TWI808518B - 一種苯並菲衍生物及其應用 - Google Patents
一種苯並菲衍生物及其應用 Download PDFInfo
- Publication number
- TWI808518B TWI808518B TW110140148A TW110140148A TWI808518B TW I808518 B TWI808518 B TW I808518B TW 110140148 A TW110140148 A TW 110140148A TW 110140148 A TW110140148 A TW 110140148A TW I808518 B TWI808518 B TW I808518B
- Authority
- TW
- Taiwan
- Prior art keywords
- triphenylene derivative
- organic electroluminescent
- layer
- organic
- atoms
- Prior art date
Links
- 125000005580 triphenylene group Chemical group 0.000 title claims abstract description 43
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 94
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004431 deuterium atom Chemical group 0.000 claims description 13
- 239000002019 doping agent Substances 0.000 claims description 13
- 125000002560 nitrile group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 46
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 6
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 abstract description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 3
- 238000004020 luminiscence type Methods 0.000 abstract description 3
- OFINUYJHOYCVJI-UHFFFAOYSA-N 22-thiahexacyclo[12.11.0.02,7.08,13.015,23.016,21]pentacosa-1(14),2,4,6,8,10,12,15(23),16,18,20,24-dodecaene Chemical group C1=CC=C2C3=C4C5=CC=CC=C5SC4=CC=C3C3=CC=CC=C3C2=C1 OFINUYJHOYCVJI-UHFFFAOYSA-N 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- 238000002360 preparation method Methods 0.000 description 33
- 238000012360 testing method Methods 0.000 description 31
- 239000012074 organic phase Substances 0.000 description 28
- 238000000034 method Methods 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- -1 methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy Chemical group 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940095102 methyl benzoate Drugs 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IGZZMBOJOUYRAV-UHFFFAOYSA-N CC1=CC=CC=C1.C(C)(C)(C)[P] Chemical compound CC1=CC=CC=C1.C(C)(C)(C)[P] IGZZMBOJOUYRAV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000005092 sublimation method Methods 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 2
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 1
- LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-UHFFFAOYSA-N 0.000 description 1
- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 1
- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 description 1
- DFUGYZQSDFQVPU-UHFFFAOYSA-N 1-benzofuran-3-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=COC2=C1 DFUGYZQSDFQVPU-UHFFFAOYSA-N 0.000 description 1
- QVANIYYVZZLQJP-UHFFFAOYSA-N 1-benzothiophen-3-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CSC2=C1 QVANIYYVZZLQJP-UHFFFAOYSA-N 0.000 description 1
- RERATEUBWLKDFE-UHFFFAOYSA-N 1-methoxy-2-[2-(2-methoxypropoxy)propoxy]propane Chemical compound COCC(C)OCC(C)OCC(C)OC RERATEUBWLKDFE-UHFFFAOYSA-N 0.000 description 1
- JCHJBEZBHANKGA-UHFFFAOYSA-N 1-methoxy-3,5-dimethylbenzene Chemical compound COC1=CC(C)=CC(C)=C1 JCHJBEZBHANKGA-UHFFFAOYSA-N 0.000 description 1
- WCOYPFBMFKXWBM-UHFFFAOYSA-N 1-methyl-2-phenoxybenzene Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1 WCOYPFBMFKXWBM-UHFFFAOYSA-N 0.000 description 1
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 1
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 description 1
- FCTIZUUFUMDWEH-UHFFFAOYSA-N 1h-imidazo[4,5-b]quinoxaline Chemical compound C1=CC=C2N=C(NC=N3)C3=NC2=C1 FCTIZUUFUMDWEH-UHFFFAOYSA-N 0.000 description 1
- VBMIZCKXRRAXBK-UHFFFAOYSA-N 1h-inden-2-ylboronic acid Chemical class C1=CC=C2CC(B(O)O)=CC2=C1 VBMIZCKXRRAXBK-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- PFRPMHBYYJIARU-UHFFFAOYSA-N 2,3-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CC=C2N=NC3=CC=CC4=CC=C1C2=C43 PFRPMHBYYJIARU-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- BWWOQQFGIMERAZ-UHFFFAOYSA-N 2,7-dimethoxyxanthen-9-one Chemical compound C1=C(OC)C=C2C(=O)C3=CC(OC)=CC=C3OC2=C1 BWWOQQFGIMERAZ-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- UKTIFJNXKPQLBF-UHFFFAOYSA-N 3h-inden-1-ylboronic acid Chemical class C1=CC=C2C(B(O)O)=CCC2=C1 UKTIFJNXKPQLBF-UHFFFAOYSA-N 0.000 description 1
- NCSVCMFDHINRJE-UHFFFAOYSA-N 4-[1-(3,4-dimethylphenyl)ethyl]-1,2-dimethylbenzene Chemical compound C=1C=C(C)C(C)=CC=1C(C)C1=CC=C(C)C(C)=C1 NCSVCMFDHINRJE-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- LVUBSVWMOWKPDJ-UHFFFAOYSA-N 4-methoxy-1,2-dimethylbenzene Chemical compound COC1=CC=C(C)C(C)=C1 LVUBSVWMOWKPDJ-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- IUKNPBPXZUWMNO-UHFFFAOYSA-N 5,12-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4,6,8(16),9,11,13-octaene Chemical compound N1=CC=C2C=CC3=NC=CC4=CC=C1C2=C43 IUKNPBPXZUWMNO-UHFFFAOYSA-N 0.000 description 1
- NHWJSCHQRMCCAD-UHFFFAOYSA-N 5,14-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CN=C2C=CC3=NC=CC4=CC=C1C2=C43 NHWJSCHQRMCCAD-UHFFFAOYSA-N 0.000 description 1
- PODJSIAAYWCBDV-UHFFFAOYSA-N 5,6-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaene Chemical compound C1=NN=C2C=CC3=CC=CC4=CC=C1C2=C43 PODJSIAAYWCBDV-UHFFFAOYSA-N 0.000 description 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- ZPIPUFJBRZFYKJ-UHFFFAOYSA-N C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 Chemical compound C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 ZPIPUFJBRZFYKJ-UHFFFAOYSA-N 0.000 description 1
- VEFYQEHKYMAEBW-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)C1=CC=CC=C1.C1C(CCCC1)P Chemical group COC1=C(C(=CC=C1)OC)C1=CC=CC=C1.C1C(CCCC1)P VEFYQEHKYMAEBW-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 101100348848 Mus musculus Notch4 gene Proteins 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- YNCYPMUJDDXIRH-UHFFFAOYSA-N benzo[b]thiophene-2-boronic acid Chemical compound C1=CC=C2SC(B(O)O)=CC2=C1 YNCYPMUJDDXIRH-UHFFFAOYSA-N 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- KBGLLTZFGISMPR-UHFFFAOYSA-N cinnolino[5,4,3-cde]cinnoline Chemical compound C1=CC=C2N=NC3=CC=CC4=NN=C1C2=C43 KBGLLTZFGISMPR-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical group 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- QQTOBDXDQYCGMA-UHFFFAOYSA-N naphtho[2,3-e][1,3]benzoxazole Chemical compound C1=CC=C2C=C3C(N=CO4)=C4C=CC3=CC2=C1 QQTOBDXDQYCGMA-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
-
- 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
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electromagnetism (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本發明涉及一種苯並菲衍生物及其應用,所述的苯並菲衍生物的結構式如式(I)所示。本發明所述的苯並菲衍生物具有吲哚、苯並呋喃、苯並噻吩並苯並菲的稠環結構的新型有機電致發光化合物,是在苯並菲的基礎上增大分子內的電子密度,同時調整取代基團增大分子位阻、減弱分子間的π-π相互作用,提高分子的內量子效率,並且具有與現有的化合物相比更短的發光波長。同時,所述的苯並菲衍生物阻礙有機分子間激-激複合物的生成、增加內部電子密度和穩定性,因此,利用本發明所述的苯並菲衍生物製備有機電致發光器件的效果和壽命明顯提高。
Description
本發明屬於有機電致發光技術領域,具體涉及一種苯並菲衍生物及其應用。
有機電致發光元件所使用的物質大部分為純有機物或有機物與金屬形成絡合物的有機金屬絡合物,根據用途可區分為空穴注入物、空穴輸送物、發光物、電子輸送物、電子注入物等。在此,作為空穴注入物或空穴輸送物主要使用離子化能相對較小的有機物,作為電子注入物或電子輸送物主要使用電負性較大的有機物。此外,作為發光輔助層所使用的物質最好能滿足如下特性。
第一、有機電致發光元件中所使用的物質需較好的熱穩定性,其原因是在有機電致發光元件內部因電荷的遷移而發生焦耳熱,目前,作為空穴輸送層通常所使用的材料的玻璃化溫度低,因此在低溫下驅動時出現因發生結晶化而引起發光效率降低的現象。第二、為了降低驅動電壓,需要與陰極和陽極鄰接的有機物設計成電荷注入勢壘較小,電荷遷移率高。第三、電極和有機層的介面、有機層和有機層的介面上一直存在能量壁壘而不可避免地累積一些電荷,因此需要使用電化學穩定性優異的物質。
發光層由主發光體和摻雜物這兩種物質構成,摻雜物需要量子效率高,與摻雜物相比主發光體需要能隙大而容易發生向摻雜物的能量轉移。用於電視、移動設備等的顯示器根據紅色、綠色、藍色這三原色實現全彩色,發光層分別由紅色主發光體/摻雜物、綠色主發光體/摻雜物以及藍色主發光體/摻雜物構成。目前藍光材料仍然存在發光量子效率低、色純度差的問題。造成這種狀況的主要原因是因為藍光來自於能隙較寬的能級間的躍遷,而寬禁帶的有機化合物在進行分子設計時存在一定的困難,其次藍光材料的體系中存在著較強的π-π鍵相互作用,有著很強的電荷轉移特性,從而使寬頻隙中存在更多的無輻射弛豫通道,加劇了分子之間螢光淬滅,降低了藍光體系的量子產率。因此設計合成綜合性能優良的藍光材料,將成為有機電致發光材料研究的重要課題。
鑒於以上原因,特提出本發明。
為了解決現有技術存在的以上問題,本發明提供了一種苯並菲衍生物及其應用,本發明的所述的苯並菲衍生物應用與有機電致發光材料中,可以提高有機電致發光元件的效率、壽命。
本發明的第一目的,提供了一種苯並菲衍生物,所述的苯並菲衍生物的結構式如式(I)所示:
其中,R1、R2、R3、R4、R5、R6、T1、T2各自獨立地選自氫、氘、具有C1-C40的直鏈烷基、具有C1-C40的直鏈雜烷基、具有C3-C40的支鏈或環狀的烷基、具有C3-C40的支鏈或環狀的雜烷基、具有C2-C40的烯基或炔基、具有5~60個原子的芳族環系或雜芳族環系中的一種,R1、R2、R3、R4、R5、R6、T1、T2中的每個基團可被一個或多個基團R取代;
優選的,T1和T2通過選自O、S、S(=O)、S(=O)2、NR、C(R)2、BR、PR、P(=O)R、Si(R)2的橋連基彼此橋連;
X1、X2如式(II)所示:
其中,G為C(R)2、NR、氧或硫,Z在每次出現時相同或不同,選自CR或N,並且^指示式(I)中的相鄰基團X1、X2;
所述R在每次出現時相同或不同,選自氫原子、氘原子、鹵素原子、腈基、硝基、N(Ar1)2、N(R7)2、C(=O)Ar1、C(=O)R7、P(=O)(Ar1)2、具有
C1-C40的直鏈烷基、具有C1-C40的直鏈雜烷基、具有C3-C40的支鏈或環狀的烷基、具有C3-C40的支鏈或環狀的雜烷基、具有C2-C40的烯基或炔基、具有5至80個、優選5至60個原子的芳族環或雜芳族環系、具有5至60個原子的芳氧基或雜芳氧基中的一種,R中的每個基團可被一個或多個基團R7取代,或這些體系的組合,其中一個或多個非相鄰的-CH2-基團可被R7C=CR7、C≡C、Si(R7)2、Ge(R7)2、Sn(R7)2、C=O、C=S、C=Se、C=NR7、P(=O)(R7)、SO、SO2、NR7、O、S或CONR7代替,並且其中一個或多個氫原子被氘原子、鹵素原子、腈基或硝基代替,其中兩個或更多個相鄰的R可以任選地接合或稠合形成單環或多環的脂族、芳族或雜芳族環系,所述環系可被一個或多個基團R7取代;
R7在每次出現時相同或不同,選自氫原子、氘原子、鹵素原子、腈基、硝基、N(Ar1)2、N(R8)2、C(=O)Ar1、C(=O)R8、P(=O)(Ar1)2、具有C1-C40的直鏈烷基、具有C1-C40的直鏈雜烷基、具有C3-C40的支鏈或環狀的烷基、具有C3-C40的支鏈或環狀的雜烷基、具有C2-C40的烯基或炔基、具有5至60個原子的芳族環或雜芳族環系、具有5至60個原子的芳氧基或雜芳氧基中的一種,R7中的每個基團可被一個或多個基團R8取代,或這些體系的組合,其中一個或多個非相鄰的-CH2-基團可被R8C=CR8、C≡C、Si(R8)2、Ge(R8)2、Sn(R8)2、C=O、C=S、C=Se、C=NR8、P(=O)(R8)、SO、SO2、NR8、O、S或CONR8代替,並且其中一個或多個氫原子可被氘原子、鹵素原子、腈基或硝基代替,其中兩個或更多個相鄰的取代基R可以任選地接合或稠合形成單環或多環的脂族、芳族或雜芳族環系,所述環系可被一個或多個基團R8取代;
Ar1在每次出現時相同或不同,選自具有5~30個原子的芳族或雜芳族環系,所述環系可被一個或多個非芳族基團R8取代;此處鍵合至同一氮
原子或磷原子的兩個基團Ar1也可通過單鍵或選自N(R8)、C(R8)2、氧或硫的橋連基彼此橋連;
R8選自氫原子、氘原子、氟原子、腈基、具有C1-C20的脂族烴基、具有5~30個原子的芳族環或雜芳族環系,其中一個或多個氫原子可被氘原子、鹵素原子、或腈基代替,其中兩個或更多個相鄰的取代基R8可彼此形成單環或多環的脂族、芳族或雜芳族環系。
進一步地,所述R1、R2、R3、R4、R5、R6、T1、T2各自獨立地選自氫、氘、具有C1-C40的烷基、具有C3-C40的支鏈或環狀的烷基、具有5~60個原子的芳族環系或雜芳族環系中一種,R1、R2、R3、R4、R5、R6、T1、T2中的每個基團可被一個或多個基團R取代。
進一步地,所述R在每次出現時相同或不同,選自氫原子、氘原子、鹵素原子、腈基、N(Ar1)2、具有C1-C40的直鏈烷基、具有C1-C40的直鏈雜烷基、具有C3-C40的支鏈或環狀的烷基、具有C3-C40的支鏈或環狀的雜烷基、具有C2-C40的烯基或炔基、具有5至80個、優選5至60個原子的芳族環或雜芳族環系;
Ar1在每次出現時相同或不同,選自具有5~30個原子的芳族或雜芳族環系,所述環系可被一個或多個非芳族基團R8取代;此處鍵合至同一氮原子或磷原子的兩個基團Ar1也可通過單鍵或選自N(R8)、C(R8)2、氧或硫的橋連基彼此橋連;
R8選自氫原子、氘原子、氟原子、腈基、具有C1-C20的脂族烴基、具有5~30個原子的芳族環或雜芳族環系,其中一個或多個氫原子可被氘原子、鹵素原子、或腈基代替,其中兩個或更多個相鄰的取代基R8可彼此形成單環或多環的脂族、芳族或雜芳族環系。
本發明意義上的芳基含有6-60個碳原子,在本發明意義上的雜芳基含有2-60個碳原子和至少一個雜原子,其條件是碳原子和雜原子的總和至少是5;所述雜原子優選選自N、O或S。此處的芳基或雜芳基被認為是指簡單的芳族環,即苯、萘等,或簡單的雜芳族環,如吡啶、嘧啶、噻吩等,或稠合的芳基或雜芳基,如蒽、菲、喹啉、異喹啉等。通過單鍵彼此連接的芳族環,例如聯苯,相反地不被稱為芳基或雜芳基,而是稱為芳族環系。
在本發明意義上的芳族或雜芳族環系旨在被認為是指不必僅含有芳基或雜芳基的體系,而是其中多個芳基或雜芳基還可以由非芳族單元例如C、N、O或S原子連接。因此,例如,和其中兩個或更多個芳基被例如短的烷基連接的體系一樣,諸如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的體系也被認為是指在本發明意義上的芳族環系。
對於本發明意義上的含有1~40個碳原子並且其中單獨的氫原子或-CH2-基團還可被上述基團取代的脂族烴基或者烷基或者烯基或炔基優選被認為是指如下基團:甲基、乙基、正丙基、異丙基、正丁基、異丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、環戊基、正己基、新己基、環己基、正庚基、環庚基、正辛基、環辛基、2-乙基己基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔
基、庚炔基或辛炔基。烷氧基優選具有1-40個碳原子的烷氧基被認為是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、環己氧基、正庚氧基、環庚氧基、正辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。雜烷基優選具有1-40個碳原子的烷基,是指其中單獨的氫原子或-CH2-基團可被氧、硫、鹵素原子取代的基團,被認為是指烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基,特別是指甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、環戊烯氧基、環戊烯硫基、己烯氧基、己烯硫基、環己烯氧基、環己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
一般來說,根據本發明的環烷基、環烯基可為環丙基、環丁基、環戊基、環己基、環丁烯基、環戊烯基、環己烯基、環庚基、環庚烯基,其中一個或多個-CH2-基團可被上述基團代替;此外,一個或多個氫原子還可被氘原子、鹵素原子或腈基代替。
根據本發明的芳族或雜芳族環原子,在每種情況下還可被上述基團R8取代的芳族或雜芳族環系,特別是指衍生自如下物質的基團:苯、萘、蒽、苯並蒽、菲、芘、、苝、熒蒽、並四苯、並五苯、苯並芘、聯苯、偶
苯、三聯苯、三聚苯、芴、螺二芴、二氫菲、二氫芘、四氫芘、順式或反式茚並芴、順式或反式茚並哢唑、順式或反式吲哚並哢唑、三聚茚、異三聚茚、螺三聚茚、螺異三聚茚、呋喃、苯並呋喃、異苯並呋喃、二苯並呋喃、噻吩、苯並噻吩、異苯並噻吩、二苯並噻吩、吡咯、吲哚、異吲哚、哢唑、吡啶、喹啉、異喹啉、吖啶、菲啶、苯並[5,6]喹啉、苯並[6,7]喹啉、苯並[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯並咪唑、萘並咪唑、菲並咪唑、吡啶並咪唑、吡嗪並咪唑、喹喔啉並咪唑、噁唑、苯並噁唑、萘並噁唑、蒽並噁唑、菲並噁唑、異噁唑、1,2-噻唑、1,3-噻唑、苯並噻唑、噠嗪、六氮雜苯並菲、苯並噠嗪、嘧啶、苯並嘧啶、喹喔啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮雜芘、4,5-二氮雜芘,4,5,9,10-四氮雜苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、熒紅環、萘啶、氮雜哢唑、苯並哢啉、哢啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯並三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯並噻二唑或者衍生自這些體系的組合的基團。
進一步地,所述的苯並菲衍生物的結構主要包括CJHB271~CJHB480,其中G選自氧、硫、CH2、C(CH3)2、C(C6H5)2、N-CH3、N-C2H5、N-C6H5中的一種:
本發明的第二目的,提供了一種所述的苯並菲衍生物在有機電致發光材料中的應用。
進一步地,所述的有機電致發光材料為有機電致發光元件用材料、有機場效應電晶體用材料或有機薄膜太陽電池用材料。
有機電致發光材料可以單獨使用本發明的苯並菲衍生物構成,也可以同時含有其他化合物。
本發明的第三目的,提供了一種有機電致發光裝置,所述的有機電致發光裝置包括第一電極、第二電極和置於所述第一電極和第二電極之間的至少一層有機層,至少一層有機層包含所述的苯並菲衍生物。
所述有機電致發光裝置包含陰極、陽極和至少一個發光層。除了這些層之外,它還可以包含其它的層,例如在每種情況下,包含一個或多個空穴注入層、空穴傳輸層、空穴阻擋層、電子傳輸層、電子注入層、激子阻擋層、電子阻擋層和/或電荷產生層。具有例如激子阻擋功能的中間層同樣可引入兩個發光層之間。然而,應當指出,這些層中的每個並非必須都存在。此處所述有機電致發光裝置可包含一個發光層,或者它可包含多個發光層。即,將能夠發光的多種發光化合物用於所述發光層中。特別優選具有三個發光層的體系,其中所述三個層可顯示藍色、綠色和紅色發光。如果存在多於一個的發光層,則根據本發明,這些層中的至少一個層包含本發明的化合物。
進一步地,根據本發明的有機電致發光裝置不包含單獨的空穴注入層和/或空穴傳輸層和/或空穴阻擋層和/或電子傳輸層,即發光層與空穴注入層或陽極直接相鄰,和/或發光層與電子傳輸層或電子注入層或陰極直接相鄰。
在根據本發明的有機電致發光裝置的其它層中,特別是在空穴注入和空穴傳輸層中以及在電子注入和電子傳輸層中,所有材料可以按照根據現有技術通常所使用的方式來使用。本領域普通技術人員因此將能夠在不付出創造性勞動的情況下與根據本發明的發光層組合使用關於有機電致發光元件所知的所有材料。
此外優選如下的有機電致發光裝置,其特徵在於借助于昇華方法施加一個或多個層,其中在真空昇華裝置中在低於10-5Pa、優選低於10-6Pa的初壓下通過氣相沉積來施加所述材料。然而,所述初壓還可能甚至更低,例如低於10-7Pa。
同樣優選如下的有機電致發光器件,其特徵在於借助於有機氣相沉積方法或借助于載氣昇華來施加一個或多個層,其中,在10-5Pa至1Pa之間的壓力下施加所述材料。該方法的特別的例子是有機蒸氣噴印方法,其中所述材料通過噴嘴直接施加,並且因此是結構化的。
此外優選如下的有機電致發光裝置,從溶液中,例如通過旋塗,或借助於任何所希望的印刷方法例如絲網印刷、柔性版印刷、平版印刷、光引發熱成像、熱轉印、噴墨印刷或噴嘴印刷,來產生一個或多個層。可溶性化合物,例如通過適當的取代獲得可溶性化合物。這些方法也特別適於低聚物、樹枝狀大分子和聚合物。此外可行的是混合方法,其中例如從溶液中施加一個或多個層並且通過氣相沉積施加一個或多個另外的層。
這些方法是本領域普通技術人員通常已知的,並且他們可以在不付出創造性勞動的情況下將其應用於包含根據本發明的化合物的有機電致發光元件。
因此,本發明還涉及製造根據本發明的有機電致發光裝置的方法,其特徵在於借助于昇華方法來施加至少一個層,和/或特徵在於借助於有機氣相沉積方法或借助于載氣昇華來施加至少一個層,和/或特徵在於從溶液中通過旋塗或借助於印刷方法來施加至少一個層。
此外,本發明涉及包含至少一種上文指出的本發明的稠環芳香族化合物。如上文關於有機電致發光裝置指出的相同優選情況適用於所述本發明的稠環芳香族化合物。特別是,所述稠環芳香族化合物此外還可優選包含其它化合物。從液相處理根據本發明的稠環芳香族化合物,例如通過旋塗或通過印刷方法進行處理,需要根據本發明的化合物的製劑。這些製劑可以例如是溶液、分散體或乳液。出於這個目的,可優選使用兩種或更多種溶劑的混合物。合適並且優選的溶劑例如是甲苯,苯甲醚,鄰二甲苯、間二甲苯或對二甲苯,苯甲酸甲酯,均三甲苯,萘滿,鄰二甲氧基苯,四氫呋喃,甲基四氫呋喃,四氫吡喃,氯苯,二噁烷,苯氧基甲苯,特別是3-苯氧基甲苯,(-)-葑酮,1,2,3,5-四甲基苯,1,2,4,5-四甲基苯,1-甲基萘,2-甲基苯並噻唑,2-苯氧基乙醇,2-吡咯烷酮,3-甲基苯甲醚,4-甲基苯甲醚,3,4-二甲基苯甲醚,3,5-二甲基苯甲醚,苯乙酮,α-萜品醇,苯並噻唑,苯甲酸丁酯,異丙苯,環己醇,環己酮,環己基苯,十氫化萘,十二烷基苯,苯甲酸乙酯,茚滿,苯甲酸甲酯,1-甲基吡咯烷酮,對甲基異丙基苯,苯乙醚,1,4-二異丙基苯,二苄醚,二乙二醇丁基甲基醚,三乙二醇丁基甲基醚,二乙二醇二丁基醚,三乙二醇二甲基醚,二乙二醇單丁基醚,三丙二醇二甲基醚,四乙二醇二甲基醚,2-異丙基萘,戊苯,己苯,庚苯,辛苯,1,1-雙(3,4-二甲基苯基)乙烷,或這些溶劑的混合物。
進一步地,所述的有機層還包括電子注入層、電子輸送層、空穴阻擋層、電子阻擋層、空穴輸送層、空穴注入層、發光層中的一種。
進一步地,所述的摻雜物與發光主體的質量比為1:99~50:50。
與現有技術相比,本發明的有益效果為:本發明所述的苯並菲衍生物具有吲哚、苯並呋喃、苯並噻吩並苯並菲的稠環結構的新型有機電致發光化合物,是在苯並菲的基礎上增大分子內的電子密度,同時調整取代基團增大分子位阻、減弱分子間的π-π相互作用,提高分子的內量子效率,並且具有與現有的化合物相比更短的發光波長。同時,所述的苯並菲衍生物阻礙有機分子間激-激複合物的生成、增加內部電子密度和穩定性,因此,利用本發明所述的苯並菲衍生物製備有機電致發光器件的效果和壽命明顯提高,此外,所述的苯並菲衍生物改善了對溶液的溶解度而解決以往藍光材料所具有的工序的生產性以及費用的問題,並且在原有的工序中不是其蒸鍍工序,而是在其他溶液工序中也可以用於製備發光層。
1:基板
2:陽極
3:孔穴注入層
4:孔穴傳輸/電子阻擋層
5:發光層
6:孔穴阻擋/電子傳輸層
7:電子注入層
8:陰極
為了更清楚地說明本發明實施例或現有技術中的技術方案,下面將對實施例或現有技術描述中所需要使用的附圖作簡單地介紹,顯而易見地,下面描述中的附圖僅僅是本發明的一些實施例,對於本領域普通技術人員來講,在不付出創造性勞動的前提下,還可以根據這些附圖獲得其他的附圖。
圖1是本發明的有機電致發光裝置的一個底部發光例子的示意圖;
圖2是本發明的有機電致發光裝置的一個頂部發光例子的示意圖。
為使本發明的目的、技術方案和優點更加清楚,下面將對本發明的技術方案進行詳細的描述。顯然,所描述的實施例僅僅是本發明一部分實施例,而不是全部的實施例。基於本發明中的實施例,本領域普通技術人員在沒有做出創造性勞動的前提下所得到的所有其它實施方式,都屬於本發明所保護的範圍。
下述對OLED材料及元件進行性能測試的測試儀器及方法如下:
OLED元件性能檢測條件:
亮度和色度座標:使用光譜掃描器PhotoResearch PR-715測試;
電流密度和起亮電壓:使用數位源表Keithley 2420測試;
功率效率:使用NEWPORT 1931-C測試;
壽命測試:使用LTS-1004AC壽命測試裝置。
實施例1
化合物CJHB271的製備方法,包括如下步驟:
第一步:化合物Int.-1的製備
在氮氣保護下,24.5g(127.0mmol)的對氯溴苯溶於300mL乾燥的四氫呋喃中,用液氮降溫至-78℃,緩慢滴加入56.0mL的2.5M正丁基鋰正己烷溶液,攪拌反應1小時,滴加入19.5g(140.0mmol)的對氯苯腈溶於50mL乾燥四氫呋喃的溶液,升至室溫攪拌反應2小時,加入50mL的飽和氯化銨水溶液,攪拌反應30分鐘,分出有機相,水相用乙酸乙酯萃取,收集有機相乾燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到27.7g白色固體,收率87%。
第二步:化合物Int.-2的製備
在氮氣保護下,12.6g(50.0mmol)第一步製備的Int.-1溶解於200mL的二氯甲烷中,冰水浴降溫到0℃,加入20.0g的四溴化碳和12.5g的亞磷酸三異丙酯,攪拌反應30分鐘,升到室溫反應1小時,滴加入50mL的1N稀鹽酸水溶液,攪拌30分鐘,分出有機相,水相用二氯甲烷萃取,收集有機相,乾
燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到白色固體Int.-2,收率92%。
第三步:化合物Int.-3的製備
取20.0g(50.0mmol)第二步製備的中間體Int.-2與100mL的1,4-二氧六環混合,在氮氣保護下,加入110.0mmol的苯並呋喃-2-硼酸或苯並噻吩-2-硼酸或1-取代吲哚-2-硼酸或1,1-取代的茚-2-硼酸和112.5mg的醋酸鈀催化劑、410.5mg的2-雙環己基膦-2’,6’-二甲氧基聯苯以及80.0mmol的水合磷酸鉀,再加入40mL的水,升溫至60℃攪拌反應12小時,冷卻到室溫,加入100mL的乙酸乙酯和100mL的水,分出有機相,水相再用乙酸乙酯萃取,收集有機相再用飽和鹽水洗,有機相乾燥過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到白色固體Int.-3,收率60~65%。
第四步:化合物Int.-4的製備
20.0mmol第三步製備的中間體Int-3和100mL的氯仿、20mL的硝基甲烷混合,再加入1.6g的無水氯化鐵,加熱回流反應24小時,冷卻到室溫,加入
50mL稀鹽酸水溶液,用二氯甲烷萃取,收集有機相,乾燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到中間體Int.-4,收率55~65%。
第五步:化合物CJHB271的製備
將5.0mmol第四步製備的中間體Int.-4分散在60mL的甲苯中,加入12.0mmol的二苯胺,再加入1.5g(15.0mmol)的叔丁醇鈉、55.0mg(0.05mmol)的Pd2(dba)3CHCl3催化劑和0.1mL的10%叔丁基磷甲苯溶液,升溫至100℃攪拌反應12小時,反應結束後,加入50mL的水,分出有機相,水相用甲苯-THF萃取,收集有機相乾燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,再用二氯甲烷和乙醇重結晶,得到CJHB271,黃色固體。
實驗資料如表1所示:
實施例2
化合物CJHB387的製備方法,包括如下步驟:
第一步:化合物Int.-5的製備
在氮氣保護下,12.8g(50.0mmol)的2,7-二甲氧基氧雜蒽-9-酮溶解於200mL的二氯甲烷中,冰水浴降溫到0℃,加入20.0g的四溴化碳和12.5g的亞磷酸三異丙酯,攪拌反應30分鐘,升到室溫反應1小時,滴加入50mL的1N稀鹽酸水溶液,攪拌30分鐘,分出有機相,水相用二氯甲烷萃取,收集有機
相,乾燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到白色固體Int.-5,收率94%。
第二步:化合物Int.-6的製備
參照實施例1第三步的製備方法,僅將實施例1第三步中的Int.-2替換為中間體Int.-5,製備中間體Int.-6,收率80~90%。
第三步:化合物Int.-7的製備
參照實施例1第四步的製備方法,僅將實施例1第四步中的Int.-3替換為中間體Int.-6,於室溫攪拌反應12小時,製備中間體Int.-7,收率65~75%。
第四步:化合物Int.-8的製備
在氮氣保護下,20.0mmol的中間體Int.-7溶解於120mL乾燥的二氯甲烷中,用液氮降溫至-40℃,滴加入40.0mmol的三溴化硼溶於二氯甲烷的溶液,攪拌反應2小時,升到室溫,滴加入50mL的1N稀鹽酸水溶液,攪拌1小
時,分出有機相,水相用二氯甲烷萃取,有機相乾燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到固體Int.-8,收率90~94%。
第五步:化合物Int.-9的製備
在氮氣保護下,20.0mmol的中間體Int.-8溶解於120mL乾燥的二氯甲烷中,加入60.0mmol的吡啶,用冰水浴降溫至0℃,滴加入48.0mmol的三氟甲基磺酸酐溶於二氯甲烷的溶液,攪拌反應2小時,升到室溫攪拌反應2小時,加入50mL的1N稀鹽酸水溶液,分出有機相,水相用二氯甲烷萃取,有機相乾燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到固體Int.-9,收率92~96%。
第六步:化合物CJHB387的製備
將5.0mmol第五步製備的中間體Int.-9分散在60mL的甲苯中,加入12.0mmol的4,4’-二甲基二苯胺,再加入2.0g(20.0mmol)的叔丁醇鈉、55.0mg(0.05mmol)的Pd2(dba)3CHCl3催化劑和0.1mL的10%叔丁基磷甲苯溶液,升溫至100℃攪拌反應12小時,反應結束後,加入50mL的水,分出有機相,水
相用乙酸乙酯-THF萃取,收集有機相乾燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,再用THF-甲苯重結晶,得到CJHB387,黃色固體。
實驗資料如表2所示。
實施例3
化合物CJHB270~CJHB324、CJHB386、CJHB388~CJHB403的製備:
參照實施例1~2的製備方法,僅將不同的腫胺替換實施例1中第五步的二苯胺或實施例2中第六步的4,4’-二甲基二苯胺,其他實驗參數進行常規調整。
實施例4
化合物CJHB336的製備:
第一步:化合物Int.-11的製備
6.6mmol的中間體Int.-10(參照實施例1的合成方法,僅將第一步中的對氯溴苯替換為溴苯製備中間體Int.-10)分散於100mL乾燥的THF中,在氮氣保護下,用液氮降溫至-78℃,滴加入3.2mL的2.5M叔丁基鋰,攪拌反應1小時,滴加入10.0mmol的硼酸三甲酯,反應1小時後,加入50mL的2N稀鹽酸水溶液,分出有機相,水相用乙酸乙酯萃取,收集有機相乾燥,過濾,濾液減壓濃縮幹,用石油醚洗滌,過濾,得到白色固體,收率65~75%。
第二步:化合物CJHB336的製備
取5.0mmol第一步製備的中間體Int.-10與40mL的甲苯混合,在氮氣保護下,加入4.0mmol的2-氯-4,6-二苯基-1,3,5-三嗪、10.0mmol的無水碳酸鉀和58.0mg的Pd(PPh3)4催化劑,再加入20mL的乙醇和20mL的水,升溫至回流攪拌反應12小時,冷卻到室溫,加入50mL的二氯甲烷和100mL的水,分出有機相,水相再用二氯甲烷萃取,收集有機相再用飽和鹽水洗,有機相乾燥過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到白色固體CJHB336,收率75~86%。
實驗資料如表3所示。
實施例5
化合物CJHB325~CJHB335、CJHB337~CJHB385的製備:
參照實施例4的製備方法,僅將不同的鹵代物替換實施例4中第二步的2-氯-4,6-二苯基-1,3,5-三嗪,其他實驗參數進行常規調整。
實施例6
化合物CJHB413的製備方法,包括如下步驟:
第一步:化合物Int.-13的製備
取22.0g(50.0mmol)的中間體Int.-12(參照實施例2的合成方法製備)與100mL的1,4-二氧六環混合,在氮氣保護下,加入110.0mmol的苯並呋喃-3-硼酸
或苯並噻吩-3-硼酸或1-取代吲哚-3-硼酸或1,1-取代的茚-3-硼酸和112.5mg的醋酸鈀催化劑、410.5mg的2-雙環己基膦-2’,6’-二甲氧基聯苯以及80.0mmol的水合磷酸鉀,再加入40mL的水,升溫至60℃攪拌反應12小時,冷卻到室溫,加入100mL的乙酸乙酯和50mL的水,分出有機相,水相再用乙酸乙酯萃取,收集有機相再用飽和鹽水洗,有機相乾燥過濾,濾液減壓濃縮幹,用矽膠柱分離純化,得到中間體Int.-13,收率70~80%。
第二步:化合物Int.-14的製備
在氮氣保護下,10.5mmol第一步製備的中間體Int.-13溶解於200mL的二氯甲烷中,加入63.0mmol的碘,再加入10mL的環氧丙烷,用254nm的紫外燈照射,攪拌反應12小時,減壓濃縮幹,加入100mL的甲醇分散,過濾,濾餅用矽膠柱分離純化,得到黃色固體中間體Int.-14,收率85~95%。
第三步:化合物Int.-15的製備
參照實施例2第四步的合成方法,僅將實施例2第四步中的中間體Int.-7替換為中間體Int.-13,製備得到中間體Int.-15,收率92~96%。
第四步:化合物Int.-16的製備
參照實施例2第五步的合成方法,僅將實施例2第五步中的中間體Int.-8替換為中間體Int.-15,製備得到中間體Int.-16,收率85~90%。
第五步:化合物CJHB413的製備
將5.0mmol第四步製備的中間體Int.-16分散在60mL的甲苯中,加入12.0mmol的4,4’-二甲基二苯胺,再加入2.0g(20.0mmol)的叔丁醇鈉、55.0mg(0.05mmol)的Pd2(dba)3CHCl3催化劑和0.1mmol的Xanphos,升溫至90℃攪拌反應12小時,反應結束後,加入50mL的水,分出有機相,水相用乙酸乙酯-THF萃取,收集有機相乾燥,過濾,濾液減壓濃縮幹,用矽膠柱分離純化,再用THF-甲苯重結晶,得到CJHB413,黃色固體。
實驗資料如表4所示:
實施例7
化合物CJHB404~CJHB412、CJHB414~CJHB429的製備:
參照實施例6的製備方法,僅將不同的腫胺替換實施例6中第五步的4,4’-二甲基二苯胺,其他實驗參數進行常規調整。
實施例8
化合物CJHB430~CJHB480的製備:
參照實施例4的製備方法,僅將不同的鹵代物替換實施例4中第二步的2-氯-4,6-二苯基-1,3,5-三嗪,其他實驗參數進行常規調整。
試驗例1
如圖1所示,一種OLED元件,所示的OLED元件的製備方法包括如下步驟:
1)將塗布了ITO導電層的玻璃基片在清洗劑中超聲處理30分鐘,在去離子水中沖洗,在丙酮/乙醇混合溶劑中超聲30分鐘,在潔淨的環境下烘烤至完全乾燥,用紫外光清洗機照射10分鐘,並用低能陽離子束轟擊表面。
2)把上述處理好的ITO玻璃基片置於真空腔內,抽真空至1×10-5~9×10-3Pa,在上述陽極層膜上繼續分別蒸鍍化合物DNTPD作為空穴注入層,蒸鍍膜厚為300Å;在上述空穴注入層膜上繼續蒸鍍NPD為空穴傳輸層,蒸鍍膜厚為2200Å;
3)在空穴傳輸層上繼續蒸鍍一層化合物HT202作為電子阻擋層,蒸鍍膜厚為100Å;
4)在電子阻擋層上繼續蒸鍍一層實施例1-8製備的苯並菲衍生物CJHB271~CJHB480中的一種和BH011作為有機發光層,其中,BH011為主體材料和本發明所述的苯並菲衍生物為摻雜材料,所述的的苯並菲衍生物在BH011中的摻雜濃度為1~20%,蒸鍍膜厚為500Å;
5)在上述有機發光層上再繼續蒸鍍一層化合物TPBI作為空穴阻擋層,蒸鍍膜厚為50Å;
6)在上述空穴阻擋層上再繼續蒸鍍一層化合物LiQ和ET205作為器件的電子傳輸層,其中,LiQ和ET205的質量比為1:1,蒸鍍膜厚為200Å;
7)在上述空穴阻擋層上再繼續蒸鍍一層化合物LiF作為器件的電子傳輸層,蒸鍍膜厚為10Å;最後,在上述電子傳輸層之上蒸鍍金屬鋁作為元件的陰極層,蒸鍍膜厚為1500Å。
其中,試驗例1中所使用的化合物結構式如下所示:
試驗樣品1
試驗例1中的苯並菲衍生物為CJHB271-1,其他按照試驗例1的方法製備的發光元件。
試驗樣品2
試驗例1中的苯並菲衍生物為CJHB271-4,其他按照試驗例1的方法製備的發光元件。
試驗樣品3
試驗例1中的苯並菲衍生物為CJHB387-1,其他按照試驗例1的方法製備的發光元件。
試驗樣品4
試驗例1中的苯並菲衍生物為CJHB387-4,其他按照試驗例1的方法製備的發光元件。
試驗樣品5
試驗例1中的苯並菲衍生物為CJHB336-2,其他按照試驗例1的方法製備的發光元件。
試驗樣品6
試驗例1中的苯並菲衍生物為CJHB413-2,其他按照試驗例1的方法製備的發光元件。
試驗樣品7
試驗例1中的苯並菲衍生物為CJHB413-5,其他按照試驗例1的方法製備的發光元件。
對照樣品1
試驗例1中的苯並菲衍生物替換為化合物BD10,其他按照試驗例1的方法製備的發光元件,其中,化合物BD10的結構式如下所示:
將試驗樣品1-7和對照樣品1的發光元件的性能進行檢測,結果如表5所示。
上表5中可以看出,在電流密度為10mA/cm2條件下的驅動電壓、半峰寬FWHM、電流效率以及在亮度為1000cd/m2初始條件下的器件壽命LT90%的資料是針對對照樣品1歸一化。
結論:從性能測試結果表5可以看到,本發明的化合物作為藍光染料獲得了深藍光有機電致發光器件,相較於採用BD10作為藍光摻雜材料的有機電致發光器件,元件的電流效率更高、驅動電壓降低,而且器件初始亮度在1000cd/m2的條件下,器件的LT90%壽命也有了很大的改善。
產業上的應用可能性
本發明的有機電致發光裝置可以在壁掛電視、平板顯示器、照明等的平面發光體、影印機、印表機、液晶顯示器的背光源或計量儀器類等的光源,顯示板、標識燈等中應用。
以上所述,僅為本發明的具體實施方式,但本發明的保護範圍並不局限於此,任何熟悉本技術領域的技術人員在本發明揭露的技術範圍內,可輕易想到變化或替換,都應涵蓋在本發明的保護範圍之內。因此,本發明的保護範圍應以所述權利要求的保護範圍為准。
1:基板
2:陽極
3:孔穴注入層
4:孔穴傳輸/電子阻擋層
5:發光層
6:孔穴阻擋/電子傳輸層
7:電子注入層
8:陰極
Claims (10)
- 一種苯並菲衍生物,其特徵在於,所述的苯並菲衍生物的結構式如式(I)所示:
- 如請求項1所述的苯並菲衍生物,其中,所述R1、R2、R3、R4、R5、R6、T1、T2各自獨立地選自氫、氘、具有C1-C40的烷基、具有C3-C40的支鏈或環狀的烷基、具有5~60個原子的芳族環系或雜芳族環系中一種,R1、R2、R3、R4、R5、R6、T1、T2中的每個基團可被一個或多個基團R取代。
- 如請求項1所述的苯並菲衍生物,其中,所述R在每次出現時相同或不同,選自氫原子、氘原子、鹵素原子、腈基、N(Ar1)2、具有C1-C40的直鏈烷基、具有C1-C40的直鏈雜烷基、具有C3-C40的支鏈或環狀的烷基、具有C3-C40的支鏈或環狀的雜烷基、具有C2-C40的烯基或炔基、具有5至80個原子的芳族環或雜芳族環系;Ar1在每次出現時相同或不同,選自具有5~30個原子的芳族或雜芳族環系,所述環系可被一個或多個非芳族基團R8取代;此處鍵合至同一氮原子或磷原子的兩個基團Ar1也可通過單鍵或選自N(R8)、C(R8)2、氧或硫的橋連基彼此橋連; R8選自氫原子、氘原子、氟原子、腈基、具有C1-C20的脂族烴基、具有5~30個原子的芳族環或雜芳族環系,其中一個或多個氫原子可被氘原子、鹵素原子、或腈基代替,其中兩個或更多個相鄰的取代基R8可彼此形成單環或多環的脂族、芳族或雜芳族環系。
- 一種苯並菲衍生物在有機電致發光材料中的應用,其包含請求項1~4任意一項所述的苯並菲衍生物。
- 如請求項5所述的應用,其中,所述的有機電致發光材料為有機電致發光元件用材料、有機場效應電晶體用材料或有機薄膜太陽電池用材料。
- 一種有機電致發光裝置,其中,所述的有機電致發光裝置包括第一電極、第二電極和置於所述第一電極和第二電極之間的至少一層有機層,至少一層有機層包含請求項1~4任意一項所述的苯並菲衍生物。
- 如請求項7所述的有機電致發光裝置,其中,所述的有機層還包括電子注入層、電子輸送層、空穴阻擋層、電子阻擋層、空穴輸送層、空穴注入層、發光層中的一種。
- 如請求項9所述的有機電致發光裝置,其中,所述的摻雜物與發光主體的質量比為1:99~50:50。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011178673.8 | 2020-10-29 | ||
CN202011178673.8A CN112266387B (zh) | 2020-10-29 | 2020-10-29 | 一种苯并菲衍生物及其应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW202216655A TW202216655A (zh) | 2022-05-01 |
TWI808518B true TWI808518B (zh) | 2023-07-11 |
Family
ID=74344876
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW110140148A TWI808518B (zh) | 2020-10-29 | 2021-10-28 | 一種苯並菲衍生物及其應用 |
Country Status (3)
Country | Link |
---|---|
CN (1) | CN112266387B (zh) |
TW (1) | TWI808518B (zh) |
WO (1) | WO2022088911A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112266387B (zh) * | 2020-10-29 | 2023-05-26 | 北京八亿时空液晶科技股份有限公司 | 一种苯并菲衍生物及其应用 |
CN116675706B (zh) * | 2023-08-03 | 2023-12-01 | 吉林奥来德光电材料股份有限公司 | 一种噁唑并苯并咔唑磷光主体材料及应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20160020408A1 (en) * | 2013-03-07 | 2016-01-21 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8592051B2 (en) * | 2003-03-20 | 2013-11-26 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element made with the same |
US11643414B2 (en) * | 2016-04-29 | 2023-05-09 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN110156824A (zh) * | 2018-02-13 | 2019-08-23 | 北京绿人科技有限责任公司 | 有机发光化合物及其应用和有机电致发光器件 |
CN110698430A (zh) * | 2019-10-23 | 2020-01-17 | 苏州久显新材料有限公司 | 硫杂菲啶酮衍生物及其合成方法和含有硫杂菲啶酮衍生物的电子器件 |
CN112266387B (zh) * | 2020-10-29 | 2023-05-26 | 北京八亿时空液晶科技股份有限公司 | 一种苯并菲衍生物及其应用 |
-
2020
- 2020-10-29 CN CN202011178673.8A patent/CN112266387B/zh active Active
-
2021
- 2021-08-30 WO PCT/CN2021/115226 patent/WO2022088911A1/zh active Application Filing
- 2021-10-28 TW TW110140148A patent/TWI808518B/zh active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20160020408A1 (en) * | 2013-03-07 | 2016-01-21 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
Also Published As
Publication number | Publication date |
---|---|
CN112266387A (zh) | 2021-01-26 |
CN112266387B (zh) | 2023-05-26 |
TW202216655A (zh) | 2022-05-01 |
WO2022088911A1 (zh) | 2022-05-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN114591328B (zh) | 一种咔唑衍生物及其应用 | |
CN113801151B (zh) | 一种稠环芳香族化合物及其应用 | |
WO2024012522A1 (zh) | 一种咔唑衍生物及其在oled中的应用 | |
WO2024012469A1 (zh) | 一种咔唑衍生物及其在有机发光元件中的应用 | |
TWI808518B (zh) | 一種苯並菲衍生物及其應用 | |
CN113429302B (zh) | 一种萘并芴衍生物、发光材料、发光元件及消费型产品 | |
WO2024012512A1 (zh) | 一种咔唑衍生物及包含它的有机发光元件 | |
WO2023065996A1 (zh) | 蒽衍生物、有机电致发光材料、发光装置及消费型产品 | |
WO2022237407A1 (zh) | 一种有机化合物、有机电致发光材料及其装置 | |
WO2023151394A1 (zh) | 一种芴衍生物及其应用 | |
WO2023231795A1 (zh) | 一种杂环化合物及包含它的有机发光元件 | |
CN114957226B (zh) | 一种菲啶衍生物及其应用 | |
CN112876498B (zh) | 多环芳族化合物和含有该多环芳族化合物的有机电致发光元件 | |
CN114044785A (zh) | 一种含硼化合物和有机电致发光元件、有机电致发光材料 | |
CN114907179B (zh) | 蒽衍生物及使用其的有机电致发光材料、发光装置和消费型产品 | |
CN112794804B (zh) | 螺芴衍生物及其应用 | |
CN115028630A (zh) | 一种氮杂金刚烷化合物、有机电致发光元件 | |
CN112812023B (zh) | 有机化合物、有机电致发光器件用材料、有机电致发光器件 | |
CN112812108B (zh) | 化合物及包含该化合物的有机电致发光装置 | |
CN113912636B (zh) | 含硅杂环化合物和含有该化合物的有机电致发光元件 | |
CN112794833B (zh) | 一种蓝光染料化合物及其应用 | |
CN116444547B (zh) | 一种萘硼-氮化合物及其应用 | |
CN112812108A (zh) | 化合物及包含该化合物的有机电致发光装置 | |
CN113461718A (zh) | 一种多环芳族化合物及有机电致发光元件 | |
CN114890959A (zh) | 一种荧蒽衍生物及其应用 |