Ethynyl containing electron transport dyes and compositions

Abstract

Compounds, compositions, organic electronic devices, and methods for preparing organic electronic devices are described. The compounds of the invention contain at least two carbon-carbon triple bonds and a heteroaromatic ring having at least one —C═N— unit. The compounds can be used as electron transport agents in organic electronic devices such as organic electroluminescent devices.

1 . A method of making an organic electroluminescent device comprising: 
 (a) preparing a donor sheet comprising a transfer layer that comprises a compound of Formula I:                           wherein 
 D is a monovalent, divalent, trivalent, or tetravalent radical of a C 3-30  alkane, C 3-30  heteroalkane, conjugated or unconjugated C 6-60  carbocyclic aromatic compound, C 3-60  heteroaromatic compound, C 18-60  tertiary aromatic amino compound, or a compound of Formula II or Formula III  
                     
  wherein D is unsubstituted or substituted with one or more alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, heteroalkyl, heteroaryl, or combinations thereof, wherein  
 Ar 1  is trivalent radical of a conjugated C 6-30  carbocyclic aromatic compound that is unsubstituted or substituted with one or more alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, heteroalkyl, heteroaryl, or combinations thereof;  
 E is a C 3-60  heteroarylene having at least one —C═N— unit, said heteroarylene being unsubstituted or substituted with one or more alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, heteroalkyl, heteroaryl, or combinations thereof;  
 G is a monovalent radical selected from hydrogen, C 1-30  alkyl, C 1-30  heteroalkyl, C 3-60  heteroaryl, C 6-60  aryl, or C 18-60  tertiary aromatic amino aryl, wherein G is unsubstituted or substituted with one or more alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, heteroalkyl, heteroaryl, or combinations thereof;  
 J is a monovalent radical selected from C 1-30  alkyl, C 1-30  heteroalkyl, C 3-60  heteroaryl, C 6-60  aryl, or C 18-60  tertiary aromatic amino aryl, wherein J is unsubstituted or substituted with one or more alkyl, alkenyl, alkoxy, aryl, aryloxy, fluoro, fluoroalkyl, perfluoroalkyl, heteroalkyl, heteroaryl, or combinations thereof;  
 Z is NH or CH 2  and  
 n is an integer of 1 to 4, wherein no more than one of D and J is an unsubstituted phenyl when n is equal to 1; and  
   (b) transferring the transfer layer from the donor sheet to a receptor substrate, wherein the transfer layer forms at least part of a light emissive structure.    
   
   
       2 . The method of  claim 1 , wherein the donor sheet comprises a base substrate, the transfer layer, and a light-to-heat conversion layer between the base substrate and the transfer layer.  
   
   
       3 . The method of  claim 1 , wherein the transfer layer further comprises a second compound selected from a charge transporting material, a charge blocking material, a light emitting material, a color conversion material, a polymeric binder, or a combination thereof.  
   
   
       4 . The method of  claim 1 , wherein the transfer layer has a multilayer construction.  
   
   
       5 . The method of  claim 1 , wherein the transferring comprises placing the transfer layer of the donor sheet adjacent to the receptor sheet and selectively heating the donor sheet.  
   
   
       6 . The method of  claim 1 , wherein the transfer layer is thermally annealed after transferring.  
   
   
       7 . The method of  claim 1 , wherein D comprises a radical of a C 6-60  aromatic compound selected from  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     wherein 
 D is unsubstituted or substituted with one or more substituents selected from C 1-20  alkyl, C 2-20  alkenyl, C 1-20  alkoxy, C 6-20  aryl, C 6-20  aryloxy, fluoro, C 1-20  fluoroalkyl, C 1-20  perfluoroalkyl, C 1-20  heteroalkyl, C 3-20  heteroaryl, and combinations thereof;  
 each R is independently an C 1-30  alkyl, C 2-30  alkenyl, C 1-30  alkoxy, C 6-30  aryl, C 6-30  aryloxy, fluoro, C 1-30  fluoroalkyl, C 1-30  perfluoroalkyl, C 1-30  heteroalkyl, C 3-30  heteroaryl, or combinations thereof; and  
 A is C, Si, Ge, Pb, or Sn.  
 
   
   
       8 . The method of  claim 1 , wherein D comprises a radical of a C 3-60  heteroaromatic compound having at least one —C═N— unit, said C 3-60  heteroaromatic compound selected from  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     wherein 
 D is unsubstituted or substituted with one or more substituents selected from C 1-20  alkyl, C 2-20  alkenyl, C 1-20  alkoxy, C 6-20  aryl, C 6-20  aryloxy, fluoro, C 1-20  fluoroalkyl, C 1-20  perfluoroalkyl, C 1-20  heteroalkyl, C 3-20  heteroaryl, and combinations thereof; and  
 X is O, S, or NR 2  where R 2  is a C 1-30  alkyl, a C 1-30  heteroalkyl, a C 6-20  aryl, a C 3-20  heteroaryl, or a combination thereof.  
 
   
   
       9 . The method of  claim 1 , wherein D comprises a radical of a C 3-60  heteroaromatic compound that is electron rich or of a C 18-60  tertiary aromatic amino compound selected from  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     wherein 
 D is unsubstituted or substituted with one or more substituents selected from C 1-20  alkyl, C 2-20  alkenyl, C 1-20  alkoxy, C 6-20  aryl, C 6-20  aryloxy, fluoro, C 1-20  fluoroalkyl, C 1-20  perfluoroalkyl, C 1-20  heteroalkyl, C 3-20  heteroaryl, and combinations thereof;  
 each R is independently an C 1-30  alkyl, C 2-30  alkenyl, C 1-30  alkoxy, C 6-30  aryl, C 6-30  aryloxy, fluoro, C 1-30  fluoroalkyl, C 1-30  perfluoroalkyl, C 1-30  heteroalkyl, C 3-30  heteroaryl, or combinations thereof;  
 X is O, S, or NR 2  where R 2  is a C 1-30  alkyl, a C 1-30  heteroalkyl, a C 6-20  aryl, a C 3-20  heteroaryl, or a combination thereof; and  
 t is an integer of 1 to 4.  
 
   
   
       10 . The method of  claim 1 , wherein n is equal to 2 and D comprises a radical selected from  
     
       
         
         
             
             
         
       
     
     wherein 
 D is unsubstituted or substituted with one or more substituents selected from C 1-20  alkyl, C 2-20  alkenyl, C 1-20  alkoxy, C 6-20  aryl, C 6-20  aryloxy, fluoro, C 1-20  fluoroalkyl, C 1-20  perfluoroalkyl, C 1-20  heteroalkyl, C 3-20  heteroaryl, and combinations thereof; and  
 each R is independently an C 1-30  alkyl, C 2-30  alkenyl, C 1-30  alkoxy, C 6-30  aryl, C 6-30  aryloxy, fluoro, C 1-30  fluoroalkyl, C 1-30  perfluoroalkyl, C 1-30  heteroalkyl, C 3-30  heteroaryl, or combinations thereof.  
 
   
   
       11 . The method of  claim 1 , wherein n is equal to 3 and D comprises a radical selected from  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     wherein 
 D is unsubstituted or substituted with one or more substituents selected from C 1-20  alkyl, C 2-20  alkenyl, C 1-20  alkoxy, C 6-20  aryl, C 6-20  aryloxy, fluoro, C 1-20  fluoroalkyl, C 1-20  perfluoroalkyl, C 1-20  heteroalkyl, C 3-20  heteroaryl, and combinations thereof; and  
 each R is independently a C 1-30  alkyl, C 2-30  alkenyl, C 1-30  alkoxy, C 6-30  aryl, C 6-30  aryloxy, fluoro, C 1-30  fluoroalkyl, C 1-30  perfluoroalkyl, C 1-30  heteroalkyl, C 3-30  heteroaryl, or combinations thereof.  
 
   
   
       12 . The method of  claim 1 , wherein n is equal to 4 and D comprises a radical selected from  
     
       
         
         
             
             
         
       
     
     wherein 
 D is unsubstituted or substituted with one or more substituents selected from C 1-20  alkyl, C 2-20  alkenyl, C 1-20  alkoxy, C 6-20  aryl, C 6-20  aryloxy, fluoro, C 1-20  fluoroalkyl, C 1-20  perfluoroalkyl, C 1-20  heteroalkyl, C 3-20  heteroaryl, and combinations thereof.  
 
   
   
       13 . The method of  claim 1 , wherein Ar 1  comprises a trivalent radical of  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     wherein 
 Ar 1  is unsubstituted or substituted with one or more substituents selected from C 1-20  alkyl, C 2-20  alkenyl, C 1-20  alkoxy, C 6-20  aryl, C 6-20  aryloxy, fluoro, C 1-20  fluoroalkyl, C 1-20  perfluoroalkyl, C 1-20  heteroalkyl, C 3-20  heteroaryl, and combinations thereof; and  
 each R is independently an C 1-30  alkyl, C 2-30  alkenyl, C 1-30  alkoxy, C 6-30  aryl, C 6-30  aryloxy, fluoro, C 1-30  fluoroalkyl, C 1-30  perfluoroalkyl, C 1-30  heteroalkyl, C 3-30  heteroaryl, or combinations thereof.  
 
   
   
       14 . The method of  claim 1 , wherein Ar 1  comprises a trivalent radical of benzene.  
   
   
       15 . The method of  claim 1 , wherein E comprises a radical of oxadiazole, N-substituted triazole, N-substituted imidazole, benzoimidazole, N-substituted pyrazole, oxazole, isoxazole, thiazole, thiadiazole, benzothiadiazole, isothiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, tetrazine, benzoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, phthalazine, benzotriazine, phenazine, phenanthridine, or acridine.  
   
   
       16 . The method of  claim 1 , wherein E comprises a radical of benzoimidazole, oxadiazole, thiadiazole, or triazole.  
   
   
       17 . The method of  claim 1 , wherein E comprises a radical of oxadiazole.  
   
   
       18 . The method of  claim 1 , wherein G comprises a monovalent radical of  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     wherein 
 G is unsubstituted or substituted with one or more substituents selected from C 1-20  alkyl, C 2-20  alkenyl, C 1-20  alkoxy, C 6-20  aryl, C 6-20  aryloxy, fluoro, C 1-20  fluoroalkyl, C 1-20  perfluoroalkyl, C 1-20  heteroalkyl, C 3-20  heteroaryl, and combinations thereof;  
 each R is independently an C 1-30  alkyl, C 2-30  alkenyl, C 1-30  alkoxy, C 6-30  aryl, C 6-30  aryloxy, fluoro, C 1-30  fluoroalkyl, C 1-30  perfluoroalkyl, C 1-30  heteroalkyl, C 3-30  heteroaryl, or combinations thereof;  
 X is O, S, or NR 2  where R 2  is a C 1-30  alkyl, a C 1-30  heteroalkyl, a C 6-20  aryl, a C 3-20  heteroaryl, or a combination thereof; and  
 t is an integer of 0 to 4.  
 
   
   
       19 . The method of  claim 1 , wherein the compound of Formula I is  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
   
   
       20 . The method of  claim 1 , wherein the compound of Formula I is  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
   
   
       21 . The method of  claim 1 , wherein the compound of Formula I is