Substituted and unsubstituted ring-bridged para-oligophenylene UV laser dyes

• US 4,876,029 A
• Filed: 11/23/1984
• Issued: 10/24/1989
• Est. Priority Date: 03/05/1984
• Status: Expired due to Fees

• Current Assignee: Kernforschungszentrum Karlsruhe GmbH
• Original Assignee: Kernforschungszentrum Karlsruhe GmbH
• Inventors: Ache, Hans-Joachim, Rinke, Monika, Wirth, Hermann O., Gusten, Hans
• Primary Examiner(s): Niebling, John F.
• Assistant Examiner(s): Marquis, Steven P.
• Application Number:
  US06/674,403
• Time in Patent Office: 1,796 Days
• Field of Search: 252/301.17, 372/53, 372/54, 372/52, 549/456, 549/458
• US Class Current: 252/301.17
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H01S 3/213 including an organic dye

Abstract

The present invention relates to laser dyes having improved characteristics comprising substituted and unsubstituted ring-bridged p-oligophenylenes having at least four and no more than 8 phenyl groups. These improved laser dyes can be excited by pump lasers and are capable of producing stimulated coherent emission in the near ultraviolet range, particularly in the range below 400 nm, and have improved photostability. The p-oligophenylenes used according to the invention have the following characteristics:

(a) the number of bridges is a number from 1 to 7 but only one bridge exists between two adjacent phenylene groups;

(b) each bridge in the O,O'"'"'-cis position engages two adjacent phenylene groups;

(c) the bridges represent the same and/or different species from a defined group; and

(d) the phenylene rings may either be unsubstituted, except for the bridges, or one or several phenylene rings in the molecule, independent of whether they are bridged or not, may have one or two radicals R₃ per phenylene ring, with different phenylene rings having the same or different radicals R₃.

Claims

1. A laser dye capable of stimulated coherent emission in the range below 400 nm comprising ring-bridged p-oligophenylenes having at least 4 and no more than 8 phenyl groups, and having at least one bridge between two adjacent phenyl groups but no more than one bridge between any two adjacent phenyl groups.

2. The laser dye as recited in claim 1, wherein the bridges are selected from the group consisting of:

##STR20## and R₁ is an alkyl radical having 1 to 8 carbon atoms and R₂ is the same alkyl radical selected from the group consisting of CH₃, C₂ H₅, n-propyl, isopropyl, n-butyl and isobutyl.

3. The dye as recited in claim 1, wherein the phenyl rings are unsubstituted except for the bridges.

4. The laser dye as recited in claim 1, wherein at least one phenyl ring is substituted with one or two radicals R₃, whether bridged or not, wherein R₃ is an alkyl group having 1 to 5 carbon atoms, CF₃, an alkoxy group having 1 to 8 carbon atoms, an alkoxy group derived from 2- C_2n -C_2n+4 alcohols, wherein (n=a whole number) ≧

1, or an alkoxy group having an oxalkyl side chain with 2 to 5 carbon atoms.

5. The laser dye as recited in claim 4, wherein at least one phenyl ring is substituted with two identical R₃ radicals.

16. The laser dye as recited in claim 1, wherein said ring-bridged p-oligophenylenes consist essentially of ##STR23##

6. In a dye laser the improvement comprising a laser dye capable of stimulated coherent emission in the range below 400 nm which comprises at least one ring-bridged p-oligophenylene having from 4 to 8 phenyl groups, and having one bridge between any two adjacent phenyl groups.

7. The dye laser as recited in claim 6, wherein the bridges are selected from the group consisting of ##STR21## and R₁ is an alkyl radical having 1 to 8 carbon atoms and R₂ is the same alkyl radical selected from the group consisting of CH₃, C₂ H₅, n-propyl, isopropyl, n-butyl and isobutyl.

8. The dye laser as recited in claim 6, wherein the phenyl rings are unsubstituted except for the bridges.

9. The dye laser as recited in claim 6, wherein at least one phenyl ring is substituted with one or two radicals R₃, wherein R₃ is an alkyl group having one to five carbon atoms, CF₃, an alkoxy group having one to eight carbon atoms, an alkoxy group derived from 2-C_2n -C_2n+4 alcohols, wherein n is a whole number ≧

1, or an alkoxy group having an oxalkyl side chain with 2 to 5 carbon atoms.

10. The dye laser as recited in claim 9, wherein at least one phenyl ring is substituted with two identical R₃ radicals.

17. The dye laser as recited in claim 6, wherein said at least one ring-bridged p-oligophenylene consists essentially of ##STR24##

11. In a method of lasing, the improvement comprising a laser dye capable of stimulated coherent emission in the range below 400 nm which comprises at least one ring-bridged p-oligophenylene having from four to eight phenyl groups, and having one bridge between any two adjacent phenyl groups.

12. The method of lasing as recited in claim 11, wherein the bridges are selected from the group consisting of:

##STR22##

13. The method of lasing as recited in claim 11, wherein the phenyl rings are unsubstituted except for the bridges.

14. The method of lasing as recited in claim 11, wherein at least one phenyl ring is substituted with one or two radicals R₃, wherein R₃ is an alkyl group having one to five carbon atoms, CF₃, and alkoxy group having one to eight carbon atoms, an alkoxy group derived from 2-C_2n -C_2n+4 alcohols, wherein n is a whole number ≧

1, or an alkoxy group having an oxalkyl side chain with 2 to 5 carbon atoms.

15. The method of lasing as recited in claim 14, wherein at least one phenyl group is substituted with two identical R₃ radicals.

18. The method of lasing as recited in claim 11, wherein said at least one ring-bridged p-oligophenylene consists essentially of ##STR25##