Photosensitive polyimide compositions
AssigneePromerus, LLC
InventorPRAMOD KANDANARACHCHI
Life of this patent
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Abstract
Embodiments in accordance with the present invention encompass photosensitive compositions containing a variety of soluble polyimide polymers and various additives including photoacid generator, photo radical generator and one or more photo crosslinking agents which are useful for forming films that can be patterned to create structures for microelectronic devices, microelectronic packaging, microelectromechanical systems, optoelectronic devices and displays. In some embodiments the compositions of this invention are shown to feature excellent hitherto unachievable mechanical properties. The negative images formed therefrom can be readily cured at lower temperatures than the conventional polyimides and exhibit improved thermo-mechanical properties, among other property enhancements.
Claims20
A process for forming a patterned film comprising:
- a) forming an organic solvent soluble end capped polyimide of formula (IA):
- wherein:
- m is an integer of at least 50;
- n is an integer from 1 to 12, inclusive;
- X is two distinct tetravalent organic groups, each of which is derived from a dianhydride selected from the group consisting of:
- Y is one or more distinct divalent organic group derived from a diamine selected from the group consisting of:
- R1 and R2 are the same or different and each independently of one another selected from the group consisting of hydrogen and linear or branched (C1-C16)alkyl;
- by reacting the dianhydride with the diamine and a compound of formula (II):
- wherein n, R1 and R2 are as defined above, all of which dissolved in N-methyl-2-pyrrolidone at ambient temperature to form a polyamic acid;
- reacting the polyamic acid dissolved in cyclopentanone with acetic anhydride in the presence of pyridine at a temperature of about 95° C. for about six hours in nitrogen atmosphere and cooling to form the polyimide of formula (IA), which is soluble in an organic solvent selected from the group consisting of N-methyl-2-pyrrolidone (NMP), γ-butyrolactone (GBL), N,N-dimethylacetamide (DMAc), propylene glycol monomethyl ether acetate (PGMEA), dimethyl sulfoxide (DMSO), cyclopentanone, cyclohexanone, 2-butanone and 2-heptanone and mixtures in any combination thereof;
- and
- wherein the amount of compound of formula (II) used to form the end capped polyimide of formula (IA) is about 2.5 mole percent or 3.4 mole percent based on total moles of dianhydride, diamine and compound of formula (II);
- and
- b) mixing a solution of the polyimide of formula (IA) with one or more additives selected from the group consisting of a photo radical generator, a photo acid generator and a crosslinking agent to form a composition;
- c) coating the composition on a suitable substrate;
- and
- d) exposing the coated substrate to a suitable actinic radiation through a mask;
- e) developing the exposed film in cyclopentanone;
- and
- f) curing the developed film at a temperature of about 170° C. to obtain the patterned film.
A process for forming a patterned film comprising:
- a) forming an organic solvent soluble end capped polyimide of formula (IB):
- wherein:
- m is an integer of at least 50;
- X is two distinct tetravalent organic groups, each of which is derived from a dianhydride selected from the group consisting of:
- Y is two distinct divalent organic groups, each of which is derived from a diamine selected from the group consisting of:
- each of R3 is independently selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C3-C6)alkyl;
- and
- by reacting the dianhydride with the diamine and a compound of formula (IV):
- wherein R3 is as defined above, all of which dissolved in N-methyl-2-pyrrolidone at room temperature to form a polyamic acid;
- reacting the polyamic acid dissolved in cyclopentanone with acetic anhydride in the presence of pyridine at a temperature of about 100° C. for about four to eight hours in nitrogen atmosphere and cooling to form the polyimide of formula (IB), which is soluble in an organic solvent selected from the group consisting of N-methyl-2-pyrrolidone (NMP), γ-butyrolactone (GBL), N,N-dimethylacetamide (DMAc), propylene glycol monomethyl ether acetate (PGMEA), dimethyl sulfoxide (DMSO), cyclopentanone, cyclohexanone, 2-butanone and 2-heptanone and mixtures in any combination thereof;
- and
- b) mixing a solution of the polyimide of formula (IB) with one or more additives selected from the group consisting of a photo radical generator, a photo acid generator and a crosslinking agent to form a composition;
- c) coating the composition on a suitable substrate;
- and
- d) exposing the coated substrate to a suitable actinic radiation through a mask;
- e) developing the exposed film in cyclopentanone;
- and
- f) curing the developed film at a temperature of about 170° C. to obtain the patterned film.
Dependencies are inferred from the claim text.