Methine and azamethine dyes based on naphthoquinones in nonlinear optics

• US 5,756,753 A
• Filed: 12/24/1996
• Issued: 05/26/1998
• Est. Priority Date: 06/27/1994
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Sens, Rudiger, Etzbach, Karl-Heinz, Beckmann, Stefan
• Primary Examiner(s): MCKANE, JOSEPH K
• Application Number:
  US08/750,846
• Time in Patent Office: 518 Days
• Field of Search: 548/194, 548/198, 548/136, 548/143, 549/68, 549/74, 558/406, 558/409
• US Class Current: 548/194
• CPC Class Codes: C09B 23/0091 having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol styryl dyes see C09B23/14
• CPC Class Codes: C09B 69/10 Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds addition products of alkylene oxide to dyes, C09B69/00; dyeing with polymeric dyes D06P1/0056
• CPC Class Codes: G02F 1/3611 containing Nitrogen
• CPC Class Codes: G02F 1/3614 Heterocycles having S as heteroatom
• CPC Class Codes: G02F 1/3617 having the non-linear optical group in a side chain

Abstract

Naphthalene derivatives of the formula ##STR1## where the rings A and B may be benzofused,

X is nitrogen or a radical of the formula CH or CH═CH--CH,

Z is a heterocyclic radical or additionally, when x is CH═CH--CH, a 5- or 6-membered aromatic carbocyclic radical, and

R¹, R² and R³ are hydrogen, C₁ -C₄ -alkyl or C₅ -C₇ -cycloalkyl, are useful in nonlinear optics.

Claims

1. A naphthalene compound of the formula (II):

##STR21## wherein;

rings A and B may each be benzofused;

W is a group of the formula CH or CH═

CH--CH;

Z is a 5- or 6-membered aromatic heterocyclic group or, where X is CH═

CH--CH, a 5- or 6membered aromatic carbocyclic group;

R¹, R² and R³ are independently of each other hydrogen, C₁ -C₄ -alkyl or C₅ -C₇ -cycloalkyl.

2. The naphthalene compound of claim 1, wherein rings A and B are not benzofused.

3. The naphthalene compound of claim 1, wherein R¹, R² and R³ are each hydrogen.

4. The naphthalene compound of claim 1, wherein Z is selected from a thiophene, thiazole, oxadiazole or thiadiazole.

5. The naphthalene compound of claim 1, wherein Z is selected from the group consisting of ##STR22## wherein ring K may be benzofused;

L¹ and L² are each independently of each other hydrogen, C₁ -C¹⁰ alkyl, which is unsubstituted or substituted by phenyl, hydroxyl, acryloyloxy- or methacryloyloxy;

phenyl;

or L¹ and L² are together with the nitrogen atom joining them together pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N--(C₁ -C₄ -alkyl) piperazinyl;

L³ and L⁴ are independently of each other hydrogen, C₁ -C₁₀ -alkyl, C₅ -C₇ -cycloalkyl, C₁ -C₁₀ -alkoxy, cyano or halogen; and

L⁵ is hydrogen, C₁ -C₁₀ -alkyl, which is unsubstituted or substituted by phenyl, hydroxyl, acryloyloxy or methacryloyloxy;

C₅ -C₇ -cycloalkyl, phenyl, C₁ -C₁₀ -alkoxy, cyano, nitrogen or halogen.

6. The naphthalene compound of claim 1, wherein Z is selected from a benzene.