Quinoxaline Derivative, and Light-Emitting Element, Light-Emitting Device, and Electronic Device Using the Same

Abstract

The present invention provides a quinoxaline derivative represented by a general formula (G1). In the formula, α 1 and α 2 each independently represent an arylene group which has 13 or less carbon atoms forming a ring; Ar represents an aryl group which has 13 or less carbon atoms forming a ring; R 1 and R 6 each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group which has 13 or less carbon atoms forming a ring; and R 2 to R 5 and R 7 to R 10 each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

1 - 22 . (canceled) 
     
     
         23 . A quinoxaline derivative represented by a general formula (G1), 
       
         
           
           
               
               
           
         
         wherein: 
         α 1  and α 2  each independently represent an arylene group having 6 to 13 carbon atoms which form an aromatic ring, Ar represents an aryl group having 6 to 13 carbon atoms which form an aromatic ring, 
         R 1  and R 6  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms which form an aromatic ring, 
         R 2  to R 5  and R 7  to R 10  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and 
         a molecular weight of the quinoxaline derivative represented by the general formula (G1) is larger than or equal to 500 and less than or equal to 1357. 
       
     
     
         24 . The quinoxaline derivative according to  claim 23 ,
 wherein α 1  and α 2  in the general formula (G1) each independently represent any of general formulae (2-1) to (2-6) below, and   
       
         
           
           
               
               
           
         
         wherein: 
         R 11  to R 15  and R 21  to R 36  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and 
         R 37  and R 38  each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 
       
     
     
         25 . The quinoxaline derivative according to  claim 23 ,
 wherein Ar in the general formula (G1) is any of general formulae (3-1) to (3-7) below, and   
       
         
           
           
               
               
           
         
         wherein: 
         R 41  to R 45 , R 51  to R 68 , and R 71  to R 79  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a biphenyl group. 
       
     
     
         26 . The quinoxaline derivative according to  claim 23 ,
 wherein R 1  and R 6  in the general formula (G1) each independently represent any of structural formulae (4-1) to (4-6) or general formulae (4-7) to (4-12), and   
       
         
           
           
               
               
           
         
         wherein: 
         R 41  to R 45 , R 51  to R 68 , and R 71  to R 79  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a biphenyl group. 
       
     
     
         27 . The quinoxaline derivative according to  claim 23 ,
 wherein R 2  to R 5  and R 7  to R 10  in the general formula (G1) each independently represent any of structural formulae (5-1) to (5-6) or general formulae (5-7) to (5-10), and   
       
         
           
           
               
               
           
         
         wherein R 41  to R 45 , R 51  to R 68 , and R 71  to R 79  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a biphenyl group. 
       
     
     
         28 . The quinoxaline derivative according to  claim 23 ,
 wherein Ar, R 1 , and R 6  each represent an unsubstituted phenyl group,   wherein α 1  and α 2  each represent a phenylene group, and   wherein R 2  to R 5  and R 7  to R 10  each represent a hydrogen atom.   
     
     
         29 . A light-emitting element comprising:
 a first electrode;   an EL layer over the first electrode; and   a second electrode over the EL layer,   wherein the EL layer comprises a quinoxaline derivative represented by a general formula (G1), and   
       
         
           
           
               
               
           
         
         wherein: 
         α 1  and α 2  each independently represent an arylene group having 6 to 13 carbon atoms which form an aromatic ring, 
         Ar represents an aryl group having 6 to 13 carbon atoms which form an aromatic ring, 
         R 1  and R 6  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms which form an aromatic ring, 
         R 2  to R 5  and R 7  to R 10  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and 
         a molecular weight of the quinoxaline derivative represented by the general formula (G1) is larger than or equal to 500 and less than or equal to 1357. 
       
     
     
         30 . The light-emitting element according to  claim 29 , wherein the EL layer further comprises a fluorescent substance. 
     
     
         31 . The light-emitting element according to  claim 29 , wherein the EL layer further comprises a phosphorescent substance. 
     
     
         32 . The light-emitting element according to  claim 29 ,
 wherein α 1  and α 2  in the general formula (G1) each independently represent any of general formulae (2-1) to (2-6) below, and   
       
         
           
           
               
               
           
         
         wherein: 
         R 11  to R 15  and R 21  to R 36  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and 
         R 37  and R 38  each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 
       
     
     
         33 . The light-emitting element according to  claim 29 ,
 wherein Ar in the general formula (G1) is any of general formulae (3-1) to (3-7) below, and   
       
         
           
           
               
               
           
         
         wherein: 
         R 41  to R 45 , R 51  to R 68 , and R 71  to R 79  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a biphenyl group. 
       
     
     
         34 . The light-emitting element according to  claim 29 ,
 wherein R 1  and R 6  in the general formula (G1) each independently represent any of structural formulae (4-1) to (4-6) or general formulae (4-7) to (4-12), and   
       
         
           
           
               
               
           
         
         wherein: 
         R 41  to R 45 , R 51  to R 68 , and R 71  to R 79  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a biphenyl group. 
       
     
     
         35 . The light-emitting element according to  claim 29 ,
 wherein R 2  to R 5  and R 7  to R 10  in the general formula (G1) each independently represent any of structural formulae (5-1) to (5-6) or general formulae (5-7) to (5-10, and   
       
         
           
           
               
               
           
         
         wherein R 41  to R 45 , R 51  to R 68 , and R 71  to R 79  each independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a biphenyl group. 
       
     
     
         36 . The light-emitting element according to  claim 29 ,
 wherein Ar, R 1 , and R 6  each represent an unsubstituted phenyl group,   wherein α 1  and α 2  each represent a phenylene group, and   wherein R 2  to R 5  and R 7  to R 10  each represent a hydrogen atom.   
     
     
         37 . A lighting device comprising the light-emitting element according to  claim 29 . 
     
     
         38 . A quinoxaline derivative represented by a structural formula (6-1), 
       
         
           
           
               
               
           
         
       
     
     
         39 . The quinoxaline derivative according to  claim 38 ,
 wherein δ (ppm)=7.02-7.13 (m, 7H), 7.26-7.43 (m, 12H), 7.56-7.60 (m, 4H), 7.75-7.78 (m, 4H), 8.15-8.18 (m, 4H) is obtained when the quinoxaline derivative according to claim  16  is measured by 300 MHz  1 H-NMR with using CDCl 3  as solvent.   
     
     
         40 . The quinoxaline derivative according to  claim 38 ,
 wherein δ (ppm)=123.1, 124.0, 125.4, 128.2, 128.9, 129.0, 129.2, 129.4, 129.7, 129.7, 129.9, 130.9, 133.0, 139.3, 141.1, 141.2, 146.7, 147.9, 152.9, 153.5 is obtained when the quinoxaline derivative according to claim  16  is measured by 75.5 MHz  13 C-NMR with using CDCl 3  as solvent.   
     
     
         41 . The quinoxaline derivative according to  claim 38 ,
 wherein toluene solution of the quinoxaline derivative according to claim  16  has maximum emission wavelength at 475 nm when the quinoxaline derivative according to claim  16  is excited with 400 nm wavelength.   
     
     
         42 . The quinoxaline derivative according to  claim 38 ,
 wherein a thin film of the quinoxaline derivative according to claim  16  has maximum emission wavelength at 501 nm when the quinoxaline derivative according to claim  16  is excited with 416 nm wavelength.