CN116390961A

CN116390961A - Polymer dispersed liquid crystal composition, liquid crystal element, and light adjusting element

Info

Publication number: CN116390961A
Application number: CN202180074950.7A
Authority: CN
Inventors: 中田秀俊; 高岛正直
Original assignee: DIC Corp
Current assignee: DIC Corp
Priority date: 2020-12-25
Filing date: 2021-12-16
Publication date: 2023-07-04
Also published as: JPWO2022138418A1; TW202229524A; KR20230122577A; WO2022138418A1; JP7276619B2

Abstract

The invention provides a polymer dispersed liquid crystal composition, a liquid crystal element and a light adjusting element, which have strong adhesion with a base material, high reliability, good heat resistance, especially little decrease of transmittance after heating and high transparency when voltage is on. The polymer dispersed liquid crystal composition contains a polymerizable compound (MA) and a non-polymerizable liquid crystal compound (LB). The polymerizable compound (MA) contains one or more cyclic monofunctional polymerizable compounds as a first component. The non-polymerizable liquid crystal compound (LB) contains one or more diphenylacetylene compounds as a second component.

Description

Polymer dispersed liquid crystal composition, liquid crystal element, and light adjusting element

Technical Field

The present invention relates to a polymer dispersed liquid crystal composition, a liquid crystal element obtained using the polymer dispersed liquid crystal composition, and a light control element using the liquid crystal element. The light modulation element comprises: dimming elements used in Smart Windows (SW), window glass, doors, partitions (sections), private glass (private glass) and the like of buildings such as houses or buildings; dimming elements used in glass windows, mirrors, roofs, etc. used in transportation media such as automobiles, airplanes, ships, electric trains, etc.; light control elements used for light control of digital cameras, smart phones, etc., light scattering plates for light sources for displays, light guiding plates, reflection plates for reflective displays, transparent displays, etc.

Background

A polymer dispersed (PNM) liquid crystal element in which a liquid crystal material is dispersed in a polymer matrix or a polymer dispersed liquid crystal element in which a liquid crystal material is present in a polymer network is different from a general liquid crystal element in that the degree of transmission/scattering of the element can be adjusted. According to the above feature, the present invention can be expected to be applied to a high-value display such as a reflective display, a transparent display, a local dimming (local dimming) light diffusion element, and a variable reflective element. On the other hand, regarding applications in window Glass for building materials or transportation, interior decoration, exterior appearance (exterior), personal Glass (Straight Glass (SG)), smart Glass for variable projector screens, digital signage, or the like, or Smart Window (SW), etc., which flexibly utilize a light-adjusting function of transmission/scattering, a light-adjusting material for realizing the applications is desired because a mobile terminal is used with the development of communication technology in recent years and control of various equipment and machines can be realized both for industrial use and for home use.

In particular, when the glass or window (SW) is spread, the entire surface of the polymer dispersed liquid crystal element or the entire surface of the polymer dispersed liquid crystal element is dimmed, and therefore, in general, a voltage is applied to the entire surface with a simple structure such as a transparent substrate, a transparent electrode layer, the liquid crystal element layer, a transparent electrode layer, and a transparent substrate layer. In the case of using the transparent window, high scattering property is required to mask the other side, and high transparency is required in a transparent state, which is not so high. Further, these states can be electrically switched, but power saving is required, and a low driving voltage of ON (ON) and OFF (OFF) switching voltages is desired. In addition, from the viewpoint of productivity, it is important that the film be directly formed on a flexible substrate such as a polyethylene terephthalate (Polyethylene Terephthalate, PET) film or a Polycarbonate (PC) film by a roll-to-roll method. In order to produce the liquid crystal element by the roll-to-roll method, the adhesion (adhesion) between the substrate and the liquid crystal element is also an important characteristic, and high adhesion to the substrate is also required. Further, smart windows and the like are sometimes used outdoors and the like, and therefore high light resistance and high heat resistance are also required.

Patent document 1 discloses an example of low-voltage driving using a specific monomer compound, but has a problem of insufficient adhesion. In patent document 2, a specific liquid crystal compound is used to improve light resistance, and a certain effect is observed in light resistance, but there is a problem that light scattering property is insufficient. Patent document 3 discloses that a specific polymerizable compound is used to improve adhesion, and that the adhesion has a certain effect, but has a problem of high driving voltage. As described above, a method for improving scattering property, driving voltage, and adhesion with good balance is demanded.

Prior art literature

Patent literature

Patent document 1: japanese patent laid-open No. 6-208107

Patent document 2: japanese patent laid-open No. 2007-91850

Patent document 3: japanese patent laid-open publication No. 2011-026526

Disclosure of Invention

Problems to be solved by the invention

In consideration of productivity as described in the prior art, when the flexible substrate is used for production, good adhesion to the transparent substrate or the transparent electrode layer and the liquid crystal element layer is required in each step to such an extent that the transparent substrate or the transparent electrode layer does not separate from the liquid crystal element layer. In addition, in consideration of workability and processability, adhesion is also required. Further, as the light control element, characteristics such as reliability, heat resistance, transmittance after heating, and transparency when voltage is turned on, which are durable to practical use, are required.

Accordingly, an object of the present invention is to provide a polymer-dispersed liquid crystal composition, a liquid crystal element, and a light control element, which have excellent adhesion to a driving voltage, high reliability, good heat resistance, and particularly, little decrease in transmittance after heating, and high transparency when the voltage is turned on.

Technical means for solving the problems

The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have found that a polymer-dispersed liquid crystal composition, a liquid crystal element, and a light control element, which are excellent in adhesion to a driving voltage, high in reliability, good in heat resistance, and particularly, less in decrease in transmittance after heating and high in transparency when voltage is turned on, can be obtained, and have completed the present invention.

Namely, the present invention provides a polymer dispersed liquid crystal composition,

which contains a polymerizable compound (MA) and a non-polymerizable liquid crystal compound (LB), wherein in the polymer dispersed liquid crystal composition,

the polymerizable compound (MA) contains one or more cyclic monofunctional polymerizable compounds represented by the following general formula (ii) as a first component,

[ chemical 1]

P ⁱⁱⁱ¹ -Z ⁱⁱⁱ¹ -A ⁱⁱⁱ¹ (ii)

(wherein P ⁱⁱⁱ¹ Represents a functional group having a polymerizable property,

Z ⁱⁱⁱ¹ represents a single bond or an alkylene group having 1 to 7 carbon atoms, one or more of which are not adjacent to each other-CH ₂ -independently of each other through-O-, in such a way that the oxygen atoms are not directly adjacent-CO-, -COO-or-OCO-substitution,

A ⁱⁱⁱ¹ represents general formula (ii-1) to general formula (ii-20),

[ chemical 2]

(wherein, more than one-CH ₂ -can be independently passed through-O-, -S-, -COO-, -OCO-, -NH-, -NCH ₃ -or-CO-substitution, wherein in the case where two or more oxygen atoms and/or sulfur atoms are present in total in the general formulae (ii-1) to (ii-20), these are not bonded to each other as in-O-O-, -O-S-or-S-S-, and in addition, one or more-CH ₂ -CH ₂ -may be substituted with-ch=ch-group, and in addition, the hydrogen atom in the general formulae (ii-1) to (ii-20) may be substituted with an alkyl group having 1 to 8 carbon atoms, one or more of the alkyl groups being not adjacent-CH ₂ -each independently substituted by-O-, -CO-, -COO-, or-OCO-in such a way that the oxygen atoms are not directly adjacent. In addition, the black dots in the formula represent the direction Z ⁱⁱⁱ¹ Bond) of (c))

The non-polymerizable liquid crystal compound (LB) contains one or more of the tolan (tolan) compounds represented by the following general formula (iii) as a second component.

[ chemical 3]

(wherein R is ¹¹ Independently of one another, is an n-alkyl, n-alkoxy, alkenyl, alkenyloxy or alkoxyalkyl radical having from 1 to 7 carbon atoms,

R ¹² Represents fluorine atom, chlorine atom, cyano group, CF ₃ Radical, OCF ₃ Radical, OCHF ₂ A group, NCS group or C1-10 alkyl group, one or both of which are not adjacent CH ₂ The group may be substituted with an oxygen atom, -COO-, -OCO-, and in addition, one or more methylene groups may be substituted with-CH=CH-or-C≡C-, preferably a fluorine atom, a cyano group or an alkyl group having 1 to 5 carbon atoms (one or two of the non-adjacent CH groups in the alkyl group ₂ The radicals may be substituted by oxygen atoms, in addition, more than one methylene group may be substituted by-CH=CH-or-CH≡CH-,

[ chemical 4]

Each independently of the other is

[ chemical 5]

[ chemical 6]

In addition, in the case of the optical fiber,

[ chemical 7]

[ chemical 8]

Z ¹¹ Z is as follows ¹² One of them is-C.ident.C-, the other, when present, is-C.ident.C-, -CF ₂ O-、-OCF ₂ -, trans-ch=ch-, trans-cf=cf-, -COO-, -CH ₂ -CH ₂ -、-CF ₂ -CF ₂ -or a single bond, n is 0 or 1)

ADVANTAGEOUS EFFECTS OF INVENTION

According to the present invention, a polymer-dispersed liquid crystal composition, a liquid crystal element, and a light control element, which are excellent in adhesion to a driving voltage, high in reliability, good in heat resistance, and particularly, low in transmittance decrease after heating and high in transparency when the voltage is turned on, can be obtained.

Detailed Description

Embodiments of the polymer-dispersed liquid crystal composition and polymer-dispersed liquid crystal element using the same according to the present invention will be described.

The present embodiment is described as a specific example for better understanding of the gist of the present invention, and the present invention is not limited to the specific example unless specified.

Polymer dispersed liquid Crystal composition

As described above, the polymer dispersed liquid crystal composition of the present invention contains the polymerizable compound (MA) and the non-polymerizable liquid crystal compound (LB). The polymerizable compound (MA) contains one or more cyclic monofunctional polymerizable compounds represented by the following general formula (ii) as a first component, and the non-polymerizable liquid crystal compound (LB) contains one or more diphenylacetylene compounds represented by the following general formula (iii) as a second component.

In the polymer dispersed liquid crystal composition of the present invention, the weight ratio (LB/MA) of the non-polymerizable liquid crystal compound (LB) to the polymerizable compound (MA) is preferably in the range of 30/70 to 70/30, more preferably 40/60 to 60/40, still more preferably 45/55 to 60/40, and particularly preferably 50/50. Hereinafter, each component constituting the polymerizable compound (MA) and each component constituting the non-polymerizable liquid crystal compound (LB) will be specifically described.

[ polymerizable Compound (MA) ]

[ first component ]

The first component is a cyclic monofunctional polymerizable compound represented by the following general formula (ii).

[ chemical 9]

P ⁱⁱⁱ¹ -Z ⁱⁱⁱ¹ -A ⁱⁱⁱ¹ (ii)

A ⁱⁱⁱ¹ the general formula is shown in the specification(ii-1) to general formula (ii-20).

[ chemical 10]

[ chemical 11]

(wherein, more than one-CH ₂ -can be independently passed through-O-, -S-, -COO-, -OCO-, -NH-, -NCH ₃ -or-CO-substitution, wherein in the case where two or more oxygen atoms and/or sulfur atoms are present in total in the general formulae (ii-1) to (ii-20), these are not bonded to each other as in-O-O-, -O-S-or-S-S-, and in addition, one or more-CH ₂ -CH ₂ -may be substituted with-ch=ch-group, and in addition, the hydrogen atom in the general formulae (ii-1) to (ii-20) may be substituted with an alkyl group having 1 to 8 carbon atoms, which may be a straight chain or a branched chain, one or more of the alkyl groups may be non-adjacent-CH ₂ -each independently substituted by-O-, -CO-, -COO-, or-OCO-in such a way that the oxygen atoms are not directly adjacent. In the formula, the black dots indicate the bond to Ziii 1))

The compound represented by the general formula (ii) as the first component is a material excellent in flexibility, and when the compound is used, cloudiness can be maintained even in a curved state. In addition, the compatibility of the components in the polymerizable composition can be improved while improving the adhesion. The compound represented by the general formula (ii) is a non-liquid crystalline compound.

In the compound represented by the general formula (ii), P in the formula ⁱⁱⁱ¹ The polymerizable functional groups are preferably represented by any one of the following formulas (P-1) to (P-21) independently. In the following formulas (P-1) to (P-21), the bond to a carbon atom or other atom is represented.

[ chemical 12]

Among the polymerizable groups represented by the above formulae (P-1) to (P-21), the formula (P-1), the formula (P-2), the formula (P-7), the formula (P-12), the formula (P-13) or the formula (P-21) is preferable, the formula (P-1), the formula (P-2), the formula (P-7) and the formula (P-21) are more preferable, and the formula (P-1), the formula (P-2) and the formula (P-21) are particularly preferable from the viewpoint of improving the polymerizability and the storage stability.

In the compound represented by the general formula (ii), Z in the formula ⁱⁱⁱ¹ Represents a single bond or an alkylene group having 1 to 7 carbon atoms, one or more of which are-CH ₂ -each independently substituted by-O-, -CO-, -COO-, or-OCO-in such a manner that the oxygen atoms are not directly adjacent, and one or more hydrogen atoms present in the alkylene group may each independently be substituted by a fluorine atom. Z in ⁱⁱⁱ¹ Preferably a single bond or an alkylene group having 1 to 6 carbon atoms, more preferably a single bond or an alkylene group having 1 to 3 carbon atoms, particularly preferably a single bond or-CH ₂ -a radical.

In the compound represented by the general formula (ii), A is ⁱⁱⁱ¹ In view of further improving the adhesion, the adhesion is preferably improved by the following formula A ⁱⁱⁱ¹ The heterocyclic structure containing a nitrogen atom, an oxygen atom and a sulfur atom is more specifically preferably represented by the following general formulae (ii-a 1) to (ii-a 11).

[ chemical 13]

(wherein, more than one-CH ₂ Each independently substituted by-CO-, and in addition, the hydrogen atom in the formulae (ii-a 1) to (ii-a 11) may be substituted by an alkyl group having 1 to 8 carbon atoms, one or more of the alkyl groups being not adjacent to-CH ₂ -each independently substituted by-O-, -CO-, -COO-, or-OCO-in such a way that the oxygen atoms are not directly adjacent. In addition, the hydrogen atom in the general formulae (ii-a 1) to (ii-a 11) may be substituted with an alkyl group having 1 to 8 carbon atoms, the alkyl group may be a straight chain or a branched chain, and one of the alkyl groups may be a branched chainOr more than two non-contiguous-CH ₂ -each independently substituted by-O-, -CO-, -COO-, or-OCO-in such a way that the oxygen atoms are not directly adjacent. In addition, the black dots in the formula represent the direction Z ⁱⁱⁱ¹ Bond) of (c))

In particular, when the cyclic structure has a nitrogen atom, the adhesion of the cyclic structure can be further improved by the presence of the nitrogen atom.

Specifically, the following compounds (II-34) to (II-51) are preferable.

[ chemical 14]

(wherein X ⁵ In the structural formulae (II-34) to (II-51), the hydrogen atom or methyl group is more preferably (II-34), (II-36), (II-38), (II-39), (II-40), (II-43), (II-45) or (II-47).

In terms of improving the adhesion, the content of the compound represented by the general formula (ii) as the first component is preferably 10 mass% or more, more preferably 20 mass% or more, and particularly preferably 30 mass% or more, relative to 100 mass% of the total amount of the polymerizable compounds (MA) contained in the polymer-dispersed liquid crystal composition of the present invention, in terms of improving the compatibility of the components in the polymerizable composition. In view of the reduction of the voltage, the content is preferably 80% by mass or less, more preferably 70% by mass or less, and particularly preferably 60% by mass or less.

[ third component ]

The polymerizable compound (MA) may further contain a third component.

The third component is a multifunctional (meth) acrylate oligomer having a weight average molecular weight of 2000 or more.

The multifunctional (meth) acrylate oligomer as the third component is a compound required for introducing a crosslinked structure into the network structure of the polymer and for obtaining good adhesion. Among the multifunctional (meth) acrylate oligomers, difunctional acrylate oligomers are preferred. Further, in order to pay attention to adhesion to a substrate, a urethane acrylate oligomer or a polyester acrylate oligomer is preferable, and a urethane acrylate oligomer is more preferable. The urethane acrylate oligomer includes polyester and polyether, but is preferably polyether. The molecular weight is 2000 or more, preferably 2000 to 60000, more preferably 2500 to 40000, still more preferably 2800 to 35000, and particularly preferably 3000 to 30000. This is because: if the molecular weight is too small, the degree of hardening shrinkage becomes large due to an increase in the crosslinking density caused by an increase in the (meth) acrylic group contained in one molecule, and the adhesiveness is deteriorated, whereas if the molecular weight is too large, the inter-crosslinking distance becomes long, and therefore the gap becomes large and the liquid crystal is easily taken in, and therefore the scattering property as a polymer dispersed liquid crystal is reduced. Namely, because: if left in an environment at high temperature, the polymer absorbs liquid crystal and the characteristics change greatly. In addition, when the molecular weight is large, the degree of decrease in the transition point Tnm of the polymer dispersed liquid crystal due to the addition of the polymerizable compound becomes small, and in order to keep Tnm at room temperature or less, a material having low Tni of the liquid crystal composition itself must be used, and as a result, there is also a problem that the operating temperature range becomes narrow.

The multifunctional urethane (meth) acrylate oligomer is obtained by reacting a hydroxyl group-containing acrylate with a polyol or a polyisocyanate. As the polyol, there may be mentioned: polyether polyols, polyester polyols, polycarbonate polyols, polycaprolactone polyols, polybutadiene polyols, and the like, and as the polyether polyols, there can be mentioned: polyethylene glycol, polypropylene glycol, polytetramethylene glycol, and the like.

As the polyisocyanate, there may be mentioned: 2, 4-toluene diisocyanate (Tolylene Diisocyanate, TDI), O-toluidine diisocyanate (O-Toluidine Diisocyanate, TODI), naphthylene diisocyanate (Naphthylene Diisocyanate, NDI), xylene diisocyanate (Xylene Diisocyanate, XDI), 4 '-diphenylmethane diisocyanate (4, 4' -Diphenyl Methane Diisocyanate, MDI), methylenebis (4-cyclohexyl isocyanate), xylylene diisocyanate, hydrogenated xylylene diisocyanate, hexamethylene diisocyanate, trans-cyclohexane 1, 4-diisocyanate, 1,6, 11-undecyltriacrylate, 1, 8-diisocyanate-4-isocyanatomethyl octane, 1,3, 6-hexamethylene triisocyanate, bicycloheptane triisocyanate, trimethylhexamethylene diisocyanate, dicyclopentadiene diisocyanate, norbornene diisocyanate, isophorone diisocyanate, carbodiimide-modified MDI, polymethylene polyphenyl isocyanate, polymeric polyisocyanate (polymeric polyisocyanate), and the like.

Examples of the hydroxyl group-containing (meth) acrylate include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, polypropylene glycol mono (meth) acrylate, 1, 4-cyclohexanedimethanol monoacrylate, epsilon-caprolactone modified mono (meth) acrylate, and the like.

Specifically, aliphatic urethane (meth) acrylate, aromatic urethane (meth) acrylate, and polyurethane diacrylate oligomer are preferable, polyether polyol, polyester polyol, and polycaprolactone polyol are preferable as the polyol to be used, polyether polyol and polyester polyol are particularly preferable, and polyisocyanate having a cyclic structure is preferable as the polyisocyanate to be used, and polyisocyanate having an alicyclic structure is particularly preferable. More specifically, o-toluidine diisocyanate (TODI), methylenebis (4-cyclohexyl isocyanate), xylylene diisocyanate, hydrogenated xylylene diisocyanate, trans-cyclohexane 1, 4-diisocyanate, 1,6, 11-undecane triisocyanate, bicycloheptane triisocyanate, dicyclopentadiene diisocyanate, norbornene diisocyanate, isophorone diisocyanate, carbodiimide-modified MDI, and particularly, methylenebis (4-cyclohexyl isocyanate), xylylene diisocyanate, hydrogenated xylylene diisocyanate, trans-cyclohexane 1, 4-diisocyanate, 1,6, 11-undecane triisocyanate, bicycloheptane triisocyanate, dicyclopentadiene diisocyanate, norbornene diisocyanate, isophorone diisocyanate are preferable.

The hydroxyl group-containing (meth) acrylate used is preferably 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1, 4-cyclohexanedimethanol monoacrylate, and mono (meth) acrylate modified with epsilon-caprolactone, and particularly preferably 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.

In addition, the compounds of the following general formula (i-1) are also preferable.

[ 15]

(wherein X is ⁱ¹ Each independently represents a hydrogen atom or a methyl group, B ¹ Each independently represents an alkyl group having 1 to 4 carbon atoms, and at least one of the alkyl groups is-CH ₂ -can be substituted by oxygen atoms, -CO-, -COO-, -OCO-, b represents 1-20, B ² The following items (i-2) to (i-6) may be used singly or in combination,

[ 16]

B ³ The groups selected from the following general formulae (i-7), (i-8) and (i-9) may be either one or a combination thereof

[ chemical 17]

/>

[ chemical 18]

(wherein X is ⁱ² Represents a hydrogen atom or a methyl group, X ⁱ² Represents an alkyl group having 1 to 9 carbon atoms,

Y ⁵ an alkylene group having 1 to 15 carbon atoms, a divalent aromatic group, a divalent alicyclic hydrocarbon group,

Y ³ 、Y ⁴ Represents a hydrogen atom or a methyl group,

t, t1 and t2 each independently represent an integer of 0 to 300, and t+t1+t2 represents an integer of 20 to 300)

Further, aliphatic urethane acrylate and polyurethane diacrylate oligomers are particularly preferable.

From the viewpoint of improving the adhesion, the content of the polymerizable compound (MB) selected from the polyfunctional (meth) acrylate oligomer having a weight average molecular weight of 2000 or more as the third component is preferably 5% by mass or more, more preferably 15% by mass or more, and particularly preferably 25% by mass or more, relative to 100% by mass of the total amount of the polymerizable compounds (MB) contained in the polymer dispersed liquid crystal composition of the present invention. In view of the reduction of the voltage, the content is preferably 80% by mass or less, more preferably 60% by mass or less, and particularly preferably 50% by mass or less.

[ fourth component ]

The polymerizable compound (MA) may further contain a fourth component. The fourth component is preferably one or more selected from the group consisting of a polyfunctional polymerizable oligomer and a polyfunctional polymerizable monomer having a weight average molecular weight of less than 2000 represented by the following general formula (iv). The molecular weight of the polyfunctional polymerizable oligomer and/or the polyfunctional polymerizable monomer is preferably 2000 or less, more preferably 1000 or less.

[ chemical 19]

(wherein Y is ³¹ Represents a hydrogen atom or a methyl group,

X ³¹ representing the number of carbon atoms130 or less, the alkylene group may have a cyclic hydrocarbon group or a branched chain, and one or more of the alkylene groups or the cyclic hydrocarbon groups may be-CH ₂ The radicals may each independently be interrupted by-O-, by oxygen atoms which are not directly adjacent to one another-NH-, -CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, one or more hydrogen atoms present in the alkylene or cyclic hydrocarbon group may each independently be substituted with a fluorine atom or-OH,

n ³¹ an integer of 2 to 6

The polyfunctional polymerizable oligomer or the polyfunctional polymerizable monomer having a weight molecular weight of less than 2000 represented by the general formula (iv) is preferably a polymerizable compound represented by the general formula (iv-1).

[ chemical 20]

(wherein Y is ¹ Y and Y ² Represents a hydrogen atom or a methyl group,

X ¹ represents a straight-chain or branched alkylene group having 2 to 80 carbon atoms, any carbon atom of the alkylene group may be substituted by-O-, -CO-, -COO-, -OCO-, -ch=ch-, -c≡c-or OH substitution)

Here, in the general formula (iv-1), X ¹ The number of carbon atoms of the straight-chain or branched alkylene group is in the range of 2 to 70, but the number of carbon atoms is preferably in the range of 6 to 70, and among them, the range of 8 to 60 is preferable, and the range of 9 to 50 is particularly preferable in terms of a reduction in driving voltage.

Examples of the polymerizable compound represented by the general formula (iv-1) include compounds having the following structures.

[ chemical 21]

(wherein n and m represent n+m is 1 to 10, n ² Represents 1 to 18, n ³ M ² Represents n ³ +m ² Has a value of 1 to 18, n ⁴ Represents 1 to 23, n ⁵ Represents 1 to 23, n ⁶ Represents 4 to 30, n ⁷ Represents 2 to 10, n ⁸ N is as follows ⁹ Representation 2-10)

The content of the polymerizable compound represented by the general formula (iv) as the fourth component is preferably 2% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, and particularly preferably 50% by mass or less, 40% by mass or less, 30% by mass or less, 25% by mass or less, relative to 100% by mass of the total amount of the polymerizable compounds (MA) contained in the polymer dispersed liquid crystal composition of the present invention, from the viewpoint of improving heat resistance.

[ fifth component ]

The polymerizable compound (MA) may further contain a fifth component. The fifth component is preferably a chain monofunctional polymerizable compound represented by the following general formula (v).

[ chemical 22]

P ^iia1 -R ^iia2 (v)

(wherein P ^iia1 Represents a polymerizable group and is preferably a polymerizable group,

R ^iia2 represents a linear or branched alkyl group having 1 to 22 carbon atoms, one or more of which are-CH ₂ -each independently substituted by-O-, -CO-, -COO-, or-OCO-in such a manner that the oxygen atoms are not directly adjacent, one or more hydrogen atoms present in the alkyl group being each independently substituted by a fluorine atom or-OH)

In the compound represented by the general formula (v), P in the formula ^iia1 Represents a polymerizable functional group, preferably P in the general formula (ii) ⁱⁱⁱ¹ The polymerizable groups represented are the same.

In the compound represented by the general formula (v), R in the formula ^iia2 More preferably a straight-chain or branched alkyl group having 3 to 20 carbon atoms, particularly preferably a straight-chain or branched alkyl group having 6 to 18 carbon atoms, still more preferably a branched alkyl group, particularly preferably a branched alkyl group having 9 to 24 carbon atoms, in view of suppressing crystallinity.

At R ^iia2 In the case of a linear alkyl group, the compound represented by the general formula (v) is preferably, for example, a mono (meth) acrylate having a linear alkyl chain such as ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, hexadecyl (meth) acrylate, stearyl (meth) acrylate, and behenyl (meth) acrylate, or a mono (meth) acrylate having a linear alkyl chain represented by the following structure.

The compound represented by the general formula (v) is preferably R in the general formula (v) ^iia1 An acrylic acid ester having a linear ether chain structure. The acrylic acid ester having the ether chain structure is preferably a compound represented by the following structure.

[ chemical 23]

(in the general formulae (v-a 1) to (v-a 3), q represents an integer of 1 to 12, preferably an integer of 1 to 5, and more preferably an integer of 1 to 3)

In the general formula (v), it is preferable to use a mono (meth) acrylate having a linear alkyl chain, in particular, from the viewpoint of maintaining the transparency when no voltage is applied well and making the effect of reducing the driving voltage remarkable.

At R ^iia2 In the case of a branched alkyl group, the compound represented by the general formula (v) is preferably a mono (meth) acrylate having a branched alkyl chain represented by the following structure. The compound represented by the general formula (v) is preferably isobutyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, isomyristyl (meth) acrylate, or isostearyl (meth) acrylate.

[ chemical 24]

[ chemical 25]

(wherein q represents an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3)

Among these, in particular, a mono (meth) acrylate having a branched alkyl chain is preferably used in order to maintain the transparency when no voltage is applied and to make the effect of reducing the driving voltage remarkable.

In view of low-voltage driving, the content of the chain-like monofunctional polymerizable compound represented by the general formula (v) as the fifth component is preferably 5% by mass or more, more preferably 10% by mass or more, and particularly preferably 15% by mass or more, relative to 100% by mass of the total amount of the polymerizable compounds (MA) contained in the polymer-dispersed liquid crystal composition of the present invention, from the viewpoint of improving the compatibility of the components in the polymerizable composition. In view of adhesion, it is preferably 60 mass% or less, more preferably 50 mass% or less, and particularly preferably 40 mass% or less.

[ other polymerizable Compound ]

The polymerizable compound (MA) may or may not contain a polymerizable compound having a mesogenic skeleton as another polymerizable compound. Examples of such polymerizable compounds include compounds represented by the following general formulae (2) to (8).

[ chemical 26]

In the general formulae (2) to (8), P ¹¹ ～P ⁷⁴ Preferably, the polymerizable groups are each independently represented by any one of the following formulas (P-1) to (P-20). In the following formulas (P-1) to (P-20), the bond to a carbon atom or other atom is represented.

[ chemical 27]

Among the polymerizable groups represented by the formulae (P-1) to (P-20), the formulae (P-1) and (P-2) are preferable from the viewpoint of improving the polymerizability and the storage stability.

X ¹¹ ～X ⁷² Each independently represents-O-, -S-, -OCH ₂ -、-CH ₂ O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH ₂ -、-CH ₂ S-、-CF ₂ O-、-OCF ₂ -、-CF ₂ S-、-SCF ₂ -、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH ₂ CH ₂ -、-OCO-CH ₂ CH ₂ -、-CH ₂ CH ₂ -COO-、-CH ₂ CH ₂ -OCO-、-COO-CH ₂ -、-OCO-CH ₂ -、-CH ₂ -COO-、-CH ₂ -OCO-, -ch=ch-, -n=n-, -ch=n-n=ch-, -cf=cf-, -c≡c-, or a single bond, in X ¹¹ ～X ⁷² Where there are a plurality, these may be the same or different each other (wherein each P- (S-X) -bond does not contain-O-), particularly preferred are groups selected from the group consisting of single bonds, -O-, -S-, -CO-, -COO-, -OCO-.

M ¹¹ 、M ²¹ 、M ³¹ 、M ⁵¹ 、M ⁷¹ Each independently represents a mesogenic group represented by the following general formula (9-a)

[ chemical 28]

(in the general formula (9-a), A ⁹¹ 、A ⁹² 、A ⁹³ Each independently is a divalent radical having at least one or more ring structures, said divalent radical representing a member selected from the group consisting of 1, 2-cyclopropylene, 1, 3-cyclobutylene, 2, 5-cyclopentylene, octahydro-4, 7-methano-1H-indene-1, 5-diyl, octahydro-4, 7-methano-1H-indene-1, 6-diyl, octahydro-4, 7-methano-1H-indene-2, 5-diyl, tricyclo [3.3.1.1 ] ^3,7 ]-1, 3-diyl, 1, 4-phenylene, 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, tetrahydrothiopyran-2, 5-diyl, 1, 4-bicyclo (2, 2) octylene, decalin-2, 6-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, pyrazine-2, 5-diyl, thiophene-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, naphthylene-1, 4-diyl, naphthylene-1, 5-diyl, naphthylene-1, 6-diyl, phenanthrene-2, 7-diyl, 9, 10-dihydrophenanthrene-2, 7-diyl, benzothiazolyl, 1,2,3, 10, 9,10 a-dihydrophenanthrene-2, 7-diyl, 1, 10 a-dihydrobenzo [ 2, 7-b-2, 4 a-diyl; 4,5-b']Dithiophene-2, 6-diyl, benzo [1,2-b:4,5-b ]']Diselenophen-2, 6-diyl, [1 ]]Benzothieno [3,2-b ]]Thiophene-2, 7-diyl, [1]Benziselenopheno [3,2-b ]]Selenophene-2, 7-diyl or fluoren-2, 7-diyl, which may be unsubstituted or substituted by more than one L ¹ Substituted, but in which a plurality of A's are present ⁹¹ And/or A ⁹² Each of which may be the same or different,

Z ⁹¹ z is as follows ⁹² Each independently represents-O-, -S-, -OCH ₂ -、-CH ₂ O-、-CH ₂ CH ₂ -、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH ₂ -、-CH ₂ S-、-CF ₂ O-、-OCF ₂ -、-CF ₂ S-、-SCF ₂ -、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH ₂ CH ₂ -、-OCO-CH ₂ CH ₂ -、-CH ₂ CH ₂ -COO-、-CH ₂ CH ₂ -OCO-、-COO-CH ₂ -、-OCO-CH ₂ -、-CH ₂ -COO-、-CH ₂ -OCO-, -ch=ch-, -n=n-, -ch=n-, -n=ch-, -ch=n-n=ch-, -cf=cf-, -c≡c-, or a single bond, but in the presence of a plurality of Z' s ⁹¹ And/or Z ⁹² Each of which may be the same or different,

j ⁹¹ J ⁹² Each independently represents 0 to 4,j ⁹¹ +j ⁹² Represents an integer of 1 to 4, L ¹ Represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfonyl group, a nitro group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a-CH group ₂ -or not more than two adjacent-CH ₂ -can be each independently passed through-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -ch=ch-COO-, -COO-ch=ch-, -OCO-ch=ch-, -cf=cf-, -n=n-, -CR ¹ ＝N-N＝CR ¹ -or-C≡C-substituted straight-chain alkyl or branched alkyl having 1 to 20 carbon atoms, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom (further, R ¹ An alkyl group having 1 to 20 carbon atoms, which may be linear or branched, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and wherein one of the alkyl groups is-CH ₂ -or not more than two adjacent-CH ₂ Each independently through-O-, -S-, and-CO-, -COO-, -OCO-, -CO-S-, and-S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-or-C.ident.C-substitution)).

In addition, M ⁴¹ Is provided with as the A ⁹¹ 、A ⁹² 、A ⁹³ Exemplary trivalent organic groups of the ring structure, M ⁶¹ Is provided with as the A ⁹¹ 、A ⁹² 、A ⁹³ Tetravalent organic radicals of the exemplified ring structures.

In the general formulae (2) to (8), R ¹¹ 、R ³¹ Each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms, which may be linear or branched, and among the alkyl groupsCan be substituted by fluorine atoms, one of the alkyl groups-CH ₂ -or not more than two adjacent-CH ₂ Each independently through-O-, -S-, and-CO-, -COO-, -OCO-, -CO-S-, and-S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-or-C.ident.C-substitution,

m1 to m7, n2 to n7, l4 to l6, and k6 each independently represent an integer of 0 to 5. In the general formulae (2) to (8), S ¹¹ ～S ⁷² Each independently represents a spacer or represents a single bond, the S ¹¹ ～S ⁷² The spacer represented represents an alkylene group having 1 to 18 carbon atoms, which may be substituted with one or more halogen atoms, CN groups, alkyl groups having 1 to 8 carbon atoms, or alkyl groups having 1 to 8 carbon atoms having a polymerizable functional group, one CH being present in the group ₂ Based on or not adjacent two or more CH' s ₂ The radicals can each independently of one another be bound directly to one another by-O-, in the form of oxygen atoms-S-, -NH-, -N (CH) ₃ ) -, -CO-, -CH (OH) -, CH (COOH), -COO-, -OCO-, and-OCOO-, -SCO-, -COS-or-C≡C-substitution. Among these spacers, preferred are a linear alkylene group having 2 to 8 carbon atoms, an alkylene group having 2 to 6 carbon atoms substituted with a fluorine atom, and an alkylene group having 5 to 14 carbon atoms, a part of which is substituted with-O-. In addition, at S ¹¹ ～S ⁷² Where there are plural, these may be the same or different.

In the general formulae (2) to (8), m1 to m7, n2 to n7, l4 to l6, and k6 each independently represent an integer of 0 to 5, and m1 to m7, n2 to n7, l4 to l6, and k6 each independently preferably are 0 or 1.

The total content of the polymerizable compounds other than the first component, the third component, the fourth component and the fifth component is preferably 2% by mass or more, more preferably 5% by mass or more, and particularly preferably 10% by mass or more, relative to 100% by mass of the total amount of the polymerizable compounds (MA) contained in the polymer-dispersed liquid crystal composition of the present invention, from the viewpoints of alignment and transparency. In view of scattering property and low-voltage driving, it is preferably 80 mass% or less, more preferably 70 mass% or less, and particularly preferably 60 mass% or less.

[ additives ]

In order to achieve a composition in which adhesion is more important, the polymerizable compound (MA) of the present invention preferably contains an additive represented by the following general formula (X) in addition to the first component, the third component, the fourth component, the fifth component, and the other polymerizable compound.

[ chemical 29]

(in the formula, preferably, Y ³¹ Represents a hydrogen atom or a methyl group,

X ³¹ represents an alkylene group having 130 or less carbon atoms, the alkylene group may have a cyclic hydrocarbon group or a branched chain, and one or more of the alkylene groups or the cyclic hydrocarbon groups may be-CH ₂ The radicals may each independently be interrupted by-O-, by oxygen atoms which are not directly adjacent to one another-NH-, -CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, one or more hydrogen atoms present in the alkylene or cyclic hydrocarbon group may each independently be substituted with a fluorine atom or-OH,

n ³¹ an integer of 1 to 6 is represented,

X ³¹ has a group represented by the following formula (X-1)

[ chemical 30]

Specifically, the following compounds are preferably added.

[ 31]

[ chemical 32]

(wherein X ⁶ 、X ⁷ X is X ⁸ Each independently represents a hydrogen atom or a methyl group, q, r and s represent 1 to 4)

The amount of the compound having the group represented by the general formula (X-1) added is preferably 0.005 mass% or more and 2 mass% or less, more preferably 0.01 mass% or more and 0.5 mass% or less, and still more preferably 0.01 mass% or more and 0.2 mass% or less, based on the total amount of the polymer-dispersed liquid crystal composition.

[ non-polymerizable liquid Crystal Compound (LB) ]

[ second component ]

The second component is one or more of diphenyl acetylene compounds represented by the following general formula (iii).

[ 33]

[ chemical 34]

A kind of electronic device with high-pressure air-conditioning system

Each independently of the other is

[ 35]

Or is a

[ 36]

In addition, in the case of the optical fiber,

[ 37]

(may be)

[ 38]

The liquid crystal element using the polymer dispersed liquid crystal composition containing the non-polymerizable liquid crystal compound (LB) contains one or two or more of the diphenylacetylene compounds represented by the general formula (iii), and therefore has excellent adhesion and light scattering properties and can be driven at low voltage at room temperature and low temperature.

In addition, it is preferable that the method comprises the steps of,

[ 39]

Or a mirror image of these,

[ 40]

Or a mirror image of these,

[ chemical 41]

Or a mirror image of these.

The polymer dispersed liquid crystal composition of the present invention preferably contains, in terms of high scattering

[ chemical 42]

Is that

[ chemical 43]

As the compound represented by the general formula (iii). In addition, the polymer dispersed liquid crystal composition of the present invention preferably contains, in terms of high-speed response

[ 44]

A kind of electronic device with high-pressure air-conditioning system

/>

At least one of (a) is

[ 45]

As the compound represented by the general formula (iii).

The compound represented by the formula (iii) is preferably a compound represented by the following formulae (iii-1) to (iii-7).

[ chemical 46]

(wherein R is ¹¹ R is R ¹² Has the meaning shown in the formula (iii), Y ¹¹ Y and Y ¹² Independently of one another H or F

Of these, the compounds represented by the general formula (iii) are more preferably compounds represented by the subordinate general formulae (iii-6) to (iii-7).

The compound represented by the general formula (iii) may be a compound represented by the following subordinate general formula (iii-8).

[ 47]

(wherein R is ¹¹ R is R ¹² Has the meaning shown in the general formula (iii), Y ¹¹ Are independently of each other H or F, Y ¹³ Is a hydrogen atom, a fluorine atom or a methyl group)

The compound represented by the general formula (iii) as the third component is preferably 10 mass% or more and 80 mass% or less, more preferably 25 mass% or more and 70 mass% or less, and still more preferably 35 mass% or more and 60 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal compounds (LB).

[ sixth ingredient ]

The non-polymerizable liquid crystal compound (LB) preferably further contains one or more compounds represented by the following general formula (vi-0) as a sixth component (wherein the second component is excluded).

[ 48]

(wherein R is ¹¹ Represents an alkyl group having 1 to 10 carbon atoms, one or two of which are not adjacent to each other ₂ The radicals may be substituted by oxygen atoms, -COO-, -OCO-, and, in addition, more than one methylene group may be substituted by-CH≡CH-, R ¹² Represents fluorine atom, chlorine atom, cyano group, CF ₃ Radical, OCF ₃ Radical, OCHF ₂ A group, NCS group, cyano group or C1-10 alkyl group, one or two of which are not adjacent CH ₂ The radicals may be substituted by oxygen atoms, -COO-, -OCO-, and, in addition, more than one methylene group may be substituted by-C.ident.C-, preferably a fluorine atom, a cyano group or an alkyl group having 1 to 5 carbon atoms (one or two of the alkyl groups being not adjacent to each other CH ₂ The groups may be substituted with oxygen atoms),

Z ¹¹ z is as follows ¹² Each independently represents a single bond, -COO-, -OCO-, -CH ₂ -CH ₂ -、-CH＝CH-、-CF ₂ O-、-OCF ₂ -or-C≡C-, at Z ¹² Where there are plural, they may be the same or different,

A ¹¹ 、A ¹² a is a ¹³ Independently of one another, 1, 4-phenylene, 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, decalin-2, 6-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, pyrazine-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 2, 6-naphthylene, which 1, 4-phenylene, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 2, 6-naphthylene may be unsubstituted orHaving one or more fluorine atoms, chlorine atoms, CF ₃ Radical, OCF ₃ Radicals or CH ₃ The radicals being substituents, in A ¹³ Where there are plural, they may be the same or different,

n ¹¹ 0, 1 or 2. Wherein the second component is excluded

As the compound of the formula (vi-0), R in the formula (vi-0) ¹¹ Preferably an alkyl group having 1 to 5 carbon atoms (one or two of the non-adjacent CH's in the alkyl group) ₂ The radicals may be substituted by oxygen atoms), R ¹² Preferably a fluorine atom, a cyano group or an alkyl group having 1 to 5 carbon atoms (one or two of the alkyl groups being not adjacent to each other CH ₂ Groups may be substituted by oxygen atoms), Z ¹¹ Z is as follows ¹² Preferably each independently is a single bond, -COO-, -OCO-, -CH ₂ -CH ₂ -、-CF ₂ O-or-OCF ₂ - (at Z) ¹¹ And may be the same or different when a plurality of them are present), more preferably a single bond, -COO-, -CF ₂ O-，A ¹¹ 、A ¹² A is a ¹³ Preferably each independently is 1, 4-phenylene, 1, 4-cyclohexylene, 1, 3-dioxane-2, 5-diyl, pyrimidine-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 2, 6-naphthylene (the 1, 4-phenylene, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 2, 6-naphthylene may be unsubstituted or have one or more fluorine atoms or CH ₃ The radicals being substituents, in A ¹³ And may be the same or different when a plurality of them are present), more preferably 1, 4-phenylene, 1, 4-cyclohexylene, pyrimidine-2, 5-diyl, 2, 6-naphthylene (the 1, 4-phenylene, 2, 6-naphthylene may be unsubstituted or have one or more fluorine atoms or CH ₃ The radicals being substituents, in A ¹³ The same or different when a plurality of n are present), n ¹ Preferably 0 or 1.

The sixth component is more preferably one or two or more liquid crystalline compounds represented by the following general formula (vi).

[ 49]

(wherein R is ³ Represents an alkyl group having 1 to 10 carbon atoms, one or more non-adjacent-CH groups in the alkyl group ₂ The radical may be substituted by an oxygen atom, -CH=CH-, -COO-, -OCO-,

ring A ⁶ Represents 1, 4-phenylene, 1, 4-cyclohexylene, 1, 3-dioxane-2, 5-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, the 1, 4-phenylene radical being unsubstituted or having one or more fluorine atoms, chlorine atoms, CF ₃ 、OCF ₃ Or a methyl group as a substituent,

ring A ⁷ Represents 1, 4-phenylene or 1, 4-cyclohexylene, the 1, 4-phenylene radicals being unsubstituted or having one or more fluorine atoms, chlorine atoms, CF ₃ 、OCF ₃ Or a methyl group as a substituent,

ring A ⁸ Represents 1, 4-phenylene, which 1, 4-phenylene may be unsubstituted or have one or more fluorine atoms, chlorine atoms, CF ₃ 、OCF ₃ Or a methyl group as a substituent,

Z ⁶ 、Z ⁷ each independently represents a single bond, -COO-, -OCO-, -CH ₂ -CH ₂ -、-CH＝CH-、-CF ₂ O-、-OCF ₂ -or-c≡c-,

n represents 0 or 1. Wherein the second component is excluded

In the general formula (vi), R ³ More preferably an alkyl group having 1 to 10 carbon atoms or an alkoxy group. Ring A ⁶ More preferred are 1, 4-phenylene and 1, 4-cyclohexylene (the 1, 4-phenylene may be unsubstituted or have one or more fluorine atoms as substituents). Further preferably selected from Y ⁴ 、Y ⁵ 、Y ⁸ Y and Y ⁹ One of the groups formed represents a fluorine atom and the remaining three all represent hydrogen atoms. Z is Z ⁶ 、Z ⁷ More preferably, each independently is a single bond, -COO-, -OCO-, -CH ₂ -CH ₂ -, more preferably a single bond or-COO-.

In the general formula (vi), R is most preferably ³ Represents an alkyl group having 1 to 10 carbon atoms, preferablyAn alkyl group selected from 2 to 7, more preferably an alkyl group selected from 2 to 5,

ring A ⁶ Represents 1, 4-phenylene, 1, 4-cyclohexylene, the 1, 4-phenylene being unsubstituted or having one fluorine atom as a substituent,

n represents 0.

When a compound of the general formula (vi) in which ring A is used, it is preferable in terms of lowering the voltage ⁷ Ring A ⁸ Represents a 1, 4-phenylene group, any one of the 1, 4-phenylene groups having at least one or more fluorine atoms as a substituent, Z ⁶ 、Z ⁷ Z is as follows ⁸ Represents a single bond or-COO-, ring A ⁶ Represents a 1, 4-phenylene group or a 1, 4-cyclohexylene group, and n represents 0 or 1.

Specifically, the following compounds (vi-1) to (vi-10) are exemplified.

[ 50]

(wherein R is ⁵¹ Represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, Y ¹¹ ～Y ⁶² Each independently represents a hydrogen atom or a fluorine atom. Y is Y ¹¹ ～Y ⁶² Can be all hydrogen atoms or one or more of them can be fluorine atoms

Specifically, the following compounds (vi-A) to (vi-F) are exemplified.

[ 51]

(wherein R is ⁵¹¹ An alkyl group having 2 to 7 carbon atoms or an alkoxy group having 2 to 7 carbon atoms, preferably an alkyl group having 2 to 5 carbon atoms or an alkoxy group having 2 to 5 carbon atoms

The compound represented by the general formula (vi-0) as the sixth component is preferably 20 mass% or more and 90 mass% or less, more preferably 30 mass% or more and 75 mass% or less, and still more preferably 40 mass% or more and 65 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal compounds (LB).

The total content of the liquid crystal compounds represented by the general formula (vi) as the sixth component is preferably 2 mass% or more and 70 mass% or less, more preferably 5 mass% or more and 50 mass% or less, and still more preferably 10 mass% or more and 30 mass% or less, with respect to 100 mass% of the total amount of the non-polymerizable liquid crystal compounds (LB).

Further, the total content of the liquid crystal compounds represented by the general formulae (vi-1) to (vi-10) as the sixth component is preferably 2% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 50% by mass or less, and still more preferably 10% by mass or more and 30% by mass or less, based on 100% by mass of the total amount of the non-polymerizable liquid crystal compounds (LB).

Further, the total content of the liquid crystal compounds represented by the general formulae (vi-a) to (vi-F) as the sixth component is preferably 2% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 50% by mass or less, and still more preferably 10% by mass or more and 30% by mass or less, based on 100% by mass of the total amount of the non-polymerizable liquid crystal compounds (LB).

The refractive index anisotropy (Δn) of the non-polymerizable liquid crystal composition used in the polymer dispersed liquid crystal element is generally preferably high, and Δn is preferably 0.16 or more, more preferably 0.18 or more, still more preferably 0.20 or more, and most preferably 0.22 or more. The ordinary refractive index (no) of the non-polymerizable liquid crystal composition having the Δn is usually about 1.50 to 1.54. When a voltage is applied to the polymer dispersed liquid crystal element to make it transparent, high transparency can be obtained if no of the non-polymerizable liquid crystal composition is substantially equal to the refractive index (np) of the polymer forming the network structure. However, when the monomer or oligomer is polymerized by UV irradiation or the like, the actual polymer has a higher refractive index than the pure polymer because it is cured as a non-polymerizable liquid crystal composition surrounding a part. Therefore, the refractive index of the monomer and oligomer is preferably less than 1.5, more preferably 1.48 or less, and still more preferably 1.47 or less.

[ polymerization initiator ]

The polymer dispersed liquid crystal composition of the present invention may contain a polymerization initiator. The polymerization initiator used in the present invention is used to polymerize the liquid crystal composition of the present invention. The photopolymerization initiator used for polymerization by irradiation with light is not particularly limited, and a conventionally known photopolymerization initiator may be used to such an extent that the polymerizable compound having one polymerizable group and satisfying the formula (I) and the polymerizable compound having a mesogenic skeleton are oriented.

Examples include: 1-hydroxycyclohexyl phenyl ketone "Ornidad (Omnirad) 184", 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one "Ornidad (Omnirad) 1173", 2-methyl-1- [ (methylthio) phenyl ] -2-morpholinopropane-1 "Ornidad (Omnirad) 907", 2-dimethoxy-1, 2-diphenylethane-1-one "Ornidad (Omnirad) BDK", 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone "Ornidad (Omnirad) 369", 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholinophenyl) butan-1-one "Ornidad (Omnii) 379", 2-dimethoxy-2-phenyl "Ornidad (Omnirad) 651", 2-dimethoxy-1, 2-diphenylethane-1, 2-dion (Omnirad) BDK ", 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone (Omnirad) 369", triphenyl-O-m-4-morpholinophenone (Omnirad) 3, 1- [4- (phenylthio) -,2- (o-benzoyl oxime), ethanone "yanjia solid (Irgacure) OXE 01"), 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (O-acetyl oxime) "Bright (Irgacure) OXE02", "Bright (Irgacure) OXE04" (manufactured by Basf Co., ltd.), "Adjacobian (Adeka cruise) NCI-831", "Adjacobian (Adeka cruise) NCI-930", "Adjacobian (Adeka cruise) N-1919" (manufactured by Ai Dike (ADEKA)) and a mixture of 2, 4-diethylthioxanthone (manufactured by Japanese chemical Co. "Kayacure (Kayacure) DETX") and ethyl p-dimethylaminobenzoate (manufactured by Japanese chemical Co. "Kayacure EPA"): mixtures of isopropylthioxanthone (Wo Debu Ron Jin Suopu (Ward Blenkinsop) manufactured by Kuntze (Quantacure) ITX ") with ethyl p-dimethylaminobenzoate," easy sun cure (Esacum) ONE "," easy sun cure (Esacum) KIP150"," easy sun cure (Esacum) KIP160"," easy sun cure (Esacum) 1001M "," easy sun cure (Esacum) A198"," easy sun cure (Esacum) KIP IT "," easy sun cure (Esacum) KTO46" "easy solid (Esacure) TZT" (Ning Baidi (manufactured by lamberti) inc., "solid of si (SpeedCure) BMS", "solid of si (SpeedCure) PBZ", "benzophenone" (manufactured by LAMBSON) and the like. Further, as the photo cation initiator, a photoacid generator can be used. As the photoacid generator, there may be mentioned: diazodisulfone compounds, triphenylsulfonium compounds, phenylsulfone compounds, sulfonylpyridine compounds, triazine compounds, diphenyliodine compounds, and the like.

The content of the photopolymerization initiator is preferably 0.1 mass% or more and 10 mass% or less, more preferably 0.2 mass% or more and 6 mass% or less, relative to 100 mass% of the total amount of the polymerizable compounds (MA) used in the polymer-dispersed liquid crystal composition of the present invention. These may be used alone or in combination of two or more.

As the thermal polymerization initiator used in the thermal polymerization, a known and conventional thermal polymerization initiator can be used, and for example, a thermal polymerization initiator can be used: methyl acetoacetate peroxide, cumene hydroperoxide, benzoyl peroxide, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butyl peroxybenzoate, methyl ethyl ketone peroxide, 1-bis (t-hexyl peroxy) 3, 5-trimethylcyclohexane, para-pentahydroperoxide, t-butyl hydroperoxide, dicumyl peroxide, isobutyl peroxide, bis (3-methyl-3-methoxybutyl) peroxydicarbonate organic peroxides such as 1, 1-bis (t-butylperoxy) cyclohexane, azonitrile compounds such as 2,2' -azobisisobutyronitrile and 2,2' -azobis (2, 4-dimethylvaleronitrile), azoamidine compounds such as 2,2' -azobis (2-methyl-N-phenylpropionamidine) dihydrochloride, azoamide compounds such as 2,2' -azobis { 2-methyl-N- [1, 1-bis (hydroxymethyl) -2-hydroxyethyl ] propionamide }, and alkylazo compounds such as 2,2' -azobis (2, 4-trimethylpentane). The content of the thermal polymerization initiator is preferably 0.1 mass% or more and 10 mass% or less, more preferably 1 mass% or more and 6 mass% or less, relative to 100 mass% of the total amount of the polymerizable compounds (MA) used in the polymerizable composition of the polymer-dispersed liquid crystal composition of the present invention. These may be used alone or in combination of two or more.

The polymer-dispersed liquid crystal composition of the present invention may contain a polymerization inhibitor, an antioxidant, a light stabilizer, a chain transfer agent, a pigment, particles having a particle diameter of less than 1 μm, a chiral compound or an alignment material in such a range that practical electro-optical properties and adhesion properties at the time of producing a polymer-dispersed liquid crystal element are not impaired. Among them, the polymer dispersed liquid crystal composition preferably contains one or more selected from the group consisting of polymerization inhibitors, antioxidants, light stabilizers, particles having a particle diameter of less than 1 μm, pigments, and pigments.

[ polymerization inhibitor ]

The polymerization inhibitor used in the present invention can be used for controlling the electro-optical properties by controlling the polymerization reaction of the polymer dispersed liquid crystal composition of the present invention, or for assisting the efficacy of the polymerizable compound having polarity as the third component. As such a compound, a known and conventional compound can be used.

Examples of the phenol compounds include p-methoxyphenol, cresol, t-butylcatechol, 3, 5-di-t-butyl-4-hydroxytoluene, 2' -methylenebis (4-methyl-6-t-butylphenol), 2' -methylenebis (4-ethyl-6-t-butylphenol), 4' -thiobis (3-methyl-6-t-butylphenol), 4-methoxy-1-naphthol, 4' -dialkoxy-2, 2' -bi-1-naphthol, and other phenol compounds, hydroquinone, methylhydroquinone, t-butylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, t-butyl-p-benzoquinone, 2, 5-diphenylbenzoquinone, 2-hydroxy-1, 4-naphthoquinone, 2, 3-dichloro-1, 4-naphthoquinone, anthraquinone, and diphenoquinone, and particularly preferable examples thereof are p-methoxyphenol, 4-methoxy-1-naphthol, t-butylhydroquinone, 2-hydroxy-1, 4-naphthoquinone.

The content of the polymerization inhibitor is preferably 0 mass% or more and 2.0 mass% or less, more preferably 0 mass% or more and 0.5 mass% or less, relative to 100 mass% of the total amount of the polymerizable compounds (MA) used in the polymerizable composition of the polymer-dispersed liquid crystal composition of the present invention.

[ antioxidant ]

The antioxidant used in the present invention can be used to impart practical durability to the polymer dispersed liquid crystal element of the present invention. As such a compound, hydroquinone derivatives, nitrosamine polymerization inhibitors, hindered phenol antioxidants, and the like can be used.

In particular, the method comprises the steps of, preferred are t-butylhydroquinone, and "Q-1300", "Q-1301", pentaerythritol tetrakis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] "Yi Lunuo s (IRGANOX) 1010", thiodiethylene bis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] "Yi Lunuo s (IRGANOX) 1035", octadecyl-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate "IRGANOX 1076", "Yi Lunuo s (IRGANOX) 1135", "Yi Lunuo s (IRGANOX) 1330", 4, 6-bis (octylthiomethyl) -o-cresol "Yi Lunuo s (IRGANOX) 1520L", from Wako pure chemical industries, inc.; "Yi Lunuo S (IRGANOX) 1726", "Yi Lunuo S (IRGANOX) 245", "Yi Lunuo S (IRGANOX) 259", "Yi Lunuo S (IRGANOX) 3114", "Yi Lunuo S (IRGANOX) 3790", "Yi Lunuo S (IRGANOX) 5057", "Yi Lunuo S (IRGANOX) 565" (manufactured above by Basf Co., ltd.), ai Dike (ADEKA) manufactured by Addisosta waves (Adekstab) AO-20, AO-30, AO-40, AO-50, AO-60, AO-80, sumizer's Su Milai (Sumizer) BHT of Sumitomo chemical Co., ltd.), su Milai (Sumizer) BBM-S, su Milai (Sumizer) GA-80, and compounds having a structure represented by the following general formula.

[ 52]

In the general formulae (H-1) to (H-3), R ^H1 Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 2 to 10 carbon atoms, one of the groups-CH ₂ -or not more than two adjacent-CH ₂ Each independently substituted with-O-or-S-, and further, one or more hydrogen atoms present in the group may each independently be substituted with a fluorine atom or a chlorine atom. More specifically, it is preferably an alkyl group having 2 to 7 carbon atoms, an alkoxy group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms, and further preferably an alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

Of these, pentaerythritol tetrakis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ], octadecyl-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate and the compounds represented by the above general formulae (H-2) to (H-3) are particularly preferable.

The content of the antioxidant is preferably 0 mass% or more and 2.0 mass% or less, more preferably 0 mass% or more and 0.5 mass% or less, relative to 100 mass% of the total amount of the polymerizable compounds (MA) used in the polymer-dispersed liquid crystal composition of the present invention.

[ light stabilizer ]

The light stabilizer used in the present invention can be used to impart practical durability to the polymer dispersed liquid crystal element of the present invention. Examples of such a compound include: "Di-Nun (TINUVIN) 111FDL", "Di-Nun (TINUVIN) 123", "Di-Nun (TINUVIN) 144", "Di-Nun Binn (TINUVIN) 152", "Di-Nun Binn (TINUVIN) 292", "Di-Nun Binn (TINUVIN) 622", "Di-Nun Binn (TINUVIN) 770", "Di-Nun Binn (TINUVIN) 780", "Di-Nun Binn (TINUVIN) 905", "Di-Nun Binn (TINUVIN) 5100", "Di-Nun Binn (TINUVIN) 5050", "Di-Nun (TINUVIN) 5060", "Di-Nun Binn (TINUVIN) 5151", "Di-Nun (CHIMASORB) 119FL", "Di-Nun (CHIMASSB) FL", "Di-Ke-Ten (CHIMASSB) Usb) (CHIMASSB) upper limit (LALA) 62", "Di-Katsumab", "AdNei-Katsumab (AdNei-Katsumab) 62", "Di-Katsumada (Adtsumada) 62, etc.

The amount of the ultraviolet absorber to be added is preferably 0.0 mass% or more and 2.0 mass% or less, more preferably 0.0 mass% or more and 1.0 mass% or less, relative to the total amount of the polymerizable compound (MA) used in the polymer dispersed liquid crystal composition of the present invention.

[ chain transfer agent ]

The chain transfer agent used in the present invention can be used to further improve the adhesion between the polymer dispersed liquid crystal composition and the substrate. Examples of the chain transfer agent include: thiol compounds such as octylthiol, N-butylthiol, N-pentylmercaptan, N-hexadecylthiol, N-tetradecylthiol, N-dodecylthiol, t-tetradecylthiol, t-dodecylthiol, etc., thiol compounds such as hexanedithiol, decanedithiol, 1, 4-butanediol dithiopropionate, 1, 4-butanediol dithioglycolate, ethylene glycol dithiopropionate, trimethylolpropane trithioglycolate, trimethylolpropane trithiopropionate, trimethylolpropane tris (3-mercaptobutyrate), pentaerythritol tetrathioglycolate, pentaerythritol tetrathiopropionate, trimercapto-tris (2-hydroxyethyl) isocyanurate, 1, 4-dimethylmercaptobenzene, 2,4, 6-trimercapto-s-triazine, thiol compounds such as 2- (N, N-dibutylamino) -4, 6-dimercapto-s-triazine, etc., pentacene, alpha-methylstyrene dimer, acrolein, allyl, terpinolene, alpha-terpene, gamma-terpene, dipentene, etc.,

Specifically, compounds represented by the following general formulae (9-1) to (9-8), α -methylstyrene dimer, and α -terpinene are preferable.

[ 53]

Wherein R is ⁹⁵ An alkyl group having 2 to 18 carbon atoms, wherein the alkyl group may be a straight chain or a branched chain, and wherein at least one methylene group in the alkyl group may be substituted with an oxygen atom, a sulfur atom, -CO-, -OCO-, -COO-or-CH=CH-in such a manner that the oxygen atom and the sulfur atom are not directly bonded to each other, and R ⁹⁶ And represents an alkylene group having 2 to 18 carbon atoms, wherein at least one methylene group in the alkylene group may be substituted with an oxygen atom, a sulfur atom, -CO-, -OCO-, -COO-or-ch=ch-in such a manner that the oxygen atom and the sulfur atom are not directly bonded to each other.

The content of the chain transfer agent is preferably 0.0 mass% or more and 10 mass% or less, more preferably 0.0 mass% or more and 5.0 mass% or less, relative to 100 mass% of the total amount of the polymerizable compounds (MA) used in the polymerizable composition of the polymer-dispersed liquid crystal composition of the present invention.

[ pigment ]

The pigment used in the present invention can be used to impart color to the polymer dispersed liquid crystal element of the present invention or to control color. The coloring matter is not particularly limited, and any known and conventional coloring matter can be used in a range of being soluble in liquid crystal or dispersed in a polymer network. Examples of the dye include a dichromatic dye and a fluorescent dye. Examples of such pigments include: the azo dye, anthraquinone dye, quinacridone dye, dioxazine dye, quinophthalone dye, cyanine dye, phthalocyanine dye, perylene dye, viol dye, squaraine dye, and the like are preferably those showing liquid crystallinity from the viewpoint of addition. Examples include: japanese patent application laid-open No. 51-2885, japanese patent application laid-open No. 61-21163, japanese patent application laid-open No. 62-555, japanese patent application laid-open No. 63-301850, japanese patent application laid-open No. 7-48520, japanese patent application laid-open No. 7-179858, japanese patent application laid-open No. 10-279945, japanese patent application laid-open No. 11-172252, japanese patent application laid-open No. 2000-239664, japanese patent application laid-open No. 2012-82400, and the like Japanese patent application laid-open No. 59-20355, japanese patent application laid-open No. 59-172549, japanese patent application laid-open No. 61-148291, japanese patent application laid-open No. 1-161086, japanese patent application laid-open No. 8-67822, etc., anthraquinone pigments shown in Japanese patent application laid-open No. 59-51947, japanese patent application laid-open No. 61-148292, etc., quinophthalone pigments shown in Japanese patent application laid-open No. 2000-44825, japanese patent application laid-open No. 2001-49135, etc. The content of the coloring matter is preferably 0 mass% or more and 8 mass% or less, more preferably 0 mass% or more and 4 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal compounds (LB) used in the polymer-dispersed liquid crystal composition of the present invention.

[ pigment ]

The pigment used in the present invention can be used to impart color or control color to the polymerizable liquid crystal element of the present invention. The coloring matter is not particularly limited, and any known and conventional coloring matter can be used in a range of being dispersed in a liquid crystal or a network polymer. Examples of such pigments include: azo pigments, diketopyrrolopyrrole pigments, quinacridone pigments, dioxazine pigments, perylene pigments, phthalocyanine pigments, carbon black pigments and the like are preferable to be excellent in dispersibility in the network polymer from the viewpoint of effectively imparting colorability. The content of the pigment is preferably 0 mass% or more and 8 mass% or less, more preferably 0 mass% or more and 4 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal compounds (LB) used in the polymer-dispersed liquid crystal composition of the present invention.

[ particles having a particle diameter of less than 1 μm ]

The particles having a particle diameter of less than 1 μm used in the present invention can be used to impart various functions to the polymer dispersed liquid crystal element of the present invention. The particles are not particularly limited, and may be used in a range that does not impair the electro-optical properties or adhesion of the liquid crystal element. Examples of such particles include: inorganic fillers such as alumina, titanium white, titanium black, aluminum hydroxide, talc, clay, mica, barium titanate, zinc oxide, and glass fiber, metal powders such as silver powder and copper powder, and thermally conductive fillers such as aluminum nitride, boron nitride, silicon nitride, gallium nitride, silicon carbide, magnesium oxide (aluminum oxide), silica, crystalline silica (silicon oxide), fused silica (silicon oxide), graphite, and carbon fiber containing carbon nanofibers, silver nanoparticles, quantum Dots (QD) emitter particles, and perovskite type emitter particles.

The particles are preferably particles having good dispersibility in the network polymer. The content of the particles is preferably 0 mass% or more and 5 mass% or less, more preferably 0 mass% or more and 3 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal compounds (LB) used in the polymer-dispersed liquid crystal composition of the present invention.

[ chiral Compounds ]

The chiral compound used in the present invention can be used to impart various functions to the polymer dispersed liquid crystal element of the present invention. The chiral compound is not particularly limited, and may be used in a range that does not impair the electro-optical properties or adhesion of the liquid crystal element. Specifically, examples thereof include: cholesterol nonanoate having a cholesterol group as a chiral group, cholesterol stearate, BDH company having a 2-methylbutyl group as a chiral group, "CB-15", "C-15", merck (Merck) company, "S-1082", chisso (Chisso) company, "CM-19", "CM-20", "CM", 1-methylheptyl group as a chiral group, "S-811" by Merck (Merck) company, "CM-21", "CM-22" by Chisso (Chisso) company, basoff (BASF) company "LC756" having an isosorbide (isosorbide) skeleton as a chiral group, japanese patent application laid-open No. 2009-515818, japanese patent application laid-open No. 2010-90108, japanese patent application laid-open No. 2013-87109, and the like.

When the chiral compound is contained, the amount of the value (d/P) obtained by dividing the thickness (d) of the polymer obtained by addition by the helical pitch (P) in the polymer is preferably in the range of 0.1 to 100, more preferably in the range of 0.1 to 20, depending on the use of the polymer dispersed liquid crystal composition of the present invention.

In order to exert the characteristics of the liquid crystal composition, the chiral compound is preferably contained in an amount as small as possible to obtain a desired helical pitch. The chiral compound content is preferably 0 mass% or more and 8 mass% or less, more preferably 0 mass% or more and 4 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal compounds (LB) used in the polymer-dispersed liquid crystal composition of the present invention.

[ oriented Material ]

The polymer dispersed liquid crystal composition of the present invention may contain an alignment material in order to control the alignment of the liquid crystal element. The alignment material used in the present invention is a known and conventional alignment material insofar as it is insoluble in the liquid crystal composition. Examples of such an orientation material include: a polymerizable compound having a polar group at one end of a mesogenic skeleton and a long-chain alkyl group at the other end, a polymerizable liquid crystal compound having a polar group at a lateral position (lateral position) of a mesogenic skeleton, a polymerizable compound having a plurality of mesogenic skeletons and a polar group at a side chain of a long-chain alkyl group bonding one of the mesogenic skeletons to the mesogenic skeleton, or the like.

< liquid Crystal element >)

The liquid crystal element using the polymer dispersed liquid crystal composition of the present invention includes at least a layer (phase separation liquid crystal layer) in which liquid crystal phase separates from a network polymer, an electrode, and a substrate. Or comprises a phase separation liquid crystal layer, an alignment film phase, an electrode, and a substrate for supporting the phase separation liquid crystal layer, the alignment film phase, and the electrode.

The phase separated liquid crystal phase is obtained by: the polymer network derived from each polymerizable component contained in the polymerizable compound (MA) is formed by polymerizing the polymerizable compound (MA) contained in the polymer dispersed liquid crystal composition.

The liquid crystal element of the present invention can be brought into a light scattering state by a network structure based on a polymer and liquid crystal molecules existing in voids thereof, for example, when no voltage is applied. On the other hand, when a voltage is applied, the liquid crystal molecules are aligned perpendicularly to the substrate, and thus the liquid crystal display device can be in a transparent state. As described above, the liquid crystal element of the present invention changes the light transmission state according to the presence or absence of an applied voltage, and is therefore useful as a liquid crystal light control element used for a device requiring a light control function or a liquid crystal display element used for a display for image display.

The liquid crystal element of the present invention may be configured to control the alignment of liquid crystal molecules by applying a voltage, but is preferably configured as a vertical electric field type liquid crystal element. A vertical electric field type liquid crystal element is a liquid crystal element in which electrodes are arranged so as to generate an electric field perpendicular to an alignment film. In a vertical electric field type liquid crystal element, electrodes are generally provided on both of two transparent substrates sandwiching a phase separation liquid crystal layer.

The structure of the vertical electric field type liquid crystal element of the present invention comprises: each of the liquid crystal display device includes a first substrate and a second substrate each including a transparent electrode (layer) made of a transparent conductive material, and a phase separation liquid crystal layer sandwiched between the first substrate and the second substrate. The phase separation liquid crystal layer includes a polymer dispersed liquid crystal material containing liquid crystal molecules and a polymer component contained in the liquid crystal composition.

[ substrate ]

The substrate used in the liquid crystal device of the present invention is a substrate commonly used in a liquid crystal display device, an organic light emitting display device, other display devices, optical parts, a light adjusting device, a colorant, a mark, a printed matter, or an optical film, and is not particularly limited as long as it is a material having practical transparency and is suitable for applications in which tolerable heat resistance or transmittance is important in a temperature range of heating and use in the manufacturing process of the liquid crystal device.

Examples of such a substrate include: organic materials such as glass substrates, metal substrates, ceramic substrates, plastic substrates, and papers. In particular, when the base material is an organic material, there can be mentioned: cellulose derivatives, polyolefins, polyesters, polyolefins, polycarbonates, polyacrylates, polyarylates, polyethersulfones, polyimides, polyphenylene sulfides, polyphenylene oxides, nylons or polystyrenes, and the like. Among them, a plastic substrate such as polyester, polystyrene, polyolefin, cellulose derivative, polyarylate, polycarbonate, polyimide, or the like is preferably used.

In the case of having two substrates, one of the substrates may have transparency which is practical as a liquid crystal element, and the other substrate may not have transparency.

The shape of the substrate is a flat plate, but may be other shapes such as a curved shape. The substrate may have an electrode layer, an antireflection function, and a reflection function as needed.

In order to improve the adhesion of the liquid crystal element of the present invention, the surface treatment of these substrates may be performed. As the surface treatment, there may be mentioned: ozone treatment, plasma treatment, corona discharge treatment, silane coupling treatment, and the like. In order to adjust the transmittance or reflectance of light, an organic thin film, an inorganic oxide thin film, a metal thin film, or the like may be provided on the surface of the substrate by a method such as vapor deposition, or the substrate may be a pickup lens, a rod lens, an optical disk, a retardation film, a light diffusion film, a microlens sheet, a color filter, or the like in order to impart an optical added value.

[ electrode: transparent electrode layer

The electrode used in the liquid crystal element of the present invention is provided so as to generate an electric field in the liquid crystal element that can control the alignment of liquid crystal molecules in the phase separation liquid crystal layer. The electric field strength is controlled according to the degree to which a voltage is applied to the electrodes.

The shape of the electrode is not particularly limited, and the conductive portion may be stripe-shaped, mesh-shaped, or random mesh-shaped.

The electrode material is preferably a metal material, and specifically Al, cu, au, ag, cr, ta, ti, mo, W, ni or an alloy containing at least one of these is preferably Al or an alloy containing Al.

In order to improve the transparency of the liquid crystal element, the electrode is preferably constituted by the transparent electrode layer 2. Such a transparent electrode layer may include a known transparent conductive material such as Indium Tin Oxide (ITO), indium zinc Oxide (Indium Zinc Oxide, IZO), and Indium zinc Tin Oxide (Indium Zinc Tin Oxide, IZTO). In the case where one of the substrates contains a material that does not have transparency, the electrode provided on the substrate that does not have transparency is not required to have transparency, and may be appropriately selected from known metal materials.

[ alignment film layer ]

The substrate may be subjected to an alignment treatment so that the liquid crystal molecules in the polymer dispersed liquid crystal element of the present invention are aligned horizontally or vertically, or an alignment film may be provided. As the orientation treatment, there may be mentioned: extension treatment, rubbing treatment, polarized ultraviolet visible light irradiation treatment, ion beam treatment, siO ₂ Oblique vapor deposition treatment on a substrate, and the like. As such an orientation film, there may be mentioned: polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyethersulfone, epoxy resin, epoxyacrylate resin, acrylic resin, azo compound, coumarin compound, chalcone compound, cinnamate compound, fulgide (fulgide) compound, anthraquinone compound, azo compound, arylvinyl compound, or the like, or a polymer or copolymer of the compounds. In order to impart an inclination angle to the liquid crystal molecules, in the case of performing a rubbing treatment, the compound to be subjected to an alignment treatment by rubbing is preferably a compound that promotes crystallization of a material by adding a heating step to the alignment treatment or after the alignment treatment. Among the compounds subjected to the alignment treatment other than rubbing, a photo-alignment material is preferably used.

In general, when a liquid crystal composition is brought into contact with a substrate having an alignment function, liquid crystal molecules are aligned in the vicinity of the substrate in a direction in which the substrate is subjected to an alignment treatment. The alignment treatment method for the substrate has a great influence on whether the liquid crystal molecules are aligned horizontally or obliquely or vertically with respect to the substrate.

[ example of method for manufacturing liquid Crystal element ]

In view of productivity, the liquid crystal element of the present invention is preferably produced by laminating a counter substrate with a polymer dispersed liquid crystal composition by, for example, a roll-to-roll method, and dropping or applying the polymer dispersed liquid crystal composition onto a substrate by, for example, a Drop Fill (ODF) method.

In the step of manufacturing the liquid crystal composition by a roll-to-roll method, the polymer dispersed liquid crystal composition is coated on a first electrode, or a glass substrate having an alignment film and a first electrode, or a plastic substrate, and the second electrode, or the glass substrate having an alignment film and a second electrode, or the electrode side of the plastic substrate, or the alignment film side is bonded to the liquid crystal composition so as to have a uniform thickness, whereby the liquid crystal element can be manufactured. Examples of the method for applying the polymer-dispersed liquid crystal composition used in the present invention include known and customary methods such as an applicator method, a bar coating method, a roll coating method, a direct gravure coating method, a reverse gravure coating method, an ink jet method, a die coating method, and a cover coating method (cap coating method). In the step of manufacturing the liquid crystal element according to the ODF method, the liquid crystal element can be manufactured by drawing a sealing agent such as an epoxy photo-thermal curing agent in a closed-loop bank shape on either one of a back plate and a front plate of a hollow element using a dispenser, dropping a predetermined amount of the liquid crystal composition therein under deaeration, and then bonding the front plate to the back plate.

The liquid crystal element of the present invention can be manufactured from a liquid crystal element by interposing a spacer for holding a space between two substrates, as in the case of the known liquid crystal element. The thickness between the substrates, that is, the thickness of the phase separation layer is preferably 2 μm to 50 μm, more preferably 10 μm to 30 μm. The spacers may be dispersed on the substrate in advance, or may be mixed in the polymer dispersed liquid crystal composition in advance and applied on the substrate simultaneously with the polymer dispersed liquid crystal composition.

The method of sandwiching the polymer dispersed liquid crystal composition between two substrates may be a usual vacuum injection method, but is preferably carried out by dropping or coating by ODF method or the like. The polymer dispersed liquid crystal composition is preferably in a uniform isotropic (isotropic) state during the period from the dropping or coating to the polymerization of the polymerizable composition.

In the case of dropping or coating, a method of sandwiching the polymer dispersed liquid crystal composition between two substrates may be performed by a method of sandwiching the two substrates with a laminator or the like.

The polymer dispersed liquid crystal composition of the present invention can be used as a composition in which particles for determining the thickness of a liquid crystal element are mixed, and the composition can be held between hollow elements. As such particles, known and conventional glass particles or polymer particles used in a general liquid crystal display element or liquid crystal display can be used.

In this case, the following method is preferable: a method in which the polymer-dispersed liquid crystal composition and a composition containing particles for determining the thickness of the liquid crystal element are coated on a plastic substrate containing a first electrode, and then the plastic substrate containing a second electrode is bonded so that the first electrode and the second electrode face each other, and then ultraviolet light is immediately irradiated; a method of irradiating ultraviolet rays in a state where pressure is applied to the first plastic base material and the second plastic base material; or a method in which a liquid crystal composition for a liquid crystal element and a composition containing particles for determining the thickness of the liquid crystal element are applied onto a first plastic substrate containing a first electrode, the first plastic substrate and the applied liquid crystal composition are brought into a vacuum state, and a second plastic substrate containing a second electrode is bonded to face the first electrode and the second electrode in a vacuum state, and ultraviolet rays are irradiated.

[ polymerization Process ]

As a method for polymerizing the polymer dispersed liquid crystal composition of the present invention, ultraviolet irradiation is suitable. As the lamp that generates ultraviolet light, a metal halide lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, or the like can be used. The wavelength of the ultraviolet light to be irradiated is preferably ultraviolet light in a wavelength region which is an absorption wavelength region of a photopolymerization initiator contained in the polymer dispersed liquid crystal composition and is not an absorption wavelength region of the contained liquid crystal composition, and specifically, ultraviolet light having a wavelength of 330nm or less is preferably used by using a metal halide lamp, a high pressure mercury lamp, or an extra-high pressure mercury lamp. In addition, it is also preferable to use an Ultraviolet (UV) -light emitting diode (Light Emitting Diode, LED) lamp that can radiate a single wavelength.

The intensity of the irradiated ultraviolet rays can be suitably adjusted to obtain a target light adjusting layer, preferably 1mw/cm ² ～200mw/cm ² More preferably 5mw/cm ² ～50mw/cm ² . The time for irradiation of ultraviolet rays is appropriately selected depending on the intensity of the ultraviolet rays to be irradiated, but is preferably 10 seconds to 300 seconds.

The temperature at the time of ultraviolet irradiation is an important factor for determining the characteristics of the light control layer, but is preferably a temperature higher than the isotropic-nematic transition point (Tnm) of the polymer dispersed liquid crystal composition.

The liquid crystal element of the present invention may be used as it is or may be applied to other substrates. In addition, an adhesive or an adhesive layer, a protective film, a polarizing film, or the like may be laminated.

[ other electric fields ]

The liquid crystal element of the present invention may employ a transverse electric field type or other electric field type in addition to the vertical electric field type. Fringe fields used for fringe field switching (Fringe Field Switching, FFS) drive modes can also be used. In that case, a horizontally oriented layer may also be provided. The horizontally oriented layer may comprise known materials.

The liquid crystal element of the present invention is preferably used for a light control unit in a building material, a light control glass, a smart window for a vehicle, an organic light emitting diode (Organic Light Emitting Diode, OLED) display, or the like, for example. The liquid crystal display element of the present invention can be used for the same applications as those of conventional polymer dispersed liquid crystal display elements, and in particular, can be preferably used for transmissive displays, flexible displays, and the like. More specifically, the present invention is applicable to articles such as architectural light control elements for windows, skylights, roofs, walls, partition walls, door leaves, transportation light control elements for doors, windows, doors, helmets, sliding roofs, decorative light control elements for sunglasses, eyeglasses, sun visors, watches, mirrors, reflection plates, flexible liquid crystal display elements, reflective liquid crystal display elements, transparent liquid crystal display elements, and display members such as variable diffusion films.

< light modulation element >)

The light modulation element of the invention has a pair of transparent electrode substrates; and a composite layer disposed between the pair of transparent electrode substrates and comprising a polymer network and a liquid crystal compound. The polymer network is derived from a polymerizable compound (MA) contained in the polymer-dispersed liquid crystal composition, and the liquid crystal compound is a non-polymerizable liquid crystal compound (LB) contained in the polymer-dispersed liquid crystal composition.

The light control element may be an element that uses the liquid crystal element using the polymer dispersed liquid crystal composition and electrically controls the transmittance of light of the liquid crystal element. The light control element may be formed by attaching only the voltage applying device to the liquid crystal element, but may be formed by laminating a glass sheet with an intermediate film such as polyvinyl butyral (Polyvinyl Butyral, PVB), ethylene vinyl acetate copolymer resin (Ethyl Vinyl Acetate, EVA), thermoplastic urethane (Thermoplastic Urethanes, TPU) (polyurethane system), or an ionic intermediate film (SGP) interposed therebetween, and sandwiching the liquid crystal element between two glass sheets. Further, a functional film such as ultraviolet ray blocking and heat ray blocking may be added.

Examples

The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. In the following examples and comparative examples, "parts" in the compositions means "parts by weight".

Table 1 shows the non-polymerizable liquid crystal compounds (LB) used in examples and comparative examples described below. Table 2 shows the components of the polymerizable compound (MA) used in examples and comparative examples described later.

TABLE 1

*1 the third component and the sixth component add up to 100 parts by weight

The following shows the meanings of symbols showing the structures of the respective liquid crystal compounds in table 1. In table 1, "1", "2", "3" and "4" at the end of each component refer to the number of carbon atoms in the side chain.

[ 54]

TABLE 2

Synthesis example 1

44.4 parts (0.2 mol) of isophorone diisocyanate (Isophorone Diisocyanate, IPDI) was charged into a flask equipped with stirring blades, and while stirring, 810 parts (0.1 mol) of polypropylene glycol (average molecular weight Mw: 8100) was charged while taking care of heat generation, and the temperature was raised to 70 ℃. The reaction was carried out at the above temperature for 7 hours to obtain a urethane polymer having an isocyanate group at the terminal. Then, 23.2 parts (0.2 mol) of 2-hydroxyethyl acrylate (molecular weight 116) was charged, and the reaction was further carried out at the above temperature for 7 hours. After confirming the disappearance of NCO absorption by infrared absorption spectrum, the resultant was taken out to obtain urethane acrylate UA-1 (average molecular weight Mw: 29800).

In the present invention, the number average molecular weight (Mn) and the weight average molecular weight (Mw) are values obtained by measuring by gel permeation chromatography (Gel Permeation Chromatography, GPC) and converting them into polystyrene. The measurement conditions of GPC are as follows.

[ measurement conditions of GPC ]

Measurement device: HLC-8320GPC manufactured by Tosoh Co., ltd "

And (3) pipe column: protective column "Su Bo (Super) HZ-L" manufactured by Tosoh Co., ltd., "Su Bo (Super) HZ2000" x 3 "manufactured by Tosoh Co., ltd.," T Su Bo (TSuper) HZM-M "manufactured by Tosoh Co., ltd.,"

A detector: built-in Refractive Index (RI) detector

And (3) data processing: "Aikesk (EcoSEC) -WorkStation (workbench) Ver2.01" manufactured by Tosoh Co., ltd "

Measurement conditions: column temperature 40 ℃, developing solvent tetrahydrofuran, flow rate 1.0 ml/min

Standard: according to the apparatus measurement manual, monodisperse polystyrene of known molecular weight is used.

Example 1

The polymerizable compound MA-1 was obtained as the polymerizable compound (MA) of the present invention by mixing 20 parts by weight of UA-1 produced in Synthesis example 1 as the first component, 30 parts by weight of APG-700 as the fourth component, 35 parts by weight of ACMO as the second component, and 15 parts by weight of ISTA as the fifth component, and further adding 0.1 part by weight of additive P-2M and 0.651 parts by weight of Irg.651 as the polymerization initiator, and dissolving them while stirring at 50 ℃. In addition, a non-polymerizable liquid crystal compound lb-1 was prepared, which contained 100 parts by weight of the liquid crystal composition LC1 shown in table 1. The main physical properties of the non-polymerizable liquid crystal compound lb-1 are shown in Table 3.

To the obtained polymerizable compound mA-1, a non-polymerizable liquid crystal compound LB-1 was added so that the weight ratio of the polymerizable compound (mA)/the non-polymerizable liquid crystal compound (LB) (mA/LB weight ratio) became 56/44, and the mixture was dissolved while stirring at 50 ℃.

After the obtained polymer-dispersed liquid crystal composition PL1 was poured into a glass tank (structure of glass substrate/transparent electrode layer/air layer/transparent electrode layer/glass substrate) having a thickness of 15 μm at room temperature, ultraviolet rays were irradiated at room temperature, thereby obtaining a liquid crystal polymer composite. The ultraviolet light is provided by a UV-LED lamp with an intensity of 10mW/cm ² The time was 60 seconds.

(haze evaluation)

Electrode wiring was attached to a liquid crystal element having the obtained liquid crystal polymer composite, and voltage-haze characteristics were evaluated using a haze meter (NDH-7000 manufactured by japan electric color industry co.). The Haze when no voltage was applied (Haze when turned OFF (OFF Haze)) was 98.3%, and the Haze when alternating current (Alternating Current, AC) was applied at 100V (Haze when turned ON (ON Haze)) was 2.3%. The results are shown in Table 3.

(evaluation of transmittance)

The liquid crystal element having the obtained liquid crystal polymer composite was evaluated by applying a voltage of 0V to 100V using LCD-5200 (manufactured by tsukamu electronics corporation), defining the transmittance at the time of light shielding as 0%, defining the transmittance at the time of no light shielding as 100%, defining the transmittance in the 0V state as T0, and defining the transmittance at the time of AC 100V application as T100. The respective transmittance was 1.12% and 85.1% at 25 ℃.

(evaluation of drive Voltage)

Using a liquid crystal element having the obtained liquid crystal polymer composite, when the transmittance (T0) at 0V state at 25 ℃ and-20 ℃ was set to 0% transmittance and the transmittance (T100) at 100V was set to 100% transmittance, the voltage at which the transmittance reached 90% was defined as the driving voltage (V90) and was evaluated. The respective driving voltages were 45.2V and 56.8V.

(evaluation of adhesion)

The adhesion was evaluated by the following method. First, glass beads having a particle diameter of 15 μm were spread on the transparent electrode surfaces of a PET film with a protective film and a PET film with a transparent electrode, and the liquid crystal composition was dropped thereon and applied with an applicator. Then, the transparent electrode surface of the PET film on the coated surface was bonded to the coated surface, and pressure was uniformly applied to the entire surfaces of the upper and lower PET films, and the film laminate thus obtained was irradiated with ultraviolet rays at room temperature, thereby obtaining a polymer dispersed liquid crystal element. The polymer-dispersed liquid crystal element obtained was cut out with a cutter so that the width became 1 cm. At this time, there was no exudation of the liquid crystal. 180 DEG peeling test was performed using the polymer dispersed liquid crystal element thus cut. The adhesion evaluation was performed using a force gauge (force tester) MCT2150 manufactured by a & D company, and the maximum strength was obtained when the PET film with the transparent electrode was peeled off in the 180 ° direction under an environment where the width of the sample was 10mm, the stretching speed was 50 mm/min, and the temperature was 25 ℃. The intensity was 0.4N/cm.

(examples 2 to 6, comparative examples 1 to 4)

Polymer dispersed liquid crystal compositions PL2 to PL6 and polymer dispersed liquid crystal compositions cPL1 to cPL4 of examples 2 to 6 and comparative examples 1 to 4 were obtained in the same manner as in example 1, except that the components were used in the blending ratios shown in Table 3 and Table 4.

Using the obtained polymer-dispersed liquid crystal compositions PL2 to PL6 and cPL1 to cPL4, polymer-dispersed liquid crystal elements were obtained in the same manner as in example 1.

Using the obtained polymer dispersed liquid crystal element, each evaluation was performed in the same manner as in example 1. The results are shown in tables 3 and 4.

TABLE 3

*2 parts by weight of the first component, the second component, the fourth component, and the fifth component in total of 100 parts by weight

*3 parts by weight relative to 100 parts by weight of the total of the first component, the second component, the fourth component and the fifth component

*4 LB/MA weight ratio = non-polymerizable liquid Crystal Compound (LB)/polymerizable Compound (MA)

TABLE 4

*4 LB/MA weight ratio = non-polymerizable liquid crystalline compound (LB)/polymerizable compound (MA).

Claims

1. A polymer-dispersed liquid crystal composition comprising a polymerizable compound (MA) and a non-polymerizable liquid crystal compound (LB),

[ chemical 1]

P ⁱⁱⁱ¹ -Z ⁱⁱⁱ¹ -A ⁱⁱⁱ¹ (ii)

A ⁱⁱⁱ¹ represents general formula (ii-1) to general formula (ii-20),

[ chemical 2]

(wherein, more than one-CH ₂ -can be independently passed through-O-, -S-, -COO-, -OCO-, -NH-, -NCH ₃ -or-CO-substitution, wherein in the case where two or more oxygen atoms and/or sulfur atoms are present in total in the general formulae (ii-1) to (ii-20), these are not bonded to each other as in-O-O-, -O-S-or-S-S-, and in addition, one or more-CH ₂ -CH ₂ -may be substituted with-ch=ch-group, and in addition, the hydrogen atom in the general formulae (ii-1) to (ii-20) may be substituted with an alkyl group having 1 to 8 carbon atoms, one or more of the alkyl groups being not adjacent-CH ₂ Respectively in such a way that the oxygen atoms are not directly adjacentIndependently through-O-, -CO-, -COO-or-OCO-substitution; in addition, the black dots in the formula represent the direction Z ⁱⁱⁱ¹ Bond of (c)

The non-polymerizable liquid crystal compound (LB) contains one or more of the diphenylacetylene compounds represented by the following general formula (iii) as a second component,

[ chemical 3]

R ¹² represents fluorine atom, chlorine atom, cyano group, CF ₃ Radical, OCF ₃ Radical, OCHF ₂ A group, NCS group or C1-10 alkyl group, one or both of which are not adjacent CH ₂ The group may be substituted with an oxygen atom, -COO-, -OCO-, and in addition, one or more methylene groups may be substituted with-CH=CH-or-C≡C-, preferably a fluorine atom, a cyano group or an alkyl group having 1 to 5 carbon atoms (one or two of the non-adjacent CH groups in the alkyl group) ₂ The radicals may be substituted by oxygen atoms, in addition, more than one methylene group may be substituted by-CH=CH-or-CH≡CH-,

[ chemical 4]

A kind of electronic device with high-pressure air-conditioning system

Each independently of the other is

[ chemical 5]

Or is a

[ chemical 6]

In addition, in the case of the optical fiber,

[ chemical 7]

Can be as follows

[ chemical 8]

Z ¹¹ Z is as follows ¹² One of them is-C.ident.C-, the other, when present, is-C.ident.C-, -CF ₂ O-、-OCF ₂ -, trans-ch=ch-, trans-cf=cf-, -COO-, -CH ₂ -CH ₂ -、-CF ₂ -CF ₂ -or a single bond, n is 0 or 1).

2. The polymer-dispersed liquid crystal composition according to claim 1, comprising

[ chemical 9]

Is that

[ chemical 10]

As the compound represented by the general formula (iii) according to claim 1.

3. The polymer-dispersed liquid crystal composition according to claim 1 or 2, comprising

[ chemical 11]

A kind of electronic device with high-pressure air-conditioning system

At least one of (a) is

[ chemical 12]

As the compound represented by the general formula (iii) according to claim 1.

4. The polymer dispersed liquid crystal composition according to any one of claims 1 to 3, wherein the polymerizable compound (MA) contains one or two or more polyfunctional (meth) acrylate oligomer compounds having a weight average molecular weight of 2000 or more as a third component.

5. The polymer-dispersed liquid crystal composition according to any one of claims 1 to 4, wherein a weight ratio (LB/MA) of the non-polymerizable liquid crystal compound (LB) to the polymerizable compound (MA) in the polymer-dispersed liquid crystal composition is in a range of 30/70 to 70/30.

6. The polymer-dispersed liquid crystal composition according to any one of claims 1 to 5, wherein the polymerizable compound (MA) further comprises, as a fourth component, one or more selected from the group consisting of a polyfunctional polymerizable oligomer and a polyfunctional polymerizable monomer having a weight average molecular weight of less than 2000 represented by the following general formula (iv),

[ chemical 13]

(wherein Y is ³¹ Represents a hydrogen atom or a methyl group,

n ³¹ an integer of 2 to 6).

7. The polymer-dispersed liquid crystal composition according to any one of claims 1 to 6, wherein the polymerizable compound (MA) further comprises one or more chain-like monofunctional polymerizable compounds represented by the following general formula (v) as a fifth component,

[ chemical 14]

p ^iia1 -R ^iia2 (v)

R ^iia2 represents a linear or branched alkyl group having 1 to 22 carbon atoms, one or more of which are-CH ₂ -each independently substituted by-O-, -CO-, -COO-, or-OCO-in such a way that the oxygen atoms are not directly adjacent, and one or more hydrogen atoms present in the alkyl group may each independently be substituted by a fluorine atom or-OH).

8. The polymer-dispersed liquid crystal composition according to claim 4, wherein the third component is one or more selected from the group consisting of urethane-based (meth) acrylate oligomers and polyester-based (meth) acrylate oligomers.

9. The polymer-dispersed liquid crystal composition according to any one of claims 1 to 8, wherein the non-polymerizable liquid crystal compound (LB) further contains one or more compounds represented by the following general formula (vi) as a sixth component,

[ 15]

ring A ⁶ Represents 1, 4-phenylene, 1, 4-cyclohexylene, 1, 3-dioxane-2, 5-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, the 1, 4-phenylene being capable of being unsubstituted or having one or more fluorine atoms, chlorine atoms, CF ₃ 、OCF ₃ Or a methyl group as a substituent,

ring A ⁷ Represents 1, 4-phenylene or 1, 4-cyclohexylene, the 1, 4-phenylene being capable of being unsubstituted or having one or more fluorine atoms, chlorine atoms, CF ₃ 、OCF ₃ Or a methyl group as a substituent,

ring A ⁸ Represents 1, 4-phenylene, which 1, 4-phenylene can be unsubstituted or has one or more fluorine atoms, chlorine atoms, CF ₃ 、OCF ₃ Or a methyl group as a substituent,

n represents 0 or 1; wherein the second component is excluded).

10. According to claim 9Wherein in the general formula (vi), ring A ⁷ Represents a 1, 4-phenylene group, said 1, 4-phenylene group having one fluorine atom as a substituent.

11. The polymer-dispersed liquid crystal composition according to claim 6, wherein the fourth component is a compound represented by the following general formula (iv-1),

[ 16]

(wherein Y is ¹ Y and Y ² Represents a hydrogen atom or a methyl group,

X ¹ represents a straight-chain or branched alkylene group having 2 to 80 carbon atoms, any carbon atom of the alkylene group may be substituted by-O-, -CO-, -COO-, -OCO-, -ch=ch-, -c≡c-, or OH).

12. The polymer-dispersed liquid crystal composition according to any one of claims 1 to 11, wherein the polymerizable compound (MA) further contains an additive represented by the following general formula (X),

[ chemical 17]

(wherein Y is ³¹ Represents a hydrogen atom or a methyl group,

n ³¹ an integer of 1 to 6 is represented,

X ³¹ comprising a group represented by the following formula (X-1),

[ chemical 18]

13. The polymer dispersed liquid crystal composition according to any one of claims 1 to 12, further comprising a polymerization initiator.

14. The polymer-dispersed liquid crystal composition according to any one of claims 1 to 13, further comprising one or more selected from the group consisting of a polymerization inhibitor, an antioxidant, a light stabilizer, particles having a particle diameter of less than 1 μm, a pigment, and a pigment.

15. A liquid crystal cell using the polymer dispersed liquid crystal composition according to any one of claims 1 to 14.

16. A dimming element, comprising:

a pair of transparent electrode substrates; and

a composite layer disposed between the pair of transparent electrode substrates and comprising a polymer network and a liquid crystal compound,

in the light-adjusting element, the light-adjusting element is provided with a light-adjusting element,

the polymer network being derived from the polymerizable compound (MA) contained in the polymer dispersed liquid crystal composition according to any one of claims 1 to 14,

the liquid crystal compound is the non-polymerizable liquid crystal compound (LB) contained in the polymer dispersed liquid crystal composition according to any one of claims 1 to 14.