Photosensitive polyimide compositions

Patent metadata

Field	Value
Publication number	US-10036952-B2
Application number	US-201615132486-A
Country	US
Kind code	B2
Filing date	Apr 19, 2016
Priority date	Apr 21, 2015
Publication date	Jul 31, 2018
Grant date	Jul 31, 2018

Abstract

This disclosure relates to a photosensitive composition that includes at least one fully imidized polyimide polymer having a weight average molecular weight in the range of about 20,000 Daltons to about 70,000 Daltons; at least one solubility switching compound; at least one photoinitiator; and at least one solvent. The composition is capable of forming a film or a dry film having a dissolution rate of greater than about 0.15 micron/second using cyclopentanone as a developer.

First claim

What is claimed is:

1. A photosensitive composition, comprising:
at least one fully imidized polyimide polymer having a weight average molecular weight in the range of about 20,000 Daltons to about 70,000 Daltons, wherein the at least one fully imidized polyimide polymer is prepared from at least one diamine, and the at least one diamine comprises a compound selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib),

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 C 5 -C 7 cycloalkyl group;
at least one solubility switching compound;
at least one photoinitiator; and
at least one solvent;
wherein the composition is capable of forming a film having a dissolution rate of greater than about 0.15 micron/second using cyclopentanone as a developer.

2. The photosensitive composition of claim 1 , wherein the at least one diamine is selected from the group consisting of 1-(4-aminophenyl)-1,3,3-trimethylindan-5-amine, 1-(4-aminophenyl)-1,3,3-trimethyl-2H-inden-5-amine, 1-(4-aminophenyl)-1,3,3-trimethyl-indan-5-amine, [1-(4-aminophenyl)-1,3,3-trimethyl-indan-5-yl]amine, and 1-(4-aminophenyl)-2,3-dihydro-1,3,3-trimethyl-1H-inden-5-amine), 5-amino-6-methyl-1-(3′-amino-4′-methylphenyl)-1,3,3-trimethylindan, 4-amino-6-methyl-1-(3′-amino-4′-methylphenyl)-1,3,3-trimethylindan, 5,7-diamino-1,1-dimethylindan, 4,7-diamino-1,1-dimethylindan, 5,7-diamino-1,1,4-trimethylindan, 5,7-diamino-1,1,6-trimethylindan, and 5,7-diamino-1,1-dimethyl-4-ethylindan.

3. The photosensitive composition of claim 1 , wherein the at least one fully imidized polyimide polymer is prepared from at least one dianhydride, the at least one dianhydride comprising a compound selected from the group consisting of 2,2-[bis(3,4-dicarboxyphenyl)]hexafluoropropane dianhydride, 3,3′,4,4′-benzophenone tetracarboxylic dianhydride, 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride, and 3,3′,4,4′-diphenyl ether tetracarboxylic dianhydride.

4. The photosensitive composition of claim 3 , wherein the at least one fully imidized polyimide polymer is prepared from a fluorinated dianhydride.

5. The photosensitive composition of claim 4 , wherein the fluorinated dianhydride is selected from a group consisting of:

6. The photosensitive composition of claim 1 , wherein the at least one fully imidized polyimide polymer is prepared from at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib), and 2,2-[bis(3, 4-dicarboxyphenyl)] hexafluoropropane dianhydride.

7. The photosensitive composition of claim 1 , wherein the solubility switching compound comprises at least one functional group selected from the group consisting of a vinyl group, an allyl group, a vinyl ether group, a propenyl ether group, a (meth)acryloyl group, an a SiH group, and a thiol group.

8. The photosensitive composition of claim 7 , wherein the solubility switching compounds is selected from the group consisting of 1,6-hexanediol di(meth)acrylate, tetraethyleneglycol di(meth)acrylate, divinylbenzene, ethoxylated bisphenol-A-di(meth)acrylate, diethylene glycol bis(allyl carbonate), trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta-/hexa-(meth)acrylate, isocyanurate tri(meth)acrylate, bis(2-hydroxyethyl)-isocyanurate di(meth)acrylate, 1,3-butanediol tri(meth)acrylate, 1,4-butanediol tri(meth)acrylate, methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl(meth)acrylate, neopentyl glycol di(meth)acrylate, (meth)acrylate modified-urea-formaldehyde resins, (meth)acrylate modified melamine-formaldehyde resins and (meth)acrylate modified cellulose.

9. The photosensitive composition of claim 1 , wherein the developer and the at least one fully imidized polyimide polymer has a relative energy difference of from about 0.1 to about 3.

10. The photosensitive composition of claim 1 , wherein when an area of the film made from the composition is exposed to actinic radiation, the exposed area has a dissolution rate of less than about 0.02 microns/second in cyclopentanone.

11. The photosensitive composition of claim 1 , wherein the solubility switching compound increases a dissolution rate of the film in cyclopentanone compared to a film made from a photosensitive composition containing the same components without the solubility switching compound.

12. A photosensitive film formed from the photosensitive composition of claim 1 .

13. A process, comprising:
coating a substrate with the composition of claim 1 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.

14. The process of claim 13 , wherein the coated substrate is baked at a temperature from about 50° C. to about 200° C.

15. The process of claim 14 , further comprising exposing the dried film to radiation through a mask to form a coated substrate having a dried, patternwise exposed film.

16. The process of claim 15 , further comprising baking the dried, patternwise exposed film at a temperature from about 50° C. to about 150° C. in a second baking step.

17. The process of claim 16 , further comprising developing a portion of the dried, exposed film in a developer to produce a relief image on the substrate.

18. The process of claim 17 , further comprising rinsing the relief image on the substrate with a solvent or a mixture of solvents.

19. The process of claim 18 , 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.

20. A three dimensional object, comprising at least one patterned film formed by the process of claim 13 .

21. The three dimensional object of claim 20 , comprising patterned films in at least two stacks.

22. The three dimensional object of claim 20 , comprising patterned films in at least three stacks.

23. A semiconductor device, comprising the three dimensional object of claim 20 .

24. The semiconductor device of claim 23 , wherein the semiconductor device is an integrated circuit, a light emitting diode, a solar cell, or a transistor.

25. A dry film structure, comprising a carrier substrate, and a first polymeric layer supported by the carrier substrate, wherein the first polymeric layer is prepared from the photosensitive composition of claim 1 .

26. The dry film structure of claim 25 , further comprising a protective layer, wherein the first polymeric layer is between the carrier substrate and the protective layer.

27. The dry film structure of claim 25 , wherein the first polymeric layer has a film thickness of at most 5 microns.

28. The dry film structure of claim 26 , further comprising a second polymeric layer, wherein the second polymeric layer is between the first polymeric layer and the carrier substrate or the second polymeric layer is between the first po

Assignees

• Fujifilm Electronic Mat Usa Inc

Inventors

• Malik Sanjay
• Sakamuri Raj
• Dimov Ognian N
• De Binod B
• Reinerth William A
• Naiini Ahmad A

Classifications

• H10P76/204

  of organic photoresist masks · CPC title

• H10P50/28

  of insulating materials · CPC title

• H10P14/683

  carbon-based polymeric organic materials, e.g. polyimides, poly cyclobutene or PVC · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title

• G03F7/037 Primary

  the binders being polyamides or polyimides · CPC title