JPH04108886A - Light control material and light control element containing the same - Google Patents

Abstract

PURPOSE:To obtain a photodimming material giving a photodimming element useful for an indicating device, a light-dimming window or a memory, etc., having excellent resistances to light, heat and water, etc., comprising a suspension containing a specific quinone-based compound as a principal component as particles sensitive to electric field. CONSTITUTION:The objective photodimming material is composed of particles sensitive to electric field contained in suspension comprising a quinone-based compound expressed by the formula (ring A and ring B are substitutable hydrocarbon ring or substitutable heterocycle having >=1 group selected from hydroxyl group, substitutable amino group and substitutable mercapto group in at least one of the rings A and B).

Description

[Detailed description of the invention] (Industrial application field) The present invention relates to a light control material and a light control element containing the same.

(Prior art and the problem to be solved by the invention) A suspension containing particles that are sensitive to an electric field becomes transparent because the electric field causes the suspended particles to aggregate or align, and in this state, light passes through the suspension, making it transparent. When the electric field is removed, the particles are in a random state and have low light transmission.

Light control elements have been proposed using such properties, and examples of using alkaloid suitability, herapatite, etc. as particles that are sensitive to this electric field are known (
JP-A-53-144895, JP-A-46-4464, etc.).

Light control elements are required to have durability such as ■ light resistance ■ heat resistance ■ water resistance, voltage sensitivity, and response speed.
The above proposal could not be said to have characteristics that could satisfy these requirements.

(Means for Solving the Problems) The present invention solves the above problems, that is,
The present invention provides a light control material which is mainly composed of a suspension medium and a suspension containing particles sensitive to an electric field in the medium, and is capable of changing the light transmittance of the suspension by an electric field. The particles that are sensitive to the electric field contained in the suspension have the following general formula [
The subject matter is a light control material characterized by containing a quinone compound represented by [I] as a main component.

(In the formula, Ring A and Ring B each independently represent an optionally substituted hydrocarbon ring or an optionally substituted heterocycle, and at least one of Ring A or Ring B has one or more It has a group selected from a hydroxyl group, an optionally substituted amino group, and an optionally substituted mercapto group.

) In addition, the gist of the present invention is a light control element characterized in that the light control material is sandwiched between a pair of substrates, at least one of which is transparent and has an electrode on the inner surface. be.

The present invention will be explained in detail below.

Examples of the hydrocarbon ring that may have a substituent in ring A and ring B in the general formula [■] include a benzene ring or a naphthalene ring, and examples of the heterocycle that may have a substituent include: Examples include a pyrrole ring, a furan ring, a thiophene ring, and a pyridine ring.

Substituents for these rings A and B include hydroxyl group;
~18 alkyl group; amino group; -NWA'(A'
is an alkyl group having 1 to 18 carbon atoms which may be substituted with an alkoxy group having 1 to 8 carbon atoms, a cycloalkyl group (for example, a cyclohexyl group which may be substituted with an alkyl group having 1 to 8 carbon atoms, a cyclopentyl group) ), aryl group (
For example, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a phenyl group, biphenyl group, or naphthyl group optionally substituted with a halogen atom such as a chloro atom or a bromine atom), an aralkyl group (a carbon -NHCOA2 (benzyl group or phenethyl group optionally substituted with number 1 to 8 alkyl group or alkoxy group));
A'' is, for example, an alkyl group having 1 to 18 carbon atoms which may be substituted with an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms;
(a cyclohexyl group optionally substituted with an alkyl group, a phenyl group or biphenyl group optionally substituted with an alkyl group having 1 to 8 carbon atoms, or an alkoxy group); a mercapto group, -0A3. -3A3 (A3 has 1 or more carbon atoms
18 alkyl group, cycloalkyl group (e.g. 1 carbon number
cyclohexyl group, cyclopentyl group which may be substituted with ~8 alkyl groups), aryl groups (for example, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 8 carbon atoms, or halogens such as chloro atom, bromine atom, etc.) phenyl group, biphenyl group or naphthyl group which may be substituted with atoms), heterocycle (e.g. pyridine ring or pyrimidine ring which may be substituted with an alkyl group having 1 to 8 carbon atoms)]
; Halogen atoms such as chlorine atom and bromine atom; Aralkyl group (benzyl group or phenethyl group optionally substituted with an alkyl group or alkoxy group having 1 to 8 carbon atoms)
;C0XA"(A" is an alkyl group having 1 to 18 carbon atoms which may be substituted with an alkoxy group having 1 to 8 carbon atoms,
Cycloalkyl group (e.g., cyclohexyl group, decahydro-2-naphthyl group, cyclopentyl group which may be substituted with an alkyl group having 1 to 8 carbon atoms), aryl group (
For example, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a phenyl group, biphenyl group, or naphthyl group which may be substituted with a halogen atom such as a chloro atom or a bromine atom), etc. Examples of X include an oxygen atom, -NH-, and a sulfur atom. ; atom, sulfur atom or =NA'(A' represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms which may be substituted with an alkoxy group having 1 to 8 carbon atoms); Z is an oxygen atom or >N-AS (AS is a hydrogen atom, carbon number 1-
8 an alkyl group optionally substituted with an alkoxy group,
Tetrahydrofurfuryl group, cycloalkyl group (e.g., cyclohexyl group optionally substituted with an alkyl group having 1 to 8 carbon atoms, cyclopentyl group, cyclohexylcyclohexyl group, decahydro-2-naphthyl group), aryl group (carbon number 1 to 8 alkyl groups, alkoxy groups having 1 to 8 carbon atoms, or phenyl groups, biphenyl groups, or naphthyl groups which may be substituted with halogen atoms such as chloro atoms and bromine atoms. ], etc.

Among these quinone compounds, preferred are quinone compounds having a structure represented by the following general formula [■] (wherein, ring A or ring B may each independently have a substituent. , one or more hydroxyl groups on at least one side,
It has an optionally substituted amino group or an optionally substituted mercapto group. ).

Specific examples of the quinone compounds of general formula (I) or (I[) include those in Table 1-1 and Table 1-2 below.

The quinone compound represented by the formula (I) used in the present invention is a substance known as a dye intermediate etc., for example, US Pat. No. 1,108,704, US Pat.
No. 9, Soviet Patent No. 148066, JP-A-57-167
It can be easily synthesized by the method described in No. 952 and the like.

The light control material of the present invention is formed by finely dispersing the quinone compound represented by formula (1) or (II) in a suspending medium such as a solvent that does not dissolve or decompose.

The suspending medium is appropriately selected depending on the type of quinone compound, and examples thereof include aromatic solvents such as benzene, toluene, chlorobenzene, and cyclohexylbenzene; ethyl acetate, di-butyl oxalate, isoamyl benzoate, Ester solvents such as diisodecyl phthalate, ditridecyl phthalate, dioctyl phthalate, phenyl acetate, paracresyl acetate; n-hexane, cyclohexane, n-octane, n-decane, n-dodecane, n-octadecane, bicyclohexyl, decalin Chain or cyclic hydrocarbon solvents such as; halogen solvents such as chloroform, trichloroethane, tetrachloroethane, tetrachlorethylene, tetrabromoethane; n-hexanol, cyclohexanol, 1-octatool, 2
- Alcohol solvents such as decanol; ether solvents such as di-n-butyl ether, diethylene glycol di-n-butyl ether, and dimethoxyethane; ketone solvents such as methyl ethyl ketone, di-n-butyl ketone, and cyclohexanone.

Further, nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, or polymerized versions of these liquid crystals may be used as the dispersion medium, or they may be dispersed in a polymer.

Specific polymers include polyethylene, polyacrylic acid, polymethyl acrylate, polyvinyl acetate, polyacrylonitrile, polyvinyl chloride, polyvinyl fluoride, vinyl compounds and addition polymers of vinyl compounds, polymethacrylic acid, polymethacrylic acid. Methyl, polyethyl methacrylate, polyvinylidene chloride, polyvinylidene fluoride, vinylidene cyanide, vinylidene fluoride/trifluoroethylene copolymer, vinylidene fluoride/tetrafluoroethylene copolymer, vinylidene cyanide/vinyl acetate copolymer Copolymers of vinyl compounds or fluorine compounds, polytrifluoroethylene, polytetrafluoroethylene, etc.
Compounds containing fluorine such as polyhexafluoropropylene,
Polyamide, polyimide, such as nylon 6, nylon 66, etc.
Examples include polyesters such as polyurethane, polypeptide, and polyethylene terephthalate, and polyethers such as polycarbonate, polyoxymethylene, polyethylene oxide, and polypropylene oxide.

These dispersion media may be used alone or in appropriate combinations. Further, the proportion of the quinone compound contained in the dispersion medium may be any proportion as long as it does not cause aggregation or sedimentation, but a range of 0.01 to 10.0% by weight is preferably used. .

A dispersion stabilizer may be added to prevent agglomeration, sedimentation, etc. of the quinone compound.

Examples of dispersion stabilizers include nitrocellulose, polyvinyl butyral, copolymers such as acrylic acid, nonions,
Examples include substances used as dispersion stabilizers for pigments, such as cationic or anionic surfactants.

In addition, the particle size of the finely dispersed suspended particles has a major axis of 100
It is preferable that it is less than μ.

After finely dispersing a quinone compound in a dispersion medium to form a finely dispersed mixture, this mixture is sandwiched between at least a pair of substrates, one of which is transparent and has electrodes on the inner surface, thereby forming a light control element. to make.

A transparent electrode such as ITO is used as the electrode, and a transparent substrate such as a glass or a plastic plate such as polyester is used as the electrode substrate.

When using a pair of transparent electrode substrates, it can be used as a transmission type dimming element, and when using one electrode substrate that is transparent and the other opaque, 1. In this case, a reflective layer is placed after the opaque electrode substrate. By placing it there, it can be used as a reflective light control element.

The light control element according to the present invention can be used in devices that utilize transmission or reflection of light, such as display devices, light control windows, mirrors, sunglasses, and memories.

〔Example〕

EXAMPLES Next, the present invention will be specifically explained with reference to examples, but the present invention is not limited to the following examples.

Example 1 Mixed solvent of diisodecyl phthalate and n-dodecane (mixing ratio 3:2 (vo I/vol)) 3rr+
/! , Surfactant Span 65 (trade name, manufactured by Kao Corporation)
9 mg and 18 mg of a quinone compound represented by the following structural formula were mixed and treated with an ultrasonic device (manufactured by Branson, trade name: Planson B521) for 5 hours to form a suspension to obtain the light control material of the present invention. Ta.

This light control material is used as an ITO transparent electrode (resistance 100Ω) on the inner surface.
A light control element was formed by sealing the light into a glass cell with a cell gap of 11001I.

When no voltage is applied to this element (b: OV) and 100V
FIG. 1 shows the transmittance spectrum of the case (a) when the voltage is applied.

As shown in FIG. 1, when viewed at a wavelength of 700 nm, a change in transmittance of 21% was observed between when 1 oov was applied and when no voltage was applied.

Example 2 3 m of the mixed solvent of Example 1! , 12 mg of surfactant B-261 (trade name, manufactured by IC1) and 18 mg of the quinone compound of Example 1 were mixed, and treated with ultrasound in the same manner as in Example 1 to form a suspension to obtain a light control material. Ta.

This light control material was sealed in a cell similar to that in Example 1 to form a light control element.

The transmission spectrum of this material is shown in Figure 2 (a: voltage 1
When 00V is applied, b: When no voltage is applied). When the measurement was performed three times, the spectra were almost the same in each case, indicating good repeatability.

Furthermore, as shown in Fig. 2, this device has a wavelength of 400 nm to 800 nm.
Over the nm range, the transmittance showed a change of about 37% between when 100V was applied and when no voltage was applied.

Example 3 Di-n-octyl phthalate and diethylene glycol di-
Mixed solvent of n-butyl ether (mixing ratio 2:1 (vo
l/vol))3mI! ,, 9 mg of the surfactant used in Example 2 and 18 mg of the quinone compound of Example 1 were mixed to form a suspension in the same manner as in Example 1 to obtain a light control material.

This light control material was sealed in a cell similar to that in Example 1 to form a light control element.

When no voltage is applied to this element (b: OV) and 100v
FIG. 3 shows the transmission spectrum in case (a) when the voltage is applied.

In this case, no voltage application (0■) and voltage application (100V) were repeated five times, but the same spectrum was obtained, and the repetition characteristics were good.

Furthermore, as shown in Figure 3, when viewed at a wavelength of 700 nm, 1
The transmittance showed a change of 26% between when 00■ was applied and when no voltage was applied.

Example 4 The mixed solvent used in Example 1 was 2mi! , 12 mg of the surfactant used in Example 2 showed the following structural formula weighting.

Example 5 Mixed solvent of diisodecyl phthalate and n-dodecane (mixing ratio 1:9 (vol/vo 1)) 1.5 m/!
, 4.5 mg of the surfactant used in Example 2, and 12 mg of the quinone compound represented by the following structural formula were mixed, and treated with ultrasonic waves in the same manner as in Example 1 to form a suspension. I got it.

This light control material was sealed in a cell similar to that in Example 1 to form a light control element.

When no voltage is applied to this element (b: OV) and 100V
FIG. 4 shows the transmission spectrum in case (a) when the voltage is applied.

Furthermore, as shown in Figure 4, when viewed at a wavelength of 600 nm, 1
9 mg of a quinone-based compound having a transmission of 24% when 00■ was applied and when no voltage was applied was mixed and subjected to ultrasonic treatment in the same manner as in Example 1 to stop the suspension, thereby obtaining a light control material.

This light control material was sealed in a cell similar to that in Example 1 to form a light control element.

When no voltage is applied to this element (tzOV) and 100■
FIG. 5 shows the transmission spectrum in case (a) when the voltage is applied.

Furthermore, as shown in Figure 5, when viewed at a wavelength of <650 nm, 10
The transmittance showed a change of 44% between when 0V was applied and when no voltage was applied.

Examples 6 to 15 A light control material containing a quinone-based compound was formed in the same manner as in Example 1, a light control element was created using the same, and changes in transmittance were measured when 100 V was applied and when no voltage was applied. The result is the second
Shown in the table.

Table *1 Mixing ratio (vol/vol) in case of mixed solvent *2
B261...Product name: B246 manufactured by IC1...
・Product name: Epan 420 manufactured by ICI...Product name: Diskol 202 manufactured by Daiichi Kogyo Seiyaku Co., Ltd.Product name: Made by Daiichi Kogyo Seiyaku *3 Transmission at 650 nm with and without application of 100V Rate change (%) (Effect of the invention) The light control material obtained by the present invention has light resistance, heat resistance,
It has good water resistance, and light control elements using the light control material are useful for display devices, light control windows, memories, and the like.

[Brief explanation of drawings]

Figures 1.2, 3, and 4.5 are Example 1゜2.3, respectively.
FIG. 4.5 is a diagram showing the electric field response of the light control element of the present invention obtained in Section 4.5. In each figure, the horizontal axis is wavelength (nm)
, the vertical axis represents the transmittance (%), a represents the transmittance when 100 cm is applied, and b represents the transmittance when no voltage is applied (Ov).

Claims (2)

[Claims] (1) A light control material that is mainly composed of a suspension medium and a suspension containing particles sensitive to an electric field in the medium, and is capable of changing the light transmittance of the suspension by an electric field. Particles contained in a liquid that are sensitive to an electric field have the following general formula [
A light control material characterized by containing a quinone compound represented by [I] as a main component. ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, Ring A and Ring B each independently represent an optionally substituted hydrocarbon ring or an optionally substituted heterocycle) and at least one of Ring A or Ring B has a group selected from one or more hydroxyl groups, optionally substituted amino groups, and optionally substituted mercapto groups.) (2) A light control element characterized in that the light control material according to claim (1) is sandwiched between a pair of substrates, at least one of which is transparent and has an electrode on its inner surface.