TW201918479A - 基於4,6-二苯碸二苯並呋喃的雙極性主體材料及應用 - Google Patents
基於4,6-二苯碸二苯並呋喃的雙極性主體材料及應用 Download PDFInfo
- Publication number
- TW201918479A TW201918479A TW107132334A TW107132334A TW201918479A TW 201918479 A TW201918479 A TW 201918479A TW 107132334 A TW107132334 A TW 107132334A TW 107132334 A TW107132334 A TW 107132334A TW 201918479 A TW201918479 A TW 201918479A
- Authority
- TW
- Taiwan
- Prior art keywords
- host material
- diphenylamine
- alkyl
- bipolar host
- group
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 50
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 title claims abstract description 23
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 31
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 aromatic diphenylamine derivative Chemical class 0.000 claims abstract description 19
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229960005544 indolocarbazole Drugs 0.000 claims abstract description 14
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims abstract description 13
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- 238000006243 chemical reaction Methods 0.000 claims description 17
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 6
- JLEFKRHUPHIQKH-UHFFFAOYSA-N 4,6-diiododibenzofuran Chemical compound O1C2=C(I)C=CC=C2C2=C1C(I)=CC=C2 JLEFKRHUPHIQKH-UHFFFAOYSA-N 0.000 claims description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
- 229950000688 phenothiazine Drugs 0.000 claims description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- 150000003568 thioethers Chemical class 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- PRMPLLMZENWSGN-UHFFFAOYSA-N C1=CC=CC=2OC3=C(C21)C=CC=C3.C3(=CC=CC=C3)C3=CC=CC=2CC1=CC=C(C=C1C32)C3=CC=CC=C3 Chemical compound C1=CC=CC=2OC3=C(C21)C=CC=C3.C3(=CC=CC=C3)C3=CC=CC=2CC1=CC=C(C=C1C32)C3=CC=CC=C3 PRMPLLMZENWSGN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001251 acridines Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000007125 Buchwald synthesis reaction Methods 0.000 claims description 2
- 238000006887 Ullmann reaction Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 230000009477 glass transition Effects 0.000 abstract description 9
- 238000002474 experimental method Methods 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000010410 layer Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QWKRQSRWQSVZBT-UHFFFAOYSA-N C1=CC=C2C(C(=CC2=C1)C3=CC=C(C=C3)F)C4=CC=CC5=C4OC6=C5C=CC=C6C7C8=CC=CC=C8C=C7C9=CC=C(C=C9)F Chemical compound C1=CC=C2C(C(=CC2=C1)C3=CC=C(C=C3)F)C4=CC=CC5=C4OC6=C5C=CC=C6C7C8=CC=CC=C8C=C7C9=CC=C(C=C9)F QWKRQSRWQSVZBT-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- FUFLQGLZQDKOPV-UHFFFAOYSA-N 4,6-bis[(2-bromophenyl)sulfanyl]dibenzofuran Chemical compound BrC1=C(C=CC=C1)SC1=CC=CC2=C1OC1=C2C=CC=C1SC1=C(C=CC=C1)Br FUFLQGLZQDKOPV-UHFFFAOYSA-N 0.000 description 4
- WUZCBRSLHDBNFT-UHFFFAOYSA-N BrC1=CC=CC(C2=CC3=CC=CC=C3C2C2=CC=CC3=C2OC2=C3C=CC=C2C2C3=CC=CC=C3C=C2C2=CC(Br)=CC=C2)=C1 Chemical compound BrC1=CC=CC(C2=CC3=CC=CC=C3C2C2=CC=CC3=C2OC2=C3C=CC=C2C2C3=CC=CC=C3C=C2C2=CC(Br)=CC=C2)=C1 WUZCBRSLHDBNFT-UHFFFAOYSA-N 0.000 description 4
- VMAIDBGYGFEYBD-UHFFFAOYSA-N BrC=1C=C(C=CC1)SC1=CC=CC2=C1OC1=C2C=CC=C1SC1=CC(=CC=C1)Br Chemical compound BrC=1C=C(C=CC1)SC1=CC=CC2=C1OC1=C2C=CC=C1SC1=CC(=CC=C1)Br VMAIDBGYGFEYBD-UHFFFAOYSA-N 0.000 description 4
- RQOQSWYPCRVTPV-UHFFFAOYSA-N FC1=CC=C(C=C1)SC1=CC=CC2=C1OC1=C2C=CC=C1SC1=CC=C(C=C1)F Chemical compound FC1=CC=C(C=C1)SC1=CC=CC2=C1OC1=C2C=CC=C1SC1=CC=C(C=C1)F RQOQSWYPCRVTPV-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 3
- BUZOEUVGVFKTEB-UHFFFAOYSA-N C1=CC=C2C(C(=CC2=C1)C3=CC=CC=C3Br)C4=CC=CC5=C4OC6=C5C=CC=C6C7C8=CC=CC=C8C=C7C9=CC=CC=C9Br Chemical compound C1=CC=C2C(C(=CC2=C1)C3=CC=CC=C3Br)C4=CC=CC5=C4OC6=C5C=CC=C6C7C8=CC=CC=C8C=C7C9=CC=CC=C9Br BUZOEUVGVFKTEB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000001327 Förster resonance energy transfer Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- UWCZIRUJFYRXKE-UHFFFAOYSA-N 1,5-dimethylacridine Chemical compound C1=CC=C2C=C3C(C)=CC=CC3=NC2=C1C UWCZIRUJFYRXKE-UHFFFAOYSA-N 0.000 description 1
- YUQUNWNSQDULTI-UHFFFAOYSA-N 2-bromobenzenethiol Chemical compound SC1=CC=CC=C1Br YUQUNWNSQDULTI-UHFFFAOYSA-N 0.000 description 1
- HNGQQUDFJDROPY-UHFFFAOYSA-N 3-bromobenzenethiol Chemical compound SC1=CC=CC(Br)=C1 HNGQQUDFJDROPY-UHFFFAOYSA-N 0.000 description 1
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JKHPQPFHBLDHDN-UHFFFAOYSA-N C1=CC=C2C(=C1)C(=C(N2)C3=CC=CC4=C3OC5=C4C=CC=C5C6=C(C7=CC=CC=C7N6)C8=CC=CC=C8Br)C9=CC=CC=C9Br Chemical compound C1=CC=C2C(=C1)C(=C(N2)C3=CC=CC4=C3OC5=C4C=CC=C5C6=C(C7=CC=CC=C7N6)C8=CC=CC=C8Br)C9=CC=CC=C9Br JKHPQPFHBLDHDN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Abstract
本發明涉及一種基於4,6-二苯碸二苯並呋喃的雙極性主體材料及其應用,該雙極性主體材料,具有式(I)所述結構的化合物,其中,R1
-R6
表示為烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物,氫,鹵素,C1-C4烷基,R1
-R6
至少一個為取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物。實驗表明,本發明的化合物比常用主體材料CBP具有更高的玻璃化轉變溫度,本發明顯著提高了主體材料的熱穩定性,更符合有機發光二極體對主體材料的要求。
Description
本發明涉及新型的雙極性主體材料,屬於有機發光材料技術領域,具體涉及一種基於4,6-二苯碸二苯並呋喃的雙極性主體材料及其應用。
相比於液晶顯示器需要背光的特性,有機發光二極體(OLED)具有主動發光、回應速度快、耗能低、亮度高、視角廣、可彎曲等特性,在平板顯示領域有著巨大的應用前景,受到了學術界和產業界的高度重視,因此被視為21世紀最具前途的產品之一。目前OLED器件已經實現了規模生產,並廣泛應用在手機、平板電腦、汽車儀錶、可穿戴設備等電子產品上。電致螢光和電致磷光分別被稱為第一代和第二代OLED。基於螢光材料的OLED具有穩定性高的特點,但受限於量子統計學定律,在電啟動作用下,產生的單線態激子和三線態激子的比例為1:3,所以螢光材料電致發光內量子效率最大僅有25%。而磷光材料具有重原子的自旋軌道耦合作用,可以綜合利用單線態激子和三線態激子,理論的內量子效率可達100%。但是,在應用中基於磷光的OLED具有明顯的效率滾降效應,在高亮度應用中有一定的阻礙。
磷光材料可以綜合利用單線態激子和三線態激子,實現100%的內量子效率。研究表明,由於過渡金屬配合物的激發態激子壽命相對過長,在高電流密度下存在三線態激子堆積,會導致三線態-三線態湮滅(TTA)、三線態-極子湮滅(TPA),從而出現效率滾降等現象。為了克服這個問題,研究者們常將磷光材料摻雜於有機主體材料中,諸如摻雜於雙極性主體材料中,可較好的平衡載流子的注入。最近,具有熱活性延遲螢光性質的材料也被應用於磷光器件的主體中,由於熱活性延遲螢光材料具有較小的單線態-三線態能級差,三線態激子可通過反系間竄越到單線態,再通過Förster共振能量轉移(FRET)傳至客體材料中,從而降低三線態激子濃度,其器件性能也獲得提高。因此,對於高效有機發光二極體,開發高性能的主體材料十分重要。
目前,廣泛應用於磷光器件的主體材料為CBP(4,4’-二(9-咔唑基)聯苯),但是它要求的驅動電壓較高、玻璃化轉變溫度(Tg)低(Tg = 62 ℃),易於結晶。另外,CBP是一種P型材料,空穴遷移率遠高於電子遷移率,不利於載流子注入和傳輸平衡,且發光效率低。
針對現有主體(CBP)材料要求的驅動電壓較高、玻璃化轉變溫度易於結晶、載流子注入和傳輸不平衡等問題,本發明提供一種雙極性主體材料,該材料以4,6-二苯碸二苯並呋喃為拉電子中心核,具有給電子能力的二苯胺類、咔唑、吖啶等衍生物作為連接基團, D-A-L-A-D型雙極性材料。
基於4,6-二苯碸二苯並呋喃的雙極性主體材料,具有式(I)所述結構,(I)
其中,R1
-R6
表示為烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物,氫,鹵素,C1-C4烷基,且R1
-R6
至少有一個為烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物。
優選:R1
、R2
、R3
中兩個為氫、鹵素或C1-C4烷基,另一個為C1-C8烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物;R4
、R5
、R6
中兩個為氫、鹵素或C1-C4烷基,另一個為C1-C8烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物。
優選:其中,R2
、R3
、R5
、R6
為氫、鹵素或C1-C4烷基,R1
、R4
為C1-C4烷基取代或者未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物。
優選:其中R2
、R3
、R5
、R6
為氫,R1
、R4
為C1-C4烷基取代或者未取代的吖啶基、咔唑、茚並咔唑。
式(I)所述的化合物為下列結構化合物:。
有機電致發光器件,包括陰極、陽極和有機層,所述有機層為空穴傳輸層、空穴阻擋層、電子傳輸層、發光層中的一層或多層。需要特別指出,上述有機層可以根據需要,這些有機層不必每層都存在。
所述式(I)所述的化合物為發光層的材料。
本發明的電子器件有機層的總厚度為1-1000 nm,優選1-500 nm,更優選5-300 nm。
所述有機層可以通過蒸渡或旋塗形成薄膜。
如上面提到,本發明的式(I)所述的化合物如下,但不限於所列舉的結構: 。
上述雙極主體材料的製備方法,包括以下製備步驟: 首先將二苯並呋喃(a)在正丁基鋰條件下形成鋰鹽,再碘代獲得4,6-二碘二苯並呋喃(b),再與鹵代苯硫酚(氟代、溴代)通過Ullmann反應得到硫醚中間體(c);鹵代硫醚中間體氧化得到鹵代硫碸化合物(d);最後鹵代硫碸化合物(d)與取代或未取代的吖啶、咔唑、二苯胺(e)等通過鈀催化的Buchwald反應或親核取代反應,得到所述的雙極主體材料。
實驗表明,本發明的化合物比常用主體材料CBP具有更高的玻璃化轉變溫度,本發明顯著提高了主體材料的熱穩定性。使用本發明的雙極性主體材料製備的有機電致發光器件,穩定性高,具有更好的應用前景,更符合有機發光二極體對主體材料的要求。
下面結合實施例對本發明作進一步詳細的描述,但本發明的實施方式不限於此。
實施例1
(1) 4,6-二碘二苯並呋喃(b)的合成 合成路線如下所示:具體合成步驟為: 稱取二苯並呋喃(8.41 g, 50 mmol)加至三口燒瓶中,氮氣保護,加入乾燥乙醚(150 mL)中,將燒瓶置於-78℃低溫反應器中,緩慢滴加正丁基鋰(2.2 M, 68 mL, 150 mmol),滴加完畢後,反應體系緩慢升至室溫,繼續攪拌10 h。後降至-78℃,緩慢滴加I2
的四氫呋喃溶液(38 g, 150 mmol),滴加完畢後在室溫攪拌4 h。反應結束後,加入10% NaHSO3
溶液(100 mL),萃取分層,無機相用二氯甲烷萃取(3*50 mL),收集有機相,無水MgSO4
乾燥,旋幹溶液得粗產品,後乙醇打漿,抽濾乾燥,得14g白色固體。產率:67%。
(2) 4,6-雙[(4-氟苯基)硫基]二苯並[b,d]呋喃(c1)的合成 合成路線如下所示:具體合成步驟為: 稱取4,6-二碘二苯並呋喃(b) (5.25 g, 12.5 mmol),4-氟苯硫酚 (3.27 g, 25.5 mmol),CuI (0.48 g, 2.5 mmol),菲囉啉 (0.9 g, 5 mmol),碳酸鉀(4.8 g, 35 mmol)於100 mL三口燒瓶中,換氮氣三次。加入乾燥DMSO,升溫至130℃反應16小時。反應結束後,加入150 mL水,二氯甲烷萃取(3*50 mL),合併有機層,無水硫酸鎂乾燥。砂芯漏斗過濾,旋幹溶劑,乙醇打漿,抽濾乾燥得到4.43 g白色粉末固體。產率:84.6%。
(3) 4,6-雙[(4-氟苯基)碸基]二苯並[b,d]呋喃(d1)的合成 合成路線如下所示:具體合成步驟為: 稱取4,6-雙[(4-氟苯基)硫基]二苯並[b
,d
]呋喃(c1
) (1 g, 2.38 mmol)於燒瓶中,二氯甲烷溶解,反應體系置於冰浴中,緩慢加入2.2當量的間氯過氧苯甲酸,室溫反應24小時。反應結束後,加入5% NaHSO3
溶液50 mL,二氯甲烷萃取(3*50 mL),合併有機層,Na2
CO3
溶液洗滌,無水硫酸鎂乾燥。砂芯漏斗過濾,旋幹溶劑,乙醇打漿,抽濾後乾燥得到1.02 g白色粉末固體。產率:88.7%。
(4) 4,6-雙[(4-(9,9’-二甲基吖啶-10(9H)-基)苯基碸基]二苯並[b,d]呋喃(1)的合成 合成路線如下所示:具體合成步驟為: 稱取9,9’二甲基吖啶 (0.89 g, 4.2 mmol)於50 mL燒瓶中,加入10 mL乾燥DMF,0℃條件下緩慢加入NaH (60%, 0.21 g, 5.2 mmol),室溫攪拌30 min,後一次性加入4,6-雙[(4-氟苯基)碸基]二苯並[b,d]呋喃(d1) (1 g, 2.06 mmol),反應在60℃攪拌6小時。反應結束後,加入20 mL水,有固體析出,抽濾,水洗,二氯甲烷:正己烷= 2:1為洗脫劑,矽膠柱層析分離得1.4 g黃色固體。產率:78.6%。 產物鑒定資料如下:1
H NMR (400MHz ,CDCl3
)δ
= 8.73 (d,J
= 8.0 Hz, 4 H), 8.27 (d,J
= 8.0 Hz, 4 H), 7.65-7.59 (m, 6 H), 7.44-7.42 (m, 4 H), 6.95-6.93 (m, 8 H), 6.34-6.31 (m, 4 H), 1.63 (s, 6 H), 1.57 (s, 6 H) ppm.13
C NMR (100MHz , CDCl3
) = 147.1, 140.1, 131.7, 131.0, 130.5, 128.0, 126.2, 125.0, 124.0, 121.5, 115.2, 30.7 ppm. Ms(ESI: Mz 863) (M+1)
實施例2
(1) 4,6-雙[(4-(9H-咔唑-9-基)苯基碸基]二苯並[b,d]呋喃(2)的合成 合成路線如下所示:具體合成步驟為: 稱取咔唑 (1.7 g, 10 mmol)於50 mL燒瓶中,加入20 mL乾燥DMF,0℃條件下緩慢加入NaH (60%, 0.6 g, 15 mmol),室溫攪拌30 min,後一次性加入4,6-雙[(4-氟苯基)碸基]二苯並[b,d]呋喃(d1) (3 g, 5 mmol),反應在60℃攪拌6小時。反應結束後,加入60 mL水,有固體析出,抽濾,水洗,二氯甲烷:正己烷= 2:1為洗脫劑,矽膠柱層析分離得3.3 g黃色固體。產率:85.7%。 產物鑒定資料如下:1
H NMR (400MHz ,CDCl3
)δ
= 8.62 (d,J
= 8.0 Hz, 4 H), 8.66 (d,J
= 8.0 Hz, 2 H), 8.23 (d,J
= 8.0 Hz, 2 H), 8.15 (d,J
= 8.0 Hz, 4 H), 7.93 (d,J
= 8.0 Hz, 4 H), 7.72 (t,J
= 8.0 Hz, 2 H), 7.44 (d,J
= 8.0 Hz, 4 H), 7.30 (t,J
= 8.0 Hz, 4 H), 7.22 (t,J
= 8.0 Hz, 4 H) ppm.13
C NMR (100MHz , CDCl3
) = 141.9, 138.9, 129.8, 128.1, 127.6, 126.7, 126.2, 124.7, 124.5, 123.0, 120.6, 120.3, 110.3, 109.6 ppm.Ms(ESI: Mz 779) (M+1)
實施例3
(1) 4,6-雙[(3-溴苯基)硫基]二苯並[b,d]呋喃(c2)的合成 合成路線如下所示:具體合成步驟為: 稱取4,6-二碘二苯並呋喃(b
) (1.05 g, 2.5 mmol),3-溴苯硫酚 (0.98 g, 5.2 mmol),CuI (0.095 g, 0.5 mmol),菲囉啉 (0.18 g, 1 mmol),碳酸鉀(0.96 g, 7 mmol)於50 mL三口燒瓶中,換氮氣三次。加入10 mL乾燥DMSO,升溫至130℃反應16小時。反應結束後,加入150 mL水,二氯甲烷萃取(3*20 mL),合併有機層,無水硫酸鎂乾燥。砂芯漏斗過濾,旋幹溶劑,正己烷/乙酸乙酯 = 20/1洗脫劑矽膠柱層析分離得0.9 g白色固體。產率:66%。
(2) 4,6-雙[(3-溴苯基)碸基]二苯並[b,d]呋喃(d2)的合成 合成路線如下所示:具體合成步驟為: 稱取4,6-雙[(3-溴苯基)硫基]二苯並[b
,d
]呋喃(c2
) (0.9 g, 1.66 mmol)於燒瓶中,二氯甲烷溶解,反應體系置於冰浴中,緩慢加入2.2當量的間氯過氧苯甲酸,室溫反應24小時。反應結束後,加入5% NaHSO3
溶液50 mL,二氯甲烷萃取(3*50 mL),合併有機層,Na2
CO3
溶液洗滌,無水硫酸鎂乾燥。砂芯漏斗過濾,旋幹溶劑,乙醇打漿,抽濾乾燥得到0.8 g白色粉末固體。產率:80%。
(3) 4,6-雙[(3-(9H-咔唑-9-基)苯基碸基]二苯並[b,d]呋喃(3)的合成 合成路線如下所示:具體合成步驟為: 稱取4,6-雙[(3-溴苯基)碸基]二苯並[b
,d
]呋喃(d2
) (0.136 g, 0.3 mmol),咔唑 (0.1 g, 0.6 mmol),Pd2
(dba)3
(28 mg, 0.03 mmol),P(t
Bu)3
甲苯溶液 (24 mg, 0.06 mmol), 叔丁醇鈉 (0.115 g, 1.2 mmol), 甲苯5 mL於10 mL Schlenk瓶中,氮氣保護,110℃反應10小時。反應結束後,加入20 mL 5% NaHSO3
溶液,二氯甲烷萃取(3*20 mL),正己烷/乙酸乙酯= 2:1為洗脫劑,矽膠柱層析分離得0.18 g黃色固體。產率:69%。 產物鑒定資料如下: Ms(ESI: Mz 779) (M+1)
實施例4
(1) 4,6-雙[(2-溴苯基)硫基]二苯並[b,d]呋喃(c3)的合成 合成路線如下所示:具體合成步驟為: 稱取4,6-二碘二苯並呋喃(b
) (2.1 g, 5 mmol),2-溴苯硫酚 (1.96 g, 10.4 mmol),CuI (0.19 g, 1 mmol),菲囉啉 (0.36 g, 2 mmol),碳酸鉀(2 g, 14 mmol)於50 mL三口燒瓶中,換氮氣三次。加入20 mL乾燥DMSO,升溫至130℃反應15小時。反應結束後,加入150 mL水,二氯甲烷萃取(3*30 mL),合併有機層並水洗,無水硫酸鎂乾燥。砂芯漏斗過濾,旋幹溶劑,正己烷/乙酸乙酯 = 20/1洗脫劑矽膠柱層析分離得1.5 g白色固體。產率:55%。
(2) 4,6-雙[(2-溴苯基)碸基]二苯並[b,d]呋喃(d3)的合成 合成路線如下所示:具體合成步驟為: 稱取4,6-雙[(2-溴苯基)硫基]二苯並[b
,d
]呋喃(c3
) (1.4 g, 2.58 mmol)於燒瓶中,二氯甲烷溶解,反應體系置於冰浴中,緩慢加入2.2當量的間氯過氧苯甲酸,室溫反應24小時。反應結束後,加入5% NaHSO3
溶液50 mL,二氯甲烷萃取(3*50 mL),合併有機層,Na2
CO3
溶液洗滌,無水硫酸鎂乾燥。砂芯漏斗過濾,旋幹溶劑,乙醇打漿,抽濾乾燥得到1.4 g白色粉末固體。產率:89%。
(3) 4,6-雙[(2-(9H-咔唑-9-基)苯基碸基]二苯並[b,d]呋喃(4)的合成 合成路線如下所示:具體合成步驟為: 稱取4,6-雙[(2-溴苯基)碸基]二苯並[b
,d
]呋喃(d3
) (1.36 g, 3 mmol),咔唑 (1 g, 6 mmol),Pd2
(dba)3
(0.28g, 0. 3 mmol),P(t
Bu)3
甲苯溶液 (0.24 g, 0.6 mmol), 叔丁醇鈉 (1.15 g, 12 mmol), 甲苯10 mL於25 mL Schlenk瓶中,氮氣保護,110℃反應10小時。反應結束後,加入30 mL 5% NaHSO3
溶液,二氯甲烷萃取(3*30 mL),正己烷/乙酸乙酯= 2:1為洗脫劑,矽膠柱層析分離得1.1 g黃色固體。產率:47%。 產物鑒定資料如下: Ms(ESI: Mz 779) (M+1)
實施例5 玻璃化轉變溫度測試: 氮氣保護下,以20o
C/min的加熱和冷卻速率用示差掃描量熱法(DSC)測試化合物2
的玻璃化轉變溫度。測得化合物2
的玻璃化轉變溫度T g
為180o
C (圖1)。而文獻所報導的CBP的玻璃化轉變溫度僅為62o
C。 可見,本發明中的化合物比常用主體材料CBP具有更高的玻璃化轉變溫度,本發明顯著提高了主體材料的熱穩定性。
實施例6
有機電致發光器件的製備 器件結構為ITO/HATCN(5 nm)/TAPC(50 nm)/化合物2:Ir(ppy):(4 wt%, 20 nm)/TmPyPb(50 nm)/ LiF(1 nm)/AL(100 nm)
器件製備方式描述如下:見圖2 首先,將透明導電ITO玻璃基板(包含10和20)按照以下步驟處理:預先用洗滌劑溶液、去離子水,乙醇,丙酮,去離子水洗淨,再經氧等離子處理30秒。 然後,在ITO上蒸渡5 nm 厚的HATCN作為空穴注入層30。 然後,在空穴注入層上蒸渡50 nm厚的TAPC作為空穴傳輸層40。 然後,在空穴傳輸層上蒸渡20 nm厚的化合物2:Ir(ppy):(4wt%)作為發光層50。 然後,在發光層上蒸渡50 nm厚的TmPyPb作為電子傳輸層60。 然後,在電子傳輸層上蒸渡1 nm厚的LiF作為電子注入層70。 最後,在電子注入層上蒸渡100 nm厚的鋁作為器件陰極80。
比較例
電致發光器件的製備 器件結構為ITO/HATCN(5 nm)/TAPC(50 nm)/CBP:Ir(ppy):(4 wt%, 20 nm)/TmPyPb(50 nm)/ LiF(1 nm)/AL(100 nm) 方法同實施例6,但使用常用市售化合物CBP作為主體材料,製作對比用電致發光有機半導體二極體器件。
實驗表明,使用本發明的雙極性主體材料製備的電致發光器件,在20 mA/cm2
電流密度下,電壓為6.99 V,亮度7082 cd/m2
,電流效率35.41 cd/A,功率效率15.91 lm/W,外量子效率EQE為9.98%;而使用市售主體CBP製備的電致發光器件在同等電流密度下,電壓為7.71 V,亮度5845 cd/m2
,電流效率29.23 cd/A,功率效率11.91 lm/W,外量子效率EQE為8.5%。因此使用本發明的雙極性主體材料,可獲得比CBP製備的器件高21%的電流效率以及高17.4%的外量子效率,可獲得更高的器件穩定性,具有更好的應用前景,更符合有機發光二極體對主體材料的要求。
圖1為化合物2的DSC曲線。 圖2為本發明的器件結構圖,其中10代表為玻璃基板,20代表為陽極,30代表為空穴注入層,40代表為空穴傳輸層,50代表發光層,60代表為電子傳輸,70代表為電子注入層,80代表為陰極。
Claims (10)
- 一種基於4,6-二苯碸二苯並呋喃的雙極性主體材料,具有式(I)所述結構,(I) 其中,R1 -R6 表示為烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物,氫,鹵素,C1-C4烷基,且R1 -R6 至少有一個為烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物。
- 如申請專利範圍第1項所述的雙極性主體材料,其中R1 、R2 、R3 中兩個為氫、鹵素或C1-C4烷基,另一個為C1-C8烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物;R4 、R5 、R6 中兩個為氫、鹵素或C1-C4烷基,另一個為C1-C8烷基取代或未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物。
- 如申請專利範圍第2項所述的雙極性主體材料,其中R1 、R4 相同,R2 、R5 相同,R3 、R6 相同。
- 如申請專利範圍第3項所述的雙極性主體材料,其中R2 、R3 、R5 、R6 為氫、鹵素或C1-C4烷基,R1 、R4 為C1-C4烷基取代或者未取代的吖啶基、吩噻嗪基、吩噁嗪基、咔唑、茚並咔唑、二苯胺或其它芳香性二苯胺衍生物。
- 如申請專利範圍第4項所述的雙極性主體材料,其中R2 、R3 、R5 、R6 為氫,R1 、R3 為C1-C4烷基取代或者未取代的吖啶基、咔唑、茚並咔唑。
- 如申請專利範圍第1項所述的雙極主體材料,其中所述式(I)為下列結構之一: 。
- 如申請專利範圍第6項所述的雙極主體材料,其中所述式(I)為下列結構之一:。
- 如申請專利範圍第7項所述的雙極主體材料,其中所述式(I)為下列結構:。
- 一種如申請專利範圍第1至8項中之任一所述的雙極主體材料的製備方法,採用如下方法製得: 首先將二苯並呋喃(a)在正丁基鋰條件下形成鋰鹽,再碘代獲得4,6-二碘二苯並呋喃(b),再與鹵代苯硫酚通過Ullmann反應得到硫醚中間體(c);鹵代硫醚中間體氧化得到鹵代硫碸化合物(d);最後鹵代硫碸化合物(d)與烷基取代或未取代的吖啶、咔唑、二苯胺(e)等通過鈀催化的Buchwald反應或親核取代反應,得到所述的雙極主體材料,所述鹵代為氟代或溴代;其反應式如下:。
- 一種如申請專利範圍第1至8項中之任一所述的雙極主體材料在有機電致發光器件中的應用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711061783.4A CN109748908B (zh) | 2017-11-02 | 2017-11-02 | 基于4,6-二苯砜二苯并呋喃的双极性主体材料及应用 |
??201711061783.4 | 2017-11-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201918479A true TW201918479A (zh) | 2019-05-16 |
TWI668218B TWI668218B (zh) | 2019-08-11 |
Family
ID=66331344
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW107132334A TWI668218B (zh) | 2017-11-02 | 2018-09-13 | 基於4,6-二苯碸二苯並呋喃的雙極性主體材料及應用 |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP6836019B2 (zh) |
KR (1) | KR102350371B1 (zh) |
CN (1) | CN109748908B (zh) |
TW (1) | TWI668218B (zh) |
WO (1) | WO2019085688A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113429391B (zh) * | 2021-07-14 | 2022-07-19 | 山西大学 | 一种含二苯砜骨架的化合物及其制备方法和应用 |
CN113788820B (zh) * | 2021-08-25 | 2023-08-22 | 常州大学 | 基于二苯并杂环共轭π桥的蓝色热活性延迟荧光材料及应用 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05109485A (ja) * | 1991-10-15 | 1993-04-30 | Ricoh Co Ltd | 電界発光素子 |
JP5109485B2 (ja) * | 2007-06-05 | 2012-12-26 | 株式会社タンガロイ | 旋削用スローアウェイチップ |
CN103626683A (zh) * | 2012-08-20 | 2014-03-12 | 海洋王照明科技股份有限公司 | 一种有机半导体材料、制备方法和电致发光器件 |
CN103804276A (zh) * | 2012-11-08 | 2014-05-21 | 海洋王照明科技股份有限公司 | 双极性红光磷光化合物、其制备方法和有机电致发光器件 |
CN103804332A (zh) * | 2012-11-08 | 2014-05-21 | 海洋王照明科技股份有限公司 | 电子传输型红光磷光化合物及其制备方法和应用 |
US20180212158A1 (en) * | 2015-07-13 | 2018-07-26 | President And Fellows Of Harvard College | Organic light-emitting diode materials |
-
2017
- 2017-11-02 CN CN201711061783.4A patent/CN109748908B/zh active Active
-
2018
- 2018-09-13 TW TW107132334A patent/TWI668218B/zh active
- 2018-09-25 KR KR1020207011732A patent/KR102350371B1/ko active IP Right Grant
- 2018-09-25 JP JP2020523421A patent/JP6836019B2/ja active Active
- 2018-09-25 WO PCT/CN2018/107240 patent/WO2019085688A1/zh active Application Filing
Also Published As
Publication number | Publication date |
---|---|
KR102350371B1 (ko) | 2022-01-18 |
WO2019085688A1 (zh) | 2019-05-09 |
TWI668218B (zh) | 2019-08-11 |
CN109748908B (zh) | 2021-07-16 |
JP6836019B2 (ja) | 2021-02-24 |
KR20200056441A (ko) | 2020-05-22 |
CN109748908A (zh) | 2019-05-14 |
JP2021501989A (ja) | 2021-01-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101460365B1 (ko) | 신규한 이미다졸 유도체 및 이를 이용한 유기전자소자 | |
KR101412437B1 (ko) | 신규한 화합물 및 이를 이용한 유기 전자 소자 | |
KR100961821B1 (ko) | 신규한 안트라센 유도체 및 이를 이용한 유기전자소자 | |
JP5497045B2 (ja) | 新規なアントラセン誘導体およびこれを用いた有機電子素子 | |
KR20130093195A (ko) | 오원자 헤테로 고리를 포함하는 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 | |
TWI675030B (zh) | 含有4,6-二苯碸二苯並呋喃的雙極性材料的器件 | |
KR20130100948A (ko) | 신규한 안트라센 유도체 및 이를 이용한 유기전자소자 | |
TWI668218B (zh) | 基於4,6-二苯碸二苯並呋喃的雙極性主體材料及應用 | |
WO2021190380A1 (zh) | 有机化合物、电子元件和电子装置 | |
KR20140021293A (ko) | 신규 화합물 및 이를 이용한 유기전계발광소자 | |
WO2023160121A1 (zh) | 有机化合物及包含其的电子元件和电子装置 | |
KR101380008B1 (ko) | 신규한 안트라센 유도체 및 이를 이용한 유기 전자 소자 | |
TWI679199B (zh) | 含有4-硫碸芳基二苯並呋喃的光電材料及應用 | |
KR20130083887A (ko) | 새로운 이미다졸 유도체 및 이를 이용한 유기전자소자 | |
KR101251656B1 (ko) | 신규한 안트라센 유도체 및 이를 이용한 유기전자소자 | |
WO2024148883A1 (zh) | 有机化合物、组合物、有机电致发光器件及电子装置 | |
KR101273057B1 (ko) | 신규한 안트라센 유도체 및 이를 이용한 유기 전자 소자 | |
KR20140009095A (ko) | 신규한 이미다졸 유도체 및 이를 이용한 유기전자소자 | |
KR20220139521A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
CN114075166A (zh) | 一种有机化合物以及使用其的电子元件和电子装置 | |
CN115246851A (zh) | 一种含硼有机化合物及含有其的有机光电元件与应用 | |
KR20230134997A (ko) | 유기발광소자 | |
CN116396253A (zh) | 含氮化合物和电子元件及电子装置 | |
KR20230000475A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220094826A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 |