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EP0250099A2
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Organic nonlinear optical material
Assignee: Toray Industries Inc
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Filing: 1987-05-20
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Granted: —
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Expires: 2007-05-20
Abstract
Abstract The present invention provides an organic nonlinear optical material comprising a benzylidene-aniline derivative having an electron-donating substituent introduced at the 4-position and an electron-accepting substituent introduced at the 4ʹ-position, by following two contrivances: (l) selecting as the conjugated π electronic system a benzylidene-aniline derivative having a large molecular hyperpolarizability and yet a dipole moment as small as those of benzene derivatives, and (2) introducing a molecular alignment-regulating substituent. The centrosymmetry in the bulk state of the material, for example, in the crystal state, is destroyed and the molecular alignment is regulated to such a bulk structure in that the optical nonlinearity possessed by the molecule is effectively utilized. The material shows even a large optical nonlinearity never attained by the conventional techniques. The intermolecular cohesive force due to the π electron interaction between the molecules in the present invention is larger than that between benzene derivatives. Consequently, the material has, comparatively, a high melting point, a low subliming property, and a low water-absorbing property. In conclusion, a practically invaluable nonlinear optical material having a high durability in the bulk state and an excellent resistance to laser damage can be provided.
Inventors
- 👤 Tetsuya Tsunekawa
- 👤 Tetsuya Gotoh
- 👤 Keiichi Egawa
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-06 12:14
CPC Classifications
G; G02; G02F; G02F1/00; G02F1/35; G02F1/355; G02F1/361; G02F1/3611; C; C07; C07D; C07D319/00; C07D319/10; C07D319/14; C07D319/16; C07D319/18
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
58 words
An organic nonlinear optical material which comprises a benzylidene-aniline derivative having an electron-donating substituent (D) at the 4-position, an electron-accepting substituent (A) at the 4ʹ-position and at least one substituent having a function of regulating the molecular alignment in the crystal at any substitutable position, and having a an optical nonlinearity at least l0 times that of urea.
Claim 2
Dependent Claim
58 words
An organic nonlinear optical material which comprises a benzylidene-aniline derivative having an electron-donating substituent (D) at the 4-position, an electron-accepting substituent (A) at the 4ʹ-position and at least one substituent having a function of regulating the molecular alignment in the crystal at any substitutable position, and having a an optical nonlinearity at least l0 times that of urea.
Claim 3
Dependent Claim
77 words
An organic nonlinear optical material as set forth in claim l, wherein at least one of R₁ through R₉ in the following formula l is a substituent having a function of regulating the molecular alignment in the crystal: wherein D stands for an electron-donating substituent, A stands for an electron-accepting substituent, and R₁ through R₉ stand for a hydrogen atom or an optional substituent, wherein at least one of R₁ through R₉ is a molecular alignment-regulating substituent.
Claim 4
Dependent Claim
27 words
An organic nonlinear optical material as set forth in claim 2, wherein the water-solubility of said material at 25°C is lower than l.0 × l0⁻² g/l00 ml.
Claim 5
Dependent Claim
29 words
An organic nonlinear optical material as set forth in claim 2 or claim 3, wherein the optical nonlinearity of said material is at least l50 times that of urea.
Claim 6
Dependent Claim
29 words
An organic nonlinear optical material as set forth in any of claims 2 to 4, wherein the molecular alignment-regulating substituent in the formula [l] is a hydrogen bond-forming substituent.
Claim 7
Dependent Claim
34 words
An organic nonlinear optical material as set forth in any of claims 2 to 5, wherein the molecular alignment-regulating substituent in the formula [l] is a substituent which can cause a large steric hindrance.
Claim 8
Dependent Claim
37 words
An organic nonlinear optical material as set forth in any of claims 2 to 6, wherein the combination of the electron-donating substituent D and the electron-accepting substituent A is a combination of relatively strong and weak substituents.
Claim 9
Dependent Claim
24 words
An organic nonlinear optical material as set forth in any of claims 2 to 7, wherein the electron-accepting substituent A is a nitro group.
Claim 10
Dependent Claim
28 words
An organic nonlinear optical material as set forth in any of cIaims 2 to 8, wherein the electron-donating substituent D is a hydroxyl group or an alkoxy group.
Claim 11
Dependent Claim
28 words
An organic nonlinear optical material as set forth in any of cIaims 2 to 8, wherein the electron-donating substituent D is a hydroxyl group or an alkoxy group.
Claim 12
Dependent Claim
34 words
l0. An organic nonlinear optical material as set forth in claim 2, wherein the electron-donating substituent D is a hydroxyl group or an alkoxy group and the electron-accepting substituent A is a nitro group.
Claim 13
Dependent Claim
25 words
An organic nonlinear optical material as set forth in any of claims 2 to l0, wherein R₉ in the formula [l] is a hydrogen atom.
Claim 14
Dependent Claim
27 words
An organic nonlinear optical material as set forth in claim ll, wherein seven of R₁ through R₈ in the formula [l] also stand for a hydrogen atom.
Claim 15
Dependent Claim
32 words
An organic nonlinear optical material as set forth in claim ll, wherein R₁ through R₄ , and three of R₅ through R₈ in the formula [l] also stand for a hydrogen atom.
Claim 16
Dependent Claim
27 words
An organic nonlinear optical material as set forth in claim l3, wherein the molecular alignment-regulating substituent is located at the ortho position to the electron-donating substituent D.
Claim 17
Dependent Claim
23 words
An organic nonlinear optical material as set forth in claim 2, wherein the molecular alignment-regulating substituent is a substituent containing an amide bond.
Claim 18
Dependent Claim
20 words
An organic nonlinear optical material as set forth in claim 2, wherein the molecular alignment-regulating substituent is a halogen atom.
Claim 19
Dependent Claim
24 words
An organic nonlinear optical material as set forth in claim l5, wherein the molecular alignment-regulating substituent containing an amide bond is an alkanoylamino group.
Claim 20
Dependent Claim
19 words
An organic nonlinear optical material as set forth in claim l7, wherein the alkanoylamino group is an acetylamino group.
Claim 21
Dependent Claim
19 words
An organic nonlinear optical material as set forth in claim l7, wherein the alkanoylamino group is a halogenoacetylamino group.
Claim 22
Dependent Claim
17 words
An organic nonlinear optical material as set forth in claim 2, wherein the benzylidene-aniline derivative is 4ʹ-nitrobenzylidene-3-acetylamino-4-methoxyaniline.
Claim 23
Dependent Claim
18 words
2l. An organic nonlinear optical material as set forth in claim 2, wherein the benzylidene-aniline derivative is 4ʹ-nitrobenzylidene-3-bromoacetylamino-4-methoxyaniline.
Claim 24
Dependent Claim
17 words
An organic nonlinear optical material as set forth in claim 2, wherein the benzylidene-aniline derivative is 4ʹ-nitrobenzylidene-3-chloroacetylamino-4-methoxyaniline.
Claim 25
Dependent Claim
17 words
An organic nonlinear optical material as set forth in claim 2, wherein the benzylidene-aniline derivative is 4ʹ-nitrobenzylidene-3-chloro-4-hydroxyaniline.
Claim 26
Dependent Claim
30 words
An organic nonlinear optical material as set forth in claim 2, wherein all or a part of hydrogen atoms of the benzylidene-aniline derivative represented by the formula [l] are deuterated.
Claim 27
Dependent Claim
81 words
An organic nonlinear optical material as set forth in claim l, which comprises a benzylidene-aniline derivative having an electron-donating substituent with a function of regulating the molecular alignment in the crystal at a position Dʹ in the following formula [2] and having an optical nonlinearity at least l0 times that of urea: wherein Dʹ stands for an electron-donating and molecular alignment-regulating substituent, A stands for an electron-accepting substituent, and R₁ through R₉ stand for a hydrogen atom or an optional substituent.
Claim 28
Dependent Claim
24 words
An organic nonlinear optical material as set forth in claim 25, wherein the water-solubility is lower than l.0 × l0⁻² g/l00 ml at 25°C.
Claim 29
Dependent Claim
26 words
An organic nonlinear optical material as set forth in claim 25 or claim 26, wherein the optical nonlinearity is at least l50 times that of urea.
Claim 30
Dependent Claim
49 words
An organic nonlinear optical material as set forth in any of claims 25 to 27, wherein the electron-donating and molecular alignment-regulating substituent (Dʹ) is an alkoxy group -OR in which R stands for an alkyl group, an allyl group, an aryl group, an aralkyl group or a derivative thereof.
Claim 31
Dependent Claim
24 words
An organic nonlinear optical material as set forth in any of claims 25 to 28, wherein the electron-accepting substituent (A) is a nitro group.
Claim 32
Dependent Claim
17 words
An organic nonlinear optical material as set forth in claim 25, wherein the benzylidene-aniline derivative is 4ʹ-nitrobenzylidene-3,4-ethylenedioxy-aniline.
Claim 33
Dependent Claim
30 words
3l. An organic nonlinear optical material as set forth in claim 25, wherein all or a part of hydrogen atoms of the benzylidene-aniline derivative represented by the formula are deuterated.
References Cited (Backward Citations)
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