Polyimides

Abstract

This disclosure relates to a polyimide polymer that includes the reaction product of: (a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib), [insert formula here] (la) or [insert formula here] (lb), (b) at least one diamine of Structure (II), (c) at least one tetracarboxylic acid dianhydride, and optionally (d) at least one compound containing a first functional group reactive with an amine or an anhydride and at least a second functional group selected from the group consisting of a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group. Each variable in the above formulas is defined in the specification.

1 . A polyimide polymer, comprising the reaction product of components (a), (b), (c), and optionally (d), wherein components (a), (b), (c), and (d) are:
 (a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib):   
       
         
           
           
               
               
           
         
         (b) at least one diamine of Structure (II): 
       
       
         
           
           
               
               
           
         
         (c) at least one tetracarboxylic acid dianhydride, and 
         optionally (d) at least one compound comprising a first functional group reactive with an amine or an anhydride and at least a second functional group selected from the group consisting of a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group, 
         wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , and R 14  independently, is H, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted C 5 -C 7  cycloalkyl group, and R 15  is methyl, a substituted or unsubstituted C 2 -C 40  linear, branched, cyclic, or polycyclic aliphatic group that optionally contains one or more oxygen, sulfur, or nitrogen atoms, or a mixture thereof; a substituted or unsubstituted C 6 -C 30  aryl; or a substituted or unsubstituted C 5 -C 30  heteroaryl containing one or more oxygen, sulfur, or nitrogen atoms, or a mixture thereof. 
       
     
     
         2 . The polymer of  claim 1 , wherein component (a) is at least one diamine of Structure (Ia). 
     
     
         3 . The polymer of  claim 2 , wherein the amino group on the indane ring in Structure (Ia) is at the 5 position and the other amino group in Structure (Ia) is at the 4 position. 
     
     
         4 . The polymer of  claim 3 , wherein each of R 1 , R 2 , and R 3  is CH 3  and each of R 4  and R 5  is H. 
     
     
         5 . The polymer of  claim 1 , wherein the diamine of Structure (II) is a diamine of Structure (IIa): 
       
         
           
           
               
               
           
         
         wherein z is an integer ranging from 0 to 12, and R 20  and R 21  are independently a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group. 
       
     
     
         6 . The polymer of  claim 1 , wherein diamine of Structure (II) is a diamine of Structure (IIb): 
       
         
           
           
               
               
           
         
         wherein R 20  is a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group, R 22  is a substituted or unsubstituted C 1 -C 6  linear or branched alkylene group, and R 23  is a substituted or unsubstituted C 1 -C 20  linear or branched alkyl group or a C 6 -C 20  substituted or unsubstituted aryl group. 
       
     
     
         7 . The polymer of  claim 1 , wherein the diamine of Structure (II) is a diamine of Structure (IIc): 
       
         
           
           
               
               
           
         
         wherein R 20  is a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group; R 22  a substituted or unsubstituted C 1 -C 6  linear or branched alkylene group; R 24  is a O or S atom, —NR 25 —, —CH(R 25 )—, or —(CH 3 ) 2 —, in which R 25  is a C 1 -C 6  substituted or unsubstituted linear or branched alkyl group. 
       
     
     
         8 . The polymer of  claim 1 , wherein the diamine of Structure (II) is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         9 . The polymer of  claim 1 , wherein the molar ratio of components (a) and (b) to component (c) ranges from 1.01 and 1.4. 
     
     
         10 . The polymer of  claim 1 , wherein the molar ratio of components (a) and (b) to component (c) ranges from 0.8 and 0.99. 
     
     
         11 . A polyamic acid polymer, comprising the reaction product of components (a), (b), (c), and optionally (d), wherein components (a), (b), (c), and (d) are:
 (a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib):   
       
         
           
           
               
               
           
         
         (b) at least one diamine of Structure (II): 
       
       
         
           
           
               
               
           
         
         (c) at least one tetracarboxylic acid dianhydride, and 
         optionally (d) at least one compound containing a first functional group reactive with an amine or an anhydride and at least a second functional group selected from the group consisting of a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group, 
         wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , and R 14  independently, is H, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted C 5 -C 7  cycloalkyl group, and R 15  is methyl, a substituted or unsubstituted C 2 -C 40  linear, branched, cyclic, or polycyclic aliphatic group that optionally contains one or more oxygen, sulfur, or nitrogen atoms, or a mixture thereof; a substituted or unsubstituted C 6 -C 30  aryl; or a substituted or unsubstituted C 5 -C 30  heteroaryl containing one or more oxygen, sulfur, or nitrogen atoms, or a mixture thereof. 
       
     
     
         12 . The polyamic acid polymer of  claim 11 , wherein the diamine of Structure (II) is a diamine of Structure (IIa): 
       
         
           
           
               
               
           
         
         wherein z is an integer ranging from 0 to 12, and R 20  and R 21  are independently a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group. 
       
     
     
         13 . The polyamic acid polymer of  claim 11 , wherein the diamine of Structure (II) is a diamine of Structure (IIb): 
       
         
           
           
               
               
           
         
         wherein R 20  is a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group, R 22  is a substituted or unsubstituted C 1 -C 6  linear or branched alkylene group, and R 23  is a substituted or unsubstituted C 1 -C 20  linear or branched alkyl group or a C 6 -C 20  substituted or unsubstituted aryl group. 
       
     
     
         14 . The polyamic acid polymer of  claim 11 , wherein the diamine of Structure (II) is a diamine of Structure (IIc): 
       
         
           
           
               
               
           
         
         wherein R 20  is a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear a branched alkyl group, or substituted or unsubstituted phenyl group; R 22  a substituted or unsubstituted C 1 -C 6  linear or branched alkylene group; and R 24  is a O or S atom, —NR 25 —, —CH(R 25 )—, or —(CH 3 ) 2 —, in which R 25  is C 1 -C 6  substituted or unsubstituted linear or branched alkyl group. 
       
     
     
         15 . The polyamic acid polymer of  claim 11 , wherein the diamine of Structure (II) is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         16 . A composition, comprising:
 (A) at least one polyimide polymer comprising the reaction product of:
 (a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib): 
   
       
         
           
           
               
               
           
         
         
           (b) at least one diamine of Structure (II): 
         
       
       
         
           
           
               
               
           
         
         
           (c) at least one tetracarboxylic acid dianhydride, and 
           optionally (d) at least one compound containing a first functional group reactive with an amine or an anhydride and at least one second functional group selected from a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group; 
         
         in which each of R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , and R 14  independently, is H, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted C 5 -C 7  cycloalkyl group, and R 15  is methyl, substituted or unsubstituted C 2 -C 40  linear, branched, cyclic, or polycyclic aliphatic group that optionally contains one or more oxygen, sulfur, or nitrogen atoms, or a mixture thereof; a substituted or unsubstituted C 6 -C 30  aryl group; or a substituted or unsubstituted C 5 -C 30  heteroaryl containing one or more oxygen, sulfur, or nitrogen atoms or a mixture thereof; 
         with the proviso that if (d) is not employed, the diamine of Structure (II) is selected from the group consisting of Structures (IIa), (IIb), and (IIc), 
       
       
         
           
           
               
               
           
         
       
       wherein z is an integer ranging from 0 to 12, R 20  and R 21  are independently a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group, R 22  is a substituted or unsubstituted C 1 -C 6  linear or branched alkylene group, R 23  is a substituted or unsubstituted C 1 -C 20  linear or branched alkyl group or a C 6 -C 20  substituted or unsubstituted aryl group, and R 24  is a O or S atom, —NR 25 —, —CH(R 25 )—, or —(CH 3 ) 2 —, in which R 25  is C 1 -C 6  substituted or unsubstituted linear or branched alkyl group;
 (B) at least one reactive functional compound (RFC) having at least one functional group capable of reacting with a substituted or unsubstituted alkenyl group or a substituted or unsubstituted alkynyl group on the polyimide polymer; 
 (C) an initiator capable of initiating a reaction between the substituted or unsubstituted alkenyl group or a substituted or unsubstituted alkynyl group on the polyimide polymer and the RFC; and 
 (D) at least one solvent. 
 
     
     
         17 . The compositions of  claim 16 , wherein the diamine of Structure (II) is a diamine of Structure (IIa): 
       
         
           
           
               
               
           
         
         wherein z is an integer ranging from 0 to 12, and R 20  and R 21  are independently a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group. 
       
     
     
         18 . The compositions of  claim 16 , wherein the diamine of Structure (II) is a diamine of Structure (IIb): 
       
         
           
           
               
               
           
         
         wherein R 20  is a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group, R 22  is a substituted or unsubstituted C 1 -C 6  linear or branched alkylene group, and R 23  is a substituted or unsubstituted C 1 -C 20  linear or branched alkyl group or a C 6 -C 20  substituted or unsubstituted aryl group. 
       
     
     
         19 . The compositions of  claim 16 , wherein the diamine of Structure (II) is a diamine of Structure (IIc) 
       
         
           
           
               
               
           
         
         wherein R 20  is a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group; R 22  a substituted or unsubstituted C 1 -C 6  linear or branched alkylene group; and R 24  is a O or S atom, —NR 25 —, —CH(R 25 )—, or —(CH 3 ) 2 —, in which R 25  is a C 1 -C 6  substituted or unsubstituted linear or branched alkyl group. 
       
     
     
         20 . The compositions of  claim 16 , wherein the diamine of Structure (II) is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         21 . A process, comprising:
 coating a substrate with the composition of  claim 16  to form a coated substrate having a film on the substrate, and   baking the coated substrate to form a coated substrate having a dried film.   
     
     
         22 . The process of  claim 21 , wherein the coated substrate is baked at a temperature from about 50° C. to about 200° C. 
     
     
         23 . The process of  claim 22 , further comprising exposing the dried film to radiation through a mask to form a coated substrate having a dried, patternwise exposed film. 
     
     
         24 . The process of  claim 23 , further comprising baking the dried, patternwise exposed film at a temperature from about 50° C. to about 150° C. in a second baking step. 
     
     
         25 . The process of  claim 24 , further comprising developing a portion of the dried, exposed film in a developer to produce a relief image on the substrate. 
     
     
         26 . The process of  claim 25 , further comprising rinsing the relief image on the substrate with a solvent or a mixture of solvents. 
     
     
         27 . The process of  claim 26 , further comprising baking the substrate having a relief image at a temperature from about 50° C. to about 200° C. in a third baking step. 
     
     
         28 . An article formed by the process of  claim 21 , wherein the article is a semiconductor substrate, a flexible film for electronics, a wire isolation, a wire coating, a wire enamel, or an inked substrate. 
     
     
         29 . A semiconductor device, comprising the article of  claim 28 . 
     
     
         30 . The semiconductor device of  claim 29 , wherein the semiconductor device is an integrated circuit, a light emitting diode, a solar cell, and a transistor. 
     
     
         31 . A dry film structure, comprising a carrier substrate, a protective layer, and a polymeric layer between the carrier substrate and the protective layer, wherein the polymeric layer contains:
 (A) at least one polyimide polymer comprising the reaction product of:
 (a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib): 
   
       
         
           
           
               
               
           
         
         
           (b) at least one diamine of Structure (II): 
         
       
       
         
           
           
               
               
           
         
         
           (c) at least one tetracarboxylic acid dianhydride, and 
           optionally (d) at least one compound containing a first functional group reactive with an amine or an anhydride and at least one second functional group selected from a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group; 
         
         in which each of R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , and R 14  independently, is H, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted C 5 -C 7  cycloalkyl group, and R 15  is methyl, a substituted or unsubstituted C 2 -C 40  linear, branched, cyclic, or polycyclic aliphatic group that optionally contains one or more oxygen, sulfur, or nitrogen atoms, or a mixture thereof; a substituted or unsubstituted C 6 -C 30  aryl; or a substituted or unsubstituted C 6 -C 30  heteroaryl containing one or more oxygen, sulfur, or nitrogen atoms, or a mixture thereof, 
         with the proviso that if (d) is not employed, the diamine of Structure (II) is selected from the group consisting of Structures (IIa), (IIb), and (IIc): 
       
       
         
           
           
               
               
           
         
       
       wherein z is an integer ranging from 0 to 12, R 20  and R 2′  are independently a hydrogen atom, a substituted or unsubstituted C 1 -C 6  linear or branched alkyl group, or a substituted or unsubstituted phenyl group, R 22  is a substituted or unsubstituted C 1 -C 6  linear or branched alkylene group, R 23  is a substituted or unsubstituted C 1 -C 20  linear or branched alkyl group or a C 6 -C 20  substituted or unsubstituted aryl group, and R 24  is a O or S atom, —NR 25 —, —CH(R 25 )—, or —(CH 3 ) 2 —, in which R 25  is C 1 -C 6  substituted or unsubstituted linear or branched alkyl group;
 (B) at least one reactive functional compound (RFC) having at least one functional group capable of reacting with a substituted or unsubstituted alkenyl group or a substituted or unsubstituted alkynyl group on the polyimide polymer; and 
 (C) an initiator capable of initiating a reaction between the substituted or unsubstituted alkenyl group or a substituted or unsubstituted alkynyl group on the polyimide polymer and the RFC. 
 
     
     
         32 . A process, comprising:
 (a) removing the protective layer from the dry film structure of  claim 31 ;   (b) applying the structure obtained in step (a) onto an electronic substrate to form a laminate.   
     
     
         33 . The process of  claim 32 , further comprising exposing the polymeric layer in the laminate to actinic radiation. 
     
     
         34 . The process of  claim 33 , further comprising removing the carrier substrate before or after exposing the polymeric layer. 
     
     
         35 . The process of  claim 34 , further comprising removing unexposed portions in the polymeric layer by using a developer. 
     
     
         36 . The process of  claim 35 , further comprising curing the remaining polymeric layer. 
     
     
         37 . An article formed by the process of  claim 32 , wherein the article is a semiconductor substrate, a flexible film for electronics, a wire isolation, a wire coating, a wire enamel, or an inked substrate. 
     
     
         38 . An electronic device, comprising the article of  claim 37 . 
     
     
         39 . The electronic device of  claim 38 , wherein the electronic device is an integrated circuit, a light emitting diode, a solar cell, or a transistor.