CN106892915A - Organic compound, organic electroluminescence device and its application - Google Patents
Organic compound, organic electroluminescence device and its application Download PDFInfo
- Publication number
- CN106892915A CN106892915A CN201710101243.8A CN201710101243A CN106892915A CN 106892915 A CN106892915 A CN 106892915A CN 201710101243 A CN201710101243 A CN 201710101243A CN 106892915 A CN106892915 A CN 106892915A
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- Prior art keywords
- bases
- phenanthrene
- cough
- beautiful jade
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 45
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 230000000903 blocking effect Effects 0.000 claims abstract description 12
- -1 pyridine radicals Chemical class 0.000 claims description 312
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 207
- 206010011224 Cough Diseases 0.000 claims description 206
- 239000010977 jade Substances 0.000 claims description 204
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000003386 piperidinyl group Chemical group 0.000 claims description 35
- 230000005540 biological transmission Effects 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- FEKWWZCCJDUWLY-UHFFFAOYSA-N 3-methyl-1h-pyrrole Chemical compound CC=1C=CNC=1 FEKWWZCCJDUWLY-UHFFFAOYSA-N 0.000 claims description 16
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 13
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- TVCXVUHHCUYLGX-UHFFFAOYSA-N 2-Methylpyrrole Chemical compound CC1=CC=CN1 TVCXVUHHCUYLGX-UHFFFAOYSA-N 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 9
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 9
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 8
- 125000005561 phenanthryl group Chemical group 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 150000005048 2,9-phenanthrolines Chemical class 0.000 claims description 4
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- JNBVLGDICHLLTN-DZUOILHNSA-N (2s)-2-acetamido-n-[(2s,3s)-4-[[[(2s)-2-acetamido-3-methylbutanoyl]amino]-(cyclohexylmethyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(C)=O)C(C)C)[C@@H](O)CN(CC1CCCCC1)NC(=O)[C@@H](NC(C)=O)C(C)C)C1=CC=CC=C1 JNBVLGDICHLLTN-DZUOILHNSA-N 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical class C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 69
- 230000005525 hole transport Effects 0.000 abstract description 9
- 239000002019 doping agent Substances 0.000 abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 265
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 164
- 239000010410 layer Substances 0.000 description 128
- 239000002904 solvent Substances 0.000 description 110
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 97
- 238000006243 chemical reaction Methods 0.000 description 97
- 235000019441 ethanol Nutrition 0.000 description 79
- 230000015572 biosynthetic process Effects 0.000 description 61
- 238000003786 synthesis reaction Methods 0.000 description 61
- 238000001953 recrystallisation Methods 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- 238000010792 warming Methods 0.000 description 47
- 239000000243 solution Substances 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 36
- 238000000967 suction filtration Methods 0.000 description 35
- 239000003610 charcoal Substances 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 25
- 238000010521 absorption reaction Methods 0.000 description 21
- 238000007872 degassing Methods 0.000 description 21
- QGZKDVFQNNGYKY-OUBTZVSYSA-N Ammonia-15N Chemical compound [15NH3] QGZKDVFQNNGYKY-OUBTZVSYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 150000004075 acetic anhydrides Chemical class 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 10
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 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 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 9
- 239000012965 benzophenone Substances 0.000 description 9
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical class C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical class BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 8
- 0 CC1(C)c(c(I)*(C=Br)c(CC2)c3C=C2C2=CC=CCC2)c3N(C2CC=CCC2)C2C=CCCC12 Chemical compound CC1(C)c(c(I)*(C=Br)c(CC2)c3C=C2C2=CC=CCC2)c3N(C2CC=CCC2)C2C=CCCC12 0.000 description 8
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000011010 flushing procedure Methods 0.000 description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- PLVCYMZAEQRYHJ-UHFFFAOYSA-N (2-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Br PLVCYMZAEQRYHJ-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 6
- 239000005416 organic matter Substances 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229940125758 compound 15 Drugs 0.000 description 5
- 229940127113 compound 57 Drugs 0.000 description 5
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 4
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- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
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- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 3
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
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- 239000011521 glass Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Chemical class CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 1
- IYWDFZORUJMHRV-UHFFFAOYSA-N n-bromo-n-phenylaniline Chemical compound C=1C=CC=CC=1N(Br)C1=CC=CC=C1 IYWDFZORUJMHRV-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- UWBZUWHVXOFZFZ-UHFFFAOYSA-N pentadecan-2-ylphosphane Chemical class CC(CCCCCCCCCCCCC)P UWBZUWHVXOFZFZ-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/18—Carrier blocking layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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Abstract
The present invention relates to field of light emitting materials, specifically, there is provided a kind of organic compound, organic electroluminescence device and its application.The structural formula of the organic compound is as follows：
Description
Technical field
The present invention relates to field of light emitting materials, in particular to a kind of organic compound, organic electroluminescence device and
Its application.
Background technology
In general, organic light emission phenomenon refers to the phenomenon that luminous energy is converted electrical energy into using organic substance.Using organic
The organic electroluminescence device of luminescence phenomenon, includes generally with anode and negative electrode and wherein the structure of organic matter layer, has
Machine nitride layer is presented the sandwich construction being made up of different material more in order to improve the efficiency and stability of organic electroluminescence device,
Can be for example made up of hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc..In organic electroluminescence
In luminescent device, the material as organic matter layer can be divided into luminescent material and charge transport materials, such as hole according to function
Injection material, hole mobile material, electron transport material, electron injection material etc..
Merely improving above-mentioned organic matter layer cannot make the efficiency of organic electroluminescence device maximize.This is because, working as
Energy level and T1 values, the inherent characteristic of material (mobility, interfacial characteristics etc.) between each organic matter layer etc. form the group for optimizing
During conjunction, it is impossible to while realizing long-life and high efficiency.In addition, the material used in hole transmission layer must have it is relatively low
HOMO values, therefore, major part possesses relatively low T1 values, and thus, the exciton generated in luminescent layer flow to hole transmission layer, ties
Charge unbalance in Tab phenolphthaleinum electroluminescent layer, lights in hole transmission layer or in hole transport bed boundary, produces organic electroluminescence
The phenomenon that the excitation of luminescent device is low, efficiency and life-span decline.
In order to give full play to the excellent characteristic of organic electroluminescence device, the organic matter layer material in device must be stabilization
And efficient material, but do not develop the organic material of stabilization and efficient organic electroluminescence device fully also at present.
In view of this, it is special to propose the present invention.
The content of the invention
The first object of the present invention is to provide a kind of organic compound, and the organic compound can be used as hole transmission layer material
Material or electron-blocking layer material, it is also possible to as hole blocking layer material, electron transport layer materials, material of main part, blue doping
Material and covering layer material, for that can reduce driving voltage in organic electroluminescence device, improve luminous efficiency, brightness, heat
Stability, color purity and device lifetime.
The second object of the present invention is the application for providing a kind of above-mentioned organic compound in luminescent device is prepared, will be upper
State organic compound to be applied in luminescent device, it is possible to increase the luminous efficiency of luminescent device and device lifetime.
The third object of the present invention is to provide a kind of organic electroluminescence device, and the organic electroluminescence device is using upper
Organic compound is stated as hole transport layer material or electron-blocking layer material, or hole blocking layer material, electron transfer layer
Material, material of main part, blue dopant material and covering layer material so that the organic electroluminescence device has high efficiency and longevity
The excellent properties of life.
In order to realize above-mentioned purpose of the invention, spy uses following technical scheme：
In a first aspect, the invention provides a kind of organic compound, the structural formula of the compound is as follows：
Wherein, R1 and R6 are each independently heavy hydrogen, the straight chained alkyl of optionally substituted C1~C20 or branched alkyl, appoint
Choose the phenyl in generation, optionally substituted pyridine radicals, optionally substituted naphthyl, optionally substituted phenanthryl, optionally substituted anthryl, appoint
Choose any one in the phenanthridinyl in generation, optionally substituted xenyl, optionally substituted pyrimidine radicals or optionally substituted triazine radical
Kind or at least two combination；
R2, R3, R4, R5, R7 and R8 are each independently the alkyl of C1~C10 and/or the aryl of C6~C30；
Ar1, Ar2 or Ar3 are each independently hydrogen, heavy hydrogen, halogen, the straight chained alkyl of C1~C20 or branched alkyl or appoint
Choose generation C6~C30 aryl in any one or at least two combination.
As further preferably technical scheme, phenyl, pyridine radicals, naphthyl, phenanthryl, anthryl, phenanthridinyl in R1 or R6,
In xenyl, pyrimidine radicals or triazine radical, more than one hydrogen independently by the straight chained alkyl or branched alkyl of C1~C20, C3~
The cycloalkyl of C24, the alkoxy of C1~C20, halogen, cyano group, trifluoromethyl, trimethyl silicon substrate, naphthyl, anthryl, phenanthryl, benzo
Furyl, dibenzofuran group, fluorenyl, carbazyl, Spirofluorene-based or annular atom number are replaced by 5~20 heteroaryl.
As further preferably technical scheme, the annular atom number be 5~20 heteroaryl be 1- pyrrole radicals, 2- pyrroles
Base, 3- pyrrole radicals, 1- pyridine radicals, 2- pyridine radicals, 3- pyridine radicals, 4- pyridine radicals, 1- indyls, 2- indyls, 3- indyls, 4-
Indyl, 5- indyls, 6- indyls, 7- indyls, 1- isoindolyls, 2- isoindolyls, 3- isoindolyls, 4- iso-indoles
Base, 5- isoindolyls, 6- isoindolyls, 7- isoindolyls, 2- furyls, 3- furyls, 2- benzofuranyls, 3- benzofurans
Base, 4- benzofuranyls, 5- benzofuranyls, 6- benzofuranyls, 7- benzofuranyls, 1- isobenzofuran-bases, the different benzene of 3-
And furyl, 4- isobenzofuran-bases, 5- isobenzofuran-bases, 6- isobenzofuran-bases, 7- isobenzofuran-bases, 2- quinoline
Base, 3- quinolyls, 4- quinolyls, 5- quinolyls, 6- quinolyls, 7- quinolyls, 8- quinolyls, 1- isoquinolyls, 3- isoquinolin
Base, 4- isoquinolyls, 5- isoquinolyls, 6- isoquinolyls, 7- isoquinolyls, 8- isoquinolyls, 2- quinoxalinyls, 5- quinoxalines
Base, 6- quinoxalinyls, 1- coffee piperidinyl, 2- coffee piperidinyl, 3- coffee piperidinyl, 4- coffee piperidinyl, 6- coffee piperidinyl, 7- coffee piperidinyl, 8- coffee piperidinyl,
9- coffee piperidinyl, 10- coffee piperidinyl, 1,7- phenanthrene cough up beautiful jade -2- bases, 1,7- phenanthrene and cough up beautiful jade -3- bases, 1,7- phenanthrene and cough up beautiful jade -4- bases, 1,7- phenanthrene and cough up
Beautiful jade -5- bases, 1,7- phenanthrene cough up beautiful jade -6- bases, 1,7- phenanthrene and cough up beautiful jade -8- bases, 1,7- phenanthrene and cough up beautiful jade -9- bases, 1,7- phenanthrene and cough up beautiful jade -10- bases, 1,8-
Phenanthrene cough up beautiful jade -2- bases, 1,8- phenanthrene cough up beautiful jade -3- bases, 1,8- phenanthrene cough up beautiful jade -4- bases, 1,8- phenanthrene cough up beautiful jade -5- bases, 1,8- phenanthrene cough up beautiful jade -6- bases,
1,8- phenanthrene cough up beautiful jade -7- bases, 1,8- phenanthrene cough up beautiful jade -9- bases, 1,8- phenanthrene cough up beautiful jade -10- bases, 1,9- phenanthrene cough up beautiful jade -2- bases, 1,9- phenanthrene cough up beautiful jade -
3- bases, 1,9- phenanthrene cough up beautiful jade -4- bases, 1,9- phenanthrene and cough up beautiful jade -5- bases, 1,9- phenanthrene and cough up beautiful jade -6- bases, 1,9- phenanthrene and cough up beautiful jade -7- bases, 1,9- phenanthrene and cough up
Beautiful jade -8- bases, 1,9- phenanthrene cough up beautiful jade -10- bases, 1,10- phenanthrene cough up beautiful jade -2- bases, 1,10- phenanthrene cough up beautiful jade -3- bases, 1,10- phenanthrene cough up beautiful jade -4- bases,
1,10- phenanthrene cough up beautiful jade -5- bases, 2,9- phenanthrolines -1- bases, 2,9- phenanthrene cough up beautiful jade -3- bases, 2,9- phenanthrene cough up beautiful jade -4- bases, 2,9- phenanthrene cough up beautiful jade -
5- bases, 2,9- phenanthrene cough up beautiful jade -6- bases, 2,9- phenanthrene and cough up beautiful jade -7- bases, 2,9- phenanthrene and cough up beautiful jade -8- bases, 2,9- phenanthrene to cough up beautiful jade -10- bases, 2,8- luxuriant and rich with fragrance
Cough up beautiful jade -1- bases, 2,8- phenanthrene and cough up beautiful jade -3- bases, 2,8- phenanthrene and cough up beautiful jade -4- bases, 2,8- phenanthrene and cough up beautiful jade -5- bases, 2,8- phenanthrene and cough up beautiful jade -6- bases, 2,
8- phenanthrene coughs up beautiful jade -7- bases, 2,8- phenanthrene and coughs up beautiful jade -9- bases, 2,8- phenanthrene and cough up beautiful jade -10- bases, 2,7- phenanthrene and cough up beautiful jade -1- bases, 2,7- phenanthrene and coughs up beautiful jade -3-
Base, 2,7- phenanthrene cough up beautiful jade -4- bases, 2,7- phenanthrene and cough up beautiful jade -5- bases, 2,7- phenanthrene and cough up beautiful jade -6- bases, 2,7- phenanthrene and cough up beautiful jade -8- bases, 2,7- phenanthrene and cough up
Beautiful jade -9- bases, 2,7- phenanthrene cough up beautiful jade -10- bases, 2- oxazolyls, 4- oxazolyls, 5- oxazolyls, 2- oxadiazolyls, 5- oxadiazolyls, 3-
Furazanyl, 2- thienyls, 3- thienyls, 2- picoline -1- bases, 2- methylpyrrole -3- bases, 2- methylpyrrole -4- bases, 2- first
Base pyrroles -5- bases, 3- methylpyrrole -1- bases, 3- methylpyrrole -2- bases, 3- methylpyrrole -4- bases or 3- methylpyrrole -5- bases.
Used as further preferably technical scheme, R2, R3, R4, R5, R7 and R8 are each independently methyl, ethyl, positive third
Base, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, positive decyl, benzene
Base, 1- naphthyls, 2- naphthyls, 1- anthryls, 2- anthryls, 9- anthryls, 1- phenanthryl, 2- phenanthryl, 3- phenanthryl, 4- phenanthryl, 9- phenanthryl, 1- are simultaneously
Tetraphenyl, 2- aphthacenes base, 9- aphthacenes base, 1- pyrenyls, 2- pyrenyls, 4- pyrenyls, 2- xenyls, 3- xenyls, 4- xenyls,
Para-terpheny -4- bases, para-terpheny -3- bases, para-terpheny -2- bases, meta-terphenyl -4- bases, meta-terphenyl -3- bases, three
Benzene -2- bases, o-tolyl, a tolyl, p-methylphenyl, to tert-butyl-phenyl, p- (2- phenyl propyls) phenyl, 3- methyl -2-
Naphthyl, 4- methyl isophthalic acids-naphthyl, 4- methyl isophthalic acids-anthryl, 4'- methyl biphenyls or the 4 "-tert-butyl group-para-terpheny -4- bases.
Used as further preferably technical scheme, R2 and R3, R4 and R5, R7 and R8 can be combined with each other respectively, form fat
Fat race or aromatic ring.
As further preferably technical scheme, in the aryl of the C6~C30 in Ar1, Ar2 or Ar3, more than one hydrogen
Independently by heavy hydrogen, halogen, the alkyl of C1~C10, the alkenyl of C2~C10, the alkoxy of C1~C10, the aryl of C6~C30 or
The heteroaryl of C5~C30 is replaced.
Used as further preferably technical scheme, the compound is any one in following compounds：
Second aspect, the invention provides a kind of application of organic compound in luminescent device is prepared.
The third aspect, the invention provides a kind of organic electroluminescence device, including anode, hole injection layer, hole biography
Defeated layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, hole transmission layer include that above-mentioned any of which has
The mixture of machine compound or at least two organic compounds.
Present invention also offers the organic electroluminescence device of another structure, including anode, hole injection layer, hole
Transport layer, electron-blocking layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and negative electrode, hole transmission layer and/
Or electron-blocking layer includes the mixture of above-mentioned any of which organic compound or at least two organic compounds.
Compared with prior art, beneficial effects of the present invention are：
The organic compound that the present invention is provided can be as hole transport layer material or electron-blocking layer material, it is also possible to make
It is hole blocking layer material, electron transport layer materials, material of main part, blue dopant material and covering layer material, for Organic Electricity
Driving voltage can be reduced in electroluminescence device, luminous efficiency, brightness, heat endurance, color purity and device lifetime is improved.
The organic compound that the present invention is provided is applied in preparing luminescent device, it is possible to increase the luminous efficiency of luminescent device
And device lifetime.
The organic electroluminescence device that the present invention is provided is using above-mentioned organic compound as hole transport layer material or electricity
Sub- barrier material, or hole blocking layer material, electron transport layer materials, material of main part, blue dopant material and coating
Material so that the organic electroluminescence device has high efficiency and long-life excellent properties.
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and is not construed as limiting the scope of the present invention.It is unreceipted specific in embodiment
Condition person, the condition advised according to normal condition or manufacturer is carried out.
The structural formula of the organic compound that the present invention is provided is as follows：
Wherein, R1 and R6 are each independently heavy hydrogen, the straight chained alkyl of optionally substituted C1~C20 or branched alkyl, appoint
Choose the phenyl in generation, optionally substituted pyridine radicals, optionally substituted naphthyl, optionally substituted phenanthryl, optionally substituted anthryl, appoint
Choose any one in the phenanthridinyl in generation, optionally substituted xenyl, optionally substituted pyrimidine radicals or optionally substituted triazine radical
Kind or at least two combination；
R2, R3, R4, R5, R7 and R8 are each independently the alkyl of C1~C10 and/or the aryl of C6~C30；
Ar1, Ar2 or Ar3 are each independently hydrogen, heavy hydrogen, halogen, the straight chained alkyl of optionally substituted C1~C20 or branch
In the aryl of alkyl group or optionally substituted C6~C30 any one or at least two combination.
It is below the typical but non-limiting optional embodiment of above-claimed cpd：The straight chained alkyl or side chain of C1~C20
Alkyl C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19 or C20's
Straight chained alkyl or branched alkyl；Specifically, what the straight chained alkyl or branched alkyl of C1~C20 were typical but non-limiting is following alkane
Any one in base：Methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, n-pentyl, 2- first
Base butyl, 3- methyl butyls, 1- methyl butyls, 2,2- dimethyl propyls, 1,2- dimethyl propyls, 1,1- dimethyl propyls, 1-
Ethyl propyl, n-hexyl, 4- methyl amyls, 3- methyl amyls, 2- methyl amyls, 1- methyl amyls, 2,3- dimethylbutyls, 1,
3- dimethylbutyls, 3,3- dimethylbutyls, 2,2- dimethylbutyls, 1,1- dimethylbutyls, 2- ethyl-butyls, 1- ethyl fourths
Base, 1- Ethyl-2-Methyls propyl group, 1,1,2- thmethylpropyls, 1,2,2- thmethylpropyls, 1- methyl isophthalic acids-ethyl propyl, positive heptan
Base, 1- methylhexyls, 2- methylhexyls, 3- methylhexyls, 1,2- methyl amyls, 1,3- dimethyl amyl groups, 1,4- dimethyl-pentens
Base, 2,3- dimethyl amyl groups, 2,4- dimethyl amyl groups, 1,1- dimethyl amyl groups, 2,2- dimethyl amyl groups, 3,3- dimethyl-pentens
Base, 3,4- dimethyl amyl groups, 1- ethyl pentyl groups, 2- ethyl pentyl groups, 3- ethyl pentyl groups, 1,2,3- trimethyl butyls, 1,1,2- tri-
Methyl butyl, 1,1,3- trimethyl butyls, 1- ethyl 2- methyl butyls, 1- ethyl -3- methyl butyls, 2,2,3- trimethyl fourths
Base, 2- ethyl -3- methyl butyls, 1,2- diethylpropyls, 1,1,2,2- tetramethyls propyl group, n-octyl, 1- methylheptyls, 2- first
Base heptyl, 3- methylheptyls, 4- methylheptyls, 1,1- dimethylhexanyls, 1,2- dimethylhexanyls, 1,3- dimethylhexanyls, 1,
4- dimethylhexanyls, 1,5- dimethylhexanyls, 1- ethylhexyls, 2- ethylhexyls, 3- ethylhexyls, 1,2,3- trimethyls penta
Base, 1,2,4- tri-methyl-amyls, 2,3,4- tri-methyl-amyls, 1,1,2- tri-methyl-amyls, 1,1,3- tri-methyl-amyls, 2,2,3-
Tri-methyl-amyl, 1- Ethyl-2-Methyls amyl group, 1- ethyl -3- methyl amyls, 2- ethyl -3- methyl amyls, 1,1,2,2- tetramethyls
Base butyl, 1,2- diethyl butyl, 1- ethyl -2,2- dimethylbutyls, 1,1- dimethyl -2- ethyl-butyls, 1- propyl group -2- first
Base butyl, n-nonyl, 1- Methyl Octyls, 2- Methyl Octyls, 3- Methyl Octyls, 4- Methyl Octyls, 5- Methyl Octyls, 1,1- diformazans
Base heptyl, 1,2- dimethyl heptyl, 1,3- dimethyl heptyl, 1,4- dimethyl heptyl, 1- ethylheptyls, 2- ethylheptyls, 3-
Ethylheptyl, 4- ethylheptyls, 1,1,2- trimethyls, 1,1,3- trimethyls, 2,2,3- trimethyls, 1,2,3-
Trimethyl, 1- Ethyl-2-Methyls hexyl, 1- ethyl -3- methylhexyls, 1- propyl group hexyl, 2- propyl group hexyl, 3- propyl group oneself
Base, 1- isopropyls hexyl, 2- isopropyls hexyl, 3- isopropyls hexyl, 1,1,2,2- tetramethyls amyl group, 1,1,3,3- tetramethyls penta
Base, 1,2,2,3- tetramethyls amyl group, 1,2,3,3- tetramethyls amyl group, 1- ethyl -2,2- dimethyl amyl groups, 1- ethyls -2,3- two
Methyl amyl, 1,2- dimethyl -1- ethyl pentyl groups, 1- propyl group -2- methyl amyls, 1,1,2,2,3- trimethyl butyls, 3- methyl -
1,2- diethyl butyl, positive decyl, 1- Nonyls, 2- Nonyls, 3- Nonyls, 4- Nonyls, 5- Nonyls,
1,1- dimethyl octyl group, 1,3- dimethyl octyl group, 1,4- dimethyl octyl group, 1,5- dimethyl octyl group, 2,2- dimethyl octyl group, 2,
3- dimethyl octyl group, 2,4- dimethyl octyl group, 2,5- dimethyl octyl group, 3,3- dimethyl octyl group, 3,4- dimethyl octyl group, 3,5-
Dimethyl octyl group, 4,4- dimethyl octyl group, 4,5- dimethyl octyl group, 1- ethyloctanyls, 2- ethyloctanyls, 3- ethyloctanyls, 4-
Ethyloctanyl, 1,1,2- trimethyls heptyl, 1,1,3- trimethyls heptyl, 1,1,4- trimethyls heptyl, 1- Ethyl-2-Methyls heptan
Base, 1- methyl -2- ethylheptyls, 1- propylheptyls, 2- propylheptyls, 3- propylheptyls, 1- isopropyls heptyl, 2- isopropyls heptan
Base, 3- isopropyls heptyl, 1,1,2,2- tetramethylhexyls, 1,1,3,3- tetramethylhexyls, 1,2,2,3- tetramethylhexyls, 1,2,
3,3- tetramethylhexyls, 1- ethyl -2,2- dimethylhexanyls, 1- ethyl -2,3- dimethylhexanyls, 1,2- dimethyl -1- ethyls
Hexyl, 1- propyl group -2- methylhexyls, n-undecane base, 1- methyldecyls, 2- methyldecyls, 3- methyldecyls, the 4- methyl last of the ten Heavenly stems
Base, 5- methyldecyls, 1,1- dimethyl nonyl, 1,2- dimethyl nonyl, 1,3- dimethyl nonyl, 1,4- dimethyl nonyl, 1,
5- dimethyl nonyl, 2,2- dimethyl nonyl, 2,3- dimethyl nonyl, 2,4- dimethyl nonyl, 2,5- dimethyl nonyl, 3,3-
Dimethyl nonyl, 3,4- dimethyl nonyl, 3,5- dimethyl nonyl, 1- ethylnonanyls, 2- ethylnonanyls, 3- ethylnonanyls, 4-
Ethylnonanyl, 5- ethylnonanyls, 1,1,2- trimethyloctyls, 1,1,3- trimethyloctyls, 1,1,4- trimethyloctyls, 1,1,5-
Trimethyloctyl, 1- methyl isophthalic acids-ethyloctanyl, 1- methyl -2- ethyloctanyls, 1- methyl -3- ethyloctanyls, 1- methyl -4- second
Base octyl group, 2- methyl -2- ethyloctanyls, 2- methyl -3- ethyloctanyls, 3- methyl -4- ethyloctanyls, 1- propyl octyls, 2- third
Base octyl group, 3- propyl octyls, 4- propyl octyls, 1- isopropyls octyl group, 2- isopropyls octyl group, 3- isopropyls octyl group, 4- isopropyls
Octyl group, 1,1,2,2- tetramethyls heptyl, 1,1,3,3- tetramethyls heptyl, 1,2,2,3- tetramethyls heptyl, 1,2,3,3- tetramethyls
Heptyl, 1- ethyl -2,2- dimethyl heptyl, 1- ethyl -2,3- dimethyl heptyl, 1,2- dimethyl -1- ethylheptyls, 1- third
Base -2- methylheptyls, dodecyl, 1- methylundecyls, 2- methylundecyls, 3- methylundecyls, 4- methyl
Undecyl, 5- methylundecyls, 6- methylundecyls, 1,1- dimethyl decyls, 1,2- dimethyl decyls, 1,3- diformazans
Base decyl, 1,4- dimethyl decyls, 1,5- dimethyl decyls, 1,6- dimethyl decyls, 2,2- dimethyl decyls, 2,3- dimethyl
Decyl, 2,4- dimethyl decyls, 2,5- dimethyl decyls, 3,3- dimethyl decyls, 3,4- dimethyl decyls, the 3,5- dimethyl last of the ten Heavenly stems
Base, 1- ethyls decyl, 2- ethyls decyl, 3- ethyls decyl, 4- ethyls decyl, 5- ethyls decyl, 1,1,2- trimethyls nonyl, 1,
1,3- trimethyls nonyl, 1,1,4- trimethyls nonyl, 1,1,5- trimethyls nonyl, 1- methyl isophthalic acids-ethylnonanyl, 1- methyl -2-
Ethylnonanyl, 1- methyl -3- ethylnonanyls, 1- methyl -4- ethylnonanyls, 2- methyl -2- ethylnonanyls, 2- methyl -3- ethyls
Nonyl, 3- methyl -4- ethylnonanyls, 1- propyl group nonyl, 2- propyl group nonyl, 3- propyl group nonyl, 4- propyl group nonyl, 1- isopropyl nonyls
Base, 2- isopropyls nonyl, 3- isopropyls nonyl, 4- isopropyls nonyl, 1,1,2,2- tetramethyls octyl group, 1,1,3,3- tetramethyls are pungent
Base, 1,2,2,3- tetramethyls octyl group, 1,2,3,3- tetramethyls octyl group, 1- ethyl -2,2- dimethyl octyl group, 1- ethyls -2,3- two
Methyl Octyl, 1,2- dimethyl -1- ethyloctanyls, 1- propyl group -2- Methyl Octyls, n-tridecane base, 1- methyl dodecyl, 2-
Methyl dodecyl, 3- methyl dodecyl, 4- methyl dodecyl, 5- methyl dodecyl, 6- methyl dodecyl, 1,1-
Dimethyl undecyl, 1,2- dimethyl undecyl, 1,3- dimethyl undecyl, 1,4- dimethyl undecyl, 1,5-
Dimethyl undecyl, 1,6- dimethyl undecyl, 2,2- dimethyl undecyl, 2,3- dimethyl undecyl, 2,4-
Dimethyl undecyl, 2,5- dimethyl undecyl, 2,6- dimethyl undecyl, 3,3- dimethyl undecyl, 3,4-
Dimethyl undecyl, 3,5- dimethyl undecyl, 1- ethyls undecyl, 2- ethyls undecyl, 3- ethyl hendecanes
Base, 4- ethyls undecyl, 5- ethyls undecyl, 1,1,2- trimethyldecylammoniums, 1,1,3- trimethyldecylammoniums, 1,1,4- front threes
Base decyl, 1,1,5- trimethyldecylammoniums, 1- methyl isophthalic acids-ethyl decyl, 1- methyl -2- ethyls decyl, the 1- methyl -3- ethyl last of the ten Heavenly stems
Base, 1- methyl -4- ethyls decyl, 2- methyl -2- ethyls decyl, 2- methyl -3- ethyls decyl, 3- methyl -4- ethyls decyl, 1-
Propyl group decyl, 2- propyl group decyl, 3- propyl group decyl, 4- propyl group decyl, 1- isopropyls decyl, 2- isopropyls decyl, 3- isopropyls
Decyl, 4- isopropyls decyl, 1,1,2,2- tetramethyls nonyl, 1,1,3,3- tetramethyls nonyl, 1,2,2,3- tetramethyls nonyl, 1,
2,3,3- tetramethyls nonyl, 1- ethyl -2,2- dimethyl nonyl, 1- ethyl -2,3- dimethyl nonyl, 1,2- dimethyl -1- second
Base nonyl, 1- propyl group -2- Nonyls, n-tetradecane base, 1- methyltridecs base, 2- methyltridecs base, 3- methyl 13
Alkyl, 4- methyltridecs base, 5- methyltridecs base, 6- methyltridecs base, 7-- methyltridecs base, 1,1- dimethyl
Dodecyl, 1,2- dimethyl dodecyls base, 1,3- dimethyl dodecyls base, 1,4- dimethyl dodecyls base, 1,5- dimethyl
Dodecyl, 1,6- dimethyl dodecyls base, 1,7- dimethyl dodecyls base, 2,2- dimethyl dodecyls base, 2,3- dimethyl
Dodecyl, 2,4- dimethyl dodecyls base, 2,5- dimethyl dodecyls base, 2,6- dimethyl dodecyls base, 2,7- dimethyl
Dodecyl, 3,3- dimethyl dodecyls base, 3,4- dimethyl dodecyls base, 3,5- dimethyl dodecyls base, 3,6- dimethyl
Dodecyl, 3,7- dimethyl dodecyls base, 1- ethyls dodecyl, 2- ethyls dodecyl, 3- ethyls dodecyl, 4- second
Base dodecyl, 5- ethyls dodecyl, 6- ethyls dodecyl, 1,1,2- norfarnesanes base, 1,1,3- trimethyls ten
One alkyl, 1,1,4- norfarnesanes base, 1,1,5- norfarnesanes base, 1,1,6- norfarnesanes base, 1- methyl-
1- ethyls undecyl, 1- methyl -2- ethyls undecyl, 1- methyl -3- ethyls undecyl, 1- methyl -4- ethyls 11
Alkyl, 2- methyl -2- ethyls undecyl, 2- methyl -3- ethyls undecyl, 3- methyl -4- ethyls undecyl, 1- propyl group
Undecyl, 2- propyl group undecyl, 3- propyl group undecyl, 4- propyl group undecyl, 1- isopropyls undecyl, 2- isopropyls
Base undecyl, 3- isopropyls undecyl, 4- isopropyls undecyl, 1,1,2,2- tetramethyls decyl, 1,1,3,3- tetramethyls
Base decyl, 1,2,2,3- tetramethyls decyl, 1,2,3,3- tetramethyls decyl, 1- ethyl -2,2- dimethyl decyls, 1- ethyl -2,
3- dimethyl decyls, 1,2- dimethyl -1- ethyls decyl, 1- propyl group -2- methyldecyls, n-pentadecane base, 1- methyltetradecylphosphines
Base, 2- methyltetradecylphosphines base, 3- methyltetradecylphosphines base, 4- methyltetradecylphosphines base, 5- methyltetradecylphosphines base, 6- methyltetradecylphosphines
Base, 7- methyltetradecylphosphines base, 1,1- dimethyltridecanes base, 1,2- dimethyltridecanes base, 1,3- dimethyltridecanes base, 1,
4- dimethyltridecanes base, 1,5- dimethyltridecanes base, 1,6- dimethyltridecanes base, 1,7- dimethyltridecanes base, 2,
2- dimethyltridecanes base, 2,3- dimethyltridecanes base, 2,4- dimethyltridecanes base, 2,5- dimethyltridecanes base, 2,
6- dimethyltridecanes base, 2,7- dimethyltridecanes base, 3,3- dimethyltridecanes base, 3,4- dimethyltridecanes base, 3,
5- dimethyltridecanes base, 3,6- dimethyltridecanes base, 3,7- dimethyltridecanes base, 1- ethyls tridecyl, 2- ethyls
Tridecyl, 3- ethyls tridecyl, 4- ethyls tridecyl, 5- ethyls tridecyl, 6- ethyls tridecyl, 1,1,2- tri-
Methyl dodecyl, 1,1,3- trimethyldodecanes base, 1,1,4- trimethyldodecanes base, 1,1,5- trimethyldodecanes base,
1,1,6- trimethyldodecanes base, 1- methyl isophthalic acids-ethyl dodecyl, 1- methyl -2- ethyls dodecyl, 1- methyl -3- second
Base dodecyl, 1- methyl -4- ethyls dodecyl, 2- methyl -2- ethyls dodecyl, 2- methyl -3- ethyls dodecyl,
3- methyl -4- ethyls dodecyl, 1- propyl group dodecyl, 2- propyl group dodecyl, 3- propyl group dodecyl, 4- propyl group 12
Alkyl, 1- isopropyls dodecyl, 2- isopropyls dodecyl, 3- isopropyls dodecyl, 4- isopropyls dodecyl, 1,1,
2,2- tetramethyls undecyl, 1,1,3,3- tetramethyls undecyl, 1,2,2,3- tetramethyls undecyl, 1,2,3,3- tetramethyls
Base undecyl, 1- ethyl -2,2- dimethyl undecyl, 1- ethyl -2,3- dimethyl undecyl, 1,2- dimethyl -1-
Ethyl undecyl, 1- propyl group -2- methylundecyls, n-hexadecyl, 1- methyl pentadecyl, 2- methyl pentadecyl,
3- methyl pentadecyl, 4- methyl pentadecyl, 5- methyl pentadecyl, 6- methyl pentadecyl, 7- methyl pentadecyl, 8-
Methyl pentadecyl, 1,1- dimethyl tetradecyls base, 1,2- dimethyl tetradecyls base, 1,3- dimethyl tetradecyls base, 1,4- bis-
Methyltetradecylphosphine base, 1,5- dimethyl tetradecyls base, 1,6- dimethyl tetradecyls base, 1,7- dimethyl tetradecyls base, 1,8- bis-
Methyltetradecylphosphine base, 2,2- dimethyl tetradecyls base, 2,3- dimethyl tetradecyls base, 2,4- dimethyl tetradecyls base, 2,5- bis-
Methyltetradecylphosphine base, 2,6- dimethyl tetradecyls base, 2,7- dimethyl tetradecyls base, 3,3- dimethyl tetradecyls base, 3,4- bis-
Methyltetradecylphosphine base, 3,5- dimethyl tetradecyls base, 3,6- dimethyl tetradecyls base, 3,7- dimethyl tetradecyls base, 1- ethyls
Myristyl, 2- ethyls myristyl, 3- ethyls myristyl, 4- ethyls myristyl, 5- ethyls myristyl, 6- ethyls ten
Tetraalkyl, 1,1,2- trimethyltridecvls, 1,1,3- trimethyltridecvls, 1,1,4- trimethyltridecvls, 1,1,5-
Trimethyltridecvl, 1,1,6- trimethyltridecvls, 1- methyl isophthalic acids-ethyl tridecyl, 1- methyl -2- ethyl tridecanes
Base, 1- methyl -3- ethyls tridecyl, 1- methyl -4- ethyls tridecyl, 2- methyl -2- ethyls tridecyl, 2- methyl -
3- ethyls tridecyl, 3- methyl -4- ethyls tridecyl, 1- propyl group tridecyl, 2- propyl group tridecyl, 3- propyl group 13
Alkyl, 4- propyl group tridecyl, 1- isopropyls tridecyl, 2- isopropyls tridecyl, 3- isopropyls tridecyl, 4- isopropyls
Base tridecyl, 1,1,2,2- tetramethyls dodecyl, 1,1,3,3- tetramethyls dodecyl, 1,2,2,3- tetramethyl dodecanes
Base, 1,2,3,3- tetramethyls dodecyl, 1- ethyl -2,2- dimethyl dodecyls base, 1- ethyl -2,3- dimethyl dodecyls
Base, 1,2- dimethyl -1- ethyls dodecyl, 1- propyl group -2- methyl dodecyl, n-heptadecane base, 1- methyl cetyl,
2- methyl cetyl, 3- methyl cetyl, 4- methyl cetyl, 5- methyl cetyl, 6- methyl cetyl, 7-
Methyl cetyl, 8- methyl cetyl, 1,1- dimethyl pentadecyl, 1,2- dimethyl pentadecyl, 1,3- dimethyl
Pentadecyl, 1,4- dimethyl pentadecyl, 1,5- dimethyl pentadecyl, 1,6- dimethyl pentadecyl, 1,7- dimethyl
Pentadecyl, 1,8- dimethyl pentadecyl, 2,2- dimethyl pentadecyl, 2,3- dimethyl pentadecyl, 2,4- dimethyl
Pentadecyl, 2,5- dimethyl pentadecyl, 2,6- dimethyl pentadecyl, 2,7- dimethyl pentadecyl, 3,3- dimethyl
Pentadecyl, 3,4- dimethyl pentadecyl, 3,5- dimethyl pentadecyl, 3,6- dimethyl pentadecyl, 3,7- dimethyl
Pentadecyl, 1- ethyls pentadecyl, 2- ethyls pentadecyl, 3- ethyls pentadecyl, 4- ethyls pentadecyl, 5- ethyls ten
Five alkyl, 6- ethyls pentadecyl, 1,1,2- trimethyl tetradecyls base, 1,1,3- trimethyl tetradecyls base, 1,1,4- trimethyls
Myristyl, 1,1,5- trimethyl tetradecyls base, 1,1,6- trimethyl tetradecyls base, 1- methyl isophthalic acids-ethyl myristyl, 1- first
Base -2- ethyls myristyl, 1- methyl -3- ethyls myristyl, 1- methyl -4- ethyls myristyl, 2- methyl -2- ethyls ten
Tetraalkyl, 2- methyl -3- ethyls myristyl, 3- methyl -4- ethyls myristyl, 1- propyl group myristyl, 2- propyl group 14
Alkyl, 3- propyl group myristyl, 4- propyl group myristyl, 1- isopropyls myristyl, 2- isopropyls myristyl, 3- isopropyls
Myristyl, 4- isopropyls myristyl, 1,1,2,2- tetramethyls tridecyl, 1,1,3,3- tetramethyls tridecyl, 1,2,
2,3- tetramethyls tridecyl, 1,2,3,3- tetramethyls tridecyl, 1- ethyl -2,2- dimethyltridecanes base, 1- ethyl -2,
3- dimethyltridecanes base, 1,2- dimethyl -1- ethyls tridecyl, 1- propyl group -2- methyltridecs base, n-octadecane base,
1- methyl heptadecyl, 2- methyl heptadecyl, 3- methyl heptadecyl, 4- methyl heptadecyl, 5- methyl heptadecyl, 6-
Methyl heptadecyl, 7- methyl heptadecyl, 8- methyl heptadecyl, 9- methyl heptadecyl, 1,1- dimethyl hexadecyls base,
1,2- dimethyl hexadecyls base, 1,3- dimethyl hexadecyls base, 1,4- dimethyl hexadecyls base, 1,5- dimethyl hexadecyls base,
1,6- dimethyl hexadecyls base, 1,7- dimethyl hexadecyls base, 1,8- dimethyl hexadecyls base, 2,2- dimethyl hexadecyls base,
2,3- dimethyl hexadecyls base, 2,4- dimethyl hexadecyls base, 2,5- dimethyl hexadecyls base, 2,6- dimethyl hexadecyls base,
2,7- dimethyl hexadecyls base, 3,3- dimethyl hexadecyls base, 3,4- dimethyl hexadecyls base, 3,5- dimethyl hexadecyls base,
3,6- dimethyl hexadecyls base, 3,7- dimethyl hexadecyls base, 1- ethylhexadecyls, 2- ethylhexadecyls, 3- ethyls ten
Six alkyl, 4- ethylhexadecyls, 5- ethylhexadecyls, 6- ethylhexadecyls, 1,1,2- trimethylpentadecanes base, 1,1,
3- trimethylpentadecanes base, 1,1,4- trimethylpentadecanes base, 1,1,5- trimethylpentadecanes base, 1,1,6- trimethylpentadecanes
Base, 1- methyl isophthalic acids-ethyl pentadecyl, 1- methyl -2- ethyls pentadecyl, 1- methyl -3- ethyls pentadecyl, 1- methyl -
4- ethyls pentadecyl, 2- methyl -2- ethyls pentadecyl, 2- methyl -3- ethyls pentadecyl, 3- methyl -4- ethyls 15
Alkyl, 1- propyl group pentadecyl, 2- propyl group pentadecyl, 3- propyl group pentadecyl, 4- propyl group pentadecyl, 1- isopropyls 15
Alkyl, 2- isopropyls pentadecyl, 3- isopropyls pentadecyl, 4- isopropyls pentadecyl, the 1,1,2,2- tetramethyl tetradecanes
Base, 1,1,3,3- tetramethyls myristyl, 1,2,2,3- tetramethyls myristyl, 1,2,3,3- tetramethyls myristyl, 1- second
Base -2,2- dimethyl tetradecyls base, 1- ethyl -2,3- dimethyl tetradecyls base, 1,2- dimethyl -1- ethyls myristyl, 1-
Propyl group -2- methyltetradecylphosphines base, NSC 77136 base, 1- methyl octadecyl, 2- methyl octadecyl, 3- methyl octadecyl,
4- methyl octadecyl, 5- methyl octadecyl, 6- methyl octadecyl, 7- methyl octadecyl, 8- methyl octadecyl, 9-
Methyl octadecyl, 1,1- dimethyl heptadecyl, 1,2- dimethyl heptadecyl, 1,3- dimethyl heptadecyl, 1,4- bis-
Methyl heptadecyl, 1,5- dimethyl heptadecyl, 1,6- dimethyl heptadecyl, 1,7- dimethyl heptadecyl, 1,8- bis-
Methyl heptadecyl, 2,2- dimethyl heptadecyl, 2,3- dimethyl heptadecyl, 2,4- dimethyl heptadecyl, 2,5- bis-
Methyl heptadecyl, 2,6- dimethyl heptadecyl, 2,7- dimethyl heptadecyl, 3,3- dimethyl heptadecyl, 3,4- bis-
Methyl heptadecyl, 3,5- dimethyl heptadecyl, 3,6- dimethyl heptadecyl, 3,7- dimethyl heptadecyl, 1- ethyls
Heptadecyl, 2- ethyls heptadecyl, 3- ethyls heptadecyl, 4- ethyls heptadecyl, 5- ethyls heptadecyl, 6- ethyls ten
Seven alkyl, 1,1,2- trimethyls cetyl, 1,1,3- trimethyls cetyl, 1,1,4- trimethyls cetyl, 1,1,5-
Trimethyl cetyl, 1,1,6- trimethyls cetyl, 1- methyl isophthalic acids-ethylhexadecyl, 1- methyl -2- ethyl hexadecanes
Base, 1- methyl -3- ethylhexadecyls, 1- methyl -4- ethylhexadecyls, 2- methyl -2- ethylhexadecyls, 2- methyl -
3- ethylhexadecyls, 3- methyl -4- ethylhexadecyls, 1- propyl group cetyl, 2- propyl group cetyl, 3- propyl group 16
Alkyl, 4- propyl group cetyl, 1- isopropyls cetyl, 2- isopropyls cetyl, 3- isopropyls cetyl, 4- isopropyls
Base cetyl, 1,1,2,2- tetramethyl-pentadecanes base, 1,1,3,3- tetramethyl-pentadecanes base, 1,2,2,3- tetramethyl-pentadecanes
Base, 1,2,3,3- tetramethyl-pentadecanes base, 1- ethyl -2,2- dimethyl pentadecyl, 1- ethyl -2,3- dimethyl pentadecanes
Base, 1,2- dimethyl -1- ethyls pentadecyl, 1- propyl group -2- methyl pentadecyl, n-eicosane base, 1- methyl nonadecyl,
2- methyl nonadecyl, 3- methyl nonadecyl, 4- methyl nonadecyl, 5- methyl nonadecyl, 6- methyl nonadecyl, 7-
Methyl nonadecyl, 8- methyl nonadecyl, 9- methyl nonadecyl, 10- methyl nonadecyl, 1,1- dimethyloctadecylammoniums
Base, 1,2- dimethyl stearyls, 1,3- dimethyl stearyls, 1,4- dimethyl stearyls, 1,5- dimethyloctadecylammoniums
Base, 1,6- dimethyl stearyls, 1,7- dimethyl stearyls, 1,8- dimethyl stearyls, 1,9- dimethyloctadecylammoniums
Base, 2,2- dimethyl stearyls, 2,3- dimethyl stearyls, 2,4- dimethyl stearyls, 2,5- dimethyloctadecylammoniums
Base, 2,6- dimethyl stearyls, 2,7- dimethyl stearyls, 2,8- dimethyl stearyls, 2,9- dimethyloctadecylammoniums
Base, 3,3- dimethyl stearyls, 3,4- dimethyl stearyls, 3,5- dimethyl stearyls, 3,6- dimethyloctadecylammoniums
Base, 3,7- dimethyl stearyls, 1- ethyls octadecyl, 2- ethyls octadecyl, 3- ethyls octadecyl, 4- ethyls 18
Alkyl, 5- ethyls octadecyl, 6- ethyls octadecyl, 1,1,2- trimethyls heptadecyl, 1,1,3- trimethyls heptadecyl,
1,1,4- trimethyls heptadecyl, 1,1,5- trimethyls heptadecyl, 1,1,6- trimethyls heptadecyl, 1- methyl isophthalic acids-ethyl
Heptadecyl, 1- methyl -2- ethyls heptadecyl, 1- methyl -3- ethyls heptadecyl, 1- methyl -4- ethyls heptadecyl, 2-
Methyl -2- ethyls heptadecyl, 2- methyl -3- ethyls heptadecyl, 3- methyl -4- ethyls heptadecyl, 1- propyl group heptadecanes
Base, 2- propyl group heptadecyl, 3- propyl group heptadecyl, 4- propyl group heptadecyl, 1- isopropyls heptadecyl, 2- isopropyls 17
Alkyl, 3- isopropyls heptadecyl, 4- isopropyls heptadecyl, 1,1,2,2- tetramethyls cetyl, 1,1,3,3- tetramethyls
Cetyl, 1,2,2,3- tetramethyls cetyl, 1,2,3,3- tetramethyls cetyl, 1- ethyl -2,2- dimethyl 16
Alkyl, 1- ethyl -2,3- dimethyl hexadecyls base, 1,2- dimethyl -1- ethylhexadecyls or 1- propyl group -2- methyl hexadecanes
Base；
The alkyl of C1~C10 is methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, positive penta
Base, 2- methyl butyls, 3- methyl butyls, 1- methyl butyls, 2,2- dimethyl propyls, 1,2- dimethyl propyls, 1,1- dimethyl
Propyl group, 1- ethyl propyls, n-hexyl, 4- methyl amyls, 3- methyl amyls, 2- methyl amyls, 1- methyl amyls, 2,3- dimethyl
Butyl, 1,3- dimethylbutyls, 3,3- dimethylbutyls, 2,2- dimethylbutyls, 1,1- dimethylbutyls, 2- ethyl-butyls,
1- ethyl-butyls, 1- Ethyl-2-Methyls propyl group, 1,1,2- thmethylpropyls, 1,2,2- thmethylpropyls, 1- methyl isophthalic acids-ethyl
Propyl group, n-heptyl, 1- methylhexyls, 2- methylhexyls, 3- methylhexyls, 1,2- methyl amyls, 1,3- dimethyl amyl groups, 1,4-
Dimethyl amyl group, 2,3- dimethyl amyl groups, 2,4- dimethyl amyl groups, 1,1- dimethyl amyl groups, 2,2- dimethyl amyl groups, 3,3- bis-
Methyl amyl, 3,4- dimethyl amyl groups, 1- ethyl pentyl groups, 2- ethyl pentyl groups, 3- ethyl pentyl groups, 1,2,3- trimethyl butyls, 1,
1,2- trimethyl butyls, 1,1,3- trimethyl butyls, 1- ethyl 2- methyl butyls, 1- ethyl -3- methyl butyls, 2,2,3- front threes
Base butyl, 2- ethyl -3- methyl butyls, 1,2- diethylpropyls, 1,1,2,2- tetramethyls propyl group, n-octyl, 1- methylheptyls,
2- methylheptyls, 3- methylheptyls, 4- methylheptyls, 1,1- dimethylhexanyls, 1,2- dimethylhexanyls, 1,3- dimethyl oneself
Base, 1,4- dimethylhexanyls, 1,5- dimethylhexanyls, 1- ethylhexyls, 2- ethylhexyls, 3- ethylhexyls, 1,2,3- front threes
Base amyl group, 1,2,4- tri-methyl-amyls, 2,3,4- tri-methyl-amyls, 1,1,2- tri-methyl-amyls, 1,1,3- tri-methyl-amyls, 2,
2,3- tri-methyl-amyls, 1- Ethyl-2-Methyls amyl group, 1- ethyl -3- methyl amyls, 2- ethyl -3- methyl amyls, 1,1,2,2-
Tetramethyl butyl, 1,2- diethyl butyl, 1- ethyl -2,2- dimethylbutyls, 1,1- dimethyl -2- ethyl-butyls, 1- propyl group -
2- methyl butyls, n-nonyl, 1- Methyl Octyls, 2- Methyl Octyls, 3- Methyl Octyls, 4- Methyl Octyls, 5- Methyl Octyls, 1,1-
Dimethyl heptyl, 1,2- dimethyl heptyl, 1,3- dimethyl heptyl, 1,4- dimethyl heptyl, 1- ethylheptyls, 2- ethyls heptan
Base, 3- ethylheptyls, 4- ethylheptyls, 1,1,2- trimethyls, 1,1,3- trimethyls, 2,2,3- trimethyls,
1,2,3- trimethyls, 1- Ethyl-2-Methyls hexyl, 1- ethyl -3- methylhexyls, 1- propyl group hexyl, 2- propyl group hexyl, 3-
Propyl group hexyl, 1- isopropyls hexyl, 2- isopropyls hexyl, 3- isopropyls hexyl, 1,1,2,2- tetramethyls amyl group, 1,1,3,3- tetra-
Methyl amyl, 1,2,2,3- tetramethyls amyl group, 1,2,3,3- tetramethyls amyl group, 1- ethyl -2,2- dimethyl amyl groups, 1- ethyls -
2,3- dimethyl amyl groups, 1,2- dimethyl -1- ethyl pentyl groups, 1- propyl group -2- methyl amyls, 1,1,2,2,3- trimethyl butyls,
3- methyl isophthalic acids, 2- diethyl butyl, positive decyl, 1- Nonyls, 2- Nonyls, 3- Nonyls, 4- Nonyls, 5- first
Base nonyl, 1,1- dimethyl octyl group, 1,3- dimethyl octyl group, 1,4- dimethyl octyl group, 1,5- dimethyl octyl group, 2,2- dimethyl
Octyl group, 2,3- dimethyl octyl group, 2,4- dimethyl octyl group, 2,5- dimethyl octyl group, 3,3- dimethyl octyl group, 3,4- dimethyl-octas
Base, 3,5- dimethyl octyl group, 4,4- dimethyl octyl group, 4,5- dimethyl octyl group, 1- ethyloctanyls, 2- ethyloctanyls, 3- ethyls
Octyl group, 4- ethyloctanyls, 1,1,2- trimethyls heptyl, 1,1,3- trimethyls heptyl, 1,1,4- trimethyls heptyl, 1- ethyls -2-
Methylheptyl, 1- methyl -2- ethylheptyls, 1- propylheptyls, 2- propylheptyls, 3- propylheptyls, 1- isopropyls heptyl, 2- are different
Propylheptyl, 3- isopropyls heptyl, 1,1,2,2- tetramethylhexyls, 1,1,3,3- tetramethylhexyls, 1,2,2,3- tetramethyls oneself
Base, 1,2,3,3- tetramethylhexyls, 1- ethyl -2,2- dimethylhexanyls, 1- ethyl -2,3- dimethylhexanyls, 1,2- dimethyl -
1- ethylhexyls or 1- propyl group -2- methylhexyls；
The aryl of C6~C30 be phenyl, 1- naphthyls, 2- naphthyls, 1- anthryls, 2- anthryls, 9- anthryls, 1- phenanthryl, 2- phenanthryl,
3- phenanthryl, 4- phenanthryl, 9- phenanthryl, 1- aphthacenes base, 2- aphthacenes base, 9- aphthacenes base, 1- pyrenyls, 2- pyrenyls, 4- pyrenyls, 2-
Xenyl, 3- xenyls, 4- xenyls, para-terpheny -4- bases, para-terpheny -3- bases, para-terpheny -2- bases, meta-terphenyl -
4- bases, meta-terphenyl -3- bases, meta-terphenyl -2- bases, o-tolyl, a tolyl, p-methylphenyl, to tert-butyl-phenyl, p-
(2- phenyl propyls) phenyl, 3- methyl -2- naphthyls, 4- methyl isophthalic acids-naphthyl, 4- methyl isophthalic acids-anthryl, 4'- methyl biphenyls or 4 " -
The tert-butyl group-para-terpheny -4- bases.
In a kind of preferred embodiment of the organic compound that the present invention is provided, phenyl, pyridine radicals in R1 or R6, naphthalene
In base, phenanthryl, anthryl, phenanthridinyl, xenyl, pyrimidine radicals or triazine radical, more than one hydrogen is independently by the straight chain of C1~C20
Alkyl or branched alkyl, the cycloalkyl of C3~C24, the alkoxy of C1~C20, halogen, cyano group, trifluoromethyl, trimethyl silicon substrate,
Naphthyl, anthryl, phenanthryl, benzofuranyl, dibenzofuran group, fluorenyl, carbazyl, Spirofluorene-based or annular atom number are 5~20
Heteroaryl is replaced.
In a preferred embodiment, annular atom number is that 5~20 heteroaryl is 1- pyrrole radicals, 2- pyrrole radicals, 3- pyrroles
Cough up base, 1- pyridine radicals, 2- pyridine radicals, 3- pyridine radicals, 4- pyridine radicals, 1- indyls, 2- indyls, 3- indyls, 4- indyls,
5- indyls, 6- indyls, 7- indyls, 1- isoindolyls, 2- isoindolyls, 3- isoindolyls, 4- isoindolyls, the different Yin of 5-
Diindyl base, 6- isoindolyls, 7- isoindolyls, 2- furyls, 3- furyls, 2- benzofuranyls, 3- benzofuranyls, 4- benzos
Furyl, 5- benzofuranyls, 6- benzofuranyls, 7- benzofuranyls, 1- isobenzofuran-bases, 3- isobenzofuran-bases,
4- isobenzofuran-bases, 5- isobenzofuran-bases, 6- isobenzofuran-bases, 7- isobenzofuran-bases, 2- quinolyls, 3- quinoline
Base, 4- quinolyls, 5- quinolyls, 6- quinolyls, 7- quinolyls, 8- quinolyls, 1- isoquinolyls, 3- isoquinolyls, 4- isoquinolines
Quinoline base, 5- isoquinolyls, 6- isoquinolyls, 7- isoquinolyls, 8- isoquinolyls, 2- quinoxalinyls, 5- quinoxalinyls, 6- quinolines
Quinoline base, 1- coffee piperidinyl, 2- coffee piperidinyl, 3- coffee piperidinyl, 4- coffee piperidinyl, 6- coffee piperidinyl, 7- coffee piperidinyl, 8- coffee piperidinyl, 9- coffee piperidinyl,
10- coffee piperidinyl, 1,7- phenanthrene cough up beautiful jade -2- bases, 1,7- phenanthrene and cough up beautiful jade -3- bases, 1,7- phenanthrene and cough up beautiful jade -4- bases, 1,7- phenanthrene and cough up beautiful jade -5- bases, 1,
7- phenanthrene coughs up beautiful jade -6- bases, 1,7- phenanthrene and coughs up beautiful jade -8- bases, 1,7- phenanthrene and cough up beautiful jade -9- bases, 1,7- phenanthrene and cough up beautiful jade -10- bases, 1,8- phenanthrene and coughs up beautiful jade -2-
Base, 1,8- phenanthrene cough up beautiful jade -3- bases, 1,8- phenanthrene and cough up beautiful jade -4- bases, 1,8- phenanthrene and cough up beautiful jade -5- bases, 1,8- phenanthrene and cough up beautiful jade -6- bases, 1,8- phenanthrene and cough up
Beautiful jade -7- bases, 1,8- phenanthrene cough up beautiful jade -9- bases, 1,8- phenanthrene and cough up beautiful jade -10- bases, 1,9- phenanthrene and cough up beautiful jade -2- bases, 1,9- phenanthrene and cough up beautiful jade -3- bases, 1,9-
Phenanthrene cough up beautiful jade -4- bases, 1,9- phenanthrene cough up beautiful jade -5- bases, 1,9- phenanthrene cough up beautiful jade -6- bases, 1,9- phenanthrene cough up beautiful jade -7- bases, 1,9- phenanthrene cough up beautiful jade -8- bases,
1,9- phenanthrene coughs up beautiful jade -10- bases, 1,10- phenanthrene and coughs up beautiful jade -2- bases, 1,10- phenanthrene and cough up beautiful jade -3- bases, 1,10- phenanthrene and cough up beautiful jade -4- bases, 1,10- phenanthrene and coughs up
Beautiful jade -5- bases, 2,9- phenanthrolines -1- bases, 2,9- phenanthrene cough up beautiful jade -3- bases, 2,9- phenanthrene and cough up beautiful jade -4- bases, 2,9- phenanthrene and cough up beautiful jade -5- bases, 2,9-
Phenanthrene cough up beautiful jade -6- bases, 2,9- phenanthrene cough up beautiful jade -7- bases, 2,9- phenanthrene cough up beautiful jade -8- bases, 2,9- phenanthrene cough up beautiful jade -10- bases, 2,8- phenanthrene cough up beautiful jade -1- bases,
2,8- phenanthrene coughs up beautiful jade -3- bases, 2,8- phenanthrene and coughs up beautiful jade -4- bases, 2,8- phenanthrene and cough up beautiful jade -5- bases, 2,8- phenanthrene and cough up beautiful jade -6- bases, 2,8- phenanthrene and coughs up beautiful jade -7-
Base, 2,8- phenanthrene cough up beautiful jade -9- bases, 2,8- phenanthrene and cough up beautiful jade -10- bases, 2,7- phenanthrene and cough up beautiful jade -1- bases, 2,7- phenanthrene and cough up beautiful jade -3- bases, 2,7- phenanthrene and cough up
Beautiful jade -4- bases, 2,7- phenanthrene cough up beautiful jade -5- bases, 2,7- phenanthrene and cough up beautiful jade -6- bases, 2,7- phenanthrene and cough up beautiful jade -8- bases, 2,7- phenanthrene and cough up beautiful jade -9- bases, 2,7-
Phenanthrene coughs up beautiful jade -10- bases, 2- oxazolyls, 4- oxazolyls, 5- oxazolyls, 2- oxadiazolyls, 5- oxadiazolyls, 3- furazanyls, 2- thiophene
Base, 3- thienyls, 2- picoline -1- bases, 2- methylpyrrole -3- bases, 2- methylpyrrole -4- bases, 2- methylpyrrole -5- bases,
3- methylpyrrole -1- bases, 3- methylpyrrole -2- bases, 3- methylpyrrole -4- bases or 3- methylpyrrole -5- bases.
In a preferred embodiment, R2, R3, R4, R5, R7 and R8 be each independently methyl, ethyl, n-propyl,
Normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, positive decyl, phenyl, 1-
Naphthyl, 2- naphthyls, 1- anthryls, 2- anthryls, 9- anthryls, 1- phenanthryl, 2- phenanthryl, 3- phenanthryl, 4- phenanthryl, 9- phenanthryl, 1- aphthacenes
Base, 2- aphthacenes base, 9- aphthacenes base, 1- pyrenyls, 2- pyrenyls, 4- pyrenyls, 2- xenyls, 3- xenyls, 4- xenyls, to three
Biphenyl -4- bases, para-terpheny -3- bases, para-terpheny -2- bases, meta-terphenyl -4- bases, meta-terphenyl -3- bases, meta-terphenyl -2-
Base, o-tolyl, a tolyl, p-methylphenyl, to tert-butyl-phenyl, p- (2- phenyl propyls) phenyl, 3- methyl -2- naphthyls,
4- methyl isophthalic acids-naphthyl, 4- methyl isophthalic acids-anthryl, 4'- methyl biphenyls or the 4 "-tert-butyl group-para-terpheny -4- bases.
In a preferred embodiment, R2 and R3, R4 and R5, R7 and R8 can be combined with each other respectively, form aliphatic
Ring or aromatic ring.
In a preferred embodiment, in the aryl of the C6~C30 in Ar1, Ar2 or Ar3, more than one hydrogen independence
Ground by heavy hydrogen, halogen, the alkyl of C1~C10, the alkenyl of C2~C10, the alkoxy of C1~C10, the aryl of C6~C30 or C5~
The heteroaryl of C30 is replaced；
Wherein, the aryl of C6~C30 is phenyl, 1- naphthyls, 2- naphthyls, 1- anthryls, 2- anthryls, 9- anthryls, 1- phenanthryl, 2-
Phenanthryl, 3- phenanthryl, 4- phenanthryl, 9- phenanthryl, 1- aphthacenes base, 2- aphthacenes base, 9- aphthacenes base, 1- pyrenyls, 2- pyrenyls, 4- pyrenes
Base, 2- xenyls, 3- xenyls, 4- xenyls, para-terpheny -4- bases, para-terpheny -3- bases, para-terpheny -2- bases, three
Biphenyl -4- bases, meta-terphenyl -3- bases, meta-terphenyl -2- bases, o-tolyl, a tolyl, p-methylphenyl, to tert-butyl benzene
Base, p- (2- phenyl propyls) phenyl, 3- methyl -2- naphthyls, 4- methyl isophthalic acids-naphthyl, 4- methyl isophthalic acids-anthryl, 4'- methyl biphenyls
Base or the 4 "-tert-butyl group-para-terpheny -4- bases；
The alkyl of C1~C10 is methyl, ethyl, n-propyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, n-pentyl, just
Hexyl, n-heptyl, n-octyl, n-nonyl or positive decyl；
The alkenyl vinyl base of C2~C10, pi-allyl, acrylic, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 1- amylenes
Base, 2- pentenyls, 3- pentenyls, 2-methyl-1-butene alkenyl, 3-methyl-1-butene base, 2- methyl-2-butenes base, 1- hexenes
Base, 2- hexenyls, 3- hexenyls, 2- methyl-1-pentenes alkenyl, 2- methyl -2- pentenyls, 4- methyl -2- pentenyls, 4- methyl -
1- pentenyls, 3- methyl-1-pentenes alkenyl, 3- methyl -2- pentenyls, 2- ethyl -1- cyclobutenyls, 3,3- dimethyl -1- cyclobutenyls,
2,3- dimethyl -1- cyclobutenyls, 2,3- dimethyl -2- butylene, 1- heptenyls or 1- octenyls, 1- nonenyls or 1- decene bases；
The heteroaryl of C5~C30 is 1- pyridine radicals, 2- pyridine radicals, 3- pyridine radicals, 4- pyridine radicals, 1- indyls, 2- indoles
Base, 3- indyls, 4- indyls, 5- indyls, 6- indyls, 7- indyls, 1- isoindolyls, 2- isoindolyls, the different Yin of 3-
Diindyl base, 4- isoindolyls, 5- isoindolyls, 6- isoindolyls, 7- isoindolyls, 2- benzofuranyls, 3- benzofuranyls, 4-
Benzofuranyl, 5- benzofuranyls, 6- benzofuranyls, 7- benzofuranyls, 1- isobenzofuran-bases, 3- isobenzofurans
Base, 4- isobenzofuran-bases, 5- isobenzofuran-bases, 6- isobenzofuran-bases, 7- isobenzofuran-bases, 2- quinolyls, 3- quinolines
Quinoline base, 4- quinolyls, 5- quinolyls, 6- quinolyls, 7- quinolyls, 8- quinolyls, 1- isoquinolyls, 3- isoquinolyls, 4- are different
Quinolyl, 5- isoquinolyls, 6- isoquinolyls, 7- isoquinolyls, 8- isoquinolyls, 2- quinoxalinyls, 5- quinoxalinyls, 6- quinolines
Quinoline base, 1- coffee piperidinyl, 2- coffee piperidinyl, 3- coffee piperidinyl, 4- coffee piperidinyl, 6- coffee piperidinyl, 7- coffee piperidinyl, 8- coffee piperidinyl, 9- coffee pyridines
Base, 10- coffee piperidinyl, 1,7- phenanthrene cough up beautiful jade -2- bases, 1,7- phenanthrene cough up beautiful jade -3- bases, 1,7- phenanthrene cough up beautiful jade -4- bases, 1,7- phenanthrene cough up beautiful jade -5- bases,
1,7- phenanthrene cough up beautiful jade -6- bases, 1,7- phenanthrene cough up beautiful jade -8- bases, 1,7- phenanthrene cough up beautiful jade -9- bases, 1,7- phenanthrene cough up beautiful jade -10- bases, 1,8- phenanthrene cough up beautiful jade -
2- bases, 1,8- phenanthrene cough up beautiful jade -3- bases, 1,8- phenanthrene and cough up beautiful jade -4- bases, 1,8- phenanthrene and cough up beautiful jade -5- bases, 1,8- phenanthrene and cough up beautiful jade -6- bases, 1,8- phenanthrene and cough up
Beautiful jade -7- bases, 1,8- phenanthrene cough up beautiful jade -9- bases, 1,8- phenanthrene and cough up beautiful jade -10- bases, 1,9- phenanthrene and cough up beautiful jade -2- bases, 1,9- phenanthrene and cough up beautiful jade -3- bases, 1,9-
Phenanthrene cough up beautiful jade -4- bases, 1,9- phenanthrene cough up beautiful jade -5- bases, 1,9- phenanthrene cough up beautiful jade -6- bases, 1,9- phenanthrene cough up beautiful jade -7- bases, 1,9- phenanthrene cough up beautiful jade -8- bases,
1,9- phenanthrene coughs up beautiful jade -10- bases, 1,10- phenanthrene and coughs up beautiful jade -2- bases, 1,10- phenanthrene and cough up beautiful jade -3- bases, 1,10- phenanthrene and cough up beautiful jade -4- bases, 1,10- phenanthrene and coughs up
Beautiful jade -5- bases, 2,9- phenanthrolines -1- bases, 2,9- phenanthrene cough up beautiful jade -3- bases, 2,9- phenanthrene and cough up beautiful jade -4- bases, 2,9- phenanthrene and cough up beautiful jade -5- bases, 2,9-
Phenanthrene cough up beautiful jade -6- bases, 2,9- phenanthrene cough up beautiful jade -7- bases, 2,9- phenanthrene cough up beautiful jade -8- bases, 2,9- phenanthrene cough up beautiful jade -10- bases, 2,8- phenanthrene cough up beautiful jade -1- bases,
2,8- phenanthrene coughs up beautiful jade -3- bases, 2,8- phenanthrene and coughs up beautiful jade -4- bases, 2,8- phenanthrene and cough up beautiful jade -5- bases, 2,8- phenanthrene and cough up beautiful jade -6- bases, 2,8- phenanthrene and coughs up beautiful jade -7-
Base, 2,8- phenanthrene cough up beautiful jade -9- bases, 2,8- phenanthrene and cough up beautiful jade -10- bases, 2,7- phenanthrene and cough up beautiful jade -1- bases, 2,7- phenanthrene and cough up beautiful jade -3- bases, 2,7- phenanthrene and cough up
Beautiful jade -4- bases, 2,7- phenanthrene cough up beautiful jade -5- bases, 2,7- phenanthrene and cough up beautiful jade -6- bases, 2,7- phenanthrene and cough up beautiful jade -8- bases, 2,7- phenanthrene and cough up beautiful jade -9- bases, 2,7-
Phenanthrene cough up beautiful jade -10- bases, 2- picoline -1- bases, 2- methylpyrrole -3- bases, 2- methylpyrrole -4- bases, 2- methylpyrrole -5- bases,
3- methylpyrrole -1- bases, 3- methylpyrrole -2- bases, 3- methylpyrrole -4- bases or 3- methylpyrrole -5- bases.
The organic compound that the present invention is provided is further described in detail with reference to embodiment 1-6.
Embodiment 1
A kind of organic compound 15, structural formula is as follows：
Compound 15 is prepared from by following methods：
The synthesis of intermediate -1
[reaction equation 1]
28.3g (100mmol) neighbour's bromo-iodobenzenes and the bromo- 1- of 24.4g (110mmol) 7- are added in dry 2L there-necked flasks
Naphthylamines, the 600ml toluene for adding dry and degasification makees solvent.Add 28.8g (300mmol) sodium tert-butoxide, 0.45g catalysis
Agent palladium (2%mol) and 2.5g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.110 DEG C are warming up to,
Reaction 6 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, tied again with toluene and ethanol
Crystalline substance, obtains intermediate -1 of 35.7g, and yield is 86%.
The synthesis of intermediate -2
[reaction equation 2]
Experimental provision is fully dried, intermediate -1 of 35.7g (94.6mml, 1.1eq.) is added in 2L there-necked flasks,
The tetrahydrofuran for adding 700ml dried, is cooled to -78 DEG C after dissolving, 51.6ml 2.0M (103.2mmol, 1.2eq.) is added dropwise
N-BuLi.Stirred at such a temperature after completion of dropwise addition 1 hour, then 5.0g (86mmol, 1.0eq.) third is added dropwise at such a temperature
Ketone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, is extracted with dichloromethane, and organic phase is used
Saturated common salt is washed to neutrality, dries, rotation removes solvent, fully dries, then be dosed into 2L dry there-necked flask, add
400ml acetic anhydrides, are warming up to 120 DEG C, flow back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, molten with dichloromethane
Solution, adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains intermediate -2 of 20.9g, produces
Rate is 72%.
The synthesis of intermediate -3
[reaction equation 3]
By the intermediate -2 of 20.9g (61.9mmol) and 8.3g (68.1mmol) phenyl boric acid, the there-necked flask of 2L is added to
In, 400ml toluene and the dissolving of 100ml ethanol are added, lead to nitrogen 15 minutes, add 92.9ml K2CO3(185.7mmol,2M)
The aqueous solution, be eventually adding 1.43g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus activated carbon is inhaled
Attached, suction filtration, rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains intermediate -3 of 17.6g, and yield is 85%.
The synthesis of intermediate -4
[reaction equation 4]
During the intermediate -3 of 17.6g (52.6mmol) put into the there-necked flask of 1L, solvent is made with 400ml DMF, then
10.3g (57.9mmol) NBS is added under the conditions of room temperature lucifuge, room temperature lucifuge is reacted 18 hours.Question response terminates, and adds saturation
Na2SO3Solution, separates out a large amount of solids, stirs 1 hour, and suction filtration is repeatedly rinsed with water, then with alcohol flushing 1 time, first is used after drying
Benzene and ethyl alcohol recrystallization, obtain intermediate -4 of 19.2g, yield 88%.
The synthesis of intermediate -5
[reaction equation 5]
The intermediate -4 and 8.6g (42.1mmol) iodine of 19.2g (46.3mmol) are added in dry 2L there-necked flasks
Benzene, the 400ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 12.1g (126.3mmol) tertiary fourth
Sodium alkoxide, 0.77g (2%mol) catalyst Pd2(dba)3With 3.4ml (4%mol) P (t-bu)3Toluene solution (m/v, 10%).
110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, uses first
Benzene and ethyl alcohol recrystallization, obtain intermediate -5 of 19.0g, and yield is 92%.
The synthesis of intermediate -6
[reaction equation 6]
Experimental provision is fully dried, intermediate -5 of 19g (38.7mmol, 1.0eq.) is added in 2L there-necked flasks,
Add the dried tetrahydrofurans of 500ml, -78 DEG C be cooled to after dissolving, be added dropwise 21.3ml 2M LDA (42.6mmol,
1.1eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then add at such a temperature 14.7g iodine (58.1mmol,
1.5eq.), it is stirred at room temperature after completion of dropwise addition 12 hours.Question response terminates, and adds 4M hydrochloric acid solutions, is extracted with dichloromethane, has
Machine saturated common salt is washed to neutrality, dries, and rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtain the intermediate of 19.8g-
6, yield is 83%.
The synthesis of intermediate -7
[reaction equation 7]
By bromobenzeneboronic acid between the intermediate -6 of 19.8g (32.1mmol) and 7.1g (35.3mmol), three mouthfuls of 2L are added to
In flask, 400ml toluene and the dissolving of 100ml ethanol are added, lead to nitrogen 15 minutes, add 48.2ml K2CO3(96.3mmol,
Aqueous solution 2M), is eventually adding 0.74g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus activity
Charcoal is adsorbed, suction filtration, and rotation removes solvent, is dried, and with toluene and ethyl alcohol recrystallization, obtains intermediate -7 of 16.2g, and yield is 78%.
The synthesis of intermediate -8
[reaction equation 8]
Experimental provision is fully dried, intermediate -7 of 16.2g (25.0mml, 1.1eq.) is added in 2L there-necked flasks,
The tetrahydrofuran for adding 300ml dried, is cooled to -78 DEG C after dissolving, 10.9ml 2.5M (27.4mmol, 1.2eq.) is added dropwise
N-BuLi.Stirred at such a temperature after completion of dropwise addition 1 hour, then 4.1g (22.8mmol, 1.0eq.) is added dropwise at such a temperature
Benzophenone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, is extracted with dichloromethane, has
Machine saturated common salt is washed to neutrality, dries, rotation removes solvent, fully dries, then be dosed into 2L dry there-necked flask, plus
Enter 200ml acetic anhydrides, be warming up to 120 DEG C, flow back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, molten with dichloromethane
Solution, adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains intermediate -8 of 13.2g, produces
Rate is 79%.
The synthesis of intermediate -9
[reaction equation 9]
The intermediate -8 and 6.5g (19.9mmol) 4- of 13.2g (18.1mmol) are added in dry 2L there-necked flasks
(2- bromobenzenes amido) biphenyl, the 260ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 5.2g
(54.3mmol) sodium tert-butoxide, 0.33g (2%mol) catalyst Pd2(dba)3With 1.5ml (4%mol) P (t-bu)3Toluene it is molten
Liquid (m/v, 10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, suction filtration,
Rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains intermediate -9 of 15.7g, and yield is 89%.
The synthesis of compound 15
[reaction equation 10]
Experimental provision is fully dried, intermediate -9 of 15.7g (16.1mml, 1.1eq.) is added in 2L there-necked flasks,
The tetrahydrofuran for adding 360ml dried, is cooled to -78 DEG C after dissolving, be added dropwise 7.0ml's 2.5M (17.5mmol, 1.2eq.)
n-BuLi.Stirred at such a temperature after completion of dropwise addition 1 hour, then 2.7g (14.6mmol, 1.0eq.) two is added dropwise at such a temperature
Benzophenone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, is extracted with dichloromethane, organic
Be washed to neutrality with saturated common salt, dry, rotation removes solvent, fully dries, then be dosed into 2L dry there-necked flask, add
400ml acetic anhydrides, are warming up to 120 DEG C, flow back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, molten with dichloromethane
Solution, adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains the compound 15 of 9.4g, produces
Rate is 61%.
It is below the proton nmr spectra of compound 15：1H NMR(DMSO,300Hz):δ (ppm)=8.32-8.11 (d,
1H),7.94-7.83(d,1H),7.81-7.72(s,1H),7.67-7.51(m,11H),7.49-6.93(m,35H),6.88-
6.59(m,7H),6.56-6.42(m,2H)
MS(FAB):1059(M+)
Embodiment 2
A kind of organic compound 36, structural formula is as follows：
Compound 36 is prepared from by following methods：
The synthesis of intermediate -10
[reaction equation 11]
28.3g (100mmol) neighbour's bromo-iodobenzenes and 15.8g (110mmol) naphthalidine are added in dry 2L there-necked flasks,
The 600ml toluene for adding dry and degasification makees solvent.Add 28.8g (300mmol) sodium tert-butoxide, 0.45g catalyst vinegar
Sour palladium (2%mol) and 2.5g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.It is warming up to 110 DEG C, reaction 6
Hour.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains
Intermediate -10 of 24.2g, yield is 81%.
The synthesis of intermediate -11
[reaction equation 12]
Experimental provision is fully dried, intermediate -10 of 24.2g (81mml, 1.1eq.) is added in 2L there-necked flasks,
The tetrahydrofuran for adding 700ml dried, is cooled to -78 DEG C after dissolving, 44.2ml 2.0M (88.3mmol, 1.2eq.) is added dropwise
N-BuLi.Stirred at such a temperature after completion of dropwise addition 1 hour, then 13.3g (73.6mmol, 1.0eq.) is added dropwise at such a temperature
Dibenzofurans, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, is extracted with dichloromethane,
Organic phase saturated common salt is washed to neutrality, dries, rotation removes solvent, fully dries, then be dosed into 2L dry there-necked flask,
400ml acetic anhydrides are added, 120 DEG C are warming up to, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, uses dichloromethane
Dissolving, adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, with toluene and ethyl alcohol recrystallization, obtain the intermediate of 23.3g-
11, yield is 83%.
The synthesis of intermediate -12
[reaction equation 13]
During the intermediate -11 of 23.3g (61.1mmol) put into the there-necked flask of 1L, solvent is made with 400ml DMF, then
12.0g (67.2mmol) NBS is added under the conditions of room temperature lucifuge, room temperature lucifuge is reacted 18 hours.Question response terminates, and adds saturation
Na2SO3Solution, separates out a large amount of solids, stirs 1 hour, and suction filtration is repeatedly rinsed with water, then with alcohol flushing 1 time, first is used after drying
Benzene and ethyl alcohol recrystallization, obtain intermediate -12 of 23.9g, yield 85%.
The synthesis of intermediate -13
[reaction equation 14]
The intermediate -12 and 5.5g (57.1mmol) fluorine of 23.9g (51.9mmol) are added in dry 2L there-necked flasks
Benzene, the 500ml DMF for adding dry and degasification make solvent, are slow added into 50.7g (155.7mmol) cesium carbonate.Heat up
To 160 DEG C, react 15 hours.Question response terminates, and is cooled to room temperature, and add water stirring 1 hour, has solid to generate, suction filtration, plus on a small quantity
Alcohol flushing, dries, and with toluene and ethyl alcohol recrystallization, obtains intermediate -13 of 24.8g, and yield is 89%.
The synthesis of intermediate -14
[reaction equation 15]
By experimental provision fully dry, in 2L there-necked flasks add 24.8g (46.2mmol, 1.0eq.) intermediate-
13, add the dried tetrahydrofurans of 500ml, -78 DEG C are cooled to after dissolving, be added dropwise 25.4ml 2M LDA (50.8mmol,
THF solution 1.1eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then add 17.6g iodine at such a temperature
(69.3mmol, 1.5eq.), is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Alkane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains 25.4g
Intermediate -14, yield is 83%.
The synthesis of intermediate -15
[reaction equation 16]
By bromobenzeneboronic acid between the intermediate -14 of 25.4g (38.3mmol) and 8.5g (42.1mmol), three mouthfuls of 2L are added to
In flask, 500ml toluene and the dissolving of 100ml ethanol are added, lead to nitrogen 15 minutes, add 57.5ml K2CO3(115mmol,
Aqueous solution 2M), is eventually adding 0.89g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus activity
Charcoal is adsorbed, suction filtration, and rotation removes solvent, is dried, and with toluene and ethyl alcohol recrystallization, obtains intermediate -15 of 19.3g, and yield is 73%.
The synthesis of intermediate -16
[reaction equation 17]
By experimental provision fully dry, in 2L there-necked flasks add 19.3g (28.0mml, 1.1eq.) intermediate-
15, add the dried tetrahydrofurans of 360ml, -78 DEG C are cooled to after dissolving, be added dropwise 12.2ml 2.5M (30.5mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 4.6g (25.4mmol,
1.0eq.) benzophenone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Extraction, organic phase saturated common salt is washed to neutrality, dries, and rotation removes solvent, fully dries, then is dosed into three mouthfuls of burnings of drying of 2L
In bottle, 200ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, with two
Chloromethanes dissolves, and adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, with toluene and ethyl alcohol recrystallization, in obtaining 14.0g
Mesosome -16, yield is 71%.
The synthesis of intermediate -17
[reaction equation 18]
The intermediate -16 and 1.8g (19.8mmol) benzene of 14.0g (18.0mmol) are added in dry 2L there-necked flasks
Amine, the 300ml toluene for adding dry and degasification makees solvent.Add 5.2g (54.0mmol) sodium tert-butoxide, 0.08g catalyst
Palladium (2%mol) and 0.45g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.110 DEG C are warming up to, instead
Answer 6 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, suction filtration, and rotation removes solvent, with toluene and ethyl alcohol recrystallization,
Intermediate -17 of 13.2g are obtained, yield is 93%.
The synthesis of intermediate -18
[reaction equation 19]
The intermediate -17 and 5.7g (18.4mmol) 1 of 13.2g (16.7mmol) are added in dry 2L there-necked flasks,
The bromo- 4- biphenyl of 2- bis-, the 300ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 4.8g
(50.1mmol) sodium tert-butoxide, 0.31g (2%mol) catalyst Pd2(dba)3With 1.4ml (4%mol) P (t-bu)3Toluene it is molten
Liquid (m/v, 10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, suction filtration,
Rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains intermediate -18 of 12.1g, and yield is 71%.
The synthesis of compound 36
[reaction equation 20]
By experimental provision fully dry, in 2L there-necked flasks add 12.1g (11.9mml, 1.1eq.) intermediate-
18, add the dried tetrahydrofurans of 240ml, -78 DEG C are cooled to after dissolving, be added dropwise 5.2ml 2.5M (13.0mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 2.0g (10.8mmol,
1.0eq.) benzophenone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Extraction, organic phase saturated common salt is washed to neutrality, dries, and rotation removes solvent, fully dries, then is dosed into three mouthfuls of burnings of drying of 2L
In bottle, 400ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, with two
Chloromethanes dissolves, and adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains the chemical combination of 7.4g
Thing 36, yield is 62%.
It is below the proton nmr spectra of compound 36：1H NMR(DMSO,300Hz):δ (ppm)=8.32-8.10 (d,
1H),8.02-7.79(m,4H),7.77-7.69(m,2H),7.67-7.51(m,9H),7.49-6.93(m,34H),6.91-
6.79(m,6H)
MS(FAB):1105(M+)
Embodiment 3
A kind of organic compound 57, structural formula is as follows：
Compound 57 is prepared from by following methods：
The synthesis of intermediate -19
[reaction equation 21]
28.3g (100mmol) neighbour's bromo-iodobenzenes and 15.8g (110mmol) naphthalidine are added in dry 2L there-necked flasks,
The 600ml toluene for adding dry and degasification makees solvent.Add 28.8g (300mmol) sodium tert-butoxide, 0.45g catalyst vinegar
Sour palladium (2%mol) and 2.5g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.It is warming up to 110 DEG C, reaction 6
Hour.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains
Intermediate -19 of 24.2g, yield is 81%.
The synthesis of intermediate -20
[reaction equation 22]
Experimental provision is fully dried, intermediate -19 of 24.2g (81mml, 1.1eq.) is added in 2L there-necked flasks,
The tetrahydrofuran for adding 700ml dried, is cooled to -78 DEG C after dissolving, 44.2ml 2.0M (88.3mmol, 1.2eq.) is added dropwise
N-BuLi.Stirred at such a temperature after completion of dropwise addition 1 hour, then 17.1g (73.6mmol, 1.0eq.) is added dropwise at such a temperature
2- Benzophenone naphthalenes, are stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, is extracted with dichloromethane,
Organic phase saturated common salt is washed to neutrality, dries, rotation removes solvent, fully dries, then be dosed into 2L dry there-necked flask,
400ml acetic anhydrides are added, 120 DEG C are warming up to, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, uses dichloromethane
Dissolving, adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, with toluene and ethyl alcohol recrystallization, obtain the intermediate of 27.1g-
20, yield is 85%.
The synthesis of intermediate -21
[reaction equation 23]
During the intermediate -20 of 27.1g (62.6mmol) put into the there-necked flask of 1L, solvent is made with 400ml DMF, then
12.2g (68.8mmol) NBS is added under the conditions of room temperature lucifuge, room temperature lucifuge is reacted 18 hours.Question response terminates, and adds saturation
Na2SO3Solution, separates out a large amount of solids, stirs 1 hour, and suction filtration is repeatedly rinsed with water, then with alcohol flushing 1 time, first is used after drying
Benzene and ethyl alcohol recrystallization, obtain intermediate -21 of 28.6g, yield 89%.
The synthesis of intermediate -22
[reaction equation 24]
The intermediate -21 and 5.4g (55.8mmol) fluorine of 28.6g (55.8mmol) are added in dry 2L there-necked flasks
Benzene, the 500ml DMF for adding dry and degasification make solvent, are slow added into 54.5g (167.4mmol) cesium carbonate.Heat up
To 160 DEG C, react 15 hours.Question response terminates, and is cooled to room temperature, and add water stirring 1 hour, has solid to generate, suction filtration, plus on a small quantity
Alcohol flushing, dries, and with toluene and ethyl alcohol recrystallization, obtains intermediate -22 of 28.6g, and yield is 87%.
The synthesis of intermediate -23
[reaction equation 25]
By experimental provision fully dry, in 2L there-necked flasks add 28.6g (48.5mmol, 1.0eq.) intermediate-
22, add the dried tetrahydrofurans of 500ml, -78 DEG C are cooled to after dissolving, be added dropwise 26.7ml 2M LDA (53.4mmol,
THF solution 1.1eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then add 18.5g iodine at such a temperature
(72.8mmol, 1.5eq.), is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Alkane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains 27.4g
Intermediate -23, yield is 79%.
The synthesis of intermediate -24
[reaction equation 26]
By bromobenzeneboronic acid between the intermediate -23 of 27.4g (38.3mmol) and 8.5g (42.1mmol), three mouthfuls of 2L are added to
In flask, 500ml toluene and the dissolving of 100ml ethanol are added, lead to nitrogen 15 minutes, add 57.5ml K2CO3(115mmol,
Aqueous solution 2M), is eventually adding 0.89g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus activity
Charcoal is adsorbed, suction filtration, and rotation removes solvent, is dried, and with toluene and ethyl alcohol recrystallization, obtains intermediate -24 of 23.4g, and yield is 82%.
The synthesis of intermediate -25
[reaction equation 27]
By experimental provision fully dry, in 2L there-necked flasks add 23.4g (31.4mml, 1.1eq.) intermediate-
24, add the dried tetrahydrofurans of 360ml, -78 DEG C are cooled to after dissolving, be added dropwise 13.7ml 2.5M (34.3mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 5.2g (28.6mmol,
1.0eq.) benzophenone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Extraction, organic phase saturated common salt is washed to neutrality, dries, and rotation removes solvent, fully dries, then is dosed into three mouthfuls of burnings of drying of 2L
In bottle, 200ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, with two
Chloromethanes dissolves, and adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, with toluene and ethyl alcohol recrystallization, in obtaining 17.3g
Mesosome -25, yield is 73%.
The synthesis of intermediate -26
[reaction equation 28]
The intermediate -25 and 5.2g (20.9mmol) 2- of 17.3g (20.9mmol) are added in dry 2L there-necked flasks
Bromophenyl aniline, the 300ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 5.9g
(61.8mmol) sodium tert-butoxide, 0.38g (2%mol) catalyst Pd2(dba)3With 1.7ml (4%mol) P (t-bu)3Toluene it is molten
Liquid (m/v, 10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, suction filtration,
Rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains intermediate -26 of 16.9g, and yield is 81%.
The synthesis of compound 57
[reaction equation 29]
By experimental provision fully dry, in 2L there-necked flasks add 16.9g (16.9mml, 1.1eq.) intermediate-
26, add the dried tetrahydrofurans of 240ml, -78 DEG C are cooled to after dissolving, be added dropwise 7.4ml 2.5M (18.5mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 4.0g (15.4mmol,
1.0eq.) 4- (Benzophenone base) biphenyl, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses
Dichloromethane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, fully dries, then is dosed into the dry of 2L
In dry there-necked flask, 400ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation is except molten
Agent, is dissolved with dichloromethane, adds suitable quantity of water 3 times, is dried, and rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains
The compound 57 of 12.3g, yield is 69%.
It is below the proton nmr spectra of compound 57：1H NMR(DMSO,300Hz):δ (ppm)=8.22-8.07 (d,
1H),8.04-7.83(m,4H),7.75-7.47(m,14H),7.45-7.05(m,27H),7.03-6.91(m,4H),6.88-
6.77(m,2H),6.73-6.57(m,6H),6.54-6.42(m,2H)
MS(FAB):1157(M+)
Embodiment 4
A kind of organic compound 77, structural formula is as follows：
Compound 77 is prepared from by following methods：
The synthesis of intermediate -27
[reaction equation 30]
28.3g (100mmol) neighbour's bromo-iodobenzenes and the bromo- 1- of 24.4g (110mmol) 7- are added in dry 2L there-necked flasks
Naphthylamines, the 600ml toluene for adding dry and degasification makees solvent.Add 28.8g (300mmol) sodium tert-butoxide, 0.45g catalysis
Agent palladium (2%mol) and 2.5g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.110 DEG C are warming up to,
Reaction 6 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, tied again with toluene and ethanol
Crystalline substance, obtains intermediate -27 of 35.7g, and yield is 86%.
The synthesis of intermediate -28
[reaction equation 31]
By experimental provision fully dry, in 2L there-necked flasks add 35.7g (94.6mml, 1.1eq.) intermediate-
27, add the dried tetrahydrofurans of 700ml, -78 DEG C are cooled to after dissolving, be added dropwise 51.6ml 2.0M (103.2mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 15.7g (86mmol,
1.0eq.) benzophenone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Extraction, organic phase saturated common salt is washed to neutrality, dries, and rotation removes solvent, fully dries, then is dosed into three mouthfuls of burnings of drying of 2L
In bottle, 400ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, with two
Chloromethanes dissolves, and adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, with toluene and ethyl alcohol recrystallization, in obtaining 27.8g
Mesosome -28, yield is 70%.
The synthesis of intermediate -29
[reaction equation 32]
By the intermediate -28 of 27.8g (60.2mmol) and 11.4g (66.2mmol) 1- naphthalene boronic acids, three mouthfuls of 2L are added to
In flask, 600ml toluene and the dissolving of 150ml ethanol are added, lead to nitrogen 15 minutes, add 90.3ml K2CO3(180.6mmol,
Aqueous solution 2M), is eventually adding 1.40g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus activity
Charcoal is adsorbed, suction filtration, and rotation removes solvent, is dried, and with toluene and ethyl alcohol recrystallization, obtains intermediate -29 of 26.7g, and yield is 87%.
The synthesis of intermediate -30
[reaction equation 33]
During the intermediate -29 of 26.7g (52.4mmol) put into the there-necked flask of 1L, solvent is made with 500ml DMF, then
10.3g (57.6mmol) NBS is added under the conditions of room temperature lucifuge, room temperature lucifuge is reacted 18 hours.Question response terminates, and adds saturation
Na2SO3Solution, separates out a large amount of solids, stirs 1 hour, and suction filtration is repeatedly rinsed with water, then with alcohol flushing 1 time, first is used after drying
Benzene and ethyl alcohol recrystallization, obtain intermediate -30 of 27.4g, yield 89%.
The synthesis of intermediate -31
[reaction equation 34]
The intermediate -30 and 10.9g (42.4mmol) of 27.4g (46.6mmol) are added in dry 2L there-necked flasks
The bromo- 2- cyanobiphenyls of 3'-, the 400ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 12.2g
(127.2mmol) sodium tert-butoxide, 0.78g (2%mol) catalyst Pd2(dba)3With 3.4ml (4%mol) P (t-bu)3Toluene
Solution (m/v, 10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, takes out
Filter, rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains intermediate -31 of 27.6g, and yield is 85%.
The synthesis of intermediate -32
[reaction equation 35]
By experimental provision fully dry, in 2L there-necked flasks add 27.6g (36.0mmol, 1.0eq.) intermediate-
31, add the dried tetrahydrofurans of 500ml, -78 DEG C are cooled to after dissolving, be added dropwise 19.8ml 2M LDA (39.6mmol,
THF solution 1.1eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then add 13.7g iodine at such a temperature
(54.0mmol, 1.5eq.), is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Alkane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains 27.6g
Intermediate -32, yield is 86%.
The synthesis of intermediate -33
[reaction equation 36]
By bromobenzeneboronic acid between the intermediate -32 of 27.6g (31.0mmol) and 6.8g (34.1mmol), three mouthfuls of 2L are added to
In flask, 600ml toluene and the dissolving of 150ml ethanol are added, lead to nitrogen 15 minutes, add 46.5ml K2CO3(93.0mmol,
Aqueous solution 2M), is eventually adding 0.72g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus activity
Charcoal is adsorbed, suction filtration, and rotation removes solvent, is dried, and with toluene and ethyl alcohol recrystallization, obtains intermediate -33 of 22.5g, and yield is 79%.
The synthesis of intermediate -34
[reaction equation 37]
By experimental provision fully dry, in 2L there-necked flasks add 22.5g (24.5mml, 1.1eq.) intermediate-
33, add the dried tetrahydrofurans of 300ml, -78 DEG C are cooled to after dissolving, be added dropwise 10.7ml 2.5M (26.8mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 5.2g (22.3mmol,
1.0eq.) 2- (Benzophenone) naphthalene, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloro
Methane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, fully dries, then the drying three for being dosed into 2L
In mouth flask, 200ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent,
Dissolved with dichloromethane, add suitable quantity of water 3 times, dried, rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains 15.8g
Intermediate -34, yield is 66%.
The synthesis of intermediate -35
[reaction equation 38]
Added in dry 2L there-necked flasks 28.3g (100mmol) neighbours bromo-iodobenzene and 24.4g (110mmol) 4- naphthyls-
2- amido anthracenes, the 600ml toluene for adding dry and degasification makees solvent.Add 28.8g (300mmol) sodium tert-butoxide, 0.45g
Catalyst acetic acid palladium (2%mol) and 2.5g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.It is warming up to 110
DEG C, react 6 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, with toluene and ethanol weight
Crystallization, obtains intermediate -35 of 37.5g, and yield is 79%.
The synthesis of intermediate -36
[reaction equation 39]
The intermediate -34 and 7.0g (14.7mmol) of 15.8g (14.7mmol) are added in dry 2L there-necked flasks
Intermediate -35, the 300ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 4.2g (44.1mmol)
Sodium tert-butoxide, 0.27g (2%mol) catalyst Pd2(dba)3With 1.2ml (4%mol) P (t-bu)3Toluene solution (m/v,
10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes molten
Agent, with toluene and ethyl alcohol recrystallization, obtains intermediate -36 of 17.0g, and yield is 80%.
The synthesis of compound 77
[reaction equation 40]
By experimental provision fully dry, in 2L there-necked flasks add 17.0g (11.8mml, 1.1eq.) intermediate-
36, add the dried tetrahydrofurans of 360ml, -78 DEG C are cooled to after dissolving, be added dropwise 5.1ml 2.5M (12.8mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 3.0g (10.7mmol,
1.0eq.) 2- (2- naphthyls) ketone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and 4M hydrochloric acid solutions is added, with two
Chloromethanes is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, fully dries, then the drying for being dosed into 2L
In there-necked flask, 120 DEG C are warming up to, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, is dissolved with dichloromethane,
Add suitable quantity of water 3 times, dry, rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains 10.7g compounds 77, and yield is
61%.
It is below the proton nmr spectra of compound 77：1H NMR(DMSO,300Hz):δ (ppm)=8.65-8.51 (m,
2H),8.47-8.34(m,2H),8.22-8.11(m,2H),8.08-7.76(m,20H),7.74-7.68(d,1H),7.66-
7.47(m,14H),7.45-6.94(m,31H),6.91-6.83(m,2H),6.76-6.66(m,2H),6.62-6.56(d,1H),
6.54-6.42(m,2H)
MS(FAB):1635(M+)
Embodiment 5
A kind of organic compound 89, structural formula is as follows：
Compound 89 is prepared from by following methods：
The synthesis of intermediate -37
[reaction equation 41]
28.3g (100mmol) neighbour's bromo-iodobenzenes and 15.8g (110mmol) naphthalidine are added in dry 2L there-necked flasks,
The 600ml toluene for adding dry and degasification makees solvent.Add 28.8g (300mmol) sodium tert-butoxide, 0.45g catalyst vinegar
Sour palladium (2%mol) and 2.5g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.It is warming up to 110 DEG C, reaction 6
Hour.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains
Intermediate -37 of 24.2g, yield is 81%.
The synthesis of intermediate -38
[reaction equation 42]
Experimental provision is fully dried, intermediate -37 of 24.2g (81mml, 1.1eq.) is added in 2L there-necked flasks,
The tetrahydrofuran for adding 700ml dried, is cooled to -78 DEG C after dissolving, 44.2ml 2.0M (88.3mmol, 1.2eq.) is added dropwise
N-BuLi.Stirred at such a temperature after completion of dropwise addition 1 hour, then 8.8g (73.6mmol, 1.0eq.) is added dropwise at such a temperature
Acetophenone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, is extracted with dichloromethane, organic
Be washed to neutrality with saturated common salt, dry, rotation removes solvent, fully dries, then be dosed into 2L dry there-necked flask, add
400ml acetic anhydrides, are warming up to 120 DEG C, flow back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, molten with dichloromethane
Solution, adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains intermediate -38 of 18.7g,
Yield is 79%.
The synthesis of intermediate -39
[reaction equation 43]
During the intermediate -38 of 18.7g (58.1mmol) put into the there-necked flask of 1L, solvent is made with 400ml DMF, then
11.4g (64.0mmol) NBS is added under the conditions of room temperature lucifuge, room temperature lucifuge is reacted 18 hours.Question response terminates, and adds saturation
Na2SO3Solution, separates out a large amount of solids, stirs 1 hour, and suction filtration is repeatedly rinsed with water, then with alcohol flushing 1 time, first is used after drying
Benzene and ethyl alcohol recrystallization, obtain intermediate -39 of 25.6g, yield 86%.
The synthesis of intermediate -40
[reaction equation 44]
The intermediate -39 and 12.7g (45.4mmol) 4- of 25.6g (50.0mmol) are added in dry 2L there-necked flasks
Iodine biphenyl, the 300ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 13.1g (136.2mmol)
Sodium tert-butoxide, 0.83g (2%mol) catalyst Pd2(dba)3With 3.7ml (4%mol) P (t-bu)3Toluene solution (m/v,
10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes molten
Agent, with toluene and ethyl alcohol recrystallization, obtains intermediate -40 of 22.3g, and yield is 89%.
The synthesis of intermediate -41
[reaction equation 45]
By experimental provision fully dry, in 2L there-necked flasks add 22.3g (40.4mmol, 1.0eq.) intermediate-
40, add the dried tetrahydrofurans of 500ml, -78 DEG C are cooled to after dissolving, be added dropwise 22.2ml 2M LDA (44.4mmol,
THF solution 1.1eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then add 15.4g iodine at such a temperature
(60.6mmol, 1.5eq.), is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Alkane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains 22.2g
Intermediate -41, yield is 81%.
The synthesis of intermediate -42
[reaction equation 46]
By bromobenzeneboronic acid between the intermediate -41 of 22.2g (32.7mmol) and 7.2g (36.0mmol), three mouthfuls of 2L are added to
In flask, 500ml toluene and the dissolving of 100ml ethanol are added, lead to nitrogen 15 minutes, add 49.1ml K2CO3(98.1mmol,
Aqueous solution 2M), is eventually adding 0.78g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus activity
Charcoal is adsorbed, suction filtration, and rotation removes solvent, is dried, and with toluene and ethyl alcohol recrystallization, obtains intermediate -42 of 18.0g, and yield is 78%.
The synthesis of intermediate -43
[reaction equation 47]
By experimental provision fully dry, in 2L there-necked flasks add 18.0g (25.5mml, 1.1eq.) intermediate-
42, add the dried tetrahydrofurans of 360ml, -78 DEG C are cooled to after dissolving, be added dropwise 11.1ml 2.5M (27.8mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 6.0g (23.2mmol,
1.0eq.) 4- (Benzophenone) biphenyl, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and 4M hydrochloric acid solutions is added, with two
Chloromethanes is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, fully dries, then the drying for being dosed into 2L
In there-necked flask, 200ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation is except molten
Agent, is dissolved with dichloromethane, adds suitable quantity of water 3 times, is dried, and rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains
Intermediate -43 of 14.5g, yield is 72%.
The synthesis of intermediate -44
[reaction equation 48]
The intermediate -43 and 4.6g (18.4mmol) (2- of 14.5g (16.7mmol) are added in dry 2L there-necked flasks
Bromophenyl) aniline, add and dry and the 300ml toluene of degasification makees solvent, lead to nitrogen 15 minutes.Add 4.8g
(50.1mmol) sodium tert-butoxide, 0.31g (2%mol) catalyst Pd2(dba)3With 1.4ml (4%mol) P (t-bu)3Toluene it is molten
Liquid (m/v, 10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, suction filtration,
Rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains intermediate -44 of 14.2g, and yield is 82%.
The synthesis of compound 89
[reaction equation 49]
By experimental provision fully dry, in 2L there-necked flasks add 14.2g (13.7mml, 1.1eq.) intermediate-
44, add the dried tetrahydrofurans of 300ml, -78 DEG C are cooled to after dissolving, be added dropwise 6.0ml 2.5M (14.9mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 3.2g (12.4mmol,
1.0eq.) 4- (Benzophenone base) biphenyl, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses
Dichloromethane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, fully dries, then is dosed into the dry of 2L
In dry there-necked flask, 400ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation is except molten
Agent, is dissolved with dichloromethane, adds suitable quantity of water 3 times, is dried, and rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains
The compound 89 of 10.7g, yield is 72%.
It is below the proton nmr spectra of compound 89：1H NMR(DMSO,300Hz):δ (ppm)=8.23-8.10 (d,
1H),8.03-7.91(d,1H),7.67-7.50(m,12H),7.48-6.94(m,38H),6.88-6.53(m,8H),6.51-
6.42(d,1H),2.48-2.24(s,3H)
MS(FAB):1197(M+)
Embodiment 6
A kind of organic compound 112, structural formula is as follows：
Compound 112 is prepared from by following methods：
The synthesis of intermediate -45
[reaction equation 50]
28.3g (100mmol) neighbour's bromo-iodobenzenes and 15.8g (110mmol) naphthalidine are added in dry 2L there-necked flasks,
The 600ml toluene for adding dry and degasification makees solvent.Add 28.8g (300mmol) sodium tert-butoxide, 0.45g catalyst vinegar
Sour palladium (2%mol) and 2.5g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.It is warming up to 110 DEG C, reaction 6
Hour.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains
Intermediate -45 of 24.2g, yield is 81%.
The synthesis of intermediate -46
[reaction equation 51]
Experimental provision is fully dried, intermediate -45 of 24.2g (81mml, 1.1eq.) is added in 2L there-necked flasks,
The tetrahydrofuran for adding 700ml dried, is cooled to -78 DEG C after dissolving, 44.2ml 2.0M (88.3mmol, 1.2eq.) is added dropwise
N-BuLi.Stirred at such a temperature after completion of dropwise addition 1 hour, then 19.0g (73.6mmol, 1.0eq.) is added dropwise at such a temperature
4- (Benzophenone) biphenyl, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Extraction, organic phase saturated common salt is washed to neutrality, dries, and rotation removes solvent, fully dries, then is dosed into three mouthfuls of burnings of drying of 2L
In bottle, 400ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, with two
Chloromethanes dissolves, and adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, with toluene and ethyl alcohol recrystallization, in obtaining 25.7g
Mesosome -46, yield is 76%.
The synthesis of intermediate -47
[reaction equation 52]
During the intermediate -46 of 25.7g (55.9mmol) put into the there-necked flask of 1L, solvent is made with 500ml DMF, then
11.0g (61.5mmol) NBS is added under the conditions of room temperature lucifuge, room temperature lucifuge is reacted 18 hours.Question response terminates, and adds saturation
Na2SO3Solution, separates out a large amount of solids, stirs 1 hour, and suction filtration is repeatedly rinsed with water, then with alcohol flushing 1 time, first is used after drying
Benzene and ethyl alcohol recrystallization, obtain intermediate -47 of 25.9g, yield 86%.
The synthesis of intermediate -48
[reaction equation 53]
By the bromo- 3- iodine naphthalenes of 33.3g (100mmol) 1- and 18.9g (110mmol) 2- naphthalene boronic acids, three mouthfuls of burnings of 2L are added to
In bottle, 600ml toluene and the dissolving of 150ml ethanol are added, lead to nitrogen 15 minutes, add 150ml K2CO3(300mmol, 2M's)
The aqueous solution, is eventually adding 2.3g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus charcoal absorption,
Suction filtration, rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains intermediate -48 of 26.3g, and yield is 79%.
The synthesis of intermediate -49
[reaction equation 54]
The intermediate -48 and 26.3g (48.1mmol) of 14.6g (43.7mmol) are added in dry 2L there-necked flasks
Intermediate -47, the 300ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 12.6g
(131.1mmol) sodium tert-butoxide, 0.80g (2%mol) catalyst Pd2(dba)3With 3.5ml (4%mol) P (t-bu)3Toluene
Solution (m/v, 10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, takes out
Filter, rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains intermediate -49 of 29.7g, and yield is 86%.
The synthesis of intermediate -50
[reaction equation 55]
By experimental provision fully dry, in 2L there-necked flasks add 29.7g (37.6mmol, 1.0eq.) intermediate-
49, add the dried tetrahydrofurans of 500ml, -78 DEG C are cooled to after dissolving, be added dropwise 20.7ml 2M LDA (41.3mmol,
THF solution 1.1eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then add 14.3g iodine at such a temperature
(56.4mmol, 1.5eq.), is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Alkane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, with toluene and ethyl alcohol recrystallization, obtains 29.6g
Intermediate -50, yield is 86%.
The synthesis of intermediate -51
[reaction equation 56]
By bromobenzeneboronic acid between the intermediate -50 of 29.6g (32.3mmol) and 7.1g (35.5mmol), three mouthfuls of 2L are added to
In flask, 600ml toluene and the dissolving of 150ml ethanol are added, lead to nitrogen 15 minutes, add 48.5ml K2CO3(96.9mmol,
Aqueous solution 2M), is eventually adding 0.75g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus activity
Charcoal is adsorbed, suction filtration, and rotation removes solvent, is dried, and with toluene and ethyl alcohol recrystallization, obtains intermediate -51 of 29.6g, and yield is 97%.
The synthesis of intermediate -52
[reaction equation 57]
By experimental provision fully dry, in 2L there-necked flasks add 29.6g (31.3mml, 1.1eq.) intermediate-
51, add the dried tetrahydrofurans of 360ml, -78 DEG C are cooled to after dissolving, be added dropwise 13.7ml 2.5M (34.2mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 5.2g (28.5mmol,
1.0eq.) benzophenone, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloromethane
Extraction, organic phase saturated common salt is washed to neutrality, dries, and rotation removes solvent, fully dries, then is dosed into three mouthfuls of burnings of drying of 2L
In bottle, 200ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent, with two
Chloromethanes dissolves, and adds suitable quantity of water 3 times, dries, and rotation removes solvent, dries, with toluene and ethyl alcohol recrystallization, in obtaining 20.9g
Mesosome -52, yield is 71%.
The synthesis of intermediate -53
[reaction equation 58]
By the bromo- 6- iodobenzenes of 33.3g (100mmol) 2- and 18.9g (110mmol) 2- naphthalene boronic acids, three mouthfuls of burnings of 2L are added to
In bottle, 600ml toluene and the dissolving of 150ml ethanol are added, lead to nitrogen 15 minutes, add 150ml K2CO3(300mmol, 2M's)
The aqueous solution, is eventually adding 2.3g Pd (PPh3)4(2mol%).110 DEG C are warming up to, reaction terminates for 12 hours.Plus charcoal absorption,
Suction filtration, rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains intermediate -53 of 27.3g, and yield is 82%.
The synthesis of intermediate -54
[reaction equation 59]
Intermediate -53 and 15.5g (90.2mmol) neighbour's bromine of 27.3g (82mmol) are added in dry 2L there-necked flasks
Aniline, the 600ml toluene for adding dry and degasification makees solvent.Add 23.6g (246mmol) sodium tert-butoxide, 0.37g catalysis
Agent palladium (2%mol) and 2.0g ligand 1s, 1'- dinaphthalene -2, the double diphenyl phosphines (BINAP, 4%mol) of 2'-.110 DEG C are warming up to,
Reaction 6 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes solvent, tied again with toluene and ethanol
Crystalline substance, obtains intermediate -54 of 29.6g, and yield is 85%.
The synthesis of intermediate -54
[reaction equation 59]
The intermediate -52 and 8.6g (20.3mmol) of 20.9g (20.3mmol) are added in dry 2L there-necked flasks
Intermediate -54, the 400ml toluene for adding dry and degasification makees solvent, leads to nitrogen 15 minutes.Add 5.9g (60.9mmol)
Sodium tert-butoxide, 0.37g (2%mol) catalyst Pd2(dba)3With 1.6ml (4%mol) P (t-bu)3Toluene solution (m/v,
10%).110 DEG C are warming up to, are reacted 16 hours.Question response terminates, and is cooled to room temperature, plus charcoal absorption, and suction filtration, rotation removes molten
Agent, with toluene and ethyl alcohol recrystallization, obtains intermediate -55 of 22.3g, and yield is 80%.
The synthesis of compound 112
[reaction equation 60]
By experimental provision fully dry, in 2L there-necked flasks add 22.3g (16.2mml, 1.1eq.) intermediate-
55, add the dried tetrahydrofurans of 300ml, -78 DEG C are cooled to after dissolving, be added dropwise 7.1ml 2.5M (17.8mmol,
N-BuLi 1.2eq.).Stirred at such a temperature after completion of dropwise addition 1 hour, then at such a temperature be added dropwise 3.8g (14.8mmol,
1.0eq.) 3- phenyl -9H- fluorenes, is stirred at room temperature 12 hours after completion of dropwise addition.Question response terminates, and adds 4M hydrochloric acid solutions, uses dichloro
Methane is extracted, and organic phase saturated common salt is washed to neutrality, is dried, and rotation removes solvent, fully dries, then the drying three for being dosed into 2L
In mouth flask, 400ml acetic anhydrides are added, be warming up to 120 DEG C, flowed back 5 hours, terminate reaction.Room temperature is cooled to, rotation removes solvent,
Dissolved with dichloromethane, add suitable quantity of water 3 times, dried, rotation removes solvent, dries, and with toluene and ethyl alcohol recrystallization, obtains 14.8g
Compound 112, yield is 65%.
It is below the proton nmr spectra of compound 112：1H NMR(DMSO,300Hz):δ (ppm)=8.32-7.77 (m,
13H),7.75-7.48(m,25H),7.46-7.18(m,21H),7.16-7.05(m,8H),7.03-6.92(m,4H),6.82-
6.73(s,1H),6.71-6.62(m,2H),6.56-6.42(m,2H)
MS(FAB):1533(M+)
" normal temperature " or " room temperature " in the various embodiments described above refers to 18 DEG C -28 DEG C.
Using the method for above-mentioned reaction equation 1-60, all organic compounds of present invention offer can be synthesized.
The structure of organic electroluminescence device of the invention is typical but is not limited to following several：
(1) anode/luminescent layer/negative electrode；
(2) anode/hole injection layer/luminescent layer/negative electrode；
(3) anode/hole injection layer/hole transmission layer/luminescent layer/negative electrode；
(4) anode/hole injection layer/hole transmission layer/electron-blocking layer/luminescent layer/negative electrode；
(5) anode/luminescent layer/electron injecting layer/negative electrode；
(6) anode/luminescent layer/electron transfer layer/electron injecting layer/negative electrode；
(7) anode/luminescent layer/hole blocking layer/electron transfer layer/electron injecting layer/negative electrode；
(8) anode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/negative electrode；
(9) anode/hole injection layer/hole transmission layer/electron-blocking layer/luminescent layer/hole blocking layer/electric transmission
Layer/electron injecting layer/negative electrode/coating.
It is the manufacture method of the organic electroluminescence device of (9) for structure, comprises the following steps：
Step 1, crosses anode material modeling and forms anode in substrate surface, and the substrate selection for being used has good clear
Property, the glass substrate or transparent plastic substrate of surface smoothness, operability and water proofing property, anode material can be using transparent and pass
The property led superior ITO, IZO, SnO2, ZnO etc..
Step 2, by hole injection layer material (HIL) vacuum heat deposition or is spin-coated on anode surface, hole injection layer material
Can be CuPc, m-MTDATA, m-MTDAPB, TCTA, 2-TNATA of star-like amine or from Japanese Idemitsu Kosen Co., Ltd.'s energy
IDE406 for enough buying etc..
Step 3, by hole transport layer material (HTL) vacuum heat deposition or be spin-coated on hole injection layer surface formed hole pass
Defeated layer.
Step 4, by electron-blocking layer material (EBL) vacuum heat deposition or be spin-coated on hole transport layer surface formed electronics resistance
Interlayer.
Step 5, by emitting layer material (EML) vacuum heat deposition or is spin-coated on hole transport layer surface, forms luminescent layer.
Step 6, by electron transport layer materials (ETL) vacuum heat deposition or is spin-coated on luminous layer surface and forms electric transmission
Layer.There is no particular limitation for electron transport layer materials, preferably uses Alq3。
Step 7, by electron injecting layer material (EIL) vacuum heat deposition or is spin-coated on electric transmission layer surface, forms electronics
Implanted layer.Electron injecting layer material can be LiF, Liq, Li2O, BaO, NaCl, CsF etc..
Step 8, by cathode material vacuum heat deposition or is spin-coated on electron injecting layer, forms negative electrode.Cathode material, Ke Yiwei
Li, Al, Al-Li, Ca, Mg, Mg-In, Mg-Ag etc..Alternatively, it is also possible to be made using tin indium oxide (ITO) or indium zinc oxide (IZO)
Into light transmissive transparent cathode.
Step 9, coating (CPL) can also be further formed in cathode surface.There is no particular limitation for covering layer material,
Organic compound of the present invention can be used.
Step 10, can also add hole blocking layer (HBL), while in luminescent layer between luminescent layer and electron transfer layer
It is used together phosphorescence doping, it is possible to achieve prevent triplet excitons or hole to be diffused into the effect of electron transfer layer.Using routine
Method is by hole blocking layer material (HBL) vacuum heat deposition or is spin-coated on luminous layer surface, forms hole blocking layer.Hole intercepts
There is no particular limitation for layer material, and organic compound preferably of the invention, Liq, 2- methyl -8-hydroxyquinoline parazon are closed
Aluminium, BCP and LiF etc..
The organic electroluminescence device provided with reference to 1 couple of present invention of embodiment 7-18 and reference examples does further in detail
Explanation.
Embodiment 7
A kind of organic electroluminescence device, including anode, hole injection layer, hole transmission layer, the electronics resistance for setting gradually
Interlayer, luminescent layer, electron transfer layer, electron injecting layer, negative electrode and coating, the material of hole transmission layer is compound 3.
Above-mentioned organic electroluminescence device is prepared from by following steps：On the substrate in existing reflecting layer, ITO sun is formed
Pole, uses N2Ion or UV-Ozone are surface-treated.On herein, steamed as hole injection layer (HIL) material with HAT-CN
Plate the thickness of 10nm.Next on above-mentioned hole injection layer top, with compound of the invention, selection compound 3 is carried out very
Sky evaporation, forms the hole transmission layer (HTL) of 120nm thickness.TCTA is deposited with above-mentioned hole transmission layer overhead vacuum, is formed
The electron-blocking layer (EBL) of 15nm.In luminescent layer (EML) above above-mentioned electron-blocking layer, use 9,10- bis- (2- naphthyls)
Anthracene (ADN) is deposited with the thickness of 25nm as main substance, while left as dopant doping about 5% using t-Bu-Perylene
It is right.With 1 on herein:1 weight is deposited with the electron transfer layer (ETL) of 35nm thickness than the derivative and Liq of mixing anthracene,
Its top is deposited with the Liq of 2nm as electron injecting layer (EIL).Afterwards, 9 are pressed with magnesium (Mg) and silver-colored (Ag):1 ratio is mixed
The mixture of conjunction is deposited with the N4 of 65nm, N4 '-bis- [4- [double (3- first as the thickness of cathode evaporation 15nm above above-mentioned negative electrode
Base phenyl) ammonia] phenyl]-N4, N4 '-hexichol-[1,1 '-biphenyl] -4,4 '-diamines (DNTPD) is used as coating (CPL).Finally,
Used on its paper and sealed containing UV curable adhesives absorbent material, to protect organic electroluminescence device not by the oxygen in air
Gas or moisture are influenceed.
The structural formula of involved compound is as follows in the present embodiment：
Embodiment 8~18
Respectively using compound 9,15,26,36,40,45,57,77,89,99 and 112 as hole transmission layer (HTL) material,
Other parts are consistent with embodiment 7, and the organic electroluminescence device of embodiment 8~18 is produced accordingly.
Reference examples 1
Difference with embodiment 7 is to replace organic compound of the invention as hole transmission layer material using NPD,
Remaining is same as Example 7.
The organic electroluminescence device that embodiment 7~18 and reference examples 1 are prepared is in current density 10mA/cm2's
Under the conditions of carry out performance test, it is as a result as shown in the table.
As can be known from the above table, sent out as organic electroluminescence prepared by the material of hole transmission layer using organic compound of the invention
Compared with reference examples 1, luminous efficiency is significantly improved the embodiment 7~18 of optical device, and driving voltage is substantially reduced.
In addition, knowable to above-mentioned experimental result, using organic compound of the invention as hole transporting material, Organic Electricity
The luminous efficiency of electroluminescence device is improved.Therefore, organic matter of the invention can reduce the driving voltage of device, and then subtract
Few power consumption.Additionally by low voltage drive, the life-span of organic electroluminescence device also increases.
Although illustrate and describing the present invention with specific embodiment, but will be appreciated that without departing substantially from of the invention
Many other changes and modification can be made in the case of spirit and scope.It is, therefore, intended that in the following claims
Including belonging to all such changes and modifications in the scope of the invention.
Claims (10)
1. a kind of organic compound, it is characterised in that the structural formula of the compound is as follows：
Wherein, R1 and R6 are each independently heavy hydrogen, the straight chained alkyl of optionally substituted C1~C20 or branched alkyl, optionally take
The phenyl in generation, optionally substituted pyridine radicals, optionally substituted naphthyl, optionally substituted phenanthryl, optionally substituted anthryl, optionally take
In the phenanthridinyl in generation, optionally substituted xenyl, optionally substituted pyrimidine radicals or optionally substituted triazine radical any one or
At least two combination；
R2, R3, R4, R5, R7 and R8 are each independently the alkyl of C1~C10 and/or the aryl of C6~C30；
Ar1, Ar2 or Ar3 are each independently the straight chained alkyl or branched alkane of hydrogen, heavy hydrogen, halogen, optionally substituted C1~C20
In the aryl of base or optionally substituted C6~C30 any one or at least two combination.
2. organic compound according to claim 1, it is characterised in that R1Or phenyl, pyridine radicals, naphthyl, phenanthrene in R6
In base, anthryl, phenanthridinyl, xenyl, pyrimidine radicals or triazine radical, more than one hydrogen is independently by the straight chained alkyl of C1~C20
Or cycloalkyl, the alkoxy of C1~C20, halogen, cyano group, trifluoromethyl, trimethyl silicon substrate, the naphthalene of branched alkyl, C3~C24
Base, anthryl, phenanthryl, benzofuranyl, dibenzofuran group, fluorenyl, carbazyl, Spirofluorene-based or annular atom number be 5~20 it is miscellaneous
Aryl is replaced.
3. organic compound according to claim 2, it is characterised in that the annular atom number is that 5~20 heteroaryl is
1- pyrrole radicals, 2- pyrrole radicals, 3- pyrrole radicals, 1- pyridine radicals, 2- pyridine radicals, 3- pyridine radicals, 4- pyridine radicals, 1- indyls, 2- Yin
Diindyl base, 3- indyls, 4- indyls, 5- indyls, 6- indyls, 7- indyls, 1- isoindolyls, 2- isoindolyls, 3- are different
Indyl, 4- isoindolyls, 5- isoindolyls, 6- isoindolyls, 7- isoindolyls, 2- furyls, 3- furyls, 2- benzo furans
Mutter base, 3- benzofuranyls, 4- benzofuranyls, 5- benzofuranyls, 6- benzofuranyls, 7- benzofuranyls, the different benzene of 1-
And furyl, 3- isobenzofuran-bases, 4- isobenzofuran-bases, 5- isobenzofuran-bases, 6- isobenzofuran-bases, the different benzos of 7-
Furyl, 2- quinolyls, 3- quinolyls, 4- quinolyls, 5- quinolyls, 6- quinolyls, 7- quinolyls, 8- quinolyls, 1- isoquinolines
Quinoline base, 3- isoquinolyls, 4- isoquinolyls, 5- isoquinolyls, 6- isoquinolyls, 7- isoquinolyls, 8- isoquinolyls, 2- quinolines
Quinoline base, 5- quinoxalinyls, 6- quinoxalinyls, 1- coffee piperidinyl, 2- coffee piperidinyl, 3- coffee piperidinyl, 4- coffee piperidinyl, 6- coffee piperidinyl, 7- coffee
Piperidinyl, 8- coffee piperidinyl, 9- coffee piperidinyl, 10- coffee piperidinyl, 1,7- phenanthrene cough up beautiful jade -2- bases, 1,7- phenanthrene cough up beautiful jade -3- bases, 1,7- phenanthrene cough up beautiful jade -
4- bases, 1,7- phenanthrene cough up beautiful jade -5- bases, 1,7- phenanthrene and cough up beautiful jade -6- bases, 1,7- phenanthrene and cough up beautiful jade -8- bases, 1,7- phenanthrene and cough up beautiful jade -9- bases, 1,7- phenanthrene and cough up
Beautiful jade -10- bases, 1,8- phenanthrene cough up beautiful jade -2- bases, 1,8- phenanthrene and cough up beautiful jade -3- bases, 1,8- phenanthrene and cough up beautiful jade -4- bases, 1,8- phenanthrene and cough up beautiful jade -5- bases, 1,8-
Phenanthrene cough up beautiful jade -6- bases, 1,8- phenanthrene cough up beautiful jade -7- bases, 1,8- phenanthrene cough up beautiful jade -9- bases, 1,8- phenanthrene cough up beautiful jade -10- bases, 1,9- phenanthrene cough up beautiful jade -2- bases,
1,9- phenanthrene coughs up beautiful jade -3- bases, 1,9- phenanthrene and coughs up beautiful jade -4- bases, 1,9- phenanthrene and cough up beautiful jade -5- bases, 1,9- phenanthrene and cough up beautiful jade -6- bases, 1,9- phenanthrene and coughs up beautiful jade -7-
Base, 1,9- phenanthrene cough up beautiful jade -8- bases, 1,9- phenanthrene and cough up beautiful jade -10- bases, 1,10- phenanthrene and cough up beautiful jade -2- bases, 1,10- phenanthrene to cough up beautiful jade -3- bases, 1,10- luxuriant and rich with fragrance
Cough up beautiful jade -4- bases, 1,10- phenanthrene and cough up beautiful jade -5- bases, 2,9- phenanthrolines -1- bases, 2,9- phenanthrene and cough up beautiful jade -3- bases, 2,9- phenanthrene and cough up beautiful jade -4- bases, 2,
9- phenanthrene coughs up beautiful jade -5- bases, 2,9- phenanthrene and coughs up beautiful jade -6- bases, 2,9- phenanthrene and cough up beautiful jade -7- bases, 2,9- phenanthrene and cough up beautiful jade -8- bases, 2,9- phenanthrene and coughs up beautiful jade -10-
Base, 2,8- phenanthrene cough up beautiful jade -1- bases, 2,8- phenanthrene and cough up beautiful jade -3- bases, 2,8- phenanthrene and cough up beautiful jade -4- bases, 2,8- phenanthrene and cough up beautiful jade -5- bases, 2,8- phenanthrene and cough up
Beautiful jade -6- bases, 2,8- phenanthrene cough up beautiful jade -7- bases, 2,8- phenanthrene and cough up beautiful jade -9- bases, 2,8- phenanthrene and cough up beautiful jade -10- bases, 2,7- phenanthrene and cough up beautiful jade -1- bases, 2,7-
Phenanthrene cough up beautiful jade -3- bases, 2,7- phenanthrene cough up beautiful jade -4- bases, 2,7- phenanthrene cough up beautiful jade -5- bases, 2,7- phenanthrene cough up beautiful jade -6- bases, 2,7- phenanthrene cough up beautiful jade -8- bases,
2,7- phenanthrene coughs up beautiful jade -9- bases, 2,7- phenanthrene and coughs up beautiful jade -10- bases, 2- oxazolyls, 4- oxazolyls, 5- oxazolyls, 2- oxadiazolyls, 5- Evil bis-
Oxazolyl, 3- furazanyls, 2- thienyls, 3- thienyls, 2- picoline -1- bases, 2- methylpyrrole -3- bases, 2- methylpyrroles -4-
Base, 2- methylpyrrole -5- bases, 3- methylpyrrole -1- bases, 3- methylpyrrole -2- bases, 3- methylpyrrole -4- bases or 3- methyl pyrroles
Cough up -5- bases.
4. organic compound according to claim 1, it is characterised in that R2, R3, R4, R5, R7 and R8 are each independently
Methyl, ethyl, n-propyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, n-pentyl, n-hexyl, n-heptyl, n-octyl, positive nonyl
Base, positive decyl, phenyl, 1- naphthyls, 2- naphthyls, 1- anthryls, 2- anthryls, 9- anthryls, 1- phenanthryl, 2- phenanthryl, 3- phenanthryl, 4- are luxuriant and rich with fragrance
Base, 9- phenanthryl, 1- aphthacenes base, 2- aphthacenes base, 9- aphthacenes base, 1- pyrenyls, 2- pyrenyls, 4- pyrenyls, 2- xenyls, 3- connection
Phenyl, 4- xenyls, para-terpheny -4- bases, para-terpheny -3- bases, para-terpheny -2- bases, meta-terphenyl -4- bases, three
Benzene -3- bases, meta-terphenyl -2- bases, o-tolyl, a tolyl, p-methylphenyl, to tert-butyl-phenyl, p- (2- phenyl propyls)
Phenyl, 3- methyl -2- naphthyls, 4- methyl isophthalic acids-naphthyl, 4- methyl isophthalic acids-anthryl, 4'- methyl biphenyls or the 4 "-tert-butyl group-to three
Biphenyl -4- bases.
5. organic compound according to claim 1, it is characterised in that R2 and R3, R4 and R5, R7 and R8 can distinguish phase
Mutually combine, form aliphatic ring or aromatic ring.
6. organic compound according to claim 1, it is characterised in that the aryl of the C6~C30 in Ar1, Ar2 or Ar3
In, more than one hydrogen independently by heavy hydrogen, halogen, the alkyl of C1~C10, the alkenyl of C2~C10, the alkoxy of C1~C10,
The aryl of C6~C30 or the heteroaryl of C5~C30 are replaced.
7. organic compound according to claim 1, it is characterised in that the compound is any in following compounds
It is a kind of：
8. application of the organic compound described in any one of claim 1-7 in luminescent device is prepared.
9. a kind of organic electroluminescence device, it is characterised in that intercepted including anode, hole injection layer, hole transmission layer, electronics
In layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and negative electrode, hole transmission layer and/or electron-blocking layer
Mixing including any of which organic compound or at least two organic compounds described in claim any one of 1-7
Thing.
10. a kind of organic electroluminescence device, it is characterised in that including anode, hole injection layer, hole transmission layer, luminescent layer,
Electron transfer layer, electron injecting layer and negative electrode, hole transmission layer include wherein any one described in claim any one of 1-7
Plant the mixture of organic compound or at least two organic compounds.
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| CN107805248A (en) * | 2017-11-01 | 2018-03-16 | 长春海谱润斯科技有限公司 | A kind of derivative containing benzimidazole structure and preparation method thereof and organic electroluminescence device |
| WO2019053049A1 (en) * | 2017-09-18 | 2019-03-21 | Cynora Gmbh | Organic molecules, in particular for use in optoelectronic devices |
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| CN104603122A (en) * | 2012-09-03 | 2015-05-06 | 保土谷化学工业株式会社 | Compound having indeno acridan ring structure, and organic electroluminescence element |
| WO2016027687A1 (en) * | 2014-08-20 | 2016-02-25 | 保土谷化学工業株式会社 | Organic electroluminescent element |
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| CN104603122A (en) * | 2012-09-03 | 2015-05-06 | 保土谷化学工业株式会社 | Compound having indeno acridan ring structure, and organic electroluminescence element |
| WO2016027687A1 (en) * | 2014-08-20 | 2016-02-25 | 保土谷化学工業株式会社 | Organic electroluminescent element |
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| WO2019053049A1 (en) * | 2017-09-18 | 2019-03-21 | Cynora Gmbh | Organic molecules, in particular for use in optoelectronic devices |
| CN107805248A (en) * | 2017-11-01 | 2018-03-16 | 长春海谱润斯科技有限公司 | A kind of derivative containing benzimidazole structure and preparation method thereof and organic electroluminescence device |
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