Photoimageable compositions containing substituted 1, 2 dihalogenated ethanes for enhanced printout image

• US 5,407,783 A
• Filed: 03/09/1994
• Issued: 04/18/1995
• Est. Priority Date: 07/22/1993
• Status: Expired due to Term

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Caruso, Thomas C.
• Primary Examiner(s): McCamish, Marion E.
• Assistant Examiner(s): CODD, BERNARD P
• Application Number:
  US08/205,211
• Time in Patent Office: 405 Days
• Field of Search: 430/281, 430/286, 430/288, 430/338, 430/340, 430/344
• US Class Current: 430/288.1
• CPC Class Codes: G03C 1/675 Compositions containing polyhalogenated compounds as photosensitive substances for photopolymerisable or photocrosslinkable compositions G03F7/028, covered by G03C1/72
• CPC Class Codes: G03C 1/725 containing inorganic compounds
• CPC Class Codes: G03F 7/105 having substances, e.g. indicators, for forming visible images

Abstract

Photoimageable compositions, photoimageable resist compositions, and photoimageable resist elements that afford enhanced, storage stable printout images are disclosed which include a substituted 1,2-dibromoethane and a leuco dye.

Claims

1. A photoimageable composition which comprises:

(a) a substituted 1,2-dihalogenated ethane having the structure;

##STR5## wherein;

X₁ and X₂ are independently either bromine or chlorine;

R₁ is C₆ -C₁₀ aryl, or aroyl, and;

R₂ is C₆ -C₁₀ aryl, aroyl, acyl, or an electron withdrawing group other than halogen; and

R₃ and R₄ are independently C₆ -C₁₀

aryl, C₁ -C₁₀ alkyl, H, or an electron withdrawing group other than halogen, with the proviso that any two of R₁, R₂, R₃ and R₄ groups can form a 5- to 8-membered ring structure;

with the proviso that when R₁ or R₃ is C₆ -C₁₀ aryl, R₂ and R₄ are not aryl;

(b) a leuco dye; and

(c) a photoinitiator or photoinitiator system.

2. The photoimageable composition of claim 1 which additionally contains

(a) at least one ethylenically unsaturated monomer and

(b) at least one polymeric binder.

3. The photoimageable composition of claim 2 in which said polymeric binder is a carboxylic acid containing copolymer binder, wherein the level of carboxylic acid groups allows for development in 0.85% aqueous sodium carbonate by weight at 30°

C. within two minutes, having structural units;

##STR6## in which;

R₁ is H or alkyl;

R₂ is phenyl or CO₂ R₃ ; and

R₃ is H or alkyl.

4. The photoimageable composition of claim 3 wherein the carboxylic acid containing copolymer binder is comprised from the group of structural units consisting of acrylic acid, methacrylic acid, methyl methacrylate, styrene, ethyl acrylate, butyl methacrylate, and butyl acrylate.

5. The photoimageable composition of claim 2, wherein the photoinitiator is selected from the group consisting of benzophenone, 4,4'"'"'-bis(diethylamino)benzophenone, 4,4-bis(dimethylamino)benzophenone, thioxanthone, a substituted thioxanthone, benzil dimethyl ketal, 4-methyl-4-trichloromethyl-2,5-cylcohexadienone, ethyl p-dimethylaminobenzoate, and 2-(2-chlorophenyl)-4,5-diphenylimidazole dimer.

6. The photoimageable composition of claim 2 wherein the monomeric component comprises a compound having at least two ethylenically unsaturated groups.

7. The photoimageable composition of claim 6 wherein the monomeric component is selected from the group consisting of tripropylene glycol diacrylate, trimethylolpropane triacrylate, polyoxyethylated trimethylolpropane triacrylate and triethylene glycol dimethacrylate.

8. The photoimageable composition of claim 1 wherein the substituted 1,2-dihalogenated ethane is a 1,2-dibromoethane selected from the group consisting of:

10,11-dibromodibenzosuberone,

2,3-dibromo-3-phenylpropiophenone,

ethyl 2,3-dibromo-3-phenylpropionate,

trans-1,2-dibromoacenaphthene,

2,3-dibromo-3-phenylpropionic acid,

1,2-dibromo-1,2-dibenzoylethane,

3,4-dibromo-4-phenyl-2-butanone,

2,3-dibromo-3-(p-nitrophenyl)propiophenone,

2,3-dibromo-3-(p-cyanophenyl)propiophenone,

2-bromo-2-(alpha-bromobenzyl)-1-indanone, and

2-bromo-2-(alpha-bromo-p-cyanobenzyl)-1-indanone.

9. The photoimageable compositions of claim 1 wherein the leuco dye is:

space="preserve" listing-type="equation">CH[C.sub.6 H.sub.4 N(R).sub.2 ].sub.3

in which R is alkyl of one to six carbon atoms.

10. The photoimageable compositions of claim 1 wherein the 1,2-dihalogenated ethane comprises 0.01 to 10.0% of the total composition by weight.