CN109575001A - 3- dibenzofurans based triazine derivative organic compound and the organic electroluminescence device comprising it - Google Patents
3- dibenzofurans based triazine derivative organic compound and the organic electroluminescence device comprising it Download PDFInfo
- Publication number
- CN109575001A CN109575001A CN201711318649.8A CN201711318649A CN109575001A CN 109575001 A CN109575001 A CN 109575001A CN 201711318649 A CN201711318649 A CN 201711318649A CN 109575001 A CN109575001 A CN 109575001A
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- China
- Prior art keywords
- layer
- mentioned
- compound
- dibenzofurans
- triazine derivative
- Prior art date
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- -1 triazine derivative organic compound Chemical class 0.000 title claims abstract description 31
- 238000005401 electroluminescence Methods 0.000 title claims description 24
- 239000000126 substance Substances 0.000 claims abstract description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 89
- 239000000463 material Substances 0.000 claims description 26
- 239000010409 thin film Substances 0.000 claims description 20
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002346 layers by function Substances 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
- 239000000872 buffer Substances 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 230000004888 barrier function Effects 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims 1
- RDRCCJPEJDWSRJ-UHFFFAOYSA-N pyridine;1h-pyrrole Chemical compound C=1C=CNC=1.C1=CC=NC=C1 RDRCCJPEJDWSRJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 83
- 238000006243 chemical reaction Methods 0.000 description 36
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- 230000000052 comparative effect Effects 0.000 description 23
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 239000004327 boric acid Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 4
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 4
- 239000005416 organic matter Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- YWWZASFPWWPUBN-UHFFFAOYSA-N 1-bromoisoquinoline Chemical compound C1=CC=C2C(Br)=NC=CC2=C1 YWWZASFPWWPUBN-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 2
- SCRBSGZBTHKAHU-UHFFFAOYSA-N 4-bromoisoquinoline Chemical compound C1=CC=C2C(Br)=CN=CC2=C1 SCRBSGZBTHKAHU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MUEHGEQAMLEEID-UHFFFAOYSA-N 1-pentyl-2-phenylbenzene Chemical group CCCCCC1=CC=CC=C1C1=CC=CC=C1 MUEHGEQAMLEEID-UHFFFAOYSA-N 0.000 description 1
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical class BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- ZGIKWINFUGEQEO-UHFFFAOYSA-N 3-bromoquinoline Chemical compound C1=CC=CC2=CC(Br)=CN=C21 ZGIKWINFUGEQEO-UHFFFAOYSA-N 0.000 description 1
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- SUXIPCHEUMEUSV-UHFFFAOYSA-N 4-bromoquinoline Chemical compound C1=CC=C2C(Br)=CC=NC2=C1 SUXIPCHEUMEUSV-UHFFFAOYSA-N 0.000 description 1
- XYBSZCUHOLWQQU-UHFFFAOYSA-N 7-bromoquinoline Chemical compound C1=CC=NC2=CC(Br)=CC=C21 XYBSZCUHOLWQQU-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 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
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical class ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
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- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HHAVHBDPWSUKHZ-UHFFFAOYSA-N propan-2-ol;propan-2-one Chemical compound CC(C)O.CC(C)=O HHAVHBDPWSUKHZ-UHFFFAOYSA-N 0.000 description 1
- 150000003921 pyrrolotriazines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 238000007740 vapor deposition Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Abstract
The present invention provides the 3- dibenzofurans based triazine derivative organic compound comprising heteroaryl connexon indicated by following chemical formula a: chemical formula a:.In above-mentioned chemical formula a, Ar1To Ar3And L is as invented defined in claimed range.
Description
Technical field
The present invention relates to 3- dibenzofurans based triazine derivative organic compound and include its organic electroluminescence
Part.
Background technique
Electroluminescent device (electroluminescence device:EL device) is shown as self light-generating type
Device has the advantages that fast response time, visual angle are broad.1987 Eastman Kodak Co (Eastman Kodak) open for the first time
The organic electroluminescence device using low molecule aromatic diamine and aluminium complex as emitting layer material is sent out
[Appl.Phys.Lett.51,913,1987].
In organic electroluminescence device, determines that the most important factor of luminous efficiency is luminescent material, but shine material
Phosphor material in material is compared with fluorescent material, and theoretically amendatory luminous efficiency reaches 4 times.So far, well-known
Phosphorescent light-emitting materials have iridium (III) complexing species and carbazoles material, studying novel phosphor material recently.
The principle of organic electroluminescent phenomenon is, when between cathode and anode there are when organic thin film layer, if to two
Apply voltage between electrode, then injects electrons and holes from cathode and anode to organic thin film layer respectively.To organic thin film layer
Injected electrons and hole recombination are simultaneously formed exciton (exciton), and exciton falls to ground state again and shines.Utilize this original
The organic electroluminescence device of reason can usually be constituted by being located at cathode and anode and the organic thin film layer between them, for example, by
Organic thin film layer including hole injection layer, hole transmission layer, luminescent layer, electron transfer layer is constituted.
As the material used in organic electroluminescence device, most of is to make pure organic matter or by organic matter and metal
The complex compound for forming complexing, can be divided into hole-injecting material, hole mobile material, luminescent material, electron-transport material depending on the application
Material, electron injection material etc..Wherein, hole-injecting material or hole mobile material be as the organic material with p-type property,
That is, main use is easy to oxidation and the organic matter with electrochemically stable state in oxidation.On the other hand, electron injection material
Or electron transport material is as the organic material with n-type property, that is, main use is easy to restore and has electricity in reduction
The organic matter of chemically stable state.Emitting layer material is as the material simultaneously with p-type property and n-type property, that is, preferably
To be preferably converted into the tool of light when forming exciton in the material for aoxidizing with all having stable state under reducing condition
There is the material of high-luminous-efficiency.Therefore, the art needs to develop the new organic materials for having condition as described above.
Summary of the invention
The technical problem to be solved in the present invention
An example of the invention, which provides, to be had energy level appropriate, electrochemical stability and thermal stability and is included in 3- hexichol
And the compound of the connexon between furans and triazine with heteroaryl substituent.
It includes upper with heteroaryl substituent between 3- dibenzofurans and triazine that another example of the invention, which provides,
State the organic electroluminescence device of connexon.
Technical solution
In an example of the invention, the 3- dibenzofurans based triazine derivative that providing is indicated by following chemical formula a has
Machine compound:
Chemical formula a:
In above-mentioned chemical formula a, L is singly-bound or phenylene, Ar1For the heteroaryl of substituted or unsubstituted C3-C60,
Above-mentioned Ar1Substituent group in substituted situation is selected from by the alkyl of C1~C30, the aryl of C6~C30 and their combination
One of group of composition, Ar2And Ar3It is separately the aryl of substituted or unsubstituted C6-C60, substituted or unsubstituted
The heteroaryl of C3-C60, in above-mentioned Ar1And Ar2Substituent group in substituted situation be selected from by C1~C30 alkyl, C6~
One of the aryl of C30, the heteroaryl of C5~C30 and group of their combination composition.
Specifically, above-mentioned Ar1It can be selected from one of pyridine, quinoline, isoquinolin or phenanthridinyl.
Specifically, above-mentioned Ar2And above-mentioned Ar3It can separately be phenyl, naphthalene, xenyl, phenanthryl, fluorenyl, spiro fluorene
Base, benzothienyl, benzofuranyl, dibenzofuran group, dibenzothiophene, terphenyl, pyridyl group, phenylpyridyl
Or pyrimidine radicals.
Above-mentioned organic compound can be used as luminescent layer, hole blocking layer, electronics in material for organic electroluminescent device
The substance of transport layer or electron injecting layer.
In another example of the invention, following organic electroluminescence device is provided, that is, press from both sides between cathode and anode
There is at least one organic thin film layer, above-mentioned organic thin film layer has the multilayered structure including at least one luminescent layer, above-mentioned to shine
At least one layer in layer or the above-mentioned organic thin film layer other than above-mentioned luminescent layer includes above-mentioned 3- dibenzofuran group three
One of oxazine derivatives organic compound or two or more mixtures.
Also, provide following device, that is, above-mentioned organic thin film layer is between cathode and luminescent layer, including has electricity
The electron transporting zone of at least one of sub- implanted layer, electron transfer layer, functional layer, buffer layer and hole blocking layer, it is above-mentioned
Functional layer has the function of electronics injecting function and electron-transport simultaneously.
Beneficial effect
Above-mentioned 3- dibenzofurans based triazine derivative compound can first-class meet in organic electroluminescence device
In condition, such as energy level appropriate, electrochemical stability and thermal stability needed for the substance that can be used etc., according to substituent group
It can play the role of a variety of needed for the organic electroluminescence device.
Detailed description of the invention
Fig. 1 and Fig. 2 be show it is related with the organic electroluminescence device prepared in embodiment 1~11 and the Comparative Examples 1 to 5
The life characteristic appraisal curve figure of measurement result.
Fig. 3 is survey related with the organic electroluminescence device prepared in embodiment 12~14 and comparative example 2 and comparative example 6
Determine the life characteristic appraisal curve figure of result.
Specific embodiment
Hereinafter, the example that the present invention will be described in detail.But these examples only propose that the present invention is simultaneously unlimited as illustrating
Due to this, the range of range should be claimed based on aftermentioned invention to define in the present invention.
In the present specification, unless otherwise defined, the case where " substitution " include the alkyl of selected free C1-C12, amino,
Itrile group, the naphthenic base of C3-C7, the alkenyl of C2-C12, the cycloalkenyl of C3-C7, the alkynyl of C2-C50, the cycloalkynyl radical of C5-C50, cyanogen
Base, the alkoxy of C1-C12, the aryl of C6-C60 and C7-C60 aralkyl and their combination composition group in substituent group
The case where substitution.
In the present specification, unless otherwise defined, " their combination " refer to more than two substituent groups by linker come
It combines, or more than two substituent groups are by being condensed the state combined.
In the present specification, unless otherwise defined, " miscellaneous " refers to that a compound or substituent group include hetero atom, above-mentioned miscellaneous
Atom can be for selected from one of the group being made of N, O, S, P and their combination.For example, can refer to following situation, that is, on
It states a compound or substituent group includes 1 to 3 hetero atom, and remaining is carbon.
In an example of the invention, the novel 3- dibenzofuran group triazine derivatives indicated by following chemical formula a are provided
Object organic compound:
Chemical formula a:
In above-mentioned chemical formula a, L is singly-bound or phenylene, Ar1For the heteroaryl of substituted or unsubstituted C3-C60,
Above-mentioned Ar1Substituent group in substituted situation is selected from by the alkyl of C1~C30, the aryl of C6~C30 and their combination
One of group of composition, Ar2And Ar3It is separately the aryl of substituted or unsubstituted C6-C60, substituted or unsubstituted
The heteroaryl of C3-C60, in above-mentioned Ar1And Ar2Substituent group in substituted situation be selected from by C1~C30 alkyl, C6~
One of the aryl of C30, the heteroaryl of C5~C30 and group of their combination composition.
Specifically, Ar1It can be pyridine, quinoline, isoquinolin or phenanthridinyl.
Specifically, Ar2To Ar3It can separately be phenyl, naphthalene, xenyl, phenanthryl, fluorenyl, Spirofluorene-based, benzo
Thienyl, benzofuranyl, dibenzofuran group, dibenzothiophene, terphenyl, pyridyl group, phenylpyridyl or pyrimidine
Base.
For example, above-mentioned 3- dibenzofurans based triazine derivative organic compound can for recorded in following table 11 to
One of 130 compounds.
Table 1
Above-mentioned 3- dibenzofurans based triazine derivative compound is in the case where being used as organic electroluminescence device, equal energy
Condition needed for enough first-class meeting the substance that can be used in organic electroluminescence device, such as energy level appropriate, electrification
Learn stability and thermal stability etc., according to substituent group can play the role of in organic electroluminescence device needed for it is a variety of.
In another example of the invention, following organic electroluminescence device is provided, that is, press from both sides between cathode and anode
There is at least one organic thin film layer, above-mentioned organic thin film layer has the multilayered structure including at least one luminescent layer, above-mentioned to shine
At least one layer in layer or the above-mentioned organic thin film layer other than above-mentioned luminescent layer includes above-mentioned 3- dibenzofuran group three
One of oxazine derivatives organic compound or two or more mixtures.
Included in the above-mentioned 3- dibenzofurans based triazine derivative of the organic thin film layer of above-mentioned organic electroluminescence device
Compound is the compound indicated by above-mentioned chemical formula a, and relative detailed description is as described above.
In one example, according to required purposes, above-mentioned organic thin film layer can be uitably included selected from by hole blocking layer, hair
One or more of photosphere, electron transfer layer and group of electron injecting layer composition.
In another example, above-mentioned organic thin film layer is between cathode and luminescent layer, it may include have electron injecting layer,
The electron transporting zone of at least one of electron transfer layer, functional layer, buffer layer and hole blocking layer, above-mentioned functional layer is simultaneously
Have the function of electronics injecting function and electron-transport.
Above-mentioned hole injection layer, hole transmission layer, functional layer, buffer layer, electronic barrier layer, luminescent layer, hole blocking layer,
Electron transfer layer, electron injecting layer etc. can be formed respectively using well known substance or they one or more of may include
More than one 3- dibenzofurans based triazine derivative compounds indicated by above-mentioned chemical formula a.
With the 3- dibenzofuran group triazine derivatives indicated by above-mentioned chemical formula a for being included in above-mentioned organic thin film layer
The relevant detailed description of compounds is as described above.
Hereinafter, being recorded to the embodiment of the present invention and comparative example.These following embodiments are only a realities of the invention
Example is applied, the present invention is not limited to following embodiments.
Embodiment
Hereinafter, particular instantiation is carried out to reaction example and comparative example, but the present invention is not limited to following reaction examples and realities
Apply example.In following reaction examples, to mark midbody compound in such a way that the number of final product adds sequence number.For example,
Compound 1 is labeled as compound [1], and by the midbody compound of above compound labeled as [1-1] etc..In this specification
In, the number of compound is recorded in the number of the chemical formula of above-mentioned table 1.For example, the change that will be indicated by 1 in table 1
Conjunction substance markers are compound 1.
Reaction equation 1
The preparation of midbody compound [6-1]
Into the reaction flask of 3L put into 100g (542.27mmol, 1.0eq) 2,4,6- tri- chloro-1,3,5-triazines,
The anhydrous tetrahydro furan of 800ml (8ml/g) is stirred under nitrogen atmosphere with 0 DEG C of temperature.It is slowly added 97.93ml (1M
Solution in THF, 1.0eq) phenyl-magnesium-bromide and warm naturally to room temperature, stir 1 hour.To 2N- hydrochloride water
After adding reaction solution in solution, cleaned using methylene chloride, distilled water.It is filtered using anhydrous magnesium sulfate drying and by silica gel,
It after filtered fluid is concentrated under reduced pressure, is recrystallized using methylene chloride, hexane, to be prepared for the rice of 98g (80%)
The midbody compound [6-1] of color solid.
The preparation of midbody compound [6-2]
Compound [6-1], the 90.14g of 98g (433.51mmol, 1.0eq) are put into the reaction flask of 3L
The anhydrous tetrahydro furan of [1,1 '-the biphenyl] -4- base-boric acid of (455.19mmol, 1.05eq), 785ml (8ml/g), in nitrogen
Under atmosphere, stirred with 50 DEG C of temperature.50 DEG C at a temperature of, be added 10g (8.67mmol, 0.02eq) tetrakis triphenylphosphine palladium
(0), after potassium carbonate and addition that 119.83g (867.03mmol, 2.0eq) is dissolved in the distilled water of 200ml, return stirring mistake
Night.Reaction solution is cooled to room temperature and is filtered.Solid is cleaned using methanol, distilled water.It is recrystallized using toluene, thus
It is prepared for the midbody compound [6-2] of the beige solid of 96g (65%).
The preparation of midbody compound [6-3]
Compound [6-2], the 98.54g of 96g (279.22mmol, 1.0eq) are put into the reaction flask of 3L
Isosorbide-5-Nitrae-the dioxane of (the bromo- 5- chlorphenyl of the 3-) boric acid of (418.84mmol, 1.5eq), 770ml (8ml/g), in nitrogen atmosphere
Under, it is stirred with 60 DEG C of temperature.60 DEG C at a temperature of, be added 6.45g (5.58mmol, 0.02eq) tetrakis triphenylphosphine palladium
(0), after potassium carbonate and addition that 57.89g (418.84mmol, 1.5eq) is dissolved in the distilled water of 150ml, return stirring mistake
Night.Reaction solution is cooled to room temperature and is filtered.Solid is cleaned using methanol, distilled water.It is recrystallized using toluene, thus
It is prepared for the midbody compound [6-3] of the beige solid of 83g (60%).
The preparation of midbody compound [6-4]
Compound [6-3], the 78.53g of 83g (352.79mmol, 1.0eq) are put into the reaction flask of 3L
Dibenzo [b, the d] furans -3- base of (370.43mmol, 1.05eq)] boric acid, 800ml (10ml/g) anhydrous tetrahydro furan,
Under nitrogen atmosphere, stirred with 50 DEG C of temperature.50 DEG C at a temperature of, be added 8.15g (7.06mmol, 0.02eq) four (triphens
Base phosphine) palladium (0), after the sodium hydroxide of 42.33g (1058.36mmol, 3.0eq) and addition are dissolved in the distilled water of 160ml,
Return stirring is stayed overnight.Reaction solution is cooled to room temperature and is filtered.Solid is cleaned using methanol, distilled water.It is carried out again using toluene
Crystallization, to be prepared for the midbody compound [6-4] of the beige solid of 124g (60%).
The preparation of midbody compound [6-5]
The compound [6-4] of investment 124g (211.58mmol, 1.0eq), 4,4,4 ', 4 ', 5 into the reaction flask of 3L,
5,5 ', 5 '-prestox -2, anhydrous tetrahydro furan, the 1.43g of 2 '-bis- (1,3,2- bis- evil borines), 1000ml (8ml/g)
The 2- dicyclohexyl phosphorus -2 ' of the acid chloride of (6.35mmol, 0.03eq), 6.05g (12.69mmol, 0.06eq), 4 ', 6 '-three is different
The potassium acetate of pentylbiphenyl (trade name Xphos), 62.3g (634.73mmol, 3.0eq), under nitrogen atmosphere, return stirring 2
Hour.Reaction solution is cooled to room temperature, and is cleaned using chloromethanes, distilled water.Using anhydrous magnesium sulfate drying and pass through silica gel
Filtering, after filtered fluid is concentrated under reduced pressure, is recrystallized using acetone, hexane, to be prepared for the rice of 98g (80%)
The midbody compound [6-5] of color solid.
The preparation of compound [6]
Compound [6-5], the 2.32ml of 15g (22.14mmol, 1.0eq) are put into the reaction flask of 1L
The 2- bromopyridine of (24.35mmol, 1.1eq), the anhydrous tetrahydro furan of 450ml (30ml/g), 0.1g (0.44mmol, 0.02eq)
Palladium (2) acetate, 0.42g (0.89mmol, 0.04eq) 2- dicyclohexyl phosphorus -2 ', 4 ', 6 '-tri isopropyl biphenyls, in nitrogen
Under atmosphere, stirred with 50 DEG C of temperature.50 DEG C at a temperature of, in the distilled water of 90ml dissolve 14.1g (66.41mmol,
After potassium phosphate 3.0eq) and addition, return stirring 2 hours.Reaction solution is cooled to room temperature and is filtered.Utilize methanol, distilled water
Clean solid.It is recrystallized using anhydrous tetrahydro furan, to be prepared for the target of the white solid of 11.13g (80%)
Compound [6].
The preparation of compound [86]
Into the reaction flask of 1L put into 15g (22.14mmol, 1.0eq) compound [6-5], (24.35mmol,
Palladium (2) second of the anhydrous tetrahydro furan of 4- bromo-isoquinoline, 450ml (30ml/g) 1.1eq), 0.1g (0.44mmol, 0.02eq)
The 2- dicyclohexyl phosphorus -2 ' of hydrochlorate, 0.42g (0.89mmol, 0.04eq), 4 ', 6 '-tri isopropyl biphenyls, under nitrogen atmosphere, with
50 DEG C of temperature stirring.50 DEG C at a temperature of, in the distilled water of 90ml dissolve 14.1g (66.41mmol, 3.0eq) phosphorus
After sour potassium and addition, return stirring 2 hours.Reaction solution is cooled to room temperature and is filtered.Solid is cleaned using methanol, distilled water.
It is recrystallized using toluene, to be prepared for the target compound [86] of the white solid of 11.26g (75%).
The preparation of compound [96]
Compound [6-5], the 5.07g of 15g (22.14mmol, 1.0eq) are put into the reaction flask of 1L
The 2- bromoquinoline of (24.35mmol, 1.1eq), 450ml (30ml/g) anhydrous tetrahydro furan, 0.1g (0.44mmol, 0.02eq)
The 2- dicyclohexyl phosphorus -2 ' of palladium (2) acetate, 0.42g (0.89mmol, 0.04eq), 4 ', 6 '-tri isopropyl biphenyls, in nitrogen
Under atmosphere, stirred with 50 DEG C of temperature.50 DEG C at a temperature of, in the distilled water of 90ml dissolve 14.1g (66.41mmol,
After potassium phosphate 3.0eq) and addition, return stirring 2 hours.Reaction solution is cooled to room temperature and is filtered.Utilize methanol, distilled water
Clean solid.It is recrystallized using toluene, to be prepared for the target compound of the white solid of 10.52g (70%)
[96]。
Reaction equation 2
The preparation of compound [77]
Pass through method identical with reaction equation 1 and utilizes with 2- naphthalene vinyl boric acid instead of using [1,1 '-biphenyl] -4-
Base-boric acid is come the compound [77-5] of the 10g (15.35mmol, 1.0eq) prepared, the 3- of 3.51g (16.88mmol, 1.1eq)
Bromo-isoquinoline is prepared for the target compound [77] of the white solid of 7.9g (79%).
Reaction equation 3
The preparation of compound [1]
As starting material and pass through method identical with reaction equation 1 using using the chloro- 4,6- diphenyl -1,3,5- triazine of 2-
The 2- bromine pyrrole of the midbody compound [1-3] of the 10g (16.62mmol, 1.0eq) of preparation, 1.74ml (18.29mmol, 1.1eq)
Pyridine is prepared for the target compound [1] of 7.26g (79%) white solid.
The preparation of compound [21]
Utilize the midbody compound of the 10g (16.62mmol, 1.0eq) prepared by method identical with reaction equation 3
The 3- bromopyridine of [1-3], 1.79ml (18.29mmol, 1.1eq) are prepared for the target chemical combination of the white solid of 7.35g (80%)
Object [21].
The preparation of compound [61]
Utilize the midbody compound of the 10g (16.62mmol, 1.0eq) prepared by method identical with reaction equation 3
The 1- bromo-isoquinoline of [1-3], 3.8g (18.29mmol, 1.1eq) are prepared for the target chemical combination of the white solid of 7.61g (76%)
Object [61].
The preparation of compound [81]
Utilize the midbody compound of the 10g (16.62mmol, 1.0eq) prepared by method identical with reaction equation 3
The 4- bromo-isoquinoline of [1-3], 3.8g (18.29mmol, 1.1eq) (18.29mmol, 1.1eq) are prepared for the white of 7.51g (75%)
The target compound [81] of color solid.
The preparation of compound [121]
Utilize the midbody compound of the 10g (16.62mmol, 1.0eq) prepared by method identical with reaction equation 3
The 6- bromine phenanthridines of [1-3], 4.72g (18.29mmol, 1.1eq) are prepared for the target compound of the white solid of 7.05g (65%)
[121]。
The preparation of compound [127]
Utilize the midbody compound of the 10g (16.62mmol, 1.0eq) prepared by method identical with reaction equation 3
The 7- bromoquinoline of [1-3], 3.8g (18.29mmol, 1.1eq) are prepared for the target compound of the white solid of 7.01g (70%)
[127]。
Reaction equation 4
The preparation of compound [45]
Using by 2,4- bis- ([1,1 '-biphenyl) -4- base) -6- chloro-1,3,5-triazines as starting material and by with it is anti-
Midbody compound [45-3], the 1.44ml for the 10g (13.26mmol, 1.0eq) for answering the identical method of formula 1 to prepare
The 4- bromopyridine of (14.59mmol, 1.1eq) is prepared for the target compound [45] of the white solid of 6.55g (70%).
Reaction equation 5
The preparation of compound [39]
Using by 2- (3- bromophenyl) -4,6- diphenyl -1,3,5-triazines as starting material and by with 1 phase of reaction equation
With the midbody compound [39-3] of 10g (14.76mmol, 1.0eq) of method preparation, 1.59ml (16.23mmol,
3- bromopyridine 1.1eq) is prepared for the target compound [39] of the white solid of 7.42g (80%).
The preparation of compound [110]
Pass through method identical with reaction equation 5 and utilizes compound [39-3], the 3.38g of 10g (14.76mmol, 1.0eq)
The 3- bromoquinoline of (16.23mmol, 1.1eq) is prepared for the target compound [110] of the white solid of 7.21g (72%).
The preparation of compound [120]
Pass through method identical with reaction equation 5 and utilizes compound [39-3], the 3.38g of 10g (14.76mmol, 1.0eq)
The 4- bromoquinoline of (16.23mmol, 1.1eq) is prepared for the target compound [120] of the white solid of 7g (70%).
Compound 1 is prepared for the preparation method of reaction equation 5 to compound 130, in following table according to above-mentioned reaction equation 1
Its result is shown in 2.
Table 2
Comparative example compound
Chemical formula b:
Chemical formula c:
Chemical formula d:
Chemical formula e:
Comparative example 1
The compound f indicated by following chemical formula f is used as Day-Glo blue host, the chemical combination indicated by following chemical formula g
Object g is used as Day-Glo blue dopant, 2-TNATA (4,4', 4 "-three (N- naphthalene -2- base)-N- phenylaminos-triphenylamine (4,4 ',
4 "-tris (N-naphthalen-2-yl)-N-phenylamino)-triphenylamine)) it is used as hole injection layer substance,
By α-NPD (N, N'- bis- (naphthalene -1- base)-N, N'- diphenylbenzidine (N, N '-di (naphthalene-1-yl)-N, N ' -
Diphenylbenzidine)) it is used as hole transmission layer substance, is thus prepared for the organic luminescent device having the following structure:
ITO/2-TNATA (60nm)/α-NPD (30nm)/compound f+ compound g (30nm)/Alq3(25nm)/Liq(1nm)/Al
(100nm)。
Use following anode, that is, by 15 Ω of Corning Incorporated (Corning)/cm2() ito glass substrate cuts
It is cut into 25mm × 25mm × 0.7mm size, respectively in acetone isopropanol and pure water after ultrasonic cleaning 15 minutes, into
Row 30 minutes ultraviolet (UV) ozone cleans.The sky of 60nm thickness is formed in the top vacuum evaporation 2-TNATA of aforesaid substrate
Cave implanted layer.The hole transmission layer of 30nm thickness is formed in the top vacuum evaporation α-NPD of above-mentioned hole injection layer.Above-mentioned
The top vacuum evaporation of hole transmission layer is by the chemical formula f compound indicated and the compound indicated by chemical formula g (doping rate: 4
Weight percent) form the luminescent layer of 30nm thickness.Then, on the top of above-mentioned luminescent layer with the thickness vacuum evaporation of 25nm
Alq3Compound forms electron transfer layer.The top of above-mentioned electron transfer layer successively vacuum evaporation 1nm Liq (electronics note
Enter layer) and the Al (cathode) of 100nm prepare organic luminescent device as shown in table 3.It is referred to as comparative sample 1.
Chemical formula f:
Chemical formula g:
BCP:
Alq3:
Comparative example 2~5
In above-mentioned comparative example 1, electron transfer layer compound Alq is replaced using following compound b, c, d and e respectively3,
Thus it is prepared for the organic luminescent device having the following structure: ITO/2-TNATA (60nm)/α-NPD (30nm)/compound f+ization
Close object g (30nm)/compound b, c, d or e (25nm)/Liq (1nm)/Al (100nm).Comparative example 2 is referred to as to comparing
Example 5.
Comparative example 6
In addition to electron transfer layer use above compound b and as cave barrier layer compound vapor deposition 5nm above-mentioned BCP with
Outside, organic luminescent device is prepared in method identical with above-mentioned comparative example 1.It is referred to as comparative example 6.
Embodiment 1~11
It is logical in addition to making synthesized compound 1,21,45,61,81,121,127,6,77,86,96 as shown in Table 1 above
Sublimation purification process is crossed to replace Alq respectively3And be used as other than electron transfer layer, with method system identical with above-mentioned comparative example 1
Standby organic luminescent device, and be shown in table 3.Embodiment 1 is referred to as to embodiment 11.
Embodiment 12~14
In addition to making synthesized compound 39,110,120 as shown in Table 1 above by sublimation purification process come generation respectively
It is used as other than hole blocking layer for compound BCP, prepares organic luminescent device in method identical with above-mentioned comparative example 6, and
It is shown in table 3.Embodiment 12 is referred to as to embodiment 14.
Evaluate example 1: the characteristics of luminescence and life assessment of comparative example 1~6 and embodiment 1~14
For comparative example 1~6 and embodiment 1~14, utilize Keithley digital sourcemeter (Keithley sourcemeter)
" 2400 ", Konica Minolta (KONIKA MINOLTA) " CS-2000 " have rated luminescence peak, luminous efficiency, utilize arteries and veins
The M6000S biometrics device of scientific (mcscience) company and initial stage brightness (L with 1000nit0) on the basis of, it measures bright
Degree (L) reaches for 97% time (LT97), its result is shown in following table 3 and Fig. 1 to Fig. 3.
Table 3
As shown in Table 3 above, compared with the Comparative Examples 1 to 5, embodiment 1~11 presents low voltage drive and is improved
The characteristics of luminescence.Also, when using hole blocking layer, low voltage drive is also presented, the characteristics of luminescence that is improved and longevity
Order characteristic.
Fig. 1 and Fig. 2 be show it is related with the organic electroluminescence device prepared in embodiment 1~11 and the Comparative Examples 1 to 5
The life characteristic appraisal curve figure of said determination result.
Fig. 3 is on related with the organic electroluminescence device prepared in embodiment 12~14 and comparative example 2 and comparative example 6
State the life characteristic appraisal curve figure of measurement result.
As shown in Table 3 above, compared with comparative example 1~6, embodiment 1~14 presents the life characteristic being improved.Especially
It, the above compound for importing the pyrrolotriazine derivatives of the connexon in 3- dibenzofuran group with heteroaryl substituent is presented
Outstanding performance and service life.
More than, multiple preferred embodiments of the invention are described in detail, but invention of the invention is claimed
It's not limited to that for range, and field technical staff utilizes basic conception of the invention defined in the claimed range of invention
Various deformation and improvement form to carry out also belong to invention of the invention and range are claimed.
Claims (7)
1. a kind of 3- dibenzofurans based triazine derivative organic compound, which is characterized in that indicated by following chemical formula a:
Chemical formula a:
In above-mentioned chemical formula a,
L be singly-bound or phenylene,
Ar1For the heteroaryl of substituted or unsubstituted C3-C60, in above-mentioned Ar1Substituent group in substituted situation be selected from by
One of the alkyl of C1~C30, the aryl of C6~C30 and group of their combination composition,
Ar2And Ar3It is separately the heteroaryl of the aryl of substituted or unsubstituted C6-C60, substituted or unsubstituted C3-C60
Base, in above-mentioned Ar1And Ar2Substituent group in substituted situation is aryl, C5 selected from alkyl, C6~C30 by C1~C30
One of the group of heteroaryl and the their combination composition of~C30.
2. 3- dibenzofurans based triazine derivative organic compound according to claim 1, which is characterized in that Ar1For pyrrole
Pyridine, quinoline, isoquinolin or phenanthridinyl.
3. 3- dibenzofurans based triazine derivative organic compound according to claim 1, which is characterized in that Ar2And
Ar3It is separately phenyl, naphthalene, xenyl, phenanthryl, fluorenyl, Spirofluorene-based, benzothienyl, benzofuranyl, dibenzo
Furyl, dibenzothiophene, terphenyl, pyridyl group, phenylpyridyl or pyrimidine.
4. 3- dibenzofurans based triazine derivative organic compound according to claim 1, which is characterized in that above-mentionedization
Formula a is one of following 1 to 130:
5. 3- dibenzofurans based triazine derivative organic compound according to claim 1, which is characterized in that above-mentioned 3-
Dibenzofurans based triazine derivative organic compound is used as luminescent layer, hole barrier in material for organic electroluminescent device
The substance of layer, electron transfer layer or electron injecting layer.
6. a kind of organic electroluminescence accompanies at least one organic thin film layer, above-mentioned organic electroluminescence between cathode and anode
Luminescent device is characterized in that,
Above-mentioned organic thin film layer has the multilayered structure including at least one luminescent layer,
At least one layer in above-mentioned luminescent layer or above-mentioned organic thin film layer other than above-mentioned luminescent layer includes claim 1
To one of 3- dibenzofurans based triazine derivative organic compound or two or more mixing described in any one of 5
Object.
7. organic electroluminescence device according to claim 6, which is characterized in that above-mentioned organic thin film layer between cathode with
Between luminescent layer, including at least one in electron injecting layer, electron transfer layer, functional layer, buffer layer and hole blocking layer
The electron transporting zone of kind, above-mentioned functional layer have the function of electronics injecting function and electron-transport simultaneously.
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