Organic Electroluminescent Materials and Devices

Abstract

This invention discloses oligosilane compounds. These compounds can be used in OLEDs.

1 . A compound having a formula selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein m is an integer from 0 to 20, n is an integer from 1 to 10; 
         wherein when m or n is more than 1, each R 1  and R 8  can be same or different; 
         wherein R 1  to R 8  are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
         wherein at least one of R 1  to R 8  comprises at least one chemical group selected from the group consisting of naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, imidazole, oxazole, thiazole, triphenylene, fluorene, indole, carbazole, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene 
       
       
         
           
           
               
               
           
         
       
       wherein X is NR and R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
 wherein none of R 1  to R 8  represents indole. 
 
     
     
         2 . The compound of  claim 1 , wherein the formula of the compound is Formula I. 
     
     
         3 . The compound of  claim 1 , wherein the formula of the compound is Formula II. 
     
     
         4 . The compound of  claim 1 , wherein m is at least 1. 
     
     
         5 . The compound of  claim 1 , wherein n is at least 2. 
     
     
         6 . The compound of  claim 1 , wherein R 1  to R 8  are each independently selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl. 
     
     
         7 . The compound of  claim 1 ,
 wherein at least one of R 1  to R 8  comprises at least one chemical group selected from the group consisting of triphenylene, fluorene, carbazole, dibenzothiophene, dibenzofuran, and dibenzoselenophene; and   wherein at least one of R 1  to R 8  comprises at least one chemical group selected from the group consisting of aza-triphenylene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.   
     
     
         8 . The compound of  claim 1 ,
 wherein in Formula I, R 1  comprises at least one chemical group selected from the group consisting of triphenylene, fluorene, carbazole, dibenzothiophene, dibenzofuran, and dibenzoselenophene; and   wherein R 5  comprises at least one chemical group selected from the group consisting of aza-triphenylene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.   
     
     
         9 . The compound of  claim 1 , wherein R 1  to R 8  are each independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein X is selected from the group consisting of O, S, Se, and NR; and 
         wherein R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. 
       
     
     
         10 . The compound of  claim 1 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein X is selected from the group consisting of O, S and Se. 
       
     
     
         11 . The compound of  claim 10 , wherein m is 0. 
     
     
         12 . The compound of  claim 10 , wherein m is 1. 
     
     
         13 . The compound of  claim 10 , wherein m is 2. 
     
     
         14 . The compound of  claim 10 , wherein X is O. 
     
     
         15 . The compound of  claim 10 , wherein X is S. 
     
     
         16 . The compound of  claim 1 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein X is selected from the group consisting of O, S, Se. 
       
     
     
         17 . The compound of  claim 1 , wherein the compound has a donor-linker-acceptor configuration. 
     
     
         18 . The compound of  claim 16 , wherein n is 1. 
     
     
         19 . The compound of  claim 16 , wherein n is 2. 
     
     
         20 . The compound of  claim 16  Error! Reference source not found., wherein X is O. 
     
     
         21 . The compound of  claim 16 , wherein X is S. 
     
     
         22 . An organic light emitting device (OLED) comprising:
 an anode;   a cathode; and   an organic layer, disposed between the anode and the cathode, comprising a compound having a formula selected from the group consisting of:   
       
         
           
           
               
               
           
         
         wherein m is an integer from 0 to 20, n is an integer from 1 to 10; 
         wherein when m or n is more than 1, each R 7  and R 8  can be same or different; 
         wherein R 1  to R 8  are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
         wherein at least one of R 1  to R 8  comprises at least one chemical group selected from the group consisting of naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, imidazole, oxazole, thiazole, triphenylene, fluorene, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene 
       
       
         
           
           
               
               
           
         
       
       wherein X is NR and R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
 wherein none of R 1  to R 8  represents indole. 
 
     
     
         23 . The OLED of  claim 22 , wherein the organic layer is an emissive layer and the compound of Formula I or II is a host. 
     
     
         24 . The OLED of  claim 22 , wherein the organic layer further comprises a phosphorescent emissive dopant;
 wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein each X 1  to X 13  are independently selected from the group consisting of carbon and nitrogen; 
         wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″; 
         wherein R 1  and R″ are optionally fused or joined to form a ring; 
         wherein each R a , R b , R c , and R d  may represent from mono substitution to the possible maximum number of substitution, or no substitution; 
         wherein R′, R″, R a , R b , R c , and R d  are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
         wherein any two adjacent substituents of R a , R b , R c , and R d  are optionally fused or joined to form a ring or form a multidentate ligand. 
       
     
     
         25 . The OLED of  claim 22 , wherein the organic layer is a blocking layer and the compound of Formula I or II is a blocking material in the organic layer. 
     
     
         26 . The OLED of  claim 22 , wherein the organic layer is a transporting layer and the compound of Formula I or II is a transporting material in the organic layer. 
     
     
         27 . The OLED of  claim 22 , wherein the organic layer is an emissive layer and the compound of Formula I or II is an emitter. 
     
     
         28 . The OLED of  claim 22 , wherein the organic layer is an emissive layer and the compound of Formula I or II is a delayed fluorescent emitter. 
     
     
         29 . The OLED of  claim 22 , wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel. 
     
     
         30 . A formulation comprising a compound having a formula selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein m is an integer from 0 to 20, n is an integer from 1 to 10; 
         wherein when m or n is more than 1, each R 1  and R 8  can be same or different; 
         wherein R 1  to R 8  are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
         wherein at least one of R 1  to R 8  comprises at least one chemical group selected from the group consisting of naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, imidazole, oxazole, thiazole, triphenylene, fluorene, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-fluorene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene 
       
       
         
           
           
               
               
           
         
       
       wherein X is NR and R is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
 wherein none of R 1  to R 8  represents indole.