Ocg Microelectronic Materials, Inc.

Olin Hunt Specialty Products Inc.

Thomas R Sarubbi

Joseph J Sizensky

Andrew J Blakeney

Medhat A Toukhy

Alfred T Jeffries, Iii

A phenolic novolak composition prepared by a process comprising the steps of:

High ortho-ortho bonded novolak binder resins and their use in a process

A phenolic novolak composition prepared by a process comprising the steps of: (1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho--ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and (2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C. to form a phenolic novolak having a weight average molecular weight of 3,000 to 40,000, having ortho--ortho bonding of between 50% and 70% of the methylene bonds between the phenolic moieties, and having a time to clear of at least 20 seconds per micron; wherein the mole ratio of said second aldehyde source to said total phenolic moieties is less than about 0.8:1.0.

High ortho-ortho bonded novolak binder resins and their use in

A novolak resin composition comprising at least one unit of the reaction product of a para-, para-bonded bisphenol having formula (A): ##STR1## wherein R.sub.1 =hydrogen, lower alkyl group having 1-4 carbon atoms, halogen, or lower alkoxy group having 1-4 carbon atoms;

Selected structurally defined novolak binder resins and their use in

A novolak resin composition comprising at least one unit of the reaction product of a para-, para-bonded bisphenol having formula (A): ##STR1## wherein R.sub.1 =hydrogen, lower alkyl group having 1-4 carbon atoms, halogen, or lower alkoxy group having 1-4 carbon atoms; wherein

Radiation-sensitive compositions using novolak resins made from a

Process for producing dimer-free phenolic polymers, particularly novolak polymers produced from cresol mixtures, and photoresist compositions containing such dimer-free novolak polymers. The process comprises reacting phenolic polymers containing phenolic dimers with a capping agent, such as a silylating agent, to cap all of the phenolic hydroxy groups. This reduces the distillation temperature of the capped dimers and renders the capped polymer stable at such distillation temperature. The capped dimers are distilled off, and finally the phenolic polymer is uncapped. Dimer-free novolaks produce scum-free developed photoresist images.

Photoresist composition containing diazoquinone photosensitizer and

Process for selective removal of dimeric species from phenolic polymers

A phenolic novolak resin comprising the product of a condensation reaction of an aldehyde comprising a haloacetaldehyde source or a mixture of a haloacetaldehyde source and a formaldehyde source with a phenolic monomer comprising at least one compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are individually selected from hydrogen or a one to four carbon alkyl group and wherein the ratio of total carbon atoms in the sum of R.sub.1, R.sub.2 and R.sub.3 to the total number of phenolic nuclei in said resin is from about 0.5:1 to about 1.5:1 in the presence of a solvent; said resin made by employing a molar ratio of total aldehyde to total phenolic monomers from about 0.33:1 to about 0.70:1. These phenolic resins are suitable for use in light-sensitive compositions (e.g. positive-working photoresists).

Thermally stable phenolic resin compositions and their use in

A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-napthoquinone diazide sensitizers) to prepare a light-sensitive composition useful in a method for forming a positive photoresist image.

Thermally stable light-sensitive compositions with o-quinone diazide and

Process of forming resist image in positive photoresist with thermally

A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms, and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-naphthoquinone diazide sensitizers) to prepare a light-sensitive composition useful as a positive-working photoresist.

Thermally stable phenolic resin compositions with ortho, ortho methylene

Light-sensitive o-quinone diazide composition and product with phenolic

A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-naphthoquinone diazide sensitizers ) to prepare a light-sensitive composition useful as a positive-working photoresist.

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Providence, RI, United States of America

Thomas R Sarubbi