Patent EP-2221354-A2 (EP)
Inventor: DOI SHUJI
IPC: C08G61/02
Filed: 2002-04-26
Abstract: The present invention provides a polymeric fluorescent substance showing fluorescence in the solid state, having a polystyrene reduced number-average molecular weight of 10 3  to 10 8 , which comprises one or more repeating units of formula (1):   
wherein R 1 , R 2 , R 3  and R 4  each independently represent a hydrogen atom or a substituent, and at least one of R 1 , R 2 , R 3  and R 4  is a group selected from alkoxy groups, aryl groups substituted with an alkoxy group, aryloxy groups and arylalkoxy groups, 
and one or more repeating units of formula (2):  
 -Ar 1 -(2)  
wherein Ar 1  represents a different group from that of formula (1) and is a group selected from repeating units of formula (7):   
wherein R 11  and R 12  each independently represent a group selected from alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, alkylthio groups having 1 to 20 carbon atoms, alkylsilyl groups having 1 to 60 carbon atoms, alkylamino groups having 1 to 40 carbon atoms, aryl groups having 6 to 60 carbon atoms, aryloxy groups having 6 to 60 carbon atoms, arylsilyl groups having 6 to 60 carbon atoms, arylamino groups having 6 to 60 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms, arylalkoxy groups having 7 to 60 carbon atoms, arylalkylsilyl groups having 7 to 60 carbon atoms, arylalkylamino groups having 7 to 60 carbon atoms, arylalkenyl groups having 8 to 60 carbon atoms, arylalkynyl groups having 8 to 60 carbon atoms, monovalent heterocyclic compound groups having 4 to 60 carbon atoms and cyano group; a and b each independently represent an integer of 0 to 3; when a is 2 or more, a plurality of R 11 s may be the same or different; when b is 2 or more, a plurality of R 12 s may be the same or different; two or more of R 11  to R 12  may be connected to form a ring; and further, when one or more of R 11  to R 12  is a group containing an alkyl chain, one or more of a methyl group, methylene group and methine group constituting the alkyl chain may be substituted with a group containing a hetero atom; 
repeating units of formula (10):   
wherein R 21  represents a group selected from alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, alkylthio groups having 1 to 20 carbon atoms, alkylsilyl groups having 1 to 60 carbon atoms, alkylamino groups having 1 to 40 carbon atoms, aryl groups having 6 to 60 carbon atoms, aryloxy groups having 6 to 60 carbon atoms, arylsilyl groups having 6 to 60 carbon atoms, arylamino groups having 6 to 60 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms, arylalkoxy groups having 7 to 60 carbon atoms, arylalkylsilyl groups having 7 to 60 carbon atoms, arylalkylamino groups having 7 to 60 carbon atoms, arylalkenyl groups having 8 to 60 carbon atoms, arylalkynyl groups having 8 to 60 carbon atoms, monovalent heterocyclic compound groups having 4 to 60 carbon atoms and cyano group; g represents an integer of 0 to 2; when g is 2, a plurality of R 21 s may be the same or different; a plurality of R 21 s may be connected to form a ring; further, when R 21  is a group containing an alkyl chain, one or more of a methyl group, methylene group and methine group constituting the alkyl chain may be substituted with a group containing a hetero atom; and X 1  is selected from O and S; 
repeating units of formula (11):   
wherein R 22  and R 23  each independently represent a group selected from alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, alkylthio groups having 1 to 20 carbon atoms, alkylsilyl groups having 1 to 60 carbon atoms, alkylamino groups having 1 to 40 carbon atoms, aryl groups having 6 to 60 carbon atoms, aryloxy groups having 6 to 60 carbon atoms, arylsilyl groups having 6 to 60 carbon atoms, arylamino groups having 6 to 60 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms, arylalkoxy groups having 7 to 60 carbon atoms, arylalkylsilyl groups having 7 to 60 carbon atoms, arylalkylamino groups having 7 to 60 carbon atoms, arylalkenyl groups having 8 to 60 carbon atoms, arylalkynyl groups having 8 to 60 carbon atoms, monovalent heterocyclic compound groups having 4 to 60 carbon atoms and cyano group; o and p each independently represent an integer of 0 to 4; when o is 2 or more, a plurality of R 22 s may be the same or different; when p is 2 or more, a plurality of R 23 s may be the same or different; two or more of R 22  and R 23  may be connected to form a ring; further, when one or more of R 22  and R 23  is a group containing an alkyl chain, one or more of a methyl group, methylene group and methine group constituting the alkyl chain may be substituted with a group containing a hetero atom; X 2  represents a group selected from O, S, N-R 24  and SiR 25 R 26 ; X 3  and X 4  each independently represent a group selected from N and C-R 27 ; and R 24  to R 27  each independently represent a group selected from a hydrogen atom, alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 60 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms and monovalent heterocyclic compound groups having 4 to 60 carbon atoms; 
and groups of formula (3):  
 -Ar 2 -Ar 3 -Ar 4 -(3)  
wherein Ar 2 , Ar 3  and Ar 4  are groups different from those of formula (1) and each independently represent an arylene group or a divalent heterocyclic compound group, wherein the total amount of repeating units of formula (1) is 10 mol% or more and 90 mol% or less based on the total amount of repeating units of formulae (1) and (2), which exhibits strong fluorescence and/or excellent charge transporting property, and a high performance polymer LED which can be driven at low voltage and high efficiency.