Organic compounds and electronic device comprising organic layer comprising organic compounds

Abstract

Organic compounds suitable for organic layers of electronic devices that show reduced driving voltage, increased luminous efficiency and/or increased power efficiency.

What is claimed is: 
     
         1 . An organic compound having the structure represented by Formula (1): 
       
         
           
           
               
               
           
         
         wherein R 1 , R 3 , and R 4  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1- -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; 
         R 2  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; and R 1  with R 2 , R 2  with R 3 , or R 3  with R 4  may optionally form one or more ring structures; 
         R 5  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 3 -C 50  cycloalkyl, a substituted or unsubstituted C 6 -C 60  aryl, and a substituted or unsubstituted C 1 -C 60  heteroaryl; 
         R 6  and R 7  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a substituted or unsubstituted C 1 -C 60  heteroaryl, a halogen, a cyano, a hydroxyl, a carbonyl, and a substituted amino group having the structure of 
       
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60  aryl and a substituted or unsubstituted C 1 -C 60  heteroaryl; with the proviso that at least one of R 6  and R 7  is the substituted amino group; and
 L 1  and L 2  are each independently selected from the following structure: 
 
       
         
           
           
               
               
           
         
         wherein A 1  is selected from a substituted or unsubstituted heteroatom selected from O, P, S, NR′, PR′, or P(═O)R′; wherein each R′ is hydrogen or a C 1 -C 30  hydrocarbyl; 
         A 2  through A 5  are each independently selected from CR′ 2  or a substituted or unsubstituted heteroatom selected from N, P, PR′ 2 , or P(═O); wherein each R′ is hydrogen or a C 1 -C 30  hydrocarbyl; 
         A 6  through A 11  are each independently selected from CH, N, P, PR′ 2 , P(═O), or C; and provided that A 6  through A 11  each independently represent C only when they are bonded to the indole moiety or X; and 
         X is a chemical bond or selected from the group consisting of a substituted or unsubstituted C 1 -C 50  alkylene, a substituted or unsubstituted C 3 -C 50  cycloalkylene, a substituted or unsubstituted C 6 -C 60  arylene, and a substituted or unsubstituted C 1 -C 60  heteroarylene; and X may form one or more rings with the ring it is bonded to. 
       
     
     
         2 . The organic compound of  claim 1 , wherein L 1  and L 2  are each independently a substituted or unsubstituted C 6 -C 60  arylene. 
     
     
         3 . The organic compound of  claim 1 , wherein the organic compound has the structure represented by Formula (2): 
       
         
           
           
               
               
           
         
         wherein X 1  and X 2  are each a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50  alkylene, a substituted or unsubstituted C 3 -C 50  cycloalkylene, a substituted or unsubstituted C 6 -C 60  arylene, and a substituted or unsubstituted C 1 -C 60  heteroarylene; and X 1  and X 2  may each independently form one or more rings with the rings they are bonded to; 
         R 1 , R 3 , and R 4  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; 
         R 2  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; and R 1  with R 2 , R 2  with R 3 , or R 3  with R 4  may optionally form one or more ring structures; 
         R 5  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 3 -C 50  cycloalkyl, a substituted or unsubstituted C 6 -C 60  aryl, and a substituted or unsubstituted C 1 -C 60  heteroaryl; and 
         R 6  and R 7  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a substituted or unsubstituted C 1 -C 60  heteroaryl, a halogen, a cyano, a hydroxyl, a carbonyl, and a substituted amino group having the structure of 
       
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60  aryl and a substituted or unsubstituted C 1 -C 60  heteroaryl; with the proviso that at least one of R 6  and R 7  is the substituted amino group. 
     
     
         4 . The organic compound of  claim 1 , wherein the organic compound has the structure of Formula (3-I): 
       
         
           
           
               
               
           
         
         wherein A 7  and A 7 ′ are each C; 
         A 6  and A 6 ′, A 5  through A 11 , and A 8 ′ through A 11 ′ are each independently selected from CH, N, P, PR′ 2 , and P(═O); wherein each R′ is hydrogen or a C 1 -C 30  hydrocarbyl; and three or less of A 6  and A 5  through A 11 , and three of less of A 6 ′ and A 8 ′ through A 11 ′ are N; and provided that A 6  and A 8  through A 11  are each independently C only when they are bonded to the indole moiety or X 1 , and A 6 ′ and A 8 ′ through A 11 ′ are each independently C only when they are bonded to the indole moiety or X 2 ; 
         X 1  and X 2  are each a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50  alkylene, a substituted or unsubstituted C 3 -C 50  cycloalkylene, a substituted or unsubstituted C 6 -C 60  arylene, and a substituted or unsubstituted C 1 -C 60  heteroarylene; and X 1  and X 2  may each independently form one or more rings with the rings they are bonded to; 
         R 1 , R 3 , and R 4  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; 
         R 2  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; and R 1  with R 2 , R 2  with R 3 , or R 3  with R 4  may optionally form one or more ring structures; 
         R 5  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 3 -C 50  cycloalkyl, a substituted or unsubstituted C 6 -C 60  aryl, and a substituted or unsubstituted C 1 -C 60  heteroaryl; and 
         R 6  and R 7  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a substituted or unsubstituted C 1 -C 60  heteroaryl, a halogen, a cyano, a hydroxyl, a carbonyl, and a substituted amino group having the structure of 
       
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60  aryl and a substituted or unsubstituted C 1 -C 60  heteroaryl;
 with the proviso that at least one of R 6  and R 7  is the substituted amino group, and at least one of R 1  through R 4 , R 6  and R 7  is F or a fluoro-containing C 1 -C 30  alkyl or C 6 -C 60  aryl group. 
 
     
     
         5 . The organic compound of  claim 1 , wherein the organic compound has the structure of Formula (3): 
       
         
           
           
               
               
           
         
         wherein A 7  and A 7 ′ are each C; 
         A 6  and A 6 ′, A 8  through A 11 , and A 8 ′ through A 11 ′ are each independently selected from CH, N, P, PR′ 2 , and P(═O); wherein each R′ is hydrogen or a C 1 -C 30  hydrocarbyl; and three or less of A 6  and A 8  through A 11 , and three of less of A 6 ′ and A 8 ′ through A 11 ′ are N; and provided that A 6  and A 8  through A 11  are each independently C only when they are bonded to the indole moiety or X 1 , and A 6 ′ and A 8 ′ through A 11 ′ are each independently C only when they are bonded to the indole moiety or X 2 ; 
         X 1  and X 2  are each a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50  alkylene, a substituted or unsubstituted C 3 -C 50  cycloalkylene, a substituted or unsubstituted C 6 -C 60  arylene, and a substituted or unsubstituted C 1 -C 60  heteroarylene; and X 1  and X 2  may each independently form one or more rings with the rings they are bonded to; 
         R 5  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 3 -C 50  cycloalkyl, a substituted or unsubstituted C 6 -C 60  aryl, and a substituted or unsubstituted C 1 -C 60  heteroaryl; and 
         R 6  and R 7  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a substituted or unsubstituted C 1 -C 60  heteroaryl, a halogen, a cyano, a hydroxyl, a carbonyl, and a substituted amino group having the structure of 
       
       
         
           
           
               
               
           
         
       
       wherein Ar 1  and Ar 2  are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60  aryl and a substituted or unsubstituted C 1 -C 60  heteroaryl; with the proviso that at least one of R 6  and R 7  is the substituted amino group. 
     
     
         6 . The organic compound of  claim 1 , wherein Ar 1  and Ar 2  are each independently a substituted or unsubstituted C 6 -C 20  aryl. 
     
     
         7 . The organic compound of any one of  claims 1 - 4 , wherein at least one of R 1  through R 4 , R 6  and R 7  is F. 
     
     
         8 . The organic compound of any one of  claims 1 - 6 , wherein one of R 6  and R 7  is the substituted amino group, and the other one of R 6  and R 7  is selected from hydrogen, a halogen, a substituted or unsubstituted C 6 -C 60  aryl. 
     
     
         9 . The organic compound of any one of  claims 1 - 4 , wherein the organic compound is represented by Formula (2c): 
       
         
           
           
               
               
           
         
         wherein X 1  is a chemical bond, or selected from the group consisting of a substituted or unsubstituted C 1 -C 50  alkylene, a substituted or unsubstituted C 3 -C 50  cycloalkylene, a substituted or unsubstituted C 6 -C 60  arylene, and a substituted or unsubstituted C 1 -C 60  heteroarylene; 
         Ar 1  and Ar 2  are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60  aryl and a substituted or unsubstituted C 1 -C 60  heteroaryl; 
         R 1 , R 3 , and R 4  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; 
         R 2  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; and R 1  with R 2 , R 2  with R 3 , or R 3  with R 4  may optionally form one or more ring structures; and 
         R 5  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 3 -C 50  cycloalkyl, a substituted or unsubstituted C 6 -C 60  aryl, and a substituted or unsubstituted C 1 -C 60  heteroaryl. 
       
     
     
         10 . The organic compound of any one of  claims 1 - 4 , wherein the organic compound is represented by Formula (2d): 
       
         
           
           
               
               
           
         
         wherein X 2  is a chemical bond, or selected from the group consisting of a substituted or unsubstituted C 1 -C 50  alkylene, a substituted or unsubstituted C 3 -C 50  cycloalkylene, a substituted or unsubstituted C 6 -C 60  arylene, and a substituted or unsubstituted C 1 -C 60  heteroarylene; 
         Ar 1  and Ar 2  are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60  aryl and a substituted or unsubstituted C 1 -C 60  heteroaryl; 
         R 1 , R 3 , and R 4  are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60  aryl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; 
         R 2  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 1 -C 50  alkoxy, a substituted or unsubstituted C 1 -C 50  alkoxycarbonyl, a substituted or unsubstituted C 1 -C 60  heteroaryl, a substituted or unsubstituted C 6 -C 60  aryloxy, a substituted or unsubstituted C 6 -C 60  arylthio, a halogen, a cyano, a hydroxyl, and a carbonyl; and R 1  with R 2 , R 2  with R 3 , or R 3  with R 4  may optionally form one or more ring structures; and 
         R 5  is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50  alkyl, a substituted or unsubstituted C 3 -C 50  cycloalkyl, a substituted or unsubstituted C 6 -C 60  aryl, and a substituted or unsubstituted C 1 -C 60  heteroaryl. 
       
     
     
         11 . The organic compound of  claim 1 , wherein the substituted amino group is selected from the following structures (5-1) through (5-6): 
       
         
           
           
               
               
           
         
       
     
     
         12 . The organic compound of  claim 1 , wherein L 1  and L 2  are each independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         13 . The organic compound of any one of  claims 1 - 6 , wherein R 5  is selected from the group consisting of —CH 3 , —CH 2 CH 3 , 
       
         
           
           
               
               
           
         
       
     
     
         14 . The organic compound of any one of  claims 1 - 4 , wherein at least one of R 1  through R 4  is F and the remaining R 1  through R 4  are each hydrogen, and R 5  is —CH 3 . 
     
     
         15 . The organic compound of  claim 1 , wherein the organic compound is selected from the following compounds (1) through (24): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         16 . The organic compound of  claim 1 , wherein the organic compound is selected from the following compounds (25) through (34): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         17 . An electronic device comprising an organic layer, wherein the organic layer comprises the organic compound of any one of  claims 1 - 16 . 
     
     
         18 . The electronic device of  claim 17 , wherein the organic layer comprises a hole transport layer, an emissive layer, an electron transport layer, or a hole injection layer. 
     
     
         19 . The electronic device of  claim 18 , wherein the electronic device is a light emitting device.