Quinoxaline-fused dibenzosuberane based helicenes and organic electroluminescent device using the same

Abstract

A quinoxaline-fused dibenzosuberane based helicene is shown in formula (1), wherein A is with a structure of formula (2), formula (3a) or formula (3b); X is an oxygen atom, sulfur atom, amino group, or —(CH 2 ) n , wherein n is 0, 1, or 2; R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a halogen atom, formula (4), formula (5) and formula (6); and R 3 to R 15 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a thioalkyl group, a silyl group, an alkenyl group, an aryl group, a heteroaryl group, and an amino group.

What is claimed is: 
     
         1 . A quinoxaline-fused dibenzosuberane based helicene, comprising a structure of the following General Formula (1), 
       
         
           
           
               
               
           
         
         wherein A is represented by General Formula (2), General Formula (3a) or General Formula (3b); 
       
       
         
           
           
               
               
           
         
         wherein X is an oxygen atom, sulfur atom, amino group, or —(CH 2 ) n , n is 0, 1, or 2; R 1  and R 2  are both independently a hydrogen atom, a halogen atom, General Formula (4), General Formula (5) or General Formula (6); and 
       
       
         
           
           
               
               
           
         
         wherein R 3  to R 15  are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group, an alkenyl group, an aryl group, and an amino group. 
       
     
     
         2 . The quinoxaline-fused dibenzosuberane based helicene of  claim 1 , wherein the alkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkyl group with the carbon number of 3 to 6, the cycloalkyl group is a substituted or unsubstituted cycloalkyl group with the carbon number of 3 to 6, the alkoxy group is selected from the group consisting of a substituted or unsubstituted straight-chain alkoxy group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain alkoxy group with the carbon number of 3 to 6, the haloalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain haloalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain haloalkyl group with the carbon number of 3 to 6, the thioalkyl group is selected from the group consisting of a substituted or unsubstituted straight-chain thioalkyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain thioalkyl group with the carbon number of 3 to 6, the silyl group is selected from the group consisting of a substituted or unsubstituted straight-chain silyl group with the carbon number of 1 to 6, and a substituted or unsubstituted branched-chain silyl group with the carbon number of 3 to 6, the alkenyl group is selected from the group consisting of a substituted or unsubstituted straight-chain alkenyl group with the carbon number of 2 to 6, and a substituted or unsubstituted branched-chain alkenyl group with the carbon number of 3 to 6, the aryl group is a substituted or unsubstituted aromatic hydrocarbon with the carbon number of 6 to 16, or a substituted or unsubstituted hetero aromatic ring with the carbon number of 5 to 16, and the amino group is a secondary amino group or a tertiary amino group. 
     
     
         3 . The quinoxaline-fused dibenzosuberane based helicene of  claim 1 , wherein R 13  is an amino group or a substituted or unsubstituted straight-chain alkyl group with the carbon number of 1 to 6. 
     
     
         4 . The quinoxaline-fused dibenzosuberane based helicene of  claim 1 , wherein R 14  is a substituted or unsubstituted straight-chain alkyl group with the carbon number of 1 to 6. 
     
     
         5 . The quinoxaline-fused dibenzosuberane based helicene of  claim 1 , wherein R 15  is an aryl group or a substituted or unsubstituted straight-chain alkyl group with the carbon number of 1 to 6. 
     
     
         6 . The quinoxaline-fused dibenzosuberane based helicene of  claim 1 , being represented by one of following chemical formula I to chemical formula IV. 
       
         
           
           
               
               
           
         
       
     
     
         7 . The quinoxaline-fused dibenzosuberane based helicene of  claim 1 , having glass transition temperatures ranged from 108° C. to 146° C. and decomposition temperatures ranged from 385° C. to 547° C. 
     
     
         8 . The quinoxaline-fused dibenzosuberane based helicene of  claim 1 , having oxidation potentials ranged from 0.6V to 1.0V and redox potentials ranged from −1.60V to −1.66V. 
     
     
         9 . The quinoxaline-fused dibenzosuberane based helicene of  claim 1 , having highest occupied molecular orbital energy levels (E HOMO ) ranged from −5.28 eV to −5.98 eV and lowest unoccupied molecular orbital energy levels (E LUMO ) ranged from −3.14 eV to −3.20 eV. 
     
     
         10 . The quinoxaline-fused dibenzosuberane based helicene of  claim 6 , which is applied in an organic electroluminescent device for being as a light emitting material, a hole-transporting material and/or an electron-transporting material.