US2007020526A1PendingUtilityA1

Polymers with low band gaps and high charge mobility

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Assignee: GAUDIANA RUSSELLPriority: Jul 14, 2005Filed: Jul 14, 2006Published: Jan 25, 2007
Est. expiryJul 14, 2025(expired)· nominal 20-yr term from priority
Inventors:Russell GaudianaRichard KingsboroughXiaobo ShiDavid P. WallerZhengguo Zhu
H10K 30/50H10K 85/151C08G 61/124C08G 61/126Y02E10/549B82Y 10/00C08G 61/123C08G 61/02H10K 85/113H10K 85/215H10K 30/30
53
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Claims

Abstract

Polymers with low band gaps and high charge mobility, as well as related systems, methods and components are disclosed.

Claims

exact text as granted — not AI-modified
1 . A photovoltaic cell, comprising: 
 a first electrode,    a second electrode, and    a photoactive material disposed between the first and second electrodes, the photoactive material comprising a polymer including a first comonomer repeat unit and a second comonomer repeat unit, wherein the first comonomer repeat unit comprises a cyclopentadithiophene moiety, and the second comonomer repeat unit comprises a silole moiety.    
     
     
         2 . The photovoltaic cell of  claim 1 , wherein the cyclopentadithiophene moiety is substituted with at least one substituent selected from the group consisting of C l -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, halo, CN, NO 2 , and SO 2 R, in which R is H, C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, or C 3 -C 20  heterocycloalkyl.  
     
     
         3 . The photovoltaic cell of  claim 2 , wherein the substituent is hexyl, ethylhexyl, or C 1 -C 20  alkoxy optionally further substituted with C 1 -C 20  alkoxy or halo.  
     
     
         4 . The photovoltaic cell of  claim 2 , wherein the substitutent is hexyl, ethylhexyl, or (OCH 2 CH 2 ) 2 OCH 3  or OCH 2 CF 2 OCF 2 CF 2 OCF 3 .  
     
     
         5 . The photovoltaic cell of  claim 1 , wherein the first comonomer repeat unit comprises a cyclopentadithiophene moiety of formula (I):  
       
         
           
           
               
               
           
         
       
       wherein each of R 1 , R 2 , R 3 , and R4, independently, is H, C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, halo, CN, NO 2 , or SO 2 R, in which R is C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, or C 3 -C 20  heterocycloalkyl.  
     
     
         6 . The photovoltaic cell of  claim 5 , wherein at least one of R 1  and R 2  is hexyl, ethylhexyl, or C 1 -C 20  alkoxy optionally further substituted with C 1 -C 20  alkoxy or halo.  
     
     
         7 . The photovoltaic cell of  claim 5 , wherein at least one of R 1  and R 2  is hexyl, ethylhexyl, or (OCH 2 CH 2 ) 2 OCH 3  or OCH 2 CF 2 OCF 2 CF 2 OCF 3 .  
     
     
         8 . The photovoltaic cell of  claim 1 , wherein the silole moiety is substituted with at least one substituent selected from the group consisting of C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, halo, CN, NO 2 , and SO 2 R, in which R is H, C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, or C 3 -C 20  heterocycloalkyl.  
     
     
         9 . The photovoltaic cell of  claim 8 , wherein the substituent is C 1 -C 20  alkyl or aryl.  
     
     
         10 . The photovoltaic cell of  claim 1 , wherein the second monomer repeat unit comprises a silole moiety of formula (XXI):  
       
         
           
           
               
               
           
         
       
       wherein each of R 5 , R 6 , R 7  and R 8 , independently, is H, C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, halo, CN, NO 2 , or SO 2 R, in which R is C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, or C 3 -C 20  heterocycloalkyl.  
     
     
         11 . The photovoltaic cell of  claim 10 , wherein at least one of R 5 , R 6 , R 7  and R 8  is C 1 -C 20  alkyl optionally substituted with halo, or aryl optionally substituted with C 1 -C 20  alkyl.  
     
     
         12 . The photovoltaic cell of  claim 10 , wherein each of R 5  and R 6 , independently is aryl optionally substituted with C 1 -C 20  alkyl; and each of R 7  and R 8 , independently, is C 1 -C 20  alkyl optionally substituted with halo.  
     
     
         13 . The photovoltaic cell of  claim 1 , wherein the polymer is an electron donor material.  
     
     
         14 . A polymer, comprising a first comonomer repeat unit and a second comonomer repeat unit, wherein the first comonomer repeat unit comprises a cyclopentadithiophene moiety, and the second comonomer repeat unit comprises a silole moiety.  
     
     
         15 . The polymer of  claim 14 , wherein the cyclopentadithiophene moiety is substituted with at least one substituent selected from the group consisting of C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, halo, CN, NO 2 , and SO 2 R, in which R is H, C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20 cycloalkyl, or C   3 -C 20  heterocycloalkyl.  
     
     
         16 . The polymer of  claim 15 , wherein the substituent is hexyl, ethylhexyl, or C 1 -C 20  alkoxy optionally further substituted with C 1 -C 20  alkoxy or halo.  
     
     
         17 . The polymer of  claim 15 , wherein the substitutent is hexyl, ethylhexyl, or (OCH 2 CH 2 ) 2 OCH 3  or OCH 2 CF 2 OCF 2 CF 2 OCF 3 .  
     
     
         18 . The polymer of  claim 14 , wherein the first comonomer repeat unit comprises a cyclopentadithiophene moiety of formula (I):  
       
         
           
           
               
               
           
         
       
       wherein each of R 1  , R 2 , R 3 , and R 4 , independently, is H, C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, halo, CN, NO 2 , or SO 2 R, in which R is C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, or C 3 -C 20  heterocycloalkyl.  
     
     
         19 . The polymer of  claim 18 , wherein at least one of R 1  and R 2  is hexyl, ethylhexyl, or C 1 -C 20  alkoxy optionally further substituted with C 1 -C 20  alkoxy or halo.  
     
     
         20 . The polymer of  claim 18 , wherein at least one of R 1  and R 2  is hexyl, ethylhexyl, or (OCH 2 CH 2 ) 2 OCH 3  or OCH 2 CF 2 OCF 2 CF 2 OCF 3 .  
     
     
         21 . The polymer of  claim 14 , wherein the silole moiety is substituted with at least one substituent selected from the group consisting of C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, halo, CN, NO 2 , and SO 2 R, in which R is H, C 1 -C 20  alkyl, C 1-C   20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, or C 3 -C 20  heterocycloalkyl.  
     
     
         22 . The polymer of  claim 21 , wherein the substituent is C 1 -C 20  alkyl or aryl.  
     
     
         23 . The polymer of  claim 14 , wherein the second monomer repeat unit comprises a silole moiety of formula (XXI):  
       
         
           
           
               
               
           
         
       
       wherein each of R 5 , R 6 , R 7  and R 8 , independently, is H, C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, halo, CN, NO 2 , or SO 2 R, in which R is C 1 -C 20  alkyl, C 1 -C 20  alkoxy, aryl, heteroaryl, C 3 -C 20  cycloalkyl, or C 3 -C 20  heterocycloalkyl.  
     
     
         24 . The polymer of  claim 23 , wherein at least one of R 5 , R 6 , R 7  and R 8  is C 1 -C 20  alkyl optionally substituted with halo, or aryl optionally substituted with C 1 -C 20  alkyl.  
     
     
         25 . The polymer of  claim 23 , wherein each of R 5  and R 6 , independently is aryl optionally substituted with C 1 -C 20  alkyl; and each of R 7  and R 8 , independently, is C 1 -C 20  alkyl optionally substituted with halo.  
     
     
         26 . A device, comprising: 
 a first electrode,    a second electrode, and    a photoactive material disposed between the first and second electrodes, the photoactive material comprising a polymer including a first monomer repeat unit and a second comonomer repeat unit, wherein the first comonomer repeat unit comprises a cyclopentadithiophene moiety and the second comonomer repeat unit comprises a silole moiety.    
     
     
         27 . The device of  claim 26 , wherein the device is an organic semiconductive device.  
     
     
         28 . The device of  claim 26 , wherein the device is a member selected from the group consisting of photovoltaic cells, field effect transistors, photodetectors, photovoltaic detectors, imaging devices, light emitting diodes, lasing devices, conversion layers, amplifiers and emitters, storage elements, and electrochromic devices.

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