Photosensitive polyimide compositions

a polyimide and composition technology, applied in the field of photosensitive polyimide compositions, can solve the problems of poor photo imaging capability, insolubility of polyimides and/or precursor polyamic acids in commonly used solvents in the electronic industry, and many not suitable for many applications, and achieve excellent thermomechanical properties

Pending Publication Date: 2020-09-10
PROMERUS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0008]Surprisingly, it has now been found that various polyimides that are soluble in commonly used organic solvents can be used in forming photosensitive compositions as described herein that provide hitherto unattainable thermo-mechanical properties. More specifically, the photosensitive compositions as described herein contain a mixture of either a soluble polyimide or a suitably end capped polyimide in combination with at least one photoacid generator, at least one photo radical generator, and one or more crosslinking agents. The end capped polyimides as employed in the composition of this invention can be made by either end capping the amino end group of the polyimide with a suitable mono-anhydride or by end capping the anhydride end group of the polyimide with a suitable mono-amine. The photosensitive compositions of this invention feature excellent thermo-mechanical properties and can be cured at temperatures lower than 200° C.

Problems solved by technology

However, most of the polyimides disclosed in the art are generally for positive tone image forming films, and many not be suitable for many applications.
Some of the drawbacks include use of highly toxic and corrosive phenolic monomers which provide alkali solubility that is required for forming positive tone compositions.
Other property disadvantages include insolubility of the polyimides and / or the precursor polyamic acids in commonly used solvents in the electronic industry, poor photo imaging capabilities, among others.
Even more importantly, such compositions suffer from poor thermo-mechanical properties and may require high cure temperatures, often times higher than 300° C., which are undesirable.

Method used

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  • Photosensitive polyimide compositions
  • Photosensitive polyimide compositions
  • Photosensitive polyimide compositions

Examples

Experimental program
Comparison scheme
Effect test

example 1

6FDA / PMDA / 6BF / PFMB (25 / 25 / 30 / 20)

[0209]6BF (15.13 g, 30 mmol) and PFMB (6.41 g, 20 mmol) were dissolved in NMP (152.4 g) and stirred at ambient temperature under a nitrogen atmosphere. To this solution was then added a mixture of 6FDA (11.11 g, 25 mmol) and PMDA (5.45 g, 25 mmol) in small batches while stirring that generated about 5° C. exotherm. After which time the reaction mixture was continued to stir at ambient temperature for 20 hours during which time the solution turned viscous indicating the formation of polyamic acid. To this viscous solution additional amount of NMP (184 g) was added and a small portion of which was characterized by GPC (GPC-DMAc—Mw=258,950, Mn=124,450, PDI=2.08).

[0210]The polyamic acid solution as obtained above (236 g containing 23.6 g polymer) was mixed with anhydrous pyridine (23.9 g), acetic anhydride (24 g) and cyclopentanone (60.6 g) and the solution heated to 95° C. for 4 hours under nitrogen atmosphere while stirring. The reaction mixture was all...

example 2

6FDA / PMDA / 6BF / PFMB / DMMIEt-NH2 (24.7 / 24.7 / 29 / 19.1 / 2.5)

[0211]6BF (14.82 g, 29.4 mmol), PFMB (6.21 g, 19.4 mmol) and DMMIEt-NH2 (0.42 g, 2.5 mmol) were dissolved in NMP (152 g) and stirred at ambient temperature under a nitrogen atmosphere. To this solution was then added a mixture of 6FDA (11.11 g, 25 mmol) and PMDA (5.45 g, 25 mmol) in small batches while stirring. The reaction mixture was stirred at ambient temperature for 20 hours during which time the solution became viscous. To this viscous solution was then added NMP (72 g). A small portion of this solution was further diluted with DMAc for GPC analysis. GPC-DMAc—Mw=131,500, Mn=72,550, PDI=1.81. A small sample of the polymer solution was added to excess water / acetone (80 / 20) mixture to isolate the polymer. The gummy product was washed with excess water / acetone (80 / 20) mixture and dried in a vacuum oven at 50-60° C. for 24 hours to obtain a solid product, which was characterized by 1H NMR. 1H-NMR (500 MHz) spectra of this product...

example 3

6FDA / PMDA / 6BF / PFMB / DMMIEt-NH2 (24.7 / 24.7 / 29.0 / 19.1 / 2.5)

[0213]6BF (17.78 g, 35.3 mmol), PFMB (7.45 g, 23.3 mmol) and DMMIEt-NH2 (0.51 g, 3 mmol) were dissolved in NMP (182.4 g) and stirred at ambient temperature under a nitrogen atmosphere. A mixture of 6FDA (13.33 g, 30 mmol) and PMDA (6.54 g, 30 mmol) was then added in small batches to the above solution while stirring. The reaction mixture was stirred at ambient temperature for 20 hours during which time the solution turned viscous. An additional amount of NMP (62 g) was added to this viscous solution. A small portion of this solution was further diluted with DMAc for GPC analysis. GPC-DMAc—Mw=121,150, Mn=69,500, PDI=1.74. A small sample of this polymer solution was also added to excess water / acetone (80 / 20) mixture to isolate the polymer. The gummy product was washed with excess water / acetone (80 / 20) mixture and dried in a vacuum oven at 50-60° C. for 24 hours to obtain a solid product, which was characterized by 1H NMR. 1H-NMR (...

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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.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Application No. 62 / 813,940, filed Mar. 5, 2019, which is incorporated herein by reference in its entirety.BACKGROUND OF THE INVENTIONField of the Invention[0002]The present invention relates to photosensitive polyimide compositions. More specifically, the present invention relates to photosensitive compositions containing a series of polyimides and reactive end group capped polyimides. Even more specifically, the photosensitive compositions as described herein contain a mixture of either a soluble polyimide or a suitably end capped polyimide in combination with at least one photoacid generator, at least one photo radical generator, and one or more crosslinking agents. The compositions of this invention are useful for forming microelectronic and / or optoelectronic devices and assemblies thereof, and more specifically, such compositions exhibit improved thermal, mechanical and opto-elec...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G03F7/038C08G73/10C08G73/12G03F7/004
CPCC08G73/1085C08G73/1025C08G73/101C08G73/124C08G73/122G03F7/0045G03F7/0387C08G73/1032C08L79/08C08K5/0025C08G73/1039C08G73/1067C08G73/1042G03F7/037G03F7/031G03F7/029C08L33/14C08L63/00
Inventor KANDANARACHCHI, PRAMOD
Owner PROMERUS LLC
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