Photoimageable compositions containing photobase generators

Patent metadata

Field	Value
Publication number	US-2016238931-A1
Application number	US-201615042220-A
Country	US
Kind code	A1
Filing date	Feb 12, 2016
Priority date	Feb 18, 2015
Publication date	Aug 18, 2016
Grant date	—

Abstract

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

First claim

What is claimed is:

1 . A photoimageable solvent developable negative tone composition comprising:
a) a polymer having one or more repeating units of formula (IA) derived from a monomer of formula (I):

wherein represents a position at which the bonding takes place with another repeat unit;
R 1 is (C 6 -C 18 )alkyl; perfluoro(C 1 -C 18 )alkyl; (C 6 -C 10 )aryl(C 1 -C 6 )alkyl;
—(CH 2 ) a —CO 2 R 2 where a is an integer from 0 to 4, and R 2 is selected from hydrogen and (C 1 -C 4 )alkyl;
a group of formula (A):
—(CH 2 ) b —(OCH 2 —CH 2 ) c —OR  (A); and

a group of formula (B):

wherein:
b is an integer from 0 to 10;
c is an integer 0, 1, 2, 3 or 4; and
R is hydrogen, linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl;
b) a photobase generator; and
c) a carrier solvent.

2 . The composition of claim 1 , wherein the polymer comprises one or more repeat units derived from the corresponding monomers selected from the group consisting of:
5-hexylbicyclo[2.2.1]hept-2-ene (HexNB); 5-octylbicyclo[2.2.1]hept-2-ene (OctNB); 5-decylbicyclo[2.2.1]hept-2-ene (DecNB); 5-perfluoroethylbicyclo[2.2.1]hept-2-ene (C 2 F 5 NB); 5-n-perfluorobutylbicyclo[2.2.1]hept-2-ene (C 4 F 9 NB); 5-perfluorohexylbicyclo[2.2.1]hept-2-ene (C 6 F 13 NB); 5-benzylbicyclo[2.2.1]hept-2-ene (BenNB); 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB); 2-(7-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)oxirane (EHNB); and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB).

3 . The composition of claim 1 , wherein the polymer comprises one or more repeat units derived from the corresponding monomers selected from the group consisting of:
5-decylbicyclo[2.2.1]hept-2-ene (DecNB); 5-benzylbicyclo[2.2.1]hept-2-ene (BenNB); 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB); 2-(7-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)oxirane (EHNB); and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB).

4 . The composition of claim 2 , wherein the polymer comprises one or more repeat units derived from the corresponding monomers selected from the group consisting of:
5-benzylbicyclo[2.2.1]hept-2-ene (BenNB); 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB); 2-(7-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)oxirane (EHNB); and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB).

5 . 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 (PENB) and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB); a copolymer containing repeating units derived from 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB) and 2-(7-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)oxirane (EHNB); a copolymer containing repeating units derived from 5-benzylbicyclo[2.2.1]hept-2-ene (BenNB) and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB); a copolymer containing repeating units derived from 5-benzylbicyclo[2.2.1]hept-2-ene (BenNB) and 2-(7-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)oxirane (EHNB); a terpolymer containing repeating units derived from 5-decylbicyclo[2.2.1]hept-2-ene (DecNB), 5-benzylbicyclo[2.2.1]hept-2-ene (BenNB) and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB); 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-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB); 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-(7-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)oxirane (EHNB).

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 (PENB) and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB); a copolymer containing repeating units derived from 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB) and 2-(7-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)oxirane (EHNB); a copolymer containing repeating units derived from 5-benzylbicyclo[2.2.1]hept-2-ene (BenNB) and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB); and a copolymer containing repeating units derived from 5-benzylbicyclo[2.2.1]hept-2-ene (BenNB) and 2-(7-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)oxirane (EHNB).

7 . 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 (PENB) and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB); and a copolymer containing repeating units derived from 5-benzylbicyclo[2.2.1]hept-2-ene (BenNB) and 2-(8-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB).

8 . The composition of claim 1 , wherein the photobase generator is represented by formula (II):

where R 3 is (C 1 -C 6 )alkyl or (C 6 -C 10 )aryl(C 1 -C 6 )alkyl.

9 . The composition of claim 1 , wherein the photobase generator is selected from the group consisting of:
1-benzyloctahydropyrrolo[1,2-a]pyrimidine; 1-(1-phenylethyl)octahydropyrrolo[1,2-a]pyrimidine; 1-(1-phenylpropyl)octahydropyrrolo[1,2-a]pyrimidine; 1-(1-(o-tolypethyl)octahydropyrrolo[1,2-a]pyrimidine; and 1-(1-(p-tolyl)ethyl)octahydropyrrolo[1,2-a]pyrimidine.

10 . The composition of claim 1 , wherein the photobase generator is selected from the group consisting of:
1-benzyloctahydropyrrolo[1,2-a]pyrimidine; and 1-(1-phenylethy)octahydropyrrolo[1,2-a]pyrimidine.

11 . The composition of claim 1 , wherein the photobase generator is 1-(1-phenylethyl)octahydropyrrolo[1,2-a]pyrimidine.

12 . The composition of claim 1 further comprises one or more additives selected from the group consisting of:
a photosensitizer;
an antioxidant; and
an adhesion promoter.

13 . The composition of claim 12 , wherein the photosensitizer is:

14 . The composition of claim 12 , wherein the adhesion promoter is selected from the group consisting of

15 . The composition of claim 12 , wherein the adhesion promoter is:

Assignees

• Promerus Llc

Inventors

• Ng Hendra
• Zhang Wei

Classifications

• G03F7/038 Primary

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/0751

  used as adhesion-promoting additives or as means to improve adhesion · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/0382

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title