Non-subliming, difunctionalized ultraviolet dyes for use in anti-reflective coatings
AssigneeBrewer Science Inc.
InventorShreeram V. Deshpande
Life of this patent
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Abstract
An improved light attenuating compound for use in the production of microdevices is provided. Broadly, the light attenuating compound is difunctional and can be directly incorporated (either physically or chemically) into photolithographic compositions such as anti-reflective coatings (ARC) and contact or via hole fill materials. The preferred light attenuating compound comprises functional groups electronically isolated from the light absorbing moieties of the compound. As a result, the spectral properties of the compound are not negatively affected when the functional groups form bonds with other compounds during polymerization or crosslinking.
Claims21
In a curable composition for use during microlithographic processes, said composition comprising a polymer binder dissolved in a solvent system, the improvement which comprises:
- a light attenuating compound selected from the group consisting of
- wherein:
- each cyclic group is an aromatic group;
- each R1 is individually selected from the group consisting of —OH, —COOH, —NH2, —COOR′, —CH═CH2, and epoxy groups, where R′ is an alkyl group;
- and
- each R2 is individually selected from the group consisting of hydrogen, alkyls, heteroalkyls, aryls, heteroaryls, ethers, thioethers, carboxylates, cyanos, halogens, R″—C═N—, R″—N═N′,
- where R″ is hydrogen or an alkyl group, dialkylaminos, diarylaminos, and one of the following:
- or
- x=0 or 1,
- wherein, * indicates the point of attachment of R2 to the cyclic group, and in Structure A:
- EWG is selected from the group consisting of carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls;
- and
- R3 is selected from the group consisting of hydrogen, alkyls, heteroalkyls, aryls, heteroaryls, carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls;
- and
- wherein, in structure B, EWG and R3 are selected from the group consisting of carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls.
A light attenuating compound having the formula:
- wherein:
- each cyclic group is an aromatic group,
- each R1 is individually selected from the group consisting of —OH, —COOH, —NH2, —COOR′, —CH═CH2, and epoxy groups, where R′ is an alkyl group;
- each R2 is individually selected from the group consisting of hydrogen, alkyls, heteroalkyls, aryls, heteroaryls, ethers, thioethers, carboxylates, cyanos, halogens, R″—C═N—, R″—N═N′, where R″ is hydrogen or an alkyl group, dialkylaminos, diarylaminos, and one of the following:
- or
- x=0 or 1,
- wherein, * indicates the point of attachment of R2 to the cyclic group, and in Structure A:
- EWG is selected from the group consisting of carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls;
- and
- R3 is selected from the group consisting of hydrogen, alkyls, heteroalkyls, aryls, heteroaryls, carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls, and
- wherein, in structure B, EWG and R3 are selected from the group consisting of carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls.
The combination of a substrate having a surface and an anti-reflective layer on said substrate surface, said anti-reflective layer including therein a light attenuating compound selected from the group consisting of:
- wherein:
- each cyclic group is an aromatic group;
- each R1 is individually selected from the group consisting of —OH, —COOH, —NH2, —COOR′, —CH═CH2, and epoxy groups, where R′ is an alkyl group;
- and
- each R2 is individually selected from the group consisting of hydrogen, alkyls, heteroalkyls, aryls, heteroaryls, ethers, thioethers, carboxylates, cyanos, halogens, R″—C═N—, R″—N═N′,
- where R″ is hydrogen or an alkyl group, dialkylaminos, diarylaminos, and one of the following:
- or
- x=0 or 1,
- wherein, * indicates the point of attachment of R2 to the cyclic group, and in Structure A:
- EWG is selected from the group consisting of carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls;
- and
- R3 is selected from the group consisting of hydrogen, alkyls, heteroalkyls, aryls, heteroaryls, carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls;
- and
- wherein, in structure B, EWG and R3 are selected from the group consisting of carbonyls, cyanos, iminos, carboxylic acids, carboxylic esters, carboxamidos, carboximidos, and sulfonyls.
A light attenuating compound having a formula selected from the group consisting of:
- n=1−30(III), and
- (IV),
- wherein R1 is selected from the group consisting of —OH, —COOH, —NH2, —COOR′, —CH═CH2, and epoxy groups, where R′ is an alkyl group.
Dependencies are inferred from the claim text.