でも異なってもよく、水素原子、芳香族炭化水
素基、縮合多環芳香族基または芳香族複素環基を表し、
Ar2とAr3は同時に水素原子となることはなく、
Aは、下記構造式(2)で示される1価基を表す、
Ar4は、芳香族複素環基を表し、
R1~R4は、同一でも異なってもよく、水素原子、重水素原子
、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、炭素
原子数1~6のアルキル基、芳香族炭化水素基、縮合多環芳香族基
または芳香族複素環基を表し、
R1~R4とAr4は単結合、メチレン基、酸素原子または硫黄
原子を介して互いに結合して環を形成してもよい。
1)下記一般式(1-1)で表されるピリミジン誘導体であること、
Ar1~Ar3及びAは、前記一般式(1)に記載した通りの意味で
ある、
2)下記一般式(1-2)で表されるピリミジン誘導体であること、
Ar1~Ar3及びAは、前記一般式(1)に記載した通りの意味で
ある、
3)Aが下記構造式(2-1)で示される1価基であること、
Ar4およびR1~R4は、前記構造式(2)に記載した通りの意味
である、
4)Aが下記構造式(2-2)で示される1価基であること、
Ar4およびR1~R4は、前記構造式(2)に記載した通りの意味
である、
5)Ar1は、芳香族炭化水素基または縮合多環芳香族基を表し、Ar2、Ar3は同一でも異なってもよく、水素原子、芳香族炭化水素基または縮合多環芳香族基を表すこと、
6)Ar4がピリジル基、ピリミジニル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基またはジアザスピロビフルオレニル基であること、
7)Ar2が置換基を有するフェニル基であること、
8)Ar2が置換基を有するフェニル基であり、該置換基が、芳香族炭化水素基、または縮合多環芳香族基であること、
9)Ar2が置換基を有するフェニル基であり、該置換基が、芳香族炭化水素基であること、
10)Ar2が置換基を有するフェニル基であり、該置換基が、縮合多環芳香族基であること、
11)Ar3が水素原子であること、
12)Ar1が置換基を有するフェニル基であること、
13)Ar1が置換基を有するフェニル基であり、該置換基が、縮合多環芳香族基であること、
14)Ar1が縮合多環芳香族基であること、
15)Ar1が無置換のフェニル基であること、
が好ましい。
(1)電子の注入特性が良い。
(2)電子の移動速度が速い。
(3)正孔阻止能力に優れる。
(4)薄膜状態が安定である。
(5)耐熱性に優れている。
(6)発光効率が高い。
(7)発光開始電圧が低い。
(8)実用駆動電圧が低い。
(9)長寿命である。
Ar1は、芳香族炭化水素基、縮合多環芳香族基または芳香族複素環基
を表し、
Ar2、Ar3は同一でも異なってもよく、水素原子、芳香族炭化水素
基、縮合多環芳香族基または芳香族複素環基を表す。
Ar2とAr3は同時に水素原子となることはない。
Aは、後述の構造式(2)で示される1価基を表す。
Ar1~Ar3で表される芳香族炭化水素基または縮合多環芳香族基としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、テトラキスフェニル基、スチリル基、ナフチル基、アントラセニル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、スピロビフルオレニル基等を挙げることができる。
Ar1~Ar3で表される芳香族複素環基としては、具体的には、含酸素芳香族炭化水素基、例えばフリル基、ベンゾフラニル基、ジベンゾフラニル基;含硫黄芳香族複素環基、例えばチエニル基、ベンゾチエニル基、ジベンゾチエニル基;などを挙げることができる。
重水素原子;
シアノ基;
ニトロ基;
ハロゲン原子、例えばフッ素原子、塩素原子、臭素原子、ヨウ素原子
;
炭素原子数1~6のアルキル基、例えばメチル基、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、tert-
ブチル基、n-ペンチル基、イソペンチル基、ネオペンチル基、n-ヘ
キシル基;
炭素原子数1~6のアルキルオキシ基、例えばメチルオキシ基、エチ
ルオキシ基、プロピルオキシ基;
アルケニル基、例えばビニル基、アリル基;
アリールオキシ基、例えばフェニルオキシ基、トリルオキシ基;
アリールアルキルオキシ基、例えばベンジルオキシ基、フェネチルオ
キシ基;
芳香族炭化水素基または縮合多環芳香族基、例えばフェニル基、ビフ
ェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェ
ナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレ
ニル基、フルオランテニル基、トリフェニレニル基、スピロビフルオレ
ニル基;
芳香族複素環基、例えばピリジル基、チエニル基、フリル基、ピロリ
ル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニ
ル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾ
チアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル
基、ジベンゾフラニル基、ジベンゾチエニル基、アザフルオレニル基、
ジアザフルオレニル基、カルボリニル基、アザスピロビフルオレニル基
、ジアザスピロビフルオレニル基;
アリールビニル基、例えばスチリル基、ナフチルビニル基;
アシル基、例えばアセチル基、ベンゾイル基;
炭素原子数1~6のアルキル基および炭素原子数1~6のアルキルオキシ基は直鎖状であっても分岐状であってもよい。これらの置換基は、さらに前記例示した置換基で置換されていても良い。これらの置換基同士は、互いに独立して存在していてもよいが、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。また、置換基と当該置換基が結合しているAr1、Ar2またはAr3は、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよいが、それぞれ独立して存在して環を形成していなくてもよい。
Aは、下記構造式(2)で示される1価基を表す。
Ar4は、芳香族複素環基を表し、
R1~R4は、同一でも異なってもよく、水素原子、重水素原子
、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、炭素
原子数1~6のアルキル基、芳香族炭化水素基、縮合多環芳香族基
または芳香族複素環基を表す。
R1~R4とAr4は、互いに独立して存在していてもよいが、
単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原
子を介して互いに結合して環を形成していてもよい。
Ar4で表される芳香族複素環基としては、具体的に、トリアジニル基、ピリジル基、ピリミジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、アザフルオレニル基、ジアザフルオレニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、カルボリニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基等を挙げることができる。
R1~R4で表される炭素原子数1~6のアルキル基としては、具体的に、メチル基、エチル基、n-プロピル基、i-プロピル基、n-ブチル基、2-メチルプロピル基、t-ブチル基、n-ペンチル基、3-メチルブチル基、tert-ペンチル基、n-ヘキシル基、iso-ヘキシル基、tert-ヘキシル基等を挙げることができる。炭素原子数1~6のアルキル基は、直鎖状であっても分枝状であってもよい。
重水素原子;
シアノ基;
ニトロ基;
ハロゲン原子、例えばフッ素原子、塩素原子、臭素原子、ヨウ素原子
等;
炭素原子数1~6のアルキルオキシ基、例えばメチルオキシ基、エチ
ルオキシ基、プロピルオキシ基等;
アルケニル基、例えばビニル基、アリル基等;
アリールオキシ基、例えばフェニルオキシ基、トリルオキシ基等;
アリールアルキルオキシ基、例えばベンジルオキシ基、フェネチルオ
キシ基等;
芳香族炭化水素基または縮合多環芳香族基、例えばフェニル基、ビフ
ェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェ
ナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレ
ニル基、フルオランテニル基、トリフェニレニル基等;
芳香族複素環基、例えばピリジル基、ピリミジニル基、トリアジニル
基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基
、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル
基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、
ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾ
チエニル基、フェノキサジニル基、フェノチアジニル基、カルボリニル
基、アクリジニル基、フェナジニル基等;
炭素原子数1~6のアルキルオキシ基は直鎖状であっても分岐状であってもよい。これらの置換基は、さらに、前記例示した置換基で置換されていてもよい。置換基同士は、互いに独立して存在してもよいが、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。
R1~R4で表される芳香族複素環基としては、具体的に、トリアジニル基、ピリジル基、ピリミジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、アザフルオレニル基、ジアザフルオレニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、カルボリニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基等を挙げることができる。
好適なAr1としては、芳香族炭化水素基または縮合多環芳香族基を挙げることができる。芳香族炭化水素基も縮合多環芳香族基も無置換であってもよいし、置換基を有していてもよい。
特に好適なAr1としては、フェニル基、ナフチル基、フェナントレニル基、フルオレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基、スピロビフルオレニル基、ジベンゾフラニル基、ジベンゾチエニル基を挙げることができる。
好適な或いは特に好適なAr1である縮合多環芳香族基および含酸素もしくは含硫黄芳香族複素環基は、無置換であってもよく、置換基を有していてもよい。
また、上記の好適な或いは特に好適なAr1であるフェニル基は、無置換でもよいが、置換基を有していることが好ましい。
フェニル基が有する置換基としては、フェニル基、ビフェニル基、縮合多環芳香族基が好適である。
特に、フェニル基が有する置換基としては、フェニル基、ビフェニル基、ナフチル基、フェナントレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基、スピロビフルオレニル基が好適である。
フェニル基が有する置換基である縮合多環芳香族基は、更に置換基を有していてもよく、無置換でもよい。また、フェニル基と当該置換基とは、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよいが、それぞれ独立して存在して環を形成していなくてもよい。
好適なAr2としては、水素原子、芳香族炭化水素基または縮合多環芳香族基を挙げることができる。芳香族炭化水素基も縮合多環芳香族基も、無置換であってもよいし、置換基を有していてもよい。
スピロビフルオレニル基および含酸素もしくは含硫黄芳香族複素環基は、置換基を有していてもよく、無置換でもよい。
フェニル基は、置換基を有することが好ましい。フェニル基が有する置換基としては、芳香族炭化水素基、縮合多環芳香族基または含酸素もしくは含硫黄芳香族複素環基が好ましい。具体的には、フェニル基、ビフェニリル基、ターフェニル基などの芳香族炭化水素基;ナフチル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、スピロビフルオレニル基などの縮合多環芳香族基;フリル基、ベンゾフラニル基、ジベンゾフラニル基等の含酸素芳香族複素環基;チエニル基、ベンゾチエニル基、ジベンゾチエニル基等の含硫黄芳香族複素環基;が好ましく、フェニル基、ナフチル基、フェナントレニル基、フルオレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基、スピロビフルオレニル基、ジベンゾフラニル基、ジベンゾチエニル基がより好ましい。上述のフェニル基が有する好適な置換基は、更に置換基を有していてもよいが、無置換でもよい。また、フェニル基と当該置換基とは、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよいが、それぞれ独立して存在して環を形成していなくてもよい。
好適なAr3として、水素原子、芳香族炭化水素基または縮合多環芳香族基を挙げることができる。芳香族炭化水素基も縮合多環芳香族基も、無置換であってもよいし、置換基を有していてもよい。
好適な或いはより好適なAr3であるスピロビフルオレニル基、含酸素もしくは含硫黄芳香族複素環基は、置換基を有していてもよく、無置換でもよい。
好適な或いはより好適なAr3であるフェニル基は、置換基を有していることが好ましい。フェニル基が有する置換基としては、芳香族炭化水素基、縮合多環芳香族基、含酸素もしくは含硫黄芳香族複素環基が好ましい。具体的には、フェニル基、ビフェニル基、ターフェニル基、ナフチル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、スピロビフルオレニル基、フリル基、ベンゾフラニル基、ジベンゾフラニル基、チエニル基、ベンゾチエニル基、ジベンゾチエニル基が好ましい。
特に、フェニル基が有する置換基としては、フェニル基、ナフチル基、フェナントレニル基、フルオレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基、スピロビフルオレニル基、ジベンゾフラニル基、ジベンゾチエニル基が好ましい。
フェニル基が置換基を有する場合、当該置換基とフェニル基とは、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよいが、それぞれ独立して存在して環を形成していなくてもよい。
Ar2とAr3は同一の基であってもよいが、分子全体の対称性が増すと結晶化し易くなる虞があるので、薄膜の安定性の観点から、異なる基であることが好ましい。
また、Ar2とAr3の一方が水素原子であることが好ましく、Ar3が水素原子であることが特に好ましい。尚、既に述べたように、本発明において、Ar2とAr3が同時に水素原子とはなることはない。
基Aは、薄膜の安定性の観点から、下記構造式(2-1)で示されることが好ましく、即ち、基Ar4が、ベンゼン環において、一般式(1)で示されるピリミジン環に対してメタ位で結合していることが好ましい。
あるいは、基Aは、合成上の観点から、下記構造式(2-2)に示されることが好ましく、即ち、基Ar4が、ベンゼン環において、一般式(1)で示されるピリミジン環に対してパラ位で結合していることが好ましい。
より好適なAr4としては、トリアジニル基、ピリジル基、ピリミジニル基、キノリル基、イソキノリル基、インドリル基、キノキサリニル基、アザフルオレニル基、ジアザフルオレニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基を挙げることができる。
最も好適なAr4としては、ピリジル基、ピリミジニル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基を挙げることができる。
ここで、ピリジル基としては、ピリジン-3-イル基が好ましい。
本発明のピリミジン誘導体は、例えば、以下の方法により製造することができる。即ち、2,4,6-トリクロロピリミジンと、4位に相当する基を有するアリールボロン酸もしくはアリールボロン酸エステルとの鈴木カップリング反応を行い、続いて、相当するヘテロアリール基を置換基として有するフェニルボロン酸もしくはフェニルボロン酸エステルを加え、鈴木カップリング反応を行う。かかる2段階の鈴木カップリング反応によって、ピリミジン環の4位に、相当する基を導入し、且つ、6位に、相当するヘテロアリール基を置換基として有するフェニル基を導入する。更に、2位に相当する基を有するアリールボロン酸もしくはアリールボロン酸エステルを用い、鈴木カップリング反応を行うことによって、ピリミジン環の2位に、相当する基を導入し、本発明のピリミジン誘導体を製造することができる。
更に、上記製造方法において、2,4,6-トリクロロピリミジンに替えて、2,4,5-トリクロロピリミジン等、クロロ基等のハロゲン原子が異なる位置に置換したピリミジンを用いると、置換位置の異なるピリミジン誘導体を製造することができる。
ガラス転移点(Tg)は薄膜状態の安定性の指標となる。ガラス転移点(Tg)は、例えば、粉体を用いて高感度示差走査熱量計(ブルカー・エイエックスエス製、DSC3100S)によって測定することができる。
A:式(2-1)
Ar3:H (化合物114)
A:式(2-2)
Ar3:H (化合物132)
一対の電極の間に、上述した本発明のピリミジン誘導体を用いて形成される有機層を少なくとも1層備えた有機EL素子(以下、本発明の有機EL素子と呼ぶことがある。)は、例えば図24に示す層構造をしている。即ち、本発明の有機EL素子においては、例えば、基板上に順次、陽極2、正孔注入層3、正孔輸送層4、発光層5、正孔阻止層6、電子輸送層7、電子注入層8、陰極9が設けられている。
本発明の有機EL素子は、かかる構造に限定されるものではなく、例えば、正孔輸送層4と発光層5の間に電子阻止層(図示せず)を設けてもよい。これらの多層構造においては有機層を何層か省略してもよく、例えば、陽極2と正孔輸送層4の間の正孔注入層3や、発光層5と電子輸送層7の間の正孔阻止層6、電子輸送層7と陰極9の間の電子注入層8を省略し、基板1上に順次に、陽極2、正孔輸送層4、発光層5、電子輸送層7、陰極9を有する構成とすることもできる。
銅フタロシアニンに代表されるポルフィリン化合物;
スターバースト型のトリフェニルアミン誘導体;
トリフェニルアミン3量体および4量体、例えば分子中にトリフェニ
ルアミン構造を3個以上、単結合またはヘテロ原子を含まない2価基で
連結した構造を有するアリールアミン化合物;
アクセプター性の複素環化合物、例えばヘキサシアノアザトリフェニ
レン;
塗布型の高分子材料;
正孔注入層3(薄膜)は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって形成することができる。以下に述べる各種の層も同様に、蒸着やスピンコート、インクジェットなどの公知の方法により成膜することができる。
ベンジジン誘導体、例えば
N,N’-ジフェニル-N,N’-ジ(m-トリル)-ベンジジン
(以後、TPDと略称する)、
N,N’-ジフェニル-N,N’-ジ(α-ナフチル)-ベンジジ
ン(以後、NPDと略称する)、
N,N,N’,N’-テトラビフェニリルベンジジン;
1,1-ビス[(ジ-4-トリルアミノ)フェニル]シクロヘキサン
(以後、TAPCと略称する);
種々のトリフェニルアミン3量体および4量体;
上述の正孔輸送材料は、単独で成膜に用いても良いが、他の材料と混合して成膜してもよく、また、正孔輸送層を、単独で成膜した層同士、混合して成膜した層同士または単独で成膜した層と混合して成膜した層とを積層した積層構造としても良い。
カルバゾール誘導体、例えば
4,4’,4’’-トリ(N-カルバゾリル)トリフェニルアミン
(以後、TCTAと略称する)、
9,9-ビス[4-(カルバゾール-9-イル)フェニル]フルオ
レン、
1,3-ビス(カルバゾール-9-イル)ベンゼン(以後、mCP
と略称する)、
2,2-ビス(4-カルバゾール-9-イルフェニル)アダマンタ
ン(以後、Ad-Czと略称する);
トリフェニルシリル基とトリアリールアミン構造を有する化合物、例
えば
9-[4-(カルバゾール-9-イル)フェニル]-9-[4-(
トリフェニルシリル)フェニル]-9H-フルオレン;
上述の電子阻止層材料は、単独で成膜に用いても良いが、他の材料と混合して成膜してもよく、また、電子阻止層を、単独で成膜した層同士、混合して成膜した層同士または単独で成膜した層と混合して成膜した層とを積層した積層構造としても良い。
Alq3をはじめとするキノリノール誘導体の金属錯体;
各種の金属錯体;
アントラセン誘導体;
ビススチリルベンゼン誘導体;
ピレン誘導体;
オキサゾール誘導体;
ポリパラフェニレンビニレン誘導体;
ドーパント材料としては、キナクリドン、クマリン、ルブレン、ペリレンおよびそれらの誘導体;ベンゾピラン誘導体;ローダミン誘導体;アミノスチリル誘導体;等を用いることができる。
緑色の燐光発光体、例えばIr(ppy)3;
青色の燐光発光体、例えばFIrpic、FIr6;
赤色の燐光発光体、例えばBtp2Ir(acac);
等が用いられる。この場合のホスト材料のうち正孔注入・輸送性のホスト材料としては、本発明のピリミジン誘導体に加え、
カルバゾール誘導体、例えば
4,4’-ジ(N-カルバゾリル)ビフェニル(以後、CBPと略
称する)、
TCTA、
mCP;
を用いることができる。電子輸送性のホスト材料としては、
p-ビス(トリフェニルシリル)ベンゼン(以後、UGH2と略称す
る);
2,2’,2’’-(1,3,5-フェニレン)-トリス(1-フェ
ニル-1H-ベンズイミダゾール)(以後、TPBIと略称する);
を用いることができる。これらを用いることで、高性能の有機EL素子を作製することができる。
フェナントロリン誘導体、例えばバソクプロイン(以後、BCPと略
称する);
キノリノール誘導体の金属錯体、例えばBAlq;
各種の希土類錯体;
オキサゾール誘導体;
トリアゾール誘導体;
トリアジン誘導体;
正孔阻止材料も、単独で成膜に用いても良いが、他の材料と混合して成膜してもよく、また、正孔阻止層を、単独で成膜した層同士、混合して成膜した層同士または単独で成膜した層と混合して成膜した層とを積層した積層構造としても良い。
Alq3、BAlqをはじめとするキノリノール誘導体の金属錯体;
各種金属錯体;
トリアゾール誘導体;
トリアジン誘導体;
オキサジアゾール誘導体;
ピリジン誘導体;
ベンズイミダゾール誘導体;
チアジアゾール誘導体;
アントラセン誘導体;
カルボジイミド誘導体;
キノキサリン誘導体;
ピリドインドール誘導体;
フェナントロリン誘導体;
シロール誘導体;
電子輸送材料も、単独で成膜に用いても良いが、他の材料と混合して成膜してもよく、また、電子輸送層を、単独で成膜した層同士、混合して成膜した層同士または単独で成膜した層と混合して成膜した層とを積層した積層構造としても良い。
フッ化リチウム、フッ化セシウムなどのアルカリ金属塩;
フッ化マグネシウムなどのアルカリ土類金属塩;
リチウムキノリノールなどのキノリノール誘導体の金属錯体;
酸化アルミニウムなどの金属酸化物
電子注入層8は、電子輸送層と陰極の好ましい選択においては、省略することができる。
4-(ビフェニル-4-イル)-2-{3-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジンの合成;
A:式(2-2)
Ar3:H (化合物74)
窒素置換した反応容器に、
3-(ナフタレン-1-イル)フェニルボロン酸 5.0g、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン 7.0g、
テトラキストリフェニルホスフィン 0.96g、
炭酸カリウム 6.9g、
トルエン 35ml、
1,4-ジオキサン 70ml及び
水 35ml
を加えて加熱し、85℃で12時間撹拌した。室温まで冷却し、分液操作によって有機層を採取した後、減圧下濃縮することによって粗製物を得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ヘプタン/ジクロロメタン/THF)による精製を行った後、クロロベンゼン/ジクロロメタンの混合溶媒を用いた再結晶による精製を行うことによって、4-(ビフェニル-4-イル)-2-{3-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物74)の白色粉体3.1g(収率32%)を得た。
δ(ppm)=8.97-8.84(3H)、
8.60-8.45(6H)、
8.08-7.32(20H)
4-(ビフェニル-3-イル)-2-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物84)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(ナフタレン-1-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-(ビフェニル-3-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、4-(ビフェニル-3-イル)-2-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物84)の白色粉体3.8g(収率39%)を得た。
δ(ppm)=8.99(1H)、
8.93(2H)、
8.72(1H)、
8.65(2H)、
8.59(1H)、
8.52(1H)、
8.49(1H)、
8.09(1H)、
8.04-7.34(19H)
4-(ビフェニル-3-イル)-2-{3-(ナフタレン-2-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物89)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
3-(ナフタレン-2-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-(ビフェニル-3-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、4-(ビフェニル-3-イル)-2-{3-(ナフタレン-2-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物89)の黄色粉体5.8g(収率59%)を得た。
δ(ppm)=9.21(1H)、
8.98(1H)、
8.80(1H)、
8.74(1H)、
8.64(2H)、
8.59(1H)、
8.53(1H)、
8.46(1H)、
8.29(1H)、
8.08(1H)、
8.00-7.76(10H)、
7.72-7.62(2H)、
7.55-6.34(6H)
2-{3-(ナフタレン-1-イル)フェニル}-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物130)
実施例1において、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(フェナントレン-9-イル)フェニル}-
6-{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{3-(ナフタレン-1-イル)フェニル}-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物130)の黄色粉体9.3g(収率35%)を得た。
δ(ppm)=8.98-8.84(3H)、
8.84(1H)、
8.78(1H)、
8.68(1H)、
8.47-8.44(4H)、
8.19(1H)、
8.06-7.93(6H)、
7.81-7.41(16H)
2-{4-(ナフタレン-1-イル)フェニル}-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物131)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(ナフタレン-1-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(フェナントレン-9-イル)フェニル}-
6-{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(ナフタレン-1-イル)フェニル}-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物131)の黄色粉体22.6g(収率85%)を得た。
δ(ppm)=9.00(1H)、
8.94(2H)、
8.85(1H)、
8.78(1H)、
8.69(1H)、
8.55-8.51(4H)、
8.23(1H)、
8.23-7.44(22H)
2-{4-(ナフタレン-1-イル)フェニル}-4-{3-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物92)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(ナフタレン-1-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{3-(ナフタレン-1-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(ナフタレン-1-イル)フェニル}-4-{3-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物92)の黄色粉体6g(収率74%)を得た。
δ(ppm)=8.98(1H)、
8.87(2H)、
8.67(1H)、
8.48-8.46(4H)、
8.16(1H)、
8.04-7.82(7H)、
7.80(2H)、
7.76-7.42(13H)
2-{4-(フェナントレン-9-イル)フェニル}-4-{3-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物136)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(フェナントレン-9-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{3-(ナフタレン-1-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(フェナントレン-9-イル)フェニル}-4-{3-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物136)の黄色粉体2g(収率26%)を得た。
δ(ppm)=8.98(1H)、
8.90(2H)、
8.83(1H)、
8.78(1H)、
8.68(1H)、
8.50-8.45(4H)、
8.17(1H)、
8.04-7.94(6H)、
7.83-7.41(16H)
2-{4-(ナフタレン-1-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物125)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(ナフタレン-1-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(ナフタレン-1-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(ナフタレン-1-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物125)の黄色粉体21.6g(収率80%)を得た。
δ(ppm)=9.00(1H)、
8.95(2H)、
8.68(1H)、
8.54-8.48(4H)、
8.22(1H)、
8.21-7.91(7H)、
7.82(2H)、
7.79-7.72(4H)、
7.64-7.42(9H)
2-{4-(ナフタレン-2-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物138)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(ナフタレン-2-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(ナフタレン-1-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(ナフタレン-2-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物138)の黄色粉体3.5g(収率43%)を得た。
δ(ppm)=9.00(1H)、
8.92(2H)、
8.68(1H)、
8.53-8.48(4H)、
8.20(2H)、
8.03-7.81(12H)、
7.77(2H)、
7.63-7.42(7H)
2-{4-(フェナントレン-9-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物78)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(フェナントレン-9-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(ナフタレン-1-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(フェナントレン-9-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}-ピリミジン(化合物78)の黄色粉体16.2g(収率56%)を得た。
δ(ppm)=9.00(1H)、
8.95(2H)、
8.83(1H)、
8.76(1H)、
8.69(1H)、
8.52-8.48(4H)、
8.22(1H)、
8.08-7.91(6H)、
7.86-7.42(16H)
2-{4-(ナフタレン-1-イル)フェニル}-4-{3-(ナフタレン-2-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物76)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(ナフタレン-1-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{3-(ナフタレン-2-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(ナフタレン-1-イル)フェニル}-4-{3-(ナフタレン-2-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物76)の黄色粉体24.0g(収率52%)を得た。
δ(ppm)=9.00(1H)、
8.90(2H)、
8.68(2H)、
8.53(2H)、
8.37(1H)、
8.21(2H)、
8.08-7.81(11H)、
7.78-7.71(3H)、
7.64-7.42(7H)
2-(ビフェニル-4-イル)-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物126)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-ビフェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(フェナントレン-9-イル)フェニル}-
6-{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-(ビフェニル-4-イル)-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物126)の黄色粉体6.5g(収率85%)を得た。
δ(ppm)=9.00(1H)、
8.92-8.76(4H)、
8.68(1H)、
8.54-8.46(4H)、
8.18(1H)、
8.05-7.94(3H)、
7.88-7.38(17H)
2-(ビフェニル-4-イル)-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物124)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-ビフェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(ナフタレン-1-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-(ビフェニル-4-イル)-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物124)の黄色粉体17.6g(収率64%)を得た。
δ(ppm)=9.00(1H)、
8.89(2H)、
8.67(1H)、
8.51-8.48(4H)、
8.17(1H)、
8.03-7.93(4H)、
7.86-7.81(4H)、
7.78-7.72(4H)、
7.63-7.38(8H)
2-(ビフェニル-3-イル)-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物123)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
3-ビフェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(フェナントレン-9-イル)フェニル}-
6-{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-(ビフェニル-3-イル)-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物123)の黄色粉体3.0g(収率38%)を得た。
δ(ppm)=9.02(2H)、
8.86-8.76(3H)、
8.69(1H)、
8.52-8.48(4H)、
8.21(1H)、
8.05-7.93(3H)、
7.89-7.40(17H)
2-{4-(ナフタレン-1-イル)フェニル}-4-(ビフェニル-4-イル)-6-{4-(キノリン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物146)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(ナフタレン-1-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(キノリン
-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(ナフタレン-1-イル)フェニル}-4-(ビフェニル-4-イル)-6-{4-(キノリン-3-イル)フェニル}ピリミジン(化合物146)の黄色粉体1.2g(収率15%)を得た。
δ(ppm)=9.34(1H)、
8.91(2H)、
8.62-8.52(4H)、
8.37(1H)、
8.22(1H)、
8.14-7.90(5H)、
7.86-7.40(17H)
2-{3-(フェナントレン-9-イル)フェニル}-4-{3-(ナフタレン-2-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物98)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
3-(フェナントレン-9-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{3-(ナフタレン-2-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{3-(フェナントレン-9-イル)フェニル}-4-{3-(ナフタレン-2-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物98)の黄色粉体5.0g(収率57%)を得た。
δ(ppm)=8.98-8.78(5H)、
8.68-8.62(2H)、
8.45(2H)、
8.32(1H)、
8.17(2H)、
8.03(1H)、
8.00-7.39(20H)
2-{3-(ナフタレン-2-イル)フェニル}-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物153)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
3-(ナフタレン-2-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(フェナントレン-9-イル)フェニル}-
6-{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{3-(ナフタレン-2-イル)フェニル}-4-{4-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物153)の黄色粉体15.4g(収率73%)を得た。
δ(ppm)=9.15(1H)、
9.00(1H)、
8.83(2H)、
8.78(1H)、
8.68(1H)、
8.53-8.47(4H)、
8.22(2H)、
8.04-7.42(21H)
2-{4-(ナフタレン-1-イル)フェニル}-4-{3-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物155)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
4-(ナフタレン-1-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{3-(フェナントレン-9-イル)フェニル}-
6-{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{4-(ナフタレン-1-イル)フェニル}-4-{3-(フェナントレン-9-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物155)の黄色粉体2.5g(収率42%)を得た。
δ(ppm)=8.97(1H)、
8.97-8.76(4H)、
8.67(1H)、
8.52-8.46(4H)、
8.17(1H)、
8.01-7.43(22H)
2-{3-(フェナントレン-9-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物82)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
3-(フェナントレン-9-イル)フェニルボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(ナフタレン-1-イル)フェニル}-6-
{4-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{3-(フェナントレン-9-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(ピリジン-3-イル)フェニル}ピリミジン(化合物82)の黄色粉体6.3g(収率72%)を得た。
δ(ppm)=8.97-8.88(3H)、
8.87-8.76(2H)、
8.66(1H)、
8.49-8.42(4H)、
8.20(1H)、
8.08-7.84(7H)、
7.83-7.40(15H)
2-{3-(ナフタレン-1-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(キノリン-3-イル)フェニル}ピリミジン;
A:式(2-2)
Ar3:H (化合物182)
実施例1において、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(ナフタレン-1-イル)フェニル}-6-
{4-(キノリン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-{3-(ナフタレン-1-イル)フェニル}-4-{4-(ナフタレン-1-イル)フェニル}-6-{4-(キノリン-3-イル)-フェニル}ピリミジン(化合物182)の黄色粉体1.5g(収率23%)を得た。
δ(ppm)=9.33(1H)、
8.94(2H)、
8.59-8.42(5H)、
8.23-8.17(2H)、
8.04-7.90(9H)、
7.82-7.72(5H)、
7.64-7.45(9H)
2-(9,9’-スピロビ[9H-フルオレン]-2-イル)-4-{4-(ナフタレン-1-イル)フェニル}-6-{3-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-1)
Ar3:H (化合物227)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
9,9’-スピロビ[9H-フルオレン]-2-ボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(ナフタレン-1-イル)フェニル}-6-
{3-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-(9,9’-スピロビ[9H-フルオレン]-2-イル)-4-{4-(ナフタレン-1-イル)フェニル}-6-{3-(ピリジン-3-イル)フェニル}ピリミジン(化合物227)の黄色粉体1.3g(収率20%)を得た。
δ(ppm)=8.95(1H)、
8.86(1H)、
8.70(1H)、
8.42(1H)、
8.30(2H)、
8.22(1H)、
8.12-、8.03(3H)、
8.01-7.89(7H)、
7.74(1H)、
7.67-7.37(11H)、
7.20-7.10(3H)、
6.83(2H)、
6.78(1H)
2-(9,9’-スピロビ[9H-フルオレン]-2-イル)-4-(ビフェニル-4-イル)-6-{3-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-1)
Ar3:H (化合物234)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
9,9’-スピロビ[9H-フルオレン]-2-ボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-(ビフェニル-4-イル}-6-{3-(ピリジン
-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-(9,9’-スピロビ[9H-フルオレン]-2-イル)-4-(ビフェニル-4-イル)-6-{3-(ピリジン-3-イル)フェニル}ピリミジン(化合物234)の白色粉体1.5g(収率25%)を得た。
δ(ppm)=8.96(1H)、
8.86(1H)、
8.72(1H)、
8.39(1H)、
8.26(2H)、
8.17(1H)、
8.12-7.89(7H)、
7.78-7.60(6H)、
7.53-7.25(7H)、
7.21-7.10(3H)、
6.83-6.75(3H)
2-(9,9’-スピロビ[9H-フルオレン]-2-イル)-4-{4-(ナフタレン-2-イル)フェニル}-6-{3-(ピリジン-3-イル)フェニル}ピリミジン;
A:式(2-1)
Ar3:H (化合物235)
実施例1において、
3-(ナフタレン-1-イル)フェニルボロン酸
に代えて
9,9’-スピロビ[9H-フルオレン]-2-ボロン酸
を用い、
2-クロロ-4-(ビフェニル-4-イル)-6-{4-(ピリジン
-3-イル)フェニル}ピリミジン
に代えて
2-クロロ-4-{4-(ナフタレン-2-イル)フェニル}-6-
{3-(ピリジン-3-イル)フェニル}ピリミジン
を用い、同様の条件で反応を行った。その結果、2-(9,9’-スピロビ[9H-フルオレン]-2-イル)-4-{4-(ナフタレン-2-イル)フェニル}-6-{3-(ピリジン-3-イル)フェニル}ピリミジン(化合物235)の白色粉体2.0g(収率32%)を得た。
δ(ppm)=8.96(1H)、
8.85(1H)、
8.71(1H)、
8.41(1H)、
8.30(2H)、
8.19(1H)、
8.12(1H)、
8.79-7.39(21H)、
7.20-7.11(3H)、
6.83(2H)、
6.78(1H)
本発明の化合物を用いて、ITO基板の上に膜厚100nmの蒸着膜を作製して、イオン化ポテンシャル測定装置(住友重機械工業株式会社製、PYS-202型)で仕事関数を測定した。
仕事関数
実施例1の化合物(化合物74) 6.63eV
実施例2の化合物(化合物84) 6.60eV
実施例3の化合物(化合物89) 6.39eV
実施例4の化合物(化合物130) 6.50eV
実施例5の化合物(化合物131) 6.50eV
実施例6の化合物(化合物92) 6.51eV
実施例7の化合物(化合物136) 6.47eV
実施例8の化合物(化合物125) 6.50eV
実施例9の化合物(化合物138) 6.47eV
実施例10の化合物(化合物78) 6.48eV
実施例11の化合物(化合物76) 6.55eV
実施例12の化合物(化合物126) 6.56eV
実施例13の化合物(化合物124) 6.50eV
実施例14の化合物(化合物123) 6.53eV
実施例15の化合物(化合物146) 6.53eV
実施例16の化合物(化合物98) 6.48eV
実施例17の化合物(化合物153) 6.46eV
実施例18の化合物(化合物155) 6.51eV
実施例19の化合物(化合物82) 6.46eV
実施例20の化合物(化合物182) 6.54eV
実施例21の化合物(化合物227) 6.55eV
実施例22の化合物(化合物234) 6.55eV
実施例23の化合物(化合物235) 6.54eV
このように本発明の化合物はNPD、TPDなどの一般的な正孔輸送材料がもつ仕事関数5.5eVより大きい値を有しており、大きな正孔阻止能力を有している。
実施例4~23で得られた化合物について、高感度示差走査熱量計(ブルカー・エイエックスエス製、DSC3100S)を用いてガラス転移点を求めた。
ガラス転移点
実施例4の化合物(化合物130) 129℃
実施例5の化合物(化合物131) 138℃
実施例6の化合物(化合物92) 108℃
実施例7の化合物(化合物136) 128℃
実施例8の化合物(化合物125) 117℃
実施例9の化合物(化合物138) 111℃
実施例10の化合物(化合物78) 138℃
実施例11の化合物(化合物76) 103℃
実施例12の化合物(化合物126) 129℃
実施例13の化合物(化合物124) 107℃
実施例14の化合物(化合物123) 116℃
実施例15の化合物(化合物146) 114℃
実施例16の化合物(化合物98) 116℃
実施例17の化合物(化合物153) 116℃
実施例18の化合物(化合物155) 132℃
実施例19の化合物(化合物82) 131℃
実施例20の化合物(化合物182) 114℃
実施例21の化合物(化合物227) 150℃
実施例22の化合物(化合物234) 143℃
実施例23の化合物(化合物235) 146℃
本発明の化合物は100℃以上、特に140℃以上のガラス転移点を有している。このことは、本発明の化合物において薄膜状態が安定であることを示す。
有機EL素子は、図24に示すように、ガラス基板1上に透明陽極2としてITO電極をあらかじめ形成したものの上に、正孔注入層3、正孔輸送層4、発光層5、正孔阻止層6、電子輸送層7、電子注入層8、陰極(アルミニウム電極)9の順に蒸着して作製した。
表1に示す通り、正孔阻止層6兼電子輸送層7の材料として、実施例1の化合物(化合物74)に代えて実施例2~20の化合物を用い、それ以外は有機EL素子実施例1と同様の条件で有機EL素子を作製した。
比較のために、有機EL素子実施例1において、正孔阻止層6兼電子輸送層7の材料として、実施例1の化合物(化合物74)に代えて、下記構造式の化合物ETM-2(特許文献4参照)を用い、それ以外は有機EL素子実施例1と同様の条件で有機EL素子を作製した。
電力効率についても、有機EL素子比較例1が5.20lm/Wであるのに対し、有機EL素子実施例1~20では5.76~6.98lm/Wと大きく向上した。
特に、素子寿命(95%減衰)においては、有機EL素子比較例1における55時間に対し、有機EL素子実施例1~20では128~276時間と、大きく長寿命化した。このように長寿命化を実現できたのは、本発明のピリミジン誘導体が、従来の有機EL素子用材料に比べて薄膜状態が安定しており、耐熱性に優れているためと考えられる。また、本発明のピリミジン誘導体のキャリアバランスが優れているためと推察される。
更に、駆動電圧について、有機EL素子実施例1~20の値は、有機EL素子比較例1と同程度、あるいはそれ以上に低かった。
2 透明陽極
3 正孔注入層
4 正孔輸送層
5 発光層
6 正孔阻止層
7 電子輸送層
8 電子注入層
9 陰極
Claims (21)
- 下記一般式(1)で表される、ピリミジン誘導体;
Ar1は、芳香族炭化水素基、縮合多環芳香族基または芳
香族複素環基を表し、
Ar2、Ar3は同一でも異なっていてもよく、水素原子
、芳香族炭化水素基、縮合多環芳香族基または芳香族複素環
基を表し、
Ar2とAr3は同時に水素原子となることはなく、
Aは、下記構造式(2)で示される1価基を表す、
Ar4は、芳香族複素環基を表し、
R1~R4は、同一でも異なってもよく、水素原子、
重水素原子、フッ素原子、塩素原子、シアノ基、トリフ
ルオロメチル基、炭素原子数1~6のアルキル基、芳香
族炭化水素基、縮合多環芳香族基または芳香族複素環基
を表し、
R1~R4とAr4は単結合、メチレン基、酸素原子
または硫黄原子を介して互いに結合して環を形成してい
てもよい。 - Ar1が、芳香族炭化水素基または縮合多環芳香族基を表し、Ar2、Ar3は同一でも異なってもよく、水素原子、芳香族炭化水素基または縮合多環芳香族基を表す、請求項1記載のピリミジン誘導体。
- Ar4がピリジル基、ピリミジニル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基またはジアザスピロビフルオレニル基である、請求項1記載のピリミジン誘導体。
- Ar2が置換基を有するフェニル基である、請求項1記載のピリミジン誘導体。
- Ar2が置換基を有するフェニル基であり、
該置換基が、芳香族炭化水素基、または縮合多環芳香族基である、請求項8記載のピリミジン誘導体。 - Ar2が置換基を有するフェニル基であり、
該置換基が、芳香族炭化水素基である、請求項9記載のピリミジン誘導体。 - Ar2が置換基を有するフェニル基であり、
該置換基が、縮合多環芳香族基である、請求項9記載のピリミジン誘導体。 - Ar3が水素原子である、請求項1記載のピリミジン誘導体。
- Ar1が置換基を有するフェニル基である、請求項1記載のピリミジン誘導体。
- Ar1が置換基を有するフェニル基であり、
該置換基が、縮合多環芳香族基である、請求項13記載のピリミジン誘導体。 - Ar1が縮合多環芳香族基である、請求項1記載のピリミジン誘導体。
- Ar1が無置換のフェニル基である、請求項1記載のピリミジン誘導体。
- 一対の電極とその間に挟まれた少なくとも一層の有機層を有する有機エレクトロルミネッセンス素子において、請求項1記載のピリミジン誘導体が、少なくとも1つの有機層の構成材料として用いられていることを特徴とする有機エレクトロルミネッセンス素子。
- 前記ピリミジン誘導体が用いられている有機層が電子輸送層である請求項17記載の有機エレクトロルミネッセンス素子。
- 前記ピリミジン誘導体が用いられている有機層が正孔阻止層である請求項17記載の有機エレクトロルミネッセンス素子。
- 前記ピリミジン誘導体が用いられている有機層が発光層である請求項17記載の有機エレクトロルミネッセンス素子。
- 前記ピリミジン誘導体が用いられている有機層が電子注入層である請求項17記載の有機エレクトロルミネッセンス素子。
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Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016076384A1 (ja) * | 2014-11-14 | 2016-05-19 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
WO2016104289A1 (ja) * | 2014-12-24 | 2016-06-30 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
WO2016111269A1 (ja) * | 2015-01-08 | 2016-07-14 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
WO2016200080A1 (ko) * | 2015-06-12 | 2016-12-15 | 에스에프씨 주식회사 | 고효율을 갖는 유기 발광 소자 |
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EP3663289A1 (en) | 2020-06-10 |
CN106573911A (zh) | 2017-04-19 |
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TWI721379B (zh) | 2021-03-11 |
US20200303658A1 (en) | 2020-09-24 |
KR20170016936A (ko) | 2017-02-14 |
EP3156402A4 (en) | 2017-12-06 |
TW201920148A (zh) | 2019-06-01 |
US20170186967A1 (en) | 2017-06-29 |
CN111205270B (zh) | 2023-04-28 |
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EP3156402B1 (en) | 2021-11-10 |
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