CN113980026B - 咔唑衍生物类胺化合物和包含其的有机电致发光器件 - Google Patents
咔唑衍生物类胺化合物和包含其的有机电致发光器件 Download PDFInfo
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- CN113980026B CN113980026B CN202111413037.3A CN202111413037A CN113980026B CN 113980026 B CN113980026 B CN 113980026B CN 202111413037 A CN202111413037 A CN 202111413037A CN 113980026 B CN113980026 B CN 113980026B
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- carbon atoms
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- -1 Carbazole derivative amine compound Chemical class 0.000 title claims abstract description 37
- 239000000463 material Substances 0.000 claims abstract description 19
- 230000005525 hole transport Effects 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 31
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 125000003118 aryl group Chemical group 0.000 abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 8
- 229910052805 deuterium Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 125000000732 arylene group Chemical group 0.000 abstract description 5
- 125000005549 heteroarylene group Chemical group 0.000 abstract description 5
- 150000002431 hydrogen Chemical class 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 28
- 125000001424 substituent group Chemical group 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 125000005259 triarylamine group Chemical group 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
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 1
- 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
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- FZXBQUOJWSANJI-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=C(C=CC(=C3N2)Br)Cl Chemical compound C1=CC=C2C(=C1)C3=C(C=CC(=C3N2)Br)Cl FZXBQUOJWSANJI-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- IARLISDOOLYUNK-UHFFFAOYSA-N O[PH2]=N Chemical compound O[PH2]=N IARLISDOOLYUNK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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 System
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—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
Abstract
本发明公开了咔唑衍生物类胺化合物和包含其的有机电致发光器件，该化合物的化学结构为Ar1和Ar2独立选自氢、氘、碳原子数为1–10的烷基或烷氧基、取代或未取代的碳原子数为6–30的芳基、取代或未取代的碳原子数为5–30的杂芳基；L1和L2独立选自不存在、取代或未取代的碳原子数为6–18的亚芳基、取代或未取代的碳原子数为5–18的亚杂芳基；R1和R2独立选自碳原子数为1–10的烷基或烷氧基、取代或未取代的碳原子数为6–30的芳基、取代或未取代的碳原子数为5–30的杂芳基，R3和R4分别独立为氢或氘。本发明的咔唑衍生物类胺化合物作为空穴传输材料可以延长器件使用寿命。
Description
技术领域
本发明属于有机电致发光材料领域，具体涉及咔唑衍生物类胺化合物和包含其的有机电致发光器件。
背景技术
目前，有机电致发光器件(OLED)的空穴传输层材料主要为芳香胺类化合物，其具有能级易调节的优势，可以根据器件对能级的不同要求进行相应设计。共轭稠环类化合物结构具有高迁移率的特性，通过在三芳胺的适当位置引入共轭稠环片段，可令此类化合物具有高迁移率的同时能级符合空穴传输材料的使用要求。此外，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，从而提升器件寿命。例如，专利文献KR101825543B1报道一系列含稠并芴单元的单胺类分子，将器件发光效率提升；专利文献KR101265658B1报道一类基于吲哚并咔唑和含氮杂环的化合物，这类材料作为发光层主体材料能够提升器件的发光效率和寿命，但由于其能级与阳极材料功函不匹配，难用于空穴传输层中。基于此，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胺化合物，具体如下所述。
发明内容
本发明提供了一种咔唑衍生物类胺化合物，具有如化学式1所示的化学结构：
在化学式1中，Ar1和Ar2分别独立选自氢、氘、碳原子数为1–10的烷基或烷氧基、取代或未取代的碳原子数为6–30的芳基、取代或未取代的碳原子数为5–30的杂芳基；
L1和L2分别独立选自不存在、取代或未取代的碳原子数为6–18的亚芳基、取代或未取代的碳原子数为5–18的亚杂芳基；
R1和R2分别独立选自碳原子数为1–10的烷基或烷氧基、取代或未取代的碳原子数为6–30的芳基、取代或未取代的碳原子数为5–30的杂芳基；
R3和R4分别独立为氢或氘。
与现有技术相比，本发明的有益效果在于：本发明的咔唑衍生物类胺化合物通过在三芳胺的适当位置引入共轭稠环片段，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。
本发明提供的咔唑衍生物类胺化合物，具有如化学式1所示的化学结构：
在化学式1中，Ar1和Ar2分别独立选自氢、氘、碳原子数为1–10的烷基或烷氧基、取代或未取代的碳原子数为6–30的芳基、取代或未取代的碳原子数为5–30的杂芳基；
L1和L2分别独立选自不存在、取代或未取代的碳原子数为6–18的亚芳基、取代或未取代的碳原子数为5–18的亚杂芳基；
R1和R2分别独立选自碳原子数为1–10的烷基或烷氧基、取代或未取代的碳原子数为6–30的芳基、取代或未取代的碳原子数为5–30的杂芳基；
R3和R4分别独立为氢或氘。
化学式1所示的咔唑衍生物类胺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、五联苯基，多环芳基包括萘基、蒽基、菲基、芘基、苝基、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。
“杂芳基”包含N、O、P、S、Si和Se中的一个或多个作为杂原子，碳原子数为5至30，选自吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、硒吩基、咪唑基、吡唑基、噁唑基、异唑基、噻唑基、异噻唑基、三唑基、二唑基、噻二唑基、二噻唑基、四唑基、吡喃基、噻喃基、吡嗪基、嗪基、噻嗪基、二氧杂环己烯基、三嗪基、四嗪基、喹啉基、异喹啉基、喹啉基、喹唑啉基、喹喔啉基、萘啶基、吖啶基、呫吨基、菲啶基、二氮杂萘基、三氮杂茚基、吲哚基、二氢吲哚基、中氮茚基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、苯并噻唑基、苯并唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、茚并咔唑基、吩嗪基、咪唑并吡啶基、吩嗪基、菲啶基、菲咯啉基、吩噻嗪基、咪唑并吡啶基、咪唑并菲啶基、苯并咪唑并喹唑啉基、或苯并咪唑并菲啶基；以上对杂芳基的描述可用于亚杂芳基，不同之处在于亚杂芳基为二价。
根据一些实施方式，化学式1中，Ar1和Ar2分别独立选自氢、氘、碳原子数为1–10的烷基或烷氧基、取代或未取代的碳原子数为6–18的芳基、取代或未取代的碳原子数为5–18的杂芳基；R1和R2分别独立选自碳原子数为1–10的烷基或烷氧基、取代或未取代的碳原子数为6–18的芳基、取代或未取代的碳原子数为5–18的杂芳基。
根据一些实施方式，化学式1所示的咔唑衍生物类胺化合物选自以下任一个化学结构：
本发明化学式1所示的咔唑衍生物类胺化合物通用合成路线如下所示：
其中，起始原料0-1和其余反应物质均为市售品。
化合物0-2的合成：氮气氛围下，向三口烧瓶中依次加入1-溴-4-氯-9H-咔唑(22.4g，80mmol)、碘化亚铜(12.4g，65mmol)、碳酸铯(79.8g，240mmol)和无水甲苯(250mL)，开启搅拌并加热，待升温至80℃，依次加入碘化物R2-I(160mmol)和二乙胺(8.2mL，122mmol)。加料完毕后，将混合物在氮气氛围下回流搅拌15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0-3的合成：氮气氛围下，将化合物0-2(15mmol)、2-硝基苯硼酸(3.0g，18mmol)、碳酸钾(10.4g，75mmol)、四(三苯基膦)钯(0.7g，0.6mmol)，以及脱气四氢呋喃和去离子水的混合溶剂(100mL/50mL)依次加入三口烧瓶中，充分搅拌后在80℃回流12小时，随后趁热将反应液经过硅藻土过滤，收集滤液并在旋转蒸发仪上旋干，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)和无水零二氯苯(60mL)，充分搅拌后升温至180℃反应11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：采用与化合物0-2相同的方式获得化合物0-5，不同之处在于使用碘化物R1-I替代碘化物R2-I。
终产物的合成：在氮气氛围下，向三口烧瓶中依次加入60mL无水甲苯、化合物0-5(10.3g，8mmol)和胺类化合物0-6(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6详细描述了上述化合物A1、A2、A3、A4、A5和A6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
本发明还提供上述咔唑衍生物类胺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中与红光或绿光发光层直接接触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6分别采用上述化合物A1、A2、A3、A4、A5、A6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10nm厚度的本发明化合物A1，得到第二层空穴传输层105，然后以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/>形成电子阻挡层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6中分别采用上述化合物A2、A3、A4、A5、A6以及对比例1和2中分别采用化合物(D1)和/>(D2)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，得到的有机电致发光器件进行发光效率性能测试，如表2所示。
表2
从表2可以看出，本发明中咔唑衍生物类胺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，本发明中咔唑衍生物类胺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 (4)
1.咔唑衍生物类胺化合物，其特征在于，选自以下任一个化学结构：
2.权利要求1所述咔唑衍生物类胺化合物在有机电致发光器件中的应用。
3.一种有机电致发光器件，包含权利要求1所述咔唑衍生物类胺化合物，所述咔唑衍生物类胺化合物作为有机电致发光器件的空穴传输材料。
4.一种显示装置，其特征在于，包含权利要求3所述的有机电致发光器件。
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