Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device

Abstract

A compound represented by formula (1): wherein R 1 to R 6 , R 7 to R 10 , R 11 to R 14 , R 15 to R 18 , L 1 , L 2 , Ar 1 , and Ar 2 are as defined in the description realizes an organic electroluminescence device with long lifetime.

1 : A compound represented by formula (1): 
       
         
           
           
               
               
           
         
       
       wherein:
 each of R 1  to R 6  is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, or a cyano group; 
 one of R 7  to R 10  is a single bond bonded to *a, and each of the others of R 7  to R 10  is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, or a cyano group; 
 one of R 11  to R 14  is a single bond bonded to *b, and each of the others of R 11  to R 14  is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, or a cyano group; 
 each of R 15  to R 18  is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, or a cyano group; 
 each of L 1  and L 2  is independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 ring atoms; and 
 each of Ar 1  and Ar 2  is independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; 
 provided that at least one selected from Ar 1  and Ar 2  is a substituted or unsubstituted fluoranthenyl group. 
 
     
     
         2 : The compound according to  claim 1 , wherein the compound is represented by formula (2): 
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 7 , R 9  to R 12 , R 14  to R 18 , L 1 , L 2 , Ar 1 , and Ar 2  are the same as defined above. 
     
     
         3 : The compound according to  claim 1 , wherein the compound is represented by formula (3): 
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 7 , R 9  to R 11 , R 13  to R 18 , L 1 , L 2 , Ar 1 , and Ar 2  are the same as defined above. 
     
     
         4 : The compound according to  claim 1 , wherein the compound is represented by formula (4): 
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 8 , R 10  to R 12 , R 14  to R 18 , L 1 , L 2 , Ar 1 , and Ar 2  are the same as defined above. 
     
     
         5 : The compound according to  claim 1 , wherein the compound is represented by formula (5): 
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 8 , R 10 , R 11 , R 13  to R 18 , L 1 , L 2 , Ar 1 , and Ar 2  are the same as defined above. 
     
     
         6 : The compound according to  claim 1 , wherein:
 the an alkyl group having 1 to 20 carbon atoms in the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms for R 1  to R 18  is selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a pentyl group (inclusive of isomeric groups), a hexyl group (inclusive of isomeric groups), a heptyl group (inclusive of isomeric groups), an octyl group (inclusive of isomeric groups), a nonyl group (inclusive of isomeric groups), a decyl group (inclusive of isomeric groups), an undecyl group (inclusive of isomeric groups), and a dodecyl group (inclusive of isomeric groups);   the cycloalkyl group having 3 to 10 ring carbon atoms in the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms for R 1  to R 18  is selected from the group consisting of a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group;   the aryl group having 6 to 18 ring carbon atoms in the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms for R 1  to R 18  is selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a triphenylenyl group, a phenalenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a s-indanyl group, an as-indanyl group, and a fluoranthenyl group;   the haloalkyl group having 1 to 20 carbon atoms in the substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms for R 1  to R 18  is selected from the group consisting of a heptafluoropropyl group (inclusive of isomeric groups), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group;   the alkoxy group having 1 to 20 carbon atoms in the substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms for R 1  to R 18  is selected from the group consisting of a t-butoxy group, a propoxy group (inclusive of isomeric groups), an ethoxy group, and a methoxy group;   the haloalkoxy group having 1 to 20 carbon atoms in the substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms for R 1  to R 18  is selected from the group consisting of a heptafluoropropoxy group (inclusive of isomeric groups), a pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group, and a trifluoromethoxy group;   the aryloxy group having 6 to 18 ring carbon atoms in the substituted or unsubstituted aryloxy group having 6 to 18 ring carbon atoms for R 1  to R 18  comprises an aryl group selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a triphenylenyl group, a phenalenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a s-indanyl group, an as-indanyl group, and a fluoranthenyl group;   the halogen atom for R 1  to R 18  is selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;   the arylene group having 6 to 18 ring carbon atoms in the substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms for L 1  and L 2  is a group obtained by removing one hydrogen atom from an aryl group selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a triphenylenyl group, a phenalenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a s-indanyl group, an as-indanyl group, and a fluoranthenyl group;   the heteroarylene group having 5 to 18 ring atoms in the substituted or unsubstituted heteroarylene group having 5 to 18 ring atoms for L 1  and L 2  is a group obtained by removing one hydrogen atom from a heteroaryl group selected from the group consisting of a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzotiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazoly group, a benzisothiazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzotiophenyl group, a naphthobenzotiophenyl group, a carbazolyl group, a benzocarbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, and a xanthenyl group; and   the aryl group having 6 to 18 ring carbon atoms in the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms for Ar 1  and Ar 2  is selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a triphenylenyl group, a phenalenyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a s-indanyl group, an as-indanyl group, and a fluoranthenyl group.   
     
     
         7 : The compound according to  claim 1 , wherein each of adjacent two groups selected from R 1  to R 6 , adjacent two groups selected from R 7  to R 10 , adjacent two groups selected from R 11  to R 14 , and adjacent two groups selected from R 15  to R 18  may be respectively bonded to each other to from a substituted or unsubstituted ring. 
     
     
         8 : The compound according to  claim 1 , wherein adjacent two groups selected from R 1  to R 6 , R 7  to R 10 , R 11  to R 14 , and R 15  to R 18  do not form a ring. 
     
     
         9 : The compound according to  claim 1 , wherein R 1  to R 6 , R 7  to R 10  which is not a single bond bonded to *a, R 11  to R 14  which is not a single bond bonded to *b, and R 15  to R 18  are all hydrogen atoms. 
     
     
         10 : The compound according to  claim 1 , wherein L 1  is a single bond and L 2  is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 18 ring atoms. 
     
     
         11 : The compound according to  claim 1 , wherein L 2  is a single bond and L 1  is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 18 ring atoms. 
     
     
         12 : The compound according to  claim 1 , wherein each of L 1  and L 2  is independently a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 18 ring atoms. 
     
     
         13 : The compound according to  claim 10 , wherein the arylene group in the substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms is selected from the group consisting of a phenylene group, a naphthylene group, and a biphenylylene group. 
     
     
         14 : The compound according to  claim 1 , wherein each of L 1  and L 2  is a single bond. 
     
     
         15 : The compound according to  claim 1 , wherein Ar 1  is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms and Ar 2  is a substituted or unsubstituted fluoranthenyl group. 
     
     
         16 : The compound according to  claim 1 , wherein Ar 2  is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms and Ar 1  is a substituted or unsubstituted fluoranthenyl group. 
     
     
         17 : The compound according to  claim 15 , wherein the aryl group having 6 to 18 ring carbon atoms in the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms is selected from the group consisting of a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, and a triphenylenyl group. 
     
     
         18 : The compound according to  claim 1 , wherein the substituted or unsubstituted fluoranthenyl group is a substituted or unsubstituted 1-fluoranthenyl group, a substituted or unsubstituted 3-fluoranthenyl group, a substituted or unsubstituted 7-fluoranthenyl group, or a substituted or unsubstituted 8-fluoranthenyl group. 
     
     
         19 : The compound according to  claim 1 , wherein an optional substituent referred to by “substituted or unsubstituted” is at least one group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, an aralkyl group having 7 to 30 carbon atoms comprising an aryl group having 6 to 18 ring carbon atoms, an aryl group having 6 to 18 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a mono-, di-, or tri-substituted silyl group, wherein the substituent is selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 18 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, a halogen atom, a cyano group, and a nitro group. 
     
     
         20 : A material for organic electroluminescence devices comprising the compound according to  claim 1 . 
     
     
         21 : An organic electroluminescence device comprising a cathode, an anode, and an organic thin film layer between the cathode and the anode, wherein the organic thin film layer comprises one or more layers, the organic thin film layer comprises a light emitting layer, and at least one layer of the organic thin film layer comprises the compound according to  claim 1 . 
     
     
         22 : The organic electroluminescence device according to  claim 21 ,
 wherein the light emitting layer comprises a host material and the host material is the compound.   
     
     
         23 : The organic electroluminescence device according to  claim 21 , wherein the light emitting layer comprises a dopant material and the dopant material is a phosphorescent emitting material. 
     
     
         24 : The organic electroluminescence device according to  claim 23 , wherein the phosphorescent emitting material is an ortho metallated complex of a metal atom selected from the group consisting of iridium, osmium, ruthenium, and platinum. 
     
     
         25 : An electronic device comprising the organic electroluminescence device according to  claim 21 .