CN101928196A - Indene-containing fullerene derivative receptor material and preparation method and use thereof - Google Patents
Indene-containing fullerene derivative receptor material and preparation method and use thereof Download PDFInfo
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- CN101928196A CN101928196A CN2009100867114A CN200910086711A CN101928196A CN 101928196 A CN101928196 A CN 101928196A CN 2009100867114 A CN2009100867114 A CN 2009100867114A CN 200910086711 A CN200910086711 A CN 200910086711A CN 101928196 A CN101928196 A CN 101928196A
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- methyl
- oxygen base
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- indene
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- 239000000463 material Substances 0.000 title claims abstract description 75
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims abstract description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000741 silica gel Substances 0.000 claims abstract description 36
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 36
- 239000012046 mixed solvent Substances 0.000 claims abstract description 18
- 238000010992 reflux Methods 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- 229910003472 fullerene Inorganic materials 0.000 claims abstract description 6
- 230000005669 field effect Effects 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- -1 sec.-propyl Chemical group 0.000 claims description 63
- 150000002469 indenes Chemical class 0.000 claims description 61
- 229960001866 silicon dioxide Drugs 0.000 claims description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 239000003480 eluent Substances 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 238000005119 centrifugation Methods 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
- 229960001701 chloroform Drugs 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims description 8
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 8
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004337 3-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- WAAIAHOYMJQMQN-UHFFFAOYSA-N C(C)C(COCCCCCCC)CCCC Chemical compound C(C)C(COCCCCCCC)CCCC WAAIAHOYMJQMQN-UHFFFAOYSA-N 0.000 claims description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- ZZQWYVKWJHBWRC-UHFFFAOYSA-N [O].C(CCCCCCCCCCC)OCCCCCCCCCCCCC Chemical compound [O].C(CCCCCCCCCCC)OCCCCCCCCCCCCC ZZQWYVKWJHBWRC-UHFFFAOYSA-N 0.000 claims description 4
- YSNYZCPALUKLFL-UHFFFAOYSA-N [O].CCCCCCCCCCC Chemical compound [O].CCCCCCCCCCC YSNYZCPALUKLFL-UHFFFAOYSA-N 0.000 claims description 4
- MEWQFMZMPMAMTG-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCC MEWQFMZMPMAMTG-UHFFFAOYSA-N 0.000 claims description 4
- PNNXBWWSFIVKQW-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCCC PNNXBWWSFIVKQW-UHFFFAOYSA-N 0.000 claims description 4
- FVXZXFWDTIMEMA-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCCCC FVXZXFWDTIMEMA-UHFFFAOYSA-N 0.000 claims description 4
- CIGIRZIOSVQVKQ-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCCCCC CIGIRZIOSVQVKQ-UHFFFAOYSA-N 0.000 claims description 4
- GHDVJGCKFVIIAX-UHFFFAOYSA-N [O].CCCCCCCCCCCCCCCCCCC Chemical compound [O].CCCCCCCCCCCCCCCCCCC GHDVJGCKFVIIAX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 4
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- OTIVLGJBKUFOEX-UHFFFAOYSA-N n-tetradecoxyaniline Chemical compound CCCCCCCCCCCCCCONC1=CC=CC=C1 OTIVLGJBKUFOEX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 6
- 238000010438 heat treatment Methods 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000004020 conductor Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- 239000000470 constituent Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 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 11
- 238000000862 absorption spectrum Methods 0.000 description 6
- 230000010748 Photoabsorption Effects 0.000 description 5
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000001883 metal evaporation Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- JEDHEMYZURJGRQ-UHFFFAOYSA-N 3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1 JEDHEMYZURJGRQ-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/152—Fullerenes
- C01B32/156—After-treatment
-
- 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
-
- 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Composite Materials (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a fullerene derivative receptor material, in particular to an indene-containing fullerene derivative receptor material with high solubility and a preparation method and use thereof. The indene-containing fullerene receptor material is prepared by dissolving the fullerene in o-dichlorobenzene; adding 1,3-di-R1-4-R2-5-R3-6-R4-7-R5-indene, wherein the molar ratio of the 1,3-di-R1-4-R2-5-R3-6-R4-7-R5-indene to the fullerene is 1 to 15; heating for reflux reaction is 2 to 24 h, and the temperature is cooled to the room temperature; adding the product obtained by the reaction to methanol, and centrifuging to separate out deposit; dissolving the deposit in organic solvent and adsorbing on silica gel; and separating through a silica gel column by taking the mixed solvent of organic solvent and petroleum ether as eluant. The indene-containing fullerene derivative receptor material of the invention can be applied to the fields of organic field effect transistors, polymer solar batteries, organic optical conductors and the like.
Description
Technical field
The present invention relates to fullerene derivative receptor material, what particularly a class had an excellent dissolution performance contains the indenes fullerene derivative receptor material, and such contains the preparation method and the purposes of indenes fullerene derivative receptor material.
Background technology
Owing to have premium propertiess such as good electron mobility, solubility property and workability, soccerballene and derivative thereof are widely used in the opto-electronic devices such as organic polymer solar cell, field-effect transistor and organic photoconductor, wherein C
60With its derivative [6,6]-benzene-carbon 61-methyl-butyrate [PCBM] is to use maximum soccerballene acceptor materials.(1)Li，Y.F.；Zou，Y.P.Adv.Mater.2008，20，2952；(2)Hou，J.H.；Tan，Z.A.；Yan，Y.；He，Y.J.；Yang，C.H.；Li，Y.F.J.Am.Chem.Soc.2006，128，4911；(3)Sun，X.B.；Zhou，Y.H.；Wu，W.C.；Liu，Y.Q.；Tian，W.J.；Yu，G.；Qiu，W.F.；Chen，S.Y.；Zhu，D.B.J.Phys.Chem.B2006，110，7702。People obtained a series of its derivatives, but its acceptor performance can not show a candle to PCBM ((1) Rosario Gonzalez, Jan C.Hummelen, and Fred Wudl.J.Org.Chem.1996,60,2618 by revising the alkyl chain on the ester group among the PCBM; (2) S.Ravaine, F.Le Pecq, C.Mingotaud, and P.Delhaes, J.C.Hummelen, F.Wudl, L.K.Patterson.J.Phys.Chem.1995,99,9551; (3) Qingshuo Wei, Takeshi Nishizawa, Keisuke Tajima, Kazuhito Hashimoto.Adv.Mater.2008,20,2211; (4) Martin Drees, Harald Hoppe, Christoph Winder, Helmut Neugebauer, Niyazi S.Sariciftci, Wolfgang Schwinger, Friedrich
Ffler, Christoph Topf, Markus C.Scharber, Zhengguo Zhu and Russell Gaudiana J.Mater.Chem.2005,15,5158).Lenes etc. have isolated the PCBM (bisPCBM) of two additions, do acceptor material with it and prepared solar cell device, performance slightly is better than device performance (the Mantijn Lenes that single addition PCBM does acceptor, Gert-Jan A.H.Wetzelaer, Floris B.Kooistra, Sjoerd C.Veenstra, Kees J.Hummelen, and Paul W.M.Blom.Adv.Mater.2008,20,2116.Yang etc. have done the derivative of some PCBM, they modify the PCBM phenyl ring, introduced alkoxy chain therein, the device result shows that this type of acceptor material has preferable performance (Changduk Yang, Jin Young Kim, Shinuk Cho, Jae Kwan Lee, Alan J.Heeger, and Fred Wudl.J.Am.Chem.Soc.2008,130,644).Kooistra etc. have done the derivative of some PCBM, they modify the PCBM phenyl ring, (Floris B.Kooistra, Joop Knol, Fredrik Kastenberg such as amino, alkylthio have been introduced therein, Lacramioara M.Popescu, Wiljan J.H.Verhees, Jan M.Kroon, and Jan C.Hummelen.Organic Letters.2007,9,551).
Though the derivative of many soccerballenes is produced out, and is used in the solar cell device, its performance is still not as PCBM.In order to improve the solubility property of soccerballene acceptor material, and improve its electronic mobility, the present invention's design has also prepared indene-containing fullerene derivative receptor material.
Summary of the invention
One of purpose of the present invention is to provide indene-containing fullerene derivative receptor material.
Two of purpose of the present invention is to provide the preparation method of indene-containing fullerene derivative receptor material.
Three of purpose of the present invention is to provide the purposes of indene-containing fullerene derivative receptor material.
Indene-containing fullerene derivative receptor material of the present invention has following structure:
Wherein, R1, R2, R3, R4, R5 independently are hydrogen atoms, or C identical or inequality
1～C
20Alkyl, or C identical or inequality
1～C
20Alkoxyl group.
Ring F is the soccerballene of 60,70 or 84 carbon atoms.
Wherein, the value of N is 1 or 2.
Described C
1～C
20Alkyl be methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, the 2-methyl butyl, the 3-methyl butyl, the 1-ethyl-butyl, the 2-ethyl-butyl, 1-propyl group butyl, amyl group, isopentyl, the 2-methyl amyl, the 3-methyl amyl, the 4-methyl amyl, the 1-ethyl pentyl group, the 2-ethyl pentyl group, the 3-ethyl pentyl group, hexyl, isohexyl, 2-methyl hexyl, 3-methyl hexyl, 4-methyl hexyl, 5-methyl hexyl, the 2-ethylhexyl, heptyl, different heptyl, octyl group, iso-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, a kind of in the eicosyl.
Described C
1～C
20Alkoxyl group be methoxyl group, oxyethyl group, propoxy-, isopropoxy, butoxy, isobutoxy, tert.-butoxy, 2-methyl butoxy, 3-methyl butoxy, 1-ethyl butoxy, 2-ethyl butoxy, 1-propyl group butoxy, pentyloxy, isopentyloxy, 2-methyl pentyloxy, 3-methyl pentyloxy, 4-methyl pentyloxy, 1-ethyl pentyloxy, 2-ethyl pentyloxy, 3-ethyl pentyloxy, hexyloxy, different hexyloxy, 2-methyl hexyloxy, 3-methyl hexyloxy, 4-methyl hexyloxy, 5-methyl hexyloxy, the 2-ethyl hexyl oxy, heptan the oxygen base, different heptan the oxygen base, octyloxy, different octyloxy, the ninth of the ten Heavenly Stems oxygen base, the last of the ten Heavenly stems oxygen base, undecane oxygen base, dodecyloxy, tridecane oxygen base, tetradecyloxyaniline, pentadecane oxygen base, n-Hexadecane oxygen base, heptadecane oxygen base, octadecane oxygen base, nonadecane oxygen base, a kind of in the eicosane oxygen base.
The preparation method of indene-containing fullerene derivative receptor material of the present invention:
Soccerballene is dissolved in the orthodichlorobenzene, adds 1,3-two R1-4-R2-5-R3-6-R4-7-R5-indenes, wherein 1, the molar ratio of 3-two R1-4-R2-5-R3-6-R4-7-R5-indenes and soccerballene is 1～15, is heated to the reflux temperature back flow reaction 2～24 hours, is cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the organic solvent and be adsorbed on the silica gel, do eluent with the mixed solvent of organic solvent and sherwood oil, cross silicagel column separate obtain having said structure contain indenes soccerballene acceptor material; Wherein:
The organic solvent in the eluent and the volume ratio of sherwood oil are 1: 100～1: 0;
R1, R2, R3, R4, R5 independently are hydrogen atoms, or C identical or inequality
1～C
20Alkyl, or C identical or inequality
1～C
20Alkoxyl group;
Soccerballene is the soccerballene of 60,70 or 84 carbon atoms.
Described C
1～C
20Alkyl be methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, the 2-methyl butyl, the 3-methyl butyl, the 1-ethyl-butyl, the 2-ethyl-butyl, 1-propyl group butyl, amyl group, isopentyl, the 2-methyl amyl, the 3-methyl amyl, the 4-methyl amyl, the 1-ethyl pentyl group, the 2-ethyl pentyl group, the 3-ethyl pentyl group, hexyl, isohexyl, 2-methyl hexyl, 3-methyl hexyl, 4-methyl hexyl, 5-methyl hexyl, the 2-ethylhexyl, heptyl, different heptyl, octyl group, iso-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, a kind of in the eicosyl.
Described C
1～C
20Alkoxyl group be methoxyl group, oxyethyl group, propoxy-, isopropoxy, butoxy, isobutoxy, tert.-butoxy, 2-methyl butoxy, 3-methyl butoxy, 1-ethyl butoxy, 2-ethyl butoxy, 1-propyl group butoxy, pentyloxy, isopentyloxy, 2-methyl pentyloxy, 3-methyl pentyloxy, 4-methyl pentyloxy, 1-ethyl pentyloxy, 2-ethyl pentyloxy, 3-ethyl pentyloxy, hexyloxy, different hexyloxy, 2-methyl hexyloxy, 3-methyl hexyloxy, 4-methyl hexyloxy, 5-methyl hexyloxy, the 2-ethyl hexyl oxy, heptan the oxygen base, different heptan the oxygen base, octyloxy, different octyloxy, the ninth of the ten Heavenly Stems oxygen base, the last of the ten Heavenly stems oxygen base, undecane oxygen base, dodecyloxy, tridecane oxygen base, tetradecyloxyaniline, pentadecane oxygen base, n-Hexadecane oxygen base, heptadecane oxygen base, octadecane oxygen base, nonadecane oxygen base, a kind of in the eicosane oxygen base.
Described throw out is dissolved in organic solvent in the organic solvent, and the organic solvent in the eluent all is a kind of in trichloromethane, benzene, toluene, chlorobenzene, the orthodichlorobenzene etc.
Indene-containing fullerene derivative receptor material of the present invention can be as the material etc. of preparation organic field effect tube, polymer solar battery and organic photoconductor.
Ultimate analysis
Indenes soccerballene 1 (Indene-F1) among the present invention, indenes soccerballene 2 (Indene-F2), indenes soccerballene 3 (Indene-F3), indenes soccerballene 4 (Indene-F4), indenes soccerballene 5 (Indene-F5), indenes soccerballene 6 (Indene-F6), indenes soccerballene 7 (Indene-F7), indenes soccerballene 8 (Indene-F8), indenes soccerballene 9 (Indene-F9), the results of elemental analyses of indenes soccerballene 10 (Indene-F10) and indenes soccerballene 11 (Indene-F11) soccerballene acceptor material sees Table 1.
Table 1:
Table 1 shows that the measured value of each constituent content and its calculated value are very approaching in the acceptor material, and the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Spectroscopic analysis
Indenes soccerballene 1 (Indene-F1) among the present invention, indenes soccerballene 2 (Indene-F2), indenes soccerballene 7 (Indene-F7) and indenes soccerballene 8 (Indene-F8) soccerballene acceptor material have good photoabsorption in optical wavelength is 200nm～400nm scope, absorption spectrum as shown in Figure 1.
Thermal stability analysis
Indenes soccerballene 1 (Indene-F1) among the present invention, indenes soccerballene 2 (Indene-F2), indenes soccerballene 7 (Indene-F7) and indenes soccerballene 8 (Indene-F8) fullerene derivative receptor material have good thermostability, and its thermogravimetric curve as shown in Figure 2.
This fullerene derivative acceptor material of the present invention has the good solubility energy in organic solvent (as trichloromethane, benzene, toluene, chlorobenzene, orthodichlorobenzene etc.), because soccerballene has higher electronic mobility, also has higher electronic mobility so this class contains the indenes fullerene derivative receptor material.Acceptor material of the present invention can be applied in fields such as organic field effect tube, polymer solar battery and organic photoconductor.
Description of drawings
Fig. 1 is acceptor material Indene-F1, Indene-F2, Indene-F7 and the Indene-F8 absorption spectrum in toluene solution of the embodiment of the invention 1,2,7 and 8.
Fig. 2 is the acceptor material Indene-F1 of the embodiment of the invention 1 and 2 and the thermogravimetric curve of Indene-F2.
Fig. 3 is the I-V curve of photovoltaic device of the acceptor material Indene-F1 of the embodiment of the invention 1.
Embodiment
Below the present invention is further illustrated, but should not regard limitation of the invention as.
Embodiment 1. preparation indenes soccerballene 1[Indene-F1]
1mmol carbon 60 is dissolved in the 100mL orthodichlorobenzene, adds the indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 1 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 45%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，4H)，4.89(t，2H)，3.84(d，1H)，2.92(d，1H)。
The ultimate analysis of Indene-F1 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
The absorption spectrum of Indene-F1 in toluene solution seen Fig. 1, and the result shows that this acceptor has good photoabsorption in optical wavelength is 200nm～400nm scope.
The thermogravimetric curve of Indene-F1 is seen Fig. 2, and the result shows that this acceptor has good thermostability.
Embodiment 2. preparation indenes soccerballene 2[Indene-F2]
1mmol carbon 60 is dissolved in the 100mL orthodichlorobenzene, adds the indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, and centrifugation goes out throw out, is dissolved in throw out in the benzene and is adsorbed on the silica gel,, crosses silicagel column and separates and obtain indenes soccerballene 2 as eluent with the mixed solvent (volume ratio is 2: 1) of sherwood oil and benzene.Productive rate: 35%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，8H)，4.89-4.86(t，4H)，3.84-3.80(d，2H)，2.92-2.90(d，2H)。
The ultimate analysis of Indene-F2 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
The absorption spectrum of Indene-F2 in toluene solution seen Fig. 1, and the result shows that this acceptor has good photoabsorption in optical wavelength is 200nm～400nm scope.
The thermogravimetric curve of Indene-F2 is seen Fig. 2, and the result shows that this acceptor has good thermostability.
Embodiment 3. preparation indenes soccerballene 3[Indene-F3]
1mmol carbon 60 is dissolved in the 100mL orthodichlorobenzene, adds the 6-methoxyl group indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, and centrifugation goes out throw out, is dissolved in throw out in the toluene and is adsorbed on the silica gel,, crosses silicagel column and separates and obtain indenes soccerballene 3 as eluent with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 55%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，3H)，4.87(t，2H)，3.84-3.85(m，4H)，2.92(d，1H)。
The ultimate analysis of Indene-F3 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 4. preparation indenes soccerballene 4[Indene-F4]
1mmol carbon 60 is dissolved in the 100mL orthodichlorobenzene, adds the 6-methoxyl group indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 4 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 55%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，6H)，4.87(t，4H)，3.84-3.85(m，8H)，2.92(d，2H)。
The ultimate analysis of Indene-F4 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
1mmol carbon 60 is dissolved in the 100mL orthodichlorobenzene, adds the different octyloxy indenes of 4-of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the orthodichlorobenzene and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 5 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 55%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，3H)，4.87(t，2H)，3.84-3.85(m，4H)，2.92(d，1H)，2.00-0.89(m，15H)。
The ultimate analysis of Indene-F5 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 6. preparation indenes soccerballene 6[Indene-F6]
1mmol carbon 60 is dissolved in the 100mL orthodichlorobenzene, adds the different octyloxy indenes of 4-of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 6 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 55%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，6H)，4.87(t，4H)，3.84-3.85(m，8H)，2.92(d，2H)，2.00-0.89(m，30H)。
The ultimate analysis of Indene-F6 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 7. preparation indenes soccerballene 7[Indene-F7]
1mmol carbon 60 is dissolved in the 100mL orthodichlorobenzene, adds 1 of 12mmol then, 3-diisooctyl indenes was heated to the reflux temperature back flow reaction 12 hours, was cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 7 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and benzene.Productive rate: 65%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，4H)，4.87(t，2H)，3.84(d，1H)，2.92(d，1H)，2.05-0.9(m，34H)。
The ultimate analysis of Indene-F7 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
The absorption spectrum of Indene-F7 in toluene solution seen Fig. 1, and the result shows that this acceptor has good photoabsorption in optical wavelength is 200nm～400nm scope.
Embodiment 8. preparation indenes soccerballene 8[Indene-F8]
1mmol carbon 70 is dissolved in the 100mL orthodichlorobenzene, adds the indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 8 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 65%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.26-7.87(m，4H)，4.86(t，2H)，3.84(d，1H)，2.92(d，1H)。
The ultimate analysis of Indene-F8 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
The absorption spectrum of Indene-F8 in toluene solution seen Fig. 1, and the result shows that this acceptor has good photoabsorption in optical wavelength is 200nm～400nm scope.
Embodiment 9. preparation indenes soccerballene 9[Indene-F9]
1mmol carbon 70 is dissolved in the 100mL orthodichlorobenzene, adds the 6-methoxyl group indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 9 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 57%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.26-7.87(m，6H)，4.87(t，4H)，3.84-3.85(m，8H)，2.92(d，2H)。
The ultimate analysis of Indene-F9 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
1mmol carbon 70 is dissolved in the 100mL orthodichlorobenzene, adds the 5-hexyloxy indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, and centrifugation goes out throw out, is dissolved in throw out in the benzene and is adsorbed on the silica gel,, crosses silicagel column and separates and obtain indenes soccerballene 10 as eluent with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 57%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.26-7.87(m，3H)，4.87(t，2H)，3.84-3.85(m，3H)，2.92(d，1H)，1.98-0.90(m，11H)。
The ultimate analysis of Indene-F10 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 11. preparation indenes soccerballene 11[Indene-F11]
1mmol carbon 70 is dissolved in the 100mL orthodichlorobenzene, adds 1 of 12mmol then, 3-diisooctyl indenes, heating reflux reaction 12 hours is cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 11 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 65%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.26-7.87(m，4H)，4.87(t，2H)，3.84(d，1H)，2.92(d，1H)，2.05-0.9(m，34H)。
The ultimate analysis of Indene-F11 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 12. preparation indenes soccerballene 12[Indene-F12]
1mmol carbon 84 is dissolved in the 100mL orthodichlorobenzene, adds the indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 12 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 35%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，4H)，4.85(t，2H)，3.84(d，1H)，2.92(d，1H)。
The ultimate analysis of Indene-F12 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 13. preparation indenes soccerballene 13[Indene-F13]
1mmol carbon 84 is dissolved in the 100mL orthodichlorobenzene, adds the 6-methoxyl group indenes of 12mmol then, be heated to the reflux temperature back flow reaction 12 hours, be cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 13 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 34%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，3H)，4.86(t，2H)，3.84-3.85(m，4H)，2.92(d，1H)。
The ultimate analysis of Indene-F13 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 14. preparation indenes soccerballene 14[Indene-F14]
1mmol carbon 84 is dissolved in the 100mL orthodichlorobenzene, adds 4 of 12mmol then, 5-oxyethyl group indenes was heated to the reflux temperature back flow reaction 12 hours, was cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, and centrifugation goes out throw out, is dissolved in throw out in the toluene and is adsorbed on the silica gel,, crosses silicagel column and separates and obtain indenes soccerballene 14 as eluent with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 34%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，2H)，4.86(t，2H)，3.84-3.85(m，5H)，2.92(d，1H)，1.32(t，6H)。
The ultimate analysis of Indene-F14 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 15. preparation indenes soccerballene 15[Indene-F15]
1mmol carbon 84 is dissolved in the 100mL orthodichlorobenzene, adds 1 of 12mmol then, 3-diisooctyl indenes, heating reflux reaction 12 hours is cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, centrifugation goes out throw out, be dissolved in throw out in the trichloromethane and be adsorbed on the silica gel, as eluent, cross silicagel column and separate and obtain indenes soccerballene 15 with the mixed solvent (volume ratio is 2: 1) of sherwood oil and toluene.Productive rate: 25%.
1H-NMR(δ/ppm，CDCl
3/CS
21∶1)：7.36-7.67(m，4H)，4.89(t，2H)，3.84(d，1H)，2.92(d，1H)，2.05-0.89(m，34H)。
The ultimate analysis of Indene-F15 sees Table 1, the result shows that the measured value of constituent content and its calculated value are very approaching, the purity that this acceptor material is described is than higher, and therefore, a series of signs that it is carried out are objectively responding the character of acceptor material own.
Embodiment 16. preparations are based on the photovoltaic device of embodiment 1 acceptor material indenes soccerballene 1 (Indene-F1)
In clean conductive glass (ITO) substrate, apply one deck 30nm thick poly-(3,4-vinyl dioxy thiophene)) (PEDOT)/poly-(styrene sulfonate)) (PSS), wherein the mol ratio of PEDOT: PSS is 1: 1.To gather (3-hexyl thiophene) (P3HT) is dissolved in the chlorobenzene by weight 1: 1 with the soccerballene acceptor material Indene-F1 that embodiment 1 obtains, the concentration that obtains solution is 10mg/mL, and this solution rotating is coated in above the PEDOT:PSS film as active coating, thickness is 100nm, and 80 ℃ are heated half an hour.To above the above-mentioned polymer layer, thickness is 10nm with the Ca metal evaporation, and to above the Ca metal level, thickness is 150nm, obtains photovoltaic device with the Al metal evaporation.
Preparation is the same based on the photovoltaic device of the fullerene derivative receptor material that embodiment 3,4,5,6,7,8,9,10 and 11 obtains.
Being acceptor, P3HT based on embodiment 1 fullerene derivate Indene-F1 sees Fig. 3 for the I-V curve to the photovoltaic device of body, and the open circuit voltage of this device is 0.59V, and short-circuit current is 7.83mA/cm
2, packing factor is 0.40, energy conversion efficiency is 1.84%.
Being acceptor, P3HT based on embodiment 2 fullerene derivate Indene-F2 sees Fig. 3 for the I-V curve to the photovoltaic device of body, and the open circuit voltage of this device is 0.70V, and short-circuit current is 7.24mA/cm
2, packing factor is 0.34, energy conversion efficiency is 1.71%.
Claims (8)
1. indene-containing fullerene derivative receptor material is characterized in that, the described indenes fullerene derivate that contains has following structure:
Wherein:
R1, R2, R3, R4, R5 independently are hydrogen atoms, or C identical or inequality
1～C
20Alkyl, or C identical or inequality
1～C
20Alkoxyl group;
Ring F is the soccerballene of 60,70 or 84 carbon atoms;
The value of N is 1 or 2.
2. indene-containing fullerene derivative receptor material according to claim 1 is characterized in that: described C
1～C
20Alkyl be methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, the 2-methyl butyl, the 3-methyl butyl, the 1-ethyl-butyl, the 2-ethyl-butyl, 1-propyl group butyl, amyl group, isopentyl, the 2-methyl amyl, the 3-methyl amyl, the 4-methyl amyl, the 1-ethyl pentyl group, the 2-ethyl pentyl group, the 3-ethyl pentyl group, hexyl, isohexyl, 2-methyl hexyl, 3-methyl hexyl, 4-methyl hexyl, 5-methyl hexyl, the 2-ethylhexyl, heptyl, different heptyl, octyl group, iso-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, a kind of in the eicosyl.
3. indene-containing fullerene derivative receptor material according to claim 1 is characterized in that: described C
1～C
20Alkoxyl group be methoxyl group, oxyethyl group, propoxy-, isopropoxy, butoxy, isobutoxy, tert.-butoxy, 2-methyl butoxy, 3-methyl butoxy, 1-ethyl butoxy, 2-ethyl butoxy, 1-propyl group butoxy, pentyloxy, isopentyloxy, 2-methyl pentyloxy, 3-methyl pentyloxy, 4-methyl pentyloxy, 1-ethyl pentyloxy, 2-ethyl pentyloxy, 3-ethyl pentyloxy, hexyloxy, different hexyloxy, 2-methyl hexyloxy, 3-methyl hexyloxy, 4-methyl hexyloxy, 5-methyl hexyloxy, the 2-ethyl hexyl oxy, heptan the oxygen base, different heptan the oxygen base, octyloxy, different octyloxy, the ninth of the ten Heavenly Stems oxygen base, the last of the ten Heavenly stems oxygen base, undecane oxygen base, dodecyloxy, tridecane oxygen base, tetradecyloxyaniline, pentadecane oxygen base, n-Hexadecane oxygen base, heptadecane oxygen base, octadecane oxygen base, nonadecane oxygen base, a kind of in the eicosane oxygen base.
4. preparation method according to any described indene-containing fullerene derivative receptor material of claim 1～3 is characterized in that:
Soccerballene is dissolved in the orthodichlorobenzene, adds 1,3-two R1-4-R2-5-R3-6-R4-7-R5-indenes, wherein 1, the molar ratio of 3-two R1-4-R2-5-R3-6-R4-7-R5-indenes and soccerballene is 1～15, is heated to the reflux temperature back flow reaction 2～24 hours, is cooled to room temperature; The product that obtains after the reaction is joined in the methyl alcohol, and centrifugation goes out throw out, is dissolved in throw out in the organic solvent and is adsorbed on the silica gel, does eluent with the mixed solvent of organic solvent and sherwood oil, and the separation of mistake silicagel column obtains containing indenes soccerballene acceptor material,
Wherein:
The organic solvent in the eluent and the volume ratio of sherwood oil are 1: 100～1: 0;
R1, R2, R3, R4, R5 independently are hydrogen atoms, or C identical or inequality
1～C
20Alkyl, or C identical or inequality
1～C
20Alkoxyl group;
Soccerballene is the soccerballene of 60,70 or 84 carbon atoms.
5. preparation method according to claim 4 is characterized in that: described C
1～C
20Alkyl be methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, the 2-methyl butyl, the 3-methyl butyl, the 1-ethyl-butyl, the 2-ethyl-butyl, 1-propyl group butyl, amyl group, isopentyl, the 2-methyl amyl, the 3-methyl amyl, the 4-methyl amyl, the 1-ethyl pentyl group, the 2-ethyl pentyl group, the 3-ethyl pentyl group, hexyl, isohexyl, 2-methyl hexyl, 3-methyl hexyl, 4-methyl hexyl, 5-methyl hexyl, the 2-ethylhexyl, heptyl, different heptyl, octyl group, iso-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, a kind of in the eicosyl.
6. preparation method according to claim 4 is characterized in that: described C
1～C
20Alkoxyl group be methoxyl group, oxyethyl group, propoxy-, isopropoxy, butoxy, isobutoxy, tert.-butoxy, 2-methyl butoxy, 3-methyl butoxy, 1-ethyl butoxy, 2-ethyl butoxy, 1-propyl group butoxy, pentyloxy, isopentyloxy, 2-methyl pentyloxy, 3-methyl pentyloxy, 4-methyl pentyloxy, 1-ethyl pentyloxy, 2-ethyl pentyloxy, 3-ethyl pentyloxy, hexyloxy, different hexyloxy, 2-methyl hexyloxy, 3-methyl hexyloxy, 4-methyl hexyloxy, 5-methyl hexyloxy, the 2-ethyl hexyl oxy, heptan the oxygen base, different heptan the oxygen base, octyloxy, different octyloxy, the ninth of the ten Heavenly Stems oxygen base, the last of the ten Heavenly stems oxygen base, undecane oxygen base, dodecyloxy, tridecane oxygen base, tetradecyloxyaniline, pentadecane oxygen base, n-Hexadecane oxygen base, heptadecane oxygen base, octadecane oxygen base, nonadecane oxygen base, a kind of in the eicosane oxygen base.
7. preparation method according to claim 4 is characterized in that: described throw out is dissolved in the organic solvent, and the organic solvent in the eluent all is a kind of in trichloromethane, benzene, toluene, chlorobenzene, the orthodichlorobenzene.
8. purposes according to any described indene-containing fullerene derivative receptor material of claim 1～3 is characterized in that: the described indenes fullerene derivative receptor material that contains can be as the material of preparation organic field effect tube, polymer solar battery and organic photoconductor.
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| PCT/CN2010/070078 WO2010145210A1 (en) | 2009-06-19 | 2010-01-08 | Receptor material of fullerene derivate comprising indene and process for producing and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351632A (en) * | 2011-08-25 | 2012-02-15 | 西安近代化学研究所 | Preparation method of indene-C60 bisadduct |
| CN103086890A (en) * | 2013-01-22 | 2013-05-08 | 中国科学院化学研究所 | Cyclopropane fullerene derivative as well as preparation method and applications of cyclopropane fullerene derivative |
| CN104370682A (en) * | 2013-08-14 | 2015-02-25 | 国家纳米科学中心 | Methylene cyclopropane fullerene derivative preparation and use thereof |
| CN114409551A (en) * | 2022-01-25 | 2022-04-29 | 华能新能源股份有限公司 | Fullerene derivative material, preparation method thereof and application thereof in perovskite solar cell |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1803741A (en) * | 2005-12-29 | 2006-07-19 | 复旦大学 | [60] Fullerene derivative [C60(C18H14)] with favorable amplitude limiting and film forming properties and preparation method thereof |
| WO2008018931A2 (en) * | 2006-06-13 | 2008-02-14 | Plextronics, Inc. | Organic photovoltaic devices comprising fullerenes and derivatives thereof |
-
2009
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1803741A (en) * | 2005-12-29 | 2006-07-19 | 复旦大学 | [60] Fullerene derivative [C60(C18H14)] with favorable amplitude limiting and film forming properties and preparation method thereof |
| WO2008018931A2 (en) * | 2006-06-13 | 2008-02-14 | Plextronics, Inc. | Organic photovoltaic devices comprising fullerenes and derivatives thereof |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351632A (en) * | 2011-08-25 | 2012-02-15 | 西安近代化学研究所 | Preparation method of indene-C60 bisadduct |
| CN102351632B (en) * | 2011-08-25 | 2014-02-05 | 西安近代化学研究所 | Preparation method of indene-C60 bisadduct |
| CN103086890A (en) * | 2013-01-22 | 2013-05-08 | 中国科学院化学研究所 | Cyclopropane fullerene derivative as well as preparation method and applications of cyclopropane fullerene derivative |
| CN104370682A (en) * | 2013-08-14 | 2015-02-25 | 国家纳米科学中心 | Methylene cyclopropane fullerene derivative preparation and use thereof |
| CN104370682B (en) * | 2013-08-14 | 2016-04-13 | 国家纳米科学中心 | Preparation of a kind of methylenecyclopropanes fullerene derivate and uses thereof |
| CN114409551A (en) * | 2022-01-25 | 2022-04-29 | 华能新能源股份有限公司 | Fullerene derivative material, preparation method thereof and application thereof in perovskite solar cell |
| WO2023142330A1 (en) * | 2022-01-25 | 2023-08-03 | 中国华能集团清洁能源技术研究院有限公司 | Fullerene derivative material and preparation method therefor and application thereof in perovskite solar cell |
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