CN109422735A - Carbazole derivative material and organic light-emitting diode element using same - Google Patents
Carbazole derivative material and organic light-emitting diode element using same Download PDFInfo
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- CN109422735A CN109422735A CN201710717334.4A CN201710717334A CN109422735A CN 109422735 A CN109422735 A CN 109422735A CN 201710717334 A CN201710717334 A CN 201710717334A CN 109422735 A CN109422735 A CN 109422735A
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- 239000000463 material Substances 0.000 title claims abstract description 135
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 82
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 74
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 74
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 71
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 300
- 229910052799 carbon Inorganic materials 0.000 claims description 300
- 125000002521 alkyl halide group Chemical group 0.000 claims description 73
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 71
- 238000006884 silylation reaction Methods 0.000 claims description 64
- 230000005540 biological transmission Effects 0.000 claims description 26
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 25
- 230000004888 barrier function Effects 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 150000001924 cycloalkanes Chemical class 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims 5
- 238000006467 substitution reaction Methods 0.000 claims 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 136
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
- 239000000126 substance Substances 0.000 description 44
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- 239000011265 semifinished product Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 13
- 229910000024 caesium carbonate Inorganic materials 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000005611 electricity Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer 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
- 230000008569 process Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004227 thermal cracking Methods 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000003760 hair shine Effects 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- -1 p- tolyl Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- SIFIJQFBERMWMU-UHFFFAOYSA-N 2,4,6-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(C(Cl)=O)C(F)=C1 SIFIJQFBERMWMU-UHFFFAOYSA-N 0.000 description 2
- MARUHZGHZWCEQU-UHFFFAOYSA-N 5-phenyl-2h-tetrazole Chemical compound C1=CC=CC=C1C1=NNN=N1 MARUHZGHZWCEQU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- 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
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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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
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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
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a carbazole derivative material and an organic light-emitting diode element using the same. A carbazole derivative material shown by general formula (1):wherein R is1One selected from the group consisting of the structures represented by the general formula (2), the general formula (3) and the general formula (4), wherein R is2To R41And R80To R89Independently selected from one of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a sulfanyl group, a silyl group, and an alkenyl group.
Description
Technical field
The present invention is about a kind of luminescent material and light-emitting component, in particular, to a kind of carbazole derivates material and organic
Light-emitting diode.
Background technique
With the progress of electronics technology, light-weight, high-efficient flat display apparatus also flourishes therewith.Organic electroluminescence
Light emitting device is excellent with its self-luminous, no angle limit, power saving, easy, at low cost, the high answer speed of technique and true color etc.
Point, the mainstream for making it be expected to become next-generation flat display apparatus.
In general, Organnic electroluminescent device includes anode, organic luminous layer and cathode.When impose DC current in
When Organnic electroluminescent device, hole and electronics inject organic luminous layer by anode and cathode respectively, since extra electric field is made
At potential difference so that carrier move, meet in organic luminous layer and generate in conjunction with, and by electronics in conjunction with hole institute
The exciton (exciton) of generation can excite the light emitting molecule in organic luminous layer, and then the light emitting molecule of excitation state is with light
Form gives off energy.
Organnic electroluminescent device mostly uses host and guest to shine two-body system now, and wherein organic luminous layer includes main body
(host) material and object (guest) material, hole and electronics, which are mainly transferred in material of main part, to be combined to generate
Energy, this energy will transfer in guest materials to generate light.Guest materials can be divided into fluorescence luminescent material and phosphorescence shines
Material selects phosphorescent light-emitting materials appropriate, can theoretically make internal quantum up to 100%, therefore phosphorescence shines material
Material has recently become the epochmaking developing direction of electroluminescent organic material.
In the development of Blue-light emitting host material, the triplet energy gap of material of main part necessarily is greater than or equal to the three of guest materials
Weight state energy gap, the loss of energy is caused to avoid energy passback, and then leads to luminous efficiency (also known as current efficiency；
Current efficiency) it is low short with the service life the problems such as, therefore having biggish triplet energies is necessary condition.It is at present
So that Blue-light emitting host material is possessed biggish triplet energy gap, is to be added on ortho position with single phenyl ring as research center of gravity
With the sub-feature that conducts electricity (such as OXD or TAZ) and pass hole characteristic (such as Cbz) group, by steric hindrance effect so that
The pi-conjugated blocking of molecule simultaneously forms quadripole molecule.
In addition, the material of organic luminous layer selects other than the matching of energy gap, it is also necessary to there is high pyrolysis temperature, to keep away
Exempt from high temperature and generate thermal cracking, and then stability is caused to decline.
For this purpose, the present inventor's carefulness is studied, carbazole derivates material and organic light-emitting diode element are proposed,
Can meet the needs of high triplet energy gap and good thermal stability.
Summary of the invention
In view of the above subject, it is an object of the invention to provide one kind can meet the needs of high triplet energy gap and good
The carbazole derivates material and organic light-emitting diode element of thermal stability.
In order to achieve the above object, a kind of carbazole derivates material according to the present invention, the structure with general formula (1):
Wherein R1Selected from one of general formula (2), general formula (3) and structure of general formula (4),
Wherein, R2To R41With R80To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy,
One of alkylhalide group, sulfanyl, silicyl and alkenyl.
In one embodiment, alkyl is the substituted straight chained alkyl of carbon number 1~6, the straight chained alkyl not replaced, carbon number
The branched alkyl of 3~6 substituted branched alkyl, carbon number 3~6 not replaced, naphthenic base are the substituted cycloalkanes of carbon number 3~6
The naphthenic base of base, carbon number 3~6 not replaced, alkoxy are that the substituted unbranched alkoxy of carbon number 1~6, carbon number 1~6 do not take
The unbranched alkoxy in generation, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 the branched alkoxy not replaced, alkylhalide group
For the substituted branch of the substituted straight chain alkylhalide group of carbon number 1~6, the straight chain alkylhalide group of carbon number 1~6 not replaced, carbon number 3~6
The branch alkylhalide group of chain alkylhalide group, carbon number 3~6 not replaced, sulfanyl are substituted straight chain sulfanyl, the carbon number of carbon number 1~6
1~6 straight chain sulfanyl not replaced, the substituted branch sulfanyl of carbon number 3~6, carbon number 3~6 the branch sulphur not replaced
Alkyl, silylation are the straight chain silylation not replaced, the carbon number 3~6 of the substituted straight chain silylation of carbon number 1~6, carbon number 1~6
Substituted branch silylation, carbon number 3~6 the branch silylation not replaced, alkenyl be carbon number 2~6 substituted straight chain alkene
The branch of base, the straight-chain alkenyl of carbon number 2~6 not replaced, the substituted branched-chain alkenyl of carbon number 3~6 or carbon number 3~6 not replaced
Alkenyl.
In order to achieve the above object, a kind of carbazole derivates material according to the present invention, the structure with general formula (5):
Wherein R46Selected from general formula (2), general formula (3), general formula (4), hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base,
One of alkoxy, alkylhalide group, sulfanyl, silylation and alkenyl,
Wherein, R28To R41And R47To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy,
One of alkylhalide group, sulfanyl, silicyl and alkenyl.
In one embodiment, alkyl is the substituted straight chained alkyl of carbon number 1~6, the straight chained alkyl not replaced, carbon number
The branched alkyl of 3~6 substituted branched alkyl, carbon number 3~6 not replaced, naphthenic base are the substituted cycloalkanes of carbon number 3~6
The naphthenic base of base, carbon number 3~6 not replaced, alkoxy are that the substituted unbranched alkoxy of carbon number 1~6, carbon number 1~6 do not take
The unbranched alkoxy in generation, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 the branched alkoxy not replaced, alkylhalide group
For the substituted branch of the substituted straight chain alkylhalide group of carbon number 1~6, the straight chain alkylhalide group of carbon number 1~6 not replaced, carbon number 3~6
The branch alkylhalide group of chain alkylhalide group, carbon number 3~6 not replaced, sulfanyl are substituted straight chain sulfanyl, the carbon number of carbon number 1~6
1~6 straight chain sulfanyl not replaced, the substituted branch sulfanyl of carbon number 3~6, carbon number 3~6 the branch sulphur not replaced
Alkyl, silylation are the straight chain silylation not replaced, the carbon number 3~6 of the substituted straight chain silylation of carbon number 1~6, carbon number 1~6
Substituted branch silylation, carbon number 3~6 the branch silylation not replaced, alkenyl be carbon number 2~6 substituted straight chain alkene
The branch of base, the straight-chain alkenyl of carbon number 2~6 not replaced, the substituted branched-chain alkenyl of carbon number 3~6 or carbon number 3~6 not replaced
Alkenyl.
In order to achieve the above object, a kind of organic light-emitting diode element according to the present invention, comprising: first electrode layer, second
Electrode layer and organic light-emitting units, wherein organic light-emitting units are configured between first electrode layer and the second electrode lay, organic
Luminescence unit includes the carbazole derivates material as shown in general formula (1),
Wherein R1Selected from one of general formula (2), general formula (3) and structure of general formula (4),
Wherein, R2To R41With R80To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy,
One of alkylhalide group, sulfanyl, silicyl and alkenyl.
In one embodiment, alkyl is the substituted straight chained alkyl of carbon number 1~6, the straight chained alkyl not replaced, carbon number
The branched alkyl of 3~6 substituted branched alkyl, carbon number 3~6 not replaced, naphthenic base are the substituted cycloalkanes of carbon number 3~6
The naphthenic base of base, carbon number 3~6 not replaced, alkoxy are that the substituted unbranched alkoxy of carbon number 1~6, carbon number 1~6 do not take
The unbranched alkoxy in generation, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 the branched alkoxy not replaced, alkylhalide group
For the substituted branch of the substituted straight chain alkylhalide group of carbon number 1~6, the straight chain alkylhalide group of carbon number 1~6 not replaced, carbon number 3~6
The branch alkylhalide group of chain alkylhalide group, carbon number 3~6 not replaced, sulfanyl are substituted straight chain sulfanyl, the carbon number of carbon number 1~6
1~6 straight chain sulfanyl not replaced, the substituted branch sulfanyl of carbon number 3~6, carbon number 3~6 the branch sulphur not replaced
Alkyl, silylation are the straight chain silylation not replaced, the carbon number 3~6 of the substituted straight chain silylation of carbon number 1~6, carbon number 1~6
Substituted branch silylation, carbon number 3~6 the branch silylation not replaced, alkenyl be carbon number 2~6 substituted straight chain alkene
The branch of base, the straight-chain alkenyl of carbon number 2~6 not replaced, the substituted branched-chain alkenyl of carbon number 3~6 or carbon number 3~6 not replaced
Alkenyl.
In one embodiment, organic light-emitting units include organic luminous layer.
In one embodiment, organic light-emitting units further include hole transmission layer and electron transfer layer, wherein organic hair
Photosphere is configured between hole transmission layer and electron transfer layer.
In one embodiment, organic light-emitting units further include hole transmission layer, electronic barrier layer, electron transfer layer and
Electron injecting layer, hole-transporting layer is to sequentially configuring electronic barrier layer, organic luminous layer and electronics between electron injecting layer
Transport layer.
In one embodiment, organic luminous layer includes material of main part and guest materials, and material of main part is derivative for carbazole
Object material, guest materials are phosphorescent light-emitting materials.
In one embodiment, material of main part organic luminous layer content between 60 volume % to 95 volume % it
Between.
In one embodiment, guest materials organic luminous layer content between 5 volume % between 40 volume %.
In order to achieve the above object, a kind of organic light-emitting diode element according to the present invention, comprising: first electrode layer, second
Electrode layer and organic light-emitting units, are configured between first electrode layer and the second electrode lay, and organic light-emitting units include as logical
Carbazole derivates material shown in formula (5),
In one embodiment, R46Selected from general formula (2), general formula (3), general formula (4), hydrogen atom, fluorine atom, cyanogen
One of base, alkyl, naphthenic base, alkoxy, alkylhalide group, sulfanyl, silylation and alkenyl,
Wherein, R28To R41And R47To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy,
One of alkylhalide group, sulfanyl, silicyl and alkenyl.
In one embodiment, alkyl is the substituted straight chained alkyl of carbon number 1~6, the straight chained alkyl not replaced, carbon number
The branched alkyl of 3~6 substituted branched alkyl, carbon number 3~6 not replaced, naphthenic base are the substituted cycloalkanes of carbon number 3~6
The naphthenic base of base, carbon number 3~6 not replaced, alkoxy are that the substituted unbranched alkoxy of carbon number 1~6, carbon number 1~6 do not take
The unbranched alkoxy in generation, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 the branched alkoxy not replaced, alkylhalide group
For the substituted branch of the substituted straight chain alkylhalide group of carbon number 1~6, the straight chain alkylhalide group of carbon number 1~6 not replaced, carbon number 3~6
The branch alkylhalide group of chain alkylhalide group, carbon number 3~6 not replaced, sulfanyl are substituted straight chain sulfanyl, the carbon number of carbon number 1~6
1~6 straight chain sulfanyl not replaced, the substituted branch sulfanyl of carbon number 3~6, carbon number 3~6 the branch sulphur not replaced
Alkyl, silylation are the straight chain silylation not replaced, the carbon number 3~6 of the substituted straight chain silylation of carbon number 1~6, carbon number 1~6
Substituted branch silylation, carbon number 3~6 the branch silylation not replaced, alkenyl be carbon number 2~6 substituted straight chain alkene
The branch of base, the straight-chain alkenyl of carbon number 2~6 not replaced, the substituted branched-chain alkenyl of carbon number 3~6 or carbon number 3~6 not replaced
Alkenyl.
In one embodiment, organic light-emitting units include organic luminous layer.
In one embodiment, organic light-emitting units further include hole transmission layer and electron transfer layer, wherein organic hair
Photosphere is configured between hole transmission layer and electron transfer layer.
In one embodiment, organic light-emitting units further include hole transmission layer, electronic barrier layer, electron transfer layer and
Electron injecting layer, hole-transporting layer is to sequentially configuring electronic barrier layer, organic luminous layer and electronics between electron injecting layer
Transport layer.
In one embodiment, organic luminous layer includes material of main part and guest materials, and the material of main part is carbazole
Derivant material, guest materials are phosphorescent light-emitting materials.
In one embodiment, material of main part organic luminous layer content between 60 volume % to 95 volume % it
Between.
In one embodiment, guest materials organic luminous layer content between 5 volume % between 40 volume %.
From the above, carbazole derivates material of the invention and organic light-emitting diode element are with 1,3,5- tri- (click
Azoles -9- base) benzene (TCP) or 1,2,4,5- tetra- (9H- carbazole -9- base) benzene (o-4Cbz) are used as core, and can be respectively at ortho position
Different types of subbase group that conducts electricity is connected, the quadripole of the phosphorescence Organic Light Emitting Diode of high efficiency and good thermal stability is formed
Host emitter.In addition, carbazole derivates material of the invention can also be used for hole transmission layer.Furthermore 1,2,4,5- tetra- (9H- click
Azoles -9- base) benzene (o-4Cbz) itself also can be used as host emitter material and hole transport layer material.
Detailed description of the invention
Fig. 1 is a kind of diagrammatic cross-section of organic light-emitting diode element of third embodiment of the invention.
Fig. 2 is a kind of diagrammatic cross-section of organic light-emitting diode element of four embodiment of the invention.
Fig. 3 is a kind of diagrammatic cross-section of organic light-emitting diode element of fifth embodiment of the invention.
Specific embodiment
Hereinafter with reference to relevant drawings, illustrate preferred embodiment according to the present invention a kind of carbazole derivates material and
Organic light-emitting diode element, wherein identical element will be illustrated with identical appended drawing reference.
Carbazole derivates material
A kind of carbazole derivates material disclosed in first embodiment according to the present invention, the structure with general formula (1):
Wherein R1Selected from one of general formula (2), general formula (3) and structure of general formula (4).
Wherein, R2To R41With R80To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy,
One of alkylhalide group, sulfanyl, silicyl and alkenyl.
Here, alkyl be the substituted straight chained alkyl of carbon number 1~6, the straight chained alkyl not replaced, carbon number 3~6 it is substituted
The branched alkyl of branched alkyl, carbon number 3~6 not replaced, naphthenic base are the substituted naphthenic base of carbon number 3~6, carbon number 3~6
The naphthenic base not replaced, alkoxy are the straight chain alcoxyl of the substituted unbranched alkoxy of carbon number 1~6, carbon number 1~6 not replaced
Base, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 the branched alkoxy not replaced, alkylhalide group is carbon number 1~6
Substituted branch alkylhalide group, the carbon number of the straight chain alkylhalide group not replaced of substituted straight chain alkylhalide group, carbon number 1~6, carbon number 3~6
3~6 branch alkylhalide group not replaced, sulfanyl are that the substituted straight chain sulfanyl of carbon number 1~6, carbon number 1~6 do not replace
Straight chain sulfanyl, the substituted branch sulfanyl of carbon number 3~6, carbon number 3~6 the branch sulfanyl not replaced, silylation is
The substituted straight chain silylation of carbon number 1~6, the straight chain silylation of carbon number 1~6 not replaced, carbon number 3~6 substituted branch
The branch silylation of silylation, carbon number 3~6 not replaced, alkenyl are the substituted straight-chain alkenyl of carbon number 2~6, carbon number 2~6
The substituted branched-chain alkenyl of the straight-chain alkenyl, carbon number 3~6 that do not replace or the branched-chain alkenyl of carbon number 3~6 not replaced.
The structure of the general formula (1) of present embodiment can be used as the main body material of organic luminous layer in organic light-emitting diode element
Material.Wherein preferred example is to work as R1For general formula (2) structure when, R2To R36It is for hydrogen atom independently, i.e., chemical
Formula (1): o-3CbzBz.
Also or, work as R1For general formula (3) structure when, R2To R27With R37To R41For hydrogen atom independently, i.e.,
Chemical formula (2): o-3CbzOXD.
Also or, work as R1For general formula (4) structure when, R2To R27With R80To R89For hydrogen atom independently, i.e.,
Chemical formula (3): o-3CbzTAZ.
A kind of carbazole derivates material disclosed in second embodiment according to the present invention, the structure with general formula (5):
Wherein R46Selected from general formula (2), general formula (3), general formula (4), hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base,
One of alkoxy, alkylhalide group, sulfanyl, silylation and alkenyl,
Wherein, R28To R41And R47To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy,
One of alkylhalide group, sulfanyl, silicyl and alkenyl.
Here, alkyl be the substituted straight chained alkyl of carbon number 1~6, the straight chained alkyl not replaced, carbon number 3~6 it is substituted
The branched alkyl of branched alkyl, carbon number 3~6 not replaced, naphthenic base are the substituted naphthenic base of carbon number 3~6, carbon number 3~6
The naphthenic base not replaced, alkoxy are the straight chain alcoxyl of the substituted unbranched alkoxy of carbon number 1~6, carbon number 1~6 not replaced
Base, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 the branched alkoxy not replaced, alkylhalide group is carbon number 1~6
Substituted branch alkylhalide group, the carbon number of the straight chain alkylhalide group not replaced of substituted straight chain alkylhalide group, carbon number 1~6, carbon number 3~6
3~6 branch alkylhalide group not replaced, sulfanyl are that the substituted straight chain sulfanyl of carbon number 1~6, carbon number 1~6 do not replace
Straight chain sulfanyl, the substituted branch sulfanyl of carbon number 3~6, carbon number 3~6 the branch sulfanyl not replaced, silylation is
The substituted straight chain silylation of carbon number 1~6, the straight chain silylation of carbon number 1~6 not replaced, carbon number 3~6 substituted branch
The branch silylation of silylation, carbon number 3~6 not replaced, alkenyl are the substituted straight-chain alkenyl of carbon number 2~6, carbon number 2~6
The substituted branched-chain alkenyl of the straight-chain alkenyl, carbon number 3~6 that do not replace or the branched-chain alkenyl of carbon number 3~6 not replaced.
The structure of the general formula (5) of present embodiment also can be used as the main body of organic luminous layer in organic light-emitting diode element
Material, wherein preferred example is to work as R46To R79For hydrogen atom independently, i.e. chemical formula (4): o-4Cbz.
Also or, work as R46For general formula (2) structure when, R28To R36With R47To R79For hydrogen atom independently,
That is chemical formula (5): o-4CbzBz.
Also or, work as R46For general formula (3) structure when, R37To R41With R47To R79For hydrogen atom independently,
That is chemical formula (6): o-4CbzOXD.
Also or, work as R46For general formula (4) structure when, R47To R89For hydrogen atom independently, i.e. chemical formula
(7): o-4CbzTAZ.
In chemical formula (1)~(3) and (5)~(7), using structure shown in general formula (2)~(4) as the subbase that conducts electricity
Group, and carbazole of arranging in pairs or groups (Carbazole), as hole group is passed, the method for carrying out single phenyl ring ortho position modification is efficient to be formed
The quadripole material of main part of rate phosphorescence Organic Light Emitting Diode.In other words, material of main part can have simultaneously in same intramolecular
The subbase group that conducts electricity and biography hole group, to reach the characteristic of bipolarity carrier transport.
In addition, the guest materials of collocation material of main part can be any hair organic suitable for organic light-emitting diode element
The material of photosphere, such as can be chemical formula (8) (Ir (2-phq)3), chemical formula (9) (Ir (ppy)3) and chemical formula (10)
(FIrpic) one of compound represented, but it's not limited to that for guest materials.
It is noted that the structure as shown in general formula (1) and general formula (5) disclosed in first and second embodiment,
Other than it can be used for organic luminous layer, it can also be used to each film layer in organic light-emitting units, specifically, for example hole is injected
Layer, hole transmission layer, electronic barrier layer, electron transfer layer or electron injecting layer etc..Here, particularly suitable for hole transport
Layer.
Organic light-emitting diode element
Referring to FIG. 1, a kind of organic light-emitting diode element 100 disclosed in third embodiment includes the according to the present invention
One electrode layer 120, the second electrode lay 140 and organic light-emitting units 160.Wherein, first electrode layer 120 can be transparent electrode
Material, e.g. indium tin oxide (ITO), the material of the second electrode lay 140 can be metal, transparent conductor or other suitable
Conductive material.However, first electrode layer 120 is also possible to metal, transparent conductor or other suitable conductive material, and
Two electrode layers 140 are also possible to transparent electrode material.Specifically, the first electrode layer 120 of present embodiment and the second electricity
Pole layer 140 at least one be transparent electrode material.In this way, which the light that is issued of organic light-emitting units 160 can be via
Transparent electrode, which radiates, to be come, and organic light-emitting diode element 100 is made to shine.
In addition, again referring to FIG. 1, organic light-emitting units 160 may include hole transmission layer 162, an electronic barrier layer 164,
Organic luminous layer 166, electron transfer layer 168 and electron injecting layer 169.Wherein, hole transmission layer 162 is to electron injecting layer
Electronic barrier layer 164, organic luminous layer 166 and electron transfer layer 168 are sequentially configured between 169.
Here, the material of hole transmission layer 162 can be bis- [4- [N, N '-two (p- tolyl) amino] phenyl] rings of 1,1-
Hexane (TAPC), N, N- is bis--(1- naphthalene)-N, N- diphenyl -1,1- biphenyl -4,4- diamines (NPB) or N-N'- diphenyl-N-
The materials such as bis- (3- aminomethyl phenyl)-[1-1'- the biphenyl] -4-4'- diamines (TPD) of N'.Wherein, the thickness example of hole transmission layer 162
It such as can be in the range of 0nm to 100nm.In the present embodiment, hole transmission layer 162 can promote hole by first electrode layer
The rate of 120 injection organic luminous layers 166, and the driving voltage of organic light-emitting diode element 100 is reduced simultaneously.
The material of electronic barrier layer 164 can be N,-two carbazyl -3,5- benzene (mCP) of N ' or other with low electronics parent
With the material of power.In the present embodiment, the thickness of electronic barrier layer 164 for example can be in the range of 0nm to 30nm.At this
In embodiment, electronic barrier layer 164 can further promote hole and be delivered to organic luminous layer 166 by hole transmission layer 162
Rate.
In addition, the thickness of organic luminous layer 166 for example can be in the range of 5nm to 60nm, and organic luminous layer 166 wraps
Include material of main part and guest materials.Wherein, material of main part can have the structure as shown in general formula (1):
Wherein R1Selected from one of general formula (2), general formula (3) and structure of general formula (4),
Wherein, R2To R41With R80To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy,
One of alkylhalide group, sulfanyl, silicyl and alkenyl.
Here, alkyl be the substituted straight chained alkyl of carbon number 1~6, the straight chained alkyl not replaced, carbon number 3~6 it is substituted
The branched alkyl of branched alkyl, carbon number 3~6 not replaced, naphthenic base are the substituted naphthenic base of carbon number 3~6, carbon number 3~6
The naphthenic base not replaced, alkoxy are the straight chain alcoxyl of the substituted unbranched alkoxy of carbon number 1~6, carbon number 1~6 not replaced
Base, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 the branched alkoxy not replaced, alkylhalide group is carbon number 1~6
Substituted branch alkylhalide group, the carbon number of the straight chain alkylhalide group not replaced of substituted straight chain alkylhalide group, carbon number 1~6, carbon number 3~6
3~6 branch alkylhalide group not replaced, sulfanyl are that the substituted straight chain sulfanyl of carbon number 1~6, carbon number 1~6 do not replace
Straight chain sulfanyl, the substituted branch sulfanyl of carbon number 3~6, carbon number 3~6 the branch sulfanyl not replaced, silylation is
The substituted straight chain silylation of carbon number 1~6, the straight chain silylation of carbon number 1~6 not replaced, carbon number 3~6 substituted branch
The branch silylation of silylation, carbon number 3~6 not replaced, alkenyl are the substituted straight-chain alkenyl of carbon number 2~6, carbon number 2~6
The substituted branched-chain alkenyl of the straight-chain alkenyl, carbon number 3~6 that do not replace or the branched-chain alkenyl of carbon number 3~6 not replaced.
The structure of the general formula (1) of present embodiment can be used as the main body material of organic luminous layer in organic light-emitting diode element
Material, wherein preferred example is to work as R1For general formula (2) structure when, R2To R36It is for hydrogen atom independently, i.e., chemical
Formula (1): o-3CbzBz.
Also or, work as R1For general formula (3) structure when, R2To R27With R37To R41For hydrogen atom independently, i.e.,
Chemical formula (2): o-3CbzOXD.
Also or, work as R1For general formula (4) structure when, R2To R27With R80To R89For hydrogen atom independently, i.e.,
Chemical formula (3): o-3CbzTAZ.
In addition, material of main part can also have the structure as shown in general formula (5):
Wherein R46Selected from general formula (2), general formula (3), general formula (4), hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base,
One of alkoxy, alkylhalide group, sulfanyl, silylation and alkenyl,
Wherein, R28To R41And R47To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy,
One of alkylhalide group, sulfanyl, silicyl and alkenyl.
Here, alkyl be the substituted straight chained alkyl of carbon number 1~6, the straight chained alkyl not replaced, carbon number 3~6 it is substituted
The branched alkyl of branched alkyl, carbon number 3~6 not replaced, naphthenic base are the substituted naphthenic base of carbon number 3~6, carbon number 3~6
The naphthenic base not replaced, alkoxy are the straight chain alcoxyl of the substituted unbranched alkoxy of carbon number 1~6, carbon number 1~6 not replaced
Base, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 the branched alkoxy not replaced, alkylhalide group is carbon number 1~6
Substituted branch alkylhalide group, the carbon number of the straight chain alkylhalide group not replaced of substituted straight chain alkylhalide group, carbon number 1~6, carbon number 3~6
3~6 branch alkylhalide group not replaced, sulfanyl are that the substituted straight chain sulfanyl of carbon number 1~6, carbon number 1~6 do not replace
Straight chain sulfanyl, the substituted branch sulfanyl of carbon number 3~6, carbon number 3~6 the branch sulfanyl not replaced, silylation is
The substituted straight chain silylation of carbon number 1~6, the straight chain silylation of carbon number 1~6 not replaced, carbon number 3~6 substituted branch
The branch silylation of silylation, carbon number 3~6 not replaced, alkenyl are the substituted straight-chain alkenyl of carbon number 2~6, carbon number 2~6
The substituted branched-chain alkenyl of the straight-chain alkenyl, carbon number 3~6 that do not replace or the branched-chain alkenyl of carbon number 3~6 not replaced.
The structure of the general formula (5) of present embodiment also can be used as the main body of organic luminous layer in organic light-emitting diode element
Material, wherein preferred example is to work as R46To R79For hydrogen atom independently, i.e. chemical formula (4): o-4Cbz.
Also or, work as R46For general formula (2) structure when, R28To R36With R47To R79For hydrogen atom independently,
That is chemical formula (5): o-4CbzBz.
Also or, work as R46For general formula (3) structure when, R37To R41With R47To R79For hydrogen atom independently,
That is chemical formula (6): o-4CbzOXD.
Also or, work as R46For general formula (4) structure when, R47To R89For hydrogen atom independently, i.e. chemical formula
(7): o-4CbzTAZ.
In addition, material of main part is, for example, between 60 volume % between 95 volume % in the content in organic luminous layer 166,
And guest materials in the content in organic luminous layer 166 for example between 5 volume % between 40 volume %.
Furthermore guest materials can be any material suitable for organic luminous layer 166, such as can be compound
(8)(Ir(2-phq)3), compound (9) (Ir (ppy)3One of) and compound (10) (FIrpic) compound represented, but
It is not limited only to this.
In addition, the material of electron transfer layer 168 for example can be three-(8- Hydroxy-quinolin) aluminium (Alq3), bis- (10- hydroxyls
Benzo-[h] quinoline (quinolinato)) beryllium (BeBq2) etc. metals misfit object or-(4- xenyl) -5- (4- tert-butyl benzene
Base) -1,3,4-Diazole (PBD), 3- (4- xenyl) -4- phenyl -5- tert-butyl-phenyl -1,2,4- triazole (TAZ), 2,2 ',
2 "-(three base of 1,3,5- benzin (Benzinetriyl))-three (1- phenyl -1-H- benzimidazole) (TPBI), bis- (4- of diphenyl
(pyridin-3-yl) phenyl) silane (DPPS) 3,3'- [5'- [3- (3- pyridyl group) phenyl] [1,1':3', 1 "-terphenyl] -3,
3 "-diyl] heterocyclic compounds such as double pyridines (TmPyPB), but it is not limited only to this.In the present embodiment, electron transfer layer 168
Thickness for example can be in the range of 0nm to 100nm.In the present embodiment, electron transfer layer 168 can promote electronics by
Two electrode layers 140 are transferred in organic luminous layer 166, to increase the rate of electron-transport.Furthermore the material of electron injecting layer 169
Material for example can be LiF, and thickness is, for example, 0.9nm.
In addition, Fig. 2 is a kind of section signal of organic light-emitting diode element 200 disclosed in four embodiment of the invention
Figure.Organic light-emitting diode element 200 is similar to organic light-emitting diode element 100, therefore identical element is having the same
Feature and function are indicated herein with identical component symbol, and are not repeated to illustrate.
Referring to FIG. 2, in the present embodiment, organic light-emitting units 160 may include hole transmission layer 162, organic light emission
Layer 166 and electron transfer layer 168, organic luminous layer 166 are set between hole transmission layer 162 and electron transfer layer 168.
In addition, Fig. 3 is a kind of section signal of organic light-emitting diode element 300 disclosed in fifth embodiment of the invention
Figure.Organic light-emitting diode element 300 is similar to organic light-emitting diode element 100, therefore identical element is having the same
Feature and function are indicated herein with identical component symbol, and are not repeated to illustrate.
Referring to FIG. 3, in the present embodiment, organic light-emitting units 160 may include organic luminous layer 166.
In addition, organic light-emitting diode element of the invention is not limited in the embodiment of third, the 4th and the 5th institute public affairs
The aspect opened, this is used by way of example only.
In the embodiment of aforementioned third, the 4th and the 5th, the disclosed structure as shown in general formula (1) and general formula (5),
Other than it can be used for organic luminous layer, it can also be used to each film layer in organic light-emitting units, specifically, for example hole is injected
Layer, hole transmission layer, electronic barrier layer, electron transfer layer or electron injecting layer etc..Here, particularly suitable for hole transport
Layer.
The synthesis process of above-mentioned chemical formula (1) to chemical formula (7) is described in detail referring to multiple embodiments.
Embodiment 1: the synthesis of chemical formula (1) compound o-3CbzBz
(i): 2- aminodiphenylamine, triethylamine (TEA) and methylene chloride
(ii): acetic acid reflux
(iii): Cbz, cesium carbonate (Cs2CO3) and 160 DEG C under argon gas of dimethyl sulfoxide
Firstly, by 2,4,6- trifluorobenzoyl chloride (0.97g；4.98mmol) it is dissolved in methylene chloride (DCM；In 6mL), and delay
Slowly it adds to dissolved with triethylamine (1.4mL) and 2- aminodiphenylamine (1.01g；In methylene chloride (6mL) solution 5.48mmol), hold
It is continuous to be stirred to react 12 hours.Then, it with water (20mL*1) reaction mixture, then is neutralized with 1N hydrochloric acid (20mL*2).
Organic layer is dried and concentrated to obtain crude intermediate product with anhydrous magnesium sulfate, then is flowed back 24 hours and be dehydrated with acetic acid (20mL)
Cyclisation.Later, solvent is removed with vacuum distillation and obtains semifinished product.Semifinished product is dissolved in methylene chloride, and with 0.5M K2CO3
(aq) it cleans twice.Collected organic layer is simultaneously dry with anhydrous magnesium sulfate, and is concentrated to get crude object, then with silica gel column chromatography
(eluent is ethyl acetate/dichloromethane=1/30) purifying, obtains 1 (1.31g of white powder；Yield 81%).m.p.162-
163℃；1H NMR(400MHz,CD2Cl2):d 7.88-7.86(m,1H),7.49-7.29(m,8H),7.75-7.68(m,2H)
；13C NMR(100MHz,CD2Cl2):d 165.79(m),163.28(m),160.71(m),143.95,142.28,136.87,
136.24,130.20,129.27,126.99,124.48,123.51,120.74,111.17,101.23(m)；HRMS
C19H12F3N2(M+) calculated value 325.0953, observed value 325.0943.Anal.C19H11F3N2Calculated value: C, 70.37；H,3.42；
N,8.64；Discovery value C, 70.45；H,3.68；N,8.48.
Then, by cesium carbonate (1.47g under argon system；4.51mmol), carbazole (0.52g；It is 3.11mmol) and white
1 (0.32g of powder；0.99mmol) it is blended in dimethyl sulfoxide (2.5mL；160 DEG C 0.40M) are heated to react 24 hours.Later,
Mixture is diluted with water, and filters to obtain yellow semifinished product.Using silica gel column chromatography, (eluent is hexane/dichloromethane to semifinished product again
Alkane=1/2) purifying, obtain white powder o-3CbzBz (0.66g；Yield 87%).O-3bzBz utilizes methylene chloride/ethyl alcohol again
Crystallization.It distils twice under hot evaporation and deposition before producing device.m.p.314-315℃；1H NMR(400MHz,
CD2Cl2): d 8.10 (d, J=7.68,2H), 8.03 (d, J=7.44,4H), 7.92 (s, 2H), 7.84 (d, J=8.24,2H),
7.63 (d, J=8.20,2H), 7.47-7.40 (m, 4H), 7.31-7.18 (m, 9H), 7.10-6.95 (m, 6H), 6.88 (t, J=
7.72,1H), 6.67 (d, J=8.08,1H), 6.54 (d, J=7.60,2H)；13C NMR(100MHz,CD2Cl2):d
145.82,143.18,142.56,142.43,142.19,141.83,140.38,136.03,135.46,129.68,129.24,
128.77,127.94,126.97,126.49,126.34,126.02,124.80,124.61,124.10,123.72,122.74,
121.60,121.06,120.98,120.88,120.76,120.26,120.11,112.78,110.68,110.32,110.28；
HRMS C55H35N5(M+) calculated value 766.2971, observed value 766.2960.Anal.C55H35N5Calculated value: C, 86.25；H,
4.61；N,9.14；Discovery value C, 86.10；H,4.63；N,9.12..
Embodiment 2: the synthesis of chemical formula (2) compound o-3CbzOXD
2,4,6- trifluorobenzoyl chloride (1.02g；5.24mmol) with 5- phenyl -1H-TETRAZOLE (0.92g；6.31mmol)
It is reacted 24 hours in pyridine (10mL) at 95 DEG C.When reaction completion, vacuum is utilized to remove pyridine.Semifinished product is with silica gel tubing string layer
(eluent is methylene chloride) purifying is analysed, white solid 2 is obtained.
Then, under argon system, cesium carbonate (1.47g；4.51mmol), carbazole (0.52g；3.11mmol) and white powder
2 (0.27g of end；0.99mmol) it is blended in dimethyl sulfoxide (2.5ml；0.4M), 160 DEG C are heated to react 24 hours.React it
Afterwards, it is diluted with water and yellow semifinished product is obtained by filtration.Yellow semifinished product solid is obtained with methylene chloride and acetone recrystallization purifying
o-3CbzOXD.Before the use, o-3CbzOXD distils twice under hot evaporation and film forming condition.
Embodiment 3: the synthesis of chemical formula (3) compound o-3CbzTAZ
Under argon system, by aniline (1.10mL；12.0mmol) and alchlor (0.40g；3.00mmol) at 140 DEG C
It is stirred to react 2~2.5 hours.The white powder 2 that N-Methyl pyrrolidone (1mL) will be dissolved in is added in aforementioned mixture, 200
It is heated 7~10 hours at DEG C.Reaction mixture is poured into ice water, sediment is collected and is made it dry.During first time
Conversion is not complete, therefore crude mixture reacts primary again.Collect crude product and after second of process with methylene chloride and second
Acetoacetic ester carries out recrystallization purifying and obtains product 3.
Then, under argon system, cesium carbonate (1.47g；4.51mmol), carbazole (0.52g；3.11mmol) and product 3
(0.35g；0.99mmol) it is blended in dimethyl sulfoxide (2.5ml；0.4M), 160 DEG C are heated to react 24 hours.After reaction,
It is diluted with water and yellow semifinished product is obtained by filtration.Yellow semifinished product solid obtains o- with methylene chloride and acetone recrystallization purifying
3CbzTAZ.Before the use, o-3CbzTAZ distils twice under hot evaporation and film forming condition.
Embodiment 4: the synthesis of chemical formula (4) compound o-4Cbz
(i): CBz, cesium carbonate (Cs2CO3) and 160 DEG C under argon gas of dimethyl sulfoxide
Under argon system, cesium carbonate (11.70g；35.90mmol), carbazole (4.21g；25.17mmol) and 1,2,4,5-
Phenyl tetrafluoride (0.9g；6.00mmol) it is blended in dimethyl sulfoxide (15ml；0.4M), 160 DEG C are heated to react 24 hours.React it
Afterwards, it is diluted with 300mL water and yellow semifinished product is obtained by filtration.Yellow semifinished product solid is sequentially with methanol, ethyl acetate and acetone
It rinses, to obtain white powder o-4Cbz (3.98g, 97%).m.p.>400℃；1H NMR(400MHz,CD2Cl2):d 8.37
(s, 2H), 7.88 (d, J=7.2,8H), 7.45 (d, J=7.72,8H), 7.18-7.10 (m, 16H)；13C NMR(100MHz,
CD2Cl2):d 140.23,135.12,135.28,126.36,124.27,121.07,120.66,110.38；HRMS C54H35N4
(M+) calculated value 739.2862, observed value 739.2833.Anal.C54H34N4Calculated value: C, 87.78；H,4.64；N,7.58；Hair
Present worth C, 87.69；H,4.64；N,7.57..
Embodiment 5: the synthesis of chemical formula (5) compound o-4CbzBz
(i): 2- aminodiphenylamine, triethylamine (TEA) and methylene chloride
(ii): acetic acid reflux
(iii): Cbz, cesium carbonate (Cs2CO3) and 160 DEG C under argon gas of dimethyl sulfoxide
2,3,5,6- phenyl tetrafluoride formyl chloride (2.83g；It 13.34mmol) is dissolved in methylene chloride (35mL), and is added slowly to
Dissolved with triethylamine (3.7mL) and 2- aminodiphenylamine (2.70g；In methylene chloride (35mL) solution 14.67mmol), persistently stir
Mix reaction 12 hours.Mixture is rinsed with water (70mL*1)/1N hydrochloric acid (70mL*2).Organic layer is dry and dense with anhydrous magnesium sulfate
Contracting obtains crude intermediate product, then is flowed back 24 hours with acetic acid (70mL) and carry out cyclodehydration.Later, it is removed with vacuum distillation molten
Agent obtains semifinished product.Semifinished product is again dissolved in methylene chloride, and with 1M K2CO3(aq) (100mL*2) is cleaned.It collects organic
Layer simultaneously, concentration dry with anhydrous magnesium sulfate, then with methylene chloride/Hex recrystallization purifying, obtain 4 (3.73g of colourless product；Yield
81%).m.p.153-154℃；1H NMR(400MHz,d-DMSO):d 8.15-8.06(m,1H),7.90-7.88(m,1H),
7.57-7.48(m,3H),7.41-7.39(m,5H)；13C NMR(100MHz,d-DMSO):d 146.51(m),145.07(m),
144.11(m),142.66,139.63,135.51,134.55,129.97,129.08,126.03,124.57,123.30,
120.06,110.83,109.47(m)；HRMS C19H11F4N2(M+) calculated value 343.3046, observed value
343.0864Anal.C19H10F4N2Calculated value: C, 66.67；H,2.94；N,8.18；Discovery value C, 66.59；H,2.95；N,
8.18。
Then, by cesium carbonate (13.65g under argon system；41.90mmol), carbazole (4.80g；28.70mmol) and nothing
4 (2.38g of color product；6.95mmol) it is blended in dimethyl sulfoxide (17.5mL；160 DEG C 0.4M) are heated to react 48 hours.It
Afterwards, mixture filters to obtain yellow raw product with water (350mL) dilution.Solubility of the yellow raw product for any solvent
It is very poor, then white powder o-4CbzBz (5.85g is sequentially obtained with ethyl acetate, methanol and acetone rinsing；90%).Using it
Before, chemical formula (5) o-4CbzBz distils twice under hot evaporation and film forming condition.m.p.>400℃；1H NMR(500MHz,
CD2Cl2): d 8.28 (s, 1H), 8.02 (d, J=8.25,2H), 7.82 (d, J=7.05,2H), 7.73 (d, J=8.15,2H),
7.68-7.65 (m, 4H), 7.51 (d, J=7.3,2H), 7.45 (t, J=7.10,2H), 7.38 (t, J=7.12,2H), 7.21-
7.17 (m, 3H), 7.09 (t, J=7.3,2H), 7.01-6.99 (m, 3H), 6.92-6.88 (m, 5H), 6.83 (t, J=4.07,
1H), 6.75-6.71 (m, 4H), 6.65 (d, J=8.25,2H), 6.60 (d, J=8.05,1H), 6.55-6.51 (m, 4H)；13C
NMR(100MHz,CD2Cl2):d 145.01,142.64,140.98,140.73,139.89,139.85,138.17,137.50,
136.31,135.73,135.18,134.66,129.61,128.65,126.34,125.61,125.57,125.45,124.98,
124.37,124.26,124.08,123.76,123.73,122.69,121.09,120.73,120.71,120.29,119.97,
119.75,119.64,113.49,110.97,110.80,110.73,110.20；HRMS C67H43N6(M+) calculated value
931.3549 observed value 931.3931.Anal.C67H42N6Calculated value: C, 86.43；H,4.55；N,9.03；Discovery value C,
86.39；H,4.52；N,9.02.
Embodiment 6: the synthesis of chemical formula (6) compound o-4CbzOXD
2,3,5,6- phenyl tetrafluoride formyl chloride (1.11g；5.24mmol) with 5- phenyl -1H-TETRAZOLE (0.92g；6.31mmol)
It is reacted 24 hours in pyridine (10mL) at 95 DEG C.When reaction completion, vacuum is utilized to remove pyridine.Semifinished product is with silica gel tubing string
(eluent is methylene chloride) purifying is chromatographed, white solid 5 is obtained.
Then, under argon system, cesium carbonate (13.65g；41.90mmol), carbazole (4.80g；28.70mmol) and it is white
5 (2.04g of color solid；6.95mmol) it is blended in dimethyl sulfoxide (17.5ml；0.4M), 160 DEG C are heated to react 24 hours.Instead
After answering, is diluted with water (350mL) and yellow semifinished product is obtained by filtration.Solubility of the yellow semifinished product solid for any solvent
It is extremely low.Yellow semifinished product solid sequentially with ethyl acetate, methanol and acetone rinsing, obtains white powder o-4CbzOXD again.It is using
Before, o-4CbzOXD distils twice under hot evaporation and film forming condition.
Embodiment 7: the synthesis of chemical formula (7) compound o-4CbzTAZ
Under argon system, by aniline (1.10mL；12.0mmol) and alchlor (0.40g；3.00mmol) at 140 DEG C
It is stirred to react 2~2.5 hours.The white solid 5 that N-Methyl pyrrolidone (1mL) will be dissolved in is added in aforementioned mixture, 200
It is heated 7~10 hours at DEG C.Reaction mixture is poured into ice water, sediment is collected and is made it dry.During first time
Conversion is not complete, therefore crude mixture reacts primary again.Collect crude product and after second of process with methylene chloride and second
Acetoacetic ester carries out recrystallization purifying and obtains product 6.
Then, under argon system, cesium carbonate (13.65g；41.90mmol), carbazole (4.80g；28.70mmol) and produce
6 (2.56g of object；6.95mmol) it is blended in dimethyl sulfoxide (17.5ml；0.4M), 160 DEG C are heated to react 24 hours.React it
Afterwards, it is diluted with water (350mL) and yellow semifinished product is obtained by filtration.Solubility pole of the yellow semifinished product solid for any solvent
It is low.Yellow semifinished product solid sequentially with ethyl acetate, methanol and acetone rinsing, obtains white powder o-4CbzTAZ again.Using it
Before, o-4CbzTAZ distils twice under hot evaporation and film forming condition.
The evaluation method of material of main part
Material of main part include synthesized according to above-described embodiment 1, embodiment 4 and embodiment 5 compound (i.e. chemical formula (1),
Chemical formula (4) and chemical formula (5)).Evaluation method for material of main part is that the compound of above-described embodiment is carried out three respectively
Weight state energy gap (ET), glass transition temperature (Tg), thermal cracking temperature (Td), highest occupied molecular orbital energy gap (HOMO) and
The measurement of lowest unoccupied molecular orbital energy gap (LUMO).Triplet energy gap can be measured at low temperature with spectrometer, be yes
The main foundation of the no material of main part for doing phosphorescent emitter, for blue light organic emissive diode, common phosphorescence shines
Body is FIrpic (ET=2.65eV), its E of the host emitter developedT2.65eV is had to be larger than, is just avoided that energy returns
And luminous efficiency is caused to reduce.Glass transition temperature and ardent solution temperature are by differential scanning calorimetry (DSC) respectively
(differential scanning calorimeter, DSC) and thermogravimetric analyzer (thermogravimetric
Analyzer, TGA) measured, be that element production the most is upper and performance on whether foundation that can be stable.And HOMO and LUMO points
It is not distinctly to scan its oxidizing potential and reduction potential using cyclic voltammetry and obtain, the electricity that energy gap difference is small therewith is looked for benefit
Lotus injection material makes element have biggish efficiency.Compound (chemical formula (1) o-3CbzBz, chemical formula (4) o-4Cbz and chemistry
Formula (5) o-4CbzBz) property arrange such as table one.
Table one:
As shown in Table 1, chemical formula (1) o-3CbzBz, chemical formula (4) o-4Cbz and chemical formula (5) o-4CbzBz thermal cracking
Temperature is at 350 DEG C or more, this is because its structure contains more benzene ring structures.Phenyl ring belongs to rigid structure, therefore in heating
In the process, thermal cracking will not be generated because of high temperature.Based on the above results, this analog derivative can have good thermal stability with
High triplet energy gap, therefore the material of main part in the considerably advantageous organic luminous layer in as Organic Light Emitting Diode.
TgFor another index of judgment component stability, TgHigh material has good performance on element stability.
As can be seen from Table I, compared to commercially available material TCP (Tg: 125 DEG C), o-3CbzBz is in thermal property TgPerformance on be better than TCP,
Confirm that introducing benzimidazole group facilitates the improvement of thermal property.In addition to this, o-4Cbz and o-4CbzBz are not observed
TgPoint is to be unable to reach its fusing point (T due to being limited the heating temperature of testing machinesgGreater than 400 DEG C), molecule can not be melted and be reached
To amorphous state and then T can not be measuredg。
Compound (chemical formula (1), chemical formula (4) and chemical formula (5)) is as material of main part in Organic Light Emitting Diode member
Efficiency performance in part
Element architecture is ITO/TAPC (50nm)/mCP (10nm)/main body (host): emitter (emitter) (30nm)/
DPPS(30nm)/LiF(0.9nm)/Al(120nm).The material of main part of organic luminous layer is then with chemical formula (1), chemical formula (4)
It is used as material of main part with chemical formula (5), and the emitter (FIrpic) for different doping ratios of arranging in pairs or groups is used as guest materials.Here,
The material of the first electrode layer of organic light-emitting diode element is ITO.The material of the second electrode lay is aluminium, with a thickness of 120nm.It is empty
The material of cave transport layer is TAPC, with a thickness of 50nm.Organic luminous layer with a thickness of 30nm.The material of electronic barrier layer is mCP,
With a thickness of 10nm.The material of electron transfer layer is DPPS, with a thickness of 30nm.The material of electron injecting layer is LiF, with a thickness of
0.9nm.Above-mentioned each film layer is formed by vapor deposition and completes the Organnic electroluminescent device of the present embodiment, and is evaluated respectively according to institute
Organic light-emitting diode element obtained is in 1cd/m2Driving voltage, maximum current efficiency CE (cd/A), maximum power efficiency
PE (lm/W) and maximum external quantum efficiency (External quantum efficiency, EQE) (%).Evaluation result column
In the following table 2.
Table 2:
A.FIrpic blends concentration
Organic light-emitting diode element in table 2 not only has low driving voltage, also has good current efficiency, function
Rate efficiency and external quantum efficiency.It follows that material of main part of the invention has high electronics and hole transport rate,
Not needing high driving voltage can be operated.It is noted that the external quantum efficiency in table 2 is also high, it follows that this hair
Bright material of main part triplet energy gap with higher, and facilitate the phenomenon that reducing energy passback, and then Organic Electricity can be increased
The luminous efficiency of electroluminescent devices.
Compound (chemical formula (4)) and mCP are showed as efficiency of the hole transmission layer in organic light-emitting diode element
Compare
Element architecture is ITO/TAPC (500nm)/o-4Cbz (50~200nm)/main body: emitter (300nm:15%)/
DPPS(500nm)/LiF/Al.The material of main part of organic luminous layer is then using chemical formula (5) as material of main part.Here, organic
The material of the first electrode layer of light-emitting diode is ITO.The material of the second electrode lay is aluminium, with a thickness of 120nm.First is empty
The material of cave transport layer is TAPC, with a thickness of 500nm.The material of second hole transmission layer is the o- with a thickness of 50~200nm
4Cbz or mCP.Organic luminous layer with a thickness of 300nm.The material of electron transfer layer is DPPS, with a thickness of 500nm.Electron injection
The material of layer is LiF, with a thickness of 0.9nm.By the way that the organic electroluminescent for forming above-mentioned each film layer and completing the present embodiment is deposited
Device, and evaluate every efficiency of element.Evaluation result is listed in the table below 3 and table 4.
Table 3:
Table 4:
It is maximum using material o-4CbzBz as the fertile material of FIrpic and the mCP that arranges in pairs or groups is as the second hole transmission layer
Current efficiency is up to 62.55cd/A, and maximum external quantum efficiency is up to 30.59%.And works as and passed using o-4Cbz as the second hole
When defeated layer, 64.09cd/A can be promoted in maximum current efficiency, maximum power efficiency is up to 66.3lm/W, and outside maximum
Efficiency of element can be improved up to 30.91%, when it may thus be appreciated that o-4Cbz is as hole transmission layer in the performance of quantum efficiency.
From the above, carbazole derivates material of the invention and organic light-emitting diode element are with 1,3,5- tri- (click
Azoles -9- base) benzene (TCP) or 1,2,4,5- tetra- (9H- carbazole -9- base) benzene (o-4Cbz) are used as core, and can be respectively at ortho position
Different types of subbase group that conducts electricity is connected, the quadripole of the phosphorescence Organic Light Emitting Diode of high efficiency and good thermal stability is formed
Host emitter.In addition, carbazole derivates material of the invention can also be used for hole transmission layer.Furthermore 1,2,4,5- tetra- (9H- click
Azoles -9- base) benzene (o-4Cbz) itself also can be used as host emitter material and hole transport layer material.
The foregoing is merely illustratives, and not restrictive.It is any without departing from spirit and scope of the invention, and to it
The equivalent modifications or change of progress, should be included in the attached claims.
Claims (20)
1. a kind of carbazole derivates material, the structure with general formula (1):
Wherein R1Selected from one of general formula (2), general formula (3) and structure of general formula (4),
Wherein, R2To R41With R80To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy, alkyl halide
One of base, sulfanyl, silicyl and alkenyl.
2. carbazole derivates material as described in claim 1, wherein alkyl is the substituted straight chained alkyl of carbon number 1~6, does not take
The straight chained alkyl in generation, the substituted branched alkyl of carbon number 3~6, carbon number 3~6 the branched alkyl not replaced, naphthenic base is carbon number
3~6 substituted naphthenic base, the naphthenic base of carbon number 3~6 not replaced, alkoxy are the substituted straight chain alcoxyl of carbon number 1~6
Base, the unbranched alkoxy of carbon number 1~6 not replaced, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 do not replace
Branched alkoxy, alkylhalide group are the straight chain alkylhalide group, the carbon that do not replace of the substituted straight chain alkylhalide group of carbon number 1~6, carbon number 1~6
The branch alkylhalide group of the substituted branch alkylhalide group of number 3~6, carbon number 3~6 not replaced, sulfanyl are the substitution of carbon number 1~6
Straight chain sulfanyl, the straight chain sulfanyl not replaced of carbon number 1~6, carbon number 3~6 substituted branch sulfanyl, carbon number 3~6
The branch sulfanyl not replaced, silylation be the substituted straight chain silylation of carbon number 1~6, carbon number 1~6 do not replace it is straight
Chain silane base, the substituted branch silylation of carbon number 3~6, carbon number 3~6 the branch silylation not replaced, alkenyl be carbon number 2
~6 substituted straight-chain alkenyl, the straight-chain alkenyl of carbon number 2~6 not replaced, carbon number 3~6 substituted branched-chain alkenyl or carbon number
3~6 branched-chain alkenyl not replaced.
3. a kind of carbazole derivates material, the structure with general formula (5):
Wherein R46Selected from general formula (2), general formula (3), general formula (4), hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alcoxyl
One of base, alkylhalide group, sulfanyl, silylation and alkenyl,
Wherein, R28To R41And R47To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy, alkyl halide
One of base, sulfanyl, silicyl and alkenyl.
4. carbazole derivates material as claimed in claim 3, wherein alkyl is the substituted straight chained alkyl of carbon number 1~6, does not take
The straight chained alkyl in generation, the substituted branched alkyl of carbon number 3~6, carbon number 3~6 the branched alkyl not replaced, naphthenic base is carbon number
3~6 substituted naphthenic base, the naphthenic base of carbon number 3~6 not replaced, alkoxy are the substituted straight chain alcoxyl of carbon number 1~6
Base, the unbranched alkoxy of carbon number 1~6 not replaced, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 do not replace
Branched alkoxy, alkylhalide group are the straight chain alkylhalide group, the carbon that do not replace of the substituted straight chain alkylhalide group of carbon number 1~6, carbon number 1~6
The branch alkylhalide group of the substituted branch alkylhalide group of number 3~6, carbon number 3~6 not replaced, sulfanyl are the substitution of carbon number 1~6
Straight chain sulfanyl, the straight chain sulfanyl not replaced of carbon number 1~6, carbon number 3~6 substituted branch sulfanyl, carbon number 3~6
The branch sulfanyl not replaced, silylation be the substituted straight chain silylation of carbon number 1~6, carbon number 1~6 do not replace it is straight
Chain silane base, the substituted branch silylation of carbon number 3~6, carbon number 3~6 the branch silylation not replaced, alkenyl be carbon number 2
~6 substituted straight-chain alkenyl, the straight-chain alkenyl of carbon number 2~6 not replaced, carbon number 3~6 substituted branched-chain alkenyl or carbon number
3~6 branched-chain alkenyl not replaced.
5. a kind of organic light-emitting diode element, comprising:
First electrode layer；
The second electrode lay；And
Organic light-emitting units are configured between the first electrode layer and the second electrode lay, the organic light-emitting units packet
Containing the carbazole derivates material as shown in general formula (1),
Wherein R1Selected from one of general formula (2), general formula (3) and structure of general formula (4),
Wherein, R2To R41With R80To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy, alkyl halide
One of base, sulfanyl, silicyl and alkenyl.
6. organic light-emitting diode element as claimed in claim 5, wherein alkyl be carbon number 1~6 substituted straight chained alkyl,
The branched alkyl of the substituted branched alkyl of the straight chained alkyl, carbon number 3~6 that do not replace, carbon number 3~6 not replaced, naphthenic base are
Substituted naphthenic base, the naphthenic base of carbon number 3~6 not replaced of carbon number 3~6, alkoxy are the substituted straight chain of carbon number 1~6
Alkoxy, the unbranched alkoxy of carbon number 1~6 not replaced, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6 do not take
The branched alkoxy in generation, alkylhalide group are the straight chain alkyl halide of the substituted straight chain alkylhalide group of carbon number 1~6, carbon number 1~6 not replaced
Base, the substituted branch alkylhalide group of carbon number 3~6, carbon number 3~6 the branch alkylhalide group not replaced, sulfanyl is carbon number 1~6
Substituted branch sulfanyl, the carbon number of the straight chain sulfanyl not replaced of substituted straight chain sulfanyl, carbon number 1~6, carbon number 3~6
3~6 branch sulfanyl not replaced, silylation are that the substituted straight chain silylation of carbon number 1~6, carbon number 1~6 do not replace
Straight chain silylation, the substituted branch silylation of carbon number 3~6, carbon number 3~6 the branch silylation not replaced, alkenyl is carbon
The substituted straight-chain alkenyl of number 2~6, the straight-chain alkenyl of carbon number 2~6 not replaced, carbon number 3~6 substituted branched-chain alkenyl or
The branched-chain alkenyl of carbon number 3~6 not replaced.
7. organic light-emitting diode element as claimed in claim 5, wherein the organic light-emitting units include organic luminous layer.
8. organic light-emitting diode element as claimed in claim 7, wherein the organic light-emitting units further include hole transport
Layer and electron transfer layer, wherein the organic luminous layer is configured between the hole transmission layer and the electron transfer layer.
9. organic light-emitting diode element as claimed in claim 7, wherein the organic light-emitting units further include hole transport
Layer, electronic barrier layer, electron transfer layer and electron injecting layer, wherein the hole transmission layer between the electron injecting layer according to
Sequence configures the electronic barrier layer, the organic luminous layer and the electron transfer layer.
10. organic light-emitting diode element as claimed in claim 7, wherein the organic luminous layer includes material of main part and visitor
Body material, the material of main part are the carbazole derivates material, and the guest materials is phosphorescent light-emitting materials.
11. organic light-emitting diode element as claimed in claim 10, wherein the material of main part is in the organic luminous layer
Content between 60 volume % between 95 volume %.
12. organic light-emitting diode element as claimed in claim 10, wherein the guest materials is in the organic luminous layer
Content between 5 volume % between 40 volume %.
13. a kind of organic light-emitting diode element, comprising:
First electrode layer；
The second electrode lay；And
Organic light-emitting units are configured between the first electrode layer and the second electrode lay, the organic light-emitting units packet
Containing the carbazole derivates material one of as shown in general formula (5),
Wherein R46Selected from general formula (2), general formula (3), general formula (4), hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alcoxyl
One of base, alkylhalide group, sulfanyl, silylation and alkenyl,
Wherein, R28To R41And R47To R89Independently selected from hydrogen atom, fluorine atom, cyano, alkyl, naphthenic base, alkoxy, alkyl halide
One of base, sulfanyl, silicyl and alkenyl.
14. organic light-emitting diode element as claimed in claim 13, wherein alkyl is the substituted straight chain alkane of carbon number 1~6
Base, the straight chained alkyl not replaced, the substituted branched alkyl of carbon number 3~6, carbon number 3~6 the branched alkyl not replaced, cycloalkanes
Base is substituted naphthenic base, the naphthenic base of carbon number 3~6 not replaced of carbon number 3~6, and alkoxy is the substituted of carbon number 1~6
Unbranched alkoxy, the unbranched alkoxy of carbon number 1~6 not replaced, the substituted branched alkoxy of carbon number 3~6, carbon number 3~6
The branched alkoxy not replaced, alkylhalide group are the straight chain of the substituted straight chain alkylhalide group of carbon number 1~6, carbon number 1~6 not replaced
Alkylhalide group, the substituted branch alkylhalide group of carbon number 3~6, carbon number 3~6 the branch alkylhalide group not replaced, sulfanyl be carbon number 1
~6 substituted straight chain sulfanyl, the straight chain sulfanyl of carbon number 1~6 not replaced, carbon number 3~6 substituted branch sulfane
The branch sulfanyl of base, carbon number 3~6 not replaced, silylation are the substituted straight chain silylation of carbon number 1~6, carbon number 1~6
The branch silylation of the substituted branch silylation of the straight chain silylation, carbon number 3~6 that do not replace, carbon number 3~6 not replaced, alkene
Base is the substituted branch of the substituted straight-chain alkenyl of carbon number 2~6, the straight-chain alkenyl of carbon number 2~6 not replaced, carbon number 3~6
The branched-chain alkenyl of alkenyl or carbon number 3~6 not replaced.
15. organic light-emitting diode element as claimed in claim 13, wherein the organic light-emitting units include organic light emission
Layer.
16. organic light-emitting diode element as claimed in claim 15, wherein the organic light-emitting units further include that hole passes
Defeated layer and electron transfer layer, wherein the organic luminous layer is configured between the hole transmission layer and the electron transfer layer.
17. organic light-emitting diode element as claimed in claim 15, wherein the organic light-emitting units further include that hole passes
Defeated layer, electronic barrier layer, electron transfer layer and electron injecting layer, wherein the hole transmission layer is between the electron injecting layer
Sequentially configure the electronic barrier layer, the organic luminous layer and the electron transfer layer.
18. organic light-emitting diode element as claimed in claim 15, wherein the organic luminous layer include material of main part and
Guest materials, the material of main part are the carbazole derivates material, and the guest materials is phosphorescent light-emitting materials.
19. organic light-emitting diode element as claimed in claim 18, wherein the material of main part is in the organic luminous layer
Content between 60 volume % between 95 volume %.
20. organic light-emitting diode element as claimed in claim 18, wherein the guest materials is in the organic luminous layer
Content between 5 volume % between 40 volume %.
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