JPH05294889A - 2-@(3754/24)2'-chlorobenzal)-3-phenylidan-1-one and nonlinear optical material using the same - Google Patents

Abstract

PURPOSE:To obtain a new compound to be a nonlinear optical material having high optical nonlinearity. CONSTITUTION:The objective 2-(2'-chlorobenzal)-3-phenylindan-1-one of the formula. This compound of the formula is obtained by thermally refluxing, e.g. 2-chlorobenzaldehyde and 3-phenylindan-1-one in the presence of an alkaline catalyst such as NaOH in a solvent such as methanol.

Description

Detailed Description of the Invention

[0001]

The present invention relates to an optical parametric oscillation,
A novel 2-based material used for nonlinear optical materials that are important in optical signal processing systems such as harmonic generation and optical switching.
(2'-Chlorobenzal) -3-phenylindane-1
-ON and a non-linear optical material using this compound.

[0002]

2. Description of the Related Art Nonlinear optical materials, which are considered to play an important role in the fields of optical communication and the like, exhibit functions such as optical mixing, parametric oscillation, and generation of optical harmonics based on the nonlinear response of materials. , Conventionally, KH ₂ PO ₄ , NH ₄ H ₂
Inorganic crystals such as PO ₄ have been used. However, these materials have not met the aforementioned requirements because of their deliquescent properties, low non-linear susceptibility and low fracture threshold. In addition, the primary and secondary electro-optic effects that can be used for optical switching are essentially the same nonlinear polarization effects as the secondary and tertiary nonlinear optical effects, respectively, so basically the same materials may be used. There is. Since the response speed of the inorganic material is slow, the frequency band is narrowed. Organic nonlinear optical materials utilizing polarization of π-electron system are widely researched in various fields, because their nonlinear optical constants are larger than inorganic materials, and generally they are excellent in that they have no deliquescent property and have a high threshold for destruction. Development is in progress. For recent achievements, see for example Nonlinear Optical Properties of Organic Moleculars and Crystals (Nonlinear).
Optical Properties of Org
anic Molecules and Crystal
ls) Vol. 1 and Vol. 2, D. S. Cheml
a, J. Zyss Edition (1987 Academic P
(Published by Ress).

However, a material such as a semiconductor laser having a non-linear optical constant large enough to achieve a purpose with a low-power laser has not been found, and further development of a new material is strongly demanded.

[0004]

DISCLOSURE OF THE INVENTION The present invention provides a novel compound which is a novel organic nonlinear optical material having a large nonlinear optical constant and a nonlinear optical material using the same.

[0005]

The present invention comprises 2- (2'-chlorobenzal) -3-phenylindan-1-one represented by the formula [I], a non-linear optical material comprising this compound, and this compound. The present invention relates to a nonlinear optical material composed of the composition.

[Chemical 2] In the present invention, 2- (2 'represented by the above formula [I] is used.
-Chlorobenzal) -3-phenylindan-1-one is used, and this compound is obtained by heating and refluxing 2-chlorobenzaldehyde and 3-phenylindan-1-one in a solvent such as methanol in the presence of an alkali catalyst. It can be synthesized by

The nonlinear optical material according to the present invention is 2- (2'-chlorobenzal) -3 represented by the above formula [I].
-Phenylindan-1-one may be used alone, or a composition in which this compound is dispersed or dissolved in a polymer compound may be used. As the polymer compound, for example, methyl (meth) acrylate (methacrylate or acrylate; hereinafter the same), ethyl (meth) acrylate, n-butyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylic acid,
Homopolymers, copolymers or terpolymers of monomers such as styrene, vinyltoluene, divinylbenzene, vinyl chloride and β-hydroxyethyl (meth) acrylate, polyesters, polyamides, polyurethanes, polycarbonates, cellulose esters and polyethers are used. The compound represented by the formula [I] and the corresponding monomer may be mixed and then polymerized by the action of heat or light to give a composition. The above polymer compound and the compound represented by the formula [I] are appropriately used. The composition may be obtained by dissolving and mixing with a suitable solvent and then removing the solvent. In the former case, the non-linear optical performance can be improved by performing poling during the polymerization, or by performing poling after obtaining the composition for both the former and the latter. Alternatively, in the presence of a DC electric field, the compound of the above formula [I] is heated to a temperature equal to or higher than the melting point and melted, and then slowly cooled or rapidly cooled while maintaining the electric field, thereby controlling the alignment state of the molecules. It is also possible to obtain a high-performance single crystal or molecular glass.

The above-mentioned non-linear optical materials can be used in the form of bulk crystals independently, or in fiber type, slab type, plane type,
It can be used as a part of a waveguide type optical element such as a channel type. Examples of the nonlinear optical element using the above nonlinear optical material include a wavelength conversion element using the second harmonic generation, sum frequency generation or optical parametric oscillation, a phase modulation element using the electro-optic effect, a polarization plane modulation element and the like. ..

[0008]

In the compound of the present invention, which has a carbonyl group as an acceptor group and is conjugated with the styryl π electron system, a large dipole moment is generated by the charge transfer in the excited state and a high hyperpolarizability is obtained. Therefore, a high nonlinear optical effect can be obtained.

[0009]

EXAMPLES The present invention will be described in more detail by way of examples. Synthesis of 2- (2'-chlorobenzal) -3-phenylindan-1-one 2-Chlorobenzaldehyde 0.675 g (4.81 m)
mol) and 3-phenylindan-1-one 1 g (4.
81 mmol) 5 ml of methanol and 35% NaOH
The aqueous solution (0.5 ml) was placed in a 50 ml eggplant-shaped flask, one piece of a boiling stone was added, and a condenser for cooling was attached, and the mixture was heated under reflux for about 1 hour. Crystals appeared when left to cool, so this was filtered off and washed thoroughly with methanol. Yield about 1.35
It was 1 g (85%). The structure of the product was confirmed by nmr and absorption spectrum. The UV-visible absorption spectrum of the methylene chloride solution of this compound is shown in FIG. 1, and the nmr spectrum of the deuterated chloroform solution is shown in FIG.

Comparative Examples and Examples 2- (2'-chlorobenzal) -3-phenylindan-1-one absorption maximum wavelength (λmax, methylene chloride solution) and the second harmonic generation efficiency (SH) determined by the powder method.
Table 1 shows the G efficiency, the intensity ratio of the second harmonic when urea is 1, and the melting point. The powder method is outlined in the Journal of Applied Physics.
applied Physics) vol. 36 (196
3) 3798-3813.
A sample powder classified to a particle size of 50 to 150 μm is sandwiched between non-fluorescent slide glasses (made by Matsunami Glass), and a pulsed Nd: YAG laser (SL30 manufactured by Spectrolaser System) is manufactured.
Type 3, maximum output 850 mJ, half width 15 ns, output 60 MW per pulse, beam diameter 9.5 mm, wavelength 1.0
Light irradiation was performed at 64 μm and a repetition frequency of 10 Hz). The intensity of the generated second harmonic of 532 nm was measured by a photomultiplier tube through an infrared filter and a UV filter.

[0011]

[Table 1]

[0012]

By the novel 2- (2'-chlorobenzal) -3-phenylindan-1-one according to the present invention, a nonlinear optical material having high optical nonlinearity can be obtained.

[Brief description of drawings]

FIG. 1 2- (2′-chlorobenzal) -obtained in Examples
It is an ultraviolet-visible absorption spectrum of a methylene chloride solution of 3-phenylindan-1-one.

FIG. 2 shows 2- (2′-chlorobenzal) -obtained in the example.
It is a nmr spectrum of a deuterated chloroform solution of 3-phenylindan-1-one.

Claims (3)

[Claims] 1. 2- (2′-chlorobenzal) -3-phenylindan-1-one represented by the formula [I]. [Chemical 1] 2. A nonlinear optical material consisting of 2- (2'-chlorobenzal) -3-phenylindan-1-one. 3. A nonlinear optical material comprising a composition containing 2- (2′-chlorobenzal) -3-phenylindan-1-one.