Polymeric fluorescent substance and polymer light-emitting device
AssigneeSumitomo Chemical Company, Limited
InventorsMasato Ueda, Takanobu Noguchi
Life of this patent
Estimating the term…
Abstract
Provided is a polymeric fluorescent substance showing fluorescence in solid state, which has a specific carrier drift mobility, a specific repeating unit, and specific number-average molecular weight. The polymeric fluorescent substance is excellent in solubility to organic solvents, and has higher efficiency and longer lifetime in applying as a polymer LED.
Claims12
A polymer fluorescent substance which emits fluorescence in solid state, has a number-average molecular weight in terms of polystyrene of 1×104 to 1×108, and has each of the repeating units represented by repeating units of the formulae (2), (3) and (4):
- wherein in the formula (2), Ar2 is an arylene group having 6 to 60 carbon atoms contained in the main chain portion or a divalent heterocyclic compound group having 3 to 60 carbon atoms contained in the main chain portion, X represents an oxygen atom or sulfur atom, R3 represents a group selected from the group consisting of linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, mono, di or trialkylsilyl groups having 1 to 60 carbon atoms, aryl groups having 6 to 60 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms and heterocyclic compound groups having 3 to 60 carbon atoms, and the aryl group, arylalkyl group and heterocyclic group may also have a substituent, the symbol k is an integer from 1 to 4, each of R4 and R5 independently represents a group selected from the group consisting of a hydrogen atom, linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 60 carbon atoms, heterocyclic compound groups having 3 to 60 carbon atoms and a cyano group, and the aryl group and heterocyclic group may also have a substituent, the symbol m is 0 or 1, Ar2 may have a substituent selected from the group consisting of linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, mono, di or trialkylsilyl groups having 1 to 60 carbon atoms, mono or dialkylamino groups having 1 to 40 carbon atoms, aryl groups having 6 to 60 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms, arylamino groups having 6 to 60 carbon atoms, heterocyclic compound groups having 3 to 60 carbon atoms and a cyano group, and the aryl group, arylalkyl group, arylamino group and heterocyclic group may further have a substituent, substituents may be the same or different when Ar2 has a plurality of substituents, one or more carbon atoms of the substituent on Ar2 may be substituted with an oxygen atom or sulfur atom, and one or more hydrogen atoms of the substituent on Ar2 may be substituted with a fluorine atom,
- when in the formula (3), Ar3 is an arylene group having 6 to 60 carbon atoms contained in the main chain portion or a heterocyclic compound group having 3 to 60 carbon atoms contained in the main chain portion, Ar4 is an aryl group having 6 to 60 carbon atoms or a heterocyclic compound group having 3 to 60 carbon atoms, and may also have a substituent selected from the group consisting of linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, alkoxy groups having a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, alkylthio groups having a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, mono, di or trialkylsilyl groups having 1 to 60 carbon atoms, mono or dialkylamino groups having 1 to 40 carbon atoms, aryl groups having 6 to 60 carbon atoms, aryloxy groups having 6 to 60 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms, arylalkoxy groups having 7 to 60 carbon atoms, arylalkenyl groups having 8 to 60 carbon atoms, arylalkynyl groups having 8 to 60 carbon atoms, arylamino groups having 6 to 60 carbon atoms, heterocyclic compound groups having 3 to 60 carbon atoms and a cyano group, and the aryl group, aryloxy group, arylalkyl group, arylalkoxy group, arylalkenyl group, arylalkynyl group, arylamino group and heterocyclic group may further have a substituent, the symbol n is an integer from 1 to 4, each of R6 and R7 independently represents a group selected from the group consisting of a hydrogen atom, linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 60 carbon atoms, heterocyclic compound groups having 3 to 60 carbon atoms and a cyano group, and the aryl group and heterocyclic group may also have a substituent, the symbol p is 0 or 1, Ar3 may have a substituent selected from the group consisting of linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, alkoxy groups having a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, alkylthio groups having a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, mono, di or trialkylsilyl groups having 1 to 60 carbon atoms, mono or dialkylamino groups having 1 to 40 carbon atoms, aryloxy groups having 6 to 60 carbon atoms, arylalkyl groups having 7 to 60 carbon atoms, arylalkoxy groups having 7 to 60 carbon atoms, arylamino groups having 6 to 60 carbon atoms, and a cyano group, and the aryloxy group, arylalkyl group, arylalkoxy group, arylamino group may further have a substituent, substituents may be the same or different when Ar3 has a plurality of substituents, one or more carbon atoms of the substituents on Ar3 may be substituted with an oxygen atom or sulfur atom, and one or more hydrogen atoms of the substituents on Ar3 maybe substituted with a fluorine atom,
- wherein in the formula (4), Ar5 is an arylene group having 6 to 60 carbon atoms contained in the main chain portion or a divalent heterocyclic compound group having 3 to 60 carbon atoms contained in the main chain portion, R8 represents a group selected from the group consisting of linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, mono, di or trialkylsilyl groups having 1 to 60 carbon atoms, mono or dialkylamino groups having 1 to 40 carbon atoms, saturated heterocyclic compound groups having 3 to 60 carbon atoms and arylalkyl groups having 7 to 60 carbon atoms, and the arylalkyl group may further have a substituent, the symbol q is an integer from 1 to 4, each of R9 and R10 independently represents a group selected from the group consisting of a hydrogen atom, linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 60 carbon atoms, heterocyclic compound groups having 3 to 60 carbon atoms and a cyano group, and the aryl group and heterocyclic group may also have a substituent, the symbol r is 0 or 1, Ar5 may have a substituent selected from the group consisting of alkoxy groups having a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, alkylthio groups having a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, aryl groups having 6 to 60 carbon atoms, aryloxy groups having 6 to 60 carbon atoms, arylalkoxy groups having 7 to 60 carbon atoms, arylamino groups having 6 to 60 carbon atoms, heterocyclic compound groups having 3 to 60 carbon atoms and a cyano group, and the aryl group, aryloxy group, arylalkoxy group, arylamino group and heterocyclic group may further have a substituent, substituents may be the same or different when Ar5 has a plurality of substituents, one or more carbon atoms of the substituents on Ar5 may be substituted with an oxygen atom or sulfur atom, and one or more hydrogen atoms of the substituents on Ar5 may be substituted with a fluorine atom, wherein, the total amount of repeating units of the formulae (2), (3) and (4) is 50 mol % or more based on all repeating units, and the amount of repeating units of formula (2) is 0.1 mol % to 30 mol %, the amount of repeating units of formula (3) is 29.9 mol % to 70 mol % and the amount of repeating units of formula (4) is 29.9 mol % to 70 mol %, based on the total amount of repeating units of the formulae (2), (3) and (4).
Dependencies are inferred from the claim text.