IPC분류정보
국가/구분 |
United States(US) Patent
등록
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국제특허분류(IPC7판) |
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출원번호 |
US-0114452
(2011-05-24)
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등록번호 |
US-8609287
(2013-12-17)
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발명자
/ 주소 |
- Zhang, Zhengcheng
- Zhang, Lu
- Amine, Khalil
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출원인 / 주소 |
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대리인 / 주소 |
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인용정보 |
피인용 횟수 :
2 인용 특허 :
26 |
초록
▼
Compounds may have general Formula I, II, or III: where R1, R2, R3, and R4 are independently H, F, Cl, Br, CN, NO2, a alkyl group, a haloalkyl group, a phosphate group, a polyether group; or R1 and R2, or R3 and R4, or R2 and R3 (in the case of Formula II) may join together to form a fused ring on
Compounds may have general Formula I, II, or III: where R1, R2, R3, and R4 are independently H, F, Cl, Br, CN, NO2, a alkyl group, a haloalkyl group, a phosphate group, a polyether group; or R1 and R2, or R3 and R4, or R2 and R3 (in the case of Formula II) may join together to form a fused ring on the benzene ring; and X and Z are independently a group of Formula A: where R5 and R6 and R7 are independently H, F, Cl, Br, CN, NO2, a alkyl group, a haloalkyl group, a phosphate group, or a polyether group; R7 is H, F, Cl, Br, CN, NO2, a alkyl group, a haloalkyl group, a phosphate group, or a polyether group; n is an integer from 1 to 8; and m is an integer from 1 to 13. Such compounds may be used as redox shuttles in electrolytes for use in electrochemical cells, batteries and electronic devices.
대표청구항
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1. A compound represented by Formula I, II, or III: wherein: R1 is n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl;R2 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether, or R1 and R2 join together to form a ring;R3 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or po
1. A compound represented by Formula I, II, or III: wherein: R1 is n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl;R2 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether, or R1 and R2 join together to form a ring;R3 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether; orwhere the compound is represented by Formula II, R1 and R2, or R2 and R3 join together to form a ring;R4 is n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl; andX and Z are independently a group of Formula A: wherein: R5 and R6 are independently H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether;R7 is alkyl, haloalkyl, phosphate, or polyether;n is an integer from 1 to 8; andm is an integer from 1 to 13. 2. The compound of claim 1, wherein R2 and R3 are hydrogen. 3. The compound of claim 1 represented by Formula I. 4. The compound of claim 3, wherein: R2 and R3 are independently H, C1-C4 alkyl, C1-C4 haloalkyl, or a polyether group having from 2 to 20 carbon atoms;R5 and R6 at each occurrence are individually H, a C1-C4 alkyl, a C1-C4 haloalkyl, H, Cl, Br, or I;R7 is alkyl;n is 1 or 2; andm is 1 to 8. 5. The compound of claim 1 represented by Formula II. 6. The compound of claim 1 represented by Formula III. 7. The compound of claim 6, wherein: R1 and R4 are tert-butyl;R2 and R3 are H;R5 and R6 at each occurrence are individually H or methyl;R7 is methyl, or ethyl;n is 1 or 2; andm is 1 to 8. 8. The compound of claim 1, wherein R7 is C1-C4 alkyl. 9. A compound which is 1,4-bis(2-(2-methoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; 1,4-bis(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; or 1,4-bis(2-(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene. 10. An electrolyte comprising: an alkali metal salt;a polar aprotic solvent; anda redox shuttle comprising a compound represented by Formula I, II, or III: wherein: R1 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether;R2 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether, or R1 and R2 join together to form a ring;R3 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether; or where the compound is represented by Formula II, R1 and R2, or R2 and R3 join together to form a ring;R4 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether; or R3 and R4 join together to form a ring; andX and Z are independently a group of Formula A: wherein: R5 and R6 are independently H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether;R7 is H, alkyl, haloalkyl, phosphate, or polyether;n is an integer from 1 to 8;m is an integer from 1 to 13; andwherein the electrolyte solution is substantially non-aqueous. 11. An electrochemical device comprising a cathodean anode; anda substantially non-aqueous electrolyte comprising: an alkali metal salt;a polar aprotic solvent; anda compound represented by Formula I, II, or III;wherein: Formula I, II, and III are: R1 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether;R2 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether, or R1 and R2 join together to form a ring;R3 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether; or where the compound is represented by Formula II, R1 and R2, or R2 and R3 join together to form a ring;R4 is H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether; or R3 and R4 join together to form a ring; andX and Z are independently a group of Formula A: R5 and R6 are independently H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, phosphate, or polyether;R7 is H, alkyl, haloalkyl, phosphate, or polyether;n is an integer from 1 to 8; andm is an integer from 1 to 13. 12. The electrolyte of claim 10, wherein R1, R2, R3, and R4 are independently H, C1-C4 alkyl, C1-C4 haloalkyl, or a polyether having from 2 to 20 carbon atoms. 13. The electrolyte of claim 10, wherein R1 and R4 are individually H, alkyl or haloalkyl, and R2 and R3 are hydrogen. 14. The electrolyte of claim 10, wherein R1 and R4 are individually H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl, and R2 and R3 are H. 15. The electrolyte of claim 10 represented by Formula III. 16. The electrolyte of claim 15, wherein: R1 and R4 are individually H, alkyl or haloalkyl;R2 and R3 are hydrogen;R5 and R6 at each occurrence are individually H or methyl;R7 is H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl;n is 1 or 2;m is 1 to 8. 17. The electrolyte of claim 15, wherein: R1 and R4 are tert-butyl;R2 and R3 are H;R5 and R6 at each occurrence are individually H or methyl;R7 is H, methyl, or ethyl;n is 1 or 2; andm is 1 to 8. 18. The electrolyte of claim 10, wherein the compound is 1-nitro-3-tert-butyl-2,5-di-oligo(ethylene glycol)benzene; 1-cyano-3-tert-butyl-2,5-di-oligo(ethylene glycol)benzene; 1,4-di-tert-butyl-2,3-di-oligo(ethylene glycol)benzene; 5-tert-butyl-1,3-dinitro-2,4-di-oligo(ethylene glycol)benzene; 1-(benzyloxy)-4-bromo-2,3-di-oligo(ethylene glycol)benzene; 1,3,5-tri-tert-butyl-2,4-di-oligo(ethylene glycol)benzene; 2-methyl-1,4-di-oligo(ethylene glycol)benzene; 2,3-dimethyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-dimethyl-1,4-di-oligo(ethylene glycol)benzene; 2,6-dimethyl-1,4-di-oligo(ethylene glycol)benzene; 2,3,6-trimethyl-1,2-di-oligo(ethylene glycol)benzene; 2,3,5,6-tetramethyl-1,4-di-oligo(ethylene glycol)benzene; 4-methyl-1,2-di-oligo(ethylene glycol)benzene; 2-ethyl-1,4-di-oligo(ethylene glycol)benzene; 2,3-diethyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-diethyl-1,4-di-oligo(ethylene glycol)benzene; 2,6-diethyl-1,4-di-oligo(ethylene glycol)benzene; 2,3,6-triethyl-1,2-di-oligo(ethylene glycol)benzene; 2,3,5,6-tetraethyl-1,4-di-oligo(ethylene glycol)benzene; 4-ethyl-1,2-di-oligo(ethylene glycol)benzene; 2,5-diisopropyl-1,4-di-oligo(ethylene glycol)benzene; 2-tert-butyl-1,4-di-oligo(ethylene glycol)benzene; 2,3-di-tert-butyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-butyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-pentyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-butyl-3,6-di-nitro-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-butyl-3,6-di-cyano-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-butyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-dicyclohexyl-1,4-di-oligo(ethylene glycol)benzene; 4-tert-butyl-1,2-di-oligo(ethylene glycol)benzene; 4,5-di-tert-butyl-1,2-di-oligo(ethylene glycol)benzene; 4,5-di-tert-pentyl-1,2-di-oligo(ethylene glycol)benzene; 4,5-di-tert-butyl-1,2-diethoxybenzene; 9,10-di-oligo(ethylene glycol)-1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydroanthracene; 9,10-di-oligo(ethylene glycol)-1,4:5,8-diethano-1,2,3,4,5,6,7,8-octahydroanthracene; 1,4-bis(2-(2-methoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; 1,4-bis(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; or 1,4-bis(2-(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene. 19. The electrolyte of claim 10, wherein the compound is 1,4-bis(2-(2-methoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; 1,4-bis(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; or 1,4-bis(2-(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene. 20. The electrochemical device of claim 11, wherein the compound is 1-nitro-3-tert-butyl-2,5-di-oligo(ethylene glycol)benzene; 1-cyano-3-tert-butyl-2,5-di-oligo(ethylene glycol)benzene; 1,4-di-tert-butyl-2,3-di-oligo(ethylene glycol)benzene; 5-tert-butyl-1,3-dinitro-2,4-di-oligo(ethylene glycol)benzene; 1-(benzyloxy)-4-bromo-2,3-di-oligo(ethylene glycol)benzene; 1,3,5-tri-tert-butyl-2,4-di-oligo(ethylene glycol)benzene; 2-methyl-1,4-di-oligo(ethylene glycol)benzene; 2,3-dimethyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-dimethyl-1,4-di-oligo(ethylene glycol)benzene; 2,6-dimethyl-1,4-di-oligo(ethylene glycol)benzene; 2,3,6-trimethyl-1,2-di-oligo(ethylene glycol)benzene; 2,3,5,6-tetramethyl-1,4-di-oligo(ethylene glycol)benzene; 4-methyl-1,2-di-oligo(ethylene glycol)benzene; 2-ethyl-1,4-di-oligo(ethylene glycol)benzene; 2,3-diethyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-diethyl-1,4-di-oligo(ethylene glycol)benzene; 2,6-diethyl-1,4-di-oligo(ethylene glycol)benzene; 2,3,6-triethyl-1,2-di-oligo(ethylene glycol)benzene; 2,3,5,6-tetraethyl-1,4-di-oligo(ethylene glycol)benzene; 4-ethyl-1,2-di-oligo(ethylene glycol)benzene; 2,5-diisopropyl-1,4-di-oligo(ethylene glycol)benzene; 2-tert-butyl-1,4-di-oligo(ethylene glycol)benzene; 2,3-di-tert-butyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-butyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-pentyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-butyl-3,6-di-nitro-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-butyl-3,6-di-cyano-1,4-di-oligo(ethylene glycol)benzene; 2,5-di-tert-butyl-1,4-di-oligo(ethylene glycol)benzene; 2,5-dicyclohexyl-1,4-di-oligo(ethylene glycol)benzene; 4-tert-butyl-1,2-di-oligo(ethylene glycol)benzene; 4,5-di-tert-butyl-1,2-di-oligo(ethylene glycol)benzene; 4,5-di-tert-pentyl-1,2-di-oligo(ethylene glycol)benzene; 4,5-di-tert-butyl-1,2-diethoxybenzene; 9,10-di-oligo(ethylene glycol)-1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydroanthracene; 9,10-di-oligo(ethylene glycol)-1,4:5,8-diethano-1,2,3,4,5,6,7,8-octahydroanthracene; 1,4-bis(2-(2-methoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; 1,4-bis(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; or 1,4-bis(2-(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene. 21. The electrochemical device of claim 11, wherein the compound is 1,4-bis(2-(2-methoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; 1,4-bis(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene; or 1,4-bis(2-(2-(2-(2-methoxy)ethoxy)ethoxy)ethoxy)ethoxy-2,5-di-tert-butyl-benzene.
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