Photoimageable compositions containing oxetane functionality

Patent metadata

Field	Value
Publication number	US-2016147145-A1
Application number	US-201514946843-A
Country	US
Kind code	A1
Filing date	Nov 20, 2015
Priority date	Nov 26, 2014
Publication date	May 26, 2016
Grant date	—

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.

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 or —(CH2) a —CO 2 R 2 where a is an integer from 0 to 4, and R 2 is hydrogen or (C 1 -C 4 )alkyl;
b) a compound of the formula (III):

wherein e is an integer from 1 to 4;
L is a bond or a divalent linking or a spacer group selected from ether, ketone, amine, sulfide, sulfone, ester or an amide group;
R 7 is a core organic moiety selected from an aliphatic or an aromatic group;
R 8 is (C 1 -C 4 )alkyl;
c) a photoactive compound; and
d) a carrier solvent.

2 . The composition of claim 1 , wherein the polymer further comprises one or more additional repeat units represented by formula (IIA), said repeat unit is derived from a monomer of formula (II):

wherein:
denotes a place of bonding with another repeat unit;
b is 0 or 1;
R 3 , R 4 , R 5 and R 6 are the same or different and each independently of one another is selected from hydrogen, linear or branched (C 1 -C 16 )alkyl, (C 1 -C 16 )alkenyl, hydroxy(C 1 -C 16 )alkyl, hydroxyperfluoro(C 1 -C 4 )alkyl(C 1 -C 4 )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 3 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, di(C 1 -C 2 )alkylmaleimide(C 3 -C 6 )alkyl, di(C 1 -C 2 )alkylmaleimide(C 2 -C 6 )alkoxy(C 1 -C 2 )alkyl, hydroxy, (C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 1 -C 12 )alkoxy(C 1 -C 8 )alkyl, (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, (C 1 -C 6 )acyloxy, oxiranyl(C 0 -C 8 )alkyl, oxiranyl(CH 2 ) c O(CH 2 ) d —, halogen or a group of formula (A):
(CH 2 ) c —(OCH 2 —CH 2 ) d —OR   (A);

or a group of formula (B):

wherein:
c is an integer 0, 1, 2, 3 or 4;
d is an integer 0, 1, 2, 3 or 4; and
R is linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl; where each of the aforementioned substituents are optionally substituted with a group selected from halogen or hydroxy.

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-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); ethyl 3-(bicyclo[2.2.1]hept-2-en-2-yl)propanoate (EPEsNB), bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (Acid NB) and norbornenylpropanoic acid (NBEtCOOH).

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-(but-3-en-1-yl)bicyclo[2.2.1]hept-2-ene (1-ButenylNB); 5-(but-2-en-1-yl)bicyclo[2.2.1 ]hept-2-ene (2-ButenylNB); 5-(but-1-en-1-yl)bicyclo[2.2.1 ]hept-2-ene (3-ButenylNB); norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol (HFANB); 1-(3-(bicyclo[2.2.1]hept-5-en-2-yl)propyl)-3,4-dimethyl-1H-pyrrole-2,5-dione (PrDMMINB); 1-(4-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)-3,4-dimethyl-1H-pyrrole-2,5-dione (BuDMMINB); 1-(6-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)-3,4-dimethyl-1H-pyrrole-2,5-dione (HexDMMINB); tetraoxadodecanenorbornene (NBTODD); 5-(3-methoxybutoxy)methyl-2-norbornene (NB-3-MBM); 5-(3-methoxypropanoxy)methyl-2-norbornene (NB-3-MPM); 5-((2-(2-methoxyethoxy)ethoxy)methyl)bicyclo[2.2.1]hept-2-ene (NBTON); 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB); 2-(bicyclo[2.2.1]hept-5-en-2-yl)oxirane; and 2-(7-(bicyclo[2.2.1]hept-5-en-2-yl)heptyl)oxirane.

5 . The composition of claim 1 , wherein the polymer is 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).

6 . The composition of claim 1 , wherein the compound of the formula (III) is selected from one or more compounds from the group consisting of:
a compound of formula (IIIA):

wherein f is an integer from 1 to 3;
a compound of formula (IIIB):

wherein g is an integer from 1 to 3;
a compound of formula (IIIC):

wherein R 9 is a bond, (C 1 -C 14 )alkyl or (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl;

7 . The composition of claim 1 , wherein the photoactive compound is a photoacid generator.

8 . The composition of claim 7 , wherein the photoacid generator is selected from the group consisting of:

9 . 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.

10 . The composition of claim 9 , wherein the photosensitizer is:

11 . The composition of claim 9 , wherein the antioxidant is selected from the group consisting of:

12 . The composition of claim 9 , wherein the adhesion promoter is selected from the group consisting of:

13 . A photoimageable solvent developable negative tone composition comprising:
a) a polymer having a repeat unit of formula (IVA) derived from a monomer of formula (IV):

wherein represents a position at which the bonding takes place with another repeat unit;
L 1 and L 2 are the same or different and each independently of one another is s

Assignees

• Promerus Llc

Inventors

• Ng Hendra
• Zhang Wei

Classifications

• G03F7/0045

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

• G03F7/0046

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

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/0755

  Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence) · CPC title

• G03F7/0382

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