CN102391078A - Benzene ring-contained fullerene derivative and preparation method and use thereof - Google Patents

Benzene ring-contained fullerene derivative and preparation method and use thereof Download PDF

Info

Publication number
CN102391078A
CN102391078A CN201110256761XA CN201110256761A CN102391078A CN 102391078 A CN102391078 A CN 102391078A CN 201110256761X A CN201110256761X A CN 201110256761XA CN 201110256761 A CN201110256761 A CN 201110256761A CN 102391078 A CN102391078 A CN 102391078A
Authority
CN
China
Prior art keywords
soccerballene
formula
sauerstoffatom
thiazolinyl
alkynyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201110256761XA
Other languages
Chinese (zh)
Inventor
王春儒
孟祥悦
舒春英
蒋礼
王太山
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Institute of Chemistry CAS
Original Assignee
Institute of Chemistry CAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Institute of Chemistry CAS filed Critical Institute of Chemistry CAS
Priority to CN201110256761XA priority Critical patent/CN102391078A/en
Publication of CN102391078A publication Critical patent/CN102391078A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • 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

Landscapes

  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Photovoltaic Devices (AREA)

Abstract

The invention provides a benzene ring-contained fullerene derivative and a preparation method and a use thereof. The benzene ring-contained fullerene derivative provided by the invention comprises the following structure shown as a formula (referred to a drawing), and the derivative has excellent solubility, higher lowest unoccupied molecular orbital (LUMO) energy level, and further, has higher electron migration rate. The benzene ring-contained fullerene derivative provided by the invention can be applied to the fields, such as organic solar cells, organic field-effect transistors and organic photoconductors and the like.

Description

A kind ofly contain phenyl ring fullerene derivate and preparation method thereof and application
Technical field
The present invention relates to a kind of contain phenyl ring fullerene derivate and preparation method thereof and application, belong to fullerene derivate and preparation thereof and Application Areas.
Background technology
Soccerballene and verivate thereof are widely used in the electron devices such as organic solar batteries, organic field effect tube and organic photoconductor, wherein, and C 60Verivate [6,6]-benzene-carbon 61-methyl-butyrate (PCBM) be acceptor material commonly used in the organic solar batteries (Yu, G., et al., Science, 1995,270:1789-1791).People have obtained a series of fullerene derivate through PCBM is modified, but its performance does not all surpass PCBM.Recently, two addition fullerene derivant materials cause researchist's extensive concern.Because two addition fullerene derivant materials, effectively weaken electron conjugated and delocalization on the carbon cage of soccerballene than the single addition fullerene derivant material, thereby improve lowest unoccupied molecular orbital (LUMO) energy level of fullerene derivate material.This kind material is as the organic solar batteries acceptor material, because lumo energy is higher, can improves the open circuit voltage of solar cell device and then improve its photoelectric transformation efficiency, boundless prospect arranged aspect the organic solar batteries developing efficiently.
Li Yongfang etc. develop soccerballene acceptor material efficiently, indenes two addition fullerene derivant material (He, Y.J.; Et al., J.Am.Chem.Soc.2010,132:1377-1382); But its synthesis temperature is higher, is reflected under 200 ℃ and just carries out, and has limited the application of this kind material.
Summary of the invention
The purpose of this invention is to provide a kind of contain phenyl ring fullerene derivate and preparation method thereof and application.
Contain the phenyl ring fullerene derivate shown in the formula provided by the invention (I),
Figure BDA0000088289480000011
In the formula (I), R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, R 11And R 12Be selected from Wasserstoffatoms, halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid, nitro, C identical or inequality 1-C 20Alkyl or C identical or inequality 1-C 20Alkoxyl group; Ring F representes soccerballene C 60, soccerballene C 70, soccerballene C 76Or soccerballene C 84Described C 1-C 20Alkyl or alkoxyl group be straight chain, side chain or ring-type; Perhaps wherein one or more carbon atoms can be replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro, and perhaps wherein one or more Wasserstoffatomss can be replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro.
The invention provides the preparation method who contains the phenyl ring fullerene derivate shown in a kind of formula (I), comprise the steps: that compound shown in the formula (II) and soccerballene react promptly to get the said phenyl ring fullerene derivate that contains under the condition that iodide exist; Said soccerballene can be soccerballene C 60, soccerballene C 70, soccerballene C 76Or soccerballene C 84
Figure BDA0000088289480000021
In the formula (II), R 1, R 2, R 3, R 4, R 5And R 6All be selected from Wasserstoffatoms, halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid, nitro, C identical or inequality 1-C 20Alkyl or C identical or inequality 1-C 20Alkoxyl group.
Among the above-mentioned preparation method, described C 1-C 20Alkyl or alkoxyl group be straight chain, side chain or ring-type; Perhaps wherein one or more carbon atoms can be replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro, and perhaps wherein one or more Wasserstoffatomss can be replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro.
Among the above-mentioned preparation method, said iodide can be potassiumiodide or Soiodin.
Among the above-mentioned preparation method, the temperature of said reaction can be 80 ℃-150 ℃, specifically can be 80 ℃ or 150 ℃; The time of said reaction can be 2 hours-24 hours, specifically can be 2 hours or 24 hours.
Need to add mineral ion in above-mentioned preparing method's the reaction process.
The present invention also provides the preparation method who contains the phenyl ring fullerene derivate shown in the another kind of formula (I), comprises the steps:
(1) compound and rongalite react compound shown in the formula of obtaining (III) shown in the formula (II);
(2) compound and soccerballene shown in the formula (III) react and promptly get the said phenyl ring fullerene derivate that contains; Said soccerballene is soccerballene C 60, soccerballene C 70, soccerballene C 76Or soccerballene C 84
Figure BDA0000088289480000031
In formula (II) and the formula (III), R 1, R 2, R 3, R 4, R 5And R 6All be selected from Wasserstoffatoms, halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid, nitro, C identical or inequality 1-C 20Alkyl or C identical or inequality 1-C 20Alkoxyl group.
Among the above-mentioned preparation method, described C 1-C 20Alkyl or alkoxyl group be straight chain, side chain or ring-type; Perhaps wherein one or more carbon atoms can be replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro, and perhaps wherein one or more Wasserstoffatomss can be replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro.
Among the above-mentioned preparation method, the temperature of the said reaction of step (2) can be 60 ℃-150 ℃, specifically can be 85 ℃ or 150 ℃; The time of said reaction can be 2 hours-20 hours, specifically can be 2 hours or 12 hours.
Present method is more excellent, and above-mentioned preparing method's step (2) does not generate other organic or inorganic by product except generating the sulfur dioxide gas product.
The invention provides contain shown in the formula (I) the phenyl ring fullerene derivate can as the preparation organic solar batteries, organic field effect tube and organic photoconductor material in application.
The fullerene derivate material is soluble in common organic solvent shown in the formula provided by the invention (I); Has higher electronic mobility; Higher lumo energy, therefore fullerene derivate of the present invention can use as the material of preparation organic solar batteries, organic field effect tube or organic photoconductor.
The present invention has following beneficial effect: (1) method provided by the invention has been synthesized a kind of novel fullerene derivate, and building-up process is simple, and temperature of reaction is low, and has higher productive rate; (2) fullerene derivate lowest unoccupied molecular orbital provided by the invention (LUMO) energy level is higher, and the organic photovoltaic devices that is prepared into has higher open circuit voltage, and photoelectric transformation efficiency is higher, is a kind of very promising photovoltaic material.
Description of drawings
Fig. 1 is the absorption spectrum of embodiment of the invention 1-4 synthetic fullerene derivate F1-F4 in tetrahydrofuran solution.
Fig. 2 is the thermogravimetric curve of the embodiment of the invention 1 synthetic fullerene derivate F1.
Fig. 3 is the I-V curve of the solar cell of embodiment of the invention 1-3 synthetic fullerene derivate F1-F3 preparation.
Embodiment
Employed experimental technique is ordinary method like no specified otherwise among the following embodiment.
Used material, reagent etc. like no specified otherwise, all can obtain from commercial sources among the following embodiment.
Embodiment 1, preparation contain phenyl ring fullerene derivate F1
Synthetic route is following:
Figure BDA0000088289480000041
1. 10mmol pyrocatechol, 25mmol n-butyl bromide are dissolved in butanone, add 35mmol salt of wormwood and 0.1mmol Tetrabutyl amonium bromide, 90 ℃ are reacted after 20 hours down; Reaction soln is poured in the water, used the dichloromethane extraction water, organic phase is used anhydrous sodium sulfate drying; Revolve to steam and remove organic solvent, cross silicagel column and separate, obtain the oily product and be 1; 2-two n-butoxy benzene, productive rate is 80%.
1H?NMR(400MHz，CDCl 3)：δ(ppm)6.88(s，4H)，3.96(t，4H)，1.88(m，4H)，1.71-1.80(m，4H)，0.98(t，6H)。
2. with 4mmol 1,2-two n-butoxy benzene and 10mmol formaldehyde are dissolved in acetate, add the acetum (mass fraction of contained hydrogen bromide is 33%) of 15mmol hydrogen bromide; Normal temperature reaction down placed reaction soln in-4 ℃ of refrigerators after 12 hours, had insolubles to separate out; Cross and filter white solid and be 1; 2-two brooethyls-4,5-two n-butoxy benzene, productive rate is 60%.
1H?NMR(400MHz，CDCl 3)：δ(ppm)6.84(s，2H)，4.62(s，4H)，4.00(t，4H)，1.80(m，4H)，1.45-1.54(m，4H)，0.96(t，6H)。
3. with 0.25mmol 1,2-two brooethyls-4,5-two n-butoxy benzene and 0.1mmol soccerballene C 60Be dissolved in the toluene, add 0.1mmol potassiumiodide and 0.05mmol 18-hat-6 ethers and after 24 hours reaction soln is poured in the water in reaction under 80 ℃; Use the extracted in toluene water, organic phase is used anhydrous sodium sulfate drying, revolves to steam to remove organic solvent; Cross silicagel column and separate (sherwood oil: toluene=1: 9; V/v), obtain pulverulent solids product F1, productive rate 72%.
1H?NMR(400MHz，CDCl 3)：δ(ppm)6.91-7.39(m，4H)，3.55-4.88(m，16H)，1.85-1.89(m，8H)，1.43-1.57(m，8H)，0.92-0.97(m，12H)。
The mass spectral characteristi of product F1 is seen table 1, and observed value and theoretical molecular are approaching; The absorption spectrum of product F1 in THF seen Fig. 1, in the 200nm-500nm scope, has good absorption; The thermogravimetric curve of product F1 is seen Fig. 2, and the result shows that this material has good thermostability.
The MALDI-TOF mass spectrometry results of the fullerene derivate F1-F4 of table 1 embodiment 1-4 preparation
Embodiment 2, preparation contain phenyl ring fullerene derivate F2
Synthetic route is following:
Figure BDA0000088289480000052
1. with 1 of 0.25mmol, 2-two (brooethyl) benzene and 1mmol rongalite are dissolved in N, in the dinethylformamide (DMF); Add 0.03mmol Tetrabutyl amonium bromide (TBAB), ice bath reaction was down poured reaction soln in the water into after 5 hours; Use the dichloromethane extraction water, organic phase is used anhydrous sodium sulfate drying, revolves to steam to remove organic solvent; Cross silicagel column and separate, obtain the oily product and be compound shown in the formula (1), productive rate is 80%.
2. with the soccerballene C of 0.1mmol 60Be dissolved in toluene with compound shown in the 0.25mmol formula (1), 85 ℃ are reacted after 12 hours down, reaction soln are poured in the water; Use the extracted in toluene water, organic phase is used anhydrous sodium sulfate drying, revolves to steam to remove organic solvent; Cross silicagel column and separate (sherwood oil: toluene=1: 1.2; V/v), obtain pulverulent solids product F2, productive rate is 75%.
1H?NMR(400MHz，CDCl 3)：δ(ppm)7.13-7.85(m，8H)，3.45-4.96(m，8H)。
The mass spectral characteristi of product F2 is seen table 1, and observed value and theoretical molecular are approaching; The absorption spectrum of product F2 in THF seen Fig. 1, in the 200nm-500nm scope, has good absorption.
Embodiment 3, preparation contain phenyl ring fullerene derivate F3
Synthetic route is following:
1. with 10mmol 1,2-dimethoxy benzene and 25mmol formaldehyde are dissolved in acetate, add the acetum (contained hydrogen bromide massfraction 33%) of 30mmol hydrogen bromide; Normal temperature reaction down placed reaction soln in-4 ℃ of refrigerators after 12 hours, had insolubles to separate out; Cross and filter white solid and be 1; 2-two brooethyls-4,5-dimethoxy benzene, productive rate are 65%.
1H?NMR(400MHz，CDCl 3)：δ(ppm)6.85(s，2H)，4.64(s，4H)，3.96(s，6H)。
2. with 0.2mmol 1,2-two brooethyls-4,5-dimethoxy benzene and 0.2mmol soccerballene C 60Be dissolved in the toluene, add 0.1mmol potassiumiodide and 0.05mmol 18-hat-6 ethers, 100 ℃ are reacted after 12 hours down; Reaction soln is poured in the water, used the extracted in toluene water, organic phase is used anhydrous sodium sulfate drying; Revolve to steam and remove organic solvent; Cross silicagel column and separate, obtain single adduct of Powdered soccerballene shown in the formula (2), productive rate is 70%.
1H?NMR(400MHz，CDCl 3)：δ(ppm)7.10(s，2H)，3.48-4.81(m，10H)。
3. with 0.1mmol 1,2-two brooethyls-4, single adduct of soccerballene is dissolved in the toluene shown in 5-two n-butoxy benzene (compound method is seen embodiment 1), the 0.1mmol formula (2); Add 0.1mmol potassiumiodide and 0.04mmol 18-hat-6 ethers, 150 ℃ are reacted after 2 hours down, reaction soln are poured in the water; Use the extracted in toluene water, organic phase is used anhydrous sodium sulfate drying, revolves to steam to remove organic solvent; Cross silicagel column and separate (sherwood oil: toluene=1: 10; V/v), obtain pulverulent solids product F3, productive rate is 75%.
1H?NMR(400MHz，CDCl 3)：δ(ppm)7.13-7.85(m，4H)，3.49-4.88(m，18H)，1.85-1.89(m，4H)，1.43-1.57(m，4H)，0.92-0.97(m，6H)。
The mass spectral characteristi of product F3 is seen table 1, and observed value and theoretical molecular are approaching; The absorption spectrum of product F3 in THF seen Fig. 1, in the 200nm-500nm scope, has good absorption.
Embodiment 4, preparation contain phenyl ring fullerene derivate F4
Synthetic route is following:
Figure BDA0000088289480000071
1. with 1 of 0.25mmol, 2-two (brooethyl) benzene and 1mmol rongalite are dissolved in N, in the dinethylformamide (DMF); Add 0.03mmol Tetrabutyl amonium bromide (TBAB), ice bath reaction was down poured reaction soln in the water into after 5 hours; Use the dichloromethane extraction water, organic phase is used anhydrous sodium sulfate drying, revolves to steam to remove organic solvent; Cross silicagel column and separate, obtain the oily product and be compound shown in the formula (3), productive rate is 80%.
2. with the soccerballene C that contains 70 carbon of 0.1mmol 70Be dissolved in toluene with compound shown in the 0.25mmol formula (3), 150 ℃ are reacted after 2 hours down, reaction soln are poured in the water; Use the extracted in toluene water, organic phase is used anhydrous sodium sulfate drying, revolves to steam to remove organic solvent; Cross silicagel column and separate (sherwood oil: toluene=1: 1.5; V/v), obtain pulverulent solids product F4, productive rate is 80%.
1H?NMR(400MHz，CDCl 3)：δ(ppm)6.98-7.65(m，8H)，3.66-4.18(m，8H)。
The mass spectral characteristi of product F4 is seen table 1, and observed value and theoretical molecular are approaching; The absorption spectrum of product F4 in THF seen Fig. 1, and absorptive character are preferably arranged in the 200nm-800nm scope.
The polymer solar cell device performance characterization of the fullerene derivate F1-F3 preparation of embodiment 5, embodiment 1-3 preparation
What rotation coating one deck 25nm was thick on the ITO that cleans up (tin indium oxide) conductive glass gathers (3; 4-vinyl dioxy thiophene): gather (styrene sulfonate) (PEDOT: PSS); Wherein the mol ratio of PEDOT: PSS is 1: 1; And then with prepared fullerene derivate among the embodiment 1-3 with gather (3-hexyl thiophene) and (P3HT) be dissolved in the orthodichlorobenzene by weight 1.2: 1, the solution total concn is 34mg/mL, and this solution rotating is coated in PEDOT: PSS film surface is as active coating; Thickness is approximately 150nm, 120 ℃ of following thermal treatment 10 minutes; To above-mentioned active coating surface, thickness is approximately 20nm with metal Ca vapor deposition, and to metal Ca surface, thickness is approximately 150nm, obtains organic solar batteries with metal A l vapor deposition.
The performance of the organic solar batteries of above-mentioned preparation is as shown in table 2, and (all tests all record 100mw/cm under 1 sun 2), the photovoltaic device I-V curve of fullerene derivate F1-F3 preparation is seen Fig. 3.
Table 2 contains the performance of organic solar batteries of the fullerene derivate F1-F3 of embodiment 1-3 preparation
Can be drawn by The above results, the phenyl ring fullerene derivate that contains provided by the invention has higher photoelectric transformation efficiency as the solar cell acceptor, is a kind of very promising material.

Claims (10)

1. one type contains the phenyl ring fullerene derivate, it is characterized in that: the said phenyl ring fullerene derivate that contains has following structure:
Figure FDA0000088289470000011
Wherein, R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, R 11And R 12Be selected from Wasserstoffatoms, halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid, nitro, C identical or inequality 1-C 20Alkyl or C identical or inequality 1-C 20Alkoxyl group; Ring F representes soccerballene C 60, soccerballene C 70, soccerballene C 76Or soccerballene C 84
2. one type according to claim 1 contains the phenyl ring fullerene derivate, it is characterized in that: said C 1-C 20Alkyl or alkoxyl group be straight chain, side chain or ring-type; Perhaps wherein one or more carbon atoms are replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro, and perhaps wherein one or more Wasserstoffatomss are replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro.
3. the preparation method who contains the phenyl ring fullerene derivate shown in the formula (I) comprises the steps: that compound shown in the formula (II) and soccerballene react promptly to get the said phenyl ring fullerene derivate that contains under the condition that iodide exist; Said soccerballene is soccerballene C 60, soccerballene C 70, soccerballene C 76Or soccerballene C 84
In the formula (II), R 1, R 2, R 3, R 4, R 5And R 6All be selected from Wasserstoffatoms, halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid, nitro, C identical or inequality 1-C 20Alkyl or C identical or inequality 1-C 20Alkoxyl group.
4. method according to claim 3 is characterized in that: said C 1-C 20Alkyl or alkoxyl group be straight chain, side chain or ring-type; Perhaps wherein one or more carbon atoms are replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro, and perhaps wherein one or more Wasserstoffatomss are replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro.
5. according to claim 3 or 4 described methods, it is characterized in that: the temperature of said reaction is 80 ℃-150 ℃; The time of said reaction is 2 hours-24 hours.
6. according to arbitrary described method among the claim 3-5, it is characterized in that: said iodide are potassiumiodide or Soiodin.
7. contain the preparation method of phenyl ring fullerene derivate shown in the formula (I), comprise the steps:
(1) compound and rongalite react compound shown in the formula of obtaining (III) shown in the formula (II);
(2) compound and soccerballene shown in the formula (III) react and promptly get the said phenyl ring fullerene derivate that contains; Said soccerballene is soccerballene C 60, soccerballene C 70, soccerballene C 76Or soccerballene C 84
Figure FDA0000088289470000021
In formula (II) and the formula (III), R 1, R 2, R 3, R 4, R 5And R 6All be selected from Wasserstoffatoms, halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid, nitro, C identical or inequality 1-C 20Alkyl or C identical or inequality 1-C 20Alkoxyl group.
8. method according to claim 7 is characterized in that: said C 1-C 20Alkyl or alkoxyl group be straight chain, side chain or ring-type; Perhaps wherein one or more carbon atoms are replaced by Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro, and perhaps wherein one or more Wasserstoffatomss are replaced by halogen atom, Sauerstoffatom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyanic acid or nitro.
9. according to claim 7 or 8 described methods, it is characterized in that: the temperature of the said reaction of step (2) is 60 ℃-150 ℃; The time of the said reaction of step (2) is 2 hours-20 hours.
Claim 1 or 2 described one type contain the phenyl ring fullerene derivate as the preparation organic solar batteries, organic field effect tube and organic photoconductor material in application.
CN201110256761XA 2011-09-01 2011-09-01 Benzene ring-contained fullerene derivative and preparation method and use thereof Pending CN102391078A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201110256761XA CN102391078A (en) 2011-09-01 2011-09-01 Benzene ring-contained fullerene derivative and preparation method and use thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201110256761XA CN102391078A (en) 2011-09-01 2011-09-01 Benzene ring-contained fullerene derivative and preparation method and use thereof

Publications (1)

Publication Number Publication Date
CN102391078A true CN102391078A (en) 2012-03-28

Family

ID=45858487

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201110256761XA Pending CN102391078A (en) 2011-09-01 2011-09-01 Benzene ring-contained fullerene derivative and preparation method and use thereof

Country Status (1)

Country Link
CN (1) CN102391078A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104370682A (en) * 2013-08-14 2015-02-25 国家纳米科学中心 Methylene cyclopropane fullerene derivative preparation and use thereof
CN106380380A (en) * 2016-08-29 2017-02-08 北京化工大学 Fullerene derivative and application of fullerene derivative in perovskite solar cells
JP2020512696A (en) * 2017-03-28 2020-04-23 住友化学株式会社 Solvent system for making photosensitive organic electronic devices
CN115279722A (en) * 2020-01-23 2022-11-01 国立大学法人东海国立大学机构 Fullerene derivative, method for producing fullerene derivative, vapor-deposited material, film, and electronic device

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5763719A (en) * 1993-01-20 1998-06-09 Hoechst Ag Thermally stable fullerene derivatives and process for producing the same
WO2010087655A2 (en) * 2009-01-29 2010-08-05 한국화학연구원 Fullerene derivatives and organic electronic device comprising the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5763719A (en) * 1993-01-20 1998-06-09 Hoechst Ag Thermally stable fullerene derivatives and process for producing the same
WO2010087655A2 (en) * 2009-01-29 2010-08-05 한국화학연구원 Fullerene derivatives and organic electronic device comprising the same

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BEATRIZ ILLESCAS ET AL.: "A Facile Formation of Electroactive Fullerene Adducts from Sultines via a Diels Alder Reaction", 《TETRAHEDRON》 *
JOSE´L.SEGURA ET AL.: "o-Quinodimethanes: Efficient Intermediates in Organic Synthesis", 《CHEMICAL REVIEWS》 *
PILAR DE LA CRUZ ET AL.: "Cycloadditions to [60]Fullerene Using Microwave Irradiation:A Convenient and Expeditious Procedure.", 《TETRAHEDRON》 *
SAMBASIVARAO KOTHA ET AL.: "The Diels-Alder Approach for the Synthesis of Tetralin-Based a-Amino Acid Derivatives and their Modification by the Suzuki-Miyaura Cross-Coupling Reaction", 《SYNTHESIS》 *
YOSUKE NAKAMURA ET AL.: "Synthesis and electronic properties of C,-o-quinodimethane adducts", 《J. CHEM.SOC.PERKIN TRANS.》 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN106380380A (en) * 2016-08-29 2017-02-08 北京化工大学 Fullerene derivative and application of fullerene derivative in perovskite solar cells
JP2020512696A (en) * 2017-03-28 2020-04-23 住友化学株式会社 Solvent system for making photosensitive organic electronic devices
JP7330895B2 (en) 2017-03-28 2023-08-22 住友化学株式会社 Solvent system for fabrication of photosensitive organic electronic devices
CN115279722A (en) * 2020-01-23 2022-11-01 国立大学法人东海国立大学机构 Fullerene derivative, method for producing fullerene derivative, vapor-deposited material, film, and electronic device

Similar Documents

Publication Publication Date Title
CN102906152B (en) Polymer containing units of fluorene, anthracene and benzothiadiazole, preparation method and uses thereof
CN102718946A (en) Organic semiconducting polymer and solar battery comprising same
CN106632412B (en) A kind of imide analog compounds and its preparation method and application
EP2562197A1 (en) Copolymer comprising anthracene and benzoselenadiazole, preparing method and uses thereof
CN102686636B (en) Conjugated fluorene polymer, preparing method thereof and solar battery component
CN102504212A (en) Cross-linkable fluorobenzene-containing end-capped conjugated polymer based on benzodithiophene and double thiophene-substituted difluorobenzothiadiazole and application thereof to solar cell
CN102391078A (en) Benzene ring-contained fullerene derivative and preparation method and use thereof
CN102453228A (en) Organic semiconductor material containing fluorene, anthracene and benzodithiophene units, preparation method, and application thereof
CN102286141B (en) Organic semiconductor material containing fluorene, anthracene and thiophene bithiophene, preparation method thereof and application thereof
CN102295748B (en) Fluorine polymer containing anthracene and pyrrole-pyrrole-dione units and preparation method and use thereof
CN102344548B (en) Copolymer containing fluorene and thiophene pyrroledione unit and preparation method and application of copolymer containing fluorene and thiophene pyrroledione unit
CN108659019A (en) Perovskite hole mobile material and preparation method thereof based on triptycene parent nucleus
CN103086890A (en) Cyclopropane fullerene derivative as well as preparation method and applications of cyclopropane fullerene derivative
CN102911002A (en) Fullerene derivative containing double-benzene nucleus and preparation method and application thereof
CN102311535B (en) Polymer containing fluorene, anthracene and thienopyrazine units and preparation method as well as application thereof
CN102311536A (en) Copolymer comprising silafluorene and thiophene pyrroledione units and preparation method as well as application thereof
CN102417584B (en) Metal porphyrin-anthracene organic semiconductor material as well as preparation method and application thereof
TWI753676B (en) Conjugated polymers and organic photovoltaic elements
CN102827185A (en) D-A-D conjugated molecule based on triphenylamine-thiophene imide, and preparation method and application thereof
CN110218296B (en) Structure, synthesis and application of carbazole polymer hole transport material
CN102453231B (en) Organic semiconductor material containing thienylpyrryl diketone unit, and preparation method and application thereof
CN103435616B (en) A kind of D (A-Ar) ntype compound and application thereof
CN102372838B (en) Organic semiconductor material based on fluorene, anthracene and quinoxaline, preparation method thereof and application thereof
CN116063278B (en) Near infrared organic electronic receptor and preparation method and application thereof
CN115043856B (en) Pyrene condensed ring nucleus non-fullerene organic small molecule receptor material and preparation method and application thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20120328