JP2002179672A - New compound and optical element produced by using the compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compound capable of forming an amorphous thin film, achieving high density of a photoreactive group and getting high conversion of photoreaction, and a photochromic material produced by using the compound. SOLUTION: The compound is expressed by the formula (R1 is H, methyl, ethyl, methoxy, i-propyl or t-propyl; R2 is H, a 1-20C straight or branched alkyl or an aryl; R3 is an arbitrary substituent having a conjugable unsaturated bond; and X is a halogen such as F, Cl, Br and I).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel compound and a method for synthesizing the same, and more particularly, to a compound which can be used for a photochromic material and a method for synthesizing the same.

[0002]

2. Description of the Related Art In display, optical recording, and switching element materials utilizing photochromism, the absorption spectrum reversibly changes with light irradiation, and the absorption spectrum changes (absorbance and absorption band wavelength region) are large. thing,
It is required to have high sensitivity, a high rate of change of the absorption spectrum, excellent repetition stability, high stability of the photoreaction product in a dark place, and the like. In particular,
In order to increase the change in the absorption spectrum due to light irradiation as much as possible, it is necessary to increase the concentration of the photoreactive group exhibiting photochromism as much as possible and to increase the conversion rate of the reaction and the reaction efficiency during light irradiation. Furthermore, in the display device, the absorption spectrum changes in the visible region (400 to 700 nm), the quantum yield of the coloring reaction is large so as to improve the writing speed, and the display is performed under visible light of normal intensity. It is required that the quantum yield of the erasure reaction be small so that does not disappear. Further, it is necessary that light is not scattered and that a thin film can be formed. Therefore, it is desired that the material used for such an element can form a uniform amorphous thin film.

[0003] Conventionally, from the viewpoint of the ability to form an amorphous thin film, as a material for a display, an optical recording medium, and an optical switching element utilizing photochromism, a polymer material or a polymer composite in which a low-molecular photochromic compound is dispersed in a polymer is used. Materials are known.

[0004]

However, in the above-mentioned polymer material or polymer composite material, the concentration of the photoreactive group cannot be 100%. Because, in the case of a polymer material, there is a polymer main chain, and in the case of a polymer composite material, there is a polymer binder, and these polymer main chain and polymer binder are components unrelated to the photoreactive group. Therefore, in these systems, it is impossible to increase the concentration of the photoreactive group to 100%.

Further, in the case of the polymer composite material, the compatibility between the dispersed low-molecular organic compound and the polymer causes a problem that the dispersed low-molecular organic compound and the polymer are phase-separated and crystallized. cause. Therefore, the display using photochromism, which can increase the density of the photoreactive group, does not cause phase separation, and can achieve high conversion and reaction efficiency,
It is desirable to develop materials for optical recording and optical switching elements.
However, such materials have not been previously known.

Therefore, an object of the present invention is to provide a compound capable of forming a thin film, achieving a high density of photoreactive groups and a high conversion rate of photoreaction, and a photochromic material using the compound. To provide.

[0007]

Means for Solving the Problems In order to achieve the above object, the present inventors have made intensive studies and have found a compound capable of forming an amorphous thin film using only a low molecular weight organic compound.

The compound of the present invention has the following general formula:

Embedded image (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² represents hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms. ,
Or an aryl group, and R ³ represents an arbitrary substituent having a conjugateable unsaturated bond. X represents a halogen such as F, Cl, Br and I. ).

In a preferred embodiment of the compound of the present invention, R ³ is

Embedded image In represented by (wherein, R ¹ is hydrogen, a methyl group, an ethyl group,
Methoxy, i- propyl group, a t- butyl group, R ⁴
Represents an aromatic hydrocarbon or a heterocyclic aromatic substituent such as a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, a diphenylaminophenyl group, an indolyl group, and a furyl group. Z represents one of sulfur, oxygen and hydrogen or nitrogen to which an alkyl group is bonded. ).

In a preferred embodiment of the compound of the present invention, a compound represented by the general formula:

Embedded image Wherein R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ⁴ represents a linear or branched alkyl having 1 to 10 carbon atoms. Represents an aromatic hydrocarbon or a heterocyclic aromatic substituent such as a phenyl group, a diphenylaminophenyl group, an indolyl group, a furyl group, etc. Z is any one of sulfur, oxygen and hydrogen or nitrogen bonded to an alkyl group. Show one: X
Represents a halogen such as F, Cl, Br and I. ).

In a preferred embodiment of the compound of the present invention, R ³ is represented by the following formula:

Embedded image (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² represents hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms. ,
Or an aryl group. X represents a halogen such as F, Cl, Br and I. ).

In a preferred embodiment of the compound of the present invention, a compound represented by the general formula:

Embedded image (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² represents hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms. Or an aryl group. X represents a halogen such as F, Cl, Br, and I).

In a preferred embodiment of the compound of the present invention, R ¹ is a methyl group.

In a preferred embodiment of the compound of the present invention, the quantum yield of the ring-opening reaction upon light irradiation is as follows:
It is characterized by being 0.01 or less.

[0015] In a preferred embodiment of the compound of the present invention, the quantum yield of the photocyclization reaction in a solution is 0.5.
It is characterized by being 5 or more. The optical element of the present invention is characterized by using the compound.

In a preferred embodiment of the optical element of the present invention, the ring formed by thiophene and cyclopentene of the compound opens and closes upon irradiation with light to exhibit photochromism.

Further, in a preferred embodiment of the optical element of the present invention, the conversion of the ring closure reaction upon irradiation with light is:
It is characterized by being 50% or more.

The method for synthesizing the compound of the present invention is as follows.

Embedded image (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² is hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms. X represents a halogen such as F, Cl, Br and I), and is reacted with an alkyl lithium to react a reaction product with a halogenated cyclopentene. Done,

Embedded image Wherein the compound of the formula (1) is synthesized.

[0019]

BEST MODE FOR CARRYING OUT THE INVENTION

Embedded image The compound of the present invention represented by the above [Formula 16] (provided that R
¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group; R ² represents hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms;
³ represents an arbitrary substituent having a conjugated unsaturated bond. X represents a halogen such as F, Cl, Br and I. )

Embedded image Wherein R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² represents hydrogen or a straight chain having 1 to 20 carbon atoms. X represents F, Cl, Br and
Shows halogen such as I. ) In a solution of ethers (such as tetrahydrofuran and diethyl ether), alkyl lithium (e.g., methyl lithium, ethyl lithium, n-propyl lithium, i-propyl lithium,
n-butyllithium, s-butyllithium, t-butyllithium, etc.)

Embedded image And a halogenated cyclopentene represented by the following formula: The reaction formula is as follows.

[0020]

Embedded image In Chemical Formula 19, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² is hydrogen, a linear or branched C 1-20 carbon atom. Shows a substituent selected from an alkyl group and an aryl group. R
² is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group which is a linear or branched alkyl group having 1 to 4 carbon atoms, or a phenyl group, a tolyl group, or a naphthyl group which is an aromatic substituent. And so on. R ³ represents an aromatic hydrocarbon or a heterocyclic aromatic such as a phenyl group, a thienyl group, a furyl group, an indolyl group, and is preferably a thienyl group. R ³ is more preferably represented by the following formula:
0].

[0021]

Embedded image (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ⁴ represents a linear or branched alkyl group having 1 to 10 carbon atoms or a phenyl group. Represents an aromatic hydrocarbon or a heterocyclic aromatic substituent such as a diphenylaminophenyl group, an indolyl group, or a furyl group, and Z represents one of sulfur, oxygen, and nitrogen bonded to hydrogen or an alkyl group. .)

R ³ is more preferably represented by the following formula:
It is shown in.

Embedded image (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ⁴ represents a linear or branched alkyl group having 1 to 10 carbon atoms or a phenyl group. Represents an aromatic hydrocarbon or a heterocyclic aromatic substituent such as a diphenylaminophenyl group, an indolyl group, or a furyl group, and Z represents one of sulfur, oxygen, and nitrogen bonded to hydrogen or an alkyl group. ) Further, X represents a halogen such as F, Cl, Br, I, and the like, and X is preferably F from the viewpoint of electronegativity.

In particular,

Embedded image The reaction formula for synthesizing the compound of the formula is as follows.

Embedded image

Also,

Embedded image The reaction formula for synthesizing the compound of the formula is as follows.

Embedded image

In the present invention, even a low molecular weight organic compound has a non-planar triphenylamine skeleton, whereby crystallization is suppressed and an amorphous thin film can be formed.

That is, generally, the low molecular weight organic compound is
Although it has high crystallinity and exists as crystals below the melting point, in the present invention, such crystallization can be prevented and a good amorphous thin film can be formed.

The photochromic properties of the compound according to the present invention will be described below.

Embedded image

That is, the portion formed by thiophene, cyclopentene, and an aromatic hydrocarbon or a heterocyclic aromatic substituent is a photoreactive group exhibiting photochromism. The compound according to the present invention and the photochromic material using the compound change the absorption spectrum of the compound by irradiating the photoreactive group with light, and exhibit photochromic properties. This is because a ring formed by thiophene, cyclopentene, and an aromatic hydrocarbon or a heteroaromatic substituent is opened and closed at the time of light irradiation. A reaction in which a ring formed by thiophene, cyclopentene, and an aromatic hydrocarbon or a heterocyclic aromatic substituent is changed from an open state to a closed state is defined as a photoring-closing reaction or simply a ring-closing reaction. On the other hand, thiophene, cyclopentene, and aromatic hydrocarbon or heterocyclic aromatic substituent or a ring formed by a reaction from a closed state to an open state, a photo ring opening reaction,
It is simply defined as a ring opening reaction. In the present invention, in order to cause a ring-closing reaction of the photoreactive group, the wavelength of light applied to the photoreactive group is
Although it depends on the type of the compound, the thickness is set to 250 to 400 nm. Preferably, it is 365 nm. On the other hand, in order to cause a ring-opening reaction of the photoreactive group, the wavelength of light applied to the photoreactive group is 580 nm or more, although it depends on the type of the compound. Preferably, the thickness is 600 nm or more. From the viewpoint of using the wavelength of visible light, the upper limit is 76
It is about 0 to 830 nm. In the compound of the present invention, the quantum yield of the photo-ring-opening reaction upon light irradiation can be 0.01 or less. Preferably, it can be 0.005 or less. When a compound having such a quantum yield is used for an optical element such as a display element, it has an effect of making it difficult to erase displayed characters and the like. Therefore, according to the present invention, by appropriately selecting a compound having a small quantum yield of the photo-ring-opening reaction and using the compound for the display device, a display device in which the display state of characters and the like is always good can be achieved. Also,
In the compound of the present invention, the quantum yield of the photocyclization reaction in a solution can be 0.5 or more. When a compound having such a quantum yield is used for an optical element such as a display element, writing speed of characters to be displayed can be increased. Therefore, according to the present invention, a display element in which writing of characters and the like can be performed quickly can be achieved by appropriately selecting a compound having a large quantum yield of the photocyclization reaction. Further, according to the optical element using the compound of the present invention, the conversion of the ring-closing reaction during light irradiation can be 50% or more. Preferably, it is at least 60%. When the conversion of the ring closure reaction is high, there is an advantage that the change in absorption spectrum can be increased.

Further, according to the optical element using the compound of the present invention, the quantum yield of the ring-opening reaction at the time of light irradiation is 0.1%.
01 or less. Preferably, it can be 0.005 or less.

Next, a method for producing an optical element using the compound of the present invention will be described. The optical element can be manufactured by an ordinary method. For example, a thin film can be formed from a benzene solution containing a compound on a substrate by a spin coating method or the like. The spin coating method is one of the methods for producing a solid polymer film,
In this method, a compound is dissolved in a solvent, the solution is dropped at the center of a rotating substrate, and the solvent is evaporated to form a film on the substrate.

As other thin film forming methods, there can be mentioned a PVD method such as a vacuum evaporation method, a CVD method and the like.

The thickness of the photochromic material thus formed is from 20 to 200 nm, preferably from 50 to 100 nm, so as to exhibit an absorbance capable of better exhibiting photochromic properties.

[0033]

Here, one embodiment of the present invention will be described. However, the present invention is not construed as being limited to the following embodiment. Further, the present invention can be appropriately modified and implemented without departing from the spirit of the present invention.

Hereinafter, among the compounds represented by Chemical Formula 4,

Embedded image Among the compounds represented by the following formula:

Embedded image And a compound represented by the following formula:

Embedded image The following is an example of a compound.

Example 1 A photochromic material represented by the following chemical formula: 1,2-bis (5- {4- [N, N-bis (4-methylphenyl) amino] phenyl} -2-methylthiophen-3 -Yl) -3,3,4,4,5,5-hexafluorocyclopentene is synthesized as follows. 5- {4- [bis (4-methylphenyl) amino] phenyl}
Add a tetrahydrofuran solution containing 5.40 g (0.012 mol) of -3-bromo-2-methylthiophene, and stir at -78 ° C.
11.5 ml (0.018 mol) of 1.6N n-butyllithium was added dropwise,
Stir for 1 hour. Next, octafluorocyclopentene
1.25 ml (0.009 mol) was added, and the mixture was stirred for about 24 hours. After completion of the stirring, water was added, and the mixture was extracted with diethyl ether. Then, the organic layer was washed with 0.1N hydrochloric acid and water. After evaporating the solvent, a compound [Chemical Formula 27] was obtained by silica gel chromatography using a mixed solvent of toluene and hexane as a developing solvent, and recrystallization from a mixed solvent of hexane and toluene. The yield was 2.5 g and the yield was 45%. The physical properties are shown below. Melting point: 207 ° C. Mass spec: m / e = 911 (M ⁺ ) ¹ H NMR (benzene-d ₆ , 600 MHz): δ (pp
m) = 2.09 (s, 6H), 2.97 (s, 12
H), 6.67 (s, 2H), 6.89 (d, 4H, J
= 8.9 Hz), 6.91 (d, 8H, J = 8.2H)
z), 7.02 (d, 8H, J = 8.2 Hz), 7.1
2 (d, 4H, J = 8.9 Hz) Infrared absorption spectrum (KBr, cm ^-1 ): 3100 (aromatic CH
Stretch), 2920 (aliphatic CH stretch), 1600 (C = C ring stretch), 1520 (C = C ring stretch thiophene ring), 132
0 (aromatic tertiary amine CN stretch), 1280 (aromatic tertiary amine CN)
Tertiary amine CN stretch), 820 (1,4-disubstituted benzene), 720 (2,3,5-trisubstituted thiophene CH out-of-plane bending angle) UV-visible absorption spectrum (benzene): 304, 362
nm Elemental analysis _{(C 55 H 44 N 2 S} 2) theory: C, 72.28; H, 4.94 ; N, 2.95
% Found: C, 72.51; H, 4.87; N, 3.07.
%

Example 2 A photochromic material represented by the following chemical formula: 1- (5- ｛4-
[Bis (4-methylphenyl) amino] phenyl} -2-methylthiophen-3-yl) -2- (2-methyl-1-benzothiophene
The synthesis of -3-yl) perfluorocyclopentene is as follows. 3.5 g (0.0078 mol) of 5- {4- [bis (4-methylphenyl) amino] phenyl} -3-bromo-methylthiophene
Is cooled to −78 ° C. and 1.6N n-BuLi 6 ml
(0.096 mol) was added dropwise, and the mixture was stirred for about 1 hour. Next, 1- (2-
A solution of 3.0 ml (0.088 mol) of methyl-1-benzothiophen-3-yl) perfluorocyclopentene in 30 ml of THF was added dropwise, and the mixture was stirred for about 24 hours. After stirring, 0.1NH
After adding Cl to stop the reaction, the mixture was washed with water. After evaporating the solvent,
The resultant was separated by silica gel chromatography (developing solvent: hexane), and recrystallized from EtOH / THF to obtain a pale yellow solid compound [Formula 28]. The yield was 1.8 g, and the yield was 33%. Melting point: 158 ° C. Mass spec: m / e = 689 (M ⁺ ) ¹ H NMR (benzene-d ₆ , 600 MHz): δ (pp
m) = 1.65 (s, 3H), 1.97 (s, 3H),
2.10 (s, 6H), 6.91 (d, 4H, J = 8.
3 Hz), 6.92 (t, 1H, J = 8.0 Hz),
7.00 (d, 2H, J = 8.9 Hz), 7.05
(T, 1H, J = 8.0 Hz), 7.05 (d, 4H,
J = 8.3 Hz), 7.15 (d, 2H, J = 8.9H)
z), 7.18 (s, 1H), 7.30 (d, 1H, J
= 8.0 Hz), 7.64 (d, 1H, J = 8.0 Hz) Infrared absorption spectrum (KBr, cm ^-1 ): 3000 (aromatic CH
Stretch), 2910 (aliphatic CH stretch), 1600 (C = C ring stretch), 1520 (C = C ring stretch thiophene ring), 132
0 (aromatic tertiary amine CN stretch), 1270 (aromatic tertiary amine CN)
Tertiary amine CN stretching), 830 (1,4-disubstituted benzene), 730 (2,3,5-trisubstituted thiophene CH out-of-plane bending) UV-visible absorption spectrum (benzene): 302, 357
nm Elemental analysis _{(C 39 H 29 NF 6 S} 2) theory: C, 67.83; H, 4.26 ; N, 2.04
% Found: C, 67.91; H, 4.24; N, 2.03.
%

Example 3 FIG. 1 shows an example of a device using the compound of the present invention. On a glass substrate, place a benzene solution of the compound (6.6 × 10 ^-3 mol d
m ^-3 ) by spin coating method, about 75 nm in film thickness, about 3 c in area
An amorphous thin film of m ² was formed. The thickness of the photochromic material is 50 nm or more, 100
nm or less.

The ring-opening and ring-closing reactions were carried out using an ultra-high pressure mercury lamp.
5 nm light (1.6 mW / cm ² ) and 580 from xenon lamp
The irradiation was performed by irradiating light (9 mW / cm ² ) having a wavelength of nm or more. As a result of differential scanning calorimetry, it was found that Compound [Chemical Formula 27] and Compound [Chemical Formula 28] had high glass transition temperatures (94 ° C. and 66 ° C., respectively). Further, it was found that the amorphous thin film of the compound was stable and did not cause crystallization for a long period of time.

Hereinafter, the change in the absorption spectrum of the amorphous thin film was examined using the compound [Chemical Formula 27] as an example. FIG. 2 shows the measurement results of the absorption spectrum of the amorphous thin film of the compound [Chemical Formula 27]. By irradiating the amorphous thin film of the compound [Formula 27] with light of 365 nm,
In about 10 seconds, the absorption spectrum changed from the spectrum 4 to the spectrum 5, and reached the photo-steady state. Along with that, the color changed from light yellow to green. This is based on the fact that the structure of the compound [Chemical Formula 27] changes from a ring-opened form to a closed-ring form with light irradiation as shown in the following formula. This structural change was reversible, and the closed form returned to the open form upon irradiation with light at 600 nm, and the absorption spectrum recovered to about 95% of the spectrum before irradiation with 365 nm light in about 9 minutes. The ring-closed form of the compound [Chemical Formula 27] was extremely stable thermally in the dark, and even when heated to 80 ° C., no change in the absorption spectrum due to the formation of the ring-opened form was observed.

Example 4 A compound of the formulas [Chemical Formulas 27 and 29] was synthesized using the same method as in the above-mentioned Example, and the conversion of the compound in a ring closure reaction upon irradiation with light in an amorphous thin film was examined. The results are shown in the following equation.

Embedded image

Embedded image

As a result, the conversion of the photocyclization reaction of [Chemical Formula 27] having two triphenylamine skeletons was as high as 0.77, and the conversion of the photocyclization reaction of [Chemical Formula 29] was as follows. Was 0.67. Achieving high conversion results in large absorbance changes and large changes in physical properties.

Example 5 Next, among the compounds of the present invention, [Chemical Formula 27], [Chemical Formula 28], and
The quantum yield of the ring-opening reaction associated with visible light irradiation after photocyclization was examined for the compound of the formula [Formula 29].

Embedded image

Embedded image

Embedded image

As a result, the quantum yields of the reactions of [Formula 32] and [Formula 34] were extremely low, 0.001 and 0.01 for the reaction of [Formula 33]. By using a material having a low ring-opening reaction quantum yield for a display element, a stable image that was not erased under visible light of normal intensity was obtained.

Example 6 The quantum yield of the photocyclization reaction of the compounds represented by the formulas [Chemical Formula 27] and [Chemical Formula 28] synthesized in Examples 1 and 2 in a benzene solution was measured by using 365 nm light from an ultra-high pressure mercury lamp. It was determined from the change in the absorption spectrum of the solution upon irradiation.

Embedded image

Embedded image

As a result, the quantum yield of the photocyclization reaction of [Formula 35] was 0.61, and the quantum yield of the photocyclization reaction of [Formula 36] was 0.79.
Showed a large value. A display element with a high writing speed can be obtained by applying a compound having a large quantum yield of the photocyclization reaction to the display element.

[0046]

According to the compounds and / or materials of the present invention, the density of photoreactive groups can be increased, and further, there is an advantageous effect that the problem of phase separation does not occur.

According to the compounds and / or materials of the present invention,
Even with a low molecular weight organic compound, it is possible to form an amorphous thin film, which is stable and has an advantageous effect that crystallization does not occur for a long period of time.

Further, according to the compound and / or material of the present invention, there is an advantageous effect that the compound is extremely stable thermally and is reversible and exhibits a photoreaction with a large conversion.

[Brief description of the drawings]

FIG. 1 is a side view of a device showing an example of a device configuration manufactured using a compound of the present invention.

FIG. 2 is a diagram showing an example of an absorption spectrum of a device manufactured using the compound of the present invention.

[Explanation of symbols]

Reference Signs List 1 glass substrate 2 photoreactive amorphous film 3 display / optical recording / optical switching element 4 absorption spectrum before irradiation with 365 nm light 5 absorption spectrum in steady state of light (365 nm light (1.6 m
W / cm ² )

Claims (14)

[Claims] 1. A compound of the general formula (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² represents hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms. Or an aryl group, R ³ represents an arbitrary substituent having a conjugateable unsaturated bond, and X represents a halogen such as F, Cl, Br, and I). (2) R ³ is represented by the following formula: (Where R ¹ is hydrogen, a methyl group, an ethyl group,
Methoxy, i- propyl group, a t- butyl group, R ⁴
Represents an aromatic hydrocarbon or a heterocyclic aromatic substituent such as a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, a diphenylaminophenyl group, an indolyl group, and a furyl group. Z represents one of sulfur, oxygen, and hydrogen or nitrogen to which an alkyl group is bonded. 2. The compound according to claim 1, wherein: (3) R ³ is a compound represented by the following formula: (Where R ¹ is hydrogen, a methyl group, an ethyl group,
Methoxy, i- propyl group, a t- butyl group, R ⁴
Represents an aromatic hydrocarbon or a heterocyclic aromatic substituent such as a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, a diphenylaminophenyl group, an indolyl group, and a furyl group. Z represents one of sulfur, oxygen, and hydrogen or nitrogen to which an alkyl group is bonded. 2. The compound according to claim 1, wherein: 4. A compound represented by the general formula: (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² represents hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms. Or X represents an aryl group, and X represents a halogen such as F, Cl, Br, and I). 5. A compound of the general formula: (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² represents hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms. Or an aryl group. X represents a halogen such as F, Cl, Br, and I). 6. The compound according to claim 1, wherein R ¹ is a methyl group. 7. The quantum yield of the photo-ring-opening reaction upon light irradiation is
The compound according to any one of claims 1 to 6, which is 0.01 or less. 8. The photocatalytic ring closure reaction in solution has a quantum yield of 0.5.
The compound according to claim 1, wherein the number is 5 or more. 9. An optical element using the compound according to claim 1. 10. The compound according to claim 9, wherein a ring formed by thiophene, cyclopentene and an aromatic hydrocarbon or a heterocyclic aromatic substituent of the compound opens and closes upon irradiation with light to exhibit photochromism.
An optical element as described. 11. The conversion of a ring closure reaction upon irradiation with light is:
The optical element according to claim 9 or 10, wherein the content is 50% or more. [Claim 12] (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ² is hydrogen or a linear or branched alkyl group having 1 to 20 carbon atoms. X represents a halogen such as F, Cl, Br, and I), and the reaction product is reacted with an alkyllithium to react a reaction product with a halogenated cyclopentene. Composed of the process A method for synthesizing the compound of 13. The method according to claim 13, wherein the alkyl lithium is methyl lithium,
Ethyl lithium, n-propyl lithium, i-propyl lithium, n-butyl lithium, s-butyl lithium, t
At least one selected from the group selected from butyl lithium
13. The method according to claim 12, which is one kind. 14. The method according to claim 12, wherein the halogenated cyclopentene is composed of any one of a group of compounds represented by the following formula. Embedded image (However, R ¹ represents hydrogen, a methyl group, an ethyl group, a methoxy group, an i-propyl group, a t-butyl group, and R ⁴ represents a linear or branched alkyl group having 1 to 10 carbon atoms or a phenyl group. , An aromatic hydrocarbon or a heterocyclic aromatic substituent such as a diphenylaminophenyl group, an indolyl group, and a furyl group. X represents a halogen such as F, Cl, Br, and I.)