Photoactive compounds and compositions

{
  "publication_number": "US5618932A",
  "country": "US",
  "kind": "A",
  "title": "Photoactive compounds and compositions",
  "abstract": "A new photoactive compound for use in the formulation of a photoresist comprises a bisphenol compound having an alkyl linkage substituted with a heterocyclic group. The new photoactive compound may be admixed with an alkali soluble resin to formulate a photoresist composition. The new photoactive compounds exhibit enhanced long term solubility in conventional photoresist solvents.",
  "claims": [
    "1. A compound corresponding to the formula: ##STR11## whereby each Y is independently selected from the group consisting of hydrogen, lower alkyl having from 1 to 5 carbon atoms, R'SO 2, acyl, (R') 3 Si and a naphthoquinone diazide sulfonyl group where each R' is independently selected from the group of lower alkyl having from 1 to 5 carbon atoms and aryl provided that at least one Y is a naphthoquinone diazide sulfonyl group; R is a member selected from the group consisting of hydrogen, lower alkyl having from 1 to 5 carbon atoms, cyclic alkyl, and aryl; R 1, R 2 and R 3 are each independently selected form the group consisting of hydrogen, hydroxyl, lower alkyl having from 1 to 5 carbon atoms, cyclic alkyl, aryl, alkoxy, alkenyl, alkynyl, nitro, alkanoyl, carboxyl, sulfonyl and halogen; and Q is a five member heterocyclic group.",
    "2. The compound of claim 1 where the heterocyclic group contains a member selected from the group consisting of oxygen, sulfur and nitrogen in the heterocyclic ring.",
    "3. The compound of claim 1 where the heterocyclic group contains sulfur in the heterocyclic group.",
    "4. The compound of claim 1 where the heterocyclic group contains oxygen in the heterocyclic ring.",
    "5. The compound of claim 1 where one of said Ys is hydrogen.",
    "6. The compound claim 1 where each Y is a naphthoquinone diazide sulfonyl group.",
    "7. The compound of claim 1 where at least one of R 1, R 2 or R 3 is hydroxyl.",
    "8. A compound corresponding to the formula: ##STR12## where each Y is independently selected from the group consisting of hydrogen, lower alkyl having from 1 to 5 carbon atoms, R'SO 2, acyl, (R') 3 Si and a naphthoquinone diazide sulfonyl group where each R' is independently selected from the group of lower alkyl having from 1 to 5 carbon atoms and aryl provided that at least one Y is a naphthoquinone diazide sulfonyl group; X is a member selected for the group consisting of oxygen and sulfur; R is a member selected from the group consisting of hydrogen, lower alkyl having from 1 to 5 carbon atoms, cyclic alkyl, aryl and a heterocyclic; and R 1, R 2 and R 3 are each independently selected form the group consisting of hydrogen, hydroxyl, lower alkyl having from 1 to 5 carbon atoms, cyclic alkyl, aryl, alkoxy, alkenyl, alkynyl, nitro, alkanoyl, carboxyl, sulfonyl and halogen; and R 4 is selected from the group consisting of hydrogen, lower alkyl having from 1 to 5 carbon atoms, alkoxy, alkenyl, alkynyl, carboxyl, alkoxy, carbonyl, nitro and halogen.",
    "9. The compound of claim 8 where each Y is a naphthoquinone diazide sulfonyl group.",
    "10. The compound of claim 8 where at least one of R 1, R 2 or R 3 is hydroxyl.",
    "11. A method for formation of a diazo ester, said method comprising the reaction of a molar excess of a phenol with a carbonyl in the presence of an acid catalyst in accordance with the following scheme: ##STR13## where X is a member selected for the group consisting of oxygen and sulfur; R is a member selected from the group consisting of hydrogen, lower alkyl having from 1 to 5 carbon atoms, cyclic alkyl, and aryl; and R 1, R 2 and R 3 are each independently selected form the group consisting of hydrogen, hydroxyl, lower alkyl having from 1 to 5 carbon atoms, cyclic alkyl, aryl, alkoxy, alkenyl, alkynyl, nitro, alkanoyl, carboxyl, sulfonyl and halogen; and R 4 is selected from the group consisting of hydrogen, lower alkyl having from 1 to 5 carbon atoms, alkoxy, alkenyl, alkynyl, carboxyl, alkoxy, carbonyl, nitro and halogen and reacting the compound thus formed with a naphthoquinone diazide sulfonyl chloride.",
    "12. The method of claim 1 where the acid is a mineral acid.",
    "13. The method of claim 11 where there are at least two moles of the phenol per mole of the carbonyl compound.",
    "14. The method of claim 11 where the napthoquinone diazide sulfonyl chloride is a 1,2-naphthoquiunone-(2)-diazo-4-sulfonyl acid chloride.",
    "15. The method of claim 11 where the naphthoquinone diazide sulfonyl chloride is a 1,2-naphthoquinoe diazide-(2)-diazo-5-sulfonyl acid chloride."
  ],
  "description_excerpt": "1. Field of the Invention\n\nThe invention relates to phenolic polynuclear compositions useful as intermediates for the formation of photoactive compounds. Further, the invention relates to such photoactive compounds formed by the esterification of these phenolic compositions with sulfonyl halides of naphthoquinone diazide.\n\n2. Description of the Background Art\n\nPhotoresists are photosensitive films used for transfer of an image to a substrate. They may be negative or positive acting. After a coating of a photoresist is formed on a substrate, the coating is selectively exposed through a photomask to a source of activating energy such as ultraviolet light. The photomask has areas that are opaque to activating radiation and other areas that are transparent to activating radiation. The pattern in the photomask of opaque and transparent areas define a desired image to be transferred to a substrate. A relief image is provided upon development of the latent image patterned in the resist coating. The background and use of photoresists are generally described, for example, in Deforest, Photoresist Materials and Processes, McGraw Hill Book Company, New York (1975), and by Moreau, Semiconductor Lithography, Principles, Practices and Materials, Plenum Press, New York (1988).\n\nVarious attempts have been made to alter the make-up of photoresist compositions to improve performance or functional properties. In particular, a variety of photoactive compounds have been reported including photoactive compounds that contain more than one diazoquinone moiety.",
  "cpc": [
    "C07D 307/42",
    "C07D 333/16",
    "G03F 7/022"
  ],
  "ipc": [
    "C07D 307/42",
    "C07D 333/16",
    "G03F 7/022"
  ],
  "assignees": [
    "Shipley Co LLC"
  ],
  "inventors": [
    "Anthony Zampini",
    "Ashish Pandya"
  ],
  "filing_date": "1995-05-24",
  "publication_date": "1997-04-08",
  "grant_date": "1997-04-08",
  "priority_date": "1995-05-24",
  "application_number": "US-44933495-A",
  "family_id": "23783769",
  "cited_by_count": 5,
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}