Novel soluble compound and organic electroluminescent devices

Abstract

A novel soluble compound which is a distyrylarylene derivative having a soluble substituent and a specific central group and having a solubility of 0.5% by weight or greater at 20° C. in an organic solvent; and an organic electroluminescence device having an organic thin film layer which has a single layer or a plurality of layers, is disposed between a cathode and an anode and has at least one layer containing the novel soluble compound. The organic thin film layer can be formed in accordance with a wet process, and the organic electroluminescence device exhibiting a great efficiency of light emission can be produced easily.

1 . A soluble distyrylarylene derivative represented by general formula (1) and has a solubility (20° C.) of 0.5% by weight or greater in an organic solvent, the general formula (1) being: 
       
         
           
           
               
               
           
         
       
       wherein Ar 1 , Ar 2 , Ar 4  and Ar 5  each independently represent a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted diphenylanthracene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted acenaphthene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted triazole group or a substituted or unsubstituted thiadiazole group;
 R 1  to R 4  each independently represent hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms or cyano group; 
 Ar 3  represents a substituted or unsubstituted anthracendiyl group or a substituted; 
 R 5  to R 8  each independently represent hydrogen atom, a halogen atom, hydroxyl group, a substituted or unsubstituted amino group, nitro group, cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms or carboxyl group, groups represented by R 6  and R 5  or R 7  and R 8  may be bonded to each other and form a cyclic structure which may have substituents; 
 p represents 0 or 1, q represents 0 or 1, m represents 0 or an integer of 1 to 3, and n represents an integer of 1 to 3. 
 
     
     
         2 . A soluble distyrylarylene derivative according to  claim 1 , wherein the organic solvent is at least one solvent selected from toluene, xylene, N-methylpyrrolidone, □-butyrolactone, 1,3-dimethyl-2-imidazoline, carbitol acetate, butylcarbitol acetate, dichloromethane, dichloroethane, chloro-benzene and alcohols having 1 to 10 carbon atoms. 
     
     
         3 . A soluble distyrylarylene derivative according to  claim 1 , wherein Ar 3  represents:
 anthracendiyl group having at least one group selected from:
 (1) linear and branched alkyl groups having 5 or more carbon atoms and an olefinic unsaturated bond, 
 (2) linear, branched and cyclic substituted and unsubstituted alkyl groups having 4 or more carbon atoms, 
 (3) linear, branched and cyclic substituted and unsubstituted alkyloxyl groups having 5 or more carbon atoms, 
 (4) linear, branched and cyclic substituted and unsubstituted alkylthio groups having 5 or more carbon atoms, 
 (5) linear, branched and cyclic substituted and unsubstituted alkylsilyl groups having 5 or more carbon atoms, 
 (6) linear, branched and cyclic substituted and unsubstituted dialkylsilyl groups having 5 or more carbon atoms, 
 (7) linear, branched and cyclic substituted and unsubstituted trialkylsilyl groups having 5 or more carbon atoms, 
 (8) alkylamino groups and dialkylamino groups, 
 (9) linear and branched cyano-substituted alkyl groups having 4 or more carbon atoms and 1 or 2 cyano groups, and 
 (10) polyethers having 2 to 5 ether oxygen atoms which are separated from each other with an alkyl crosslinking having 1 to 3 carbon atoms, or 
   anthracendiyl group having a group selected from aryl groups having 6 to 30 carbon atoms, arylalkyl groups having 7 to 30 carbon atoms, heteroarylalkyl groups having at least one of nitrogen atom, oxygen atom and sulfur atom and 2 to 30 carbon atoms, heterocyclic groups having 2 to 30 carbon atoms, alkanoyl groups having 1 to 20 carbon atoms, cycloalkanoyl groups having 6 to 30 carbon atoms, acryloyl groups having 6 to 30 carbon atoms and heteroaryloxyl groups having at least one of oxygen atom and sulfur atom and 2 to 30 carbon atoms, which are substituted with at least one group selected from aforesaid (1) to (10).   
     
     
         4 . A soluble distyrylarylene derivative according to  claim 1 , wherein at least one of R 5  to R 8  represents:
 at least one group selected from:
 (1) linear and branched alkyl groups having 5 or more carbon atoms and an olefinic unsaturated bond, 
 (2) linear, branched and cyclic substituted and unsubstituted alkyl groups having 4 or more carbon atoms, 
 (3) linear, branched and cyclic substituted and unsubstituted alkyloxyl groups having 5 or more carbon atoms, 
 (4) linear, branched and cyclic substituted and unsubstituted alkylthio groups having 5 or more carbon atoms, 
 (5) linear, branched and cyclic substituted and unsubstituted alkylsilyl groups having 5 or more carbon atoms, 
 (6) linear, branched and cyclic substituted and unsubstituted dialkylsilyl groups having 5 or more carbon atoms, 
 (7) linear, branched and cyclic substituted and unsubstituted trialkylsilyl groups having 5 or more carbon atoms, 
 (8) alkylamino groups and dialkylamino groups, 
 (9) linear and branched cyano-substituted alkyl groups having 4 or more carbon atoms and 1 or 2 cyano groups, and 
 (10) polyethers having 2 to 5 ether oxygen atoms which are separated from each other with an alkyl crosslinking having 1 to 3 carbon atoms, or 
   a group selected from aryl groups having 6 to 30 carbon atoms, arylalkyl groups having 7 to 30 carbon atoms, heteroarylalkyl groups having at least one of nitrogen atom, oxygen atom and sulfur atom and 2 to 30 carbon atoms, heterocyclic groups having 2 to 30 carbon atoms, alkanoyl groups having 1 to 20 carbon atoms, cycloalkanoyl groups having 6 to 30 carbon atoms, acryloyl groups having 6 to 30 carbon atoms and heteroaryloxyl groups having at least one of oxygen atom and sulfur atom and 2 to 30 carbon atoms, which are substituted with at least one group selected from aforesaid (1) to (10).   
     
     
         5 . A soluble according to  claim 1 , wherein Ar 3  represents anthracendiyl group substituted with at least two substituted or unsubstituted t-butyl groups. 
     
     
         6 . An organic electroluminescence device which comprises a cathode, an anode and an organic thin film layer comprising a single layer or a plurality of layers and disposed between the cathode and the anode, wherein at least one layer in the organic thin film layer comprises a soluble distyrylarylene derivative described in  claim 1 . 
     
     
         7 . An organic electroluminescence device which comprises a cathode, an anode and at least a light emitting layer and an electron transporting layer which are disposed between the cathode and the anode, wherein the electron transporting layer comprises a soluble distyrylarylene derivative described in  claim 1 . 
     
     
         8 . An organic electroluminescence device which comprises a cathode, an anode and at least a light emitting layer and a hole transporting layer which are disposed between the cathode and the anode, wherein the hole transporting layer comprises a soluble distyrylarylene derivative described in  claim 1 . 
     
     
         9 . An organic electroluminescence device according to  claim 6 , wherein the organic thin film layer is formed in accordance with a wet process. 
     
     
         10 . An organic electroluminescence device according to  claim 7 , wherein the light emitting layer is formed in accordance with a wet process. 
     
     
         11 . An organic electroluminescence device according to  claim 8 , wherein the light emitting layer is formed in accordance with a wet process. 
     
     
         12 . An organic electroluminescence device according to  claim 7 , wherein the light emitting layer comprises an arylamine compound. 
     
     
         13 . An organic electroluminescence device according to  claim 8 , wherein the light emitting layer comprises an arylamine compound. 
     
     
         14 . An organic electroluminescence device according to  claim 7 , wherein the light emitting layer comprises an aromatic cyclic compound having styryl group. 
     
     
         15 . An organic electroluminescence device according to  claim 8 , wherein the light emitting layer comprises an aromatic cyclic compound having styryl group.