Oxime ester compound and photopolymerization initiator containing the same

Abstract

Disclosed is an oxime ester compound represented by the following general formula (I). (In the formula, R 1 , R 2 and R 3 independently represent R 11 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 or CN; R 11 , R 12 and R 13 Independently represent a hydrogen atom, an alkyl group having 1-20 carbon atoms, an aryl group having 6-30 carbon atoms, an arylalkyl group having 7-30 carbon atoms or a heterocyclic group having 2-20 carbon atoms; R 4 and R 5 independently represent R 11 , OR 11 , SR 11 , COR 11 , CONR 12 R 13 , NR 12 COR 11 , OCOR 11 , COOR 11 , SCOR 11 , OCSR 11 , COSR 11 , CSOR 11 , CN, a halogen atom or a hydroxy group; and a and b independently represent a number of 0-3.)

1 - 13 . (canceled) 
   
   
       14 . An oxime ester compound represented by general formula (I): 
     
       
         
         
             
             
         
       
     
     wherein R 1 , R 2 , and R 3  each independently represent R l1 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 , or CN; R 11 , R 12 , and R 13  each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, in which the alkyl group, aryl group, arylalkyl group, and heterocyclic group may have their hydrogen atom substituted with OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , —NR 22 —OR 23 , —NCOR 22 —OCOR 23 , —C(═N—OR 21 )—R 22 , —C(═N—OCOR 21 )—R 22 , CN, a halogen atom, —CR 21 ═CR 22 R 23 , —CO—CR 21 CR 22 R 23 , a carboxyl group, or an epoxy group; R 21 , R 22 , and R 23  each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; the methylene units of the alkylene moiety of the substituents represented by R 11 , R 12 , R 13 , R 21 , R 22 , and R 23  may be interrupted by an unsaturated linkage, an ether linkage, a thioether linkage, an ester linkage, a thioester linkage, an amide linkage, or a urethane linkage at 1 to 5 sites thereof; the alkyl moiety of the substituents represented by R 11 , R 12 , R 13 , R 21 , R 22 , and R 23  may be branched or cyclic; an alkyl terminal of the substituents represented by R 11 , R 12 , R 13 , R 21 , R 22 , and R 23  may have an unsaturated bond; R 12  and R 13 , and R 22  and R 23  may be connected to each other form a ring; R 3  may be taken together with a neighboring benzene ring; R 4  and R 5  each independently represent R 11 , OR 11 , SR 11 , COR 11 , CONR 12 R 13 , NR 12 COR 11 , OCOR 11 , COOR 11 , SCOR 11 , OCSR 11 , COSR 11 , CSOR 11 , CN, a halogen atom, or a hydroxyl group; and a and b each independently represent 0 to 3. 
   
   
       15 . The oxime ester compound according to claim  1 , wherein R 1  is an alkyl group having 11 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, an arylalkyl group with 7 to 30 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, OR 11 , COR 11 , SR 11 , CONR 12 R 13 , or CN; or R 3  is an alkyl group having 1 to 12 carbon atoms interrupted by an ether linkage or an ester linkage at 1 to 5 sites thereof, an alkyl group having 13 to 20 carbon atoms, OR 11 , COR 11 , SR 11 , CONR 12 R 13 , or CN; and R 11 , R 12 , and R 13  each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; the alkyl group, aryl group, arylalkyl group, and heterocyclic group as represented by R 1 , R 3 , R 11 , R 12 , and R 13  may have their hydrogen atom substituted with OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , —NR 22 —OR 23 , —NCOR 22 —OCOR 23 , —C(═N—OR 21 )—R 22 , —C(═N—OCOR 21 )—R 22 ,CN, a halogen atom, —CR 21 ═CR 22 R 23 , —CO—CR 21 ═CR 22 R 23 , a carboxyl group, or an epoxy group; R 21 , R 22 , and R 23  each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; the methylene units of the alkylene moiety of the substituents represented by R 1 , R 3 , R 11 , R 12 , R 13 , R 21 , R 22 , and R 23  may be interrupted by an unsaturated linkage, an ether linkage, a thioether linkage, an ester linkage, a thioester linkage, an amide linkage, or a urethane linkage at 1 to 5 sites thereof; the alkyl moiety of the substituents represented by R 1 , R 3 , R 11 , R 12 , R 13 , R 21 , R 22 , and R 23  may be branched or cyclic; the alkyl terminal of the substituents represented by R 1 , R 3 , R 11 , R 12 , R 13 , R 21 , R 22 , and R 23  may have an unsaturated bond; R 12  and R 13  may be connected to form a ring; and R 3  may be taken together with a neighboring benzene ring. 
   
   
       16 . The oxime ester compound according to  claim 14 , wherein R 1  is an alkyl group having 11 to 20 carbon atoms or an aryl group with 6 to 30 carbon atoms; the alkyl group and the aryl group as represented by R 1  may have their hydrogen atom substituted with OR 21 , COR 21 , SR 21 , NR 22 R 23 , CON 22 R 23 , —NR 22 —OR 23 , —NCOR 22 —OCOR 23 , —C(═N—OR 21 )—R 22 , —C(═N—OCOR 21 )—R 22 , CN, a halogen atom, —CR 21 ═CR 22 R 23 , —CO—CR 21 ═CR 22 R 23 , a carboxyl group, or an epoxy group; R 21 , R 22 , and R 23  each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; the methylene units of the alkylene moiety of the substituents represented by R 1 , R 21 , R 22 , and R 23  may be interrupted by an unsaturated linkage, an ether linkage, a thioether linkage, an ester linkage, a thioester linkage, an amide linkage, or a urethane linkage at 1 to 5 sites thereof; the alkyl moiety of the substituents represented by R 1 , R 21 , R 22 , and R 23  may be branched or cyclic; the alkyl terminal of the substituents represented by R 1 , R 21 , R 22 , and R 23  may have an unsaturated bond. 
   
   
       17 . The oxime ester compound according to  claim 14 , wherein R 3  is a branched alkyl group having 8 or more carbon atoms the methylene units of which may be interrupted by an ether linkage or an ester linkage at 1 to 5 sites thereof. 
   
   
       18 . The oxime ester compound according to  claim 14 , wherein R 3  is an alkyl group having 13 or more carbon atoms the methylene units of which may be interrupted by an ether linkage or an ester linkage at 1 to 5 sites thereof. 
   
   
       19 . The oxime ester compound according to  claim 14 , wherein R 3  is an alkyl group interrupted by an ether linkage at 1 to 5 sites thereof. 
   
   
       20 . The oxime ester compound according to  claim 14 , wherein R 3  is an alkyl group interrupted by an ester linkage at 1 to 5 sites thereof. 
   
   
       21 . The oxime ester compound according to  claim 14 , which dissolves in propylene glycol-1-monomethyl ether-2-acetate or cyclohexanone to a concentration of 1% by mass or more. 
   
   
       22 . A photopolymerization initiator comprising the oxime ester compound according to  claim 14  as an active ingredient. 
   
   
       23 . A photosensitive composition comprising the photopolymerization initiator according to  claim 22  and a polymerizable compound having an ethylenically unsaturated bond. 
   
   
       24 . The photosensitive composition according to  claim 23 , further comprising an inorganic compound. 
   
   
       25 . An alkali-developable photosensitive resin composition comprising the photopolymerization initiator according to  claim 22  and an alkali-developable compound having an ethylenically unsaturated compound. 
   
   
       26 . A colored alkali-developable photosensitive resin composition comprising the alkali-developable photosensitive resin composition according to  claim 22  and a colorant. 
   
   
       27 . The oxime ester compound according to  claim 15 , wherein R 1  is an alkyl group having 11 to 20 carbon atoms or an aryl group with 6 to 30 carbon atoms; the alkyl group and the aryl group as represented by R 1  may have their hydrogen atom substituted with OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , —NR 22 —OR 23 , —NCOR 22 —OCOR 23 , —C(═N—OR 21 )—R 22 , —C(═N—OCOR 21 )—R 22 , CN, a halogen atom, —CR 21 ═CR 22 R 23 , —CO—CR 21 CR 22 R 23 , a carboxyl group, or an epoxy group; R 21 , R 22 , and R 23  each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; the methylene units of the alkylene moiety of the substituents represented by R 1 , R 21 , R 22 , and R 23  may be interrupted by an unsaturated linkage, an ether linkage, a thioether linkage, an ester linkage, a thioester linkage, an amide linkage, or a urethane linkage at 1 to 5 sites thereof; the alkyl moiety of the substituents represented by R 1 , R 21 , R 22 , and R 23  may be branched or cyclic; the alkyl terminal of the substituents represented by R 1 , R 21 , R 22 , and R 23  may have an unsaturated bond. 
   
   
       28 . The oxime ester compound according to  claim 15 , wherein R 3  is a branched alkyl group having 8 or more carbon atoms the methylene units of which may be interrupted by an ether linkage or an ester linkage at 1 to 5 sites thereof. 
   
   
       29 . The oxime ester compound according to  claim 16 , wherein R 3  is a branched alkyl group having 8 or more carbon atoms the methylene units of which may be interrupted by an ether linkage or an ester linkage at 1 to 5 sites thereof. 
   
   
       30 . The oxime ester compound according to  claim 15 , wherein R 3  is an alkyl group having 13 or more carbon atoms the methylene units of which may be interrupted by an ether linkage or an ester linkage at 1 to 5 sites thereof. 
   
   
       31 . The oxime ester compound according to  claim 16 , wherein R 3  is an alkyl group having 13 or more carbon atoms the methylene units of which may be interrupted by an ether linkage or an ester linkage at 1 to 5 sites thereof. 
   
   
       32 . The oxime ester compound according to  claim 15 , wherein R 3  is an alkyl group interrupted by an ether linkage at 1 to 5 sites thereof. 
   
   
       33 . The oxime ester compound according to  claim 16 , wherein R 3  is an alkyl group interrupted by an ether linkage at 1 to 5 sites thereof.