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 . 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 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 ; 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 organic device described in  claim 18 , wherein in formula (1),
 each of ring A, ring B and ring C each 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 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 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 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 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 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 ; 
 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 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 organic device described in  claim 18 , wherein the halogen atom is a fluorine atom. 
     
     
         23 . The 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 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 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 organic device described in  claim 18 , which is an organic electroluminescent element, an organic field effect transistor, or an organic thin film solar cell. 
     
     
         27 . An organic electroluminescent element described in  claim 26 , comprising a pair of electrodes composed of a positive electrode and a negative electrode; and a light emitting layer that is disposed between the pair of electrodes and contains the polycyclic aromatic compound represented by the following general formula (1) or the oligomer thereof described in claim  1  as a material for the light emitting layer. 
     
     
         28 . An organic electroluminescent element described in  claim 26 , comprising a pair of electrodes composed of a positive electrode and a negative electrode; a light emitting layer that is disposed between the pair of electrodes; and an electron injection layer and/or an electron transport layer that is disposed between the negative electrode and the light emitting layer and contains the polycyclic aromatic compound represented by the following general formula (1) or the oligomer thereof described in claim  1  as a material for the electron injection layer or electron transport layer. 
     
     
         29 . An organic electroluminescent element described in  claim 26 , comprising a pair of electrodes composed of a positive electrode and a negative electrode; a light emitting layer that is disposed between the pair of electrodes; and a hole injection layer and/or a hole transport layer that is disposed between the positive electrode and the light emitting layer and contains the polycyclic aromatic compound represented by the following general formula (1) or the oligomer thereof described in claim  1  as a material for the hole injection layer or hole transport layer. 
     
     
         30 . The organic electroluminescent element described in  claim 27 , further comprising an electron transport layer and/or an electron injection layer that is disposed between the negative electrode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of a quinolinol-based metal complex, a pyridine derivative, a phenanthroline derivative, a borane derivative, and a benzimidazole derivative. 
     
     
         31 . The organic electroluminescent element described in  claim 30 , wherein the electron transport layer and/or electron injection layer further contains at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal. 
     
     
         32 . A display apparatus comprising the organic electroluminescent element described in  claim 27 . 
     
     
         33 . A lighting apparatus comprising the organic electroluminescent element described in  claim 27 .