Novel dye complexes and use thereof in imaging members and methods

Abstract

There are described novel complexes formed between hydrogen bond acceptors and phenolic dye compounds and imaging members and imaging methods, including thermal imaging members and methods utilizing the complexes.

1 . A compound represented by the formula  
       
         
           
           
               
               
           
         
       
       wherein: 
 R 1 , R 2 , R 3 , R 4 , R 5 , 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 6  is selected from the group consisting of halogen, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur;  
 R 8 , R 9 , R 10  and R 11  are each independently absent or selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acyl amino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur;  
 X 1  is selected from the group consisting of carbonyl, methylene, substituted methylene, and sulfonyl;  
 X 2  is selected from the group consisting of oxygen, nitrogen, or substituted nitrogen;  
 X 3  is selected from the group consisting of oxygen, sulfur, nitrogen and substituted nitrogen;  
 X 4  is carbon or nitrogen; and  
 A is a hydrogen-bond accepting group.  
 
     
     
         2 . A compound according to  claim 1  wherein A is a radical of a compound represented by the formula  
       
         
           
           
               
               
           
         
       
       wherein: 
 R 12 , R 13 , R 14 , R 15  and R 16  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, substituted oxygen, nitrogen, substituted nitrogen, and substituted sulfur; and  
 X 5  is carbon or nitrogen.  
 
     
     
         3 . A compound as defined in  claim 2  wherein A is a radical of a compound selected from the group consisting of phenanthroline, 2,9-dimethylphenanthroline, 4,5,6,7-tetramethylphenanthroline, methyl picolinate, ethyl picolinate, pyrazine, 4,4′-bipyridine, 2,2′-bipyridine, 1,2-bis(4-pyridyl)ethane and trans-1,2-bis(4-pyridyl)ethylene.  
     
     
         4 . A compound according to  claim 1  wherein A is a radical of a compound represented by the formula  
       
         
           
           
               
               
           
         
       
       wherein 
 R 17 , R 19  and R 20  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, substituted oxygen, nitrogen, substituted nitrogen and substituted sulfur; and  
 R 18  is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, substituted oxygen and substituted nitrogen.  
 
     
     
         5 . A compound as defined in  claim 4  wherein A is a radical of a compound selected from the group consisting of 1 -benzylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-benzylbenzimidazole, 1-benzyl-2-methybenzimidazole, 1-(2-ethoxy-1-ethyl)benzimidazole, 1-(2-methoxy-1-ethyl)-2-methylbenzimidazole, 1-ethyl-2-phenylbenzimidazole, and 1-benzyl-2-(4-chlorophenyl)benzimidazole.  
     
     
         6 . A compound according to  claim 1  wherein A is a radical of a compound represented by the formula  
       
         
           
           
               
               
           
         
       
       wherein: 
 R 21  and R 22  are each independently selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, sulfonyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl,  
 or R 21  and R 22  taken together with the nitrogen atom to which they are attached form a heterocycloalkyl ring having four to eight members;  
 R 23  is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, substituted oxygen, substituted nitrogen and substituted sulfur,  
 or R 22  and R 23  taken together with the nitrogen and carbon atoms to which they are respectively attached form a heterocycloalkyl ring having four to eight members; and  
 X 6  is oxygen, sulfur or substituted nitrogen.  
 
     
     
         7 . A compound as defined in  claim 6  wherein A is a radical of a compound selected from the group consisting of N,N,N′,N′-tetramethylterephalamide, N,N,N′,N′-tetrabutylterephalamide, 1,4-dimethyl-2,3-dioxopiperazine, dimethylbenzamide, N-acetylindoline, N-propionylindoline, N-acetyl-5-bromoindoline, N-benzoylmorpholine, N-benzoylpyrollidine, N-benzoylpiperidine, N-acetyl-5-chloroindoline and N-phenylpyrolidinone.  
     
     
         8 . The imaging member comprising a first image-forming layer including a compound according to  claim 1 , said compound being in the crystalline form.  
     
     
         9 . The imaging member as defined in  claim 8  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.  
     
     
         10 . The imaging member as defined in  claim 9  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.  
     
     
         11 . The imaging member as defined in  claim 10  wherein said color-forming layers form magenta, cyan and yellow color, respectively.  
     
     
         12 - 16 . (canceled)