Photoimageable compositions containing oxetane functionality

• US 9,575,409 B2
• Filed: 11/20/2015
• Issued: 02/21/2017
• Est. Priority Date: 11/26/2014
• Status: Active Grant

• Current Assignee: Promerus, LLC (Sumitomo Bakelite Company Limited)
• Original Assignee: Promerus, LLC (Sumitomo Bakelite Company Limited)
• Inventors: Ng, Hendra, Zhang, Wei
• Primary Examiner(s): Hamilton, Cynthia
• Application Number:
  US14/946,843
• Publication Number:
  US 20160147145A1
• Time in Patent Office: 459 Days
• Field of Search: 430/270.1, 430/280.1
• US Class Current: 1/1
• CPC Class Codes: G03F 7/0045 with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
• CPC Class Codes: G03F 7/0046 with perfluoro compounds, e.g. for dry lithography G03F7/0048 takes precedence
• CPC Class Codes: G03F 7/038 Macromolecular compounds which are rendered insoluble or differentially wettable G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021
• CPC Class Codes: G03F 7/0382 the macromolecular compound being present in a chemically amplified negative photoresist composition
• CPC Class Codes: G03F 7/0388 with ethylenic or acetylenic bands in the side chains of the photopolymer
• CPC Class Codes: G03F 7/0751 used as adhesion-promoting additives or as means to improve adhesion
• CPC Class Codes: G03F 7/0755 Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds G03F7/0752 takes precedence
• CPC Class Codes: G03F 7/325 Non-aqueous compositions

Abstract

Embodiments in accordance with the present invention encompass negative-tone, solvent developable, self-imageable polymer compositions useful for forming films that can be patterned to create structures for microelectronic devices, microelectronic packaging, microelectromechanical systems, optoelectronic devices and displays.

Claims

1. A photoimageable solvent developable negative tone composition comprising:

a) a polymer selected from the group consisting of;

a copolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB) and 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB); and

a terpolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB) and 2-((bicycle[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB);

b) an oxetane compound;

2. The composition of claim 1, wherein the polymer is a copolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB) and 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB).

3. The composition of claim 1, wherein the polymer is a terpolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 5-phenethylbicyclo [2.2.1]hept-2-ene (PENB) and 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB).

4. The composition of claim 1, which further comprises one or more adhesion promoters selected from the group consisting of:

5. A photoimageable solvent developable negative tone composition comprising:

a) a polymer selected from the group consisting of;

a copolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB) and 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB); and

a terpolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB) and 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB);

b) an oxetane compound selected from the group consisting of;

a compound of formula (IIIA);

6. The composition of claim 5, wherein the polymer is a copolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB) and 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB).

7. The composition of claim 5, wherein the polymer is a terpolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB) and 2-((bicyclo [2 .2 .1] hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB).

8. The composition of claim 5, wherein the oxetane compound is a compound of formula (IIIA):

9. The composition of claim 5, wherein the oxetane compound is

10. The composition of claim 5, wherein the oxetane compound is

11. The composition of claim 5, wherein the oxetane compound is

12. The composition of claim 5, wherein the oxetane compound is

13. The composition of claim 5, wherein the oxetane compound is

14. The composition of claim 5, wherein the photoactive compound is

15. The composition of claim 5, wherein the photoactive compound is

16. The composition of claim 5, wherein the adhesion promoter is

17. The composition of claim 5, wherein the adhesion promoter is