JP2012126673A - 縮合ピロール多環化合物、発光層用材料およびこれを用いた有機電界発光素子 - Google Patents
縮合ピロール多環化合物、発光層用材料およびこれを用いた有機電界発光素子 Download PDFInfo
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- JP2012126673A JP2012126673A JP2010279234A JP2010279234A JP2012126673A JP 2012126673 A JP2012126673 A JP 2012126673A JP 2010279234 A JP2010279234 A JP 2010279234A JP 2010279234 A JP2010279234 A JP 2010279234A JP 2012126673 A JP2012126673 A JP 2012126673A
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- 239000000463 material Substances 0.000 title claims abstract description 127
- -1 pyrrole polycyclic compound Chemical class 0.000 title claims description 158
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 261
- 125000003118 aryl group Chemical group 0.000 claims abstract description 55
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 24
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002347 injection Methods 0.000 claims description 73
- 239000007924 injection Substances 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 238000005401 electroluminescence Methods 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000003003 spiro group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 14
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 12
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000005561 phenanthryl group Chemical group 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 10
- 150000002910 rare earth metals Chemical class 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 9
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- 150000004696 coordination complex Chemical class 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 6
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims description 5
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 150000008045 alkali metal halides Chemical class 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 229910001404 rare earth metal oxide Inorganic materials 0.000 claims description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004623 carbolinyl group Chemical group 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 abstract description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 205
- 229910052757 nitrogen Inorganic materials 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 55
- 230000032258 transport Effects 0.000 description 53
- 229910052782 aluminium Inorganic materials 0.000 description 44
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 44
- 239000000758 substrate Substances 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000002019 doping agent Substances 0.000 description 30
- 229910052751 metal Inorganic materials 0.000 description 29
- 239000002184 metal Substances 0.000 description 29
- 0 C1C=CC=*C1C1(c(cccc2)c2C(C=CC23)=C1C2c1ccccc1N3c1c(cccc2)c2ccc1)c1ncccc1 Chemical compound C1C=CC=*C1C1(c(cccc2)c2C(C=CC23)=C1C2c1ccccc1N3c1c(cccc2)c2ccc1)c1ncccc1 0.000 description 28
- 230000005525 hole transport Effects 0.000 description 26
- 238000007740 vapor deposition Methods 0.000 description 26
- 238000000034 method Methods 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 20
- 239000010408 film Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- 239000000523 sample Substances 0.000 description 15
- 230000005284 excitation Effects 0.000 description 14
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 14
- 239000011521 glass Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000010409 thin film Substances 0.000 description 13
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 12
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 12
- 229910052750 molybdenum Inorganic materials 0.000 description 12
- 239000011733 molybdenum Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 11
- 238000006862 quantum yield reaction Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 125000003107 substituted aryl group Chemical group 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000000151 deposition Methods 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 150000005041 phenanthrolines Chemical class 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 150000001556 benzimidazoles Chemical class 0.000 description 7
- 150000004775 coumarins Chemical class 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- 125000002524 organometallic group Chemical group 0.000 description 7
- 125000005504 styryl group Chemical group 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 229910052792 caesium Inorganic materials 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000004866 oxadiazoles Chemical class 0.000 description 6
- 150000004880 oxines Chemical class 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- 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
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 4
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 150000002220 fluorenes Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 150000003577 thiophenes Chemical class 0.000 description 4
- WGWZJNILGYTDHU-UHFFFAOYSA-K tris(3,5-dimethylphenoxy)alumane Chemical compound CC=1C=C([O-])C=C(C1)C.[Al+3].CC=1C=C([O-])C=C(C1)C.CC=1C=C([O-])C=C(C1)C WGWZJNILGYTDHU-UHFFFAOYSA-K 0.000 description 4
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
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- LEVHEXKQBUDDDG-UHFFFAOYSA-N C(C12)=CC=CC1c1ccccc1C2(c1ccc2c3c4cccc3)c3ncccc3-c1c2[n]4-c(cc1)ccc1-c(cc1)ccc1-[n]1c2ncccc2c2c1ccnc2 Chemical compound C(C12)=CC=CC1c1ccccc1C2(c1ccc2c3c4cccc3)c3ncccc3-c1c2[n]4-c(cc1)ccc1-c(cc1)ccc1-[n]1c2ncccc2c2c1ccnc2 LEVHEXKQBUDDDG-UHFFFAOYSA-N 0.000 description 1
- PHSLGSCGBRJMTP-UHFFFAOYSA-N C(C12)=CC=CC1c1ccccc1C21c(nccc2)c2C(C23)=C1C=CC2c(cccc1)c1N3c(cc1)ccc1-c(cc1)ccc1N1c2cccnc2C2C=CC=CC12 Chemical compound C(C12)=CC=CC1c1ccccc1C21c(nccc2)c2C(C23)=C1C=CC2c(cccc1)c1N3c(cc1)ccc1-c(cc1)ccc1N1c2cccnc2C2C=CC=CC12 PHSLGSCGBRJMTP-UHFFFAOYSA-N 0.000 description 1
- GJMWQYUAVBOIPY-UHFFFAOYSA-N C(C12)=CC=CC1c1ccccc1C21c2c(c3ccccc3[n]3-c4cc(cccc5)c5cc4)c3ccc2-c2ccncc12 Chemical compound C(C12)=CC=CC1c1ccccc1C21c2c(c3ccccc3[n]3-c4cc(cccc5)c5cc4)c3ccc2-c2ccncc12 GJMWQYUAVBOIPY-UHFFFAOYSA-N 0.000 description 1
- DVMRXFUTUCAYIY-UHFFFAOYSA-N C(C12)=CC=CC1c1ccncc1C21c(c(c2ccccc22)c(cc3)[n]2-c(cc2)ccc2-c(cc2)ccc2-[n](c2ccccc22)c(-c4ccccc4)c2-c2ccccc2)c3-c2ccccc12 Chemical compound C(C12)=CC=CC1c1ccncc1C21c(c(c2ccccc22)c(cc3)[n]2-c(cc2)ccc2-c(cc2)ccc2-[n](c2ccccc22)c(-c4ccccc4)c2-c2ccccc2)c3-c2ccccc12 DVMRXFUTUCAYIY-UHFFFAOYSA-N 0.000 description 1
- GAMMIQCWSQSKGP-UHFFFAOYSA-N C(C12)=CC=CC1c1ccncc1C21c2c(c3ccccc3[n]3-c(cc4)ccc4-c(cc4)ccc4-[n]4c(ccnc5)c5c5c4ccnc5)c3ccc2-c2ccccc12 Chemical compound C(C12)=CC=CC1c1ccncc1C21c2c(c3ccccc3[n]3-c(cc4)ccc4-c(cc4)ccc4-[n]4c(ccnc5)c5c5c4ccnc5)c3ccc2-c2ccccc12 GAMMIQCWSQSKGP-UHFFFAOYSA-N 0.000 description 1
- GYBRVPCUYPSNRK-UHFFFAOYSA-N C(C12)=CC=NC1c(cncc1)c1N2c(cc1)ccc1-c(cc1)ccc1-[n]1c(NC(C(C2(c3ccccc3)c3ccccc3)=C3)c4c2cccc4)c3c2c1cccc2 Chemical compound C(C12)=CC=NC1c(cncc1)c1N2c(cc1)ccc1-c(cc1)ccc1-[n]1c(NC(C(C2(c3ccccc3)c3ccccc3)=C3)c4c2cccc4)c3c2c1cccc2 GYBRVPCUYPSNRK-UHFFFAOYSA-N 0.000 description 1
- UGTJQIDRUUNHOP-UHFFFAOYSA-N C(C12)=CN=CC1c1ccncc1N2c(cc1)ccc1-c(cc1)ccc1-[n]1c2c3-c4cccnc4C4(c5ccccc5-c5ccccc45)c3ccc2c2c1cccc2 Chemical compound C(C12)=CN=CC1c1ccncc1N2c(cc1)ccc1-c(cc1)ccc1-[n]1c2c3-c4cccnc4C4(c5ccccc5-c5ccccc45)c3ccc2c2c1cccc2 UGTJQIDRUUNHOP-UHFFFAOYSA-N 0.000 description 1
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- JKDMGIAJKPTXKR-UHFFFAOYSA-N C(C1C23c(cc(c(c4c5cccc4)c4)[n]5-c5ccc(C6C=CC([n]7c(ccnc8)c8c8ccccc78)=CC6)cc5)c4-c4c2cccc4)C=CC=C1C1=C3C=CNC1 Chemical compound C(C1C23c(cc(c(c4c5cccc4)c4)[n]5-c5ccc(C6C=CC([n]7c(ccnc8)c8c8ccccc78)=CC6)cc5)c4-c4c2cccc4)C=CC=C1C1=C3C=CNC1 JKDMGIAJKPTXKR-UHFFFAOYSA-N 0.000 description 1
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- NMJDKHAVASWYLZ-UHFFFAOYSA-N C(C1c2c3cccn2)=[N]=CC1N3c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1ccc23)c1c2-c1ccccc1C31c2ncccc2-c2ccccc12 Chemical compound C(C1c2c3cccn2)=[N]=CC1N3c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1ccc23)c1c2-c1ccccc1C31c2ncccc2-c2ccccc12 NMJDKHAVASWYLZ-UHFFFAOYSA-N 0.000 description 1
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- JJVHYSBDIGPBTA-UHFFFAOYSA-N C(C=C1)Nc2c1c1cccnc1[n]2-c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1ccc23)c1c2-c1ccccc1C3(C12)c3ncccc3C1C=C1C2=C1 Chemical compound C(C=C1)Nc2c1c1cccnc1[n]2-c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1ccc23)c1c2-c1ccccc1C3(C12)c3ncccc3C1C=C1C2=C1 JJVHYSBDIGPBTA-UHFFFAOYSA-N 0.000 description 1
- PJEVHZVPYTVYIN-UHFFFAOYSA-N C(C=C1)[N-]c(c2ccccc22)c1[n]2-c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1ccc23)c1c2-c1ccccc1C31c2ncccc2C2C=CC=CC12 Chemical compound C(C=C1)[N-]c(c2ccccc22)c1[n]2-c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1ccc23)c1c2-c1ccccc1C31c2ncccc2C2C=CC=CC12 PJEVHZVPYTVYIN-UHFFFAOYSA-N 0.000 description 1
- YYJKJKZTQOSPIA-UHFFFAOYSA-N C(C=C1C(c2c3)(c4ccccc4)c4ccccc4)[N-]C=C1c2cc(c1ccccc11)c3[n]1-c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1cc(C1(c3ccccc3)c3ccccc3)c2C2=C1C=CNC2 Chemical compound C(C=C1C(c2c3)(c4ccccc4)c4ccccc4)[N-]C=C1c2cc(c1ccccc11)c3[n]1-c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1cc(C1(c3ccccc3)c3ccccc3)c2C2=C1C=CNC2 YYJKJKZTQOSPIA-UHFFFAOYSA-N 0.000 description 1
- ZAZAYSCIORMTFP-UHFFFAOYSA-N C(CC=CC1)C1C(c1ccc2c3c4C=CCC3)(c3cccnc3-c1c2[n]4-c(cc1)ccc1-c(cc1)ccc1-[n]1c2cccnc2c2cnccc12)c1ccccc1 Chemical compound C(CC=CC1)C1C(c1ccc2c3c4C=CCC3)(c3cccnc3-c1c2[n]4-c(cc1)ccc1-c(cc1)ccc1-[n]1c2cccnc2c2cnccc12)c1ccccc1 ZAZAYSCIORMTFP-UHFFFAOYSA-N 0.000 description 1
- GFXRAILZTGUXPR-UHFFFAOYSA-N C(CNC1)c(c2ccncc22)c1[n]2-c(cc1)ccc1-c(cc1)ccc1-[n]1c2nc(-c3ccccc3C3(c4ccccc4)c4ccccc4)c3cc2c2c1cccc2 Chemical compound C(CNC1)c(c2ccncc22)c1[n]2-c(cc1)ccc1-c(cc1)ccc1-[n]1c2nc(-c3ccccc3C3(c4ccccc4)c4ccccc4)c3cc2c2c1cccc2 GFXRAILZTGUXPR-UHFFFAOYSA-N 0.000 description 1
- OMLZJTAWVXETAZ-UMSFTDKQSA-N C([C@H](C=C1)[n](c2c(c3c4)nccc2)c3cc2c4-c3ccccc3C22c3ccccc3-c3c2cccc3)C=C1c(cc1)ccc1-[n]1c(NCC=C2)c2c2c1C=CC[N-]2 Chemical compound C([C@H](C=C1)[n](c2c(c3c4)nccc2)c3cc2c4-c3ccccc3C22c3ccccc3-c3c2cccc3)C=C1c(cc1)ccc1-[n]1c(NCC=C2)c2c2c1C=CC[N-]2 OMLZJTAWVXETAZ-UMSFTDKQSA-N 0.000 description 1
- LWPQLOMAKPQZLG-BHVANESWSA-N C([C@H](C=C1)[n](c2c(c3c4)nccc2)c3cc2c4-c3ccccc3C22c3ccccc3-c3ccccc23)C=C1c(cc1)ccc1-[n](c1ccccc11)c2c1[N-]CC=C2 Chemical compound C([C@H](C=C1)[n](c2c(c3c4)nccc2)c3cc2c4-c3ccccc3C22c3ccccc3-c3ccccc23)C=C1c(cc1)ccc1-[n](c1ccccc11)c2c1[N-]CC=C2 LWPQLOMAKPQZLG-BHVANESWSA-N 0.000 description 1
- YUBXXWMJSCDABF-KBZCFIRPSA-N C([C@H]12)C=CC=C1c1ccccc1C21c(cc(c(c2c3[nH]cc2)c2)[n]3-c(cc3)ccc3-c(cc3)ccc3-[n]3c(nccc4)c4c4cc(-c5c(C67c8ccccc8-c8c6cccc8)cccc5)c7cc34)c2-c2ccccc12 Chemical compound C([C@H]12)C=CC=C1c1ccccc1C21c(cc(c(c2c3[nH]cc2)c2)[n]3-c(cc3)ccc3-c(cc3)ccc3-[n]3c(nccc4)c4c4cc(-c5c(C67c8ccccc8-c8c6cccc8)cccc5)c7cc34)c2-c2ccccc12 YUBXXWMJSCDABF-KBZCFIRPSA-N 0.000 description 1
- UOKAERLQSKQGHB-UHFFFAOYSA-N C([CH+]1)C(c2ccccc2)=NC1c(cc1)ccc1-c(cc1)ccc1-[n]1c(ccc(-c2ccccc22)c3C22c4cnccc4-c4ccccc24)c3c2ccccc12 Chemical compound C([CH+]1)C(c2ccccc2)=NC1c(cc1)ccc1-c(cc1)ccc1-[n]1c(ccc(-c2ccccc22)c3C22c4cnccc4-c4ccccc24)c3c2ccccc12 UOKAERLQSKQGHB-UHFFFAOYSA-N 0.000 description 1
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- ZFIQKTXFWZQWDV-UHFFFAOYSA-N n-[4-[2-[4-(n-phenanthren-9-ylanilino)phenyl]ethenyl]phenyl]-n-phenylphenanthren-9-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=CC=C1 ZFIQKTXFWZQWDV-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004225 phenalen-1-yl group Chemical group [H]C1=C([H])C2=C3C(C([H])=C([H])C([H])(*)C3=C([H])C([H])=C2[H])=C1[H] 0.000 description 1
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
- FIZIRKROSLGMPL-UHFFFAOYSA-N phenoxazin-1-one Chemical class C1=CC=C2N=C3C(=O)C=CC=C3OC2=C1 FIZIRKROSLGMPL-UHFFFAOYSA-N 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001732 pyren-2-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C3C([H])=C(*)C([H])=C4C([H])=C([H])C(=C1[H])C2=C34 0.000 description 1
- 125000001486 pyren-4-yl group Chemical group [H]C1=C(C2=C34)C([H])=C([H])C([H])=C2C([*])=C([H])C3=C([H])C([H])=C([H])C4=C1[H] 0.000 description 1
- OWJJRQSAIMYXQJ-UHFFFAOYSA-N pyrene-1,6-diamine Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=C(N)C=CC2=C1 OWJJRQSAIMYXQJ-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000003281 rhenium Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
- 229910000026 rubidium carbonate Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- KJVQYDYPDFFJMP-UHFFFAOYSA-N sulfamethylthiazole Chemical compound CC1=CSC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 KJVQYDYPDFFJMP-UHFFFAOYSA-N 0.000 description 1
- 229950005939 sulfamethylthiazole Drugs 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 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
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 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
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- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
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- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- CWBQQLSTRZUWOM-UHFFFAOYSA-K tris(3-methylphenoxy)alumane Chemical compound [Al+3].CC1=CC=CC([O-])=C1.CC1=CC=CC([O-])=C1.CC1=CC=CC([O-])=C1 CWBQQLSTRZUWOM-UHFFFAOYSA-K 0.000 description 1
- KILCCVQLHISVRW-UHFFFAOYSA-K tris(4-methylphenoxy)alumane Chemical compound [Al+3].CC1=CC=C([O-])C=C1.CC1=CC=C([O-])C=C1.CC1=CC=C([O-])C=C1 KILCCVQLHISVRW-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical class C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
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Images
Abstract
【解決手段】インドール環とフルオレン環とで形成される縮合環を基本骨格として、この縮合環の任意の水素(好ましくはフルオレン構造の9位の水素)をアルキルやアリールなどで置換すると共に、インドール構造のNにアリールを置換させた化合物を発光層用の材料として用いて、有機EL素子を製造する。
【選択図】なし
Description
式(1)において、Ar1はピロール環に縮合しているフルオレン環であり;
インドール環とフルオレン環とで形成される縮合環における任意の部位「−CH=」は部位「−N=」であってもよく、
インドール環とフルオレン環とで形成される縮合環における任意の水素は、炭素数1〜20のアルキル、炭素数3〜20のシクロアルキル、炭素数6〜30のアリール、または炭素数1〜30のヘテロアリールで置換されていてもよく、フルオレン環の9位の2つの水素が置換されている場合、これらの置換基同士は結合してスピロ環を形成していてもよく;
Ar2は炭素数10〜30のアリールであり、ただし炭素数10〜30のアリールの中からビフェニリルが選択される場合には下記式(BP)で表されるビフェニリルであり、
式(BP)において、Ar3は、炭素数6〜30のアリールおよび炭素数1〜30のヘテロアリールから選ばれる少なくとも1つの基で置換されていてもよい炭素数1〜30のヘテロアリールである。
式(1−1)〜(1−6)において、インドール環とフルオレン環とで形成される縮合環における任意の部位「−CH=」は部位「−N=」であってもよく;
R1およびR2は、それぞれ独立して、炭素数6〜18のアリール、または炭素数1〜20のヘテロアリールであり、R1およびR2は互いに結合してスピロ環を形成していてもよく;
Ar2は炭素数10〜30のアリールであり、ただし炭素数10〜30のアリールの中からビフェニリルが選択される場合には下記式(BP)で表されるビフェニリルであり、
式(BP)において、Ar3は、炭素数6〜30のアリールおよび炭素数1〜30のヘテロアリールから選ばれる少なくとも1つの基で置換されていてもよい炭素数1〜30のヘテロアリールである。
Ar2は、ナフチル、フェナントリルまたは下記式(BP)で表されるビフェニリルであり、
式(BP)において、Ar3は、炭素数6〜20のアリールおよび炭素数1〜20のヘテロアリールから選ばれる少なくとも1つの基で置換されていてもよい炭素数1〜20のヘテロアリールである、上記[2]に記載の化合物。
Ar2は、ナフチル、フェナントリルまたは下記式(BP)で表されるビフェニリルであり、
式(BP)において、Ar3は、炭素数6〜10のアリールおよび炭素数1〜10のヘテロアリールから選ばれる少なくとも1つの基で置換されていてもよい、ピリジル、カルバゾリル、インデノカルバゾリル、ピロリル、インドリル、イソインドリル、またはイソオキサゾリルであり、これらの環における任意の部位「−CH=」は部位「−N=」であってもよい、上記[2]または[3]に記載の化合物。
Ar2は、下記式(BP)で表されるビフェニリルであり、
式(BP)において、Ar3は、フェニルで置換されていてもよい、カルバゾリル、カルボリニル、インデノカルバゾリル、インデノカルボリニル、またはベンゾイミダゾリルである、上記[2]〜[4]のいずれかに記載の化合物。
本発明の化合物の具体例は以下に列記する式によって示されるが、本発明はこれらの具体的な構造の開示によって限定されることはない。
より好ましい化合物は式(1−1−274)、式(1−1−307)、式(1−1−334)、式(1−1−364)、式(1−1−393)、式(1−1−422)、式(1−1−452)、式(1−1−482)、式(1−1−511)、式(1−1−540)、式(1−1−569)、式(1−1−598)、(1−1−627)、式(1−1−656)、式(1−1−685)、で表される化合物である。
式(1−1)〜(1−6)で表される化合物は、既知の合成法を利用して製造することができる。例えば、下記の反応1〜5に示す経路に従って合成することができる。また、下記の反応6〜9に示す経路に従って合成することもできる。
反応1では、パラジウム触媒または銅触媒を用いて、塩基および反応促進剤の存在下、3−カルバゾリルハライドまたはトリフラートにAr2の臭化物またはヨウ化物を反応させて、9位をAr2で置換する。ここでAr2は式(1)におけるAr2と同じである。
反応2では、パラジウム触媒を用いて、塩基の存在下、反応1で得られたAr2を有するカルバゾリルハライドまたはトリフラートにビス(ピナコラート)ジボロンを反応させて、Ar2を有するカルバゾリルボロン酸エステル誘導体を合成する。
反応3では、パラジウム触媒を用いて、塩基の存在下、反応2で得られたAr2を有するカルバゾリルボロン酸エステル誘導体にo−ブロモ安息香酸メチルを鈴木カップリング反応させて、Ar2を有するオルト−カルバゾリル安息香酸メチル誘導体を合成する。
反応4では、反応3で得られたAr2を有するオルト−カルバゾリル安息香酸メチル誘導体に2倍モルの有機金属試薬を反応させて、第三アルコール誘導体を合成する。ここでR1およびR2はそれぞれ式(1)におけるR1およびR2と同じであり、R1やR2に応じた有機金属試薬を選択する。
反応5では、酸触媒の存在下、分子内を環化することによって、式(1−1)および(1−2)で表される化合物を製造する。これらの化合物からなる混合物はカラム精製法、再結晶法、または昇華精製法などで分離することができる。
反応6では、パラジウム触媒を用いて、塩基の存在下、2−フルオレンボロン酸に2−ハロゲンニトロベンゼンまたは2−トリフラートニトロベンゼンを鈴木カップリング反応させて、ニトロフェニル基を有するフルオレン誘導体を合成する。ここでR1およびR2はそれぞれ式(1)におけるR1およびR2と同じである。
反応7では、PPh3またはP(OEt)3を用いて、反応6で得られたニトロフェニル基を有するフルオレン誘導体を還元的に環化して、式(1−5’)および(1−6’)で表されるインデンカルバゾール誘導体を合成する。
反応8では、パラジウム触媒または銅触媒を用いて、塩基および反応促進剤の存在下、反応7で得られた式(1−5’)および(1−6’)で表されるインデンカルバゾール誘導体にそれぞれAr2の臭化物またはヨウ化物を反応させて、式(1−5)および(1−6)で表される化合物を製造する。ここでAr2は式(1)におけるAr2と同じである。
反応9では、パラジウム触媒または銅触媒を用いて、塩基および反応促進剤の存在下、反応7で得られた式(1−5’)および(1−6’)で表されるインデンカルバゾール誘導体にそれぞれビフェニルの臭化物またはヨウ化物を反応させて、式(1−5)および(1−6)で表される化合物に含まれる二量化体を製造する。
本発明に係る縮合ピロール多環化合物は、例えば、有機電界発光素子の材料として用いることができる。以下に、本実施形態に係る有機電界発光素子について図面に基づいて詳細に説明する。図1は、本実施形態に係る有機電界発光素子を示す概略断面図である。
図1に示された有機電界発光素子100は、基板101と、基板101上に設けられた陽極102と、陽極102の上に設けられた正孔注入層103と、正孔注入層103の上に設けられた正孔輸送層104と、正孔輸送層104の上に設けられた発光層105と、発光層105の上に設けられた電子輸送層106と、電子輸送層106の上に設けられた電子注入層107と、電子注入層107の上に設けられた陰極108とを有する。
基板101は、有機電界発光素子100の支持体となるものであり、通常、石英、ガラス、金属、プラスチックなどが用いられる。基板101は、目的に応じて板状、フィルム状、またはシート状に形成され、例えば、ガラス板、金属板、金属箔、プラスチックフィルム、プラスチックシートなどが用いられる。なかでも、ガラス板、および、ポリエステル、ポリメタクリレート、ポリカーボネート、ポリスルホンなどの透明な合成樹脂製の板が好ましい。ガラス基板であれば、ソーダライムガラスや無アルカリガラスなどが用いられ、また、厚みも機械的強度を保つのに十分な厚みがあればよいので、例えば、0.2mm以上あればよい。厚さの上限値としては、例えば、2mm以下、好ましくは1mm以下である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、SiO2などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することができる。また、基板101には、ガスバリア性を高めるために、少なくとも片面に緻密なシリコン酸化膜などのガスバリア膜を設けてもよく、特にガスバリア性が低い合成樹脂製の板、フィルムまたはシートを基板101として用いる場合にはガスバリア膜を設けるのが好ましい。
陽極102は、発光層105へ正孔を注入する役割を果たすものである。なお、陽極102と発光層105との間に正孔注入層103および/または正孔輸送層104が設けられている場合には、これらを介して発光層105へ正孔を注入することになる。
正孔注入層103は、陽極102から移動してくる正孔を、効率よく発光層105内または正孔輸送層104内に注入する役割を果たすものである。正孔輸送層104は、陽極102から注入された正孔または陽極102から正孔注入層103を介して注入された正孔を、効率よく発光層105に輸送する役割を果たすものである。正孔注入層103および正孔輸送層104は、それぞれ、正孔注入・輸送材料の一種または二種以上を積層、混合するか、正孔注入・輸送材料と高分子結着剤の混合物により形成される。また、正孔注入・輸送材料に塩化鉄(III)のような無機塩を添加して層を形成してもよい。
発光層105は、電界を与えられた電極間において、陽極102から注入された正孔と、陰極108から注入された電子とを再結合させることにより発光するものである。発光層105を形成する材料としては、正孔と電子との再結合によって励起されて発光する化合物(発光性化合物)であればよく、安定な薄膜形状を形成することができ、かつ、固体状態で強い発光(蛍光および/または燐光)効率を示す化合物であるのが好ましい。
当該式中、Ar1は炭素数6〜30のアリールに由来するm価の基であり、Ar2およびAr3は、それぞれ独立して炭素数6〜30のアリールであるが、Ar1〜Ar3の少なくとも1つはスチルベン構造を有し、Ar1〜Ar3は置換されていてもよく、そして、mは1〜4の整数である。
当該式中、Ar2およびAr3は、それぞれ独立して炭素数6〜30のアリールであり、Ar2およびAr3は置換されていてもよい。
また、特開2003-347056号公報、および特開2001-307884号公報などに記載されたスチルベン構造を有するアミンを用いてもよい。
また、特開平11-97178号公報、特開2000-133457号公報、特開2000-26324号公報、特開2001-267079号公報、特開2001-267078号公報、特開2001-267076号公報、特開2000-34234号公報、特開2001-267075号公報、および特開2001-217077号公報などに記載されたペリレン誘導体を用いてもよい。
また、国際公開第2000/40586号パンフレットなどに記載されたボラン誘導体を用いてもよい。
当該式中、Ar4は炭素数6〜30のアリールに由来するn価の基であり、Ar5およびAr6はそれぞれ独立して炭素数6〜30のアリールであり、Ar4〜Ar6は置換されていてもよく、そして、nは1〜4の整数である。
また、特開2006-156888号公報などに記載された芳香族アミン誘導体を用いてもよい。
また、特開2004-43646号公報、特開2001-76876号公報、および特開平6-298758号公報などに記載されたクマリン誘導体を用いてもよい。
また、特開2005-126399号公報、特開2005-097283号公報、特開2002-234892号公報、特開2001-220577号公報、特開2001-081090号公報、および特開2001-052869号公報などに記載されたピラン誘導体を用いてもよい。
また、特開2006-089398号公報、特開2006-080419号公報、特開2005-298483号公報、特開2005-097263号公報、および特開2004-111379号公報などに記載されたイリジウム錯体を用いてもよい。
また、特開2006-190718号公報、特開2006-128634号公報、特開2006-093542号公報、特開2004-335122号公報、および特開2004-331508号公報などに記載された白金錯体を用いてもよい。
正孔阻止層は、正孔と電子とを発光層内に閉じ込めて、発光効率を向上させる役割を果たすものである。正孔阻止層は、陽極から移動してくる正孔が陰極に到達するのを阻止し、陰極から注入された電子を効率よく発光層の方向に輸送することができる物質であるのが望ましい。すなわち、正孔阻止層を形成する材料には、発光効率を向上させるために、電子移動度が高く、正孔移動度が低いという性質が求められる。加えて、有機電界発光素子の長寿命化の要請から、駆動安定性が高いことも求められている。
電子注入層107は、陰極108から移動してくる電子を、効率よく発光層105内または電子輸送層106内に注入する役割を果たすものである。電子輸送層106は、陰極108から注入された電子または陰極108から電子注入層107を介して注入された電子を、効率よく発光層105に輸送する役割を果たすものである。電子輸送層106および電子注入層107は、それぞれ、電子輸送・注入材料の一種または二種以上を積層、混合するか、電子輸送・注入材料と高分子結着剤の混合物により形成される。
式中、Gは単なる結合手またはn価の連結基を表し、nは2〜8の整数である。また、ピリジン−ピリジンまたはピリジン−Gの結合に用いられない炭素原子は置換されていてもよい。
式中、R1〜R8は水素または置換基であり、隣接する基は互いに結合して縮合環を形成してもよく、Gは単なる結合手またはn価の連結基を表し、nは2〜8の整数である。また、一般式(E−3−2)のGとしては、例えば、ビピリジン誘導体の欄で説明したものと同じものがあげられる。
式中、R11およびR12は、それぞれ独立して、水素原子、アルキル基、置換されていてもよいアリール基、置換シリル基、置換されていてもよい窒素含有複素環基、またはシアノ基の少なくとも一つであり、R13〜R16は、それぞれ独立して、置換されていてもよいアルキル基、または置換されていてもよいアリール基であり、Xは、置換されていてもよいアリーレン基であり、Yは、置換されていてもよい炭素数16以下のアリール基、置換ボリル基、または置換されていてもよいカルバゾール基であり、そして、nはそれぞれ独立して0〜3の整数である。
式中、R11およびR12は、それぞれ独立して、水素原子、アルキル基、置換されていてもよいアリール基、置換シリル基、置換されていてもよい窒素含有複素環基、またはシアノ基の少なくとも一つであり、R13〜R16は、それぞれ独立して、置換されていてもよいアルキル基、または置換されていてもよいアリール基であり、R21およびR22は、それぞれ独立して、それぞれ独立して、水素原子、アルキル基、置換されていてもよいアリール基、置換シリル基、置換されていてもよい窒素含有複素環基、またはシアノ基の少なくとも一つであり、X1は、置換されていてもよい炭素数20以下のアリーレン基であり、nはそれぞれ独立して0〜3の整数であり、そして、mはそれぞれ独立して0〜4の整数である。
各式中、R31〜R34は、それぞれ独立して、メチル、イソプロピルまたはフェニルのいずれかであり、そして、R35およびR36は、それぞれ独立して、水素、メチル、イソプロピルまたはフェニルのいずれかである。
式中、R11およびR12は、それぞれ独立して、水素原子、アルキル基、置換されていてもよいアリール基、置換シリル基、置換されていてもよい窒素含有複素環基、またはシアノ基の少なくとも一つであり、R13〜R16は、それぞれ独立して、置換されていてもよいアルキル基、または置換されていてもよいアリール基であり、X1は、置換されていてもよい炭素数20以下のアリーレン基であり、そして、nはそれぞれ独立して0〜3の整数である。
式中、R31〜R34は、それぞれ独立して、メチル、イソプロピルまたはフェニルのいずれかであり、そして、R35およびR36は、それぞれ独立して、水素、メチル、イソプロピルまたはフェニルのいずれかである。
式中、R11およびR12は、それぞれ独立して、水素原子、アルキル基、置換されていてもよいアリール基、置換シリル基、置換されていてもよい窒素含有複素環基、またはシアノ基の少なくとも一つであり、R13〜R16は、それぞれ独立して、置換されていてもよいアルキル基、または置換されていてもよいアリール基であり、X1は、置換されていてもよい炭素数10以下のアリーレン基であり、Y1は、置換されていてもよい炭素数14以下のアリール基であり、そして、nはそれぞれ独立して0〜3の整数である。
各式中、R31〜R34は、それぞれ独立して、メチル、イソプロピルまたはフェニルのいずれかであり、そして、R35およびR36は、それぞれ独立して、水素、メチル、イソプロピルまたはフェニルのいずれかである。
式中、Ar1〜Ar3はそれぞれ独立に水素または置換されてもよい炭素数6〜30のアリールである。特に、Ar1が置換されてもよいアントリルであるベンゾイミダゾール誘導体が好ましい。
陰極108は、電子注入層107および電子輸送層106を介して、発光層105に電子を注入する役割を果たすものである。
以上の正孔注入層、正孔輸送層、発光層、電子輸送層および電子注入層に用いられる材料は単独で各層を形成することができるが、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ(N−ビニルカルバゾール)、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルフォン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリサルフォン、ポリアミド、エチルセルロース、酢酸ビニル樹脂、ABS樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。
有機電界発光素子を構成する各層は、各層を構成すべき材料を蒸着法、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、印刷法、スピンコート法またはキャスト法、コーティング法などの方法で薄膜とすることにより、形成することができる。このようにして形成された各層の膜厚については特に限定はなく、材料の性質に応じて適宜設定することができるが、通常2nm〜5000nmの範囲である。膜厚は通常、水晶発振式膜厚測定装置などで測定できる。蒸着法を用いて薄膜化する場合、その蒸着条件は、材料の種類、膜の目的とする結晶構造および会合構造などにより異なる。蒸着条件は一般的に、ボート加熱温度+50〜+400℃、真空度10−6〜10−3Pa、蒸着速度0.01〜50nm/秒、基板温度−150〜+300℃、膜厚2nm〜5μmの範囲で適宜設定することが好ましい。
また、本発明は、有機電界発光素子を備えた表示装置または有機電界発光素子を備えた照明装置などにも応用することができる。
有機電界発光素子を備えた表示装置または照明装置は、本実施形態に係る有機電界発光素子と公知の駆動装置とを接続するなど公知の方法によって製造することができ、直流駆動、パルス駆動、交流駆動など公知の駆動方法を適宜用いて駆動することができる。
<式(1−1−28)で表される化合物>
1H−NMR(CDCl3):σ=8.18(d,2H)、7.95〜7.92(m,5H)、7.77〜7.71(m,5H)、7.56〜7.43(m,11H)、7.34〜7.17(m,13H).
<式(1−2−22)で表される化合物>
1H−NMR(CDCl3):σ=8.51(s,1H)、8.23〜8.16(m,3H)、7.92〜7.85(m,5H)、7.70〜7.60(m,4H)、7.51〜7.19(m,23H).
<式(1−1−28)で表される化合物>
ガラス転移温度(Tg):184.8℃
<式(1−2−22)で表される化合物>
ガラス転移温度(Tg):179.6℃
式(1−1−28)、式(1−2−22)で表される化合物および比較例の化合物「CBP」((株)同仁化学研究所製)の物性値をまとめて下記の表1に示した。なお、化合物「CBP」は下記の構造を有する。
また、薄膜蛍光最大波長(λmax)は、日本分光製V−560型分光光度計を用いて励起波長を360nmとして測定した。
さらに、三重項状態エネルギーレベル(T1)は、燐光スペクトルを測定し、スペクトルの立ち上がり位置から算出した。燐光スペクトルの測定は、日立ハイテクノロジーズ社製の蛍光分光光度計F−7000に付属装置の低温測定付属装置を取り付けて行った。測定化合物をエタノールに溶解させたものを試料とし、凍結脱気後、液体窒素温度(77K)で、試料に波長360nmの励起光をチョッパーにてパルス状にあてる(40Hz)ことで発光させ、蛍光成分が消光してからデータを取得し燐光成分のみを取り出した。
つぎに、以下に説明するようにして、実施例1および2に係る有機EL素子を作製し、それぞれ、1000cd/m2発光時の特性である電圧(V)、電流密度(mA/cm2)、発光効率(Lm/W)、電流効率(cd/A)、発光波長(nm)および色度(x,y)の測定を行った。
ITOを150nmの厚さに蒸着した26mm×28mm×0.7mmのガラス基板を透明支持基板とした。この透明支持基板を市販の蒸着装置の基板ホルダーに固定し、HI−1を入れたモリブデン製蒸着用ボート、NPDを入れたモリブデン製蒸着用ボート、式(1−1−28)で表される化合物を入れたモリブデン製蒸着用ボート、Ir(ppy)3を入れたモリブデン製蒸着用ボート、TPBiを入れたモリブデン製蒸着用ボート、フッ化リチウムを入れたモリブデン製蒸着用ボートおよびアルミニウムを入れたタングステン製蒸着用ボートを装着した。
実施例1で緑色燐光ドーパントに用いたIr(ppy)3を蛍光青色ドーパントBD−1に替えた以外は、実施例1に準じた方法で有機EL素子を作製した。ITO電極を陽極、フッ化リチウム/アルミニウム電極を陰極として、1000cd/m2発光時の特性を測定すると、電圧6.95V、電流密度32.5mA/cm2、発光効率1.4Lm/W、電流効率3.1cd/A、発光波長460nmおよび色度(0.140,0.139)であった。
101 基板
102 陽極
103 正孔注入層
104 正孔輸送層
105 発光層
106 電子輸送層
107 電子注入層
108 陰極
Claims (13)
- 下記式(1)で表される化合物。
式(1)において、Ar1はピロール環に縮合しているフルオレン環であり;
インドール環とフルオレン環とで形成される縮合環における任意の部位「−CH=」は部位「−N=」であってもよく、
インドール環とフルオレン環とで形成される縮合環における任意の水素は、炭素数1〜20のアルキル、炭素数3〜20のシクロアルキル、炭素数6〜30のアリール、または炭素数1〜30のヘテロアリールで置換されていてもよく、フルオレン環の9位の2つの水素が置換されている場合、これらの置換基同士は結合してスピロ環を形成していてもよく;
Ar2は炭素数10〜30のアリールであり、ただし炭素数10〜30のアリールの中からビフェニリルが選択される場合には下記式(BP)で表されるビフェニリルであり、
式(BP)において、Ar3は、炭素数6〜30のアリールおよび炭素数1〜30のヘテロアリールから選ばれる少なくとも1つの基で置換されていてもよい炭素数1〜30のヘテロアリールである。 - 下記式(1−1)〜(1−6)のいずれかで表される、請求項1に記載の化合物。
式(1−1)〜(1−6)において、インドール環とフルオレン環とで形成される縮合環における任意の部位「−CH=」は部位「−N=」であってもよく;
R1およびR2は、それぞれ独立して、炭素数6〜18のアリール、または炭素数1〜20のヘテロアリールであり、R1およびR2は互いに結合してスピロ環を形成していてもよく;
Ar2は炭素数10〜30のアリールであり、ただし炭素数10〜30のアリールの中からビフェニリルが選択される場合には下記式(BP)で表されるビフェニリルであり、
式(BP)において、Ar3は、炭素数6〜30のアリールおよび炭素数1〜30のヘテロアリールから選ばれる少なくとも1つの基で置換されていてもよい炭素数1〜30のヘテロアリールである。 - 請求項1〜6のいずれかに記載の化合物を含有する、有機電界発光素子用の発光層用材料。
- さらに、スチルベン構造を有するアミン、ベンゾフルオレン構造を有するアミン、芳香族アミン、クマリン誘導体、ピラン誘導体、イリジウム錯体、レニウム錯体、および白金錯体からなる群から選択される少なくとも1つの化合物を含有する、請求項7に記載の発光層用材料。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置され、請求項7または8に記載の発光層用材料を含有する発光層とを有する、有機電界発光素子。
- さらに、前記陰極と前記発光層との間に配置された電子輸送層および/または電子注入層を有し、該電子輸送層および電子注入層の少なくとも1つは、キノリノール系金属錯体、ピリジン誘導体、フェナントロリン誘導体、ボラン誘導体およびベンゾイミダゾール誘導体からなる群から選択される少なくとも1つを含有する、請求項9に記載の有機電界発光素子。
- 前記電子輸送層および電子注入層の少なくとも1つは、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、請求項10に記載の有機電界発光素子。
- 請求項9〜11のいずれかに記載する有機電界発光素子を備えた表示装置。
- 請求項9〜11のいずれかに記載する有機電界発光素子を備えた照明装置。
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