US2008303429A1PendingUtilityA1

Green luminescent materials

50
Assignee: HERRON NORMANPriority: Jun 1, 2007Filed: May 30, 2008Published: Dec 11, 2008
Est. expiryJun 1, 2027(~0.9 yrs left)· nominal 20-yr term from priority
C09K 11/06C09K 2211/1007C09K 2211/1014C09K 2211/1011H10K 85/633H10K 85/615H10K 85/626H10K 50/11H10K 85/341H10K 85/324H10K 2102/103
50
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Claims

Abstract

There is provided a green luminescent material having Formula I or Formula II R 1 and R 2 can be the same or different and can be hydrogen, alkoxy, tertiary alkyl, or cycloalkyl. R 3 and R 4 are the same or different and can be fluorine, aryl, or alkyl. There is also provided an organic electronic device containing the green luminescent material.

Claims

exact text as granted — not AI-modified
1 . A green luminescent material having Formula I or Formula II 
     
       
         
         
             
             
         
       
     
     wherein:
 R 1  and R 2  are the same or different and are selected from the group consisting of hydrogen, alkoxy, tertiary alkyl, and cycloalkyl. 
 R 3  and R 4  are the same or different and are selected from the group consisting of fluorine, aryl, and alkyl. 
 
   
   
       2 . The luminescent material of  claim 1 , wherein at least one of R 1  and R 2  is not hydrogen. 
   
   
       3 . The luminescent material of  claim 1 , wherein at least one of R 1  and R 2  is an alkoxy group selected from the group consisting of methoxy and ethoxy. 
   
   
       4 . The luminescent material of  claim 1 , wherein at least one of R 1  and R 2  is a tertiary alkyl group selected from the group consisting of t-butyl and neopentyl. 
   
   
       5 . The luminescent material of  claim 1 , wherein at least one of R 1  and R 2  is a cycloalkyl selected from the group consisting of cyclohexyl, 1-methylcyclohexyl, and 1-adamantyl. 
   
   
       6 . The luminescent material of  claim 1 , selected from the group consisting of compounds G1 through G12: 
     
       
         
               
               
               
               
               
               
             
                   
               
                 Compound 
                 Formula 
                 R 1   
                 R 2   
                 R 3   
                 R 4   
               
                   
               
                 G1 
                 I 
                 H 
                 H 
                 i-propyl 
                 t-butyl 
               
                 G2 
                 I 
                 t-butyl 
                 H 
                 i-propyl 
                 t-butyl 
               
                 G3 
                 I 
                 t-butyl 
                 t-butyl 
                 i-propyl 
                 t-butyl 
               
                 G4 
                 I 
                 1- 
                 1- 
                 i-propyl 
                 t-butyl 
               
                   
                   
                 methylcyclohexyl 
                 methylcyclohexyl 
               
                 G5 
                 II 
                 1- 
                 1- 
                 i-propyl 
                 t-butyl 
               
                   
                   
                 methylcyclohexyl 
                 methylcyclohexyl 
               
                 G6 
                 I 
                 methoxy 
                 methoxy 
                 i-propyl 
                 t-butyl 
               
                 G7 
                 I 
                 1-adamantyl 
                 1-adamantyl 
                 i-propyl 
                 t-butyl 
               
                 G8 
                 II 
                 1-adamantyl 
                 1-adamantyl 
                 i-propyl 
                 t-butyl 
               
                 G9 
                 I 
                 t-butyl 
                 t-butyl 
                 F 
                 F 
               
                 G10 
                 I 
                 1-adamantyl 
                 1-adamantyl 
                 phenyl 
                 phenyl 
               
                 G11 
                 I 
                 1-adamantyl 
                 1-adamantyl 
                 t-butyl 
                 3-biphenyl 
               
                 G12 
                 I 
                 1-adamantyl 
                 1-adamantyl 
                 t-butyl 
                 phenyl 
               
                   
               
           
              
              
              
             
             
              
              
              
              
              
              
              
              
              
              
              
              
              
              
              
             
          
         
       
     
   
   
       7 . An organic electronic device comprising a first electrical contact, a second electrical contact and a photoactive layer therebetween, the photoactive layer comprising a green luminescent material having Formula I or Formula II 
     
       
         
         
             
             
         
       
     
     wherein:
 R 1  and R 2  are the same or different and are selected from the group consisting of hydrogen, alkoxy, tertiary alkyl, and cycloalkyl. 
 R 3  and R 4  are the same or different and are selected from the group consisting of fluorine, aryl, and alkyl. 
 
   
   
       8 . The device of  claim 7 , wherein at least one of R 1  and R 2  is not hydrogen. 
   
   
       9 . The device of  claim 7 , wherein at least one of R 1  and R 2  is an alkoxy group selected from the group consisting of methoxy and ethoxy. 
   
   
       10 . The device of  claim 7 , wherein at least one of R 1  and R 2  is a tertiary alkyl group selected from the group consisting of t-butyl and neopentyl. 
   
   
       11 . The device of  claim 7 , wherein at least one of R 1  and R 2  is a cycloalkyl selected from the group consisting of cyclohexyl, 1-methylcyclohexyl, and 1-adamantyl. 
   
   
       12 . The device of  claim 7 , wherein the luminescent material is selected from the group consisting of compounds G1 through G12: 
     
       
         
               
               
               
               
               
               
             
                   
               
                 Compound 
                 Formula 
                 R 1   
                 R 2   
                 R 3   
                 R 4   
               
                   
               
                 G1 
                 I 
                 H 
                 H 
                 i-propyl 
                 t-butyl 
               
                 G2 
                 I 
                 t-butyl 
                 H 
                 i-propyl 
                 t-butyl 
               
                 G3 
                 I 
                 t-butyl 
                 t-butyl 
                 i-propyl 
                 t-butyl 
               
                 G4 
                 I 
                 1- 
                 1- 
                 i-propyl 
                 t-butyl 
               
                   
                   
                 methylcyclohexyl 
                 methylcyclohexyl 
               
                 G5 
                 II 
                 1- 
                 1- 
                 i-propyl 
                 t-butyl 
               
                   
                   
                 methylcyclohexyl 
                 methylcyclohexyl 
               
                 G6 
                 I 
                 methoxy 
                 methoxy 
                 i-propyl 
                 t-butyl 
               
                 G7 
                 I 
                 1-adamantyl 
                 1-adamantyl 
                 i-propyl 
                 t-butyl 
               
                 G8 
                 II 
                 1-adamantyl 
                 1-adamantyl 
                 i-propyl 
                 t-butyl 
               
                 G9 
                 I 
                 t-butyl 
                 t-butyl 
                 F 
                 F 
               
                 G10 
                 I 
                 1-adamantyl 
                 1-adamantyl 
                 phenyl 
                 phenyl 
               
                 G11 
                 I 
                 1-adamantyl 
                 1-adamantyl 
                 t-butyl 
                 3-biphenyl 
               
                 G12 
                 I 
                 1-adamantyl 
                 1-adamantyl 
                 t-butyl 
                 phenyl 
               
                   
               
           
              
              
              
             
             
              
              
              
              
              
              
              
              
              
              
              
              
              
              
              
             
          
         
       
     
   
   
       13 . The device of  claim 7 , wherein the photoactive layer further comprises a host material. 
   
   
       14 . The device of  claim 13  wherein the host material comprises at least one diarylanthracene. 
   
   
       15 . The device of  claim 14  wherein the diarylanthracene has the formula: 
     
       
         
         
             
             
         
       
     
     where:
 A 1  and A 2  are the same or different at each occurrence and are selected from the group consisting of H, an aromatic group, and an alkenyl group, or A may represent one or more fused aromatic rings; 
 p and q are the same or different and are an integer from 1-3. 
 
   
   
       16 . The device of  claim 15  wherein at least one of A 1  and A 2  comprises a naphthyl group. 
   
   
       17 . The device of  claim 16  wherein the host is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
     and combinations thereof. 
   
   
       18 . A photoactive layer comprising a green luminescent material of  claim 1 . 
   
   
       19 . The photoactive layer of  claim 18  further comprising a host material comprising at least one diarylanthracene.

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