CN108084221A - Sila condensed ring analog derivative, its application and electroluminescent device - Google Patents
Sila condensed ring analog derivative, its application and electroluminescent device Download PDFInfo
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- CN108084221A CN108084221A CN201611040892.3A CN201611040892A CN108084221A CN 108084221 A CN108084221 A CN 108084221A CN 201611040892 A CN201611040892 A CN 201611040892A CN 108084221 A CN108084221 A CN 108084221A
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- silicon substrate
- sila
- condensed ring
- substitution
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Links
- 239000000463 material Substances 0.000 claims abstract description 38
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 33
- 239000010703 silicon Substances 0.000 claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims description 41
- 238000006467 substitution reaction Methods 0.000 claims description 28
- -1 Phenyl Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 229910000077 silane Inorganic materials 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- XDIWYXGVXYCUSV-UHFFFAOYSA-N 2-methylpropylsilicon Chemical compound CC(C)C[Si] XDIWYXGVXYCUSV-UHFFFAOYSA-N 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- CJQKFKQIFQGELD-UHFFFAOYSA-N propan-2-ylsilicon Chemical compound CC(C)[Si] CJQKFKQIFQGELD-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 238000009825 accumulation Methods 0.000 abstract description 2
- 230000009471 action Effects 0.000 abstract description 2
- 238000004132 cross linking Methods 0.000 abstract description 2
- 230000027756 respiratory electron transport chain Effects 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 12
- 238000007738 vacuum evaporation Methods 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- 150000005360 2-phenylpyridines Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000004411 aluminium Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012459 cleaning agent Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000002027 dichloromethane extract Substances 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- 238000009832 plasma treatment Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 238000004506 ultrasonic cleaning Methods 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 238000012795 verification Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229940096017 silver fluoride Drugs 0.000 description 5
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229950011260 betanaphthol Drugs 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 229940126208 compound 22 Drugs 0.000 description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical group C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000013040 bath agent Substances 0.000 description 2
- YCITZMJNBYYMJO-UHFFFAOYSA-N chloro(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](Cl)C1=CC=CC=C1 YCITZMJNBYYMJO-UHFFFAOYSA-N 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- YJMNOKOLADGBKA-UHFFFAOYSA-N cyanonaphthalene Natural products C1=CC=C2C(C#N)=CC=CC2=C1 YJMNOKOLADGBKA-UHFFFAOYSA-N 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003760 hair shine Effects 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ZTQZMPQJXABFNC-UHFFFAOYSA-N 2,2,4,6,6,8-hexamethyl-4,8-diphenyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound O1[Si](C)(C)O[Si](C)(C=2C=CC=CC=2)O[Si](C)(C)O[Si]1(C)C1=CC=CC=C1 ZTQZMPQJXABFNC-UHFFFAOYSA-N 0.000 description 1
- QAFFBUBNQSNVSZ-UHFFFAOYSA-N 2-bromo-1-iodonaphthalene Chemical class C1=CC=CC2=C(I)C(Br)=CC=C21 QAFFBUBNQSNVSZ-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- DBWGAXVWWNKFNI-UHFFFAOYSA-N [O].C1(=CC=CC=C1)[P]C1=CC=CC=C1 Chemical group [O].C1(=CC=CC=C1)[P]C1=CC=CC=C1 DBWGAXVWWNKFNI-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000004074 biphenyls Chemical group 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical class [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002790 naphthalenes Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229960001328 quadrosilan Drugs 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07F7/12—Organo silicon halides
-
- 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
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to photoelectric material applied technical fields, and in particular to sila condensed ring analog derivative, its application and electroluminescent device.The sila condensed ring analog derivative by the bonded different aromatic group of different loci in sila condensed ring class or changes bridge crosslinking structure, forms the electron transport material with high electron mobility characteristic using sila condensed ring class as core.The derivative of sila condensed ring class provided by the present invention is as electron transfer layer, silicon forms stronger covalent bond with halogen, with stronger drawing electronic action, sila heptatomic ring can retain fragrant ring property, the nonplanar structure that the sp3 hydridization of silicon is formed simultaneously can effectively reduce entire planes of molecules accumulation, and with high triplet, triplet exciton is avoided to return, suitable for fluorescence radiation and phosphorescent emitter system.
Description
Technical field
The invention belongs to photoelectric material applied technical fields, and in particular to sila condensed ring analog derivative, its application and it is electroluminescent
Luminescent device.
Background technology
Nineteen ninety, univ cambridge uk report utilize styrene conjugated polymer PPV [poly for the first time
(phenylenevinylene)] made by organic polymer light emitting diode (PLED) device (Burroughes J.H.,
Bradley D.D.C.,Brown A.R.,et al,Light-Emitting Diodes Based on Conjugated
Polymers.Nature 1990,347,539-541.), Organic Light Emitting Diode Materials direction has been widened again.1998
Year, Forrest et al. obtains phosphorescence triplet under room temperature by means of heavy metal atom effect for the first time and shines (Baldo M.A., O'
Brien D.F.,You Y.,et al,Highly Efficient Phosphorescent Emission from Organic
Electroluminescent Devices.Nature 1998,395(6698):151-154.).2011, Helander etc.
People uses lenticule technique for outing light so that green light power efficiency improves 2.3 times, while also reported that up to 290lm/W's is green
Optical device (Helander M.G., Wang Z.B., Qiu J., et al, Chlorinated Indium Tin Oxide
Electrodes with High Work Function for Organic Device Compatibility.Science
2011,332(6032):944-947.).Adachi reports the delayed fluorescence phenomenon (Lee that external quantum efficiency breaks through 5%
S.Y.,Yasuda T.,Nomura H.,et al,High-Efficiency Organic Light-Emitting Diodes
Utilizing Thermally Activated Delayed Fluorescence from Triazine-Based Donor–
Acceptor Hybrid Molecules.Applied Physics Letters 2012,101(9):093306 1-4.), profit
Singlet state is formed with triplet reversion transition under room temperature, fluorescent blue light efficiency is greatly improved, from this Organic Light Emitting Diode
The period booming into one.
The quality of electron transport material performance has OLED device critically important influence, an efficient electron transport material
Should possess suitable molecule L UMO and HOMO energy levels, higher electron mobility, good macroscopic property (including thermal decomposition
Temperature and glass transition temperature), characteristics, the electron transport material that we often use such as higher triplet energy level have pyridine derived
Object, oxazole derivatives, metallo-chelate, quinoline, quinoline derivant, phenazine/phenanthrene derivative etc..
Chinese patent 201110182996.9 discloses a kind of sila cyclopentene class compound and its preparation method and application,
And such substance is mainly as synthetic intermediate.
The content of the invention
To solve the deficiencies in the prior art, the present invention provides sila condensed ring analog derivative, its application and electroluminescent cells
Part.Such substance using sila condensed ring class as core, by the bonded different aromatic group of different loci in sila condensed ring class or
Change bridge crosslinking structure, form the electron transport material with high electron mobility characteristic.
Technical solution provided by the present invention is as follows：
Sila condensed ring analog derivative, with the general structure shown in formula (Ia) or formula (Ib)：
Wherein：
Ar1-Ar4Phenyl or naphthyl is independently selected from, also, at least one is naphthalene；
R1-R4It is independently selected from substituted or unsubstituted C1-C20Alkane group, substitution or it is unsubstituted
C1-C20Silane hydrocarbyl group, substitution or unsubstituted C6-C65Aromatic group, substitution or unsubstituted C6-C65
Fragrant silane group, substitution or unsubstituted C5-C65Heterocyclic group, substitution or unsubstituted C6-C65It is more
Cyclic group, substitution or unsubstituted C6-C65Arylene group or substitution or unsubstituted C6-C65Asia fragrance
Heterocyclic group, R1-R4Identical or different, X is halogen F, Cl, Br or I.
Specifically, with the general structure shown in formula (Ib), wherein：
C1-C20Alkane group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C1-C20Silane hydrocarbyl group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl
Base；
C6-C65Aromatic group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C6-C65Fragrant silane group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl
Base；
C5-C65Heterocyclic group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C6-C65Polycyclic moiety substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C6-C65Arylene group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl
Base；
C6-C65Sub- aromatic heterocycle group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl
Acyl group；
R1-R4It is identical or different；
X is halogen F, Cl, Br or I.
Preferably, C5-C65Heterocyclic group be C5-C65Heteroaromatic group；C6-C65Polycyclic moiety be C6-C65Contracting
Close polycyclic aromatic group.
It is furthermore preferred that the structure of sila condensed ring analog derivative is as follows：
Specifically, R1-R4It is independently selected from the structure shown in general formula 2a-2o：
R1-R4It is identical or different；
Y、R21、R22And R23It is independently substituted or non-substituted C1-C20Alkane group, substitution or non-take
The C in generation1-C20Silane hydrocarbyl group, substitution or non-substituted C6-C65Aromatic group, substitution or non-substituted C6-C65's
Fragrant silane group, substituted or non-substituted C6-C65Heteroaromatic group or substituted or non-substituted C6-C65Condensing polyaromatic hydrocarbon
Group, * represent the position of substitution, and p represents substitution number, and scope is integer 1-7.
Specifically, Y, R21、R22Or R23In：
C1-C20Alkane group be methyl, ethyl, propyl, isopropyl, butyl, isobutyl group or tertiary butyl；
C1-C20Silane hydrocarbyl group be first silicon substrate, second silicon substrate, the third silicon substrate, isopropyl silicon substrate, fourth silicon substrate, isobutyl silicon substrate or uncle
Fourth silicon substrate；
C6-C65Aromatic group include at least an aromatic rings, condense or be connected by singly-bound between aromatic rings, such as benzene
Base, 1- naphthalenes, 2- naphthalenes, 3,5- diphenyl phenyl etc.；
C6-C65Miscellaneous aromatic rings include at least a five-ring heterocycles or hexa-member heterocycle, five-ring heterocycles or hexa-member heterocycle point
At least do not condense or be connected by singly-bound between heterocycle, such as thienyl group, benzene containing any one in nitrogen, oxygen, phosphorus or sulphur
Bithiophene group, pyridine groups, pyrrole group, oxazole group, thiazolyl group, thiadiazoles group, triazine group, diphenyl phosphorus oxygen
Group, imidazole group, to phenyl benzimidazole groups group, phenyl benzimidazole groups group, carbazole group, indolyl radical, quinolyl
Group, isoquinolin group.
Further：
C1-C20Alkane group substituent group be deuterium, halogen, hydroxyl, nitro, cyano, amido, amidino groups or carbonyl acyl group；
C1-C20Silane hydrocarbyl group substituent group be deuterium, halogen, hydroxyl, nitro, cyano, amido, amidino groups or carbonyl acyl group；
Substituted C6-C65Aromatic group include at least one by methyl, ethyl, propyl, isopropyl, butyl, isobutyl group,
Tertiary butyl, first silicon substrate, second silicon substrate, the third silicon substrate, isopropyl silicon substrate, fourth silicon substrate, isobutyl silicon substrate or the aromatic rings of tertiary fourth silicon substrate substitution, such as
C1-C10 alkyl substituent groups (toluene, ethylo benzene, o-, m-, p- cumenyl, methyl naphthalene), halides (o-, m-, p- fluorine
Benzene is fluorinated naphthalene, trifluoromethylbenzene), cyano object (cyano benzene, cyano naphthalene, cyanobiphenyl), C1-C10 alkyl-substituted biphenyls groups,
C1-C10 alkoxy substituted biphenyl groups, C1-C10 alkyl-substituted naphthaline groups, C1-C10 alkoxy substituted naphthyls group；
Non-substituted C6-C65Miscellaneous aromatic group include at least one by methyl, ethyl, propyl, isopropyl, butyl, different
Butyl, tertiary butyl, first silicon substrate, second silicon substrate, the third silicon substrate, isopropyl silicon substrate, fourth silicon substrate, isobutyl silicon substrate or the heteroaryl of tertiary fourth silicon substrate substitution
Fragrant ring.
Sila condensed ring analog derivative provided by the present invention includes but not limited to following preferred compound：
The present invention also provides a kind of electroluminescent device, including organic light emission a pair of electrodes and setting between the electrodes
Medium, the organic light emitting medium at least contain a kind of sila condensed ring analog derivative provided by the present invention.
The present invention also provides the application of above-mentioned sila condensed ring analog derivative, as the electricity in organic electroluminescence device
Sub- transmission material and/or light emitting host material.
The derivative of sila condensed ring class provided by the present invention forms stronger covalent as electron transfer layer, silicon with halogen
Key has stronger drawing electronic action, and sila heptatomic ring can retain fragrant ring property, while the sp3 hydridization formation of silicon is non-flat
Face structure can effectively reduce entire planes of molecules accumulation, and with high triplet, triplet exciton be avoided to return, suitable for glimmering
Light shines and phosphorescent emitter system.This quasi-molecule has high electron mobility, can be effectively matched the material of high hole mobility,
Equilbrium carrier can be widely applied in organic light emitting diode, and obtain good effect, be that one kind has very big business
The new material of value.
Description of the drawings
Fig. 1 is the structure diagram of device in embodiment.
Fig. 2 is the electron mobility of compound 1,10,12,14,22.
Fig. 3 is the luminescent spectrum figure of device 1,2,12.
Fig. 4 is current efficiency-current density characteristics graph of device 1,2,12.
Specific embodiment
The principles and features of the present invention are described below, and illustrated embodiment is served only for explaining the present invention, is not intended to
Limit the scope of the present invention.
Embodiment 1：The synthesis of compound 1
Addition 50ml tetrahydrofurans in 100ml flasks, (2- bromophenyls) quadrosilan 1.5g, silver fluoride 0.5g, at room temperature
Stir 3 it is small when, after filtering, rotate solvent, n-hexane is recrystallized to give intermediate 1a1.6g.
Under nitrogen protection by 1a (1.6g), 2 hydroxy naphthalene boric acid (0.8g), tetra-triphenylphosphine palladium (0.1g), toluene
(50ml), ethyl alcohol (20ml) and wet chemical (20ml, 2M) are put into 200ml three neck round bottom flask and are stirred, mixture
Stream of nitrogen gas protection under be heated to 90 DEG C reaction 12 it is small when.Room temperature is naturally cooled to after completion of the reaction, is extracted with dichloromethane
Reaction solution, washing, drying, rotates solvent, and column chromatography obtains product 1b 1.5g.
50ml dichloromethane is added in 100ml flasks, 0.1ml trifluoro second is slowly added dropwise under ice bath in intermediate 1b 1.5g
Acid, when stirring 3 is small at room temperature, thin-layer chromatography monitoring reaction process after reactant disappears, adds in aqueous sodium carbonate, uses dichloro
Methane extracts reaction solution, and washing, drying rotate solvent, and column chromatography obtains 1 1.0g. of product1H-NMR:(DMSO-d6,
400MHz):δ (ppm) 8.55 (1H), 8.10 (1H), 8.08 (1H), 8.01 (1H), 7.89 (2H), 7.61 (2H), 7.55 (3H),
7.52(2H),7.46(2H),7.37(2H),7.33(2H),7.11(2H),MS(APCI)(m/z):[M+H+]calcd,
403.53；found,403.53.
Embodiment 2：The synthesis of compound 10
Add in 30ml anhydrous tetrahydro furans in 100ml flasks, diphenyl chlorosilane 3.5g adds in the positive fourths of 2.5M at -110 DEG C
Base lithium 6.5ml, reaction after ten minutes, are added dropwise the tetrahydrofuran solution 20ml of the bromo- 2- iodine naphthalenes (5.35g) of 1-, react 30 points
Zhong Hou, when stirring 3 is small at room temperature, vacuum distillation obtains intermediate 10a 2.6g.
50ml tetrahydrofurans are added in 100ml flasks, it is small to stir 3 at room temperature by intermediate 10a 1.5g, silver fluoride 0.5g
When, after filtering, solvent is rotated, n-hexane is recrystallized to give intermediate 10b 1.4g.
Under nitrogen protection by 10b (1.4g), 2 hydroxy naphthalene boric acid (0.88g), tetra-triphenylphosphine palladium (0.1g), toluene
(40ml), ethyl alcohol (20ml) and wet chemical (40ml, 2M) are put into 200ml three neck round bottom flask and are stirred, mixture
Stream of nitrogen gas protection under be heated to 95 DEG C reaction 12 it is small when.Room temperature is naturally cooled to after completion of the reaction, is extracted with dichloromethane
Reaction solution, washing, anhydrous sodium sulfate drying, rotates solvent, column chromatography obtains product 10c 1.1g.
50ml dichloromethane is added in 100ml flasks, 0.1ml trifluoro second is slowly added dropwise under ice bath in intermediate 10c 1.1g
Acid, when stirring 3 is small at room temperature, thin-layer chromatography monitoring reaction process after reactant disappears, adds in aqueous sodium carbonate, uses dichloro
Methane extracts reaction solution, and washing, drying rotate solvent, and column chromatography obtains 10 0.5g of product,1H-NMR:(DMSO-d6,
400MHz):δ(ppm)8.55(2H),8.14(1H),8.10(1H),8.08(2H),8.01(2H),7.89(1H),7.66(1H),
7.61(1H),7.55(5H),7.52(1H),7.46(2H),7.37(2H),7.33(1H).MS(APCI)(m/z):[M+H+]
calcd,453.59；found,453.49.
Embodiment 3：The synthesis of compound 12
Under nitrogen protection by 10b (1.4g), 2 hydroxy naphthalene boric acid (0.88g), tetra-triphenylphosphine palladium (0.1g), toluene
(40ml), ethyl alcohol (20ml) and wet chemical (40ml, 2M) are put into 200ml three neck round bottom flask and are stirred, mixture
Stream of nitrogen gas protection under be heated to 95 DEG C reaction 12 it is small when.Room temperature is naturally cooled to after completion of the reaction, is extracted with dichloromethane
Reaction solution, washing, anhydrous sodium sulfate drying, rotates solvent, column chromatography obtains product 12c 1.0g.
50ml dichloromethane is added in 100ml flasks, 0.1ml trifluoro second is slowly added dropwise under ice bath in intermediate 10c 1.0g
Acid, when stirring 3 is small at room temperature, thin-layer chromatography monitoring reaction process after reactant disappears, adds in aqueous sodium carbonate, uses dichloro
Methane extracts reaction solution, and washing, drying rotate solvent, and column chromatography obtains 10 0.4g of product, chemical combination is synthesized by suzuki reaction
Object 12,1H-NMR:(DMSO-d6,400MHz):δ(ppm)8.55(1H),8.40(2H),8.14(1H),8.100(1H),8.00
(2H),7.89(1H),7.66(1H),7.61(1H),7.59(2H),7.55(3H),7.52(1H),7.46(2H),7.37(2H),
7.33(1H).MS(APCI)(m/z):[M+H+]calcd,453.59；found,453.51.
Embodiment 4：The synthesis of compound 14
Add in 30ml anhydrous tetrahydro furans in 100ml flasks, diphenyl chlorosilane 3.5g adds in the positive fourths of 2.5M at -110 DEG C
Base lithium 6.5ml, reaction after ten minutes, are added dropwise the tetrahydrofuran solution 20ml of the bromo- 3- iodine naphthalenes (5.35g) of 2-, react 30 points
Zhong Hou, when stirring 3 is small at room temperature, vacuum distillation obtains intermediate 14a 3.0g.
50ml tetrahydrofurans are added in 100ml flasks, it is small to stir 3 at room temperature by intermediate 14a 3.0g, silver fluoride 1.0g
When, after filtering, solvent is rotated, n-hexane is recrystallized to give intermediate 14b 2.8g.
Under nitrogen protection by 14b (2.8g), 2 hydroxy naphthalene boric acid (1.8g), tetra-triphenylphosphine palladium (0.1g), toluene
(50ml), ethyl alcohol (25ml) and wet chemical (50ml, 2M) are put into 200ml three neck round bottom flask and are stirred, mixture
Stream of nitrogen gas protection under be heated to 95 DEG C reaction 12 it is small when.Room temperature is naturally cooled to after completion of the reaction, is extracted with dichloromethane
Reaction solution, washing, anhydrous sodium sulfate drying, rotates solvent, column chromatography obtains product 14c 2.1g.
50ml dichloromethane is added in 100ml flasks, 0.2ml trifluoro second is slowly added dropwise under ice bath in intermediate 14c 2.1g
Acid, when stirring 3 is small at room temperature, thin-layer chromatography monitoring reaction process after reactant disappears, adds in aqueous sodium carbonate, uses dichloro
Methane extracts reaction solution, and washing, drying rotate solvent, and column chromatography obtains 14 0.6g of product,1H-NMR:(DMSO-d6,
400MHz):δ(ppm)8.55(1H),8.44(1H),8.10(1H),8.08(1H),8.01(2H),8.00(2H),7.89(1H),
7.61(1H),7.59(2H),7.55(3H),7.52(1H),7.46(2H),7.37(2H),7.33(1H).MS(APCI)(m/z):
[M+H+]calcd,453.59；found,453.52.
Embodiment 5：The synthesis of compound 17
The anhydrous second diether of 30ml is added in 100ml flasks, diphenyl dichlorosilane 3.5g adds in the examination of 2- naphthalenes form under ice bath
Agent 4.8g, after reacting 30 minutes, when room temperature reaction 3 is small, distillation obtains 17a.
Add in 30ml anhydrous tetrahydro furans in 100ml flasks, intermediate 17a 2.7g add in 2.5M normal-butyls at -110 DEG C
Lithium 4.5ml, reaction after ten minutes, are added dropwise the tetrahydrofuran solution 20ml of the bromo- 3- iodine naphthalenes (3.7g) of 2-, react 30 minutes
Afterwards, when stirring 3 is small at room temperature, vacuum distillation obtains 17b1.0g.
50ml tetrahydrofurans are added in 100ml flasks, it is small to stir 3 at room temperature by intermediate 17b 1.0g, silver fluoride 0.5g
When, after filtering, solvent is rotated, n-hexane is recrystallized to give intermediate 17c 0.8g.
Under nitrogen protection by 17c (0.8g), 2- hydroxyls phenyl boric acid (0.5g), tetra-triphenylphosphine palladium (0.1g), toluene
(25ml), ethyl alcohol (12ml) and wet chemical (25ml, 2M) are put into 100ml three neck round bottom flask and are stirred, mixture
Stream of nitrogen gas protection under be heated to 95 DEG C reaction 12 it is small when.Room temperature is naturally cooled to after completion of the reaction, is extracted with dichloromethane
Reaction solution, washing, anhydrous sodium sulfate drying, rotates solvent, column chromatography obtains product 17d 0.5g.
50ml dichloromethane is added in 100ml flasks, 0.1ml trifluoro second is slowly added dropwise under ice bath in intermediate 17d 0.5g
Acid, when stirring 3 is small at room temperature, thin-layer chromatography monitoring reaction process after reactant disappears, adds in aqueous sodium carbonate, uses dichloro
Methane extracts reaction solution, and washing, drying rotate solvent, and column chromatography obtains 17 0.2g of product,1H-NMR:(DMSO-d6,
400MHz):δ(ppm)8.44(2H),8.01(2H),8.00(4H),7.85(2H),7.59(4H),7.55(1H),7.47(2H),
7.46(2H),7.37(2H).MS(APCI)(m/z):[M+H+]calcd,453.59；found,453.54.
Embodiment 6：The synthesis of compound 22
The anhydrous second diether of 30ml is added in 100ml flasks, diphenyl dichlorosilane 3.5g adds in the examination of 1- naphthalenes form under ice bath
Agent 4.8g, after reacting 30 minutes, when room temperature reaction 3 is small, distillation obtains 22a.
Add in 30ml anhydrous tetrahydro furans in 100ml flasks, intermediate 22a 2.7g add in 2.5M normal-butyls at -110 DEG C
Lithium 4.5ml, after ten minutes, the tetrahydrofuran solution 20ml of 1 iodo- 2- bromonaphthalenes (3.7g) is added dropwise in reaction, after reacting 30 minutes,
When stirring 3 is small at room temperature, vacuum distillation obtains 22b1.5g.
50ml tetrahydrofurans are added in 100ml flasks, it is small to stir 3 at room temperature by intermediate 22b 1.5g, silver fluoride 0.75g
When, after filtering, solvent is rotated, n-hexane is recrystallized to give intermediate 22c 0.6g.
Under nitrogen protection by 12c (0.6g), 2- hydroxyls phenyl boric acid (0.3g), tetra-triphenylphosphine palladium (0.05g), toluene
(25ml), ethyl alcohol (12ml) and wet chemical (25ml, 2M) are put into 100ml three neck round bottom flask and are stirred, mixture
Stream of nitrogen gas protection under be heated to 95 DEG C reaction 12 it is small when.Room temperature is naturally cooled to after completion of the reaction, is extracted with dichloromethane
Reaction solution, washing, anhydrous sodium sulfate drying, rotates solvent, column chromatography obtains product 22d 0.4g.
50ml dichloromethane is added in 100ml flasks, 0.1ml trifluoro second is slowly added dropwise under ice bath in intermediate 22d 0.4g
Acid, when stirring 3 is small at room temperature, thin-layer chromatography monitoring reaction process after reactant disappears, adds in aqueous sodium carbonate, uses dichloro
Methane extracts reaction solution, and washing, drying rotate solvent, and column chromatography obtains 22 0.2g of product,1H-NMR:(DMSO-d6,
400MHz):δ(ppm)8.55(1H),8.18(1H),8.14(1H),7.89(1H),7.87(3H),7.85(2H),7.66(1H),
7.65(1H),7.61(1H),7.60(1H),7.55(4H),7.52(1H),7.47(2H),7.33(1H).MS(APCI)(m/z):
[M+H+]calcd,453.59；found,453.54.
Embodiment 7：The preparation of device 1
This example illustrates the performance verification for the electroluminescent device that compound 1 is prepared as electron transport material.
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then when vacuum drying 2 is small
(105 DEG C), then ITO (tin indium oxide) glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to
Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation
The hole-injecting material of 80nm thickness is then deposited in molybdenum trioxide:4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyls) aniline]
(TAPC), the material 1 of vacuum evaporation last layer 12nm, 3- bis- (9- carbazoles) benzene are then continued through on this hole transmission layer
(mcp):Three (2- phenylpyridines) close iridium (Ir (ppy) 3), are finally deposited the compound 1 of one layer of 20nm again, the LiF of 10nm thickness with
The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device,
The i.e. available bright uniform green light sent from ITO (tin indium oxide) layer, maximum current efficiency are 125.9cd/A.This experiment
Device architecture is：ITO (tin indium oxide)/TAPC (60nm)/mcp:3 6%1 (12nm)/1 (20nm) of Ir (ppy)/LiF (1nm)/
Al(100nm)。
Embodiment 8：The preparation of device 2
This example illustrates the performance verification for the electroluminescent device that compound 10 is prepared as electron transport material.
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then when vacuum drying 2 is small
(105 DEG C), then ITO (tin indium oxide) glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to
Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation
The hole-injecting material of 80nm thickness is then deposited in molybdenum trioxide:4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyls) aniline]
(TAPC), the material 1 of vacuum evaporation last layer 12nm, 3- bis- (9- carbazoles) benzene are then continued through on this hole transmission layer
(mcp):Three (2- phenylpyridines) close iridium (Ir (ppy) 3), are finally deposited the compound 10 of one layer of 20nm again, the LiF of 10nm thickness with
The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device,
The i.e. available bright uniform green light sent from ITO (tin indium oxide) layer, maximum current efficiency are 132.2cd/A.This experiment
Device architecture is：ITO (tin indium oxide)/TAPC (60nm)/mcp:3 6% (12nm)/10 (20nm) of Ir (ppy)/LiF (1nm)/
Al(100nm)。
Embodiment 9：The preparation of device 12
This example illustrates the performance verification for the electroluminescent device that compound 12 is prepared as electron transport material.
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then when vacuum drying 2 is small
(105 DEG C), then ITO (tin indium oxide) glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to
Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation
The hole-injecting material of 80nm thickness is then deposited in molybdenum trioxide:4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyls) aniline]
(TAPC), the material 1 of vacuum evaporation last layer 12nm, 3- bis- (9- carbazoles) benzene are then continued through on this hole transmission layer
(mcp):Three (2- phenylpyridines) close iridium (Ir (ppy) 3), are finally deposited the compound 12 of one layer of 20nm again, the LiF of 10nm thickness with
The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device,
The i.e. available bright uniform green light sent from ITO (tin indium oxide) layer, maximum current efficiency are 117.3cd/A.This experiment
Device architecture is：ITO (tin indium oxide)/TAPC (60nm)/mcp:3 6% (12nm)/12 (20nm) of Ir (ppy)/LiF (1nm)/
Al(100nm)。
Embodiment 10：The preparation of device 14
This example illustrates the performance verification for the electroluminescent device that compound 14 is prepared as electron transport material.
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then when vacuum drying 2 is small
(105 DEG C), then ITO (tin indium oxide) glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to
Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation
The hole-injecting material of 80nm thickness is then deposited in molybdenum trioxide:4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyls) aniline]
(TAPC), the material 1 of vacuum evaporation last layer 12nm, 3- bis- (9- carbazoles) benzene are then continued through on this hole transmission layer
(mcp):Three (2- phenylpyridines) close iridium (Ir (ppy) 3), are finally deposited the compound 14 of one layer of 20nm again, the LiF of 10nm thickness with
The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device,
The i.e. available bright uniform green light sent from ITO (tin indium oxide) layer, maximum current efficiency are 107.3cd/A.This experiment
Device architecture is：ITO (tin indium oxide)/TAPC (60nm)/mcp:3 6% (12nm)/14 (20nm) of Ir (ppy)/LiF (1nm)/
Al(100nm)。
Embodiment 11：The preparation of device 17
This example illustrates the performance verification for the electroluminescent device that compound 17 is prepared as electron transport material.
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then when vacuum drying 2 is small
(105 DEG C), then ITO (tin indium oxide) glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to
Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation
The hole-injecting material of 80nm thickness is then deposited in molybdenum trioxide:4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyls) aniline]
(TAPC), the material 1 of vacuum evaporation last layer 12nm, 3- bis- (9- carbazoles) benzene are then continued through on this hole transmission layer
(mcp):Three (2- phenylpyridines) close iridium (Ir (ppy) 3), are finally deposited the compound 17 of one layer of 20nm again, the LiF of 10nm thickness with
The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device,
The i.e. available bright uniform green light sent from ITO (tin indium oxide) layer, maximum current efficiency are 107.5cd/A.This experiment
Device architecture is：ITO (tin indium oxide)/TAPC (60nm)/mcp:3 6% (12nm)/17 (20nm) of Ir (ppy)/LiF (1nm)/
Al(100nm)。
Embodiment 12：The preparation of device 22
This example illustrates the performance verification for the electroluminescent device that compound 22 is prepared as electron transport material.
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then when vacuum drying 2 is small
(105 DEG C), then ITO (tin indium oxide) glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to
Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation
The hole-injecting material of 80nm thickness is then deposited in molybdenum trioxide:4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyls) aniline]
(TAPC), the material 1 of vacuum evaporation last layer 12nm, 3- bis- (9- carbazoles) benzene are then continued through on this hole transmission layer
(mcp):Three (2- phenylpyridines) close iridium (Ir (ppy) 3), are finally deposited the compound 22 of one layer of 20nm again, the LiF of 10nm thickness with
The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device,
The i.e. available bright uniform green light sent from ITO (tin indium oxide) layer, maximum current efficiency are 103.5cd/A.This experiment
Device architecture is：ITO (tin indium oxide)/TAPC (60nm)/mcp:3 6% (12nm)/22 (20nm) of Ir (ppy)/LiF (1nm)/
Al(100nm)。
Application examples
As shown in figure 3, it is the luminescent spectrum figure of device 1,2,12；As shown in figure 4, current efficiency-electricity of device 1,2,12
Current density performance diagram.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all the present invention spirit and
Within principle, any modifications, equivalent replacements and improvements are made should all be included in the protection scope of the present invention.
Claims (10)
1. sila condensed ring analog derivative, which is characterized in that with the general structure shown in formula (Ia) or formula (Ib)：
Wherein：
Ar1-Ar4Phenyl or naphthyl is independently selected from, also, at least one is naphthalene；
R1-R4It is independently selected from substituted or unsubstituted C1-C20Alkane group, substitution or unsubstituted C1-
C20Silane hydrocarbyl group, substitution or unsubstituted C6-C65Aromatic group, substitution or unsubstituted C6-C65Virtue
Fragrant silane group, substitution or unsubstituted C5-C65Heterocyclic group, substitution or unsubstituted C6-C65Polycyclic group
Group, substitution or unsubstituted C6-C65Arylene group or substitution or unsubstituted C6-C65Sub- aromatic heterocycle
Group, R1-R4Identical or different, X is halogen F, Cl, Br or I.
2. sila condensed ring analog derivative according to claim 1, which is characterized in that there is the structure shown in formula (Ib) to lead to
Formula, wherein：
C1-C20Alkane group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C1-C20Silane hydrocarbyl group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C6-C65Aromatic group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C6-C65Fragrant silane group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C5-C65Heterocyclic group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C6-C65Polycyclic moiety substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C6-C65Arylene group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl group；
C6-C65Sub- aromatic heterocycle group substituent group be selected from hydrogen, deuterium, halogen atom, cyano, nitro, amidino groups, hydroxyl or carbonyl acyl
Base；
R1-R4It is identical or different；
X is halogen F, Cl, Br or I.
3. sila condensed ring analog derivative according to claim 2, it is characterised in that：
C5-C65Heterocyclic group be C5-C65Heteroaromatic group；
C6-C65Polycyclic moiety be C6-C65Condensing polyaromatic hydrocarbon group.
4. sila condensed ring analog derivative according to claim 1, which is characterized in that as follows：
5. sila condensed ring analog derivative according to claim 1, it is characterised in that：
R1-R4It is independently selected from the structure shown in general formula 2a-2o：
R1-R4It is identical
It is or different；
Y、R21、R22And R23It is independently substituted or non-substituted C1-C20Alkane group, substitution or it is non-substituted
C1-C20Silane hydrocarbyl group, substitution or non-substituted C6-C65Aromatic group, substitution or non-substituted C6-C65Fragrance
Silane group, substituted or non-substituted C6-C65Heteroaromatic group or substituted or non-substituted C6-C65Condensing polyaromatic hydrocarbon base
Group, * represent the position of substitution, and p represents substitution number, and scope is integer 1-7.
6. sila condensed ring analog derivative according to claim 5, which is characterized in that Y, R21、R22Or R23In：
C1-C20Alkane group be methyl, ethyl, propyl, isopropyl, butyl, isobutyl group or tertiary butyl；
C1-C20Silane hydrocarbyl group be first silicon substrate, second silicon substrate, the third silicon substrate, isopropyl silicon substrate, fourth silicon substrate, isobutyl silicon substrate or tertiary fourth silicon
Base；
C6-C65Aromatic group include at least an aromatic rings, condense or be connected by singly-bound between aromatic rings；
C6-C65Miscellaneous aromatic rings include at least a five-ring heterocycles or hexa-member heterocycle, five-ring heterocycles or hexa-member heterocycle are respectively extremely
Less containing any one in nitrogen, oxygen, phosphorus or sulphur, condense or be connected by singly-bound between heterocycle.
7. sila condensed ring analog derivative according to claim 6, it is characterised in that：
C1-C20Alkane group substituent group be deuterium, halogen, hydroxyl, nitro, cyano, amido, amidino groups or carbonyl acyl group；
C1-C20Silane hydrocarbyl group substituent group be deuterium, halogen, hydroxyl, nitro, cyano, amido, amidino groups or carbonyl acyl group；
Substituted C6-C65Aromatic group include at least one by methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, tertiary fourth
Base, first silicon substrate, second silicon substrate, the third silicon substrate, isopropyl silicon substrate, fourth silicon substrate, isobutyl silicon substrate or the aromatic rings of tertiary fourth silicon substrate substitution；
Non-substituted C6-C65Miscellaneous aromatic group include at least one by methyl, ethyl, propyl, isopropyl, butyl, isobutyl group,
Tertiary butyl, first silicon substrate, second silicon substrate, the third silicon substrate, isopropyl silicon substrate, fourth silicon substrate, isobutyl silicon substrate or the miscellaneous aromatic rings of tertiary fourth silicon substrate substitution.
8. sila condensed ring analog derivative according to any one of claims 1 to 7, which is characterized in that as follows：
9. a kind of electroluminescent device, including organic light emitting medium a pair of electrodes and setting between the electrodes, it is characterised in that：
The organic light emitting medium is at least containing a kind of sila condensed ring analog derivative provided selected from claim 1 to 8.
10. a kind of application of sila condensed ring analog derivative according to any one of claims 1 to 8, it is characterised in that：As having
Electron transport material and/or light emitting host material in organic electroluminescence devices.
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| US11342517B2 (en) | 2018-12-29 | 2022-05-24 | Ningbo Lumilan Advanced Materials Co., Ltd. | Dibenzoheterocyclic compound and preparation method and application thereof |
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