CN106414404B - 用于有机电致发光器件的材料 - Google Patents
用于有机电致发光器件的材料 Download PDFInfo
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- CN106414404B CN106414404B CN201580018975.XA CN201580018975A CN106414404B CN 106414404 B CN106414404 B CN 106414404B CN 201580018975 A CN201580018975 A CN 201580018975A CN 106414404 B CN106414404 B CN 106414404B
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- 239000000463 material Substances 0.000 title description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 29
- 239000011159 matrix material Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000002019 doping agent Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- -1 heteroaryl radical Chemical class 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
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- 125000001072 heteroaryl group Chemical group 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 239000000412 dendrimer Substances 0.000 description 12
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- 125000003545 alkoxy group Chemical group 0.000 description 9
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- 238000002347 injection Methods 0.000 description 5
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- 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 4
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007347 radical substitution reaction Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
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- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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- 125000005259 triarylamine group Chemical group 0.000 description 3
- 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 2
- 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-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
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- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical class N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 2
- KXSRZIZFVZBIIT-UHFFFAOYSA-N 6-bromo-1,3-diphenyl-9H-carbazole Chemical compound BrC=1C=C2C=3C=C(C=C(C=3NC2=CC=1)C1=CC=CC=C1)C1=CC=CC=C1 KXSRZIZFVZBIIT-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical class 0.000 description 2
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- 229910052802 copper Inorganic materials 0.000 description 2
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- 229920001002 functional polymer Polymers 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
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- 125000004475 heteroaralkyl group Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical class C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 125000006413 ring segment Chemical group 0.000 description 1
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- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
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- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
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- 238000001931 thermography Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000007832 transition metal-catalyzed coupling reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—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 two hetero rings
- C07D405/10—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 two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
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- C07D491/02—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 two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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Abstract
本发明涉及式(1)的化合物,所述化合物适合用于电子器件,特别是有机电致发光器件中。
Description
本发明涉及咔唑衍生物,尤其是用作有机电致发光器件中的三重态基质材料的咔唑衍生物。本发明还涉及制备本发明化合物的方法以及涉及包含这些化合物的电子器件。
例如在US 4539507、US 5151629、EP 0676461和WO 98/27136中描述了其中将有机半导体用作功能材料的有机电致发光器件(OLED)的结构。所使用的发光材料常常是显示磷光而非荧光的有机金属络合物。出于量子力学的原因,使用有机金属化合物作为磷光发光体可以获得高达四倍的能量效率和功率效率。一般来讲,在OLED中,尤其还在显示三重态发光(磷光)的OLED中,例如关于效率、工作电压和寿命方面仍有改进的需要。
磷光OLED的特性不只是由所使用的三重态发光体来确定。更特别地,所使用的其它材料,例如基体材料,在此也是特别重要的。因此,对这些材料的改进也可以导致OLED特性的显著改进。
根据现有技术,除了其它材料外,吲哚并咔唑衍生物(例如根据WO 2007/063754或WO 2008/056746)或茚并咔唑衍生物(例如根据WO 2010/136109或WO 2011/000455),尤其是被缺电子杂芳族化合物例如三嗪取代的那些被用作磷光发光体的基质材料。此外,例如,使用双二苯并呋喃衍生物(例如根据EP 2301926)作为磷光发光体的基质材料。然而,在使用这些基质材料的情况下,尤其是关于器件的效率、寿命和工作电压方面仍有改进的需要。
本发明所解决的问题是提供适合在荧光或磷光OLED、尤其是磷光OLED中例如用作基质材料或用作电荷传输材料、尤其是空穴传输或电子阻挡材料的化合物。本发明所解决的特定问题是提供还适合用于绿色或蓝色磷光OLED的基质材料,和提供新型电荷传输材料。
令人惊讶地已经发现,含有下式(1)化合物的电致发光器件相比于现有技术具有改进,尤其当用作磷光掺杂剂的基质材料时如此。
其中所用的符号和标记如下:
X在每种情况下相同或不同并且是CR或N;
W是CR1或N;
Y在p+r=0时是N或CR并且在p+r≥0时是C;
L1、L2、L3、L4在每种情况下相同或不同,并且是具有5至40个芳族环原子且可被一个或多个R2基团取代的二价芳族或杂芳族环系;
Ar1、Ar2、Ar3、Ar4在每种情况下是具有6至60个芳族环原子且在每种情况下还可被一个或多个R2基团取代的芳族或杂芳族环系;
Ar在每种情况下相同或不同并且是芳族或杂芳族环系,优选芳基或杂芳基基团,其具有5至40个芳族环原子且可被一个或多个R4基团取代;
R、R2在每种情况下相同或不同,并且是H,D,F,Cl,Br,I,N(R3)2,N(Ar)2,C(=O)Ar,P(=O)Ar2,S(=O)Ar,S(=O)2Ar,CR3=CR3Ar,CN,NO2,Si(R3)3,B(OR3)2,OSO2R3,具有1至40个碳原子的直链烷基、烷氧基或硫代烷氧基基团或具有3至40个碳原子的支链或环状的烷基、烷氧基或硫代烷氧基基团,所述基团中的每个可被一个或多个R3基团取代,其中一个或多个非相邻的CH2基团可被R3C=CR3、C≡C、Si(R3)2、C=O、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3代替并且其中一个或多个氢原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,所述环系中的每个可被一个或多个R3基团取代,或具有5至40个芳族环原子且可被一个或多个R3基团取代的芳氧基或杂芳氧基基团,或具有5至40个芳族环原子且可被一个或多个R3基团取代的芳烷基或杂芳烷基基团,或者这些体系的组合;同时,两个或更多个R2取代基与它们所键合的原子一起也可以它们彼此,或两个相邻的R取代基可形成单环或多环的脂族或芳族环系;
R1在每种情况下是H,D,F,Cl,Br,I,N(R5)2,CN,NO2,Si(R5)3,B(OR5)2,OSO2R5,具有1至40个碳原子的直链烷基、烷氧基或硫代烷氧基基团或具有3至40个碳原子的支链或环状的烷基、烷氧基或硫代烷氧基基团,其在每种情况下可被一个或多个R5基团取代,其中一个或多个非相邻的CH2基团可被R5C=CR5、C≡C、Si(R5)2、C=O、C=NR5、P(=O)(R5)、SO、SO2、NR5、O、S或CONR5代替并且其中一个或多个氢原子可被D、F、Cl、Br、I、CN或NO2代替;
R3在每种情况下相同或不同,并且是H,D,F,Cl,Br,I,N(R4)2,C(=O)Ar,P(=O)Ar2,S(=O)Ar,S(=O)2Ar,CR3=CR3Ar,CN,NO2,Si(R4)3,B(OR4)2,OSO2R4,具有1至40个碳原子的直链烷基、烷氧基或硫代烷氧基基团或具有3至40个碳原子的支链或环状的烷基、烷氧基或硫代烷氧基基团,所述基团中的每个可被一个或多个R3基团取代,其中一个或多个非相邻的CH2基团可被R4C=CR4、C≡C、Si(R4)2、C=O、C=NR4、P(=O)(R4)、SO、SO2、NR4、O、S或CONR4代替并且其中一个或多个氢原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,所述环系中的每个可被一个或多个R4基团取代,或具有5至40个芳族环原子且可被一个或多个R3基团取代的芳氧基或杂芳氧基基团,或具有5至40个芳族环原子且可被一个或多个R4基团取代的芳烷基或杂芳烷基基团,或者这些体系的组合;
R4在每种情况下相同或不同,并且是H,D,F,或具有1至20个碳原子的脂族烃基基团或具有5至40个环原子的芳基或杂芳基基团,其可被一个或多个R5基团取代,或这些基团的组合;
R5在每种情况下相同或不同,并且是H、D、F或具有1至20个碳原子的脂族烃基基团;
q在每种情况下是相同或不同并且是0或1;
r是0或1;
p是0或1,其中p≥r;
其中,
Ar1和Ar2不包含任何式(2)的结构:
其中*指示与L1或L2或基本骨架连接的键;并且
选自(L1)qAr1、(L2)qAr2和(L3)q(Ar3)p基团中的至少两个基团是相同的。
在本发明上下文中的芳基基团含有6至60个碳原子;在本发明上下文中的杂芳基基团含有2至60个碳原子和至少一个杂原子,条件是碳原子与杂原子的总和至少为5。所述杂原子优选选自N、O和/或S。芳基基团或杂芳基基团在此被理解为是指简单的芳族环,即苯,或简单的杂芳族环,例如噻吩等,或稠合(缩合)的芳基或杂芳基基团,例如萘、蒽、菲、二苯并呋喃等。相比之下,通过单键彼此连接的芳族体系,例如联苯不被称为芳基或杂芳基基团,而被称为芳族环系。
在本发明上下文中的芳族环系在环系中含有6至80个碳原子。在本发明上下文中的杂芳族环系在环系中含有2至60个碳原子和至少一个杂原子,条件是碳原子与杂原子的总和至少为5。所述杂原子优选选自N、O和/或S。在本发明上下文中的芳族或杂芳族环系被理解为是指如下的体系,其不必仅含有芳基或杂芳基基团,而是其中两个或更多个芳基或杂芳基基团还可以通过非芳族单元(优选小于非H原子的10%),例如碳、氮或氧原子连接。例如,诸如9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚、茋等的体系也应被视为本发明上下文中的芳族环系,同样地其中两个或更多个芳基基团通过例如短的烷基基团连接的体系也是如此。另外,通过单键彼此连接的芳族体系例如联苯也被视为本申请上下文中的芳族环系。
在本发明上下文中的缺电子杂芳基基团被定义为具有至少两个杂原子的5元杂芳基基团,例如咪唑、唑、二唑等,或定义为具有至少一个杂原子的6元杂芳基基团,例如吡啶、嘧啶、吡嗪、三嗪等。另外的6元芳基或6元杂芳基基团也可以稠合到这些基团上,如例如在苯并咪唑或喹啉中的情况。
在本发明的上下文中,通常含有1至40个或2至20个碳原子且其中单独的氢原子或CH2基团还可被上述基团代替的脂族烃基基团或烷基基团或烯基或炔基基团优选被理解为是指甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、正己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基基团。具有1至40个碳原子的烷氧基基团优选被理解为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、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、环己氧基、正庚氧基、环庚氧基、正辛氧基,环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。具有1至40个碳原子的硫代烷基基团被理解为是指尤其是甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基,2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。一般来讲,根据本发明的烷基、烯基、炔基、烷氧基或硫代烷基基团可以是直链、支链或环状的,其中一个或多个非相邻的CH2基团可以被上述基团代替;此外,一个或多个氢原子也可以被D、F、Cl、Br、I、CN或NO2,优选F、Cl或CN,更优选F或CN,尤其优选CN代替。
具有5-80芳族环原子且在每种情况下还可被上述基团取代并且可经由任何期望的位置与芳族或杂芳族体系连接的芳族或杂芳族环系尤其被理解为是指衍生自如下物质的基团:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式-或反式-茚并芴、顺式-或反式-茚并咔唑、顺式-或反式-吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘、4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、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、吲嗪和苯并噻二唑,或来自这些体系的组合的基团。这些基团可各自被上述基团取代。
本发明中限定的芳氧基基团被理解为是指经由氧原子键合的如上限定的芳基基团。类似的定义适用于杂芳氧基基团。
在本发明上下文中的缺电子杂芳基基团被定义为具有至少两个杂原子的5元杂芳基基团,例如咪唑、唑、二唑等,或定义为具有至少一个杂原子的6元杂芳基基团,例如吡啶、嘧啶、吡嗪、三嗪等。另外的6元芳基或6元杂芳基基团也可以稠合到这些基团上,如例如在苯并咪唑或喹啉中的情况。
在本发明的上下文中,两个或更多个基团可以一起形成环的措词应被理解为尤其是指两个基团通过化学键彼此连接。这由以下方案所例示:成环
然而,此外,上述措词也应理解为是指,如果两个基团之一是氢,则第二基团结合至氢原子所键合的位置,从而成环。这将由以下方案所例示:
在本发明的另一个实施方式中,式(1)中的6元环包含不超过一个N作为芳族环原子,意味着仅有一个X、Y或W是N。更优选地,式(1)中的X、Y或W符号中没有一个是N。
式(1)化合物的优选实施方式是下式(3)的化合物:
其中Y在p+r=0时是CR并且在p+r≥0时是C。所用的其它符号和标记对应于式(1)的那些。
在本发明的一个优选实施方式中,所述化合物是下式(4)至(7)之一的化合物:
此处的符号和标记对应于式(3)的符号和标记。
此处优选式(4)和(5)之一的化合物。根据上述定义,本发明化合物的咔唑基本骨架不具有任何另外的稠合到所述基本骨架上的环。其仅在邻位具有一个芳族环系。
在本发明的一个优选实施方式中,R是在每种情况下相同或不同,并且是H、D、F或具有1至20个碳原子的脂族烃基基团,更优选H、D或F。
在本发明的一个优选实施方式中,R1是在每种情况下相同或不同,并且是H、D、F或具有1至20个碳原子的脂族烃基基团,更优选H、D或F,最优选H或D。
在本发明的一个优选实施方式中,Ar1和Ar2基团在每种情况下选自具有下式(Ar-1)至(Ar-14)的基团:
其中的符号和标记对应于式(1)的符号和标记,并且此外:
Q在每种情况下相同或不同并且是CR2或N,其中每个环不超过3个Q是N;
E在每种情况下相同或不同并且是(CR2)2、NR2、O、S或C=O;
G在每种情况下是单键、(CR2)2、NR2、O、S或C=O;
n是0或1,其中n=0是指在该位置处没有键合E基团,而是R2基团键合至相应的碳原子;并且
*表示与L1或L2或基本骨架连接的键。
在本发明的另一个实施方式中,Ar3和Ar4基团在每种情况下相同或不同,并且选自式(Ar-1)至(Ar-14)和下式(Ar-15)至(Ar-19):
其中的符号和标记对应于式(1)的符号和标记,并且此外,对于式(Ar-15)至(Ar-19):
Q在每种情况下相同或不同并且是CR2或N,其中每个环不超过2个Q符号是N;
E在每种情况下相同或不同并且是(CR2)2、NR2、O、S或C=O;
G在每种情况下是单键、(CR2)2、NR2、O、S或C=O;
n是0或1,其中n=0是指在该位置处没有键合E基团,而是R2基团键合至相应的碳原子;并且
*在Ar3的情况下表示与L3或基本骨架连接的键,在Ar4的情况下表示与L4连接的键。
在本发明的另一个优选实施方式中,Ar1、Ar2、Ar3或Ar4基团中的至少一个选自式(Ar-1)、(Ar-5)、(Ar-6)、(Ar-8)或(Ar-10)之一,优选选自式(Ar-1-2)、(Ar-1-3)、(Ar-1-4)、(Ar-1-5)、(Ar-5)、(Ar-6)、(Ar-8)或(Ar-10)之一。
在本发明的另一个特别优选的实施方式中,Ar1、Ar2、Ar3或Ar4基团中的至少一个包含缺电子杂芳基基团。优选地,Ar1、Ar2、Ar3或Ar4基团中的至少一个选自式(Ar-1-2)、(Ar-1-3)、(Ar-1-4)和(Ar-1-5)之一,更优选选自式(Ar-1-2)和(Ar-1-5)之一。
在本发明的另一个特别优选的实施方式中,Ar1、Ar2、Ar3或Ar4基团中的至少一个选自式(Ar-5)、(Ar-6)、(Ar-8)和(Ar-10)之一。
在另一个优选实施方式中,在式(Ar-1)中,0、2或3个Q符号是N。
式(Ar-8)的优选实施方式通过下式(Ar-8-1)至(Ar-8-7)示出:
其中的符号对应于式(Ar-8)的符号。更优选地,Q总是CR2。
在另一个优选实施方式中,Ar1和Ar2基团在每种情况下相同或不同,并且选自具有式(Ar-1)至(Ar-14)、优选式(Ar-1)至(Ar-13)的结构的基团,其中,所述通式被下式(Ar-1-1)至(Ar-13-1)的各自的特别优选的实施方式代替(例如,式(Ar-1)被式(Ar-1-1)至(Ar-1-9)之一代替):
其中的符号对应于式(1)中的符号。所述式可在自由位置处被R2取代。
在本发明的另一个实施方式中,Ar3和Ar4基团在每种情况下相同或不同并且选自式(Ar-1)至(Ar-14),优选选自式(Ar-1)至(Ar-13),或优选的式(Ar-1-1)至(Ar-13-1),以及以下优选的式(Ar-15-1)至(Ar-19-4):
其中的符号对应于式(Ar-15)至(Ar-19)中的符号。所述式可在自由位置处被R2取代。
在本发明的另一个实施方式中,式(Ar-8)或其优选实施方式的基团选自式(Ar-8-1-1a)至(Ar-8-7-6a)之一的基团:
其中的符号对应于式(1)中的符号。所述式可在自由位置处被R2取代。
在本发明的另一个特别优选的实施方式中,至少一个Ar1、Ar2、Ar3或Ar4基团选自式(Ar-8-1-1)至(Ar-8-7-6)之一,优选选自式(Ar-8-1-1a)至(Ar-8-7-6a)之一。
当存在一个或多个L1、L2、L3和/或L4基团时,它们优选是如下的二价芳族或杂芳族环系,所述环系具有6至24个芳族环原子,优选不含任何具有超过两个彼此直接稠合的六元环的稠合芳基或杂芳基基团。优选的L1、L2、L3和/或L4基团相同或不同并且选自邻-、间-或对-苯,邻-、间-或对-联苯,三联苯(尤其是邻-、间-或对-三联苯),四联苯(尤其是邻-、间-或对四联苯),芴,9,9'-螺二芴,呋喃,苯并呋喃,二苯并呋喃,二苯并噻吩,吡咯,吲哚或咔唑,其中在咔唑的情况下与所述基本骨架连接的二价键不经由氮原子连接。这些基团可以被一个或多个R2基团取代,但优选是未取代的。当L1、L2、L3和/或L4是芴时,它们优选在9位被两个各自具有1至10个碳原子的烷基基团取代。
在本发明的另一个实施方式中,L1、L2、L3和/或L4基团选自式(Ar2-1)至(Ar2-12):
其中用于式(1)的符号具有给定的定义,由*标识的键指示与基本骨架连接的键,由**标识的键指示与相应的Ar1、Ar2、Ar3或Ar4基团连接的键。所述基团可在自由位置处被R2取代。它们优选是未取代的。
在本发明的一个实施方式中,选自(L1)qAr1、(L2)qAr2和(L3)qAr3基团的至少两个基团是相同的。优选地,(L1)qAr1和(L2)qAr2基团是相同的。
在本发明的另一个实施方式中,式(1)的化合物不包含两个二苯并呋喃衍生物和/或二苯并噻吩衍生物。这些可以是未取代的二苯并呋喃(例如式(Ar-5-17)、(Ar-5-18)、(Ar-5-19)、(Ar-5-20)、(Ar2-8))或取代的二苯并呋喃(例如式(Ar-6-13)、(Ar-6-14)、(Ar-6-15)、(Ar-6-16))。可选地,二苯并呋喃结构可以是稠合杂芳族环系的一部分(例如式(Ar-8-1-2)、(Ar-8-4-2)、(Ar-8-5-2)(Ar-8-6-2)、(Ar-8-7-2))。这些可以是取代的二苯并噻吩(例如式(Ar-5-13)(Ar-5-14)、(Ar-5-15)、(Ar-5-16))或取代的二苯并噻吩(例如式(Ar-6-9)、(Ar-6-10)、(Ar-6-11)、(Ar-6-12)、(Ar2-7))。可选地,二苯并噻吩结构可以是稠合杂芳族环系的一部分(例如式(Ar-8-1-3)、(Ar-8-2-3)、(Ar-8-4-3)、(Ar-8-5-3)、(Ar-8-6-3)或(Ar-8-7-3))。
在本发明的另一个实施方式中,Ar1和Ar2基团在每种情况下相同或不同并且选自式(Ar-1)至(Ar-14),优选(Ar-1)至(Ar-13)或它们的优选实施方式,并且当存在Ar3和Ar4基团时,它们相同或不同并且选自式(Ar-1)至(Ar-19)或它们的优选实施方式,并且当存在L1、L2、L3和/或L4基团时,它们相同或不同并且选自式(Ar2-1)至(Ar2-12)。
在本发明的一个优选实施方式中,R2在每种情况下相同或不同并且选自H,D,F,Si(R3)3,CN,具有1至10个碳原子的直链烷基或烷氧基基团或具有3至10个碳原子的支链或环状的烷基或烷氧基基团,所述基团中的每个可被一个或多个R3基团取代,其中一个或多个非相邻的CH2基团可被O代替并且其中一个或多个氢原子可被D或F代替,具有6至60个芳族环原子且在每种情况下可被一个或多个R3基团取代的芳族或杂芳族环系,其中两个或更多个相邻的R2取代基可任选地形成可被一个或多个R3基团取代的单环或多环的脂族环系。
在本发明的一个特别优选的实施方式中,R2在每种情况下相同或不同并且选自H,D,F,具有1至10个碳原子的直链烷基基团或具有3至10个碳原子的支链或环状的烷基基团,所述基团中的每个可被一个或多个R3基团取代,具有6至60个碳原子且在每种情况下可被一个或多个R3基团取代的芳族或杂芳族环系,其中两个或更多个相邻的R2取代基可任选地形成可被一个或多个R3基团取代的单环或多环的脂族环系。
在另一个优选实施方式中,如例如在式(Ar-5-1)、(Ar-5-2)、(Ar-5-3)、(Ar-5-4)、(Ar-6-1)、(Ar-6-2)、(Ar-6-3)、(Ar-6-4)、(Ar-8-3-1)、(Ar-11-1)、(Ar-18-1)或(Ar2-8b)的情况,结合至芳族或杂芳族环系中的碳桥连基的R2在每种情况下相同或不同,并且选自具有1至10个碳原子的直链烷基基团,具有3至10个碳原子的支链或环状的烷基基团或具有6至30个碳原子的芳族环系,其为如上限定的且可被一个或多个R3基团取代。在这种情况下,所述两个R2基团可彼此形成环系,所述环系可以脂族的,或者除上面给出的R2的定义外也可以是芳族的。成环形成螺环体系。
在另一个优选的实施方式中,结合至氮原子的R2选自具有1至10个碳原子的直链烷基基团,具有3至10个碳原子的支链或环状的烷基基团或具有6至30个碳原子的芳族环系,尤其是具有6至24个碳原子的芳族环系,其为如上限定的且可被一个或多个R3基团取代。
上述实施方式可以根据需要彼此组合。更特别地,优选将上面详述的优选实施方式彼此组合。
上面详述的实施方式的优选化合物或优选用于有机电子器件中的化合物的实例是以下化合物:
可以通过本领域技术人员已知的合成步骤例如溴化、Suzuki偶联、Ullmann偶联、Hartwig-Buchwald偶联等制备本发明的化合物。
例如,从任选具有另外取代的1,3,5-三溴苯开始进行本发明化合物的合成。除了溴,也可以使用其它的反应性离去基团,例如碘、氯或三氟甲磺酸酯。在这种情况下,该化合物在两个位置处与相应的(L1)qAr1和(L2)qAr2基团偶联。尤其适用于此目的的是过渡金属催化的偶联反应(例如Suzuki偶联或Stille偶联)。为了这个目的,待偶联的基团也必须具有相应的合适的离去基团,尤其是氯、溴、碘、三氟甲磺酸酯或硼酸衍生物,尤其是硼酸或硼酸酯。
在下一个步骤中,于是可以使至少二取代的苯衍生物与另外的在邻位带有硝基基团的芳族化合物通过进一步的偶联反应反应到偶联位置上。由此得到的硝基联苯衍生物然后可以进行环化,从而得到咔唑基本骨架。在进一步的步骤中,通过进一步的偶联反应,可以在咔唑的氮原子上引入基团(例如Buchwald偶联或Ullmann偶联)。此外,还可以通过选择性溴化和随后的偶联引入另外的基团。
因此,本发明还提供了制备式(1)化合物的方法,其中通过一种或多种偶联反应和/或环化形成所述式(1)的化合物。
以上所示的合成方法有例示性的特点,并且如果有利于本发明化合物的特定实施方式的合成,则可以由有机合成领域的本领域技术人员以合适的方式进行修改。
本发明的上述化合物,尤其是被反应性离去基团例如溴、碘、氯、硼酸或硼酸酯取代的化合物,可以用作生产相应的低聚物、树枝状大分子或聚合物的单体。合适的反应性离去基团例如是溴,碘,氯,硼酸,硼酸酯,胺,具有末端C-C双键或C-C三键的烯基或炔基基团,环氧乙烷,氧杂环丁烷,经历环加成例如1,3-偶极环加成的基团,例如二烯或叠氮化物,羧酸衍生物,醇和硅烷。
因此,本发明还提供含有一种或多种式(1)化合物的低聚物、聚合物或树枝状大分子,其中一个或多个与所述聚合物、低聚物或树枝状大分子连接的键可以位于式(1)中的任何自由位置处。根据本发明化合物的连接,所述化合物是所述低聚物或聚合物的侧链的一部分或主链的一部分。
在本发明上下文中的低聚物被理解为是指由至少三个单体单元形成的化合物。在本发明上下文中的聚合物被理解为是指由至少十个单体单元形成的化合物。
本发明的聚合物、低聚物或树枝状大分子可以是共轭的,部分共轭或非共轭的。本发明的低聚物或聚合物可以是直链的、支链的或树枝状的。
在具有线性连接的结构中,式(1)的单元可以彼此直接连接或者它们可以通二价基团,例如通过取代或未取代的亚烷基基团,通过杂原子或通过二价芳族或杂芳族基团彼此连接。
在支链和树枝状的结构中,3、5或更多个式(1)的单元可以例如通过三价或更高价的基团,例如通过三价或更高价的芳族或杂芳族基团连接,从而给出支链或树状的低聚物或聚合物。
对于在低聚物、树枝状大分子和聚合物中的式(1)重复单元,如上关于本发明的化合物描述的相同优选方式适用。
为了制备低聚物或聚合物,将本发明的单体均聚或与另外的单体共聚。合适且优选的共聚单体选自芴(例如根据EP842208或WO00/22026)、螺二芴(例如根据EP707020、EP894107或WO06/061181)、对亚苯基(例如根据WO1992/18552)、咔唑(例如根据WO04/070772或WO2004/113468)、噻吩(例如根据EP1028136)、二氢菲(例如根据WO2005/014689或WO2007/006383)、顺式-和反式-茚并芴(例如根据WO2004/041901或WO2004/113412)、酮(例如根据WO2005/040302)、菲(例如根据WO2005/104264或WO2007/017066)或者多个这些单元。所述聚合物、低聚物和树枝状大分子通常还含有另外的单元,例如发光(荧光或磷光)单元,例如乙烯基三芳基胺(例如根据WO2007/068325)或磷光金属络合物(例如根据WO2006/003000),和/或电荷传输单元,尤其是基于三芳基胺的那些。
本发明的聚合物、低聚物和树枝状大分子具有有利的性质,尤其是长寿命、高效率和良好的色坐标。
通常通过一种或多种单体类型的聚合来制备本发明的聚合物和低聚物,所述一种或多种单体类型中的至少一种单体产生聚合物中式(1)的重复单元。适合的聚合反应对本领域技术人员是已知的并且描述在文献中。特别适合和优选的产生C-C和C-N键的聚合反应如下:
(A)SUZUKI聚合;
(B)YAMAMOTO聚合;
(C)STILLE聚合和
(D)HARTWIG-BUCHWALD聚合。
如何可通过这些方法进行聚合和然后如何可从反应介质中分离聚合物和进行纯化对于本领域技术人员是已知的并且详细描述于文献中,例如描述于WO2003/048225、WO2004/037887和WO2004/037887中。
因此本发明还提供制备本发明的聚合物、低聚物和树枝状大分子的方法,所述方法的特征在于它们是通过根据SUZUKI的聚合、根据YAMAMOTO的聚合、根据STILLE的聚合或根据HARTWIG-BUCHWALD的聚合来制备的。可以通过本领域技术人员已知的方法或与其类似地制备本发明的树枝状大分子。适合的方法描述于文献中,例如描述于Frechet,JeanM.J.;Hawker,Craig J.,“Hyperbranched polyphenylene and hyperbranchedpolyesters:newsoluble,three-dimensional,reactive polymers(超支化聚亚苯基和超支化聚酯:新可溶三维反应性聚合物)”,Reactive&Functional Polymers(反应性与功能性聚合物)(1995),26(1-3),127-36;Janssen,H.M.;Meijer,E.W.,“The synthesis andcharacterization of dendritic molecules(树枝状分子的合成和表征)”,MaterialsScience and Technology(材料科学和技术)(1999),20(Synthesis of Polymers(聚合物的合成)),403-458;Tomalia,Donald A.,“Dendrimer molecules(树枝状分子)”,Scientific American(科学美国人)(1995),272(5),62-6;WO2002/067343A1和WO2005/026144A1中。
为了从液相例如通过旋涂或通过印刷方法处理本发明的化合物,需要本发明化合物的制剂。这些制剂可以例如是溶液、分散体或乳液。为此,可以优选使用两种或更多种溶剂的混合物。合适且优选的溶剂例如是甲苯,苯甲醚,邻二甲苯、间二甲苯或对二甲苯,苯甲酸甲酯,均三甲苯,萘满,邻二甲氧基苯,THF,甲基-THF,THP,氯苯,二烷,苯氧基甲苯、尤其是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-甲基苯并噻唑,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,苯并噻唑,苯甲酸丁酯,异丙苯,环己醇,环己酮,环己基苯,十氢化萘,十二烷基苯,苯甲酸乙酯,茚满,苯甲酸甲酯,NMP,对甲基异丙基苯,苯乙醚,1,4-二异丙基苯,二苄醚,二乙二醇丁甲醚,三乙二醇丁甲醚,二乙二醇二丁醚,三乙二醇二甲醚,二乙二醇单丁醚,三丙二醇二甲醚,四乙二醇二甲醚,2-异丙基萘,戊基苯,已基苯,庚基苯,辛基苯,1,1-双(3,4-二甲基苯基)乙烷,或这些溶剂的混合物。
因此本发明还提供制剂,尤其是溶液、分散体或乳液,其包含至少一种式(1)的化合物或至少一种含有至少一种式(1)单元的聚合物、低聚物或树枝状大分子,和至少一种溶剂、优选有机溶剂。可制备这种溶液的方式对于本领域技术人员是已知的,并且在例如WO2002/072714、WO2003/019694及其中引用的文献中进行了描述。
本发明还提供如下的混合物,其包括至少一种本发明的化合物和至少一种另外的化合物。在本发明的化合物被用作基质材料时,所述另外的化合物可以例如是荧光或磷光掺杂剂,尤其是磷光掺杂剂。合适的掺杂剂结合有机电致发光器件在下面详细描述并且对于本发明的混合物也是优选的。
本发明的化合物和混合物适合用于电子器件中。电子器件被理解为是指如下的器件,其含有至少一个含有至少一种有机化合物的层。这种组件也可以包含无机材料或完全由无机材料形成的层。
因此本发明还提供本发明的化合物或混合物在电子器件,尤其是在有机电致发光器件中的用途。
本发明还进一步提供电子器件,其包含本发明的上面详述的化合物或混合物中的至少一种。在这种情况下,所述化合物的上面详述的优选方式也适于所述电子器件。
所述电子器件优选选自有机电致发光器件(OLED、PLED)、有机集成电路(O-IC)、有机场效应晶体管(O-FET)、有机薄膜晶体管(O-TFT)、有机发光晶体管(O-LET)、有机太阳能电池(O-SC)、有机染料敏化太阳能电池、有机光学检测器、有机光感受器、有机场猝熄器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-laser)和有机等离子体发射器件(D.M.Koller等,Nature Photonics(自然光子学)2008,1-4),优选有机电致发光器件(OLED、PLED),尤其是磷光OLED。
所述有机电致发光器件包含阴极、阳极和至少一个发光层。除了这些层之外,它也可以包含另外的层,例如在每种情况下一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。同样可以在两个发光层之间引入例如具有激子阻挡功能的中间层。然而,应当指出,这些层中的每一个未必都需要存在。在这种情况下,所述有机电致发光器件可含有一个发光层,或者它可含有多个发光层。如果存在多个发光层,则这些优选具有总共多个在380nm与750nm之间的发光峰值,使得总体结果是白色发光;换句话说,在发光层中使用可以发荧光或发磷光的多种发光化合物。尤其优选具有三个发光层的体系,其中所述三个发光层显示蓝色、绿色和橙色或红色发光(对于基本结构,参见例如WO2005/011013)。这些可以是荧光或磷光发光层或其中将荧光和磷光发光层彼此组合的混合体系。
根据确切的结构,根据上面详述的实施方式的本发明化合物可以用于不同的层中。优选如下的有机电致发光器件,根据确切的取代,所述有机电致发光器件包含式(1)或根据优选实施方式的化合物作为荧光或磷光发光体、尤其是磷光发光体的基质材料,和/或在电子传输层中和/或在电子阻挡或激子阻挡层中和/或在空穴传输层中包含式(1)或根据优选实施方式的化合物。在这种情形下,上面详述的优选实施方式也适用于所述材料在有机电子器件中的使用。
在本发明的一个优选实施方式中,式(1)或根据优选实施方式的化合物被用作发光层中荧光或磷光化合物、尤其是磷光化合物的基质材料。在这种情况中,所述有机电致发光器件可以含有一个发光层,或者它可以含有多个发光层,其中至少一个发光层含有至少一种本发明的化合物作为基质材料。
本发明的另一个优选实施方式是将式(1)或根据优选实施方式的化合物作为磷光发光体的基质材料与另外的基质材料组合使用。可以与式(1)或根据优选实施方式的化合物组合使用的特别适合的基质材料是芳族酮,芳族氧化膦或芳族亚砜或砜,例如根据WO2004/013080、WO2004/093207、WO2006/005627或WO2010/006680的,三芳基胺,咔唑衍生物,例如CBP(N,N-双咔唑基联苯)或在WO2005/039246、US2005/0069729、JP2004/288381、EP1205527或WO2008/086851中公开的咔唑衍生物,吲哚并咔唑衍生物,例如根据WO2007/063754或WO2008/056746的,茚并咔唑衍生物,例如根据WO2010/136109或WO2011/000455的,氮杂咔唑衍生物,例如根据EP1617710、EP1617711、EP1731584、JP2005/347160的,双极性基质材料,例如根据WO2007/137725的,硅烷,例如根据WO2005/111172的,氮杂硼杂环戊二烯或硼酸酯,例如根据WO2006/117052的,三嗪衍生物,例如根据WO2010/015306、WO2007/063754或WO2008/056746的,锌络合物,例如根据EP652273或WO2009/062578的,二氮杂硅杂环戊二烯或四氮杂硅杂环戊二烯衍生物,例如根据WO2010/054729的,二氮杂磷杂环戊二烯衍生物,例如根据WO2010/054730的,桥连咔唑衍生物,例如根据US2009/0136779、WO2010/050778、WO2011/042107、WO2011/088877的或根据未公布的申请EP11003232.3的,苯并菲衍生物,例如根据WO2012/048781的,或内酰胺,例如根据WO2011/116865或WO2011/137951的。在混合物中同样可以存在另外的以比实际发光体更短的波长发光的磷光发光体作为共主体。
基于发光体和基质材料的总混合物,式(1)或根据优选实施方式的化合物和所述发光化合物的混合物含有在99体积%和1体积%之间、优选在98体积%和10体积%之间、更优选在97体积%和60体积%之间、尤其在95体积%和80体积%之间的式(1)或根据优选的实施方式的化合物。相应地,基于发光体和基质材料的总混合物,所述混合物含有在1体积%和99体积%之间、优选在2体积%和90体积%之间、更优选在3体积%和40体积%之间、尤其是在5体积%和20体积%之间的发光体。
术语“磷光掺杂剂(发光体)”通常涵盖其中经由自旋禁阻跃迁、例如从激发三重态或具有更高自旋量子数的状态例如五重态的跃迁来实现发光的化合物。
合适的磷光掺杂剂尤其是如下的化合物,其在适当激发时发光、优选在可见区发光,并且另外含有至少一个原子序数大于20、优选大于38且小于84、更优选大于56且小于80的原子。优选使用含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,尤其是含有铱、铂或铜的化合物作为磷光掺杂剂。
在本发明的上下文中,所有发光的铱、铂或铜络合物都被视为磷光化合物。
磷光掺杂剂的实例可见于申请WO2000/70655、WO2001/41512、WO2002/02714、WO2002/15645、EP1191613、EP1191612、EP1191614、WO2005/033244、WO2005/019373和US2005/0258742中。一般来说,根据现有技术用于磷光OLED和在有机电致发光器件领域中为本领域技术人员所知的所有磷光络合物都适合用于本发明的器件中。本领域技术人员还能够在无需运用创造性技巧的情况下,将另外的磷光络合物与本发明的化合物组合用于OLED中。
在本发明的另一个实施方式中,本发明的有机电致发光器件不含任何单独的空穴注入层和/或空穴传输层和/或空穴阻挡层和/或电子传输层,意味着所述发光层直接邻接空穴注入层或阳极,和/或所述发光层直接邻接电子传输层或电子注入层或阴极,如例如在WO2005/053051中所述的。另外可以使用与发光层中的金属络合物相同或类似的金属络合物作为直接邻接发光层的空穴传输或空穴注入材料,如例如在WO2009/030981中所述的。
另外可以将本发明的化合物用于空穴传输层中或用于空穴注入层中或用于激子或电子阻挡层中。
在本发明的有机电致发光器件的另外的层中,可以使用根据现有技术通常使用的任何材料。因此,本领域技术人员能够在无需运用创造性技巧的情况下将已知用于有机电致发光器件的任何材料与式(1)或根据优选实施方式的本发明化合物组合使用。
另外优选如下的有机电致发光器件,其特征在于通过升华方法涂布一个或多个层。在这种情况下,在真空升华体系中,在通常小于10-5毫巴、优选小于10-6毫巴的初始压力下通过气相沉积施加所述材料。所述初始压力也可以甚至更低或更高,例如小于10-7毫巴。
同样优选如下的有机电致发光器件,其特征在于通过OVPD(有机气相沉积)方法或借助于载气升华来涂布一个或多个层。在这种情况下,在10-5毫巴和1巴之间的压力下施加所述材料。这种方法的特例是OVJP(有机蒸气喷印)方法,其中所述材料通过喷嘴直接施加并且因此是被结构化的(例如M.S.Arnold等,Appl.Phys.Lett.(应用物理快报)2008,92,053301)。
另外优选如下的有机电致发光器件,其特征在于从溶液中,例如通过旋涂,或通过任何印刷方法,例如喷墨印刷、LITI(光诱导热成像,热转印)、丝网印刷、柔性版印刷、平版印刷或喷嘴印刷,来产生一个或多个层。为了这个目的,需要可溶性化合物,例如通过合适的取代获得所述可溶性化合物。这些方法尤其也适合于低聚物、树枝状大分子和聚合物。
此外,其中例如从溶液中施加一个或多个层并通过气相沉积施加一个或多个另外的层的混合方法也是可行的。例如,可以从溶液中施加发光层,并可以通过气相沉积施加电子传输层。
这些方法对于本领域技术人员通常是已知的并且可由本领域技术人员在无需运用创造性技巧的情况下应用至包含本发明化合物的有机电致发光器件。
在用于有机电致发光器件中时,本发明的化合物相比于现有技术具有如下令人惊讶的优点中的一个或多个:
1.与根据现有技术的体系相比,相应器件的功率效率更高。
2.与根据现有技术的体系相比,相应器件的稳定性更高,这具体体现在长得多的寿命上。
3.本发明的有机电致发光器件具有降低的工作电压。
4.当本发明的化合物被用作磷光发光体的基质材料时,在区域中仅有小于10体积%的低的发光体浓度时已经可以达到非常良好的结果。
5.本发明的化合物具有非常好的热稳定性。
现在通过以下实施例详细地说明本发明,而没有任何意图由此对其进行限制。
实施例
A)合成实施例
除非另外说明,否则在保护性气体气氛下在干燥溶剂中进行以下合成。溶剂和试剂可购自例如Sigma-ALDRICH或ABCR。对于从文献中已知的化合物,在每种情况下也报道了相应的CAS编号。
实施例1:3,3-(5-氯-1,3-亚苯基)双[9-苯基-9H-咔唑]
将50g(182mmol)的1,3-二溴-5-氯苯、143g(388mmol)的苯基硼酸和78g(369mmol)的磷酸钾悬浮于250mL水和500mL二烷中。将830mg(3.6mmol)的Pd(OAc)2和3.3g(11mmol)的P(o-Tol)3加入到该悬浮液中,并将所述反应混合物在回流下加热16小时。随后将所述混合物在乙酸乙酯和水之间进行分配,并将有机相用水洗涤三次,经Na2SO4干燥并通过旋转蒸发浓缩。将留下的残余物从庚烷/甲苯中重结晶。产率为104g(175mmol,95%)。
以类似的方式,可以获得以下化合物:
实施例2:3,3-[5(4,4,5,5-四甲基-[1,3,2]二氧杂硼戊环基-2基)-1,3-亚苯基]双[9-苯基-9H-咔唑]
将75g(126mmol)的3,3-(5-氯-1,3-亚苯基)双[9-苯基-9H-咔唑]、41g(163mmol)的双(频哪醇根合)二硼和18g(25mmol)的三环己基膦二氯化钯和21g(214mmol)的乙酸钾悬浮于1200mL二烷中。将所述反应混合物在130℃回流下加热16小时。随后将所述混合物在乙酸乙酯和水之间进行分配,并将有机相用水洗涤三次,经Na2SO4干燥并通过旋转蒸发浓缩。将留下的残余物从庚烷/甲苯中重结晶。产率为76g(110mmol,88%)。
以类似的方式,可以获得以下化合物:
实施例3:与1-溴-2-硝基苯的反应
将46g(67mmol)的3,3-[5-(4,4,5,5-四甲基-[1,3,2]二氧杂硼戊环基-2基)-1,3-亚苯基]双[9-苯基-9H-咔唑]、16g(81mmol)的1-溴-2-硝基苯和152mg(0.67mmol)的Pd(OAc)2和178mg(0.67mmol)的P(o-Tol)3以及136g(980mmol)的碳酸钾悬浮在1000mL的THF和300mL的水中。将所述反应混合物在130℃回流下加热16小时。随后将所述混合物在乙酸乙酯和水之间进行分配,并将有机相用水洗涤三次,经Na2SO4干燥并通过旋转蒸发浓缩。将留下的残余物从庚烷/甲苯中重结晶。产率为42g(62mmol,91%)。
以类似的方式,可以获得以下化合物:
实施例4:9,9”-二苯基-9H,9’H,9”H-[3,1’;3’,3”]三咔唑
将40g(59mmol)的适当硝基芳族化合物和239mL(1400mmol)的亚磷酸三乙酯的混合物在130℃回流下加热12小时。随后将亚磷酸三乙酯的剩余部分蒸出(72-76℃/9mmHg)。将水/甲醇(1:1)添加至残余物,并将固体滤出并重结晶。产率为38克(58mol,99%)。
以类似的方式,可以获得以下化合物:
实施例5:9,9’,9”-三苯基-9H,9’H,9”H-[3,1’;3’,3”]三咔唑
将25g(38mmol)的9,9”-二苯基-9H,9’H,9”H-[3,1’;3’,3”]三咔唑和7g(46mmol)溴苯溶解在450mL甲苯中并通过保护气体入口进行脱气。在此之后加入7mL(7mmol,1M的甲苯溶液)的三-叔丁基膦、633.8mg(2.82mmol)的Pd(OAc)2和7g(76mmol)的NaOtBu。将固体预先脱气,并将反应混合物进行后脱气,然后在回流下搅拌3小时。将温热的反应溶液通过Alox B(活性水平1)过滤,用水洗涤,干燥并浓缩。产率为27g(37mol,98%)。
以类似的方式,可以获得以下化合物:
实施例6:6-溴-1,3-二苯基-9H-咔唑
将12.7g(40mmol)1,3-二苯基-9H-咔唑悬浮在450mL乙腈中,并在-20℃下以使得反应温度不上升到超过-20℃的方式按份添加7.15g(40mmol)的N-溴代琥珀酰亚胺。将所述混合物搅拌另外18小时,在所述搅拌过程中,所述反应混合物升温至室温。然后将所述反应混合物通过旋转蒸发浓缩,溶于二氯甲烷中并用水洗涤。将所述混合物干燥、浓缩,然后从甲苯中重结晶两次。产率为12g(30mol,76%)。
以类似的方式,可以获得如下的化合物:
实施例7:1,3-二苯基-6-(4,4,5,5-四甲基-[1,3,2]二氧杂硼戊环-2基)-9H-咔唑
将50g(125mmol)的6-溴-1,3-二苯基-9H-咔唑、40g(161mmol)的双(频哪醇根合)二硼和18g(25mmol)的三环己基膦二氯化钯和21g(214mmol)的乙酸钾悬浮在1200mL二烷中。将所述反应混合物在130℃回流下加热16小时。随后将所述混合物在乙酸乙酯和水之间进行分配,并将有机相用水洗涤三次,经Na2SO4干燥并通过旋转蒸发浓缩。将留下的残余物从庚烷/甲苯中重结晶。产率为42g(62mmol,91%)。
以类似的方式,可以获得以下化合物:
实施例8:6-(4-二苯并呋喃-4-基苯基)-1,3-二苯基-9H-咔唑
将30g(68mmol)的1,3-二苯基-6-(4,4,5,5-四甲基-[1,3,2]二氧杂硼戊环-2基)-9H-咔唑、26g(81mmol)的4-(4-溴苯基)二苯并呋喃和152mg(0.67mmol)的Pd(OAc)2和178mg(0.67mmol)的P(o-Tol)3以及136g(980mmol)的碳酸钾悬浮在1000mL THF和300mL水中。将所述反应混合物在130℃回流下加热16小时。随后将所述混合物在乙酸乙酯和水之间进行分配,并将有机相用水洗涤三次,经Na2SO4干燥并通过旋转蒸发浓缩。将留下的残余物从庚烷/甲苯中重结晶。产率为34g(60mmol,90%)。
以类似的方式,可以获得以下化合物:
实施例9:
与实施例5类似,可以使用相应的咔唑衍生物来制备以下化合物:
与实施例5类似,可以使用0.5当量的相应咔唑衍生物来制备以下化合物:
OLED的制造
在下面的实施例C1至I20(参见表2和3)中,给出了各种OLED的数据。
实施例C1-I20的预处理
对为了改进的加工而涂布有50nm厚度的结构化ITO(氧化铟锡)的玻璃板用20nm的PEDOT:PSS(聚(3,4-亚乙基二氧噻吩)聚(苯乙烯磺酸酯),作为CLEVIOSTM P VP AI4083从德国贺利氏贵金属公司(Heraeus Precious Metals GmbH)购买,从水溶液旋涂)进行涂布。这些涂布的玻璃板形成施加OLED的基底。
OLED基本上具有以下层结构:基底/空穴传输层(HTL)/任选的中间层(IL)/电子阻挡层(EBL)/发光层(EML)/任选的空穴阻挡层(HBL)/电子传输层(ETL)/任选的电子注入层(EIL)和最后的阴极。所述阴极由厚度为100nm的铝层形成。OLED的确切结构可见于表2中。制造OLED所需的材料示于表1中。
在真空室中通过热气相沉积施加全部材料。在这种情况下,发光层总是由至少一种基质材料(主体材料)和发光掺杂剂(发光体)构成,所述发光掺杂剂通过共蒸发以一定的体积比加入到所述一种或多种基质材料中。以诸如ST2:L1:TEG1(55%:35%:10%)的形式给出的细节在此是指材料ST2在层中以60体积%的比例存在,L1在层中以35%的比例存在,且TEG1在层中以10%的比例存在。类似地,电子传输层也可以由两种材料的混合物构成。
通过标准方式对OLED进行表征。为此目的,确定电致发光光谱,电流效率(以cd/A计量),功率效率(以Im/W计量)和外量子效率(EQE,以百分比计量),其作为亮度的函数从呈现郎伯发射特性的电流-电压-亮度特性线(IUL特性线)进行计算,以及确定寿命。在1000cd/m2的亮度下确定电致发光光谱,并由此计算CIE 1931x和y色坐标。表3中的参数U1000是指1000cd/m2的亮度所需要的电压。CE1000和PE1000分别指在1000cd/m2下实现的电流和功率效率。最后,EQE1000是指在1000cd/m2的工作亮度下的外量子效率。寿命LT被定义为这样的时间:在以恒定电流工作过程中亮度在该时间后从初始亮度降至特定比例L1。表3中的标志L0、j0=4000cd/m2和L1=70%是指在LT列中报道的寿命对应于如下的时间:在该时间后初始亮度从4000cd/m2下降到2800d/m2。类似地,L0、j0=20mA/cm2、L1=80%是指在20mA/cm2下工作时,在时间LT后亮度降至其初始值的80%。
将各种OLED的数据总结于表3中。实施例C1和C2是根据现有技术的比较例,实施例I1至I20显示了本发明OLED的数据。
为了说明本发明的OLED的优点,下面更详细地阐释实施例中的一些。
本发明的混合物在磷光OLED的空穴传输层中的用途
当本发明的材料在磷光OLED中用作电子阻挡层(EBL)时,相比于现有技术,在所有参数方面,特别是关于电压、外量子效率和功率效率,产生了显著的改进。与现有技术PA1和PA2相比,通过使用本发明的化合物e4和f4,可以观察到约20%-40%的电压的改进,和约25%的外功率效率的改进。功率效率比现有技术改进了约40%(实施例C1、I1和C2、I2)。
表1 用于OLED的材料的结构式
表2 OLED的结构
表3 OLED的数据
Claims (8)
1.式(3)的化合物
其中使用的符号和标记如下:
Y在p+r=0时是CR并且在p+r≥0时是C;
L1、L2、L3在每种情况下相同或不同并且是具有6至24个芳族环原子且可被一个或多个R2基团取代的二价芳族或杂芳族环系;
L4是具有6至24个芳族环原子且可被一个或多个R2基团取代的二价芳族环系;
Ar1、Ar2、Ar3在每种情况下是具有6至60个芳族环原子且在每种情况下还可被一个或多个R2基团取代的芳族或杂芳族环系;
Ar4是具有6至60个芳族环原子且还可被一个或多个R2基团取代的芳族环系;
Ar在每种情况下相同或不同并且是具有5至40个芳族环原子的芳族或杂芳族环系;
R在每种情况下相同或不同并且是H或D;
R1是H或D;
R2在每种情况下相同或不同并且是H,D,F,N(Ar)2,具有1至10个碳原子的直链烷基基团或具有3至10个碳原子的支链或环状的烷基基团,其中一个或多个氢原子可被D或F代替,或具有6至60个芳族环原子的芳族环系,所述环系中的每个可被一个或多个R3基团取代;
R3在每种情况下相同或不同并且是H,D,F,具有1至40个碳原子的直链烷基基团或具有3至40个碳原子的支链或环状的烷基基团,其中一个或多个氢原子可被D或F代替;
q在每种情况下相同或不同并且是0或1;
r是0或1;
p是0或1,其中p≥r;
其中,
Ar1和Ar2不包含任何式(2)的结构:
其中*指示与L1或L2或基本骨架连接的键;
X在每种情况下相同或不同并且是CR或N;并且
选自(L1)qAr1、(L2)qAr2和(L3)r(Ar3)p基团中的至少两个基团是相同的。
3.制备根据权利要求1或2所述的化合物的方法,其特征在于通过一种或多种偶联反应和/或环化形成所述式(3)至(7)中之一的化合物。
4.一种混合物,其包含至少一种根据权利要求1或2所述的化合物和至少一种荧光或磷光掺杂剂。
5.一种制剂,其包含至少一种根据权利要求1或2所述的化合物或根据权利要求4所述的混合物和一种或多种溶剂。
6.根据权利要求1或2所述的化合物或根据权利要求4所述的混合物在电子器件中的用途。
7.一种电子器件,其包含至少一种根据权利要求1或2所述的化合物或根据权利要求4所述的混合物,所述电子器件选自有机电致发光器件、有机集成电路、有机场效应晶体管、有机薄膜晶体管、有机发光晶体管、有机太阳能电池、有机染料敏化太阳能电池、有机光学检测器、有机光感受器、有机场猝熄器件、发光电化学电池、有机激光二极管和有机等离子体发射器件。
8.根据权利要求7所述的电子器件,其特征在于所述电子器件是有机电致发光器件,并且根据权利要求1或2所述的化合物在发光层中和/或在空穴传输层中和/或在电子阻挡层中被用作荧光或磷光化合物的基质材料。
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CN106414404A (zh) | 2017-02-15 |
US10418564B2 (en) | 2019-09-17 |
KR101765027B1 (ko) | 2017-08-03 |
KR20170091181A (ko) | 2017-08-08 |
WO2015154843A1 (de) | 2015-10-15 |
JP2017519809A (ja) | 2017-07-20 |
US20170033296A1 (en) | 2017-02-02 |
KR20160119240A (ko) | 2016-10-12 |
EP3130015A1 (de) | 2017-02-15 |
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