Process for the preparation of novel dyes for use in imaging members

Abstract

There are described novel rhodamine dye compounds and imaging members and imaging methods, including thermal imaging members and imaging methods, utilizing the compounds. The dye compounds exhibit a first color when in the crystalline form and a second color, different from the first color, when in the liquid, amorphous form.

1 . A compound represented by the formula  
     
       
         
         
             
             
         
       
     
     wherein: 
 R 1 , R 3 , R 4 , R 5 , R 6  and R 7  are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted, alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur;  
 R 2  is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, substituted oxygen, substituted nitrogen and substituted sulfur;  
 R 8  is absent or selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur;  
 R 9 , R 10  and R 11  are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur;  
 R 12 , R 13 , R 14  and R 15  are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, aryl, substituted aryl, heteroaryl, and substituted heteroaryl;  
 R 16 , R 17 , R 18  and R 19  are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur; and  
 X 1  is carbon or nitrogen.  
 
   
   
       2 . A compound according to  claim 1  wherein R 8 , R 9 , R 10  and R 11  are halogen, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18  and R 19  are as defined in  claim 1  and X 1  is carbon.  
   
   
       3 . The imaging member comprising a first image-forming layer including a compound according to  claim 1 , said compound being in the crystalline form.  
   
   
       4 . The imaging member as defined in  claim 3  and further including a substrate and at least a second color-forming layer, said second color-forming layer being capable of forming a color different from that formed by said first color-forming layer.  
   
   
       5 . The imaging member as defined in  claim 4  and further including a third color-forming layer, said third color-forming layer being capable of forming a color different from those formed by said first and second color-forming layers.  
   
   
       6 . The imaging member as defined in  claim 5  wherein said color-forming layers form magenta, cyan and yellow color, respectively.  
   
   
       7 . The imaging method comprising 
 (a) providing an imaging member as defined in  claim 3;  and    (b) converting at least a portion of said compound to the liquid form in an imagewise pattern whereby an image is formed.    
   
   
       8 . The method as defined in  claim 7  wherein step (b) comprises applying an imagewise pattern of thermal energy to said imaging member whereby at least a portion of said compound is converted to the liquid form and an image is formed.  
   
   
       9 . The thermal imaging method as defined in  claim 8  wherein said imaging member further includes a substrate and at least a second color-forming layer, said second color-forming layer being capable of forming a color different from that formed by said first color-forming layer.  
   
   
       10 . The imaging method as defined in  claim 8  wherein said imaging member further includes a third color-forming layer, said third color-forming layer being capable of forming a color different from those formed by said first and second color-forming layers.  
   
   
       11 . The imaging method as defined in  claim 10  wherein said color-forming layers form magenta, cyan and yellow color, respectively.