CN103965441B - A kind of organic semiconducting materials - Google Patents
A kind of organic semiconducting materials Download PDFInfo
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- CN103965441B CN103965441B CN201310038369.7A CN201310038369A CN103965441B CN 103965441 B CN103965441 B CN 103965441B CN 201310038369 A CN201310038369 A CN 201310038369A CN 103965441 B CN103965441 B CN 103965441B
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- semiconducting materials
- organic semiconducting
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- palladium
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 73
- 239000000126 substance Substances 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 abstract description 65
- 238000000034 method Methods 0.000 abstract description 9
- 230000005540 biological transmission Effects 0.000 abstract description 8
- 230000008569 process Effects 0.000 abstract description 8
- 238000004020 luminiscence type Methods 0.000 abstract description 4
- 230000005525 hole transport Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000007423 decrease Effects 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 229910052757 nitrogen Inorganic materials 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
- 239000010410 layer Substances 0.000 description 23
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 229910052763 palladium Inorganic materials 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- -1 4,6-difluorophenyl Chemical group 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 238000000862 absorption spectrum Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 229910052741 iridium Inorganic materials 0.000 description 8
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
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- 241001062009 Indigofera Species 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C)(*)C(C)(C)OCCc(cc1)ccc1N(c1ccc(BOC(C)(C)C(C)(C)O)cc1)c(cc1)ccc1O* Chemical compound CC(C)(*)C(C)(C)OCCc(cc1)ccc1N(c1ccc(BOC(C)(C)C(C)(C)O)cc1)c(cc1)ccc1O* 0.000 description 2
- QBBOCSNLIYAOFH-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)C1=CC=CC=C1.[P] Chemical group COC1=C(C(=CC=C1)OC)C1=CC=CC=C1.[P] QBBOCSNLIYAOFH-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- JYMITAMFTJDTAE-UHFFFAOYSA-N aluminum zinc oxygen(2-) Chemical compound [O-2].[Al+3].[Zn+2] JYMITAMFTJDTAE-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229940094933 n-dodecane Drugs 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- DADZIMNFQANSAN-UHFFFAOYSA-N C(C1=CC=CC=C1)CC(C)=O.[Ar] Chemical compound C(C1=CC=CC=C1)CC(C)=O.[Ar] DADZIMNFQANSAN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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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
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- H10K85/151—Copolymers
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
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- C—CHEMISTRY; METALLURGY
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
- C08G2261/3162—Arylamines
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/411—Suzuki reactions
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
- C08G2261/512—Hole transport
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- C08G2261/50—Physical properties
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- C08G2261/514—Electron transport
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/52—Luminescence
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a kind of organic semiconducting materials, the chemical formula of described organic semiconducting materials is as follows:Wherein, R is C1~C20Alkyl, n is the integer of 10 ~ 100, the present invention provides organic semiconducting materials to have hole transport character and electronic transport property simultaneously, the transmission making this organic semiconducting materials hole and electronics in luminescent layer balances, also there is higher triplet, triplet is more than 2.75eV, effectively prevents energy in luminescence process from returning to material of main part, is greatly improved luminous efficiency.This organic semiconducting materials have employed better simply synthetic route, decreases technological process, and raw material is cheap and easy to get, and manufacturing cost is reduced.
Description
Technical field
The invention belongs to field of photovoltaic materials, be specifically related to a kind of organic semiconducting materials.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view width and can be tied by chemistry
Structure fine setting changes luminescent properties makes rich color, easily realizes the advantages such as resolution is high, lightweight, large-area flat-plate shows, quilt
It is described as " 21 century flat panel display ", becomes subject and the focuses of flat pannel display area research such as material, information, physics.Not
Carry out efficient commercialization Organic Light Emitting Diode will be likely to containing organic metal phosphor, because they can be by singletstate
All capture with triplet excitons, thus realize the internal quantum efficiency of 100%.But, due to the excited state of transient metal complex
Exciton lifetime is the most long, causes unwanted triplet state-triplet state (T1-T1) cancellation in device real work.In order to overcome
This problem, triplet emission thing is often doped in organic host material by researchers.
In recent years, green and red phosphorescent OLED shows gratifying electroluminescent efficiency.And it is blue efficiently
Color phosphorescent devices is little, and main cause is a lack of having preferable carrier transmission performance and higher triplet simultaneously
(ET) material of main part.
Summary of the invention
For solving the problems referred to above, the invention provides a kind of organic semiconducting materials, this organic semiconducting materials has sky
Cave transport property and electronic transport property, make the transmission of this semi-conducting material hole and electronics in luminescent layer balance, also have
Higher triplet, triplet is more than 2.75eV, effectively prevents energy in luminescence process from returning to material of main part,
Being greatly improved luminous efficiency, organic semiconducting materials of the present invention is that bipolarity blue emitting phosphor material of main part provides new may select
Kind.Present invention also offers the preparation method of this organic semiconducting materials, and comprise the electricity of this organic semiconducting materials
Electroluminescence device.
On the one hand, the invention provides a kind of organic semiconducting materials, the chemical formula of described organic semiconducting materials is as follows
Shown in:
Wherein, R is C1～C20Alkyl, n be 10～100 whole
Number.
Second aspect, the invention provides the preparation method of a kind of organic semiconducting materials, comprises the steps:
Offer compound A:With compound B:
Wherein, R is C1～C20Alkyl；Under an inert atmosphere, it is 1: 1～1: 1.2 to add compound A and compound B according to mol ratio
Add in the organic solvent containing catalyst and aqueous slkali, at 70～130 DEG C, carry out Suzuki coupled reaction 12～96 hours,
Described catalyst is organic palladium or the mixture for organic palladium and organophosphor ligand, and obtain that following structural formula represents organic partly leads
Body material P:
Wherein, n is the integer of 10～100.
Preferably, the preparation method of described organic semiconducting materials also includes carrying out organic semiconducting materials P separating pure
The step changed, described purification procedures is as follows: molten after described compound A and compound B carries out Suzuki coupled reaction
Liquid adds methanol precipitating and filters, the solid being filtrated to get is stripped with methanol and normal hexane successively, will be through extracting
After solid chloroform, collect and evaporate solvent after chloroformic solution and obtain organic semiconducting materials P after purification.
Preferably, at least one in toluene, DMF, oxolane of described organic solvent.
Preferably, at least one in sodium carbonate liquor, solution of potassium carbonate and sodium bicarbonate solution of described aqueous slkali,
Solute in described aqueous slkali is 20: 1～50: 1 with the mol ratio of compound A.
Preferably, described organic palladium is bis-triphenylphosphipalladium palladium dichloride, tetra-triphenylphosphine palladium, palladium or three dibenzylidenes
Acetone two palladium, described organophosphorus ligand is tri-butyl phosphine, tri-o-tolyl phosphine or 2-dicyclohexyl phosphorus-2 ', 6 '-dimethoxy
Biphenyl, described organic palladium is 1: 4～1: 8 with the mol ratio of described organophosphorus ligand.
Preferably, the organic palladium in described catalyst is 1: 20～1: 100 with the mol ratio of described compound A.
The third aspect, the invention provides a kind of electroluminescent device, including the substrate with anode stacked gradually, sends out
Photosphere and cathode layer, described luminescent layer is the mixture of material of main part and guest materials, and wherein material of main part is as follows
Organic semiconducting materials:Wherein, R is C1～C20Alkyl, n is 10～100
Integer, guest materials be three [1-phenyl isoquinolin quinoline-C2, N] iridium, double (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic close
Iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] close iridium or [two (2 ', 4 '-difluorophenyl) pyridine]
(tetrazolium pyridine) closes iridium.
Preferably, described material of main part is 5%～15% with the mass percent of described guest materials.
Preferably, anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
The invention provides a kind of organic semiconducting materials, preparation method and electroluminescent device, there is following useful effect
Really: there is hole transport character and electronic transport property simultaneously, organic semiconducting materials hole and electronics in luminescent layer are made
Transmission balance, also has higher triplet, and triplet is more than 2.75eV, effectively prevents energy in luminescence process
Return to material of main part, be greatly improved luminous efficiency.This material have employed better simply synthetic route, decreases technological process,
Raw material is cheap and easy to get, and manufacturing cost is reduced.
Accompanying drawing explanation
Fig. 1 is the organic electroluminescence device that the organic semiconducting materials prepared in embodiment 1 prepares for material of main part
Structural representation；
Fig. 2 is the thermogravimetic analysis (TGA) figure of the organic semiconducting materials prepared in embodiment 1.
Detailed description of the invention
In order to be more fully understood that the content of patent of the present invention, further illustrate this below by concrete example and legend
The technology case of invention, specifically includes material preparation and prepared by device, but these embodiments are not limiting as the present invention, wherein monomer
A commercially obtains, method disclosed in monomer B reference literature (J.AM.CHEM.SOC.9VOL.125, NO.44,2003)
Synthesis obtains.
The invention provides a kind of organic semiconducting materials, the chemical formula of described organic semiconducting materials is as follows:
Wherein, R is C1～C20Alkyl, n is the integer of 10～100.
This organic semiconducting materials has bipolarity carrier transport ability, makes the hole in luminescent layer and electric transmission
Balance；There is hole transport character and electronic transport property simultaneously, make this organic semiconducting materials hole and electricity in luminescent layer
The transmission balance of son, also has higher triplet, and triplet is more than 2.75eV, effectively prevents in luminescence process
Energy returns to material of main part, is greatly improved luminous efficiency, and organic semiconducting materials the most of the present invention has bipolarity blue light phosphorus
Light material of main part.
The invention provides the preparation method of a kind of organic semiconducting materials, comprise the steps:
Offer compound A:With compound B:
Wherein, R is C1～C20Alkyl；Under an inert atmosphere, it is 1: 1～1: 1.2 to add compound A and compound B according to mol ratio
Add in the organic solvent containing catalyst and aqueous slkali, at 70～130 DEG C, carry out Suzuki coupled reaction 12～96 hours,
Described catalyst is organic palladium or the mixture for organic palladium and organophosphor ligand, and obtain that following structural formula represents organic partly leads
Body material P:
Wherein, n is the integer of 10～100.
In a particular embodiment, the preparation method of described organic semiconducting materials further comprises organic semiconductor material
Material P carries out isolated and purified step, and described purification procedures is as follows: carry out Suzuki coupling to described compound A and compound B
Close and reacted solution adds methanol precipitating and filters, the solid being filtrated to get is taken out with methanol and normal hexane successively
Carry, by the solid chloroform after extracting, evaporate solvent after collecting chloroformic solution and obtain organic semiconductor after purification
Material P.
In present embodiment, extracting uses apparatus,Soxhlet's to carry out.
In present embodiment, evaporate solvent after chloroformic solution being collected and obtain organic semiconducting materials P after purification very
Empty lower 50 DEG C～70 DEG C are dried 24 hours～48 hours.
In a particular embodiment, during described organic solvent is selected from toluene, DMF, oxolane at least
A kind of.
In a particular embodiment, described aqueous slkali is in sodium carbonate liquor, solution of potassium carbonate and sodium bicarbonate solution
At least one, the solute in described aqueous slkali is 20: 1～50: 1 with the mol ratio of compound A.
In a particular embodiment, described organic palladium is bis-triphenylphosphipalladium palladium dichloride, tetra-triphenylphosphine palladium, palladium or three
Dibenzalacetone two palladium, described organophosphorus ligand is tri-butyl phosphine, tri-o-tolyl phosphine or 2-dicyclohexyl phosphorus-2 ', 6 '-
Dimethoxy-biphenyl, described organic palladium is 1: 4～1: 8 with the mol ratio of described organophosphorus ligand.
In a particular embodiment, the organic palladium in described catalyst is 1: 20～1 with the mol ratio of described compound A:
100。
Have employed better simply synthetic route, thus reduce technological process, raw material is cheap and easy to get so that manufacturing cost drops
Low.
The invention provides a kind of electroluminescent device, including stack gradually have the substrate of anode, luminescent layer and
Cathode layer, described luminescent layer is the mixture of material of main part and guest materials, and wherein as follows organic of material of main part partly leads
Body material:Wherein, R is C1～C20Alkyl, n is the integer of 10～100, visitor
Body material be three [1-phenyl isoquinolin quinoline-C2, N] iridium, double (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic close iridium, [two (2 ',
4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] closes iridium or [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) closes
Iridium.
In a particular embodiment, described guest materials is 5%～15% with the mass percent of described material of main part.
In a particular embodiment, anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
Organic luminescent device based on this material launches blue light, and luminous efficiency is high.
Embodiment 1:
Present embodiment discloses poly-{ 4-normal hexane oxygen-N, N-bis-(4-base-phenyl) aniline-co-3,7-that structural formula is following
Diyl sulfur dibenzofuran } (organic semiconducting materials P1):
The preparation process of above-mentioned organic semiconducting materials P1 is as follows:
Under argon shield, by 4-normal hexane oxygen-N, N-bis-(4-pinacol borate phenyl) aniline (119mg,
0.2mmol), 3,7-dibromo sulfur dibenzofuran (75mg, 0.2mmol) adds and fills in the flask of 10ml toluene solvant, after fully dissolving
Joining in flask by potassium carbonate (2mL, 2mol/L) solution, evacuation deoxygenation is also filled with argon, is subsequently adding bi triphenyl phosphine
Palladium chloride (5.6mg, 0.008mmol)；Flask is heated to 100 DEG C and carries out Suzuki coupled reaction 48h.Stop poly-after cooling
Close reaction, drip in 50ml methanol in flask and settle；Successively with methanol and just own after being filtered by apparatus,Soxhlet's
Alkane extracting 24h.Then with chloroform for solvent extraction to colourless, collect chloroformic solution and be spin-dried for obtaining red powder, obtaining this and gather
{ 4-normal hexane oxygen-N, N-bis-(4-base-phenyl) aniline-co-3,7-diyl sulfur dibenzofuran } organic semiconducting materials, under last vacuum
50 DEG C of dry 24h.Productivity is 83%.
The above-mentioned reaction equation preparing organic semiconducting materials P1 is as follows:
Molecule measuring test result is: Molecular weight (GPC, THF, R.I): Mn=32.7kDa, Mw/Mn=2.2.
See the thermogravimetic analysis (TGA) figure that accompanying drawing 2 is organic semiconducting materials prepared by the present embodiment, thermogravimetric curve (TGA)
Test is carried out on TA SDT 2960 instruments, and under nitrogen air-flow protection, programming rate is 10K/min.Permissible by figure
Find out that the thermal weight loss temperature of 5% is 403 DEG C.
The uv-visible absorption spectra figure of the organic semiconducting materials P1 of preparation, ultraviolet-ray visible absorbing light in embodiment 1
Spectrum is measured on Jasco-570 uv analyzer.As seen from the figure: having between 300nm～800nm of Inventive polymers
Absorption wider relatively greatly, wherein maximum absorption band is positioned at 582nm, and wide absorption spectrum shows that P1 is a kind of photovoltaic material.
By test antenna effect spectrum, instrument is FS modular fluorometer/pectrophosphorimeter, makes to investigate in embodiment 1
Standby organic semiconducting materials P1 triplet emission characteristic.Under the liquid nitrogen of 77K, organic semiconducting materials P1 shows the strongest
Phosphorescent emissions, emission peak is at 446nm, and corresponding triplet energy state is 2.78eV, is much higher than double (4, the 6-difluorobenzenes of phosphor material
Yl pyridines-N, C2) pyridinecarboxylic close iridium (III) FIrpic triplet energy state (2.65eV), test data result show us
Material can be as blue emitting phosphor material of main part.
Embodiment 2:
Present embodiment discloses poly-{ 4-methane epoxide-N, N-bis-(4-base-phenyl) aniline-co-3,7-that structural formula is following
Diyl sulfur dibenzofuran } (organic semiconducting materials P2):
Under nitrogen and argon gaseous mixture are protected, by 4-methane oxygen-N, N-bis-(4-pinacol borate phenyl) aniline
(158mg, 0.3mmol), 3,7-dibromo sulfur dibenzofuran (112mg, 0.3mmol) and 15mL oxolane add two mouthfuls of 50mL specification
In Ping, after being passed through the gaseous mixture air-discharging about 20min of nitrogen and argon after fully dissolving, then by tetra-triphenylphosphine palladium (4mg,
0.003mmol) it is added thereto, after fully dissolving, adds sodium bicarbonate (3mL, 2mol/L) solution.The most fully lead to nitrogen and argon
After the gaseous mixture air-discharging about 10min of gas, two-mouth bottle is joined 70 DEG C and carries out Suzuki coupled reaction 96h.Stop after cooling
Polyreaction, drips in 40ml methanol in flask and settles；Successively with methanol and just after being filtered by apparatus,Soxhlet's
Hexane extraction 24h.Then with chloroform for solvent extraction to colourless, collect chloroformic solution and be spin-dried for obtaining red powder, being gathered
{ 4-methane epoxide-N, N-bis-(4-base-phenyl) aniline-co-3,7-diyl sulfur dibenzofuran } organic semiconducting materials, under last vacuum
50 DEG C of dry 24h.Productivity is 76%.
The above-mentioned reaction equation preparing organic semiconducting materials P2 is as follows:
Molecule measuring test result is: Molecular weight (GPC, THF, R.I): Mn=45.1kDa, Mw/Mn=2.1.
The thermogravimetic analysis (TGA) figure of the organic semiconducting materials P2 of the present embodiment 2 preparation, thermogravimetric curve (TGA) is tested at TA
Carrying out on SDT 2960 instruments, under nitrogen air-flow protection, programming rate is 10K/min.As seen from the figure 5%
Thermal weight loss temperature is 447 DEG C.
The uv-visible absorption spectra figure of the organic semiconducting materials P2 of preparation, ultraviolet-ray visible absorbing light in embodiment 2
Spectrum is measured on Jasco-570 uv analyzer.As seen from the figure: having between 300nm～800nm of Inventive polymers
Absorption wider relatively greatly, wherein maximum absorption band is positioned at 584nm, and wide absorption spectrum shows that P2 is a kind of photovoltaic material.
By test antenna effect spectrum, instrument is FS modular fluorometer/pectrophosphorimeter, to investigate organic semiconductor material
Material P2 triplet emission characteristic.Under the liquid nitrogen of 77K, organic semiconducting materials P2 shows the strongest phosphorescent emissions, emission peak
At 449nm, corresponding triplet energy state is 2.76eV, is much higher than double (4,6-difluorophenyl pyridinato-N, the C2) pyrrole of phosphor material
Pyridine formyl closes the triplet energy state (2.65eV) of iridium (III) FIrpic, and test data result shows that our material can be as indigo plant
Light phosphorescent light body material.
Embodiment 3:
Present embodiment discloses poly-{ 4-AI3-28404 epoxide-N, N-bis-(4-base-phenyl) aniline-co-that structural formula is following
3,7-diyl sulfur dibenzofuran } (organic semiconducting materials P3):
Under nitrogen protection, by 4-AI3-28404 epoxide-N, N-bis-(4-pinacol borate phenyl) aniline (238mg,
0.3mmol), 3,7-dibromo sulfur dibenzofuran (123mg, 0.33mmol), palladium (3.5mg, 0.015mmol) and three (O-methoxies
Phenyl) phosphine (21mg, 0.06mmol) joins in the flask of the DMF filling 12mL, adds after fully dissolving
Potassium carbonate (3mL, 2mol/L) solution, subsequently toward after nitrogen purge gas about 30min logical in flask；Flask is heated to 130 DEG C enter
Row Suzuki coupled reaction 12h.Stopped reaction is also cooled to room temperature, drips in 40ml methanol and settle in flask；Pass through
Apparatus,Soxhlet's extracts 24h with methanol and normal hexane after filtering successively.Then with chloroform for solvent extraction to colourless, chlorine is collected
Imitative solution also is spin-dried for obtaining red powder, obtains poly-{ 4-AI3-28404 epoxide-N, N-bis-(4-base-phenyl) aniline-co-3,7-
Diyl sulfur dibenzofuran } organic semiconducting materials, the lower 50 DEG C of dry 24h of last vacuum.Productivity is 80%.
The above-mentioned reaction equation preparing organic semiconducting materials P3 is as follows:
Molecule measuring test result is: Molecular weight (GPC, THF, R.I): Mn=75.8kDa, Mw/Mn=2.0.
The thermogravimetic analysis (TGA) figure of the organic semiconducting materials P3 of the present embodiment 3 preparation, thermogravimetric curve (TGA) is tested at TA
Carrying out on SDT 2960 instruments, under nitrogen air-flow protection, programming rate is 10K/min.As seen from the figure 5%
Thermal weight loss temperature is 386 DEG C.
The uv-visible absorption spectra figure of the organic semiconducting materials P3 of preparation, ultraviolet-ray visible absorbing light in embodiment 3
Spectrum is measured on Jasco-570 uv analyzer.As seen from the figure: having between 300nm～800nm of Inventive polymers
Absorption wider relatively greatly, wherein maximum absorption band is positioned at 580nm, and wide absorption spectrum shows that P3 is a kind of photovoltaic material.
By test antenna effect spectrum, instrument is FS modular fluorometer/pectrophosphorimeter, to investigate organic semiconductor material
Material P3 triplet emission characteristic.Under the liquid nitrogen of 77K, organic semiconducting materials P3 shows the strongest phosphorescent emissions, emission peak
At 443nm, corresponding triplet energy state is 2.80eV, is much higher than double (4,6-difluorophenyl pyridinato-N, the C2) pyrrole of phosphor material
Pyridine formyl closes the triplet energy state (2.65eV) of iridium (III) FIrpic, and test data result shows that our material can be as indigo plant
Light phosphorescent light body material.
Embodiment 4:
Present embodiment discloses structural formula following poly-4-normal butane epoxide-N, N-bis-(4-base-phenyl) aniline-co-3,
7-diyl sulfur dibenzofuran } (organic semiconducting materials P4):
Under nitrogen protection, by 4-normal butane epoxide-N, N-bis-(4-pinacol borate phenyl) aniline (171mg,
0.3mmol), 3,7-dibromo sulfur dibenzofuran (135mg, 0.36mmol), three or two argon benzylacetone two palladium (9mg, 0.009mmol) and 2-
Dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl (29mg, 0.072mmol) joins the DMF filling 12mL
Flask in, add sodium carbonate (3mL, 2mol/L) solution after fully dissolving.Subsequently toward nitrogen purge gas about 30min logical in flask
After；Flask is heated to 120 DEG C and carries out Suzuki coupled reaction 36h.Stop polyreaction after cooling, in flask, drip 40ml
Methanol settles；Successively with methanol and normal hexane extracting 24h after being filtered by apparatus,Soxhlet's.Then it is molten with chloroform
Agent extracting to the most colourless, collected chloroformic solution and also is spin-dried for obtaining red powder, obtain poly-4-normal butane epoxide-N, N-bis-(4-base-
Phenyl) aniline-co-3,7-diyl sulfur dibenzofuran } organic semiconducting materials, the lower 50 DEG C of dry 24h of last vacuum.Productivity is 87%.
The above-mentioned reaction equation preparing organic semiconducting materials P4 is as follows:
Molecule measuring test result is: Molecular weight (GPC, THF, R.I): Mn=51.3kDa, Mw/Mn=2.1.
The thermogravimetic analysis (TGA) figure of the organic semiconducting materials of the present embodiment 4 preparation, thermogravimetric curve (TGA) is tested at TA
Carrying out on SDT 2960 instruments, under nitrogen air-flow protection, programming rate is 10K/min.As seen from the figure 5%
Thermal weight loss temperature is 430 DEG C.
The uv-visible absorption spectra figure of the organic semiconducting materials P4 of preparation, ultraviolet-ray visible absorbing light in embodiment 4
Spectrum is measured on Jasco-570 uv analyzer.As seen from the figure: having between 300nm～800nm of Inventive polymers
Absorption wider relatively greatly, wherein maximum absorption band is positioned at 582nm, and wide absorption spectrum shows that P4 is a kind of photovoltaic material.
By test antenna effect spectrum, instrument is FS modular fluorometer/pectrophosphorimeter, to investigate organic semiconductor material
Material P4 triplet emission characteristic.Under the liquid nitrogen of 77K, organic semiconducting materials P4 shows the strongest phosphorescent emissions, emission peak
At 444nm, corresponding triplet energy state is 2.79eV, is much higher than double (4,6-difluorophenyl pyridinato-N, the C2) pyrrole of phosphor material
Pyridine formyl closes the triplet energy state (2.65eV) of iridium (III) FIrpic, and test data result shows that our material can be as indigo plant
Light phosphorescent light body material.
Embodiment 5:
Present embodiment discloses poly-{ 4-n-dodecane epoxide-N, N-bis-(4-pinacol borate benzene that structural formula is following
Base) aniline } (organic semiconducting materials P5):
Under nitrogen protection, by 4-n-dodecane epoxide-N, N-bis-(4-pinacol borate phenyl) aniline (205mg,
0.3mmol), 3,7-dibromo sulfur dibenzofuran (112mg, 0.3mmol), tetra-triphenylphosphine palladium (8mg, 0.006mmol) join and fill
15mL toluene adds in the twoport flask of 50mL, adds potassium carbonate (3mL, 2mol/L) solution after fully dissolving.Subsequently toward flask
In after logical nitrogen purge gas about 10min；Flask is heated to 90 DEG C and carries out Suzuki coupled reaction 60h.Polymerization is stopped after cooling
Reaction, drips in 40ml methanol in flask and settles；Successively with methanol and normal hexane after being filtered by apparatus,Soxhlet's
Extracting 24h.Then with chloroform for solvent extraction to the most colourless, collect chloroformic solution and also be spin-dried for obtaining red powder, obtain that poly-{ 4-is just
Dodecyloxy-N, N-bis-(4-pinacol borate phenyl) aniline } organic semiconducting materials, lower 50 DEG C of last vacuum is dried
24h.Productivity is 73%.
The above-mentioned reaction equation preparing organic semiconducting materials P5 is as follows:
Molecule measuring test result is: Molecular weight (GPC, THF, R.I): Mn=4.3kDa, Mw/Mn=2.4.
The thermogravimetic analysis (TGA) figure of the organic semiconducting materials P5 of the present embodiment 5 preparation, thermogravimetric curve (TGA) is tested at TA
Carrying out on SDT 2960 instruments, under nitrogen air-flow protection, programming rate is 10K/min.As seen from the figure 5%
Thermal weight loss temperature is 395 DEG C.
The uv-visible absorption spectra figure of the organic semiconducting materials P5 of preparation, ultraviolet-ray visible absorbing light in embodiment 5
Spectrum is measured on Jasco-570 uv analyzer.As seen from the figure: having between 300nm～800nm of Inventive polymers
Absorption wider relatively greatly, wherein maximum absorption band is positioned at 584nm, and wide absorption spectrum shows that P5 is a kind of photovoltaic material.
By test antenna effect spectrum, instrument is FS modular fluorometer/pectrophosphorimeter, to investigate organic semiconductor material
Material P5 triplet emission characteristic.Under the liquid nitrogen of 77K, organic semiconducting materials P5 shows the strongest phosphorescent emissions, emission peak
At 448nm, corresponding triplet energy state is 2.77eV, is much higher than double (4,6-difluorophenyl pyridinato-N, the C2) pyrrole of phosphor material
Pyridine formyl closes the triplet energy state (2.65eV) of iridium (III) FIrpic, and test data result shows that our material can be as indigo plant
Light phosphorescent light body material.
Application Example
Organic electroluminescence device 300, its structure such as Fig. 1 it include substrate 301, anode 302, hole injection layer 303, empty
Cave transmitting layer 3 04, luminescent layer 305, electron transfer layer 306, electronics injecting layer 307, negative electrode 308.
In the present embodiment, the material of substrate 301 is glass, vacuum coating anode 302, hole injection successively in substrate 301
Layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electronics injecting layer 307, negative electrode 308, anode 302
The tin indium oxide using square resistance to be 10～20 Ω/, thickness is 150nm, and hole injection layer 303 uses poly-(3,4-ethylene
Dioxy thiophene)-polystyrolsulfon acid, thickness is 30nm, hole transmission layer 304 use N, N '-diphenyl-N, N '-(1-naphthyl)-
1,1 '-biphenyl-4,4 '-diamidogen, thickness is 20nm, and luminescent layer 305 main body luminescent material uses the present invention to implement the chemical combination of 1 preparation
Thing poly-{ 4-normal hexane oxygen-N, N-bis-(4-base-phenyl) aniline-co-3,7-diyl sulfur dibenzofuran }, and mix on the basis of material of main part
Impurity level percent is double (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic conjunction iridium (III) of guest emitting material of 10%, sends out
Photosphere 305 thickness is 20nm, and electron transfer layer 306 uses 5, and (thickness is 30nm for 4,7-diphenyl-1,10-phenanthroline, and electronics is noted
Entering cushion 307 and use lithium fluoride, thickness is 1nm, and negative electrode 308 uses metallic aluminium, and thickness is 100nm.
Organic layer and metal level all use thermal evaporation process to deposit, and vacuum is 10-3～10-5Pa, the thickness of thin film
Using film thickness monitoring instrument to monitor, in addition to guest materials, the evaporation rate of all organic materials is The steaming of lithium fluoride
Sending out speed isThe evaporation rate of metallic aluminium is
This electroluminescent device has higher luminous efficiency, can be widely used in the illumination field such as blueness or white.Device
Current versus brightness-the voltage characteristic of part is to be measured system by the Keithley source with correction silicon photoelectric diode
All measurements that (Keithley 2400 Sourcemeter, Keithley 2000 Cuirrentmeter) completes are all in room temperature
Air completes.Result shows: the maximum electrical efficiency of device is 11.8cd/A, and high-high brightness is 26290cd/m2。
Embodiment described above only have expressed the several embodiments of the present invention, and it describes more concrete and detailed, but also
Therefore the restriction to the scope of the claims of the present invention can not be interpreted as.It should be pointed out that, for those of ordinary skill in the art
For, without departing from the inventive concept of the premise, it is also possible to make some deformation and improvement, these broadly fall into the guarantor of the present invention
Protect scope.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (1)
1. an organic semiconducting materials, it is characterised in that the chemical formula of described organic semiconducting materials is as follows:
Wherein, R is C1～C20Alkyl, n is the integer of 10～100.
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| CN1976883A (en) * | 2004-06-28 | 2007-06-06 | 出光兴产株式会社 | Polycyclic aromatic compound, material for forming light-emitting coating film using the same, and organic electroluminescent device |
| CN101429274A (en) * | 2008-09-17 | 2009-05-13 | 中国科学院长春应用化学研究所 | Poly-fluorene single-component white radiation macromolecule material containing phosphoric acid ester group, preparation method and application thereof |
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| CN102775398B (en) * | 2012-07-25 | 2016-01-06 | 中节能万润股份有限公司 | A kind of Novel bipolar material and application thereof |
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| CN1833470A (en) * | 2003-07-31 | 2006-09-13 | 三菱化学株式会社 | Compound, charge transporting material and organic electroluminescent element |
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| CN103965441A (en) | 2014-08-06 |
| CN105694006B (en) | 2018-01-23 |
| CN105694006A (en) | 2016-06-22 |
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