US5023164A — Highly sensitive dry developable deep UV photores…

Claim 1

Independent Claim 85 words

A dry developable photoresist composition which comprises a phenol-aldehyde type condensation product, wherein at least 90% of the hydroxyl groups of which are substituted with acid labile groups which inhibit the reaction of the protected reaction product with organometallic reagents and a photoactive compound which generates a strong acid upon exposure to deep UV radiation or vacuum UV radiation to remove the acid labile groups from the condensation product in its exposed regions to enable reaction of the de-protected hydroxy groups with the organometallic reagents.

Claim 2

Dependent Claim 85 words

A dry developable photoresist composition which comprises a phenol-aldehyde type condensation product, wherein at least 90% of the hydroxyl groups of which are substituted with acid labile groups which inhibit the reaction of the protected reaction product with organometallic reagents and a photoactive compound which generates a strong acid upon exposure to deep UV radiation or vacuum UV radiation to remove the acid labile groups from the condensation product in its exposed regions to enable reaction of the de-protected hydroxy groups with the organometallic reagents.

Claim 3

Dependent Claim 84 words

The photoresist composition of claim 1 wherein the phenol aldehyde type condensation product may be represented by the general formula ##STR4## where R is selected from the group consisting of H, --CH 3 and phenyl R' is selected from the group consisting of H, alkyl and aryl, and R" is selected from the group consisting of H, halo, nitro, alkoxy, alkyl, aryl, and hydroxyl, and where the aromatic ring may have fused thereto an additional ring structure to form a napthhol or anthracene unit.

Claim 4

Dependent Claim 25 words

The photoresist composition of claim 2 wherein the phenol aldehyde type condensation product is selected from the group consisting of meta-cresol novolak and naphthol novolak.

Claim 5

Dependent Claim 49 words

The photoresist composition of claim 1 wherein the acid labile protecting group forms a secondary or tertiary carbonium ion upon reaction with acid having an available alpha proton and is degradable to form an olefin and an hydronium ion to continue the acid hydrolysis in the region of exposure.

Claim 6

Dependent Claim 36 words

The photoresist composition of claim 1 wherein the photoactive compound is selected from the group consisting of metallic and nonmetallic onium salts, tosylates and non-metallic sulfonic acid precursors which generate strong acids upon exposure to radiation.

Claim 7

Dependent Claim 25 words

The photoresist composition of claim 5 wherein the metallic onium salt is selected from the group consisting of diaryliodonium salts, arylsulfonium salts, and arylselenonium salts.

Claim 8

Dependent Claim 21 words

The photoresist composition of claim 1 wherein at least 95% of the hydroxyl groups are substituted with said acid labile groups.

Claim 9

Dependent Claim 21 words

The photoresist composition of claim 1 wherein at least 98% of the hydroxyl groups are substituted with said acid liabile groups.

Claim 10

Dependent Claim 32 words

The photoresist composition of claim 1 which is dissolved in a solvent selected from the group consisting of xylene, alphyl acetate, propylene glycol alkyl ether acetate, and ethyl lactate, and mixtures thereof.

Claim 11

Dependent Claim 15 words

The photoresist composition of claim 9 wherein the solvent is propylene glycol methyl ether acetate.

Claim 12

Dependent Claim 45 words

The photoresist composition of claim 9 wherein the protected phenol-aldehyde condensation product is present in an amount from 15-40% by weight of the composition, and the photoactive compound is present in an amount from 1 to 40% by weight of the protected phenol-aldehyde condensation product.

Claim 13

Dependent Claim 20 words

The photoresist composition of claim 1 wherein the protected phenol-aldehyde condensation product is a t-butylcarbonate of a m-cresol novolak resin.

Claim 14

Dependent Claim 133 words

A dry developable photoresist composition which comprises a phenol-aldehyde type condensation product, wherein at least 90% of the hydroxyl groups of which are substituted with acid labile groups selected from the group consisting of t-butyloxycarbonyl, 2-propyloxycarbonyl, t-butyl ether, and t-butylcarbonyl which inhibit the reaction of the protected reaction product with organometallic reagents which upon reaction with acid forms a secondary or tertiary carbonium ion having an available alpha proton and which is degradable to form an olefin and an hydronium ion to continue acid hydrolysis in exposed regions and a photoactive compound which generates a strong acid upon exposure to deep UV radiation or vacuum UV radiation to remove the acid labile groups from the condensation product in its exposed regions to enable reaction of the de-protected hydroxy groups with the organometalic reagents.

Claim 15

Dependent Claim 133 words

A dry developable photoresist composition which comprises a phenol-aldehyde type condensation product, wherein at least 90% of the hydroxyl groups of which are substituted with acid labile groups selected from the group consisting of t-butyloxycarbonyl, 2-propyloxycarbonyl, t-butyl ether, and t-butylcarbonyl which inhibit the reaction of the protected reaction product with organometallic reagents which upon reaction with acid forms a secondary or tertiary carbonium ion having an available alpha proton and which is degradable to form an olefin and an hydronium ion to continue acid hydrolysis in exposed regions and a photoactive compound which generates a strong acid upon exposure to deep UV radiation or vacuum UV radiation to remove the acid labile groups from the condensation product in its exposed regions to enable reaction of the de-protected hydroxy groups with the organometalic reagents.

Claim 16

Dependent Claim 191 words

A dry developable photoresist composition which comprises a phenol-aldehyde type condensation product, wherein at least 90% of the hydroxyl groups of which are substituted with acid labile groups which inhibit the reaction of the protected reaction product with organometallic reagents and a photoactive compound which comprises a non-metallic sulfonic acid precursor of the form ##STR5## wherein Q is selected from the group consisting of --CF 3 , --CF 2 CF 3 , --CF 2 CF 2 H, --(CF 2 ) n --Z where n=1 to 4 and Z is H, alkyl, aryl, ##STR6## where m=1 to 5, where X and Y (1) form a cylcic or polycyclic ring which may contain one or more hetero-atoms, (2) form a fused aromatic ring, (3) may be independently H, alkyl or aryl, (4) may be attached to another sulfonyloxyimido-containing residue, or (5) may be attached to a polymeric chain or backbone said photoactive compound generates a strong acid upon exposure to deep UV radiation or vacuum UV radiation to remove the acid labile groups from the condensation product in its exposed regions to enable reaction of the de-protected hydroxy groups with the organometallic reagents.

Claim 17

Dependent Claim 191 words

A dry developable photoresist composition which comprises a phenol-aldehyde type condensation product, wherein at least 90% of the hydroxyl groups of which are substituted with acid labile groups which inhibit the reaction of the protected reaction product with organometallic reagents and a photoactive compound which comprises a non-metallic sulfonic acid precursor of the form ##STR5## wherein Q is selected from the group consisting of --CF 3 , --CF 2 CF 3 , --CF 2 CF 2 H, --(CF 2 ) n --Z where n=1 to 4 and Z is H, alkyl, aryl, ##STR6## where m=1 to 5, where X and Y (1) form a cylcic or polycyclic ring which may contain one or more hetero-atoms, (2) form a fused aromatic ring, (3) may be independently H, alkyl or aryl, (4) may be attached to another sulfonyloxyimido-containing residue, or (5) may be attached to a polymeric chain or backbone said photoactive compound generates a strong acid upon exposure to deep UV radiation or vacuum UV radiation to remove the acid labile groups from the condensation product in its exposed regions to enable reaction of the de-protected hydroxy groups with the organometallic reagents.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1994-06-10	1994-12-10	1995-06-11	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1998-06-10	1998-12-10	1999-06-11	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2002-06-10	2002-12-10	2003-06-11	$7700.00	Window Closed / Lapsed

Highly sensitive dry developable deep UV photoresist

Abstract

Inventors

Bibliographic Details

Claims Analysis

References Cited (Backward Citations)

USPTO Annuity & Maintenance Windows

Assigned Categories & Tags

Assign Category Tag