CN109280155A - Main chain contains the polymer and preparation method and transistor of acetylene bond or ethylene linkage - Google Patents
Main chain contains the polymer and preparation method and transistor of acetylene bond or ethylene linkage Download PDFInfo
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- CN109280155A CN109280155A CN201811088863.3A CN201811088863A CN109280155A CN 109280155 A CN109280155 A CN 109280155A CN 201811088863 A CN201811088863 A CN 201811088863A CN 109280155 A CN109280155 A CN 109280155A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 73
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000005977 Ethylene Substances 0.000 title claims abstract description 14
- 230000005669 field effect Effects 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 6
- -1 palladium chlorides Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052714 tellurium Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229940043279 diisopropylamine Drugs 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 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 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 229920000547 conjugated polymer Polymers 0.000 abstract description 3
- 230000027756 respiratory electron transport chain Effects 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000944 Soxhlet extraction Methods 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 238000005406 washing Methods 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 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- ROIMNSWDOJCBFR-UHFFFAOYSA-N 2-iodothiophene Chemical compound IC1=CC=CS1 ROIMNSWDOJCBFR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000005267 main chain polymer Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- KDKYADYSIPSCCQ-UHFFFAOYSA-N ethyl acetylene Natural products CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
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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
- C08G61/124—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 nitrogen 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
- 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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- 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 potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
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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
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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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- 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
- C08G2261/124—Copolymers alternating
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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
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
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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
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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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
- C08G2261/3241—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 nitrogen atoms as the only heteroatom, e.g. carbazole
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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
- C08G2261/414—Stille 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
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/415—Sonogashira / Hagihara 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
- C08G2261/514—Electron transport
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- C08G2261/90—Applications
- C08G2261/92—TFT applications
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- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
The present invention discloses the polymer that main chain contains acetylene bond or ethylene linkage and preparation method and transistor, by being copolymerized a variety of narrow band gap units with donor-acceptor-donor (D-A-D) structure with containing acetylene bond or ethylenic linkage derivative unit, the bipolarity conjugated polymer of hole migration and electron transfer capabilities is obtained while had.Bipolarity conjugated polymer prepared by the present invention is applied in organic field effect tube as active layer material.
Description
Technical field
The present invention relates to organic field effect tube technical fields more particularly to a kind of main chain to contain acetylene bond or ethylene linkage
Donor-receiver type polymer and preparation method and organic field effect tube.
Background technique
Relative to crystal silicon field-effect transistor industry, organic field effect tube (OFETs) is because its structure easily modifies, can
The advantages such as solution is processed, large area flexible preparation and preparation cost are low obtain the extensive concern of academia and industrial circle.
The material of OFET is predominantly conjugated small molecule and conjugated polymer material, such material are organic material that main chain is aromatic ring structure
Material can obtain the OFET material of heterogeneity and different performance by the modification of different backbone structure unit and side chain unit
Material.
Currently, the mobility (including N-shaped and p-type material) of the OFET based on small molecule and polymer can be more than
10cm2·V-1·S-1, mobility performance reached the application requirement in related semiconductor field.Relative to single type (N-shaped or
P-type) OFET material, the organic material with dipole characteristic (having hole and electron transfer capabilities simultaneously) has wider
Using such as organic memory and phase inverter etc., therefore, the developing material in relation to bipolarity OFET become especially urgent and again
It wants.The present invention, can be further rich by designing and preparing the Bipolar Polymer semiconductor material with solution working ability
The application of rich bipolar semiconductor device and the preparation cost for reducing such devices.
Summary of the invention
The purpose of the present invention is to provide donor-receiver type polymer and preparations that a kind of main chain contains acetylene bond or ethylene linkage
Method and organic field effect tube.
Technical scheme is as follows:
The present invention provides a kind of donor-receiver type polymer that main chain contains acetylene bond or ethylene linkage, wherein the polymer
Chemical structural formula it is as follows:
Wherein n is the integer of 10-100；
Ar1For the structural unit with donor-acceptor-donor type, it is chosen in particular from one of following structural formula:
Ar2For the aromatic compound containing acetylene bond or ethylene linkage, it is chosen in particular from one of following structural formula:
Wherein, Ar1And Ar2In
(1)R1=C1~C30Straight chain or branched alkyl；
(2)R2、R3=H, C1~C30Straight chain or branched alkyl, OC1~OC30Straight chain or branched alkoxy；
(3) X=O, S, Se, Te or NR1；
(4) Y=O, S, Se, Te, NR1、C(R1)2、Si(R1)2Or Ge (R1)2。
It should be noted that Ar1Middle R1And Ar2Middle R1It may be the same or different, independently selected from C1~C30Straight chain
Or branched alkyl.Ar1Middle R2And Ar2Middle R2It may be the same or different, independently selected from H, C1~C30Straight chain or
Branched alkyl, OC1~OC30Straight chain or branched alkoxy.Ar1Middle R2And R3It may be the same or different, independently select
From H, C1~C30Straight chain or branched alkyl, OC1~OC30Straight chain or branched alkoxy.Ar1Middle X and Ar2Middle X can phase
Together, it can also be different, independently selected from O, S, Se, Te or NR1。
Further, the chemical structural formula of the polymer is as follows:
Wherein n is the integer of 10-100.
Further, the chemical structural formula of the polymer is as follows:
Wherein n is the integer of 10-100.
The present invention also provides a kind of preparation methods of polymer, wherein the polymer is under palladium-containing catalyst
It is obtained by Stille Sonogashira polymerization reaction, reaction equation is as follows:
(1) Stille polymerization reaction are as follows:
Wherein n is
The integer of 10-100；
(2) Sonogashira polymerization reaction are as follows:
Wherein n is
The integer of 10-100.
Stille polymerization reaction of the present invention includes: the Ar containing double bromine groups1Unit with contain double trimethyl-tin-radicals
The Ar of group2Unit is using tetrakis triphenylphosphine palladium as catalyst, and toluene and n,N-Dimethylformamide are mixed solvent, in 80-120
Degree Celsius, react 12-72 hours (such as 24 hours) under inert gas shielding.Wherein, the molar content of tetrakis triphenylphosphine palladium is situated between
Between 0.1% and 10%, the volume ratio of toluene and n,N-Dimethylformamide is 4:1, the Ar containing double bromine groups1Unit with
Ar containing double tin trimethyl groups2The molar concentration of unit is between 0.1 mole every liter and 1 mole every liter.
Sonogashira polymerization reaction of the present invention includes: the Ar containing double bromine groups1Unit with contain double alkynyls
Ar2For unit using two (triphenylphosphine) palladium chlorides, cuprous iodide and diisopropylamine as catalyst system, tetrahydrofuran is solvent,
80-120 degrees Celsius, react 12-72 hours (such as 24 hours) under inert gas shielding.Wherein, two (triphenylphosphine) palladium chloride
Molar content between 0.1% and 10%, the molar content of cuprous iodide is between 10% and 1000%, diisopropylamine
Molar content between 10% and 3000%, the Ar containing double bromine groups1Unit and the Ar containing double alkynyls2Unit rubs
That concentration is between 0.1 mole every liter and 1 mole every liter.
The present invention also provides a kind of organic field effect tubes, including active layer, wherein the material of the active layer is this
The invention polymer.Further, the active layer with a thickness of 40~1000 nanometers.Polymer of the present invention has
Bipolar transmission performance has hole transport performance and electronic transmission performance.
Specifically, organic field effect tube structure of the present invention includes the substrate stacked gradually, source electrode and drain electrode, has
Active layer, dielectric layer and grid, wherein the material of the active layer is polymer of the present invention；Or the organic effect
Transistor includes the substrate stacked gradually, drain and gate, active layer, dielectric layer, source electrode, wherein the material of the active layer is
Polymer of the present invention.
Active layer in organic field effect tube of the present invention can realize by solution processing method, including spin coating,
Brushing, spraying, dip-coating, roller coating, silk-screen printing, printing or inkjet printing methods.
The utility model has the advantages that the present invention provides the designs and preparation of a kind of novel main chain polymer containing acetylene bond/ethylene linkage, and
It is applied to organic field effect tube as active layer material.By the introducing of acetylene bond/ethylene linkage, so that subject polymer has
There is better flatness, to improve the piling up property of solid-state of polymer, increase the transmission performance of carrier, obtains high move
Shifting rate；In addition, by the polymer for introducing donor-receiver structure, so that the quasi polymer has double carriers transmission performance.Institute
The polymer stated has excellent photoelectric properties, and in the potential industrialized production applied to field effect transistor.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of organic field effect tube device in embodiment 10.
Fig. 2 is the cavity type saturation plot of polymer P 1 in embodiment 10.
Fig. 3 is the cavity type transfer characteristic curve figure of polymer P 1 in embodiment 10.
Fig. 4 is the electron type saturation plot of polymer P 1 in embodiment 10.
Fig. 5 is the electron type transfer characteristic curve figure of polymer P 1 in embodiment 10.
Specific embodiment
The present invention provide a kind of donor-receiver type polymer that main chain contains acetylene bond or ethylene linkage and preparation method with it is organic
Field effect transistor, it is to make the purpose of the present invention, technical solution and effect clearer, clear and definite, further to the present invention below
It is described in detail.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to limit this hair
It is bright.
Embodiment 1: the synthesis of polymer P 1
In 50ml three neck round bottom flask, it is separately added into 1 (0.2038g, 0.2mmol), 2 (0.121g, 0.2mmol), four
(triphenylphosphine) palladium (4.6mg, 2%eqv.) and 6ml dry toluene, the anhydrous n,N-Dimethylformamide of 2ml lead to argon gas protection,
For 24 hours in 118 DEG C of reactions.Reaction terminates, and is cooled to room temperature, and reaction solution is added dropwise in the methanol of 250ml stirring, obtains powdered solid
Polymer head product is obtained by filtration in body.Then methanol, acetone, n-hexane Soxhlet extraction are used respectively, it is finally cable-styled with chloroform
Extracting obtains final polymer solution, after chloroform soln is cooled to room temperature, is added dropwise in the 250ml methanol of stirring, mistake
Filter, drying, obtain 1 133mg of polymer P.
Embodiment 2: the synthesis of polymer P 2
In 50ml three neck round bottom flask, it is separately added into 1 (0.196g, 0.2mmol), 2 (0.121g, 0.2mmol), four
(triphenylphosphine) palladium (4.6mg, 2%eqv.) and 6ml dry toluene, the anhydrous n,N-Dimethylformamide of 2ml lead to argon gas protection,
For 24 hours in 115 DEG C of reactions.Reaction terminates, and is cooled to room temperature, and reaction solution is added dropwise in the methanol of 250ml stirring, obtains powdered solid
Polymer head product is obtained by filtration in body.Then methanol, acetone, n-hexane Soxhlet extraction are used respectively, it is finally cable-styled with chloroform
Extracting obtains final polymer solution, after chloroform soln is cooled to room temperature, is added dropwise in the 250ml methanol of stirring, mistake
Filter, drying, obtain 2 161mg of polymer P.
Embodiment 3: the synthesis of polymer P 3
In 50ml three neck round bottom flask, it is separately added into 1 (0.196g, 0.2mmol), 2 (0.121g, 0.2mmol), four
(triphenylphosphine) palladium (4.6mg, 2%eqv.) and 6ml dry toluene, the anhydrous n,N-Dimethylformamide of 2ml lead to argon gas protection,
For 24 hours in 120 DEG C of reactions.Reaction terminates, and is cooled to room temperature, and reaction solution is added dropwise in the methanol of 250ml stirring, obtains powdered solid
Polymer head product is obtained by filtration in body.Then methanol, acetone, n-hexane Soxhlet extraction are used respectively, it is finally cable-styled with chloroform
Extracting obtains final polymer solution, after chloroform soln is cooled to room temperature, is added dropwise in the 250ml methanol of stirring, mistake
Filter, drying, obtain 3 150mg of polymer P.
The synthesis of embodiment 4:2- acetylene trimethyl silicane thiophene
In 50ml three neck round bottom flask, it is added 2- iodothiophen (2.1g, 10mmol), trimethyl silicane ethyl-acetylene (0.98g,
10mmol), cuprous iodide (0.095g, 5%eqv.), two (triphenylphosphine) palladium chlorides (0.14g, 2%eqv.) and 10ml tri-
Ethamine.Under argon atmosphere, reaction 12h is stirred at reflux at 70 DEG C.Reaction terminates, and is cooled to room temperature, and vacuum distillation removes triethylamine.
With 50ml n-hexane extraction product, saturated common salt is washed three times, and distillation washing three times, anhydrous magnesium sulfate dries, filters, and decompression is steamed
Solvent is removed in distillation.Head product is chromatographed to obtain colourless liquid, yield 85% with silica gel/petroleum ether column.
The synthesis of embodiment 5:2- thiophene acetylene
In two mouthfuls of round-bottomed flasks of 50ml, it is added 2- acetylene trimethyl silicane thiophene (1.8g, 10mmol), potassium carbonate
(1.38g) and 15ml methanol, under nitrogen protection, stirring at normal temperature 4h.Product is extracted with 50ml methylene chloride, saturated common salt washing three
Time, distillation washing three times, anhydrous magnesium sulfate dries, filters, and vacuum distillation removes solvent under lower temperature.Obtain yellow oily liquid
Body, yield 88%.
The synthesis of embodiment 6:1,2- Dithiophene acetylene
In 50ml three neck round bottom flask, it is added 2- iodothiophen (2.52g, 12mmol), 2- thiophene acetylene (0.96g,
8.9mmol), cuprous iodide (0.085g, 5%eqv.), two (triphenylphosphine) palladium chlorides (0.125g, 2%eqv.) and 12ml
Triethylamine.Under argon atmosphere, reaction 12h is stirred at reflux at 70 DEG C.Reaction terminates, and reaction solution is cooled to room temperature, and vacuum distillation removes
Remove triethylamine.Product is extracted with 50ml methylene chloride, saturated common salt is washed three times, and distillation washing three times, anhydrous magnesium sulfate is dry,
Filtering, vacuum distillation remove solvent.Crude product petroleum ether: methylene chloride (5:1) mixed solvent makees eluent, silica gel column chromatography
Isolated yellow solid, yield 75%.
The synthesis of bis- (the 5- trimethyl-tin-radical thiophene) acetylene of embodiment 7:1,2-
In 50ml long-neck three neck round bottom flask, 1,2- Dithiophene acetylene (0.57g, 3mmol) and 30ml anhydrous four is added
Hydrogen furans keeps the temperature 10min at -78 DEG C.The hexane solution that 2.7ml concentration is 2.5mol/L n-BuLi is added dropwise in flask
(6.6mmol), and 2h is kept the temperature at -78 DEG C.The tetrahydrofuran solvent of trimethyltin chloride (1.8g, 9mmol) is added, slowly rises
Overnight to room temperature reaction.Vacuum distillation removes solvent, obtains yellow solid.With recrystallizing methanol crude product, yellow sheet is obtained
Crystal, yield 83%.
Embodiment 8: the synthesis of polymer P 4
In 50ml three neck round bottom flask, it is separately added into 1 (0.196g, 0.2mmol), 2 (0.103g, 0.2mmol), four
(triphenylphosphine) palladium (4.6mg, 2%eqv) and 6ml dry toluene, the anhydrous n,N-Dimethylformamide of 2ml lead to argon gas protection, in
116 DEG C of reactions are for 24 hours.Reaction terminates, and is cooled to room temperature, and reaction solution is added dropwise in the methanol of 250ml stirring, obtains powdered solid
Polymer head product is obtained by filtration in body.Then methanol, acetone, n-hexane Soxhlet extraction are used respectively, it is finally cable-styled with chloroform
Extracting obtains final polymer solution, after chloroform soln is cooled to room temperature, is added dropwise in the 250ml methanol of stirring, mistake
Filter, drying, obtain 4 112mg of polymer P.
Embodiment 9: the synthesis of polymer P 5
In 50ml three neck round bottom flask, it is separately added into 1 (0.196g, 0.2mmol), 2 (0.103g, 0.2mmol), four
(triphenylphosphine) palladium (4.6mg, 2%eqv) and 6ml dry toluene, the anhydrous n,N-Dimethylformamide of 2ml lead to argon gas protection, in
119 DEG C of reactions are for 24 hours.Reaction terminates, and is cooled to room temperature, and reaction solution is added dropwise in the methanol of 250ml stirring, obtains powdered solid
Polymer head product is obtained by filtration in body.Then methanol, acetone, n-hexane Soxhlet extraction are used respectively, it is finally cable-styled with chloroform
Extracting obtains final polymer solution, after chloroform soln is cooled to room temperature, is added dropwise in the 250ml methanol of stirring, mistake
Filter, drying, obtain 5 127mg of polymer P.
Embodiment 10: the preparation of organic field effect tube
Organic field effect tube device is to contact type, uses silver as source electrode and drain electrode, specific device architecture: Ag/ polymerization
Object/CYTOP/Au, wherein the polymer is the polymer P 1 that embodiment 1 synthesizes.Specific device fabrication process: using glass as
Substrate sputters one layer of silver as source electrode (30 nanometers) and drain electrode (30 nanometers) in glass surface；In the spin coating of source electrode and drain electrode surface
One layer of polymeric P1 is as active layer (80 nanometers), then spin coating one dielectric layer CYTOP (400 nanometers) on active layer,
Grid (60 nanometer) of the one layer of layer gold of vacuum evaporation as device under similarity condition.Device in no encapsulating humidity about
To be tested in 50% atmospheric environment.The transistor device length and width channel ratio (W/L) of preparation is 500/70 micron.Transistor
Photoelectric properties tested on Semiconductor Parameter Analyzer (Aglient 4155C) and step instrument, test environment be room temperature
Air atmosphere, test result are shown in Fig. 1-5 and table 1.Fig. 1 shows for the structure with polymer P 1 for the OFET device of active layer material
Schematic diagram.Fig. 2 and Fig. 3 is expressed as the cavity type saturation plot and transfer characteristic curve figure of polymer P 1；Fig. 4 and Fig. 5
It is expressed as the electron type saturation plot and transfer characteristic curve figure of polymer P 1.As can be seen from the figure 1 table of polymer P
Reveal significant and effective dipole characteristic, i.e. P1 can either transporting holes can transmit electronics again.Table 1 is the OFET mobility of P1
It summarizes, is 0.15cm by 1 hole mobility of polymer P of device architecture of Fig. 12V-1s-1, electron mobility 0.08cm2V-1s-1。
The mobility of table 1, polymer P 1
In conclusion the present invention provides the designs and preparation of a kind of novel main chain polymer containing acetylene bond/ethylene linkage, and
It is applied to organic field effect tube as active layer material.By the introducing of acetylene bond/ethylene linkage, so that subject polymer has
There is better flatness, to improve the piling up property of solid-state of polymer, increase the transmission performance of carrier, obtains high move
Shifting rate；In addition, by the polymer for introducing donor-receiver structure, so that the quasi polymer has double carriers transmission performance.Institute
The polymer stated has excellent photoelectric properties, and in the potential industrialized production applied to field effect transistor.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (10)
1. the donor-receiver type polymer that a kind of main chain contains acetylene bond or ethylene linkage, which is characterized in that the chemistry of the polymer
Structural formula is as follows:
Wherein n is the integer of 10-100；
Ar1For the structural unit with donor-acceptor-donor type, it is chosen in particular from one of following structural formula:
Ar2For the aromatic compound containing acetylene bond or ethylene linkage, it is chosen in particular from one of following structural formula:
Wherein, Ar1And Ar2In
(1)R1=C1~C30Straight chain or branched alkyl；
(2)R2、R3=H, C1~C30Straight chain or branched alkyl, OC1~OC30Straight chain or branched alkoxy；
(3) X=O, S, Se, Te or NR1；
(4) Y=O, S, Se, Te, NR1、C(R1)2、Si(R1)2Or Ge (R1)2。
2. polymer according to claim 1, which is characterized in that the chemical structural formula of the polymer is as follows:Wherein n is the integer of 10-100.
3. polymer according to claim 1, which is characterized in that the chemical structural formula of the polymer is as follows:Wherein n is the integer of 10-100.
4. a kind of preparation method of the described in any item polymer of claim 1-3, which is characterized in that the polymer is to contain
It is obtained under palladium catalyst by Stille Sonogashira polymerization reaction, reaction equation is as follows:
(1) Stille polymerization reaction are as follows:
Wherein n is 10-
100 integer；
(2) Sonogashira polymerization reaction are as follows:
Wherein n is 10-
100 integer.
5. the preparation method of polymer according to claim 4, which is characterized in that the Stille polymerization reaction includes:
Ar containing double bromine groups1Unit and the Ar containing double tin trimethyl groups2Unit is using tetrakis triphenylphosphine palladium as catalyst, first
Benzene and n,N-Dimethylformamide are mixed solvent, are reacted 12-72 hours under 80-120 degrees Celsius, inert gas shielding.
6. the preparation method of polymer according to claim 5, which is characterized in that the molar content of tetrakis triphenylphosphine palladium
Between 0.1% and 10%, the volume ratio of toluene and n,N-Dimethylformamide is 4:1, the Ar containing double bromine groups1Unit
With the Ar containing double tin trimethyl groups2The molar concentration of unit is between 0.1 mole every liter and 1 mole every liter.
7. the preparation method of polymer according to claim 4, which is characterized in that the Sonogashira polymerization reaction
It include: the Ar containing double bromine groups1Unit and the Ar containing double alkynyls2Unit is with two (triphenylphosphine) palladium chlorides, cuprous iodide
It is catalyst system with diisopropylamine, tetrahydrofuran is solvent, and it is small that 12-72 is reacted under 80-120 degrees Celsius, inert gas shielding
When.
8. the preparation method of polymer according to claim 7, which is characterized in that two (triphenylphosphine) palladium chlorides rub
That content is between 0.1% and 10%, and between 10% and 1000%, diisopropylamine rubs the molar content of cuprous iodide
That content is between 10% and 3000%, the Ar containing double bromine groups1Unit and the Ar containing double alkynyls2Unit it is mole dense
Degree is between 0.1 mole every liter and 1 mole every liter.
9. a kind of organic field effect tube, including active layer, which is characterized in that the material of the active layer is claim 1-
3 described in any item polymer.
10. organic field effect tube according to claim 9, which is characterized in that the active layer with a thickness of 40-
1000 nanometers.
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