New polymer and polymer light-emitting device using the same

Abstract

Provided is a polymer comprising a repeating unit represented by formula (1), wherein, A 1 represents a divalent group in which the bond distance ratio (bond distance of C(α)-A 1 /bond distance of C(α)-C(β)) is 1.10 or more; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 , each independently represent a hydrogen atom, alkyl group, alkyloxy group, aryloxy group, arylalkyloxy group, etc. The polymer is useful as a light-emitting material, a charge transporting material, etc.

What is claimed is:  
     
         1 . A polymer having a polystyrene reduced number average molecular weights of 10 3 -10 8 , and comprising a repeating unit represented by formula (1),  
       
         
           
           
               
               
           
         
       
       wherein, A 1  is a divalent group represented by -Z- or -Z-Z-, in which Z is an atomic group which may have a substituent; A 1  represents a divalent group in which the bond distance ratio (bond distance C2-A 1 /bond distance C2-C1) is 1.10 or more, in which C2 is the carbon of α position, and C1 is the carbon of β position, respectively to A 1 ; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 , each independently represent a hydrogen atom, a halogen atom, an alkyl group, alkenyl group, alkynyl group, alkyloxy group, alkylthio group, an alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, arylalkylamino group, substituted silyl group, acyl group, acyloxy group, imino group, amide group, arylalkenyl group, arylalkynyl group, monovalent heterocyclic group, or cyano group; R 2  and R 3  may be connected to form a ring; and R 4  and R 5  may be connected to form a ring.  
     
     
         2 . A polymer according to  claim 1 , wherein the atom in the atomic group Z includes Si, P, S, Ge, Sn, Se, or Te.  
     
     
         3 . A polymer according to  claim 1 , wherein A 1  is a divalent group represented by formula (4), (5) or (6),  
       
         
           
           
               
               
           
         
       
       wherein, R 7  represents an alkyl group, alkyloxy group, alkylthio group, alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkyl amino group, acyl group, acyloxy group, amide group, or monovalent heterocyclic group,  
       —S—S—  (5)                    
       wherein, A 2  represents Si, Ge, or Sn; R 8  and R 9  each independently represent an alkyl group, alkyloxy group, alkylthio group, alkylamino group, aryl group, aryloxy group, arylthio group, arylamino group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkylamino group, acyloxy group, amide group, or monovalent heterocyclic group; and l represents 1 or 2.  
     
     
         4 . A polymer according to  claim 3 , wherein A 1  is a divalent group represented by the above formula (4).  
     
     
         5 . A polymer according to  claim 3 , wherein A 1  is a divalent group represented by the above formula (5).  
     
     
         6 . A polymer according to  claim 3 , wherein A 1  is a divalent group represented by the above formula (6), in which A 2  is Si, and l is 1.  
     
     
         7 . A polymer according to  claim 3 , wherein A 1  is a divalent group represented by formula (6), in which A 2  is Si, and l is 2.  
     
     
         8 . A polymer according to  claim 1 , wherein R 2  and R 5  each independently represent an alkyloxy group, alkylthio group, alkylamino group, aryloxy group, arylthio group, arylamino group, arylalkyloxy group, arylalkylthio group, or arylalkylamino group.  
     
     
         9 . A polymer according to  claim 8 , wherein R 2  and R 5  each independently represent alkyloxy group, aryloxy group, or arylalkyloxy group.  
     
     
         10 . A polymer according to  claim 1 , wherein said polymer further comprises a repeating unit represented the below formula (7),  
       —Ar 6 —(CR 17 ═CR 18 ) n -  (7)  
       wherein, Ar 6  represents an arylene group or a divalent heterocyclic group; R 17  and R 18  each independently represent a hydrogen atom, an alkyl group, aryl group, monovalent heterocyclic group, or cyano group; and n represents 0 or 1.  
     
     
         11 . A polymer according to  claim 1 , wherein said polymer further comprises a repeating unit represented by the below formula (8),  
       
         
           
           
               
               
           
         
       
       wherein, Ar 1  and Ar 2  each independently represent an arylene group or a divalent heterocyclic group; R 11  represents a group represented by an alkyl group, aryl group, monovalent heterocyclic group, and a group represented by the below formula (9) or (10); and m represents an integer of 1-4,  
       —Ar 3 Y 1  p R 12   (9)  
       wherein, Ar 3  represents an arylene group or a divalent heterocyclic group; R 12  represents a hydrogen atom, an alkyl group, aryl group, monovalent heterocyclic group, or a group represented by the below formula (10); Y1 represents —CR 3 ═CR 14 —, or —C≡C—; R 13  and R 14  each independently represent a hydrogen atom, an alkyl group, aryl group, monovalent heterocyclic group, or cyano group; and p represents an integer of 0-2,  
       
         
           
           
               
               
           
         
       
       wherein, Ar 4  and Ar 5  each independently represent an arylene group or a divalent heterocyclic group; R 15  represents an alkyl group, aryl group, or monovalent heterocyclic group; R 16  represents a hydrogen atom, an alkyl group, aryl group, or monovalent heterocyclic group; and q represents an integer of 1-4.  
     
     
         12 . A process for producing a polymer according to any one of  claims 1  to  11 , wherein condensation polymerization is carried out using a compound represented by the below formula (11),  
       
         
           
           
               
               
           
         
       
       wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and A 1  respectively represent the same groups as those in formula (1); x 1  and x 2  each independently represent a substituent capable of condensation polymerization.  
     
     
         13 . A compound represented by formula (11),  
       
         
           
           
               
               
           
         
       
       wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and A 1  respectively represent the same groups as those in formula (1); x 1  and x 2  each independently represent a substituent capable of condensation polymerization.  
     
     
         14 . A compound according to  claim 13 , wherein A 1  is a divalent group represented by the above formula (4).  
     
     
         15 . A compound according to  claim 13 , wherein A 1  is a divalent group represented by the above formula (5).  
     
     
         16 . A compound according to  claim 13 , wherein A 1  is a divalent group represented by the above formula (6), in which A 2  is Si, and l is 1.  
     
     
         17 . A compound according to  claim 13 , wherein A 1  is a divalent group represented by the above formula (6), in which A 2  is Si, and l is 2.  
     
     
         18 . A compound according to  claim 13 , wherein R 2  and R 5  each independently represent an alkyloxy group, alkylthio group, alkylamino group, aryloxy group, arylthio group, arylamino group, arylalkyloxy group, arylalkylthio group, or arylalkylamino group.  
     
     
         19 . A compound according to  claim 18 ,wherein R 2  and R 5  each independently represent an alkyloxy group, aryloxy group, or arylalkyloxy group.  
     
     
         20 . A compound according to  claim 13 , wherein x 1  and x 2  each independently represent a halogen atom, alkyl sulfonate group, aryl sulfonate group, or arylalkyl sulfonate group.  
     
     
         21 . A compound according to  claim 13 , wherein x 1  and x 2  each independently represent a halogen atom.  
     
     
         22 . A process for producing a polymer according to  claim 12 , wherein condensation polymerization of the compound recited in claims  20  or  21  is carried out using a palladium catalyst or a nickel catalyst.  
     
     
         23 . A process for producing a compound according to any one of claims  14  or  18  to  21 , wherein two iodine atoms in the compound represented by the below formula (13) are selectively metalated, and then reacted with a dihalogenated phosphorous compound represented by the below formula (14),  
       
         
           
           
               
               
           
         
       
       wherein, R 1 , R 2 , R 3 , R 4 , R 5  and R 6  respectively represent the same groups as those in formula (1); x 1  and x 2  respectively represent the same groups as those in formula (11),  
       
         
           
           
               
               
           
         
       
       wherein, R 7  represents the same groups as those in formula (4); x5 and x6 each independently represent a chlorine atom, bromine atom, or iodine atom.  
     
     
         24 . A process for producing a compound according to any one of claims  15  or  18  to  21 , wherein two iodine atoms of the compound represented by the below formula (13) is selectively metalated, and then reacted with sulfur.  
     
     
         25 . A process for producing a compound according to  claim 16 , wherein the compound represented by the below formula (19) is reacted with a halogenation reagent,  
       
         
           
           
               
               
           
         
       
       wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6  respectively represent the same groups as those in formula (1); R 8 , and R 9  respectively represent the same groups as those in formula (6).  
     
     
         26 . A process for producing a dibenzosilole derivative according to  claim 25 , wherein N-halogeno compound is used as the halogenation reagent.  
     
     
         27 . A dibenzosilole derivative represented by the above formula (19).  
     
     
         28 . A dibenzosilole derivative according to  claim 27 , wherein all of R 1 , R 3 , R 4 , and R 6  in the above formula (19) are hydrogen atoms.  
     
     
         29 . A process for producing a disilyl compound according to any one of  claims 17  to  21 , wherein two iodine atoms in the compound represented by the above formula (13) are selectively metalated, and then reacted with a dihalogenated disilyl compound represented by the below formula (22),  
       
         
           
           
               
               
           
         
       
       wherein, R 8  and R 9  represent respectively represent the same groups as those in formula (6); x11 and x12 each independently represent a chlorine atom, bromine atom, or iodine atom.  
     
     
         30 . A polymer electronic device including a polymer according to any one of  claims 1  to  11 .  
     
     
         31 . A polymeric fluorescent substance consisting of a polymer according to any one of  claims 1  to  11 .  
     
     
         32 . A polymer light-emitting device having a light emitting layer between the electrodes consisting of an anode and a cathode, wherein said light-emitting layer contains the polymer according to any one of  claims 1  to  11 .  
     
     
         33 . A flat light source comprising a polymer light-emitting device according to  claim 32 .  
     
     
         34 . A segment display apparatus comprising a polymer light-emitting device according to  claim 32 .  
     
     
         35 . A dot-matrix display apparatus comprising a polymer light-emitting device according to  claim 32 .  
     
     
         36 . A liquid crystal display comprising a polymer light-emitting device according to  claim 32  as a back light.