Organic electronic material, polymerization initiator and thermal polymerization initiator, ink composition, organic thin film and production method for same, organic electronic element, organic electroluminescent element, lighting device, display element, and display device

Abstract

Disclosed is an organic electronic material comprising charge transporting compounds and ionic compounds having electron-accepting properties and high solubility in a solvent. The organic electronic material is characterized by comprising charge transporting compounds and ionic compounds, and in that at least one of the ionic compounds is any one kind of compounds represented by general formulas (1b)-(3b). (In the formulas Y 1 -Y 6 each independently represent a divalent linking group, R 1 -R 6 each independently represent an electron-attracting organic substituent (these structures can further have substituents and hetero-atoms, and R 1 , R 2 and R 3 , or, R 4 -R 6 can respectively combine and become a ring shape or a polymer shape) and L represents a monovalent cation.)

1 . An organic electronic material comprising a charge transporting compound and an ionic compound, the ionic compound being any one of compounds represented by the following formulas (1b) to (3b): 
       
         
           
           
               
               
           
         
       
       wherein Y 1  to Y 6  each independently represent a divalent linking group; R 1  to R 6  each independently represent an electron-withdrawing organic substituent (this substituent may further have a substituent or a heteroatom in the structure, and R 1 , R 2  and R 3 , or R 4  to R 6  may be respectively joined to form a ring form or a polymer form); and L +  represents a monovalent cation. 
     
     
         2 . The organic electronic material according to  claim 1 , wherein the ionic compound has a halogen atom. 
     
     
         3 . The organic electronic material according to  claim 1 , wherein the ionic compound gas one selected from the group consisting of a perfluoroalkyl group, a perfluoroalkylsulfonyl group, a perfluoroalkyloxysulfonyl group, a perfluoroarylsulfonyl group, a perfluoroaryloxysulfonyl group, a perfluoroacyl group, a perfluoroalkoxycarbonyl group, a perfluoroacyloxy group, a perfluoroaryloxycarbonyl group, a perfluoroalkenyl group and a perfluoroalkynyl group, each of which may be linear chain, branched or cyclic, with 1 to 20 carbon atoms, and may contain a heteroatom. 
     
     
         4 . The organic electronic material according to  claim 1 , wherein Y 1  to Y 6  each represent any one of the following formulas (4b) to (14b): 
       
         
           
           
               
               
           
         
       
       wherein R represents an arbitrary organic group (the organic group may further have a substituent or a heteroatom in the structure). 
     
     
         5 . The organic electronic material according to  claim 1 , wherein L in the formulas (1b) to (3b) is any one of cations represented by the following formulas (15b) to (17b): 
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 34  each independently represent an arbitrary organic group, and any two or more adjacent groups among R 11  to R 34  may be joined to each other and form a ring; A 1  represents an element which belongs to Group 17 or Group 14 of the long form periodic table; A 2  represents an element which belongs to Group 16 or Group 14 of the long form periodic table; and A 3  represents an element which belong to Group 15 of the long form periodic table. 
     
     
         6 . The organic electronic material according to  claim 5 , wherein R 11  to R 34  in the formulas (15b) to (17b) each independently represent an alkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group or an aromatic heterocyclic group, all of which may be substituted. 
     
     
         7 . The organic electronic material according to  claim 5 , wherein A 1  in the formula (15b) is a bromine atom, an iodine atom or a carbon atom; A 2  in the formula (16b) is an oxygen atom, a carbon atom, a sulfur atom or a selenium atom; and A 3  in the formula (17b) is a nitrogen atom, a phosphorus atom, an arsenic atom or an antimony atom. 
     
     
         8 . The organic electronic material according to  claim 1 , wherein the charge transporting compound includes at least one of an aromatic amine, a carbazole and a thiophene compound. 
     
     
         9 . The organic electronic material according to  claim 8 , wherein the aromatic amine, carbazole or thiophene compound is a polymer or an oligomer. 
     
     
         10 . The organic electronic material according to  claim 9 , wherein the number average molecular weight of the polymer or the oligomer is from 1,000 to 100,000. 
     
     
         11 . The organic electronic material according to  claim 9 , wherein the polymer or the oligomer has at least one polymerizable substituent. 
     
     
         12 . The organic electronic material according to  claim 11 , wherein the polymerizable substituent is any one of an oxetane group, an epoxy group, a vinyl group, a vinyl ether group, an acrylate group and a methacrylate group. 
     
     
         13 . The organic electronic material according to  claim 1 , wherein the ionic compound functions as a polymerization initiator. 
     
     
         14 . A polymerization initiator comprising at least one of ionic compounds represented by the following formulas (1b) to (3b): 
       
         
           
           
               
               
           
         
       
       wherein Y 1  to Y 6  each independently represent a divalent linking group; R 1  to R 6  each independently represent an electron-withdrawing organic substituent (the substituent may further have a substituent or a heteroatom in the structure, and R 1 , R 2  and R 3 , or R 4  to R 6  may be respectively joined to form a ring form or a polymer form); and L represents a monovalent cation. 
     
     
         15 . A thermal polymerization initiator comprising at least one of ionic compounds represented by the following formulas (1b) to (3b): 
       
         
           
           
               
               
           
         
       
       wherein Y 1  to Y 6  each independently represent a divalent linking group; R 1  to R 6  each independently represent an electron-withdrawing organic substituent (the substituent may further have a substituent or a heteroatom in the structure, and R 1 , R 2  and R 3 , or R 4  to R 6  may be respectively joined to form a ring form or a polymer form); and L represents a monovalent cation. 
     
     
         16 . An ink composition comprising the organic electronic material according to  claim 1 , and a solvent. 
     
     
         17 . An organic thin film formed by using the organic electronic material according to  claim 1 . 
     
     
         18 . An organic thin film formed by using the ink composition according to  claim 16 . 
     
     
         19 . An electronic element comprising the organic thin film according to  claim 17 . 
     
     
         20 . An organic electroluminescent element comprising the organic thin film according to  claim 17 . 
     
     
         21 . The organic electroluminescent element according to  claim 20 , wherein the organic thin film is a hole injection layer. 
     
     
         22 . The organic electroluminescent element according to  claim 21 , wherein the organic thin film is a hole transport layer. 
     
     
         23 . The organic electroluminescent element according to  claim 20 , wherein the substrate is a flexible substrate. 
     
     
         24 . The organic electroluminescent element according to  claim 20 , wherein the substrate is a resin film. 
     
     
         25 . A display element comprising the organic electroluminescent element according to  claim 20 . 
     
     
         26 . A lighting device comprising the organic electroluminescent element according to  claim 20 . 
     
     
         27 . A display device comprising the lighting device according to  claim 26 , and a liquid crystal element as a display unit.