Photo-stabilized cyanine dyes and optical recording media

• US 6,071,672 A
• Filed: 10/09/1998
• Issued: 06/06/2000
• Est. Priority Date: 02/10/1997
• Status: Expired due to Term

• Current Assignee: Sumitomo Seika Chemicals Company Limited, TDK Corporation
• Original Assignee: Sumitomo Seika Chemicals Company Limited, TDK Corporation
• Inventors: Suzuki, Michio, Kimura, Satoshi, Hirako, Kazuyoshi, Shinkai, Masahiro, Kitagawa, Sumiko, Namba, Kenryo
• Primary Examiner(s): Angebranndt, Martin
• Application Number:
  US09/169,009
• Time in Patent Office: 606 Days
• Field of Search: 430/270.16, 430/945, 430/270.21, 430/270.2, 549/3, 544/109, 544/145, 546/187
• US Class Current: 430/270.18
• CPC Class Codes: C09B 23/04 one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
• CPC Class Codes: C09B 23/06 three >CH- groups, e.g. carbocyanines
• CPC Class Codes: C09B 23/083 five >CH- groups
• CPC Class Codes: G11B 7/2472 cyanine
• CPC Class Codes: G11B 7/2495 as anions
• CPC Class Codes: G11B 7/2531 comprising glass
• CPC Class Codes: G11B 7/2533 comprising resins
• CPC Class Codes: G11B 7/2534 polycarbonates [PC]
• CPC Class Codes: G11B 7/2536 polystyrene [PS]
• CPC Class Codes: G11B 7/2542 consisting essentially of organic resins
• CPC Class Codes: G11B 7/259 based on silver
• CPC Class Codes: G11B 7/2595 based on gold
• CPC Class Codes: Y10S 430/146 Laser beam

Abstract

The cyanine dyes of the invention are well soluble in solvents having a high evaporation rate and stable against light, and thus effective for improving productivity and realizing optical recording media, especially CD-R and DVD-R optical discs, having improved light resistance.

The optical recording medium of the invention uses a photo-stabilized cyanine dye which is obtained as a counter ion bonded compound between an anion of the formula (1) and a cation of the formula (2): ##STR1## wherein R₀₁ and R₀₂ each are ##STR2## wherein each of R₁₁ and R₁₂ is an alkyl group of 1 to 4 carbon atoms or phenyl group, ##STR3## wherein m is equal to 3, 4, 5 or 6, ##STR4## or phenyl groups; M is a transition metal; each of Z₁ and Z₂ is a fused benzene ring or fused naphthalene ring; each of R₂₁ and R₂₂ is an alkyl group; and n is equal to 0, 1 or 2.

Claims

1. A photo-stabilized cyanine dye, comprising a counter ion bonded compound of a substituted benzenedithiol metal complex anion of the formula (I) and a cyanine dye cation of the formula (II):

##STR65## wherein R₀₁ and R₀₂ are each independently;

##STR66## wherein each of R₁₁ and R₁₂ is alkyl of 1 to 4 carbon atoms or optionally substituted phenyl;

##STR67## wherein m is equal 3, 4, 5 or 6;

##STR68## or an optionally substituted phenyl;

M is a transition metal;

each of Z₁ and Z₂ is a fused benzene ring or fused naphthalene ring;

each of R₂₁ and R₂₂ is alkyl; and

n is equal to 0, 1 or 2.

2. The photo-stabilized cyanine dye of claim 1, wherein R₀₁ and R₀₂ are each independently ##STR69##

3. The photo-stabilized cyanine dye of claim 1, wherein R₂₁ and R₂₂ are each ethyl, ethyl or propyl.

4. The photo-stabilized cyanine dye of Claim 1, wherein R₀₁ and R₀₂ are selected from the group consisting of

5. The optical recording medium of claim 1, wherein said transition metal M is selected from the group consisting of Fe, Co, Ni, Cu and Pt.

6. The optical recording medium of claim 5, wherein said transition metal M is Cu.

7. A solution, comprising:

a) the photo-stabilized cyanine dye of claim 1, and

b) a solvent for said photo-stabilized cyanine dye, said solvent having an evaporation rate which is sufficiently high to reduce spin coating time.

8. The solutoin of claim 7, wherein said solvent is 2,2,3,3-tetrafluoropropanol.

9. An optical recording medium, comprising a recording layer containing a counter ion bonded compound of a substituted benzenedithiol metal complex anion of the formula (1) and a cyanine dye cation of the formula (2):

##STR70## wherein R₀₁ and R₀₂ are each independently;

##STR71## wherein each of R₁₁ and R₁₂ is alkyl of 1 to 4 carbon atoms or optionally substituted phenyl;

##STR72## wherein m is equal to 3, 4, 5 or 6;

##STR73## or an optionally substituted phenyl;

each of Z₁ and Z₂ is a fused benzene ring or a fused naphthalene ring;

each of R₂₁ and R₂₂ is alkyl;

and n is equal to 0, 1 or 2;

and M is a transition metal.

10. The optical recording medium of claim 9, wherein said recording layer is formed by coating a solution using a solvent having a vapor pressure of at least 5.3 Torr at 25°

C.

11. The optical recording medium of claim 9, wherein said recording layer further contains at least one other dye.

12. An optical recording, comprising a substrate having a recording layer thereon, wherein a counter ion bonded compound contained in the recording layer is a salt of a substituted benzene dithiol metal complex of the formula (1) and a cyanine dye cation of the formula (3):

##STR74## wherein R₀₁ and R₀₂ are each independently;

##STR75## wherein each of R₁₁ and R₁₂ is alkyl of 1 to 4 carbon atoms or optionally substituted phenyl;

##STR76## wherein m is equal 3, 4, 5 or 6;

##STR77## or an optionally substituted phenyl;

M is a transition metal;

wherein each of Q₁ and Q₂ is a group of atoms for forming a 5-membered nitrogenous heterocyclic ring which is optionally fused, each of R₂₁ and R₂₂ is alkyl, and L is a methine chain for completing the cyanine dye.