Polycyclic aromatic compound

Abstract

A novel polycyclic aromatic compound in which plural aromatic rings are linked via boron atoms, oxygen atoms and the like is provided, and therefore, the range of selection of the material for organic electroluminescent elements can be widened. Also, an excellent organic electroluminescent element is provided by using the novel polycyclic aromatic compound as a material for an organic electroluminescent element.

1 .- 17 . (canceled) 
     
     
         18 . A material for an organic device comprising a polycyclic aromatic compound represented by the following general formula (1), or an oligomer of a polycyclic aromatic compound having plural structures each represented by the following general formula (1): 
       
         
           
           
               
               
           
         
         wherein in formula (1),
 each of ring A, ring B and ring C independently represents an aryl ring or a heteroaryl ring, while at least one hydrogen atom in these rings may be substituted; 
 Y 1  represents B, P═O, or P═S; 
 when Y 1  represents B, each of X 1  and X 2  independently represents O, N—R, S or Se, wherein R of the moiety N—R represents an aryl which may be substituted, a heteroaryl which may be substituted, or an alkyl which may be substituted, and R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1  or X 2  in the ring A, ring B and/or ring C via —O—, —S—, —C(—R a ) 2 —, or a single bond, wherein R a  represents a hydrogen atom or an alkyl, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y 1 , X 1  and X 2 ; 
 when Y 1  represents P═O or P═S, each of X 1  and X 2  independently represents O, S or Se, one of X 1  and X 2  represents O while the other represents S or Se, one of X 1  and X 2  represents N—R while the other represents Se, or one of X 1  and X 2  represents S while the other represents Se, wherein R of the moiety N—R represents an aryl which may be substituted, a heteroaryl which may be substituted, or an alkyl which may be substituted, and R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1  or X 2  in the ring A, ring B and/or ring C via —O—, —S—, —C(—R a ) 2 —, or a single bond, wherein R 1  represents a hydrogen atom or an alkyl, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y 1 , X 1  and X 2 ; and 
 at least one hydrogen atom in the compound or structure represented by formula (1) may be substituted by a halogen atom or a deuterium atom. 
 
       
     
     
         19 . The material for an organic device described in  claim 18 , wherein in formula (1),
 each of ring A, ring B and ring C independently represents an aryl ring or a heteroaryl ring, while at least one hydrogen atom in these rings may be substituted by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy, or a substituted or unsubstituted aryloxy, and these rings have a 5-membered or 6-membered ring that shares a bond(s) with the fused bicyclic structure at the center of the above formula constructed by Y 1 , X 1  and X 2 ;   Y 1  represents B, P═O, or P═S;   when Y 1  represents B, each of X 1  and X 2  independently represents O, N—R, S or Se, wherein R of the moiety N—R represents an aryl which may be substituted by an alkyl, a heteroaryl which may be substituted by an alkyl, or an alkyl which may be substituted by an alkyl, R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1  or X 2  in the ring A, ring B and/or ring C via —O—, —S—, —C(—R a ) 2 — or a single bond, wherein R 1  represents a hydrogen atom or an alkyl, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y 1 , X 1  and X 2 ;   when Y 1  represents P═O or P═S, each of X 1  and X 2  independently represents O, S or Se, one of X 1  and X 2  represents O while the other represents S or Se, one of X 1  and X 2  represents N—R while the other represents Se, or one of X 1  and X 2  represents S while the other represents Se, wherein R of the moiety N—R represents an aryl which may be substituted by an alkyl, a heteroaryl which may be substituted by an alkyl, or an alkyl which may be substituted by an alkyl, R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1  or X 2  in the ring A, ring B and/or ring C via —O—, —S—, —C(—R a ) 2 — or a single bond, wherein R a  represents a hydrogen atom or an alkyl, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y 1 , X 1  and X 2 ;   at least one hydrogen atom in the compound or structure represented by formula (1) may be substituted by a halogen atom or a deuterium atom; and   the oligomer is a dimer or a trimer, which has two or three of the structure represented by general formula (1).   
     
     
         20 . The material for an organic device described in  claim 18 , wherein the above general formula (1) is represented by the following general formula (2): 
       
         
           
           
               
               
           
         
         wherein in formula (2),
 each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  and R 11  independently represents a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, while at least one hydrogen atom in these may be substituted by an aryl, a heteroaryl or an alkyl, adjacent groups among R 1  to R 11  may be bonded to each other and form an aryl ring or a heteroaryl ring together with the ring a, ring b or ring c, at least one hydrogen atom in the ring thus formed may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, and at least one hydrogen atom in these substituents may be substituted by an aryl, a heteroaryl or an alkyl; 
 Y 1  represents B, P═O, or P═S; 
 when Y 1  represents B, each of X 1  and X 2  independently represents O, N—R, S or Se, wherein R of the moiety N—R represents an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or an alkyl having 1 to 6 carbon atoms, R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1  or X 2  in the ring a, ring b and/or ring c via —O—, —S—, —C(—R a ) 2 — or a single bond, wherein R 11  represents an alkyl having 1 to 6 carbon atoms, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y 1 , X 1  and X 2 ; 
 when Y 1  represents P═O or P═S, each of X 1  and X 2  independently represents O, S or Se, one of X 1  and X 2  represents O while the other represents S or Se, one of X 1  and X 2  represents N—R while the other represents Se, or one of X 1  and X 2  represents S while the other represents Se, wherein R of the moiety N—R represents an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or an alkyl having 1 to 6 carbon atoms, R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1  or X 2  in the ring a, ring b and/or ring c via —O—, —S—, —C(—R a ) 2 — or a single bond, wherein R a  represents an alkyl having 1 to 6 carbon atoms, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y 1 , X 1  and X 2 ; and 
 at least one hydrogen atom in the compound represented by formula (2) may be substituted by a halogen atom or a deuterium atom. 
 
       
     
     
         21 . The material for an organic device described in  claim 20 , wherein in formula (2),
 each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  and R 11  independently represents a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, or a diarylamino (provided that the aryl is an aryl having 6 to 12 carbon atoms), while adjacent groups among R 1  to R 11  are bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the ring a, ring b or ring c, and at least one hydrogen atom in the ring thus formed may be substituted by an aryl having 6 to 10 carbon atoms;   Y 1  represents B, P═O, or P═S;   when Y 1  represents B, each of X 1  and X 2  independently represents O, N—R or S, wherein R in the moiety N—R represents an aryl having 6 to 10 carbon atoms or an alkyl having 1 to 4 carbon atoms;   when Y 1  represents P═O or P═S, each of X 1  and X 2  independently represents O or S, one of X 1  and X 2  represents O while the other represents S, wherein R in the moiety N—R represents an aryl having 6 to 10 carbon atoms or an alkyl having 1 to 4 carbon atoms; and   at least one hydrogen atom in the compound represented by formula (2) may be substituted by a halogen atom or a deuterium atom.   
     
     
         22 . The material for an organic device described in  claim 18 , wherein the halogen atom is a fluorine atom. 
     
     
         23 . The material for an organic device described in  claim 18 , wherein the above formula (1) is represented by the following formula (1-1), the following formula (1-2), the following formula (1-4), the following formula (1-10), the following formula (1-49), the following formula (1-81), the following formula (1-91), the following formula (1-100), the following formula (1-141), the following formula (1-151), the following formula (1-176), the following formula (1-411), the following formula (1-447), the following formula (1-601), or the following formula (1-701): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         24 . The material for an organic device described in  claim 18 , wherein the above formula (1) is represented by the following formula (1-21), the following formula (1-23), the following formula (1-24), the following formula (1-50), the following formula (1-152), the following formula (1-201), the following formula (1-401), the following formula (1-422), the following formula (1-1048), the following formula (1-1049), the following formula (1-1050), the following formula (1-1069), the following formula (1-1084), the following formula (1-1090), the following formula (1-1092), the following formula (1-1101), the following formula (1-1102), the following formula (1-1103), the following formula (1-1145), the following formula (1-1152), the following formula (1-1159), the following formula (1-1187), the following formula (1-1190), the following formula (1-1191), the following formula (1-1192), the following formula (1-1201), the following formula (1-1210), the following formula (1-1247), the following formula (1-1250), the following formula (1-1251), the following formula (1-1252), or the following formula (1-1271): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         25 . The material for an organic device described in  claim 18 , wherein the above formula (1) is represented by the following formula (1-1-1), the following formula (1-79), the following formula (1-142), the following formula (1-152-2), the following formula (1-158), the following formula (1-159), the following formula (1-721), the following formula (1-1006), the following formula (1-1104), the following formula (1-1149), the following formula (1-1150), the following formula (1-1301), the following formula (1-1351), the following formula (1-2305), the following formula (1-2626), the following formula (1-2657), the following formula (1-2662), the following formula (1-2665), the following formula (1-2676), the following formula (1-2678), the following formula (1-2679), the following formula (1-2680), the following formula (1-2681), the following formula (1-2682), the following formula (1-2683), the following formula (1-2691), the following formula (1-2699), the following formula (1-3588), the following formula (1-3654), the following formula (1-3690), the following formula (1-3806), the following formula (1-3824), the following formula (1-4114), the following formula (1-4150), the following formula (1-4341), the following formula (1-4346), the following formula (1-4401), or the following formula (1-4421-1): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         26 . The material for an organic device described in  claim 18 , wherein the material for an organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell. 
     
     
         27 . The material for an organic electroluminescent element described in  claim 26 , which is a material for a light emitting layer. 
     
     
         28 . The material for an organic electroluminescent element described in  claim 26 , which is a material for an electron injection layer or a material for an electron transport layer. 
     
     
         29 . The material for an organic electroluminescent element described in  claim 26 , which is a material for a hole injection layer or a material for a hole transport layer.