CN105949041A - Isotropic anthryl compound with oxygen atom substituents, preparation method and application - Google Patents
Isotropic anthryl compound with oxygen atom substituents, preparation method and application Download PDFInfo
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- CN105949041A CN105949041A CN201610343450.XA CN201610343450A CN105949041A CN 105949041 A CN105949041 A CN 105949041A CN 201610343450 A CN201610343450 A CN 201610343450A CN 105949041 A CN105949041 A CN 105949041A
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- organic
- oxygen atom
- semiconducting materials
- organic semiconducting
- substituted anthryl
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- 125000004430 oxygen atom Chemical group O* 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- -1 anthryl compound Chemical class 0.000 title claims abstract description 4
- 239000004065 semiconductor Substances 0.000 claims abstract description 45
- 230000005669 field effect Effects 0.000 claims abstract description 25
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims abstract description 23
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 26
- 239000013078 crystal Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000010410 layer Substances 0.000 claims description 8
- 239000003444 phase transfer catalyst Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 150000001454 anthracenes Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- BPRGLVVFWRNXEP-UHFFFAOYSA-N 2,6-dibromoanthracene Chemical compound C1=C(Br)C=CC2=CC3=CC(Br)=CC=C3C=C21 BPRGLVVFWRNXEP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000005090 crystal field Methods 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- JUFYHUWBLXKCJM-UHFFFAOYSA-N 2,6-dibromoanthracene-9,10-dione Chemical compound BrC1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 JUFYHUWBLXKCJM-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000003983 crown ethers Chemical class 0.000 claims description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 229910052763 palladium Inorganic materials 0.000 claims 2
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 239000002304 perfume Substances 0.000 claims 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 235000011181 potassium carbonates Nutrition 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- GLFDLEXFOHUASB-UHFFFAOYSA-N trimethyl(tetradecyl)azanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)C GLFDLEXFOHUASB-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 23
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000037230 mobility Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004506 ultrasonic cleaning Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- BTEFLANPSMIVPE-UHFFFAOYSA-N CC1=C(B(O)O)C=CC=C1.[O] Chemical compound CC1=C(B(O)O)C=CC=C1.[O] BTEFLANPSMIVPE-UHFFFAOYSA-N 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- PAYSBLPSJQBEJR-UHFFFAOYSA-N naphtho[2,3-e][1]benzothiole Chemical class C1=CC=C2C=C3C(C=CS4)=C4C=CC3=CC2=C1 PAYSBLPSJQBEJR-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/357—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- 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
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
Abstract
The invention relates to an isotropic anthryl compound with oxygen atom substituents, a preparation method and application. The anthryl semiconductor material with oxygen atom substitutions has a following structural formula. The material has good thermal stability and excellent carrier transport efficiency, is isotropic and is widely applicable to organic electroluminescent devices and organic field-effect transistor parts, and performance uniformity of batch-produced devices is greatly improved; the preparation method of the material is simple, and the material is applicable to industrial production.
Description
Technical field
The present invention relates to field of photovoltaic materials, being specifically related to one, to have the substituted anthryl of isotropic oxygen atom organic
Semi-conducting material and its preparation method and application.
Background technology
Along with the fast development of information age, organic electronic device is due to its low cost, the spy such as high-adaptability and easy processing
Property, increasingly paid close attention to by people.As the most basic element of electronic circuit, organic field effect tube comes due to its material
Source is extensive, low cost, can machining at low temperature, the advantage such as and applicable production in enormous quantities compatible with flexible substrates can become current research
Focus.In full stress-strain actively display, extensive and super large-scale integration assembly, organic laser, the aspect such as sensor has
The most potential using value.
Material is basis and the core of organic electronic device, and part organic material of today has reached even in performance
Surmount inorganic semiconductor.Wherein also benzene-like compounds has obtained widely as a very important organic semiconducting materials of class
Paying close attention to and research, acene based semiconductor material has good planar conjugate characteristic, and π-π heap good in crystal mostly
Long-pending, the ideal material being applied in organic field effect tube.Typical acene class organic semiconducting materials has anthracene four
Benzene, Benzo[b etc..The small molecule organic semiconductor material that wherein Benzo[b (Pentacene) is made up of five phenyl ring arranged side by side
Material, is also the organic semiconducting materials that in current report, mobility is the highest, but its fatal shortcoming: light stability is poor.Benzo[b
Cost with still have gap in stability compared with inorganic material.The crystal bandgap of anthracene (Anthracene, also known as anthracene) is big
Being about 3.9eV, only wavelength just can excite at the ultraviolet light of below 310nm, therefore it is the most highly stable.Report at present
The room temperature mobilities of middle anthracene crystal is up to 0.1cm2/ V.s, therefore anthryl field-effect transistor causes people recently and grinds widely
Study carefully interest.
The substituted anthracene-based compounds of oxygen atom is the organic semiconducting materials that a class has good photoelectric properties, and long alkyl chain takes
The anthrathiophene compounds in generation has more report, and focus is more concentrated on introducing thiophene and long alkyl chain base by people
Group increases photoelectric properties and the dissolubility of compound.
Summary of the invention
It is an object of the invention to provide a kind of new oxygen atom substituted anthryl organic semiconducting materials, having of this material
Good stability, higher life-span, and there is isotropic material character；The method meanwhile, preparing this material is simple,
Productivity is high, low cost；And it is applied in organic electroluminescence device, organic field effect tube device that there is good carrier
Mobility and isotropic character.
In order to reach above-mentioned technical purpose, technical scheme is specifically, a kind of substituted anthryl of oxygen atom is organic
Semi-conducting material, its structural formula is structural formula I,
A kind of oxygen atom substituted anthryl organic semiconducting materials preparation method, it is characterised in that preparation process is: by 2,
6-dibromo-anthraquinoneIt is reduced into 2,6-dibromoanthracene4-substituted with oxygen atom again
Oxygen methylphenylboronic acidOr 4-oxygen methylphenylboronic acid ester, it is dissolved in containing catalyst and alkalescence molten by a certain percentage
In the organic solvent of liquid, under anaerobic, it is heated to 90～120 DEG C, carries out Suzuki coupling reaction, react 18h～48h
After, obtain the substituted organic semiconducting materials of hetero atom
Further, described phase transfer catalyst is polyethers, such as crown ether, chain Polyethylene Glycol, Polyethylene Glycol dioxane
Base ether；Quaternary ammonium salt, as benzyltriethylammoinium chloride, tetrabutyl ammonium bromide, tetrabutylammonium chloride, tri-n-octyl methyl ammonium chloride,
Dodecyl trimethyl ammonium chloride, tetradecyl trimethyl ammonium chloride；Tertiary amines, such as any one of pyridine, tri-n-butylamine or
Multiple mixture.
Further, the amount of described phase transfer catalyst is the 1%～5% of the quality of reaction system, and optimum amount is anti-
Answer the 1.5%～2.5% of system quality.
Further, the alkaline matter of described alkaline solution is the one in sodium carbonate, potassium carbonate, bicarbonate, alkalescence
Material is 1: 1～3: 1 with the mol ratio of hetero atom substituted aroma ylboronic acid or borate, and optimum amount is 1.5: 1～2.5: 1.
A kind of it is applied to organic electroluminescence device, the organic semiconducting materials of organic field effect tube device, for oxygen
The substituted anthracene-based compounds of atomOrganic at organic field effect tube of this compound
Layer semiconductor layer has 2.8cm2The carrier mobility of/more than V.s, in the single crystalline layer of organic single-crystal field effect transistor
There is 15cm2The carrier mobility of/more than V.s.
Further, described FET device, it includes grid, the insulating barrier being positioned on grid successively, is positioned at
Organic semiconductor layer on insulating barrier, the source electrode being positioned on organic semiconductor layer and drain electrode.Wherein organic semiconductor layer is
The substituted anthracene-based compounds of oxygen atomThe material of grid is doped silicon wafer, insulating barrier
Material is silicon dioxide, polymethyl methacrylate, styrene, polyvinylphenol, polyvinyl alcohol, poly-ethylene carbonate, gathers
The material of any one of vinyl chloride, Parylene, source electrode and drain electrode is gold.
Further, described organic single-crystal field effect transistor device, the result of single crystal device is as follows: at known monocrystalline
On the premise of each crystal orientation, major axis and short axle and each different crystal orientations between them build field-effect transistor to measure
The field-effect mobility of each different directions, measurement result shows that its result is all at 13cm2/ Vs to 16cm2Between/Vs, show
Isotropic charge transmission.
Beneficial effects of the present invention: oxygen atom substituted anthryl organic semiconducting materials with anthracene as rigid backbone, benzene alkyl
Chain substituent makes it have the heat stability of excellence and higher charge transport properties；This anthryl organic semiconducting materials is made
During thin film so that this thin film has preferable stable appearance, overcome the shortcoming easily crystallized when preparing its thin film again.Oxygen atom
Introducing add the bulk density of molecule space and the regularity of molecules align.The method preparing this material is simple, productivity is high,
Low cost；There is good carrier mobility, be widely used in organic electroluminescence device, organic field effect tube.
Accompanying drawing explanation
Fig. 1 is that oxygen atom replaces anthryl organic semiconducting materials and shows as the structure of the organic field effect tube of organic layer
It is intended to.
Detailed description of the invention
Below in conjunction with the accompanying drawing in the embodiment of the present invention, the technical scheme in the embodiment of the present invention is carried out clear, complete
Describe wholely.Should be appreciated that specific embodiment described herein is only used for explaining the present invention, be not intended to limit the present invention.
Described method is conventional method if no special instructions.Described raw material the most all can obtain from open commercial sources.
Embodiment 1
A kind of hetero atom substituted anthracene class organic semiconducting materials 2,6-bis-(4-methoxybenzene) anthracene (named BOPAnt),
Its structural formula is:
The preparation method of above-mentioned organic semiconducting materials DOBAnt, comprises the steps:
In the single port reaction bulb of 250ml, it is sequentially added into 3.36g 2,6-dibromoanthracene (10mmol), 150ml toluene,
3.80g methoxyphenylboronic acid ester (25mmol), the sodium carbonate liquor of 25ml, 2M, 0.23g tetrakis triphenylphosphine palladium (0.2mmol),
2.7g tri-n-octyl methyl ammonium chloride, logical nitrogen 25 minutes, closed reactor in reactant liquor, it is warming up to 95 DEG C of backflow 24h, terminates
Reaction.Wash with methanol, dilute acid soln, acetone, chloroform successively, be filtrated to get yellow product 2.95g (productivity 75.64%),
Products therefrom is BOPAnt.
Being checked by thermogravimetric analyzer (TGA), analysis condition is nitrogen atmosphere, and scanning speed is 10 DEG C/min,
The decomposition temperature of three kinds of organic semiconducting materials in embodiment 1-3, as shown in table 1, its heat decomposition temperature is up to 391 DEG C (5%
Thermal weight loss) more than, illustrate that this type of material has preferable heat stability.
Table 1: the heat decomposition temperature of organic semiconducting materials
Embodiment 2
The preparation of BOPAnt organic field effect tube
Step one: Wafer Cleaning
If prepare 30mm × 30mm the one silicon chip dry tablet wearing silica inorganic insulating barrier, successively with deionized water,
Isopropanol, acetone ultrasonic cleaning 10 minutes, add hydrogen peroxide and the concentrated sulphuric acid mixing mixed solution of 3: 7 proportions, and 90 DEG C add
Heat 30 minutes, cleaner with deionized water prize Wafer Cleaning.Use isopropanol ultrasonic 10 minutes the most again, dry up with nitrogen.
Step 2: prepared by device
Take the silicon chip after cleaning, use the organic semiconducting materials of preparation in vacuum heat deposition method deposition embodiment 1
A1DOBAnt, vacuum pressure is 6 × 10-4 handkerchief, and heat flow rate is 0.02, and organic semi-conductor thickness is about 50nm.Pass through vacuum
Mask hot evaporation coating method deposition drain-source electrodes, thickness is 70nm, and the device prepared is as shown in Figure 1.
Embodiment 5
Embodiment 3
The preparation of BOPAnt organic single-crystal field effect transistor.
Step one: Wafer Cleaning
If prepare 30mm × 30mm the one silicon chip dry tablet wearing silica inorganic insulating barrier, successively with deionized water,
Isopropanol, acetone ultrasonic cleaning 10 minutes, add hydrogen peroxide and the concentrated sulphuric acid mixing mixed solution of 3: 7 proportions, and 90 DEG C add
Heat 30 minutes, cleaner with deionized water prize Wafer Cleaning.Use isopropanol ultrasonic 10 minutes the most again, dry up with nitrogen.The most right
Substrate carries out surface process, uses
Step 2: carry out crystal growth on substrate and be prepared by device
Use gas gas-phase objects logos (PVT) to carry out crystal growth, cleaned silicon chip is positioned over the crystalline substance of many temperature-area tubular furnaces
Bulk-growth district, is positioned over material sublimation district by material, and sublimation zone temperature arranges 330 degrees Celsius, and crystal growth district temperature is arranged
It is 250 degrees Celsius, keeps the interior normal pressure of pipe and pass to inert nitrogen gas or argon.The substrate of monocrystalline will have been grown subsequently
Carry out the mask evaporation of metal under vacuo.
Embodiment 4
Organic field effect tube device embodiment 2-3 prepared carries out performance test.
Device performance test: the organic field effect tube device that embodiment 4-6 is obtained be placed on equipped with
On Keithley4200 micro operation probe platform, test transfer curve and curve of output respectively.Wherein, described source-drain current output song
Line (abbreviation curve of output) refers to that source-drain current ISD is with the change curve of source-drain voltage VSD in certain grid voltage VG；Wherein, institute
State source-drain current transfer curve (abbreviation transfer curve) and refer to that source-drain current ISD is with grid voltage VG under certain source-drain voltage VSD
Change curve.Threshold voltage is the minimum voltage that induced crystal pipe produces conducting channel, can be by (ISD) 1/2 pair of VG mapping
Being extended down to electric current outside institute's fitting a straight line is voltage gained when 0.Test result is as shown in table 2.
The field effect behavior of table 2 organic field effect tube
As can be seen from the above results, three kinds of organic semiconducting materials all have preferable field effect behavior, already close to
The field effect behavior of amorphous silicon.And the aerial stability of device prepared by these three organic semiconducting materials is preferable,
The synthesis material of organic semiconducting materials is extensive, and synthesis technique is simple, therefore has higher using value.
The anthracene class organic semiconducting materials containing hetero atom substituents the group above embodiment of the present invention provided and system thereof
Preparation Method and application are described in detail, and principle and the embodiment of the present invention are carried out by specific case used herein
Illustrating, the explanation of above example is only intended to help to understand method and the core concept thereof of the present invention, and this specification content is not
It is interpreted as limitation of the present invention.
Claims (13)
1. having isotropic oxygen atom substituted anthryl organic semiconducting materials, its structural formula is structural formula I:
2. one kind has isotropic oxygen atom substituted anthryl organic semiconducting materials preparation method, it is characterised in that system
Standby step is: by 2,6-dibromo-anthraquinoneIt is reduced into 2,6-dibromoanthraceneAgain and oxygen
The substituted phenylboric acid of atomOr borate esterBe dissolved in by a certain percentage containing catalyst and
In the organic solvent of alkaline solution, under anaerobic, it is heated to uniform temperature, carries out Suzuki coupling reaction, react one section
After time, obtain oxygen atom substituted anthryl semi-conducting material.
Oxygen atom the most according to claim 2 substituted anthryl organic semiconducting materials preparation method, it is characterised in that institute
The molar ratio of 2 stated, 6-dibromoanthracene and 4-methoxyphenylboronic acid or 4-methoxyphenylboronic acid ester is 1: 2.5-1: 3.5.
Oxygen atom the most according to claim 2 substituted anthryl organic semiconducting materials preparation method, it is characterised in that institute
That states is heated to uniform temperature, and the reaction temperature carrying out Suzuki coupling reaction is 90～120 DEG C.
Oxygen atom the most according to claim 2 substituted anthryl organic semiconducting materials preparation method, it is characterised in that institute
Stating the response time is 18h～48h.
Oxygen atom the most according to claim 2 substituted anthryl organic semiconducting materials preparation method, it is characterised in that institute
The catalyst stated is organic palladium and the mixture of phase transfer catalyst or organic palladium and organophosphor ligand and phase transfer catalyst
Mixture.
Oxygen atom the most according to claim 6 substituted anthryl organic semiconducting materials preparation method method, it is characterised in that
Described phase transfer catalyst is the mixture of one or more of polyethers, quaternary ammonium salt, tertiary amines.
Oxygen atom the most according to claim 2 substituted anthryl organic semiconducting materials preparation method, it is characterised in that institute
The phase transfer catalyst stated is crown ether, chain Polyethylene Glycol, dialkylethers, benzyltriethylammoinium chloride, the tetrabutyl
Ammonium bromide, tetrabutylammonium chloride, tri-n-octyl methyl ammonium chloride, Dodecyl trimethyl ammonium chloride, tetradecyltrimethylammonium chlorination
Ammonium, pyridine, the mixture of one or more of tri-n-butylamine.
9. according to the oxygen atom substituted anthryl organic semiconducting materials preparation method described in claim 6 or 7 or 8, its feature
Being, the amount of described phase transfer catalyst is the 1%～5% of the mass fraction of anthracene.
10. according to the oxygen atom substituted anthryl organic semiconducting materials preparation method described in claim 6 or 7 or 8, its feature
Being, the amount of described phase transfer catalyst is the 1.5%～2.5% of the mass fraction of anthracene.
11. oxygen atom according to claim 2 substituted anthryl organic semiconducting materials preparation method, it is characterised in that
The alkaline matter of described alkaline solution is the one in sodium carbonate, potassium carbonate, bicarbonate, and alkaline matter replaces virtue with hetero atom
The mol ratio of perfume base boric acid or borate is 1.5: 1～3: 1.
12. 1 kinds of oxygen atom substituted anthryl organic semiconducting materials are in the application of organic assembly, it is characterised in that comprise right
Require the substituted anthracene-based compounds of oxygen atom in 1
13. according to claim 12 are applied to organic electroluminescence device, organic field effect tube device, machine monocrystalline
The oxygen atom substituted anthryl organic semiconducting materials of field-effect transistor, it is partly led at the organic layer of organic field effect tube
Body layer has 2.8cm2The carrier mobility of/more than V.s, and organic layer crystal layer in organic single-crystal field effect transistor
In there is 15cm2The carrier mobility of/more than V.s.
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| CN109081820A (en) * | 2018-07-18 | 2018-12-25 | 南京工业大学 | A kind of semiconductor material based on anthracene, preparation method and organic field effect tube |
| CN112694394A (en) * | 2020-08-25 | 2021-04-23 | 天津大学 | Ultrasensitive multi-output signal biosensor and preparation method and application thereof |
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| CN102093207A (en) * | 2010-12-07 | 2011-06-15 | 浙江大学 | Amorphous Sb-doped zinc tartrate micro-nano spheres and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109081820A (en) * | 2018-07-18 | 2018-12-25 | 南京工业大学 | A kind of semiconductor material based on anthracene, preparation method and organic field effect tube |
| CN112694394A (en) * | 2020-08-25 | 2021-04-23 | 天津大学 | Ultrasensitive multi-output signal biosensor and preparation method and application thereof |
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