CN113072571B - 一种七元环热激活延迟荧光材料及其制备方法、有机发光器件 - Google Patents
一种七元环热激活延迟荧光材料及其制备方法、有机发光器件 Download PDFInfo
- Publication number
- CN113072571B CN113072571B CN202110238720.1A CN202110238720A CN113072571B CN 113072571 B CN113072571 B CN 113072571B CN 202110238720 A CN202110238720 A CN 202110238720A CN 113072571 B CN113072571 B CN 113072571B
- Authority
- CN
- China
- Prior art keywords
- membered ring
- thermal activation
- activation delayed
- delayed fluorescence
- ring thermal
- 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.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 78
- 230000003111 delayed effect Effects 0.000 title claims abstract description 48
- 238000007725 thermal activation Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title abstract description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 8
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- 229930192474 thiophene Natural products 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002189 fluorescence spectrum Methods 0.000 abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract description 6
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003107 substituted aryl group Chemical group 0.000 abstract description 6
- 238000009825 accumulation Methods 0.000 abstract description 4
- 238000010791 quenching Methods 0.000 abstract description 4
- 230000000171 quenching effect Effects 0.000 abstract description 4
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
- 229910000024 caesium carbonate Inorganic materials 0.000 description 6
- 229940125833 compound 23 Drugs 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical group OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical compound FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 2
- SWELJVAWQMCJLG-UHFFFAOYSA-N 5-bromo-2-chloro-1,3-difluorobenzene Chemical compound FC1=CC(Br)=CC(F)=C1Cl SWELJVAWQMCJLG-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 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
- 239000003208 petroleum Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-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
- -1 and Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical group C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Images
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- 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
-
- 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
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
-
- 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
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1085—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with other heteroatoms
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
技术领域
本发明涉及有机显示技术领域,特别涉及一种七元环热激活延迟荧光材料及其制备方法、有机发光器件。
背景技术
有机发光二极管(Organic Light Emission Diodes,OLED)作为新一代光学显示技术,具有低驱动电压、低功耗、高亮度、高效率、高对比度、轻薄、无视角依赖性以及反应速度快等优点,在平板显示、高效照明和柔性可穿戴设备等方面具有非常广阔的应用前景。
发光材料是OLED的核心材料,目前共发展了三代发光材料,即荧光材料、磷光材料以及热激活延迟荧光材料(Thermally Activated Delayed Fluorescence,TADF)。其中荧光材料效率较低,磷光材料需要使用贵金属且蓝光磷光材料稳定性较差,而TADF材料内量子效率可以达到100%且成本较低,因此是目前最具商业前景的研究热点。
当前普遍采用的TADF材料荧光发射光谱半峰全宽(Full Width at HalfMaximum,FWHM)值较大,导致器件色纯度低,单色性差。日本关西学院大学T.Hatekeyama教授于2016年提出了独特的硼氮多重共振结构(专利公开号:WO2020039930A1),一定程度上窄化了TADF荧光发射光谱,但是严重的效率滚降影响了器件光稳定性和工作寿命。
因此,现有技术还有待于改进和发展。
发明内容
鉴于上述现有技术的不足,本发明的目的在于提供一种七元环热激活延迟荧光材料及其制备方法、有机发光器件,旨在解决现有热激活延迟荧光材料存在严重的效率滚降,导致器件光稳定性较差和工作寿命较短的问题。
本发明的技术方案如下:
一种七元环热激活延迟荧光材料,其中,其化学结构通式为:其中,Ar1-Ar4分别独立地选自苯、噻吩、呋喃、吡啶或取代的上述芳基或杂芳基,R1-R12分别独立地选自氢、氘、氰基或烷基链中的一种,X选自氢、氘、卤素、氰基、烷基链或苯、噻吩、呋喃、咔唑、吡啶、喹啉、异喹啉以及取代的上述芳基或杂芳基。
一种七元环热激活延迟荧光材料的制备方法,其中,包括以下步骤:
原料芳香硼酸与卤代芳香基团溶于第一溶剂中,在第一预定反应条件下得到第一中间产物;
将所述第一中间产物溶于第一溶剂中,加入足量铁粉,3%氯化铵溶液,加热回流后,将溶液倒入水中,过滤得到滤液,旋蒸浓缩,硅胶柱分离得到第二中间产物;
将所述第二中间产物溶于第二溶剂中,在第二预定反应条件下得到第三中间产物芳香胺;
将第三中间产物与二氟溴苯溶于第三溶剂中,加入碳酸铯,加热回流24小时,将溶液倒入水中,过滤得到白色沉淀,使用第四溶剂重结晶得到第四中间产物;
所述第四中间产物在低温下与正丁基锂反应后,加入三溴化硼继续反应后加入N,N-二异丙基乙胺,搅拌反应后,制得所述七元环热激活延迟荧光材料。
一种七元环热激活延迟荧光材料的制备方法,其中,包括以下步骤:
原料芳香硼酸与卤代芳香基团溶于第一溶剂中,在第一预定反应条件下得到第一中间产物;
将所述第一中间产物溶于第一溶剂中,加入足量铁粉,3%氯化铵溶液,加热回流后,将溶液倒入水中,过滤得到滤液,旋蒸浓缩,硅胶柱分离得到第二中间产物;
将所述第二中间产物溶于第二溶剂中,在第二预定反应条件下得到第三中间产物芳香胺;
将第三中间产物芳香胺与5-溴-2-氯-1,3-二氟苯溶于第三溶剂中,加入碳酸铯,加热回流24小时,将溶液倒入水中,过滤得到白色沉淀,使用第四溶剂重结晶得到第五中间产物;
取代或未取代的芳基或者杂芳基与第五中间产物溶于第一溶剂中,在第一预定反应条件下的第六中间产物;
所述第六中间产物在低温下与正丁基锂反应后,加入三溴化硼继续反应后加入N,N-二异丙基乙胺,搅拌反应后,制得所述七元环热激活延迟荧光材料。
所述七元环热激活延迟荧光材料的制备方法,其中,所述第一溶剂为甲苯,第二溶剂为二甲基亚砜,第三溶剂为N,N-二甲基甲酰胺,第四溶剂为乙醇。
所述七元环热激活延迟荧光材料的制备方法,其中,所述第一预设反应条件为:催化剂为2%mol的四三苯基膦钯,碳酸钾5倍当量;反应温度为100-110°,反应时间为24小时。
所述七元环热激活延迟荧光材料的制备方法,其中,所述第二预设反应条件为:催化剂为2倍当量的叔丁醇钾,反应温度为160°,反应时间为12小时。
一种有机发光器件,其中,从上到下依次包括金属阴极,电子注入层,电子传输层,发光层,空穴传输层,空穴注入层,氧化铟锡正极,所述发光层材料为本发明所述的七元环热激活延迟荧光材料。
有益效果:与现有技术相比,本发明通过七元环的引入可以有效的改善热激活延迟荧光材料之间的堆积,减少分子间三线态淬灭,降低效率滚降,从而提高以所述七元环热激活延迟荧光材料作为发光层的器件稳定性和工作寿命;本发明同时采用独特的硼氮多重共振结构赋予了材料较窄的荧光发射光谱以及较高的外量子效率值。因此,以本发明七元环热激活延迟荧光材料作为有机电致发光器件的发光材料具有发光效率高,色纯度高和效率滚降小等优点。
附图说明
图1为本发明实施例4中有机电致发光器件的结构示意图。
图2为本发明实施例1中七元环热激活延迟荧光材料的热稳定性测试结果图。
图3为本发明实施例1中七元环热激活延迟荧光材料的发射光谱测试结果图。
具体实施方式
本发明提供一种七元环热激活延迟荧光材料及其制备方法、有机发光器件,为使本发明的目的、技术方案及效果更加清楚、明确,以下对本发明进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
现有技术虽然提出了采用独特的硼氮多重共振结构来窄化热激活延迟荧光材料的荧光发射光谱,但是其严重的效率滚降影响了器件的光稳定性和工作寿命。
基于此,本发明提供了一种七元环热激活延迟荧光材料,其化学结构通式为其中,Ar1-Ar4分别独立地选自苯、噻吩、呋喃、吡啶或取代的上述芳基或杂芳基,R1-R12分别独立地选自氢、氘、氰基或烷基链中的一种,X选自氢、氘、卤素、氰基、烷基链或苯、噻吩、呋喃、咔唑、吡啶、喹啉、异喹啉以及取代的上述芳基或杂芳基。
本实施例通过七元环的引入可以有效的改善材料之间的堆积,减少分子间三线态淬灭,降低效率滚降,从而提高器件稳定性和工作寿命;同时本实施例采用独特的硼氮多重共振结构赋予了材料较窄的荧光发射光谱以及较高的外量子效率值。因此,以本发明七元环热激活延迟荧光材料作为有机电致发光器件的发光材料具有发光效率高,色纯度高和效率滚降小等优点。
在一些实施方式中,所述X为以下基团中的一种:
在一些具体的实施方式中,所述七元环热激活延迟荧光材料为以下171种化学结构式中的一种:
在一些实施方式中,本发明还提供了一种七元环热激活延迟荧光材料的制备方法,其化学反应过程如下所示:
具体来讲,其制备方法包括以下步骤:
原料芳香硼酸与卤代芳香基团溶于第一溶剂中,在第一预定反应条件下得到第一中间产物;
将所述第一中间产物溶于第一溶剂中,加入足量铁粉,3%氯化铵溶液,加热回流后,将溶液倒入水中,过滤得到滤液,旋蒸浓缩,硅胶柱分离得到第二中间产物;
将所述第二中间产物溶于第二溶剂中,在第二预定反应条件下得到第三中间产物芳香胺;
将第三中间产物与二氟溴苯溶于第三溶剂中,加入碳酸铯,加热回流24小时,将溶液倒入水中,过滤得到白色沉淀,使用第四溶剂重结晶得到第四中间产物;
所述第四中间产物在低温下与正丁基锂反应后,加入三溴化硼继续反应后加入N,N-二异丙基乙胺,搅拌反应后,制得所述七元环热激活延迟荧光材料。
在本实施例中,所述第一溶剂为甲苯,第二溶剂为二甲基亚砜,第三溶剂为N,N-二甲基甲酰胺,第四溶剂为乙醇。所述第一预设反应条件为:催化剂为2%mol的四三苯基膦钯,碳酸钾5倍当量;反应温度为100-110℃,反应时间为24小时。所述第二预设反应条件为:催化剂为2倍当量的叔丁醇钾,反应温度为160℃,反应时间为12小时。
在一些实施方式中,还提供另一种七元环热激活延迟荧光材料的制备方法,其化学反应过程如下所示:
具体来讲,其制备方法包括以下步骤::
将第三中间产物芳香胺与5-溴-2-氯-1,3-二氟苯溶于第三溶剂中,加入碳酸铯,加热回流24小时,将溶液倒入水中,过滤得到白色沉淀,使用第四溶剂重结晶得到第五中间产物;
取代或未取代的芳基或者杂芳基与第五中间产物溶于第一溶剂中,在第一预定反应条件下的第六中间产物;
所述第六中间产物在低温下与正丁基锂反应后,加入三溴化硼继续反应后加入N,N-二异丙基乙胺,搅拌反应后,制得所述七元环热激活延迟荧光材料。
在本实施例中,所述第一溶剂为甲苯,第二溶剂为二甲基亚砜,第三溶剂为N,N-二甲基甲酰胺,第四溶剂为乙醇。所述第一预设反应条件为:催化剂为2%mol的四三苯基膦钯,碳酸钾5倍当量;反应温度为100-110℃,反应时间为24小时。
在一些实施方式中,本发明还提供一种有机发光器件,其包括发光层,所述发光层材料为本发明所述的七元环热激活延迟荧光材料。
在一些具体的实施方式中,所述有机发光器件从上至下依次包括金属阴极、电子注入层,电子传输层,发光层,空穴传输层,空穴注入层,氧化铟锡正极,所述发光层材料取自本发明任一所述七元环热激活延迟荧光材料。
下面通过具体实施例对本发明一种七元环热激活延迟荧光材料及其制备方法与性能做进一步的解释说明:
实施例1
本实施例提供一种七元环热激活延迟荧光材料,化合物1的合成路线如下所示:
所述化合物1的合成方法具体包括以下步骤:
中间体1的合成:取500mL圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入原料1(2.52克,10mmol),原料2(2.47克,12mmol),四三苯基膦钯(231.2毫克,0.2mmol),2mol/L碳酸钾水溶液20mL,200mL甲苯。加热回流24小时,冷却至室温,将溶液倒入水中,二氯甲烷萃取,有机相使用无水硫酸钠干燥后,硅胶柱分离得到中间体1(2.40克,产率72%)。
中间体2的合成:取200mL圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体1(1.67克,5mmol),还原铁粉(1.68克,30mmol),3%氯化铵溶液5mL,100mL甲苯。加热回流5小时,冷却至室温,过滤得到滤液,旋蒸浓缩后硅胶柱分离得到中间体2(1.47克,产率97%)。
中间体3的合成:取200mL圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体2(3.04克,10mmol),叔丁醇钾(2.24克,20mmol),100mL二甲基亚砜。加热回流12小时,冷却至室温,加入硝酸铵溶液淬灭反应,二氯甲烷萃取,有机相使用无水硫酸钠干燥后,硅胶柱分离得到中间体3(2.25克,产率84%)。
中间体4的合成:取200mL双颈圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体1(5.87克,22mmol),原料3(1.93克,10mmol),碳酸铯(9.77克,30mmol),100mLN,N-二甲基甲酰胺。加热回流24小时,冷却至室温,将溶液倒入水中,过滤得到白色沉淀,粗产物使用乙醇重结晶得到中间体2(5.23克,产率76%)。
化合物1的合成:取100mL Schlenk瓶,分别加入中间体2(3.44克,5mmol),50mL叔丁基苯,液氮冻抽三次,0度下缓慢加入2.4mL正丁基锂(6mmol,2.5mol/L正己烷),缓慢加热至60度继续反应4小时。冷却至-42度,缓慢加入三溴化硼(0.68mL,7mmol),缓慢升至室温继续反应2小时。冰水浴下缓慢加入N,N-二异丙基乙胺(1.65mL,10mmol),逐渐加热至120度反应24小时。反应液冷却至室温,使用乙酸钠溶液洗涤三次,收集有机相并用无水硫酸镁干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为10/1(体积比))纯化得到化合物1(0.62克,产率20%)。
实施例2
本实施例提供一种七元环热激活延迟荧光材料,化合物23的合成路线如下所示:
化合物23的合成方法具体包括以下步骤:
中间体5的合成:取200mL双颈圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体3(5.87克,22mmol),原料4(2.27克,10mmol),碳酸铯(9.77克,30mmol),100mLN,N-二甲基甲酰胺。加热回流24小时,冷却至室温,将溶液倒入水中,过滤得到白色沉淀,粗产物使用乙醇重结晶得到中间体5(5.86克,产率81%)。
中间体6的合成:取200mL圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体3(3.61克,5mmol),原料5(3.78克,22mmol),四三苯基膦钯(115.6毫克,0.1mmol),2mol/L碳酸钾水溶液10mL,100mL四氢呋喃。加热回流24小时,冷却至室温,将溶液倒入水中,过滤得到白色沉淀,粗产物使用乙醇重结晶得到中间体6(2.66克,产率69%)。
化合物23的合成:取100mL Schlenk瓶,分别加入中间体6(3.85克,5mmol),50mL叔丁基苯,液氮冻抽三次,0度下缓慢加入2.4mL正丁基锂(6mmol,2.5mol/L正己烷),缓慢加热至60度继续反应4小时。冷却至-42度,缓慢加入三溴化硼(0.68mL,7mmol),缓慢升至室温继续反应2小时。冰水浴下缓慢加入N,N-二异丙基乙胺(1.65mL,10mmol),逐渐加热至120度反应24小时。反应液冷却至室温,使用乙酸钠溶液洗涤三次,收集有机相并用无水硫酸镁干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为10/1(体积比))纯化得到化合物23(0.67克,产率18%)。
实施例3
本实施例提供一种七元环热激活延迟荧光材料,化合物68的合成路线如下所示:
化合物68的合成方法具体包括以下步骤:
中间体10的合成:同中间体3的合成,区别在于使用原料7(3.89克,15mmol)作为起始原料,得到中间体10(1.90克,产率74%)。
中间体11的合成:同中间体5的合成,区别在于使用中间体10(5.65克,22mmol),得到中间体11(5.62克,产率80%)。
中间体12的合成:同中间体6的合成,区别在于使用中间体11(3.51克,5mmol),得到中间体12(2.33克,产率65%).
化合物68的合成:同化合物23的合成,区别在于使用中间体12(3.58克,5mmol),得到化合物68(0.83克,产率24%)。
鉴于上述七元环热激活延迟荧光材料优异的发光性能,窄化的荧光发射光谱,本发明提供了上述材料作为有机发光器件的实施例。
实施例4
本发明提供了基于七元环热激活延迟荧光材料作为发光层的有机发光器件,如图1所示,从上至下依次层叠设置的金属阴极1、电子注入层2、电子传输层3、发光层4、空穴传输层5、空穴注入层6、阳极7以及玻璃基板8。其中,优选的,金属阴极1选用铝,电子注入层2选用氟化锂,电子传输层3选用具有如下结构的化合物LET003;发光层4由主体材料和客体材料共掺杂形成,其中主体材料选用具有以下结构的化合物mCBP,客体材料选用化合物68主体材料与客体材料掺杂的质量比为90:10;空穴传输层5选用具有如下结构的化合物NPB;空穴注入层6选用具有如下结构的化合物HATCN;阳极7选用氧化铟锡。
实施例5
提供一种有机电致发光器件,与实施例4提供的有机电致发光器件的区别在于:发光层材料选用化合物1。
实施例6
提供一种有机电致发光器件,与实施例4提供的有机电致发光器件的区别在于:发光层材料选用化合物23。
对本实施例1制备的七元环热激活延迟荧光材料进行热稳定性测试,结果如图2所示,从图2可以看出,所述七元环热激活延迟荧光材料的分解温度为415度,说明所述七元环热激活延迟荧光材料热稳定性优异。
对本实施例1制备的七元环热激活延迟荧光材料的发射光谱进行测试,结果如图3所示,从图3可以看出,所述七元环热激活延迟荧光材料的发射光谱仅有28nm,说明所述七元环热激活延迟荧光材料具有窄发射光谱的特性,体现了该材料良好的色纯度。
综上所述,本发明通过七元环的引入可以有效的改善材料之间的堆积,减少分子间三线态淬灭,降低效率滚降,提高器件稳定性和工作寿命;同时采用独特的硼氮多重共振结构赋予了材料较窄的荧光发射光谱以及较高的外量子效率值。
应当理解的是,本发明的应用不限于上述的举例,对本领域普通技术人员来说,可以根据上述说明加以改进或变换,所有这些改进和变换都应属于本发明所附权利要求的保护范围。
Claims (3)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110238720.1A CN113072571B (zh) | 2021-03-04 | 2021-03-04 | 一种七元环热激活延迟荧光材料及其制备方法、有机发光器件 |
PCT/CN2022/076179 WO2022183900A1 (zh) | 2021-03-01 | 2022-02-14 | 一种以热激活延迟荧光材料为发光层材料的有机发光器件 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110238720.1A CN113072571B (zh) | 2021-03-04 | 2021-03-04 | 一种七元环热激活延迟荧光材料及其制备方法、有机发光器件 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113072571A CN113072571A (zh) | 2021-07-06 |
CN113072571B true CN113072571B (zh) | 2022-07-22 |
Family
ID=76610046
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110238720.1A Active CN113072571B (zh) | 2021-03-01 | 2021-03-04 | 一种七元环热激活延迟荧光材料及其制备方法、有机发光器件 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113072571B (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022183900A1 (zh) * | 2021-03-01 | 2022-09-09 | 北京大学深圳研究生院 | 一种以热激活延迟荧光材料为发光层材料的有机发光器件 |
KR20230032326A (ko) * | 2021-08-30 | 2023-03-07 | 삼성전자주식회사 | 헤테로시클릭 화합물, 이를 포함한 유기 발광 소자 및 상기 유기 발광 소자를 포함한 전자 장치 |
CN114149458B (zh) * | 2021-11-29 | 2023-01-06 | 苏州大学 | 一种b/n类有机电致发光材料及其制备方法与应用 |
CN114195813A (zh) * | 2021-12-30 | 2022-03-18 | 中国科学技术大学 | 含硼稠环化合物及电子器件 |
CN116874517B (zh) * | 2023-09-08 | 2023-12-01 | 浙江华显光电科技有限公司 | 含硒吩化合物及其在有机发光装置的应用 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111029477B (zh) * | 2019-12-10 | 2022-10-18 | 昆山国显光电有限公司 | 一种有机电致发光器件、显示面板及显示装置 |
-
2021
- 2021-03-04 CN CN202110238720.1A patent/CN113072571B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
CN113072571A (zh) | 2021-07-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113072571B (zh) | 一种七元环热激活延迟荧光材料及其制备方法、有机发光器件 | |
KR101196093B1 (ko) | 페난스로카바졸 화합물 및 이를 이용한 유기 전계 발광 소자 | |
KR102615339B1 (ko) | 백금 (ii) 4좌 onno 착화합물 발광 재료, 제조 방법 및 유기 발광 다이오드에서 이의 응용 | |
CN109761879B (zh) | 有机蓝色荧光材料及其制备方法、有机电致发光器件 | |
CN112174918B (zh) | 一种化合物、空穴传输材料、有机电致发光器件和显示装置 | |
CN111875592A (zh) | 化合物其制备方法以及有机发光器件 | |
CN113072569A (zh) | 一种热激活延迟蓝色荧光材料与有机发光二极管 | |
CN111675693A (zh) | 一类含吖啶和菲并咪唑的d-a型发光小分子及其在电致发光器件中的应用 | |
CN112225747B (zh) | 一种热致延迟荧光性能的有机发光材料及其制备方法和应用 | |
CN110551154B (zh) | 一种含磷双环化合物及其制备方法和应用 | |
CN114409659A (zh) | 有机电致发光化合物及其制备方法和有机电致发光器件 | |
CN112125813B (zh) | 一种化合物、空穴传输材料和有机电致发光器件 | |
CN112851565B (zh) | 一种室温磷光性能的有机发光材料及其制备方法和应用 | |
CN110041268B (zh) | 一种嘧啶类双极性化合物及其在oled器件中的应用 | |
WO2022183900A1 (zh) | 一种以热激活延迟荧光材料为发光层材料的有机发光器件 | |
CN114605383B (zh) | 基于萘酐的红光延迟荧光材料和激基复合物受体材料 | |
CN113861172B (zh) | 基于苯并五元杂环的双极性荧光材料及其制备方法与有机电致发光器件 | |
CN115108919A (zh) | 一种有机电致发光化合物及有机电致发光器件 | |
CN117143030A (zh) | 萘基取代吸电片段化合物、电子传输材料及应用 | |
CN111423450B (zh) | 化合物、显示面板以及显示装置 | |
CN113087734A (zh) | 一种有机化合物掺杂材料及其制备方法和应用 | |
KR102675085B1 (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
CN112266385A (zh) | 一种吡啶并咪唑并吡咯类化合物及其应用 | |
CN108250129B (zh) | 一种以二芳基蒽酮为核心的化合物及其在有机电致发光器件上的应用 | |
CN114163451B (zh) | 一种蓝光主体材料与蓝光发光器件 |
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 | ||
GR01 | Patent grant | ||
GR01 | Patent grant |