US3578456A - Non-silver photosensitive composition sensitized with rubrene - Google Patents

Non-silver photosensitive composition sensitized with rubrene Download PDF

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Publication number
US3578456A
US3578456A US728002A US3578456DA US3578456A US 3578456 A US3578456 A US 3578456A US 728002 A US728002 A US 728002A US 3578456D A US3578456D A US 3578456DA US 3578456 A US3578456 A US 3578456A
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composition
rubrene
compound
photosensitive composition
compositions
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US728002A
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Victor P Petro
James R Cable
Eugene Wainer
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Horizons Research Inc
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Horizons Research Inc
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances

Definitions

  • Non-silver photosensitive compositions adapted to be developed by optical means, said compositions being provided with sensitivity extending into the red by the addition thereto of merocarbocyanines or a merocyanine.
  • This invention relates to photosensitive non-silver compositions, such as those described in US. Pats. 3,042,515 and 3,095,303 and improvements thereon, described in copending US. patent applications, including Ser. No. 696,100 filed Jan. 8, 1968 and Ser. No. 711,832 filed Mar. 11, 1968. More particularly, it relates to a means for extending the spectral response of such compositions.
  • compositions described in the earlier of the above noted pending patent applications include compositions comprising the following or their equivalents 4-p-dimethylaminostyryl quinoline (other dye base, e.g.
  • the photographic response of the composition is enhanced by treating the styryl quinoline with an alkali metal hydroxide, as described in the second of said above noted applications. Briefly, this treatment consists of digesting the dye base with an appropriate alkali metal hydroxide and the isolation of the stabilized dye base by precipitation and vacuum drying.
  • the present invention is directed to the extension of the spectral sensitivity to the green portion of the spectrum of such compositions by the addition of a polynuclear hydrocarbon to the composition and further toward the red portions of the spectrum by the addition of an indanedione or a rhodanine compound.
  • FIG. 1 depicts the spectral sensitivity of a composition as defined in Example 1 and also the spectral sensitivity of a second composition to which rubrene has been added to enhance the spectral sensitivity.
  • FIG. 2 depicts a similar comparison, except that the added constituent is 3-ethyl-5-[l-methyl-4(1H)-quinolylidene)-ethylidene]-rhodanine instead of rubrene.
  • FIG. 3 is a similar comparison in which the added compound is 2 [(3 ethyl-2(3H)-benzoxazolyidene)-2-butenylidene]-1,3-indanedi0ne instead of rubrene.
  • composition was prepared by adding the several constitutents, preferably in the order given, to a 10% solution of polystyrene in benzene.
  • the resulting composition was spread on a film of Mylar or glass or other suitable substratein a wet thickness of 0.0015 inch-by means of a doctor blade or any other conventional coating technique.
  • Paper or other absorbent substrate may be utilized in which case the substrate itself serves as the binder and hence some or even all of polystyrene can be omitted from the composition when it is applied to such a substrate.
  • the latent image is developed to a visible image by exposing the entire film to radiant energy of an appropriate wavelength (600- 800 m for a period of time in the range of 15 to 300 seconds, the wavelength being selected so that the radiant energy falling on the unexposed portions of film did not contain radiation which would fog the non-image areas of the film.
  • an appropriate wavelength 600- 800 m for a period of time in the range of 15 to 300 seconds, the wavelength being selected so that the radiant energy falling on the unexposed portions of film did not contain radiation which would fog the non-image areas of the film.
  • the amount of energy required to obtain a density of the image obtained by optical development equal to 1 density unit, is a measure of the spectral sensitivity of the film and is shown in the graph labelled Example 1 in FIGS. 1, 2 and 3.
  • FIGS. 2 and 3 the cross hatched area represents the increase in spectral sensitivity produced as a result of adding the compound named in the figures to the composition of Example 1.
  • the several constituents may be replaced by their equivalents, e.g., as described in earlier filed applications.
  • carbon tetrabromide and other halogen containing organic compounds can be used, as described in US. Pat. No. 3,042,514, and instead of the specific styryl quinoline, other related higher 'vinylidene homologues can be used, as described in US, patent application Ser. No. 696,100 filed Jan. 8, 1968.
  • sensitivity to the visible may be extended even further into the red region by incorporation of one or more mercocarbocyanines into the composition of Example 1.
  • a specific member of this general class of compound is 3-ethyl-5-[ (1-methyl-4( lH)-quinolylidene)-ethylidene] rhodanine.
  • R is selected from the group consisting of lower alkyl, aryl and aralkyl
  • Y represents the non-metallic atoms necessary to complete a heterocyclic nucleus with from 5 to 6 atoms in the heterocyclic ring
  • n is an integer of from 1 to 2
  • Q represents the nonmetallic atoms necessary to complete a five-membered or six-membered heterocyclic nucleus.
  • a specific member of this general class of compound is 2 [(3 ethyl 2(3H) benzoxazolylidene) 2 butenylidene] 1,3-indanedione.
  • the spectral sensitivity curve is given by FIG. 3 (1-2 mg. of merocyanine added to Example 1).
  • a non-silver photosensitive composition exhibiting the spectral response of the composition and also a spectral response in the green region of the spectrum, said composition consisting essentially of (1) at least one styryl quinoline dye base; (2) at least one triaryl compound of P, As, Sb or Bi; (3) at least one organic compound having a carbon atom to which at least three halogen atoms are attached, the atoms being Cl, Br or I atoms; and (4) rubrene.
  • composition of claim 1 wherein the organic halogen compound is iodoform.
  • composition of claim 3 wherein the composition contains, as an additional ingredient, a compound which extends the sensitivity further toward the red region and selected from the group consisting of merocyanines.
  • composition of claim 3 wherein the additional ingredient is 2- (3-ethyl-2 3H) -benzoxazolylidene) -2-buttenylidene] -1, 3 -indanedione.
  • composition of claim 1 wherein the triaryl compound is triphenylstibine.
  • composition of claim 3 wherein the additional ingredient is 3-ethyl-5- 1-methyl-4 1H) -quinoly1idene)- ethylidene] -rhodanine.
  • R represents a member selected from the group consisting of alkyl and aralkyl groups, including carboxyalkyl and sulfoalkyl groups
  • n represents a positive integer of l to 2
  • III represents a positive integer of from 1 to 4
  • Q and Z represent the non-metallic atoms necessary to complete a heterocyclic nucleus containing
  • composition of claim 3 wherein the additional compound is merocyanine represented by the generic References Cited UNITED STATES PATENTS 7/ 1963 lSprogue et a1. 96-90 4/1968 Fichter 96-90 NORMAN G. TORCHIN, Examiner R. E. FIGHTER, Assistant Examiner

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Plural Heterocyclic Compounds (AREA)
US728002A 1968-05-09 1968-05-09 Non-silver photosensitive composition sensitized with rubrene Expired - Lifetime US3578456A (en)

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US72800268A 1968-05-09 1968-05-09

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CA (1) CA923747A (https=)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040067537A1 (en) * 2000-07-13 2004-04-08 Hahn Klaus M. Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US20050287518A1 (en) * 2000-07-13 2005-12-29 The Scripps Research Institute Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040067537A1 (en) * 2000-07-13 2004-04-08 Hahn Klaus M. Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US20050287518A1 (en) * 2000-07-13 2005-12-29 The Scripps Research Institute Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US7176037B2 (en) 2000-07-13 2007-02-13 The Scripps Research Institute Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US7662644B2 (en) 2000-07-13 2010-02-16 The Scripps Research Institute Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US7745377B2 (en) 2000-07-13 2010-06-29 The Scripps Research Institute Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation

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DE1905850A1 (de) 1969-12-11
CA923747A (en) 1973-04-03
GB1258634A (https=) 1971-12-30

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