CN101859913B - Cyano-containing high dielectric constant organic silicon electrolyte materials - Google Patents
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- CN101859913B CN101859913B CN2010101829786A CN201010182978A CN101859913B CN 101859913 B CN101859913 B CN 101859913B CN 2010101829786 A CN2010101829786 A CN 2010101829786A CN 201010182978 A CN201010182978 A CN 201010182978A CN 101859913 B CN101859913 B CN 101859913B
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- 239000002001 electrolyte material Substances 0.000 title claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 title claims abstract description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 14
- 239000010703 silicon Substances 0.000 title claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003990 capacitor Substances 0.000 abstract description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract description 3
- 229910001416 lithium ion Inorganic materials 0.000 abstract description 3
- 230000000996 additive effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000002000 Electrolyte additive Substances 0.000 abstract 1
- 238000012983 electrochemical energy storage Methods 0.000 abstract 1
- 230000005693 optoelectronics Effects 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 11
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 6
- -1 organic carbonate ester Chemical class 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 239000002608 ionic liquid Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000005518 polymer electrolyte Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910013872 LiPF Inorganic materials 0.000 description 1
- 101150058243 Lipf gene Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011244 liquid electrolyte Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- AJJVKRVIERKZPK-UHFFFAOYSA-N methyl(triethoxymethyl)silane Chemical compound C(C)OC([SiH2]C)(OCC)OCC AJJVKRVIERKZPK-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
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- 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
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Abstract
本发明提供了一种安全、有效、应用范围广的含氰基高介电常数有机硅电解质材料。其化学结构式如式I。其中R1，R2，R3选自相同或不同的C1-C10烷基或烷氧基，其中至少有一个基团为如(CH2)nO(CH2CH2O)mCH3结构的烷氧基团，n，m为0-10的整数；R4为C1-C20亚甲基。本发明含氰基高介电常数有机硅电解质材料可作为电解质材料或添加剂应用锂离子电池，此外还可以作为电解质材料应用于其它电化学储能器件(如电解电容和超级电容)及其它光电器件(如有机太阳能电池等)。
The invention provides a safe, effective and wide application range organic silicon electrolyte material containing cyano group with high dielectric constant. Its chemical structural formula is as formula I. Wherein R 1 , R 2 , R 3 are selected from the same or different C1-C10 alkyl or alkoxy groups, at least one of which is a structure such as (CH 2 ) n O(CH 2 CH 2 O) m CH 3 The alkoxy group, n, m is an integer of 0-10; R 4 is C1-C20 methylene. The cyano group-containing high dielectric constant organosilicon electrolyte material of the present invention can be used as an electrolyte material or additive for lithium-ion batteries, and can also be used as an electrolyte material for other electrochemical energy storage devices (such as electrolytic capacitors and super capacitors) and other optoelectronic devices (such as organic solar cells, etc.).
Description
Technical field:
The present invention relates to technical field of chemistry, relate in particular to the kind of cyanic high dielectric constant organic silicon electrolyte materials.
Technical background
At present, employed electrolyte mainly is organic carbonate ester type compound and LiPF in the lithium ion battery industry
6The lithium salts system; Still there is fail safe hidden danger technically in the mode of operation of system; Its main cause is that carbonates organic electrolysis material has very high combustibility; Therefore there is huge hidden danger in fail safe, and especially in hybrid power that requires high security, big capacity and high-multiplying power discharge and full electric car application, safety issue is the key factor that these materials of restriction are used.Therefore, all researching and developing safe, effective and eco-friendly organic electrolysis material of new generation energetically both at home and abroad.
Polyethylene glycol oxide (PEO) is the polymer electrolyte of developing the earliest and be applied to lithium grain ion battery, yet the ionic conductivity of PEO is lower, has limited its application.For solving the low conductivity problem of PEO; People such as West disclose the liquid and polymer electrolyte (US2006035154-A1 of one type of carbonated ester group organosilicon in patent; US2004248014-A1); High-k group carbonate group improves the high-k of material, helps the disassociation of ion, thereby improves the ionic conductivity of material.Egashira (J.Power Sources, 18 (2004) 240-244) has reported the representative examples of saturated aliphatic quaternary ammonium salt ionic liquid of cyano-containing, finds that cyanic acid helps the disassociation of ion.International monopoly WO200519185 discloses a kind of five yuan or hexa-atomic aromatic heterocycle ionic liquid of cyano-containing, Chinese patent CN101085762A disclose a kind of cyano-containing based on the cationic ion liquid compound of morpholine.Organic silicon electrolyte materials and ionic liquid material all have high security, but these material synthesis method are complicated, and cost is higher.
Summary of the invention:
The cyano-containing high dielectric constant organic silicon electrolyte materials that the purpose of this invention is to provide a kind of safe, effective, applied range.
The chemical structural formula of the cyano-containing high dielectric constant organic silicon electrolyte materials that the present invention relates to is as shown in the formula I:
R wherein
1, R
2, R
3Be selected from identical or different C1-C10 alkyl or alkoxyl, wherein have at least a group to be as (CH
2)
nO (CH
2CH
2O)
mCH
3The alkoxy grp of structure, n, m are the integer of 0-10; R
4Be the C1-C20 methylene.
Principle of the present invention is, in organic silica-based material structure that contains the EO unit, introduces strong polarity cyanic acid, and the high-k improving material keeps the fail safe of organosilicon material simultaneously.
Cyano-containing high dielectric constant organic silicon electrolyte materials of the present invention can be used as electrolyte or additive and uses lithium ion battery, can be used as electrolyte in addition and is applied to other electrochemical energy storing device (like electrochemical capacitor and super capacitor) and other photoelectric device (like organic solar cell etc.).
Description of drawings
Fig. 1 is the glass transition temperature curve of embodiment of the invention 1-3 cyano-containing high dielectric constant organic silicon electrolyte materials.
Fig. 2 is that the ionic conductivity of embodiment of the invention 1-3 cyano-containing high dielectric constant organic silicon electrolyte materials is with temperature variation curve (1MLiTFSI).
Embodiment:
Below in conjunction with accompanying drawing and embodiment content of the present invention is described further.
The synthetic reaction formula of embodiment is following:
Shown in above-mentioned reaction equation, the first step of following examples is synthetic 3-propyl group nitrile-dimethylchlorosilanes, and process is following:
Under 0 ℃, dimethylchlorosilane (6.7g, 71mmol) slowly splash into acrylonitrile (4.8g, 71.6mmol) with the 5mol% platinum catalyst in, 50 ℃ the heating 16h, directly obtain colorless liquid product, b.p.42 ℃/0.2Torr through decompression distillation.
1H-NMR(600MHz，CDCl
3)：δ＝0.536(s，6H，SiCH
3)，1.074(m，2H，SiCH
2)，1.892(m，2H，SiCH
2CH
2)，2.51(t，2H，J＝7.2，CH
2CN)；
13C?NMR(600MHz，CDCl3)：-0.001，16.688，18.195，18.635，117.889.
Synthesizing of embodiment 1:3-propyl group nitrile-methoxy ethoxy-dimethylsilane (EO1SiC3CN)
3-propyl group nitrile-dimethylchlorosilane (10g, 61.8mmol) slowly splash into glycol monoethyl ether (4.8g, 63.1mmol) with the oxolane of equivalent triethylamine in; Reflux 18h; Filter the back rotary evaporation except that desolvating, obtain colorless liquid product through decompression distillation, b.p.55 ℃/0.2Torr.
1H-NMR(600MHz，CDCl
3)：δ＝0.145(s，6H，SiCH
3)，0.764(m，2H，SiCH
2)，1.738(m，2H，SiCH
2CH
2)，2.382(t，2H，J＝7.0，CH
2CN)，3.378(s，3H，OCH
3)，3.433(J＝4.8Hz，，2H，CH
3OCH
2CH
2)，3.738(t，J＝4.8Hz，2H，CH
2CH
2OS?i)，3.74(t，2H，J＝7.0Hz，CH
2OSi)；、
13C?NMR(600MHz，CDCl3)：0.001，18.159，22.108，22.654，61.170，64.368，76.136，121.959；
29Si(600MHz，CDCl3)：15.647ppm。
Synthesizing of embodiment 2:3-propyl group nitrile-methoxyl group diethoxy-dimethylsilane (EO2SiC3CN)
Use diethylene glycol monomethyl ether to be reactant, adopt the identical synthetic method of embodiment 1, product obtains colourless liquid through decompression distillation, b.p.108-110 ℃/0.2Torr.
1H-NMR(600MHz，CDCl
3)：δ＝0.114(s，6H，SiCH
3)，0.732(m，2H，SiCH
2)，1.713(m，2H，SiCH
2CH
2)，2.358(t，2H，J＝7.0，CH
2CN)，3.65(s，3H，OCH
3)，3.53(m，4H，CH
3OCH
2CH
2)，3.62(m，2H，CH
2CH
2OSi)，3.74(t，2H，J＝7.0Hz，CH
2OSi)；
13C?NMR(600MHz，CDCl3)：-0.001，18.195，18.065，22.082，22.311，60.898，64.404，72.597，74.072，74.666，121.842；
29Si(600MHz，CDCl3)：15.9ppm。
Synthesizing of embodiment 3:3-propyl group nitrile-methoxyl group triethoxy-dimethylsilane (EO3SiCSCN)
Use triethylene glycol monomethyl ether to be reactant, adopt the identical synthetic method of embodiment 1, product obtains colourless liquid through decompression distillation, b.p.125-127 ℃/0.2Torr.
1H-NMR(600MHz，CDCl3)：δ＝0.108(s，6H，SiCH
3)，0.726(m，2H，SiCH
2)，1.71(m，2H，SiCH
2CH
2)，2.356(t，2H，J＝7.0，CH
2CN)，3.57(s，3H，OCH
3)，3.526(m，4H，CH
3OCH
2CH
2)，3.618(m，4H，CH
2CH
2OSi)，3.16(t，2H，J＝5.2Hz，CH
2OSi)；
13C?NMR(600MHz，CDCl3)：0.018，18.114，22.071，22.534，61.067，64.407，72.623，72.658，72.730，74.078，74.665，121.942；
29Si(600MHz，CDCl3)：15.6ppm。
The physicochemical properties data of the cyano-containing high dielectric constant organic silicon electrolyte materials of embodiment 1-3 gained are as shown in table 1:
Table 1
From accompanying drawing and table 1, can find out; Cyano-containing organic silicon electrolyte materials of the present invention has higher high-k (reach～12) and ionic conductivity; And the high-k that has similar structures and do not have a cyanic acid organosilicon material is 4-5 (J.Mater.Chem., 18 (2008), 3713).
Claims (2)
1. cyano-containing high dielectric constant organic silicon electrolyte materials is characterized in that its structural formula is as shown in the formula I:
Wherein, R
1, R
2, R
3Be selected from identical or different C1-C10 alkyl or alkoxyl, wherein having a group at least is (CH
2)
nO (CH
2CH
2O)
mCH
3The alkoxy grp of structure, n, m are the integer of 0-10; R
4Be the C1-C20 methylene.
2. cyano-containing high dielectric constant organic silicon electrolyte materials as claimed in claim 1 is characterized in that said R
1, R
2Be methyl.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103122008B (en) * | 2011-12-13 | 2016-02-24 | 曹坚林 | Silane coupling agent of a kind of cyano-containing and preparation method thereof |
| SG11201509641UA (en) * | 2013-06-04 | 2015-12-30 | Silatronix Inc | Nitrile-substituted silanes and electrolyte compositions and electrochemical devices containing them |
| CN104072533B (en) * | 2014-06-10 | 2016-05-11 | 中国科学院广州能源研究所 | One class is containing silicon nitrile compounds of low polyoxyethylene units and preparation method thereof, application in lithium battery |
| CN119119100A (en) | 2014-10-03 | 2024-12-13 | 塞勒创尼克斯公司 | Functionalized silane, electrolyte composition and electrochemical device containing the same |
| CN105514487A (en) * | 2015-12-30 | 2016-04-20 | 中国科学院广州能源研究所 | A method for cooperating use of organic silicon electrolyte and silicon-based electrode material |
| CN106025358B (en) * | 2016-06-27 | 2018-12-07 | 中国科学院广州能源研究所 | A kind of organic silicon amine electrolyte of dicyanogen methyl isophorone functionalization |
| CN111293364B (en) * | 2018-12-10 | 2021-03-30 | 张家港市国泰华荣化工新材料有限公司 | Non-aqueous electrolyte and lithium ion battery |
| CN112018442B (en) * | 2019-05-29 | 2022-02-08 | 比亚迪股份有限公司 | Lithium ion battery electrolyte and lithium ion battery |
| CN113717211A (en) * | 2021-08-31 | 2021-11-30 | 石家庄圣泰化工有限公司 | Synthesis method of nitrile-group functionalized organic silicon compound |
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| US4505997A (en) * | 1982-06-01 | 1985-03-19 | Agence Nationale De Valorisation De La Recherche (Anvar) | Bis perhalogenoacyl -or sulfonyl-imides of alkali metals, their solid solutions with plastic materials and their use to the constitution of conductor elements for electrochemical generators |
| CN1449069A (en) * | 2002-04-02 | 2003-10-15 | 株式会社日本触媒 | Materials for electrolytic solution and uses thereof |
| CN101548425A (en) * | 2006-12-06 | 2009-09-30 | 三菱化学株式会社 | Nonaqueous electrolyte solution and nonaqueous electrolyte secondary battery |
-
2010
- 2010-05-19 CN CN2010101829786A patent/CN101859913B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4505997A (en) * | 1982-06-01 | 1985-03-19 | Agence Nationale De Valorisation De La Recherche (Anvar) | Bis perhalogenoacyl -or sulfonyl-imides of alkali metals, their solid solutions with plastic materials and their use to the constitution of conductor elements for electrochemical generators |
| CN1449069A (en) * | 2002-04-02 | 2003-10-15 | 株式会社日本触媒 | Materials for electrolytic solution and uses thereof |
| CN101548425A (en) * | 2006-12-06 | 2009-09-30 | 三菱化学株式会社 | Nonaqueous electrolyte solution and nonaqueous electrolyte secondary battery |
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