Photosensitive compositions, color filter and microlens derived therefrom

Patent metadata

Field	Value
Publication number	US-10915019-B2
Application number	US-201815937924-A
Country	US
Kind code	B2
Filing date	Mar 28, 2018
Priority date	Mar 28, 2017
Publication date	Feb 9, 2021
Grant date	Feb 9, 2021

Abstract

Embodiments in accordance with the present invention encompass self-imagable polymer compositions containing a colorant which are useful for forming films that can be patterned to create structures for color filters and microlens having applications in a variety of microelectronic devices, optoelectronic devices and displays, such as for example image sensors. The compositions of this invention can be tailored to form positive tone images for forming an array of images, which can be thermally transformed into an array of microlens. The images thus formed can then be used in color filter applications.

First claim

What is claimed is:

1. A composition comprising:
a) a polymer having one or more first repeating units represented by formula (IA), said first repeating unit is derived from a monomer of formula (I):

wherein:
m is an integer 0, 1 or 2;
R 1 , R 2 , R 3 and R 4 are the same or different and each independently selected from the group consisting of hydrogen, halogen, linear or branched (C 1 -C 12 )alkyl, hydroxy(C 1 -C 12 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 6 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, (C 5 -C 10 )heteroaryl, (C 5 -C 10 )heteroaryl(C 1 -C 3 )alkyl, hydroxy, (C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy(C 1 -C 3 )alkyl, (C 5 -C 10 )heteroaryloxy(C 1 -C 3 )alkyl, (C 6 -C 10 )aryloxy, (C 5 -C 10 )heteroaryloxy,
(C 1 -C 6 )acyloxy, —(CH 2 ) a —C(CF 3 ) 2 OR, —(CH 2 ) a —CO 2 R,

wherein:
a is an integer from 0 to 4
b is an integer from 0 to 10;
c is an integer 0, 1, 2, 3 or 4; and
R is selected from the group consisting of hydrogen, linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl and (C 7 -C 12 )aralkyl; and
one or more of a second repeating unit represented by formula (IIA) or (IIB), said second repeating unit is derived from a monomer of formula (II):

wherein:
Z is O or N—R 8 wherein R 8 is selected from the group consisting of hydrogen, linear or branched (C 1 -C 9 )alkyl, (C 3 -C 7 )cycloalkyl and (C 6 -C 12 )aryl;
R 5 , R 6 and R 7 are each independently of one another selected from the group consisting of hydrogen, linear or branched (C 1 -C 9 )alkyl, fluorinated or perfluorinated(C 1 -C 9 )alkyl, (C 6 -C 12 )aryl and (C 6 -C 12 )aryl(C 1 -C 12 )alkyl; and
wherein each of aforementioned groups, where valence is permissible, is optionally substituted with one or more groups selected from the group consisting of linear or branched (C 1 -C 6 )alkyl, (C 3 -C 7 )cycloalkyl, (C 1 -C 6 )perfluoroalkyl, (C 1 -C 6 )alkoxy, (C 3 -C 7 )cycloalkoxy, (C 1 -C 6 )perfluoroalkoxy, halogen, hydroxy, linear or branched hydroxy(C 1 -C 6 )alkyl, acetoxy, phenyl, hydroxyphenyl and acetoxyphenyl;
b) a dye selected from the group consisting of red, green, blue, yellow, magenta, black and cyan colored dye material;
c) a photoactive compound; and
d) a carrier solvent.

2. The composition of claim 1 , wherein Z is O, R 5 and R 6 are hydrogen, and R 7 is hydrogen or linear or branched (C 1 -C 9 )alkyl.

3. The composition of claim 1 , wherein m=0, R 1 , R 2 , R 3 and R 4 independently represents hydrogen, hexyl,
decyl, —(CH 2 ) 2 —C(CF 3 ) 2 OH, —(CH 2 ) 2 —CO 2 H, benzyl and phenethyl.

4. The composition of claim 1 , wherein the polymer comprises one or more first repeat units derived from the corresponding monomers selected from the group consisting of:
bicyclo[2.2.1]hept-2-ene (NB);
norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol (HFANB);
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB); and
(NBTON).

5. The composition of claim 1 , wherein the polymer comprises one or more second repeat units derived from the corresponding monomers selected from the group consisting of:
maleic anhydride; and
2-methyl-maleic anhydride.

6. The composition of claim 1 , wherein the polymer is selected from the group consisting of:
a copolymer containing repeating units derived from 5-phenethylbicyclo[2.2.1]hept-2-ene and ring opened maleic anhydride repeat units which is ring opened with methanol;
a copolymer containing repeating units derived from bicyclo[2.2.1]hept-2-ene and ring opened maleic anhydride repeat units which is ring opened with n-butanol;
a terpolymer containing repeating units derived from 5-phenethylbicyclo[2.2.1]hept-2-ene, 5-decylbicyclo[2.2.1]hept-2-ene and ring opened maleic anhydride repeat units which is ring opened with methanol; and
a copolymer containing repeating units derived from 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB) and ring opened maleic anhydride repeat units which is ring opened with n-butylamine.

7. The composition of claim 1 , wherein the dye is selected from the group consisting of solvent dye, disperse dye, acid dye, basic dye, sulfur dye and vat dye.

8. The composition of claim 7 , wherein the dye is miscible in the composition.

9. The composition of claim 1 , wherein the dye is selected from the group consisting of:

10. The composition of claim 1 , wherein the photoactive compound comprises moiety selected from the group consisting of a 1,2-naphthoquinonediazide-5-sulfonyl moiety, a 1,2-naphtoquinonediazide-4-sulfonyl moiety as represented by structural formulae (IIIa) and (IIIb), respectively:

and a sulfonyl benzoquinone diazide represented by structural formula (IIIc).

11. The composition according to claim 1 , wherein the photoactive compound is

wherein at least one of Q is a group of formula (IIIa) or (IIIb):

and the remaining Q is hydrogen.

12. The composition according to claim 1 , which further comprises one or more crosslinking agents selected from the group consisting of:

13. The composition according to claim 1 , wherein the solvent is selected from the group consisting of: propyleneglycol monomethylether acetate (PGMEA), gamma-butyrolactone (GBL) and N-methylpyrrolidone (NMP).

14. The composition according to claim 1 , which further comprises one or more additives selected from the group consisting of:
dissolution promoters;
adhesion promoters;
antioxidants;
surfactants; and
mixtures in any combination thereof.

15. An article comprising an array of microlens with color filter functionality, wherein said array comprises a composition according to claim 1 .

16. The article according to claim 15 , wherein the array is in a checkerboard configuration.

17. A method of forming a film for the fabrication of color filter-microlens array in a microelectronic or optoelectronic device comprising:
coating a suitable substrate with a composition according to claim 1 to form a film;
patterning the film with a mask by exposing to a suitable radiation;
developing the film after exposure to form a photo-pattern; and
heating the patterned film to a suitable temperature to form an array of microlens.

18. A microlens arrays formed by the composition of claim 1 .

19. An optoelectronic or microelectronic device comprising the microlens arrays of claim 18 .

Assignees

• Promerus Llc

Inventors

• Kandanarachch Pramod F
• Zhen Hongshi
• Rhodes Larry F

Classifications

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/322

  Aqueous alkaline compositions · CPC title

• G03F7/3085

  from plates or webs transported vertically; from plates suspended or immersed vertically in the processing unit · CPC title

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/168

  Finishing the coated layer, e.g. drying, baking, soaking · CPC title