CN114539270A - 含有咔唑衍生物的化合物及其在有机电致发光器件中的应用 - Google Patents
含有咔唑衍生物的化合物及其在有机电致发光器件中的应用 Download PDFInfo
- Publication number
- CN114539270A CN114539270A CN202111499999.5A CN202111499999A CN114539270A CN 114539270 A CN114539270 A CN 114539270A CN 202111499999 A CN202111499999 A CN 202111499999A CN 114539270 A CN114539270 A CN 114539270A
- Authority
- CN
- China
- Prior art keywords
- group
- carbazole derivative
- substituted
- carbon atoms
- unsubstituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 230000005525 hole transport Effects 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000732 arylene group Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000707 boryl group Chemical group B* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- -1 aromatic amine compounds Chemical class 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 4
- 239000011368 organic material 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
- 238000010898 silica gel chromatography Methods 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- 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
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
技术领域
本发明属于有机电致发光材料领域,具体涉及含有咔唑衍生物的化合物及其在有机电致发光器件中的应用。
背景技术
目前,有机电致发光器件(OLED)的空穴传输材料主要采用芳香胺类化合物,如4,4′-双[N-(1-萘基)-N-苯基氨基]联二苯(NPB)、N,N′-二苯基-N,N′-双(3-甲基苯基)-(1,1′-联苯基)-4,4′-二胺(TPD)等,这类材料具有高的空穴迁移率,但由于其玻璃化转变温度较低,薄膜经长时间放置后常出现再结晶现象,这被认为是导致电致发光(EL)器件衰减的原因之一。因此,为获取高转换效率和长寿命的EL器件,提高空穴传输材料的玻璃化转变温度是有效手段。
在作为空穴传输材料的芳香胺类化合物分子中引入大的稠环共轭单元,能够形成分子内位阻,提高玻璃化转变温度,此外稠环单元延长共轭也利于空穴迁移率的提高。基于以上,本发明从分子结构设计出发,首次尝试并提出一种新的咔唑衍生物类二胺化合物,具体如下所述。
发明内容
本发明提供了含有咔唑衍生物的化合物,其通式结构由如下式1所示的结构与式2所示的化学结构通过化学键连接而成:
在式1中,Ar1、Ar2、Ar3、Ar4各自独立地选自取代或未取代的碳原子数为6~18的芳基或杂芳基;L1、L2、L3、L4各自独立地选自不存在、取代或未取代的碳原子数为6~18的亚芳基或亚杂芳基,R1选自碳原子数为1~10的烷基、取代或未取代的碳原子数为6~18的芳基或杂芳基;
在式2中,X选自O、S、Se、-C(CH3)2-或-Si(CH3)2-;R2和R3独立选自氢、氘、碳原子数为1~10的烷基、取代或未取代的碳原子数为6~12的芳基或杂芳基、或者R2和R3连接形成苯环,且R2和R3不同时为氢或氘;
其中,在式1和2中,所述杂芳基或亚杂芳基中杂原子选自O、S、Si或Se,*a、*b、*c、*y和*z均表示连接位点,且式1中*a、*b、*c任意相邻两个位点与式2中*y和*z通过化学键连接成环。
与现有技术相比,本发明的有益效果在于:本发明中含有咔唑衍生物的化合物通过在三芳胺的适当位置引入共轭稠环片段,此外稠环单元延长共轭也利提高于空穴迁移率,赋予化学结构高迁移率的同时能级符合空穴传输材料的使用要求;另外共轭稠环还可形成分子内位阻,有利于减少分子间的平面作用,提高玻璃转化温度,作为空穴传输材料可以延长器件使用寿命。
附图说明
图1是实施例中底部发光有机电致发光器件的结构示意图。
图2是实施例中顶部发光有机电致发光器件的结构示意图。
具体实施方式
为使本发明实施例的目的、技术方案和优点更加清楚,下面将结合本发明实施例的附图,对本发明实施例的技术方案进行清楚、完整地描述。显然,所描述的实施例是本发明的一部分实施例,而不是全部的实施例。基于所描述的本发明的实施例,本领域普通技术人员在无需创造性劳动的前提下所获得的所有其它实施例,都属于本发明保护的范围。
本发明提供的含有咔唑衍生物的化合物,其通式结构由如下式1所示的结构与式2所示的化学结构通过化学键连接而成:
在式1中,Ar1、Ar2、Ar3、Ar4各自独立地选自取代或未取代的碳原子数为6~18的芳基或杂芳基;L1、L2、L3、L4各自独立地选自不存在、取代或未取代的碳原子数为6~18的亚芳基或亚杂芳基,R1选自碳原子数为1~10的烷基、取代或未取代的碳原子数为6~18的芳基或杂芳基;
在式2中,X选自O、S、Se、-C(CH3)2-或-Si(CH3)2-;R2和R3独立选自氢、氘、碳原子数为1~10的烷基、取代或未取代的碳原子数为6~12的芳基或杂芳基、或者R2和R3连接形成苯环,且R2和R3不同时为氢或氘;
其中,在式1和2中,所述杂芳基或亚杂芳基中杂原子选自O、S、Si或Se,*a、*b、*c、*y和*z均表示连接位点,且式1中*a、*b、*c任意相邻两个位点与式2中*y和*z通过化学键连接成环。
上述含有咔唑衍生物的化合物中取代基的描述如下,当不限于此。
“取代或未取代的”指选自以下一个或多个取代基取代:氢、氘、卤素基、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基和杂环基,或未取代;或者连接以上取代基中的两个或多个取代基的取代基取代,或未取代,如“连接两个或多个取代基的取代基”包括联苯基,即联苯基可为芳基或者为连接两个苯基的取代基。
“芳基”可为单环芳基或多环芳基,单环芳基包括苯基、联苯基、三联苯基、四联苯基,多环芳基包括萘基、蒽基、菲基、芘基、芴基,以上对芳基的描述可用于亚芳基,不同之处在于亚芳基为二价。
根据一些实施方式,上述含有咔唑衍生物的化合物具有如化学式a–d所示的通式结构:
根据一些实施方式,上述化学式a–d中,R1选自甲基、乙基、正丙基、异丙基、叔丁基、或者甲基取代、甲氧基取代、甲硫基取代或未取代的苯基、甲基取代或未取代的噻吩基、甲基取代或未取代的环戊烷基、甲基取代或未取代的环己烷基、甲基取代或未取代的萘基。
根据一些实施方式,上述含有咔唑衍生物的化合物具有如化学式e–h所示的通式结构:
上述化学式e–h中,R2和R3有一个为氢。
根据一些实施方式,上述化学式e–h中,R2选自甲基、乙基、正丙基、异丙基、叔丁基、或者甲基取代、甲氧基取代、甲硫基取代或未取代的苯基、甲基取代或未取代的噻吩基、甲基取代或未取代的环戊烷基、甲基取代或未取代的环己烷基、甲基取代或未取代的萘基,R3为氢。
根据一些实施方式,本发明中含有咔唑衍生物的化合物选自以下任一个化学结构:
根据一些实施方式,本发明中含有咔唑衍生物的化合物选自以下任一个化学结构:
本发明中上述含有咔唑衍生物的化合物通用合成路线如下所示,根据终产物的分子结构选择合适的起始原料,且下述路线以及表1中所涉及原料均为市售化学品。
化合物0-3的合成:在氮气氛围下,将化合物0-1(15mmol)、2-氯-4-溴苯硼酸频哪醇酯(化合物0-2,5.7g,18mmol)、碳酸钾(10.4g,75mmol)、四(三苯基膦)钯(0.7g,0.6mmol),以及脱气甲苯、四氢呋喃和去离子水的混合溶剂(80ml/80ml/80ml)依次加入三口烧瓶中,开启剧烈搅拌,在80℃下加热8小时。随后停止搅拌,将反应液倒入300ml蒸馏水中,静置分层,收集有机相,加入无水硫酸钠干燥,过滤后减压蒸馏去除溶剂,所得粗产物通过硅胶柱色谱和重结晶方法纯化。
化合物0-4的合成:氮气氛围下,向三口烧瓶中依次加入化合物0-3(10mmol),三苯基膦(6.6g,25mmol)和无水邻二氯苯(60ml),充分搅拌后升温至180℃反应12小时。待反应混合物冷却至室温后,将其倒入二氯甲烷中并用水洗涤,有机相用无水硫酸钠干燥,过滤并真空蒸发去除溶剂,所得粗产物通过硅胶柱色谱和重结晶方法纯化。
化合物0-5的合成:氮气氛围下,向三口烧瓶中依次加入化合物0-4(8mmol)、碘化亚铜(1.2g,6.5mmol)、碳酸铯(8.0g,24mmol)和无水甲苯(40ml),开启搅拌并加热,待升温至80℃,依次加入碘化物R1-I(16mmol)和二乙胺(0.8ml,12.2mmol)。加料完毕后,将混合物在氮气氛围下回流搅拌13小时。冷却后将反应液倒入二氯甲烷中并用水洗涤,有机相用无水硫酸钠干燥,过滤并真空蒸发去除溶剂,所得粗产物通过硅胶柱色谱和重结晶方法纯化。
化合物0-7的合成:在氮气氛围下,依次向三口烧瓶中加入化合物0-6(20mmol)、胺类化合物0-7(25mmol)、碘化亚铜(1.9g,10mmol)、碳酸钾(13.8g,0.1mol)和溶剂1,3-二甲基-3,4,5,6-四氢-2-嘧啶酮250ml。开启搅拌,升温至175℃,用薄层色谱法监控反应过程,10小时后停止反应,冷却至室温,将反应液倒入去离子水中,过滤收集滤饼,所得粗产物通过硅胶柱色谱和重结晶方法纯化。
终产物的合成:在氮气氛围下,向三口烧瓶中依次加入120ml无水甲苯、化合物0-7(8mmol)和胺类化合物0-8(8.8mmol)。开启搅拌,再分别加入叔丁醇钠(1.2g,12mmol),双二亚苄基丙酮钯(37mg,0.06mmol)和三叔丁基膦(10%正己烷溶液,0.27ml,0.12mmol),并升温至回流。通过薄层色谱法监控反应,待观察到基本无原料剩余,停止加热,降温至45℃以下时,向反应体系加入5ml浓盐酸(37%H2O)和100ml去离子水的混合溶液,用分液漏斗分液,保留有机相,水相用甲苯(3×50ml)萃取,与前述保留有机相合并,蒸馏去除溶剂,所得粗产物通过硅胶柱色谱和重结晶方法纯化。
以下合成实施例1至40分别详细描述了上述化合物A1、A3、A5、A7、A9、A16、A19、A33、A38、A40、A61、A62、A68、A69、A70、A71、A75、A77、A78、A79、B6、B10、B11、B12、B14、B16、B17、B27、B29、B30、B32、B37、B39、B43、B45、B46、B47、B54、B58和B60的制备方法采用的原料或中间体,未注明制备方法的原料均为市售商品。
表1
本发明还提供上述含有咔唑衍生物的化合物在有机电致发光器件中的应用,具体是作为有机电致发光器件的空穴传输材层材料,可以在顶发光器件、底发光器件或者串联器件中使用。以下器件实施例制备的有机电致发光器件,包括第一电极、第二电极、以及设置在第一电极和第二电极之间的一个或多个有机材料层,为底部或顶部发光器件结构(如图1或2所示),其有机材料层可为单层结构,也可为层合有两个或多个有机材料层的多层串联结构,如具有包括空穴注入层、空穴传输层、发光层、空穴传输层、电子注入层等作为有机材料层的结构,可使用制备有机电致发光器件的常见方法和材料来制备。以下器件实施例1至40分别采用上述化合物A1、A3、A5、A7、A9、A16、A19、A33、A38、A40、A61、A62、A68、A69、A70、A71、A75、A77、A78、A79、B6、B10、B11、B12、B14、B16、B17、B27、B29、B30、B32、B37、B39、B43、B45、B46、B47、B54、B58和B60作为红光有机电致发光器件中与发光层直接接触的空穴传输材层材料。
器件实施例1
按照如图1所示的结构制作红色底部发光有机电致发光器件,制备工艺为:在玻璃材质的基底101上,形成透明阳极ITO膜层,膜厚150nm,得到第一电极102作为阳极,之后蒸镀与化合物的混合材料作为空穴注入层103,混合比例为3:97(质量比),之后蒸镀100nm厚度的化合物得到第一层空穴传输层104,然后蒸镀100nm厚度的本发明的化合物A1,得到第二层空穴传输层105,再以95:5的蒸镀速率蒸镀与40nm,制作红光发光单元106,然后蒸镀10nm形成空穴阻挡层107,然后与混合比例为4:6(质量比)形成厚度30nm的电子传输层108,之后形成厚度100nm的镁银(质量比1:9),作为第二电极109。
器件实施例2至40中分别采用上述化合物A3、A5、A7、A9、A16、A19、A33、A38、A40、A61、A62、A68、A69、A70、A71、A75、A77、A78、A79、B6、B10、B11、B12、B14、B16、B17、B27、B29、B30、B32、B37、B39、B43、B45、B46、B47、B54、B58和B60以及对比例1中采用化合物(D1)替代器件实施例1中化合物A1作为空穴传输层105来制作红光有机电致发光器件。所得有机电致发光器件通过计算机控制的Keithley 2400测试系统计算得到工作电压和效率,使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量系统得到黑暗条件下的器件寿命,每一组实施例器件均与对比例器件在同一批次中产出并测试,将对比例1中器件的工作电压、效率和寿命均分别记为1,计算器件实施例与对比例1中器件相应指标的比值,如表2所示。
表2
从表2可以看出,本发明中含有咔唑衍生物的化合物作为红色底部发光有机电致发光器件的空穴传输层材料,得到的器件驱动电压低、发光效率高且使用寿命长。
此外,本发明中含有咔唑衍生物的化合物还可以作为如图2所示的底部发光器件的空穴传输层105,或者作为串联有机电致发光器件中与红光、绿光发光层直接接触的空穴传输材层材料,得到的器件效果同样显著。
另外,本发明还提供包含上述任一有机电致发光器件的显示装置。
Claims (10)
1.含有咔唑衍生物的化合物,其通式结构由如下式1所示的结构与式2所示的化学结构通过化学键连接而成:
在式1中,Ar1、Ar2、Ar3、Ar4各自独立地选自取代或未取代的碳原子数为6~18的芳基或杂芳基;L1、L2、L3、L4各自独立地选自不存在、取代或未取代的碳原子数为6~18的亚芳基或亚杂芳基,R1选自碳原子数为1~10的烷基、取代或未取代的碳原子数为6~18的芳基或杂芳基;
在式2中,X选自O、S、Se、-C(CH3)2-或-Si(CH3)2-;R2和R3独立选自氢、氘、碳原子数为1~10的烷基、取代或未取代的碳原子数为6~12的芳基或杂芳基、或者R2和R3连接形成苯环,且R2和R3不同时为氢或氘;
其中,在式1和2中,所述杂芳基或亚杂芳基中杂原子选自O、S、Si或Se,*a、*b、*c、*y和*z均表示连接位点,且式1中*a、*b、*c任意相邻两个位点与式2中*y和*z通过化学键连接成环。
2.根据权利要求1所述的含有咔唑衍生物的化合物,其特征在于,所述取代选自如下一个或多个取代基取代:氢、氘、卤素基、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基或杂环基,或者连接以上取代基中的两个或多个取代基的取代基取代。
7.一种有机电致发光器件,包含上述权利要求1至6任一项所述含有咔唑衍生物的化合物。
8.根据权利要求7所述的有机电致发光器件,其特征在于,所述含有咔唑衍生物的化合物作为有机电致发光器件的空穴传输材料。
9.根据权利要求7所述的有机电致发光器件,其特征在于,所述含有咔唑衍生物的化合物作为有机电致发光器件中与发光层直接接触的空穴传输材料。
10.一种显示装置,其特征在于,包含权利要求7至9任一项所述的有机电致发光器件。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111499999.5A CN114539270B (zh) | 2021-12-09 | 2021-12-09 | 含有咔唑衍生物的化合物及其在有机电致发光器件中的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111499999.5A CN114539270B (zh) | 2021-12-09 | 2021-12-09 | 含有咔唑衍生物的化合物及其在有机电致发光器件中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN114539270A true CN114539270A (zh) | 2022-05-27 |
CN114539270B CN114539270B (zh) | 2024-03-29 |
Family
ID=81669816
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111499999.5A Active CN114539270B (zh) | 2021-12-09 | 2021-12-09 | 含有咔唑衍生物的化合物及其在有机电致发光器件中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114539270B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115572303A (zh) * | 2022-09-21 | 2023-01-06 | 上海和辉光电股份有限公司 | 一种有机发光化合物及其应用 |
Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011025282A2 (ko) * | 2009-08-26 | 2011-03-03 | 주식회사 두산 | 신규한 유기 화합물 및 이를 이용한 유기 발광 소자 |
CN102558121A (zh) * | 2010-11-04 | 2012-07-11 | 第一毛织株式会社 | 有机光电子装置用化合物、有机发光二极管和显示器 |
US20120292603A1 (en) * | 2011-05-09 | 2012-11-22 | Yoon-Hyun Kwak | Heterocyclic compound, organic light-emitting device including the heterocyclic compound, and flat display device including the organic light-emitting device |
CN102933582A (zh) * | 2010-04-06 | 2013-02-13 | 巴斯夫欧洲公司 | 取代的咔唑衍生物及其在有机电子器件中的用途 |
CN103086953A (zh) * | 2011-11-03 | 2013-05-08 | 三星显示有限公司 | 杂环化合物和包括该杂环化合物的有机发光装置 |
WO2013108997A1 (ko) * | 2012-01-18 | 2013-07-25 | 덕산하이메탈(주) | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
CN104271700A (zh) * | 2012-04-03 | 2015-01-07 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和包含该化合物的有机电致发光器件 |
CN104271582A (zh) * | 2012-05-02 | 2015-01-07 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和包含该化合物的有机电致发光器件 |
CN104334682A (zh) * | 2012-05-30 | 2015-02-04 | 罗门哈斯电子材料韩国有限公司 | 新颖的有机电致发光化合物和包含该化合物的有机电致发光器件 |
CN105263937A (zh) * | 2013-06-03 | 2016-01-20 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含所述化合物的有机电致发光装置 |
CN106661041A (zh) * | 2014-07-17 | 2017-05-10 | 罗门哈斯电子材料韩国有限公司 | 电子传输材料和包含所述电子传输材料的有机电致发光器件 |
WO2017078403A1 (en) * | 2015-11-03 | 2017-05-11 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of host materials and organic electroluminescent device comprising the same |
KR20170055704A (ko) * | 2015-11-12 | 2017-05-22 | 에스에프씨 주식회사 | 안트라센 유도체 및 이를 포함하는 유기전계발광소자 |
CN107428769A (zh) * | 2015-08-27 | 2017-12-01 | 株式会社Lg化学 | 杂环化合物及包含其的有机发光元件 |
CN107619412A (zh) * | 2016-07-15 | 2018-01-23 | 株式会社Lg化学 | 新的杂环化合物及利用它的有机发光元件 |
CN107771206A (zh) * | 2015-06-26 | 2018-03-06 | 罗门哈斯电子材料韩国有限公司 | 多组分主体材料和包括此材料的有机电致发光装置 |
CN111148817A (zh) * | 2017-09-25 | 2020-05-12 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物以及包含其的有机电致发光装置 |
-
2021
- 2021-12-09 CN CN202111499999.5A patent/CN114539270B/zh active Active
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011025282A2 (ko) * | 2009-08-26 | 2011-03-03 | 주식회사 두산 | 신규한 유기 화합물 및 이를 이용한 유기 발광 소자 |
CN102933582A (zh) * | 2010-04-06 | 2013-02-13 | 巴斯夫欧洲公司 | 取代的咔唑衍生物及其在有机电子器件中的用途 |
CN102558121A (zh) * | 2010-11-04 | 2012-07-11 | 第一毛织株式会社 | 有机光电子装置用化合物、有机发光二极管和显示器 |
US20120292603A1 (en) * | 2011-05-09 | 2012-11-22 | Yoon-Hyun Kwak | Heterocyclic compound, organic light-emitting device including the heterocyclic compound, and flat display device including the organic light-emitting device |
CN103086953A (zh) * | 2011-11-03 | 2013-05-08 | 三星显示有限公司 | 杂环化合物和包括该杂环化合物的有机发光装置 |
WO2013108997A1 (ko) * | 2012-01-18 | 2013-07-25 | 덕산하이메탈(주) | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
CN104271700A (zh) * | 2012-04-03 | 2015-01-07 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和包含该化合物的有机电致发光器件 |
CN104271582A (zh) * | 2012-05-02 | 2015-01-07 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和包含该化合物的有机电致发光器件 |
CN104334682A (zh) * | 2012-05-30 | 2015-02-04 | 罗门哈斯电子材料韩国有限公司 | 新颖的有机电致发光化合物和包含该化合物的有机电致发光器件 |
CN105263937A (zh) * | 2013-06-03 | 2016-01-20 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含所述化合物的有机电致发光装置 |
CN106661041A (zh) * | 2014-07-17 | 2017-05-10 | 罗门哈斯电子材料韩国有限公司 | 电子传输材料和包含所述电子传输材料的有机电致发光器件 |
CN107771206A (zh) * | 2015-06-26 | 2018-03-06 | 罗门哈斯电子材料韩国有限公司 | 多组分主体材料和包括此材料的有机电致发光装置 |
CN107428769A (zh) * | 2015-08-27 | 2017-12-01 | 株式会社Lg化学 | 杂环化合物及包含其的有机发光元件 |
WO2017078403A1 (en) * | 2015-11-03 | 2017-05-11 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of host materials and organic electroluminescent device comprising the same |
KR20170055704A (ko) * | 2015-11-12 | 2017-05-22 | 에스에프씨 주식회사 | 안트라센 유도체 및 이를 포함하는 유기전계발광소자 |
CN107619412A (zh) * | 2016-07-15 | 2018-01-23 | 株式会社Lg化学 | 新的杂环化合物及利用它的有机发光元件 |
CN111148817A (zh) * | 2017-09-25 | 2020-05-12 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物以及包含其的有机电致发光装置 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115572303A (zh) * | 2022-09-21 | 2023-01-06 | 上海和辉光电股份有限公司 | 一种有机发光化合物及其应用 |
CN115572303B (zh) * | 2022-09-21 | 2024-05-17 | 上海和辉光电股份有限公司 | 一种有机发光化合物及其应用 |
Also Published As
Publication number | Publication date |
---|---|
CN114539270B (zh) | 2024-03-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101447959B1 (ko) | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 | |
KR101527181B1 (ko) | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 | |
KR101772990B1 (ko) | 열안정성이 향상된 유기소자용 화합물 및 이의 제조방법 및 이를 포함하는 유기발광소자 | |
CN117417261A (zh) | 2,3-取代的萘胺衍生物有机发光化合物以及有机电致发光器件 | |
KR101584753B1 (ko) | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 | |
TW201833089A (zh) | 咪唑雜菲化合物以及包含其的有機發光二極體 | |
KR101597865B1 (ko) | 신규한 화합물 및 이를 이용한 유기 전자 소자 | |
CN109293516B (zh) | 一种三芳胺类化合物及其有机发光器件 | |
CN111170874A (zh) | 一种芳胺类化合物及其有机电致发光器件 | |
KR20180136377A (ko) | 신규한 화합물 및 이를 포함하는 유기발광 소자 | |
CN113402507B (zh) | 三亚苯衍生物,发光器件材料及发光器件 | |
CN108530443A (zh) | 一种邻菲啰啉衍生物及其有机电致发光器件 | |
CN112961175B (zh) | 多环芳族有机物、其合成工艺、发光材料和有机电致发光器件 | |
CN114539270B (zh) | 含有咔唑衍生物的化合物及其在有机电致发光器件中的应用 | |
KR101576921B1 (ko) | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 | |
EP3444257B1 (en) | Organic electroluminescent material and organic electroluminescent device | |
KR101274926B1 (ko) | 유기 화합물 및 이를 이용한 유기 전계 발광 소자 | |
CN114790145A (zh) | 含茚并芴基团的芳胺化合物和有机电致发光器件 | |
KR20140015226A (ko) | 신규한 화합물 및 이를 이용한 유기 전자 소자 | |
KR20130070151A (ko) | 아자인데노안트라센 유도체 및 이를 이용한 유기 전계 발광 소자 | |
CN114685482A (zh) | 一种有机电致发光化合物及其应用 | |
CN114426539B (zh) | 有机化合物及包含其的有机电致发光器件和电子装置 | |
CN114671800B (zh) | 一种咔唑类衍生物及其制备方法与应用 | |
CN110655438A (zh) | 一种以环庚烯为核心的化合物及其在有机电致发光器件上的应用 | |
CN114685286B (zh) | 三芳胺化合物、包含该化合物的有机电致发光器件 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB03 | Change of inventor or designer information | ||
CB03 | Change of inventor or designer information |
Inventor after: Wang Xiangcheng Inventor before: He Mu Inventor before: Wang Xiangcheng |
|
GR01 | Patent grant | ||
GR01 | Patent grant |