WO2011113194A1 - 环戊二烯二噻吩-喹喔啉共聚物、其制备方法和应用 - Google Patents
环戊二烯二噻吩-喹喔啉共聚物、其制备方法和应用 Download PDFInfo
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- WO2011113194A1 WO2011113194A1 PCT/CN2010/071053 CN2010071053W WO2011113194A1 WO 2011113194 A1 WO2011113194 A1 WO 2011113194A1 CN 2010071053 W CN2010071053 W CN 2010071053W WO 2011113194 A1 WO2011113194 A1 WO 2011113194A1
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- Prior art keywords
- quinoxaline
- cyclopentadiene
- organic
- group
- compound
- Prior art date
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- 229920000547 conjugated polymer Polymers 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims abstract description 65
- -1 diketone compound Chemical class 0.000 claims abstract description 29
- 229920000642 polymer Polymers 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 238000005859 coupling reaction Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 20
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 238000006619 Stille reaction Methods 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 230000005669 field effect Effects 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- YOHWFAVXPSPSNU-UHFFFAOYSA-N cyclopenta-1,3-diene;quinoxaline;thiophene Chemical compound C1C=CC=C1.C=1C=CSC=1.C=1C=CSC=1.N1=CC=NC2=CC=CC=C21 YOHWFAVXPSPSNU-UHFFFAOYSA-N 0.000 claims description 6
- 238000006053 organic reaction Methods 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 238000003860 storage Methods 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- IFJYURYIRZLXCN-UHFFFAOYSA-N cyclopenta-1,3-diene thiophene Chemical compound S1C=CC=C1.S1C=CC=C1.C1=CC=CC1 IFJYURYIRZLXCN-UHFFFAOYSA-N 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 150000004996 alkyl benzenes Chemical group 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 2
- QWGLNWHWBCINBS-UHFFFAOYSA-N 3-nonylphenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1 QWGLNWHWBCINBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- 125000005594 diketone group Chemical group 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 6
- GJONBFLRKHYPHK-UHFFFAOYSA-N C(CCCCCCC)C1(C=C=CC1)CCCCCCCC Chemical compound C(CCCCCCC)C1(C=C=CC1)CCCCCCCC GJONBFLRKHYPHK-UHFFFAOYSA-N 0.000 description 20
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
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- 230000005587 bubbling Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- VPMJBJSLTPBZLR-UHFFFAOYSA-N 3,6-dibromobenzene-1,2-diamine Chemical compound NC1=C(N)C(Br)=CC=C1Br VPMJBJSLTPBZLR-UHFFFAOYSA-N 0.000 description 3
- LELMSURPXIAXOW-UHFFFAOYSA-N 5,8-dibromo-2,3-diphenylquinoxaline Chemical compound C=1C=CC=CC=1C=1N=C2C(Br)=CC=C(Br)C2=NC=1C1=CC=CC=C1 LELMSURPXIAXOW-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000000944 Soxhlet extraction Methods 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 3
- 229950004394 ditiocarb Drugs 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
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- 238000011160 research Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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- 150000003432 sterols Chemical class 0.000 description 3
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
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- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
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- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
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- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
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- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation 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
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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
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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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- 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
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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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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
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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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- C08G2261/32—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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Definitions
- the invention belongs to the technical field of organic compound synthesis, and in particular relates to a cyclopentadiene dithio. a quinoxaline copolymer, a process for its preparation and an application.
- the energy conversion efficiency of PCPDTBT and PCBM blends has reached 6.5%, but it is still much lower than the conversion efficiency of inorganic solar cells.
- the main constraints to performance improvement are: relatively low carrier mobility of organic semiconductor devices, the optical response of the device does not match the solar radiation spectrum, and the red region of high photon flux is not effectively utilized and carriers are Electrode collection efficiency is low. In order to make polymer solar cells practical applications, it is still the primary task in this research field to develop new materials and greatly improve their energy conversion efficiency.
- a cyclopentadiene dithio is provided.
- a quinolinated conjugated polymer having good solubility, carrier mobility, and strong chemical and structural modification.
- Embodiments of the present invention further provide a cyclopentadienyldithiophene-quinoxaline conjugated polymer in a polymer solar cell, an organic electroluminescence, an organic field effect transistor, an organic optical storage, an organic nonlinear material, or/and an organic Applications in the field of lasers.
- x+y l, 0.5 ⁇ 1, ⁇ is a positive integer less than 100, is an alkyl group of ( ⁇ 0 2 );
- R 2 , R 3 , R4 , R 5 are the same or different groups
- the group is a hydrogen atom, a CH ⁇ o alkyl group or an alkoxy group, an alkyl group-containing group, an alkylpyrrol group-containing group, and an alkylbenzene group-containing group.
- the heteroconjugate was subjected to a stille coupling reaction to obtain the cyclopentadienyldithiophene-quinoxaline conjugated polymer.
- cyclopentadienyldithiophene-quinoxaline conjugated polymer is in the field of polymer solar cells, organic electroluminescence, organic field effect transistors, organic optical storage, organic nonlinear materials or/and organic lasers.
- the polymer contains structural units of cyclopentadiene dithiophene or a derivative thereof, and the two thiophene rings in the structural unit are on the same plane, which effectively prolongs the conjugate property of the polymer and reduces the energy of the polymer. Gap, and this coplanar structure makes it easier to transfer carriers between the two main chains, thereby increasing carrier mobility;
- the polymer contains a quinoxaline unit such that the polymer has high electron transport properties, High glass transition temperature, excellent electrochemical reduction properties; and quinoxaline unit as an excellent acceptor unit with strong electron-withdrawing ability, thus making the polymer of the invention also have strong chemical and structural modification , the electron-donating group and the electron-accepting group can be introduced by a simple method to adjust the electron-withdrawing property;
- the cyclopentadienyldithiophene-quinoxaline conjugated polymer effectively improves the solubility of the material by introducing a long alkyl chain, improves the processing performance, and expands the application in the field of polymer solar cells. Scope; temperature can react to produce the target product, therefore, the preparation process is simple, easy to operate and control, suitable for industrial production; light, organic field effect transistor, organic light storage, organic nonlinear material or/and organic laser field In the process of high temperature treatment, the order and regularity of the arrangement between the groups and the molecular segments in the material can be effectively increased, so that the transport rate and efficiency of carrier mobility are improved, and thus effective.
- the ground has improved the photoelectric conversion efficiency of the device.
- Figure 1 is a poly(4,4-dioctyl-cyclopentadiene (2, lb: 3,4-b,) dithiophene-2,3-bis(phenyl)quinoxaline) using an embodiment of the present invention.
- Figure 3 is a poly(4,4-dioctyl-cyclopentadienyl (2,lb:3,4-b,)dithiophene-2,3-bis(phenyl)quinoxaline) using an embodiment of the present invention.
- the present invention provides a cyclopentadienyldithiophene-quinoxaline conjugated polymer, which has the following formula
- x+y l, 0.5 ⁇ 1, n is a positive integer less than 100, is an alkyl group of CH ⁇ o; and R 2 , R 3 , R 4 , R 5 are the same or different groups,
- the group is an alkyl group or alkoxy group of 11, CH ⁇ o, an alkyl group containing an alkyl group, an alkylpyrrol group-containing group, and an alkylbenzene group-containing group.
- the above-mentioned structural formula of the alkyl group-containing group is preferably a group represented by the following (A), wherein R 7 and R 8 are selected from an alkyl group of CH ⁇ o, and the unsubstituted site on the alkane-containing ring may also be used. Arbitrarily replaced,
- the structural formula of the alkyl-containing pyrrole group is preferably the following (B), wherein R 9 is d
- the structural formula of the alkyl-containing benzene ring group is preferably the following (C), wherein. Is an alkyl group of CH ⁇ o, and R 1Q may be at any position in the unsubstituted position of the benzene ring.
- the polymer of the embodiment of the invention contains a structural unit of cyclopentadiene dithiophene or a derivative thereof, and the two thiophene rings in the structural unit are on the same plane, which effectively prolongs the conjugate property of the polymer and reduces the polymerization.
- the energy gap of the object, and this coplanar structure makes it easier to transfer carriers between the two main chains, thereby increasing carrier mobility, for example, cyclopentadiene (2, lb: 3, 4) -b,)
- carrier mobility for example, cyclopentadiene (2, lb: 3, 4) -b,
- PCPDTBT benzothiadiazole
- the unoptimized carrier mobility of the copolymer of dithiophene and benzothiadiazole (PCPDTBT) has reached 2X 10- 2 cm 1 ⁇ " 1 and therefore contains cyclopentadiene dithiophene Structural units, such as polymers containing cyclopentadiene (2, lb: 3, 4-b,) dithiophene structural units, have important applications in organic solar cells.
- the polymer of the embodiment of the present invention further contains a quinoxaline unit, so that the polymer of the present invention has high electron transport properties, high glass transition temperature, excellent electrochemical reduction property, and quinoxaline unit as one
- the excellent acceptor unit of strong electron-withdrawing ability thus making the polymer of the invention also have strong chemical and structural modification, and the electron-donating group and the electron-accepting group can be introduced by a simple method to adjust the electron-withdrawing property. Expanded its wide application in the field of organic optoelectronic materials.
- the cyclopentadienyldithiophene-quinoxaline conjugated polymer introduces a long alkyl or alkoxy chain, such as an alkyl or alkane of Cl CH ⁇ o
- the oxy group effectively improves the solubility of the material, improves the processing performance, and expands the application range in the field of polymer solar cells.
- Step i adding a diketone compound and an o-phenylenediamine compound to an organic solvent to obtain a dibromo compound of a quinoxaline heteroaryl ring;
- Step ii the above-mentioned quinoxaline heteroaryl ring dibromo compound and 4,4-dialkyl-2,6-bistridecyltin-cyclopentadiene (2, lb: 3, 4-b, ) Dithiophene.
- the compound is subjected to a stille coupling reaction to obtain the cyclopentadiene dithio.
- step i The preparation of the above-mentioned dibromo compound of the quinoxaline heteroaryl ring (ie, step i) is carried out by adding a diketone compound to an o-phenylenediamine compound in a molar ratio of 1:0.1 to 10, and adding the organic solvent at 20 ° C. The reaction was carried out at 120 ° C for 1 to 24 h.
- the minimum amount of the organic solvent should ensure the dissolution of the reaction, and the amount of the organic solvent can be flexibly adjusted according to actual production under the premise of ensuring the minimum dosage, and the organic solvent is preferably acetic acid, m-nonylphenol, decyl alcohol, ethanol or butanol. Etc., most preferred is acetic acid.
- the above stille coupling reaction (ie, step ii) is 4,4-dialkyl-2,6-bistridecyltin-cyclopentadiene (2, lb: 3, 4-b,) dithiophene, 4 , di-dialkyl-2,6-dibromo-cyclopentadiene (2,lb:3,4-b,) dithiophene and quinoxaline heteroaryl ring dibromo compound molar ratio 1: 1 ⁇ 100 : 1 Add the organic reaction solvent, and carry out Stille coupling reaction at 50 °C ⁇ 150 °C for 24 ⁇ 72 h.
- the minimum amount of the organic reaction solvent should ensure the dissolution of the reaction, and the amount of the organic solvent can be flexibly adjusted according to actual production under the premise of ensuring the minimum dosage, and the organic reaction solvent is preferably tetrahydrofuran, ethylene glycol diterpene ether, benzene, hydrazine. At least one of benzene.
- reaction time The shorter the reaction time of the Stille coupling reaction, the smaller the molecular weight of the copolymer may be, or the polymerization is not at all, but the reaction time is longer to a certain extent, the molecular weight of the copolymer does not increase, tends to be stable, and the reaction time The longer the energy consumption, the higher the production cost, so the reaction time is set to be 24 ⁇ 72 h.
- the above Stille coupling reaction may also be added with a catalyst to increase the rate and the target of the coupling reaction, and the addition amount thereof is 4,4-dialkyl-2,6-bistridecyltin-cyclopentadiene (2). , lb: 3, 4-b,) dithia. 0.05 to 50% of the moles.
- the organic palladium catalyst is at least one of Pd 2 (dba) 3 /P(o-Tol) 3 , Pd(PPh 3 ) 4 , Pd(PPh 3 ) 2 Cl 2 ; an organic palladium catalyst and an organophosphine ligand
- the molar ratio of the mixture is 1:2 ⁇ 20.
- the preparation of the dibromo compound of the quinoxaline heteroaryl ring and/or the preparation of the cyclopentadienyl dithiophene-quinoxaline conjugated polymer can be carried out under aerobic or anaerobic conditions, preferably under anaerobic conditions.
- the anaerobic conditions can be carried out by vacuum or by filling with an inert gas, preferably an inert gas, which is an inert gas commonly used in the art, such as nitrogen, argon or the like, preferably nitrogen.
- reaction temperature can be reacted to obtain the target product, and therefore, the preparation method is simple, easy to handle and control, and is suitable for industrial production.
- the order and regularity of the arrangement between the groups and the molecular segments in the material can be effectively increased, and the transport speed and efficiency of the carrier mobility are obtained. Improve, effectively improve the photoelectric conversion efficiency of the device.
- the cyclopentadienyldithiophene-quinoxaline conjugated polymer of the present invention can be used as an active material in an organic photoelectric material, a polymer solar cell, an organic electroluminescence, an organic field effect transistor, an organic optical storage. , organic nonlinear materials or / and applications in the field of organic lasers.
- Example 1 The invention will now be further described in detail by taking the preparation of a specific polymer as an example.
- Example 1 The invention will now be further described in detail by taking the preparation of a specific polymer as an example.
- the mixture was added to a mixed organic reaction solvent of 50 mL of 1:1 ethylene glycol dioxime and tetrahydrofuran, and bubbling for 0.8 h to remove residual oxygen in the reaction environment, and then adding 0.025 mmol of Pd(PPh 3 )4 And continue to bubble for 1 h to remove residual oxygen in the reaction environment, and then heated to 150 ° C for 24 hours.
- the mixed droplets are first added to the decyl alcohol to be sedimented, suction filtered, washed with decyl alcohol, dried, dissolved with chlorobenzene, and added to an aqueous solution of sodium diethyldithiocarbamate, followed by Heat the mixture to 80.
- the structure of the solar cell device is shown in Figure 1.
- the active layer material comprises the poly 4,4-dioctyl-cyclopentadiene (2, lb: 3,4-b') dithiophene-2,3-bis(phenyl)quinoxaline polymer of the present invention.
- an electron donor material [6,6]phenyl-C 61 -butyrate (PCBM ) is used as an electron acceptor material, that is, the device structure is sequentially a glass layer 11, an ITO layer 12, a PEDOT:PSS layer 13, Copolymer active layer 14 and metal layer 15, wherein ITO is indium tin oxide having a sheet resistance of 10-20 ⁇ / ⁇ , PEDOT is polyethylene dioxythiophene, PSS is polystyrene-cross acid; and ITO layer is coated
- the glass 11 of 12 is first ultrasonically cleaned, then treated with oxygen-Plasma, then the PEDOT:PSS layer 13 is applied to the ITO layer, and then the poly-4,4-dioctyl-cyclopenta
- the solar cell device comprises a glass substrate 11, a transparent anode 12, an intermediate auxiliary layer 13, an active layer 14, and a cathode 15 which are sequentially laminated.
- the intermediate auxiliary layer 13 is made of polyethylene dioxythiophene: polystyrene-sulfonic acid composite material.
- the active layer 14 comprises an electron donor material and an electron acceptor material, and the electron donor material adopts the above poly 4,4-dioctyl-cyclopentadiene (2, lb: 3, 4- b,) Dithiophene.
- The-2,3-bis(phenyl)quinoxaline, the electron acceptor material may be [6,6]phenyl-C 61 -butyrate (PCBM for short).
- the transparent anode 12 may be indium tin oxide (abbreviated as ITO), preferably indium tin oxide having a sheet resistance of 10-20 ⁇ /.
- the cathode 15 may be an aluminum electrode or a bimetal layer electrode such as Ca/Al or Ba/Al or the like.
- the glass base layer 11 can be used as the bottom layer.
- the ITO glass is selected, it is ultrasonically cleaned, treated with oxygen-Plasma, and the intermediate auxiliary layer 13 is coated on the ITO glass, and then the 4,4-dioctyl group is polymerized.
- Cyclopentadiene (2, lb: 3, 4-b,) dithiophene-2,3-bis(phenyl)quinoxaline and an electron acceptor material are coated on the intermediate auxiliary layer 13 by blending to form
- the active layer 14 is then deposited on the active layer 14 by vacuum evaporation to obtain the solar cell device described above.
- the transparent anode 12, the intermediate auxiliary layer 13, the active layer 14, the bimetal layer Ca, and the A1 layer have thicknesses of 160 nm, 40 nm, 150 nm, 20 nm, and 70 nm, respectively.
- Dithiophene-2,3-bis(phenyl)quinoxaline absorbs light energy and generates excitons that migrate to the interface of the electron donor/acceptor material and transfer electrons to the electron acceptor Materials, such as PCBM, achieve charge separation, thereby forming free carriers, ie free electrons and holes. These free electrons are transferred to the metal cathode along the electron acceptor material and collected by the cathode.
- the free holes are transferred to the ITO anode along the electron donor material and collected by the anode, thereby forming photocurrent and photovoltage, realizing photoelectric conversion, and external connection.
- the load When the load is 16, it can be powered.
- The-2,3-bis(phenyl)quinoxaline can more fully utilize light energy due to its wide spectral response range, in order to obtain higher photoelectric conversion efficiency. Add the power generation capability of solar cell devices.
- the organic material can also reduce the quality of the solar cell device, and can be fabricated by techniques such as spin coating, which is convenient for mass production.
- an organic electroluminescent device of -2,3-bis(phenyl)quinoxaline which comprises a glass substrate 21, a transparent anode 22, a light-emitting layer 23, a buffer layer 24, and a cathode 25 which are laminated in this order.
- the transparent anode 22 may be made of indium tin oxide (abbreviated as ITO), preferably indium tin oxide having a sheet resistance of 10-20 ⁇ /.
- the light-emitting layer 23 contains the poly 4,4-dioctyl-cyclopentadiene (2,1-b:3,4-b,)dithiophene-2,3-bis(phenyl)quinoxaline in the above embodiment.
- the buffer layer 24 may be LiF or the like, but is not limited thereto.
- the cathode 25 may be, but not limited to, metal A1 or Ba or the like, but is not limited thereto.
- the organic electroluminescent device structure is represented by: ITO/poly 4,4-dioctyl-cyclopentadiene (2,l-b:3,4-b,) dithio.
- Each layer can be formed by an existing method, and poly 4,4-dioctyl-cyclopentadiene (2, lb: 3, 4-b,) dithiophene-2,3-bis(phenyl)quinoxaline It can be formed on ITO by spin coating technique.
- the poly 4,4-dioctyl-cyclopentadiene (2, lb: 3,4-b,) dithio in the above examples is used.
- An organic field effect transistor of -2,3-bis(phenyl)quinoxaline comprising a substrate 31, an insulating layer 32, a modifying layer 33, an organic semiconductor layer 34, and an organic semiconductor layer 34, which are sequentially stacked. Source electrode 35 and drain electrode 36.
- the substrate 31 may be, but not limited to, a highly doped silicon wafer (Si), and the insulating layer 32 may be, but not limited to, a micro-nano (eg, 450 nm) thick SiO 2 .
- the organic semiconductor layer 34 employs the poly 4,4-dioctyl-cyclopentadiene (2, lb: 3,4-b,) dithiophene-2,3-bis(phenyl)quinoxaline described above.
- Both the source electrode 35 and the drain electrode 36 may be, but not limited to, gold.
- the modifying layer 33 can be, but is not limited to, octadecyltrichlorosilane.
- the substrate 31, the insulating layer 32, the modifying layer 33, and the source electrode 35 and the drain electrode 36 can be formed by a conventional method.
- the organic semiconductor layer 34 may be poly 4,4-dioctyl-cyclopentadiene (2, lb: 3, 4-b,) dithiophene-2,3-bis(phenyl)quinidine in the above embodiment. Porphyrin spin-coated on the modified layer 33 On the insulating layer 32.
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EP10847663.1A EP2548909A4 (en) | 2010-03-15 | 2010-03-15 | CONJUGATED POLYMER OF CYCLOPENTADIENEDITHIOPHENE-QUINOXALIN, PREPARATION METHOD THEREFOR, AND USES THEREOF |
US13/582,763 US20120329982A1 (en) | 2010-03-15 | 2010-03-15 | Cyclopentadienedithiophene-quinoxaline conjugated polymer and preparation method and uses thereof |
JP2012555277A JP5746226B2 (ja) | 2010-03-15 | 2010-03-15 | シクロペンタジエンジチオフェン−キノキサリン共重合体、及びその製造方法、並びその応用 |
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US7781673B2 (en) * | 2005-07-14 | 2010-08-24 | Konarka Technologies, Inc. | Polymers with low band gaps and high charge mobility |
US20080262183A1 (en) * | 2007-04-17 | 2008-10-23 | Lutz Uwe Lehmann | Dithienopyrrole-containing copolymers |
JP5190784B2 (ja) * | 2008-08-08 | 2013-04-24 | 株式会社リコー | 重合体 |
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WO2011112701A1 (en) * | 2010-03-09 | 2011-09-15 | Konarka Technologies, Inc. | Photovoltaic module containing buffer layer |
US20130000719A1 (en) * | 2010-03-15 | 2013-01-03 | Ocean's King Lighting Science & Technology Co. Ltd | Organic solar cell and method for manufacturing the same |
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Cited By (6)
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JP2015518497A (ja) * | 2012-03-16 | 2015-07-02 | メルク パテント ゲーエムベーハー | 共役ポリマー |
JP2017137496A (ja) * | 2012-03-16 | 2017-08-10 | メルク パテント ゲーエムベーハー | 共役ポリマー |
JP2018016810A (ja) * | 2012-03-16 | 2018-02-01 | メルク パテント ゲーエムベーハー | 共役ポリマー |
CN102827357A (zh) * | 2012-08-30 | 2012-12-19 | 西安近代化学研究所 | 双噻吩并环戊二烯-氟代喹喔啉共轭聚合物 |
CN114316216A (zh) * | 2021-11-17 | 2022-04-12 | 厦门华厦学院 | 基于含二噻吩并喹喔啉母体为中心的对称型聚合物及柔性电致变色器件 |
CN115594828A (zh) * | 2022-09-30 | 2023-01-13 | 武汉工程大学(Cn) | 一种卤代环戊二噻吩聚合物及其制备方法和在光伏器件中的应用 |
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JP2013521347A (ja) | 2013-06-10 |
EP2548909A4 (en) | 2014-01-22 |
CN102725331B (zh) | 2014-03-12 |
EP2548909A1 (en) | 2013-01-23 |
US20120329982A1 (en) | 2012-12-27 |
CN102725331A (zh) | 2012-10-10 |
JP5746226B2 (ja) | 2015-07-08 |
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