US 9,261,781 B2Granted

Preparation of norbornane-based PAC ballasts

AssigneeSumitomo Bakelite Co., Ltd.

InventorsAndrew Bell, Keitaro Seto, Hiroaki Makabe

Life of this patent

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Abstract

Embodiments in accordance with the present invention provide for norbornane-type ballast materials, norbornane-type photoactive compounds derived from such ballast materials and alkali-soluble positive-tone polymer compositions that encompass such norbornane-type photoactive compounds and one of a PBO or PNB resin.

Claims19

Dependent claims

A compound of formula AA or BB:

wherein
n independently of each other is an integer from 0 to 3;
Z is selected independently from one or more of structures C or D:
where C*** represents a carbon atom of a norbornane ring and Q represents from one to five substituents independently selected from —OH, a halogen, a C1 to C6 alkyl group, a C3 to C12 cycloalkyl group, an aryl and an alkaryl group, n is from 0 to 4, and with the provisos that at least one of such substituents is —OH;
W in formula AA is either a covalent bond or a divalent linking group selected from a C1 to C12 alkyl, ether or polyether, a C3 to C12 cycloalkyl, aryl or alkaryl group, or one or more norbornane-type moieties;
W* in formula BB is hydrogen, a monovalent group selected from a C1 to C12 alkyl, ether or polyether, a C3 to C12 cycloalkyl, aryl or alkaryl group, or one or more norbornane-type moieties.

3 more elements

A Compound selected from the group consisting of:

4-(5-hexylbicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
4-(5-hexylbicyclo[2.2.1]heptan-2-yl)-2-isopropylphenol;
2-cyclohexyl-4-(5-hexylbicyclo[2.2.1]heptan-2-yl)-5-methylphenol;
4-(5-decylbicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
4-(5-decylbicyclo[2.2.1]heptan-2-yl)-2-isopropylphenol;
2-cyclohexyl-4-(5-decylbicyclo[2.2.1]heptan-2-yl)-5-methylphenol;
4-(5-2,5,8,11-tetraoxadodecylbicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
4-(5-2,5,8,11-tetraoxadodecylbicyclo[2.2.1]heptan-2-yl)-2-isopropylphenol;
4-(5-2,5,8,11-tetraoxadodecylbicyclo[2.2.1]heptan-2-yl)-2-cyclohexyl-5-methyl-phenol;
2-methyl-4-(5-phenylbicyclo[2.2.1]heptan-2-yl)phenol;
2-isopropyl-4-(5-phenylbicyclo[2.2.1]heptan-2-yl)phenol;
2-cyclohexyl-4-(5-phenylbicyclo[2.2.1]heptan-2-yl)phenol;
ethyl 3-(5-(4-hydroxy-3-methylphenyl)bicyclo[2.2.1]heptan-2-yl)propanoate;
ethyl 3-(5-(4-hydroxy-3-isopropylphenyl)bicyclo[2.2.1]heptan-2-yl)propanoate;
ethyl 3-(5-(3-cyclohexyl-4-hydroxyphenyl)bicyclo[2.2.1]heptan-2-yl)propanoate;
4-(bicyclo[2.2.1]heptan-2-yl)-2-isopropylphenol;
4-(5-((2-methoxyethoxy)methyl)bicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
2-isopropyl-4-(5-((2-methoxyethoxy)methyl)bicyclo[2.2.1]heptan-2-yl)phenol;
2-cyclohexyl-4-(5-((2-methoxyethoxy)methyl)bicyclo[2.2.1]heptan-2-yl)-5-methyl-phenol;
4-(5-((2-(2-methoxyethoxy)ethoxy)methyl)bicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
2-isopropyl-4-(5-((2-(2-methoxyethoxy)ethoxy)methyl)-bicyclo[2.2.1]heptan-2-yl)-phenol;
2-cyclohexyl-4-(5-((2-(2-methoxyethoxy)ethoxy)methyl)-bicyclo[2.2.1]heptan-2-yl)-5-methylphenol;
2-methyl-4-(5-(3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl)-bicyclo[2.2.1]-heptan-2-yl)phenol;
2-isopropyl-4-(5-(3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl)-bicyclo[2.2.1]-heptan-2-yl)phenol;
2-cyclohexyl-4-(5-(3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl)-bicyclo[2.2.1]-heptan-2-yl)phenol;
4-(5-benzylbicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
4-(5-benzylbicyclo[2.2.1]heptan-2-yl)-2-isopropylphenol;
4-(5-(2-methylbicyclo[2.2.1]heptane)bicyclo[2.2.1]heptan-2-yl)-2-cyclohexylphenol;
4-(bicyclo[2.2.1]heptan-2-yl)-2-cyclohexylphenol;
4-(5-benzylbicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
4-(5-(2-methylbicyclo[2.2.1]heptane)bicyclo[2.2.1]heptan-2-yl)-2-isopropylphenol;
4-(5-(2-methylbicyclo[2.2.1]heptane)bicyclo[2.2.1]heptan-2-yl)-2-cyclohexylphenol;
4-(decahydro-1,4:5,8-dimethanonaphthalen-2-yl)-2-methylphenol;
4-(decahydro-1,4:5,8-dimethanonaphthalen-2-yl)-2-isopropylphenol;
4-(decahydro-1,4:5,8-dimethanonaphthalen-2-yl))-2-cyclohexylphenol;
4-(5-(4-hydroxybenzyl)bicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
4-(5-(4-hydroxybenzyl)bicyclo[2.2.1]heptan-2-yl)-2,5-dimethylphenol;
2-cyclohexyl-4-(5-(methoxymethyl)bicyclo[2.2.1]heptan-2-yl)-5-methylphenol;
4-(5-(methoxymethyl)bicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
2-methyl-4-(5-((oxiran-2-ylmethoxy)methyl)bicyclo[2.2.1]heptan-2-yl)phenol;
2-cyclohexyl-5-methyl-4-(5-((oxiran-2-ylmethoxy)methyl)bicyclo[2.2.1]-heptan-2-yl)phenol;
2-methyl-4-(5-(6-(oxiran-2-yl)hexyl)bicyclo[2.2.1]heptan-2-yl)phenol;
2-cyclohexyl-5-methyl-4-(5-(6-(oxiran-2-yl)hexyl)bicyclo[2.2.1]heptan-2-yl)phenol;
2-cyclohexyl-4-(5-(methoxymethyl)bicyclo[2.2.1]heptan-2-yl)-5-methylphenol;
4-(5-(hydroxymethyl)bicyclo[2.2.1]heptan-2-yl)-2-methylphenol;
5-(5-cyclohexyl-4-hydroxy-2-methylphenyl)bicyclo[2.2.1]heptan-2-yl)methyl acetate;
(5-(4-hydroxy-3-methylphenyl)bicyclo[2.2.1]heptan-2-yl)methyl acetate;
4,4′-((5-(4-hydroxy-3-methylphenyl)bicyclo[2.2.1]heptan-2-yl)methylene)bis(2-methylphenol);
4,4′-((5-(4-hydroxy-3-isopropylphenyl)bicyclo[2.2.1]heptan-2-yl)methylene)bis(2-isopropylphenol);
4,4′-((5-(3-cyclohexyl-4-hydroxyphenyl)bicyclo[2.2.1]heptan-2-yl)methylene)bis-(2-methylphenol);
4,4′-((5-(4-hydroxyphenyl)bicyclo[2.2.1]heptan-2-yl)methylene)bis(2-methylphenol);
4,4′,4″-(bicyclo[2.2.1]heptane-2,2,5-triyl)tris(2-methylphenol);
4,4′,4″-(bicyclo[2.2.1]heptane-2,2,5-triyl)tris(2-isopropylphenol);
4,4′-(5-(3-cyclohexyl-4-hydroxyphenyl)bicyclo[2.2.1]heptane-2,2-diyl)bis-(2-methylphenol);
4,4′-(5-(4-hydroxyphenyl) bicyclo[2.2.1]heptane-2,2-diyl)bis(2-methylphenol);
5′-(5-(4-hydroxybenzyl)bicyclo[2.2.1]heptan-2-yl)-3,3″-dimethyl-[1,1′:3′,1″terphenyl]-4,4″-diol;
5′-(5-(4-hydroxyphenyl)bicyclo[2.2.1]heptan-2-yl)-3,3″-dimethyl-[1,1′:3′,1″terphenyl]-4,4″-diol;
4,4′,4″,4′″-(5,5′)-1,4-phenylene)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis-(methanetriyl)tetrakis(2-methylphenol);
4,4′,4″,4′″-(5,5′-(1,4-phenylene)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis-(methanetriyl)tetrakis(2-cyclohexyl-5-methylphenol);
4,4′,4″,4′″-(5,5′-(1,4-phenylene)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis-(methanetriyl)tetrakis(2-isopropylphenol);
4,4′,4″,4′″-(5,5′-(1,4-phenylene)bis(bicyclo[2.2.1]heptane-5,2-diyl)bis-(methanetriyl)tetrakis(2,5-dimethylphenol);
4,4′,4″,4′″-(5,5′-(1,4-phenylene)bis(bicyclo[2.2.1]heptane-5, 2, 2-triyl))-tetrakis(2-methylphenol);
4,4′-(5-(4-(5-(5-cyclohexyl-4-hydroxy-2-methylphenyl)-5-(3-cyclohexyl-4-hydroxyphenyl)bicyclo[2.2.1]heptan-2-yl)phenyl)bicyclo[2.2.1]heptane-2,2-diyl)bis(2-cyclohexyl-5-methylphenol);
4,4′,4″,4′″-(5,5′-(1,4-phenylene)bis(bicyclo[2.2.1]heptane-5,2,2-triyl)tetrakis-(2,5-dimethylphenol);
and
5′-(5-(bis(4-hydroxy-2,5-dimethylphenyl)methyl)bicyclo[2.2.1]heptan-2-yl)-3,3″-dimethyl-[1,1′:3′,1″-terphenyl]-4,4″-diol.

63 more elements

A Compound selected from the group consisting of:

4,4′-(((5S)-5-phenylbicyclo[2.2.1]heptan-2-yl)methylene)bis(2-methylphenol);
4,4′-((5S)-5-phenylbicyclo[2.2.1]heptane-2,2-diyl)bis(2-methylphenol);
4,4′-((5-phenylbicyclo[2.2.1]heptan-2-yl)methylene)bis(2-isopropyl-5-methylphenol);
4-(2-(4-hydroxy-3-isopropyl-5-methylphenyl)-5-phenylbicyclo[2.2.1]heptan-2-yl)-2-isopropyl-5-methylphenol;
4,4′-((5-phenylbicyclo[2.2.1]heptan-2-yl)methylene)bis(2-cyclohexyl-5-methylphenol);
2-cyclohexyl-4-(2-(3-cyclohexyl-4-hydroxy-5-methylphenyl)-5-phenylbicyclo[2.2.1]-heptan-2-yl)-5-methylphenol;
4,4′-(bicyclo[2.2.1]heptane-2,5-diyl)bis(2-methylphenol);
4,4′-(bicyclo[2.2.1]heptane-2,5-diyl)bis(2-isopropylphenol);
4,4′-(bicyclo[2.2.1]heptane-2,5-diyl)bis(2-cyclohexyl-5-methylphenol);
4,4′-(tetracyclo[6.2.1.13,6.0.2,7]dodecan-2,7-diyl)bis(2-cyclohexyl-5-methylphenol);
4,4′-(5,5′-(2,2′-oxybis(ethane-2,1-diyl))bis(bicyclo[2.2.1]heptane-5,2-diyl))-bis(2-cyclohexylphenol);
4,4′-(5,5′-(2,2′-oxybis(ethane-2,1-diyl))bis(bicyclo[2.2.1]heptane-5,2-diyl))-bis(2-isopropylphenol);
4,4′-(5,5′-(2,2′-oxybis(ethane-2,1-diyl))bis(bicyclo[2.2.1]heptane-5,2-diyl))-bis(2-methylphenol);
4,4′-(5,5′-(butane-1,4-diyl)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis(2-methylphenol);
4,4′-(5,5′-(butane-1,4-diyl)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis(2-isopropylphenol);
2-cyclohexyl-4-(5-(4-(5-(3-cyclohexyl-4-methylphenyl)bicyclo[2.2.1]heptan-2-yl)butyl)bicyclo[2.2.1]heptan-2-yl)phenol;
4,4′-(tetracyclo[6.2.1.13,6.0.2,7]dodecan-2-ylmethylene)bis(2-methylphenol);
4,4′-(tetracyclo[6.2.1.13,6.0.2,7]dodecan-2-ylmethylene)bis(2-isopropylphenol);
4,4′-(tetracyclo[6.2.1.13,6.0.2,7]dodecan-2-ylmethylene)bis(2-cyclohexyl-5-methylphenol);
4,4′-(5,5′-(1,4-phenylene)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis(2-methylphenol);
4,4′-(5,5′-(1,4-phenylene)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis(2-isopropylphenol);
4,4′-(5,5′-(1,4-phenylene)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis(2-cyclohexylphenol);
4,4′-(5,5′-(biphenyl-4,4′-diyl)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis(2-methylphenol);
4,4′-(5,5′-(biphenyl-4,4′-diyl)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis(2-isopropylphenol);
4,4′-(5,5′-(biphenyl-4,4′-diyl)bis(bicyclo[2.2.1]heptane-5,2-diyl))bis-(2-cyclohexylphenol);
4,4′-(pentacyclo[8.2.1.14,7.02,9.08,3]tetradecan-2,8-yl)bis(2-methylphenol);
4,4′-(pentacyclo[8.2.1.14,7.02,9.08,3]tetradecan-2,8-yl)bis(2-isopropylphenol);
4,4′-(pentacyclo[8.2.1.14,7.02,9.08,3]tetradecan-2,8-yl)bis(2-cyclohexyl-5-methylphenol);
4,4′-(dodecahydro-1,4:5,8-dimethanobiphenylene-2,6-diyl)bis(2-methylphenol);
4,4′-(dodecahydro-1,4:5,8-dimethanobiphenylene-2,6-diyl)bis(2-isopropylphenol);
and
4,4′-(dodecahydro-1,4:5,8-dimethanobiphenylene-2,6-diyl)bis(2-cyclohexyl-5-methylphenol).

29 more elements

A norbornane-type photoactive compound of formula AA or BB:

wherein
n independently of each other is an integer from 0 to 3;
Z represents one to four substituted or unsubstituted ArOD substituents, where Ar is an aryl group and where at least one of D is one of benzoquinone (BQ) or diazonaphthoquinone DNQ moieties represented by Formulae F, G or H respectively:
and the remaining D is hydrogen;
W in formula AA is either a covalent bond or a divalent linking group selected from a C1 to C12 alkyl, ether or polyether, a C3 to C12 cycloalkyl, aryl or alkaryl group, or one or more norbornane-type moieties;
W* in formula BB is hydrogen, a monovalent group selected from a C1 to C12 alkyl, ether or polyether, a C3 to C12 cycloalkyl, aryl or alkaryl group, or one or more norbornane-type moieties.

3 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/963,304Filed 9 Aug 2013 · continuation
Priority: 28 Sep 2010
Published: US 2013/0323640 A15 Dec 2013
Granted: 16 Feb 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

G03F 7/022
Photosensitive materials: quinonediazides
C07C 39/17
Polycyclic with no unsaturation outside the aromatic rings: containing other rings in addition to the six-membered aromatic rings , e.g.…
C07C 43/1782
Containing hydroxy or O-metal groups: containing six-membered aromatic rings
C07C 43/1783
Containing six-membered aromatic rings: with hydroxy or -O-metal groups bound to the aromatic rings

Family

Application61/387,096Us provisional application · filed 28 Sep 2010
Application13/248,015Parent of this continuation · filed 28 Sep 2011
US 8,530,133 B2Parent of this continuation · filed 10 Sep 2013
US 2013/0323640 A1Pre-grant publication · published 5 Dec 2013
US 2012/0135352 A1Published application
US 9,261,781 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Facts

Application

13/963,304Filed 9 Aug 2013 · continuation

Priority

28 Sep 2010

Published

US 2013/0323640 A15 Dec 2013

Granted

16 Feb 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification16 codes

G03F 7/022
Photosensitive materials: quinonediazides
C07C 39/17
Polycyclic with no unsaturation outside the aromatic rings: containing other rings in addition to the six-membered aromatic rings , e.g.…
C07C 43/1782
Containing hydroxy or O-metal groups: containing six-membered aromatic rings
C07C 43/1783
Containing six-membered aromatic rings: with hydroxy or -O-metal groups bound to the aromatic rings

Family

Application61/387,096Us provisional application · filed 28 Sep 2010

Application13/248,015Parent of this continuation · filed 28 Sep 2011

US 8,530,133 B2Parent of this continuation · filed 10 Sep 2013

US 2013/0323640 A1Pre-grant publication · published 5 Dec 2013

US 2012/0135352 A1Published application

US 9,261,781 B2This patent

From the US filing history. Foreign family members aren’t listed.