Patent Grant
11345857
The present invention relates to a spontaneous orientation aid for a liquid crystal composition, a liquid crystal composition, and a liquid crystal display element.
In related art, in a VA type liquid crystal display, a polyimide alignment film (PI) layer is provided on an electrode, in order to induce a vertical alignment of liquid crystal molecules, in a case where a voltage is not applied, and to realize a horizontal alignment of the liquid crystal molecules, in a case where a voltage is applied. However, the large cost is necessary for forming a PI layer, and accordingly, in recent years, a method for realizing alignment of liquid crystal molecules while omitting the PI layer is researched.
For example, PTL 1 discloses a liquid crystal medium including at least one kind of spontaneous alignment additives, on the basis of a mixture of polar compounds having negative dielectric anisotropy, and discloses that this liquid crystal medium is highly suitable for a use in a display not including an alignment layer at all. In PTL 1, a specific compound including a hydroxyl group is used as the spontaneous alignment additive.
PTL 1: JP-T-2014-524951
However, studies conducted by the inventors have revealed that when the spontaneous alignment additive disclosed in PTL 1 is used, the alignment regulating force for vertically aligning liquid crystal molecules is not sufficient and that the liquid crystal composition containing the spontaneous alignment additive has room for improvement in storage stability.
Therefore, an object of the invention is to provide a spontaneous orientation aid for a liquid crystal composition, which provides storage stability when added to a liquid crystal composition and allows vertical alignment of liquid crystal molecules without a PI layer. Another object of the invention is to provide a liquid crystal composition containing such a spontaneous orientation additive that provides excellent storage stability and allows vertical alignment of liquid crystal molecules without a PI layer, and to provide a liquid crystal display element produced using such a liquid crystal composition.
The invention provides a spontaneous orientation aid for a liquid crystal composition, including one or more compounds each having a mesogenic group substituted with: Pi1-Spi1-, wherein Pi1 represents a polymerizable group and represents a substituent selected from the group consisting of substituents represented by general formula (P-1) to general formula (P-15) in which each black point on a right end represents atomic bonding,
and Spi1 represents a spacer group; a monovalent organic group having a substituent represented by Ki1, wherein Ki1 represents a substituent represented by one of general formula (K-1) to general formula (K-11)); and Ri1 representing a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, a halogenated alkyl group, or Pi1-Spi1-, wherein —CH2— in the alkyl group may be replaced with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, or —OCO—, provided that —O— moieties are not bonded in series, wherein at least one Pi1-Spi1- is bonded to the mesogen from the lateral side with respect to the long axis of the mesogen.
In the formulae, WK1 represents a methine group, C—CH3, C—C2H5, or a nitrogen atom, XK1 and YK1 each independently represent —CH2—, an oxygen atom, or a sulfur atom, ZK1 represents an oxygen atom or a sulfur atom, UK1, VK1, and SK1 each independently represent a methine group or a nitrogen atom, exclusive of a combination of (K-5) and (K-6) forming apyridine ring, and each black point on the left end represents atomic bonding, provided that when Ki1 is (K-11), the mesogenic group includes one of —CH2—CH2COO—, —OCOCH2—CH2—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, and —OCH2CH2O—)
In addition, the invention further provides a liquid crystal composition having negative dielectric anisotropy (Δε) and including one or more compounds each having a partial structure defined for the spontaneous orientation aid for a liquid crystal composition.
The invention makes it possible to provide a liquid crystal composition containing a spontaneous orientation additive that provides excellent storage stability and allows vertical alignment of liquid crystal molecules without a PI layer, and to provide a liquid crystal display element produced using such a liquid crystal composition.
(Spontaneous Orientation Aid for Liquid Crystal Composition)
The spontaneous orientation aid for a liquid crystal composition according to the embodiment includes one or more compounds each having a mesogenic group substituted with: Pi1-Spi1-, wherein Pi1 represents a polymerizable group and represents a substituent selected from the group consisting of substituents represented by general formula (P-1) to general formula (P-15) in which a black point on the right end represents atomic bonding,
and Spi1 represents a spacer group; a monovalent organic group having a substituent represented by Ki1, wherein Ki1 represents a substituent represented by one of general formula (K-1) to general formula (K-11); and Ri1 representing a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, a halogenated alkyl group, or Pi1-Spi1-, wherein —CH2— in the alkyl group may be replaced with —CH═CH—, —C═C—, —O—, —NH—, —COO—, or —OCO—, provided that-O-moieties are not bonded in series, wherein at least one Pi1-Spi1- is bonded to the mesogen from the lateral side with respect to the long axis of the mesogen.
In the formulae, WK1 represents a methine group, C—CH3, C—C2H5, or a nitrogen atom, XK1 and YK1 each independently represent —CH2—, an oxygen atom, or a sulfur atom, ZK1 represents an oxygen atom or a sulfur atom, UK1, VK1, and SK1 each independently represent a methine group or a nitrogen atom, exclusive of a combination of (K-5) and (K-6) forming a pyridine ring, and each black point on the left end represents atomic bonding, provided that when Ki1 is (K-11), the mesogenic group contains one of —CH2—CH2COO—, —OCOCH2—CH2—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, and —OCH2CH2O—.
The mesogenic group has a partial structure represented by general formula (i):
In the formula, Zi1 represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —OOCO—, —CF2O—, —OCF2—, —CH═CHCOO—, —OCOCH═CH—, —CH2—CH2COO—, —OCOCH2—CH2—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, —OCH2CH2O—, or an alkylene group having 2 to 20 carbon atoms, one or two or more —CH2-'s not adjacent to each other in this alkylene group may be substituted with —O—, —COO—, or —OCO, provided that when Ki1 is (K-11), the mesogenic group includes one of —CH2—CH2COO—, —OCOCH2—CH2—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, and —OCH2CH2O—, Ai1 represents a divalent 6-membered ring aromatic group, a divalent 6-membered ring heteroaromatic group, a divalent 6-membered ring aliphatic group, or a divalent 6-membered ring heteroaliphatic group, hydrogen atoms in these ring structures may be substituted with a halogen atom, Pi1-Spi1-, a monovalent organic group having a substituent represented by general formula Ki1, or Ri1, provided that at least one is substituted with Pi1-Spi1- and when a plurality of Zi1's or Ai1's are present, these may be the same or different, mil represents an integer of 1 to 5. In the formula (i), the black point on the left end and the black point on the right end represent atomic bonding. The spontaneous orientation aid includes at least one compound having such a partial structure (hereinafter also referred to as the “compound (i)”).
The spontaneous orientation aid for a liquid crystal composition of the embodiment includes a compound having a partial structure represented by formula (i), particularly, a structure in which Ki1 in formula (i) is represented by any of formula (K-1) to formula (K-11). Thus, when used in a liquid crystal composition, the spontaneous orientation aid can adsorb to substrates sandwiching the liquid crystal composition (liquid crystal layer) and keep the liquid crystal molecules aligned in the vertical direction. Therefore, the spontaneous orientation aid for a liquid crystal composition of the embodiment makes it possible to vertically align the liquid crystal molecules without a PI layer (to induce vertical alignment of the liquid crystal molecules under no applied voltage and to achieve horizontal alignment of the liquid crystal molecules under an applied voltage). Thus, the compound (i) is suitable for use in aiding the spontaneous orientation of the liquid crystal molecules in the liquid crystal composition.
In addition, the inventors have found that the spontaneous orientation aid for a liquid crystal composition according to the embodiment, which includes the compound having a partial structure represented by formula (i), not only allows alignment of liquid crystal molecules but also provides storage stability for a liquid crystal composition. In a case where chemical stability is important for the spontaneous orientation aid, Ki1 is preferably (K-1), (K-3), (K-8), (K-9), (K-10), and (K-11), in a case where the liquid crystal alignment is important, Ki1 is preferably (K-1), (K-3), and (K-11), in a case where solubility to a liquid crystal compound is important, Ki1 is preferably (K-1), (K-8), and (K-10), and in a case where the balance between these is important, Ki1 is more preferably (K-1), (K-3), and (K-11). In addition, from viewpoints of chemical stability and polymerization sensitivity, Pi1 is preferably any substituent of formulae (P-1), (P-2), (P-7) to (P-10), and (P-12), and from a viewpoint of simple handling, Pi1 is more preferably formulae (P-1), (P-2), (P-9), and (P-10).
From the viewpoints described above, the compound in the spontaneous orientation aid for a liquid crystal composition according to the embodiment may have a partial structure represented by formula (i) at a terminal of the molecule, preferably a terminal of the main chain of the molecule, and the chemical structure of a portion to be bonded to the partial structure represented by formula (i) is not particularly limited, as long as the function of the liquid crystal composition is not inhibited. The compound in the spontaneous orientation aid for a liquid crystal composition according to the embodiment may be, for example, a compound represented by general formula (ii) (hereinafter, also referred to as a “compound (ii)”):
In the formula, Zii1, Aii1, and mii1 each have the same meaning as Zi1, Ai1, and mi1 in general formula (i), Rii1 and Rii2 each independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, a halogenated alkyl group, or Pi1-Spi1-, wherein —CH2— in the alkyl group may be substituted with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, or —OCO—, provided that —O— moieties are not bonded in series, at least one of Rii1 and Rii2 represents a monovalent organic group having a substituent represented by Ki1, and general formula (ii) has one or two or more Pi1-Spi1-'s, one or two or more monovalent organic groups including a substituent represented by Ki1, and one or more Ri1's, provided that when Ki1 is (K-11), Zii1 is any one of —CH2—CH2COO—, —OCOCH2—CH2—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, and —OCH2CH2O—.
In formula (i) and formula (ii), Zi1 represents a single bond or a group substituted with —CH═CH—, —C═C—, —COO—, —OCO—, —OCOO—, —OOCO—, —CH═CHCOO—, —OCOCH═CH—, —CH2—CH2COO—, —OCOCH2—CH2—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, —OCH2CH2O—, a linear or branched alkylene group having 1 to 40 carbon atoms, or a group in which one or two or more —CH2-'s not adjacent to each other in the alkylene group are replaced with —O—, preferably represents a single bond, —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH2—CH2COO—, —OCOCH2—CH2—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, —OCH2CH2O—, a linear or branched alkylene group having 1 to 40 carbon atoms, or a group in which one or two or more —CH2-'s not adjacent to each other in the alkylene group are replaced with —O—, or a single bond, a linear alkylene group having 2 to 15 carbon atoms, or a group in which one or two or more —CH2-'s not adjacent to each other in the alkylene group are replaced with —O—, and more preferably represents a single bond, CH2—CH2COO—, —OCOCH2—CH2—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, —OCH2CH2O—, an alkylene group (ethylene group (—CH2CH2—)) having 2 carbon atoms, a group in which one —CH2— in the ethylene group is replaced with —O— (—CH2O—, —OCH2—), a linear alkylene group having 3 to 13 carbon atoms, or a group in which one or two or more —CH2-'s not adjacent to each other in the alkylene group are replaced with —O—.
All preferably represents a divalent 6-membered ring aromatic group or a divalent 6-membered ring aliphatic group. All may represent a divalent unsubstituted 6-membered ring aromatic group or a divalent unsubstituted 6-membered ring aliphatic group. A hydrogen atom in these ring structures is preferably not replaced or replaced with an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom. All preferably represents a divalent unsubstituted 6-membered ring aromatic group, a group in which a hydrogen atom in this ring structure is replaced with a fluorine atom, or a divalent unsubstituted 6-membered ring aliphatic group. All preferably represents a 1,4-phenylene group, a 2,6-naphthalene group, or a 1,4-cyclohexyl group, in which a hydrogen atom on the substituent may be replaced with a halogen atom, an alkyl group, or an alkoxy group, provided that at least one substituent is substituted with Pi1-Spi1-.
Preferably mi1 represents an integer of 2 to 5 and more preferably represents an integer of 2 to 4.
In a case where chemical stability is important for the spontaneous orientation aid, Ki1 is preferably (K-1), (K-3), (K-8), (K-9), (K-10), and (K-11), in a case where liquid crystal alignment is important, Ki1 is preferably (K-1) to (K-7), (K-10), and (K-11), in a case where solubility to the liquid crystal compound is important, Ki1 is preferably (K-1), (K-8), and (K-10), and in a case where the balance between these is important, Ki1 is more preferably (K-1), (K-3), (K-9), and (K-11).
In formula (K-1) to formula (K-11), WK1 preferably represents a methine group or C—CH3. XK1 and YK1 each independently preferably represent —CH2— or an oxygen atom. ZK1 preferably represents an oxygen atom.
In formula (ii), Spi1 preferably represents a linear alkylene group having 1 to 18 carbon atoms or a single bond, more preferably represents a linear alkylene group having 2 to 15 carbon atoms or a single bond, and even more preferably represents a linear alkylene group having 3 to 12 carbon atoms or a single bond.
Ri1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group, or Pi1-Spi1-, wherein —CH2— in the alkyl group is preferably replaced with —O—, —OCO—, or —COO—, provided that —O— moieties are not bonded in series, Ri1 more preferably represents a hydrogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, or Pi1-Spi1-, wherein —CH2— in the alkyl group is replaced with —O— or —OCO—, provided that —O— moieties are not bonded in series.
In addition, formula (i) may be, for example, a compound represented by general formula (iii) (hereinafter, also referred to as the “compound (iii)”):
In the formula, Zi1, Ai1, Ri1, and Ki1 each have the same meaning as Zi1, Ai1, Ri1, and Ki1 in general formula (i), Ai2 has the same meaning as Ai1 in general formula (i), Zi2 has the same meaning as Zi1 in general formula (i), in a case where a plurality of Zi1's, Zi2's, Ai1's, miii1's, and/or Ai2's are present, these may be the same or different, provided that one of Ai1 and Ai2 is substituted with at least one Pi1-Spi1- and when Ki1 is (K-11), Zi1 includes at least one of —CH2—CH2COO—, —OCOCH2—CH2—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, or —OCH2CH2O—, miii1 represents an integer of 1 to 5, miii2 represents an integer of 1 to 5, Gi1 represents a divalent, trivalent, or tetravalent branched structure or a divalent, trivalent, or tetravalent aliphatic or aromatic ring structure, and miii3 represents an integer smaller than the valence of Gi1 by 1.
miii1 and miii2 each independently represent an integer of 1 to 5, preferably represent an integer of 2 to 5, and more preferably represent an integer of 2 to 4. No matter whether only one miii1 is present or a plurality of miii1's are present in the molecule, miii1+miii2 is preferably an integer of 1 to 5, preferably an integer of 1 to 4, and preferably an integer of 1 to 3, in the combination of all of miii1 and miii2 in the molecule. Gi1 represents a divalent, trivalent, or tetravalent branched structure or a divalent, trivalent, or tetravalent aliphatic or aromatic ring structure, the divalent, trivalent, or tetravalent branched structure is preferably any structure of 2-substituted carbon atom, a 3-substituted carbon atom, a 4-substituted carbon atom, a 2-substituted nitrogen atom, a 3-substituted nitrogen atom, and a 4-substituted carbon atom, and the divalent, trivalent, or tetravalent aliphatic or aromatic ring structure is preferably 3- or higher substituted benzene ring or 3- or higher substituted cyclohexane ring. miii3 means that Ai1 is bonded to a portion other than atomic bonding, where Gi1 is bonded to Zi2 and accordingly, miii3 represents an integer smaller than the valence of Gi1 by 1.
More specific examples of general formula (ii) include compounds represented by any of formulae (R-1-1) to (R-1-45) In the formulae, Ri1 has the same meaning as Ri1 in formula (ii).
Examples of the compound shown as the compound (iii) include compounds represented by any of general formulae (iii-1) and (iii-2).
Zi1, Ai1, Ri1, and Ki1 each have the same meaning as Zi1, Ai1, Ri1, and Ki1 in general formula (i), Ai2 has the same meaning as Ai1 in general formula (i), Zi2 has the same meaning as Zi1 in general formula (i), when a plurality of Zi1's, Zi2's, Ai1's, miii1's, and/or Ai2's are present, these may be the same or different, mii1 represents an integer of 1 to 5, miii2 represents an integer of 1 to 5, B represents a trivalent branched structure or a trivalent aliphatic or aromatic ring structure, and C represents a tetravalent branched structure or a tetravalent aliphatic or aromatic ring structure.
More specific examples of general formula (iii) include compounds represented by any of formulae (R-1-33) to (R-1-37) In the formulae, Ri1 has the same meaning as Ri1 in formula (ii)
The spontaneous orientation aid for a liquid crystal composition may include one or two or more compounds (i), and may further include a well-known compound used in liquid crystal compositions in addition to one or two or more compounds (i). More specific examples of the spontaneous orientation aid for a liquid crystal composition are represented by (P-1-1) to (P-1-26).
(Liquid Crystal Composition)
The liquid crystal composition of the embodiment includes one kind or two or more kinds of the compound having a partial structure represented by general formula (i). This liquid crystal composition has negative dielectric anisotropy (Δε). The compound having a partial structure represented by general formula (i) included in the liquid crystal composition is the same as the compound (i) of the spontaneous orientation aid for a liquid crystal composition, including the compound (iii), the compound represented by any of formulae (R-1-1) to (R-1-32), the compound (iii), formulae (iii-1) and (iii-2), formulae (R-1-33) to (R-1-37) which are specific examples thereof, and accordingly, the description is omitted here.
A content of the compound (i) is preferably 0.01 to 50% by mass, and the lower limit value thereof is preferably equal to or greater than 0.01% by mass, equal to or greater than 0.1% by mass, equal to or greater than 0.5% by mass, equal to or greater than 0.7% by mass, or equal to or greater than 1% by mass, with respect to a total amount of the liquid crystal composition, from a viewpoint of further suitably aligning liquid crystal molecules. The upper limit value of the content of the compound (i) is preferably equal to or smaller than 50% by mass, equal to or smaller than 30% by mass, equal to or smaller than 10% by mass, equal to or smaller than 7% by mass, equal to or smaller than 5% by mass, equal to or smaller than 4% by mass, equal to or smaller than 3% by mass, with respect to a total amount of the liquid crystal composition, from a viewpoint of excellent response properties.
The liquid crystal composition may further include a compound selected from the group of compounds represented by any of general formulae (N-1), (N-2), and (N-3):
In formulae (N-1), (N-2), and (N-3), RN11, RN12, RN21, RN22, RN31, and RN32 each independently represent an alkyl group having 1 to 8 carbon atoms, one or two or more —CH2-'s not adjacent to each other in the alkyl group each may be independently substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—, ANN11, AN12, AN21, AN22, AN31, and AN32 each independently represent a group selected from the group consisting of (a) a 1,4-cyclohexylene group (one —CH2— or two or more —CH2-'s not adjacent to each other present in this group may be substituted with —O—), (b) a 1,4-phenylene group (one —CH═ or two or more —CH═'s not adjacent to each other present in this group may be substituted with —N═), (c) a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one —CH═ or two or more —CH═'s not adjacent to each other present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═), and a (d) 1,4-cyclohexenylene group, the group (a), the group (b), the group (c), and the group (d) each may be independently substituted with a cyano group, a fluorine atom, or a chlorine atom, ZN11, ZN12, ZN21, ZN22, ZN31, and ZN32 each independently represent a single bond, —CH2CH2—, —(CH2)4—, —OCH2—, —CH2O—, —COO—, —OCO—, —OCF2—, —CF2O—, —CH═N—N═CH—, —CH═CH—, —CF═CF—, or —C≡C—, XN21 represents a hydrogen atom or a fluorine atom, TN31 represents —CH2— or an oxygen atom, nN11, nN12, nN21, nN22, nN31, and nN32 each independently represent an integer of 0 to 3, nNi1+nN12, nN21+nN22, and nN31+nN32 are each independently 1, 2, or 3, and two or more occurrences of one of ANi1 to AN32 and ZN11 to ZN32 may be the same or different.
The compound represented by any of general formula (N-1), (N-2), and (N-3) is preferably a compound having negative Δε and an absolute value greater than 3.
In general formula (N-1), (N-2), and (N-3), RN11, RN12, RN21, RN22, RN31, and RN32 are each independently preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms, even more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 or 3 carbon atoms, and particularly preferably an alkenyl group (propenyl group) having 3 carbon atoms.
In a case where a ring structure to which RN11, RN12, RN21, RN22, RN31, and RN32 are bonded, is a phenyl group (aromatic group), RN11, RN12, RN21, RN22, RN31, and RN32 are each independently preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 or 5 carbon atoms, and in a case where the ring structure, to which these are bonded, is a saturated ring structure of cyclohexane, pyran, and dioxane, RN11, RN12, RN21, RN22, RN31, and RN32 are each independently preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize a nematic phase, a total number of carbon atoms and oxygen atoms, in a case where oxygen atoms are present, is preferably equal to or smaller than 5 and the structure thereof is preferably linear.
The alkenyl group is preferably selected from groups represented by any of formula (R1) to formula (R5) (each black point in each formula represents atomic bonding).
ANi1, AN12, AN21, AN22, AN31, and AN32 are each independently an aromatic group, in a case where a value greater than Δn is required to obtain, and preferably an aliphatic group, in order to improve a response speed. AN11, AN12, AN21, AN22, AN31, and AN32 each independently preferably represent a trans-1,4-cyclohexylene group, 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, a 2,3-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo [2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, more preferably represent the following structures:
and more preferably represent a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group, or a 1,4-phenylene group.
ZN11, ZN12, ZN21, ZN22, ZN31, and ZN32 each independently preferably represent —CH2O—, —CF2O—, —CH2CH2—, —CF2CF2—, or a single bond, more preferably represent —CH2O—, —CH2CH2—, or a single bond, and particularly preferably represent —CH2O— or a single bond.
XN21 is preferably a fluorine atom.
TN31 is preferably an oxygen atom.
nNi1+nN12, nN21+nN22, and nN31+nN32 are preferably 1 or 2, and a combination in which nN11 is 1 and nN12 is 0, a combination in which nN11 is 2 and nN12 is 0, a combination in which nN11 is 1 and nN12 is 1, a combination in which nN11 is 2 and nN12 is 1, a combination in which nN21 is 1 and nN22 is 0, a combination in which nN21 is 2 and nN22 is 0, a combination in which nN31 is 1 and nN32 is 0, and a combination in which nN31 is 2 and nN32 is 0 are preferable.
The preferable lower limit value of the content of the compound represented by formula (N-1) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 10% by mass, equal to or greater than 20% by mass, equal to or greater than 30% by mass, equal to or greater than 40% by mass, equal to or greater than 50% by mass, equal to or greater than 55% by mass, equal to or greater than 60% by mass, equal to or greater than 65% by mass, equal to or greater than 70% by mass, equal to or greater than 75% by mass, and equal to or greater than 80% by mass. The preferable upper limit value of the content thereof is equal to or smaller than 95% by mass, equal to or smaller than 85% by mass, equal to or smaller than 75% by mass, equal to or smaller than 65% by mass, equal to or smaller than 55% by mass, equal to or smaller than 45% by mass, equal to or smaller than 35% by mass, equal to or smaller than 25% by mass, and equal to or smaller than 20% by mass.
The preferable lower limit value of the content of the compound represented by formula (N-2) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 10% by mass, equal to or greater than 20% by mass, equal to or greater than 30% by mass, equal to or greater than 40% by mass, equal to or greater than 50% by mass, equal to or greater than 55% by mass, equal to or greater than 60% by mass, equal to or greater than 65% by mass, equal to or greater than 70% by mass, equal to or greater than 75% by mass, and equal to or greater than 80% by mass. The preferable upper limit value of the content thereof is equal to or smaller than 95% by mass, equal to or smaller than 85% by mass, equal to or smaller than 75% by mass, equal to or smaller than 65% by mass, equal to or smaller than 55% by mass, equal to or smaller than 45% by mass, equal to or smaller than 35% by mass, equal to or smaller than 25% by mass, and equal to or smaller than 20% by mass.
The preferable lower limit value of the content of the compound represented by formula (N-3) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 10% by mass, equal to or greater than 20% by mass, equal to or greater than 30% by mass, equal to or greater than 40% by mass, equal to or greater than 50% by mass, equal to or greater than 55% by mass, equal to or greater than 60% by mass, equal to or greater than 65% by mass, equal to or greater than 70% by mass, equal to or greater than 75% by mass, and equal to or greater than 80% by mass. The preferable upper limit value of the content thereof is equal to or smaller than 95% by mass, equal to or smaller than 85% by mass, equal to or smaller than 75% by mass, equal to or smaller than 65% by mass, equal to or smaller than 55% by mass, equal to or smaller than 45% by mass, equal to or smaller than 35% by mass, equal to or smaller than 25% by mass, and equal to or smaller than 20% by mass.
In a case where a viscosity of the composition of the embodiment is maintained to be low and a composition having a high response speed is necessary, it is preferable that the lower limit value is low and the upper limit value is low. In addition, in a case where Tni of the composition of the embodiment is maintained to be high and a composition having excellent temperature stability is necessary, it is preferable that the lower limit value is low and the upper limit value is low. In a case where it is desired to increase dielectric anisotropy for maintaining a driving voltage to be low, it is preferable that the lower limit value is high and the upper limit value is high.
As the compound represented by general formula (N-1), a compound group represented by general formulae (N-1a) to (N-1 g) can be used.
In the formulae, RN11 and RN12 represent the same meaning as RN11 and RN12 in general formula (N-1), nNa11 represents 0 or 1, nNb11 represents 0 or 1, nNc11 represents 0 or 1, nNd11 represents 0 or 1, nNe11 represents 1 or 2, nNf11 represents 1 or 2, nNg11 represents 1 or 2, ANe11 represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group, ANg11 represents a trans-1,4-cyclohexylene group, 1,4-cyclohexenylene group, or 1,4-phenylene group, at least one thereof represents a 1,4-cyclohexenylene group, and ZNe11 represents a single bond or ethylene, and at least one thereof represents ethylene.
More specifically, the compound represented by general formula (N-1) is preferably a compound selected from the compound group represented by general formulae (N-1-1) to (N-1-21).
The compound represented by general formula (N-1-1) is the following compound.
In the formula, RN111 and RN112 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group, a pentyl group, or a vinyl group. RN112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group or a butoxy group.
The compound represented by general formula (N-1-1) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be low. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-1) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, equal to or greater than 33% by mass, or equal to or greater than 35% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 50% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, equal to or smaller than 6% by mass, equal to or smaller than 5% by mass, or equal to or smaller than 3% by mass.
The compound represented by general formula (N-1-1) is preferably a compound selected from the compound group represented by formula (N-1-1.1) to formula (N-1-1.23), preferably a compound represented by formula (N-1-1.1) to formula (N-1-1.4), and preferably a compound represented by formula (N-1-1.1) and formula (N-1-1.3).
The compounds represented by formulae (N-1-1.1) to (N-1-1.22) can be used alone or in combination, and the preferable lower limit value of the content of the single compound or these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, equal to or greater than 33% by mass, or equal to or greater than 35% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 50% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, equal to or smaller than 6% by mass, equal to or smaller than 5% by mass, or equal to or smaller than 3% by mass.
The compound represented by general formula (N-1-2) is the following compound.
In the formula, RN121 and RN122 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, a butyl group, or a pentyl group. RN122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably a methyl group, a propyl group, a methoxy group, an ethoxy group, or a propoxy group.
The compound represented by general formula (N-1-2) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be low, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-2) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, equal to or greater than 33% by mass, equal to or greater than 35% by mass, equal to or greater than 37% by mass, equal to or greater than 40% by mass, or equal to or greater than 42% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 50% by mass, equal to or smaller than 48% by mass, equal to or smaller than 45% by mass, equal to or smaller than 43% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, equal to or smaller than 6% by mass, or equal to or smaller than 5% by mass.
The compound represented by general formula (N-1-2) is preferably a compound selected from the compound group represented by formula (N-1-2.1) to formula (N-1-2.22), preferably a compound represented by formula (N-1-2.3) to formula (N-1-2.7), formula (N-1-2.10), formula (N-1-2.11), formula (N-1-2.13), and formula (N-1-2.20), preferably a compound represented by formula (N-1-2.3) to formula (N-1-2.7), in a case where the improvement of Δε is important, preferably a compound represented by formula (N-1-2.10), formula (N-1-2.11), and formula (N-1-2.13), in a case where the improvement of TNI is important, and preferably a compound represented by formula (N-1-2.20), in a case where the improvement of the response speed is important.
The compounds represented by formula (N-1-2.1) to formula (N-1-2.22) can be used alone or in combination, and the preferable lower limit value of the content of the single compound or these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, equal to or greater than 33% by mass, or equal to or greater than 35% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 50% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, equal to or smaller than 6% by mass, equal to or smaller than 5% by mass, or equal to or smaller than 3% by mass.
The compound represented by general formula (N-1-3) is the following compound.
In the formula, RN131 and RN132 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group. RN132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably a 1-propenyl group, an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-3) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-3) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-3) is preferably a compound selected from the compound group represented by formula (N-1-3.1) to formula (N-1-3.21), preferably a compound represented by formulae (N-1-3.1) to (N-1-3.7) and formula (N-1-3.21), and preferably a compound represented by formula (N-1-3.1), formula (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4), and formula (N-1-3.6).
The compounds represented by formula (N-1-3.1) to formula (N-1-3.4), formula (N-1-3.6), and formula (N-1-3.21) can be used alone or in combination, and a combination of formula (N-1-3.1) and formula (N-1-3.2), or two or three kinds of combinations selected from formula (N-1-3.3), formula (N-1-3.4), and formula (N-1-3.6) is preferable. The preferable lower limit value of the content of the single compound or these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-4) is the following compound.
In the formula, RN141 and RN142 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN141 and RN142 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably a methyl group, a propyl group, an ethoxy group, or a butoxy group.
The compound represented by general formula (N-1-4) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be low. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-4) with respect to a total amount of the composition of the embodiment is equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 11% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 8% by mass.
The compound represented by general formula (N-1-4) is preferably a compound selected from the compound group represented by formula (N-1-4.1) to formula (N-1-4.14), preferably a compound represented by formula (N-1-4.1) to formula (N-1-4.4), and preferably a compound represented by formula (N-1-4.1), formula (N-1-4.2), formula (N-1-4.4).
The compounds represented by formulae (N-1-4.1) to (N-1-4.14) can be used alone or in combination, and the preferable lower limit value of the content of the single compound or these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 11% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 8% by mass.
The compound represented by general formula (N-1-5) is the following compound.
In the formula, RN151 and RN152 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN151 and RN152 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group.
The compound represented by general formula (N-1-5) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be low, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-5) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 8% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-5) is preferably a compound selected from the compound group represented by formula (N-1-5.1) to formula (N-1-5.6), and preferably a compound represented by formula (N-1-5.1), formula (N-1-5.2), and formula (N-1-5.4).
The compounds represented by formula (N-1-5.1), formula (N-1-5.2), and formula (N-1-5.4) can be used alone or in combination, and the preferable lower limit value of the content of the single compound or these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 8% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-10) is the following compound.
In the formula, RN1101 and RN1102 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1101 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, a butyl group, a vinyl group, or a 1-propenyl group. RN1102 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-10) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment of the embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be high, and in a case where TNI is important, the effect is high by setting the content to be high. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-10) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-10) is preferably a compound selected from the compound group represented by formula (N-1-10.1) to formula (N-1-10.21), preferably a compound represented by formulae (N-1-10.1) to (N-1-10.5), formula (N-1-10.20), and formula (N-1-10.21), and preferably a compound represented by formula (N-1-10.1), formula (N-1-10.2), formula (N-1-10.20), and formula (N-1-10.21).
The compounds represented by formula (N-1-10.1), formula (N-1-10.2), formula (N-1-10.20), and formula (N-1-10.21) can be used alone or in combination, and the preferable lower limit value of the content of the single compound or these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-11) is the following compound.
In the formula, RN1111 and RN1112 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, a butyl group, a vinyl group, or a 1-propenyl group. RN1112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-11) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be low, and in a case where TNI is important, the effect is high by setting the content to be high. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-11) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-11) is preferably a compound selected from the compound group represented by formula (N-1-11.1) to formula (N-1-11.15), preferably a compound represented by formulae (N-1-11.1) to (N-1-11.15), and preferably a compound represented by formula (N-1-11.2) and formula (N-1-11.4).
The compounds represented by formula (N-1-11.2) and formula (N-1-11.4) can be used alone or in combination, and the preferable lower limit value of the content of the single compound or these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-12) is the following compound.
In the formula, RN1121 and RN1122 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group. RN1122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-12) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-12) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-13) is the following compound.
In the formula, RN1131 and RN1132 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group. RN1132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-13) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-13) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-14) is the following compound.
In the formula, RN1141 and RN1142 each independently represent the same meaning as RN11 and RN12 in general formula (N).)
RN1141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group. RN1142 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-14) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment of the embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-14) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-15) is the following compound.
In the formula, RN1151 and RN1152 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1151 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group. RN1152 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-15) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-15) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-16) is the following compound.
In the formula, RN1161 and RN1162 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1161 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group. RN1162 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-16) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-16) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-17) is the following compound.
In the formula, RN1171 and RN1172 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1171 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group. RN1172 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-17) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-17) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-18) is the following compound.
In the formula, RN1181 and RN1182 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1181 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a methyl group, an ethyl group, a propyl group, or a butyl group. RN1182 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
The compound represented by general formula (N-1-18) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-18) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-18) is preferably a compound selected from the compound group represented by formula (N-1-18.1) to formula (N-1-18.5), preferably a compound represented by formulae (N-1-18.1) to (N-1-18.3), and preferably a compound represented by formula (N-1-18.2) and formula (N-1-18.3).
The compound represented by general formula (N-1-20) is the following compound.
In the formula, RN1201 and RN1202 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1201 and RN1202 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group.
The compound represented by general formula (N-1-20) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-20) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-21) is the following compound.
In the formula, RN1211 and RN1212 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1211 and RN1212 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group.
The compound represented by general formula (N-1-21) can be used alone or a combination of two or more compounds can also be used. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-21) with respect to a total amount of the composition of the embodiment is equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (N-1-22) is the following compound.
In the formula, RN1221 and RN1222 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN1221 and RN1222 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group.
The compound represented by general formula (N-1-22) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be great. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-1-21) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 5% by mass.
The compound represented by general formula (N-1-22) is preferably a compound selected from the compound group represented by formula (N-1-22.1) to formula (N-1-22.12), preferably a compound represented by formulae (N-1-22.1) to (N-1-22.5), and preferably a compound represented by formulae (N-1-22.1) to (N-1-22.4).
The compound represented by general formula (N-3) is preferably a compound selected from the compound group represented by general formula (N-3-2).
In the formula, RN321 and RN322 each independently represent the same meaning as RN11 and RN12 in general formula (N).
RN321 and RN322 are preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group or a pentyl group.
The compound represented by general formula (N-3-2) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the improvement of Δε is important, the content is preferably set to be high, in a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in a case where TNI is important, the effect is high by setting the content to be low. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (N-3-2) with respect to a total amount of the composition of the embodiment is equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, equal to or greater than 33% by mass, or equal to or greater than 35% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 50% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, equal to or smaller than 6% by mass, or equal to or smaller than 5% by mass.
The compound represented by general formula (N-3-2) is preferably a compound selected from the compound group represented by formula (N-3-2.1) to formula (N-3-2.3).
The liquid crystal composition may further include a compound represented by general formula (L):
In formula (L), RL1 and RL2 each independently represent an alkyl group having 1 to 8 carbon atoms, one or two or more —CH2-'s not adjacent to each other in the alkyl group each may be independently substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—, nL1 represents 0, 1, 2, or 3, AL1, AL2, and AL3 each independently represent a group selected from the group consisting of (a) a 1,4-cyclohexylene group (one —CH2— or two or more —CH2-'s not adjacent to each other present in this group may be substituted with —O—), (b) a 1,4-phenylene group (one —CH═ or two or more —CH═'s not adjacent to each other present in this group may be substituted with —N═), and (c) a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one —CH═ or two or more —CH═'s not adjacent to each other present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═), the group (a), the group (b), and the group (c) each may be independently substituted with a cyano group, a fluorine atom, or a chlorine atom, ZL1 and ZL2 each independently represent a single bond, —CH2CH2—, —(CH2)4—, —OCH2—, —CH2O—, —COO—, —OCO—, —OCF2—, —CF2O—, —CH═N—N═CH—, —CH═CH—, —CF═CF—, or —C≡C—, when nLl is 2 or 3 and a plurality of AL2's are present, these may be the same or different, and when nL1 is 2 or 3 and a plurality of ZL2's are present, these may be the same or different, exclusive of compounds represented by general formula (N-1), (N-2), and (N-3).
The compound represented by general formula (L) corresponds to a compound (value of Δε is −2 to 2) which is substantially dielectrically neutral. The compound represented by general formula (L) can be used alone or in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with desired performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one in one embodiment, for example. Alternatively, in another embodiment, the number thereof is one, two, three, four, five, six, seven, eight, nine, or ten or more.
In the composition of the embodiment, it is necessary that the content of the compound represented by general formula (L) is suitably adjusted in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, a birefringence, process suitability, dropping marks, burning, or dielectric anisotropy.
The preferable lower limit value of the content of the compound represented by formula (L) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 10% by mass, equal to or greater than 20% by mass, equal to or greater than 30% by mass, equal to or greater than 40% by mass, equal to or greater than 50% by mass, equal to or greater than 55% by mass, equal to or greater than 60% by mass, equal to or greater than 65% by mass, equal to or greater than 70% by mass, equal to or greater than 75% by mass, and equal to or greater than 80% by mass. The preferable upper limit value of the content thereof is equal to or smaller than 95% by mass, equal to or smaller than 85% by mass, equal to or smaller than 75% by mass, equal to or smaller than 65% by mass, equal to or smaller than 55% by mass, equal to or smaller than 45% by mass, equal to or smaller than 35% by mass, equal to or smaller than 25% by mass, and equal to or smaller than 20% by mass.
In a case where a viscosity of the composition of the embodiment is maintained to be low and a composition having a high response speed is necessary, it is preferable that the lower limit value is high and the upper limit value is high. In addition, in a case where Tni of the composition of the embodiment is maintained to be high and a composition having excellent temperature stability is necessary, it is preferable that the lower limit value is high and the upper limit value is high. In a case where it is desired to increase dielectric anisotropy for maintaining a driving voltage to be low, it is preferable that the lower limit value is low and the upper limit value is low.
In a case where the reliability is important, both of RL1 and RL2 are preferably an alkyl group, in a case where a decrease in volatility of the compound is important, both of RL1 and RL2 are preferably an alkoxy group, and in a case where a decrease in viscosity is important, at least one thereof is preferably an alkenyl group.
The number of halogen atoms present in a molecule is preferably 0, 1, 2, or 3, preferably 0 or 1, and in a case where compatibility with other liquid crystal molecules is important, the number thereof is preferably 1.
In a case where a ring structure, to which RL1 and RL2 are bonded, is a phenyl group (aromatic group), RL1 and RL2 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 or 5 carbon atoms, and in a case where the structure, to which these are bonded, is a saturated ring structure of cyclohexane, pyran, and dioxane, RL1 and RL2 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize a nematic phase, a total number of carbon atoms and oxygen atoms, in a case where oxygen atoms are present, is preferably equal to or smaller than 5 and the structure thereof is preferably linear.
The alkenyl group is preferably selected from groups represented by any of formula (R1) to formula (R5) (each black point in each formula represents atomic bonding).
In a case where the response speed is important, nL1 is preferably 0, in a case of improving the upper limit temperature of the nematic phase, nL1 is preferably 2 or 3, and in a case of keeping a balance between these, nL1 is preferably 1. In addition, in order to satisfy the properties required as the composition, a combination of compounds having different values is preferable.
AL1, AL2, and AL3 are preferably an aromatic group, in a case where a value greater than Δn is required to obtain, and preferably an aliphatic group, in order to improve a response speed. AL1, AL2, and AL3 each independently preferably represent a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo [2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, more preferably represent the following structure:
and more preferably represent a trans-1,4-cyclohexylene group or a 1,4-phenylene group.
In a case where the response speed is important, ZL1 and ZL2 are preferably a single bond.
The number of halogen atoms in a molecule of the compound represented by general formula (L) is preferably 0 or 1.
The compound represented by general formula (L) is preferably a compound selected from the compound group represented by general formula (L-1) to (L-7).
The compound represented by general formula (L-1) is the following compound.
In the formula, RL11 and RL12 each independently represent the same meaning as RL1 and RL2 in general formula (L).
RL11 and RL12 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms.
The compound represented by general formula (L-1) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
The preferable lower limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 15% by mass, equal to or greater than 20% by mass, equal to or greater than 25% by mass, equal to or greater than 30% by mass, equal to or greater than 35% by mass, equal to or greater than 40% by mass, equal to or greater than 45% by mass, equal to or greater than 50% by mass, or equal to or greater than 55% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 95% by mass, equal to or smaller than 90% by mass, equal to or smaller than 85% by mass, equal to or smaller than 80% by mass, equal to or smaller than 75% by mass, equal to or smaller than 70% by mass, equal to or smaller than 65% by mass, equal to or smaller than 60% by mass, equal to or smaller than 55% by mass, equal to or smaller than 50% by mass, equal to or smaller than 45% by mass, equal to or smaller than 40% by mass, equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, or equal to or smaller than 25% by mass.
In a case where a viscosity of the composition of the embodiment is maintained to be low and a composition having a high response speed is necessary, it is preferable that the lower limit value is high and the upper limit value is high. In addition, in a case where Tni of the composition of the embodiment is maintained to be high and a composition having excellent temperature stability is necessary, it is preferable that the lower limit value is moderate and the upper limit value is moderate. In a case where it is desired to increase dielectric anisotropy for maintaining a driving voltage to be low, it is preferable that the lower limit value is low and the upper limit value is low.
The compound represented by general formula (L-1) is preferably a compound selected from the compound group represented by general formula (L-1-1).
In the formula, RL12 represents the same meaning as the meaning in general formula (L-1).
The compound represented by general formula (L-1-1) is preferably a compound selected from the compound group represented by formula (L-1-1.1) to formula (L-1-1.3), preferably a compound represented by formula (L-1-1.2) or formula (L-1-1.3), and preferably a compound represented by formula (L-1-1.3).
The preferable lower limit value of the content of the compound represented by formula (L-1-1.3) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, or equal to or greater than 10% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, equal to or smaller than 6% by mass, equal to or smaller than 5% by mass, or equal to or smaller than 3% by mass.
The compound represented by general formula (L-1) is preferably a compound selected from the compound group represented by general formula (L-1-2).
In the formula, RL12 represents the same meaning as the meaning in general formula (L-1).
The preferable lower limit value of the content of the compound represented by formula (L-1-2) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, or equal to or greater than 35% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 60% by mass, equal to or smaller than 55% by mass, equal to or smaller than 50% by mass, equal to or smaller than 45% by mass, equal to or smaller than 42% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, or equal to or smaller than 30% by mass.
The compound represented by general formula (L-1-2) is preferably a compound selected from the compound group represented by formula (L-1-2.1) to formula (L-1-2.4), and preferably a compound represented by formula (L-1-2.2) to formula (L-1-2.4). Particularly, the compound represented by formula (L-1-2.2) is preferable, in order to particularly improve the response speed of the composition of the embodiment. In addition, in a case of obtaining Tni higher than the response speed, the compound represented by formula (L-1-2.3) or formula (L-1-2.4) is preferably used. The content of the compound represented by formula (L-1-2.3) and formula (L-1-2.4) set to be equal to or greater than 30% by mass is not preferable, in order to improve solubility at a low temperature.
The preferable lower limit value of the content of the compound represented by formula (L-1-2.2) with respect to a total amount of the composition of the embodiment is equal to or greater than 10% by mass, equal to or greater than 15% by mass, equal to or greater than 18% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, equal to or greater than 33% by mass, equal to or greater than 35% by mass, equal to or greater than 38% by mass, or equal to or greater than 40% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 60% by mass, equal to or smaller than 55% by mass, equal to or smaller than 50% by mass, equal to or smaller than 45% by mass, equal to or smaller than 43% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 32% by mass, equal to or smaller than 30% by mass, equal to or smaller than 27% by mass, equal to or smaller than 25% by mass, or equal to or smaller than 22% by mass.
The preferable lower limit value of the content of a total of the compound represented by formula (L-1-1.3) and the compound represented by formula (L-1-2.2) with respect to a total amount of the composition of the embodiment is equal to or greater than 10% by mass, equal to or greater than 15% by mass, equal to or greater than 20% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, equal to or greater than 35% by mass, or equal to or greater than 40% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 60% by mass, equal to or smaller than 55% by mass, equal to or smaller than 50% by mass, equal to or smaller than 45% by mass, equal to or smaller than 43% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 32% by mass, equal to or smaller than 30% by mass, equal to or smaller than 27% by mass, equal to or smaller than 25% by mass, or equal to or smaller than 22% by mass.
The compound represented by general formula (L-1) is preferably a compound selected from the compound group represented by general formula (L-1-3).
In the formula, RL13 and RL14 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
RL13 and RL14 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms.
The preferable lower limit value of the content of the compound represented by formula (L-1-3) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, or equal to or greater than 30% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 60% by mass, equal to or smaller than 55% by mass, equal to or smaller than 50% by mass, equal to or smaller than 45% by mass, equal to or smaller than 40% by mass, equal to or smaller than 37% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 27% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 17% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, or equal to or smaller than 10% by mass.
The compound represented by general formula (L-1-3) is preferably a compound selected from the compound group represented by formula (L-1-3.1) to formula (L-1-3.13), and preferably a compound represented by formula (L-1-3.1), formula (L-1-3.3), or formula (L-1-3.4). Particularly, the compound represented by formula (L-1-3.1) is preferable, in order to particularly improve the response speed of the composition of the embodiment. In addition, in a case of obtaining Tni higher than the response speed, the compound represented by formula (L-1-3.3), formula (L-1-3.4), formula (L-1-3.11), and formula (L-1-3.12) is preferably used. All of the content of the compound represented by formula (L-1-3.3), formula (L-1-3.4), formula (L-1-3.11), and formula (L-1-3.12) set to be equal to or greater than 20% is not preferable, in order to improve solubility at a low temperature.
The preferable lower limit value of the content of the compound represented by formula (L-1-3.1) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 18% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 20% by mass, equal to or smaller than 17% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, or equal to or smaller than 6% by mass.
The compound represented by general formula (L-1) is preferably a compound selected from the compound group represented by general formula (L-1-4) and/or (L-1-5).
In the formula, RL15 and RL16 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
RL15 and RL16 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms.
The preferable lower limit value of the content of the compound represented by formula (L-1-4) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 17% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, or equal to or smaller than 10% by mass.
The preferable lower limit value of the content of the compound represented by formula (L-1-5) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 17% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, or equal to or smaller than 10% by mass.
The compound represented by general formulae (L-1-4) and (L-1-5) is preferably a compound selected from the compound group represented by formula (L-1-4.1) to formula (L-1-4.3) and formula (L-1-5.1) to formula (L-1-5.3), and preferably a compound represented by formula (L-1-4.2) or formula (L-1-5.2).
The preferable lower limit value of the content of the compound represented by formula (L-1-4.2) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 18% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 20% by mass, equal to or smaller than 17% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, or equal to or smaller than 6% by mass.
A combination of two or more kinds of compounds selected from the compounds represented by formula (L-1-1.3), formula (L-1-2.2), formula (L-1-3.1), formula (L-1-3.3), formula (L-1-3.4), formula (L-1-3.11), And formula (L-1-3.12) is preferable, and a combination of two or more kinds of compounds selected from the compounds represented by formula (L-1-1.3), formula (L-1-2.2), formula (L-1-3.1), formula (L-1-3.3), formula (L-1-3.4), formula (L-1-4.2). The preferable lower limit value of the content of a total content of these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 13% by mass, equal to or greater than 15% by mass, equal to or greater than 18% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, equal to or greater than 33% by mass, or equal to or greater than 35% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 80% by mass, equal to or smaller than 70% by mass, equal to or smaller than 60% by mass, equal to or smaller than 50% by mass, equal to or smaller than 45% by mass, equal to or smaller than 40% by mass, equal to or smaller than 37% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, equal to or smaller than 30% by mass, equal to or smaller than 28% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, or equal to or smaller than 20% by mass.
In a case where the reliability is important, a combination of two or more kinds of compounds selected from the compounds represented by formula (L-1-3.1), formula (L-1-3.3), and formula (L-1-3.4) is preferable, and in a case where the response speed of the composition is important, a combination of two or more kinds of compounds selected from the compounds represented by formula (L-1-1.3) and formula (L-1-2.2) is preferable.
The compound represented by general formula (L-1) is preferably a compound selected from the compound group represented by general formula (L-1-6).
In the formula, RL17 and RL18 each independently represent a methyl group or a hydrogen atom.
The preferable lower limit value of the content of the compound represented by formula (L-1-6) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 5% by mass, equal to or greater than 10% by mass, equal to or greater than 15% by mass, equal to or greater than 17% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 25% by mass, equal to or greater than 27% by mass, equal to or greater than 30% by mass, or equal to or greater than 35% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 60% by mass, equal to or smaller than 55% by mass, equal to or smaller than 50% by mass, equal to or smaller than 45% by mass, equal to or smaller than 42% by mass, equal to or smaller than 40% by mass, equal to or smaller than 38% by mass, equal to or smaller than 35% by mass, equal to or smaller than 33% by mass, or equal to or smaller than 30% by mass.
The compound represented by general formula (L-1-6) is preferably a compound selected from the compound group represented by formula (L-1-6.1) to formula (L-1-6.3).
The compound represented by general formula (L-2) is the following compound.
In the formula, RL21 and RL22 each independently represent the same meaning as RL1 and RL2 in general formula (L).
RL21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and RL22 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
The compound represented by general formula (L-1) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In a case where the solubility at a low temperature is important, the effect is high by setting the content to be great, and in contrast, in a case where the response speed is important, the effect is high by setting the content to be low. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The preferable lower limit value of the content of the compound represented by formula (L-2) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, or equal to or greater than 10% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, equal to or smaller than 6% by mass, equal to or smaller than 5% by mass, or equal to or smaller than 3% by mass.
The compound represented by general formula (L-2) is preferably a compound selected from the compound group represented by formula (L-2.1) to formula (L-2.6), and preferably a compound represented by formula (L-2.1), formula (L-2.3), formula (L-2.4), and formula (L-2.6).
The compound represented by general formula (L-3) is the following compound.
In the formula, RL31 and RL32 each independently represent the same meaning as RL1 and RL2 in general formula (L).
RL31 and RL32 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
The compound represented by general formula (L-3) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
The preferable lower limit value of the content of the compound represented by formula (L-3) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, or equal to or greater than 10% by mass. The preferable upper limit value of the content thereof with respect to a total amount of the composition of the embodiment is equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, equal to or smaller than 8% by mass, equal to or smaller than 7% by mass, equal to or smaller than 6% by mass, equal to or smaller than 5% by mass, or equal to or smaller than 3% by mass.
In a case of obtaining a high birefringence, the effect is high by setting the content to be great, and in contrast, in a case where a high Tni is important, the effect is high by setting the content to be low. In a case of improving dropping marks or burning properties, the range of the content is preferably set to be moderate.
The compound represented by general formula (L-3) is preferably a compound selected from the compound group represented by formula (L-3.1) to formula (L-3.7), and preferably a compound represented by formula (L-3.2) to formula (L-3.7).
The compound represented by general formula (L-4) is the following compound.
In the formula, RL41 and RL42 each independently represent the same meaning as RL1 and RL2 in general formula (L).
RL41 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and RL42 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
The compound represented by general formula (L-4) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In the composition of the embodiment, it is necessary that the content of the compound represented by general formula (L-4) is suitably adjusted in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, a birefringence, process suitability, dropping marks, burning, or dielectric anisotropy.
The preferable lower limit value of the content of the compound represented by formula (L-4) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 14% by mass, equal to or greater than 16% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 26% by mass, equal to or greater than 30% by mass, equal to or greater than 35% by mass, or equal to or greater than 40% by mass. The preferable upper limit value of the content of the compound represented by formula (L-4) with respect to a total amount of the composition of the embodiment is equal to or smaller than 50% by mass, equal to or smaller than 40% by mass, equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 5% by mass.
The compound represented by general formula (L-4) is preferably, for example, a compound represented by formula (L-4.1) to formula (L-4.3).
In accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence, a compound represented by formula (L-4.1) may be included, a compound represented by formula (L-4.2) may be included, both of a compound represented by formula (L-4.1) and a compound represented by formula (L-4.2) may be included, or all of compounds represented by formula (L-4.1) to formula (L-4.3) may be included.
The preferable lower limit value of the content of the compound represented by formula (L-4.1) or formula (L-4.2) with respect to a total amount of the composition of the embodiment is equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 9% by mass, equal to or greater than 11% by mass, equal to or greater than 12% by mass, equal to or greater than 13% by mass, equal to or greater than 18% by mass, or equal to or greater than 21% by mass. The preferable upper limit value of the content thereof is equal to or smaller than 45% by mass, equal to or smaller than 40% by mass, equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 8% by mass.
In a case where both of a compound represented by formula (L-4.1) and a compound represented by formula (L-4.2) are included, the preferable lower limit value of the content of both compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 15% by mass, equal to or greater than 19% by mass, equal to or greater than 24% by mass, or equal to or greater than 30% by mass. The preferable upper limit value of the content thereof is equal to or smaller than 45% by mass, equal to or smaller than 40% by mass, equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (L-4) is preferably, for example, a compound represented by formula (L-4.4) to formula (L-4.6), and preferably a compound represented by formula (L-4.4).
In accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence, a compound represented by formula (L-4.4) may be included, a compound represented by formula (L-4.5) may be included, or both of a compound represented by formula (L-4.4) and a compound represented by formula (L-4.5) may be included.
The preferable lower limit value of the content of the compound represented by formula (L-4.4) or formula (L-4.5) with respect to a total amount of the composition of the embodiment is equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 9% by mass, equal to or greater than 11% by mass, equal to or greater than 12% by mass, equal to or greater than 13% by mass, equal to or greater than 18% by mass, or equal to or greater than 21% by mass. The preferable upper limit value of the content thereof is equal to or smaller than 45% by mass, equal to or smaller than 40% by mass, equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 8% by mass.
In a case where both of a compound represented by formula (L-4.4) and a compound represented by formula (L-4.5) are included, the preferable lower limit value of the content of both compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 15% by mass, equal to or greater than 19% by mass, equal to or greater than 24% by mass, or equal to or greater than 30% by mass, and the preferable upper limit value thereof is equal to or smaller than 45% by mass, equal to or smaller than 40% by mass, equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, or equal to or smaller than 13% by mass.
The compound represented by general formula (L-4) is preferably a compound represented by formula (L-4.7) to formula (L-4.10), and particularly preferably a compound represented by formula (L-4.9).
The compound represented by general formula (L-5) is the following compound.
In the formula, RL5 and RL2 each independently represent the same meaning as RL1 and RL2 in general formula (L).
RL51 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and RL52 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 or 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
The compound represented by general formula (L-5) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
In the composition of the embodiment, it is necessary that the content of the compound represented by general formula (L-5) is suitably adjusted in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, a birefringence, process suitability, dropping marks, burning, or dielectric anisotropy.
The preferable lower limit value of the content of the compound represented by formula (L-5) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 14% by mass, equal to or greater than 16% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 26% by mass, equal to or greater than 30% by mass, equal to or greater than 35% by mass, or equal to or greater than 40% by mass. The preferable upper limit value of the content of the compound represented by formula (L-5) with respect to a total amount of the composition of the embodiment is equal to or smaller than 50% by mass, equal to or smaller than 40% by mass, equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 5% by mass.
The compound represented by general formula (L-5) is preferably a compound represented by formula (L-5.1) or formula (L-5.2), and particularly preferably a compound represented by formula (L-5.1).
The preferable lower limit value of the content of these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, or equal to or greater than 7% by mass. The preferable upper limit value of the content of these compounds is equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 9% by mass.
The compound represented by general formula (L-5) is preferably a compound selected from the compound group represented by formula (L-5.3) or formula (L-5.4).
The preferable lower limit value of the content of these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, or equal to or greater than 7% by mass. The preferable upper limit value of the content of these compounds is equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 9% by mass.
The compound represented by general formula (L-5) is preferably a compound selected from the compound group represented by formula (L-5.5) to formula (L-5.7), and particularly preferably a compound represented by formula (L-5.7).
The preferable lower limit value of the content of these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, or equal to or greater than 7% by mass. The preferable upper limit value of the content of these compounds is equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 9% by mass.
The compound represented by general formula (L-6) is the following compound.
In the formula, RL61 and RL62 each independently represent the same meaning as RL1 and RL2 in general formula (L), and RL61 and RL62 each independently represent a hydrogen atom or a fluorine atom.
RL61 and RL62 are each independently an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and one of XL61 and XL62 is a fluorine atom, and the other one is preferably a hydrogen atom.
The compound represented by general formula (L-6) can be used alone, and two or more compounds can also be used in combination. The kind of the compound which can be used in combination is not particularly limited, and compounds are suitably used in combination, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, four, or five or more, in one embodiment, for example.
The preferable lower limit value of the content of the compound represented by formula (L-6) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 14% by mass, equal to or greater than 16% by mass, equal to or greater than 20% by mass, equal to or greater than 23% by mass, equal to or greater than 26% by mass, equal to or greater than 30% by mass, equal to or greater than 35% by mass, or equal to or greater than 40% by mass. The preferable upper limit value of the content of the compound represented by formula (L-6) with respect to a total amount of the composition of the embodiment is equal to or smaller than 50% by mass, equal to or smaller than 40% by mass, equal to or smaller than 35% by mass, equal to or smaller than 30% by mass, equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 5% by mass. In a case where an increase in Δn is important, it is preferable to increase the content thereof, and in a case where precipitation at a low temperature is important, it is preferable to decrease the content thereof.
The compound represented by general formula (L-6) is preferably a compound represented by formula (L-6.1) to formula (L-6.9).
The kind of the compound which can be used in combination is not particularly limited. One to three kinds of compounds are preferably included or one to four kinds of compounds are more preferably included from these compounds. A wide molecular weight distribution of the compound to be selected is also effective to the solubility, for example, one kind of compound is selected from the compound represented by formula (L-6.1) or (L-6.2), one kind of compound is selected from the compound represented by formula (L-6.4) or (L-6.5), one kind of compound is selected from the compound represented by formula (L-6.6) or (L-6.7), one kind of compound is selected from the compound represented by formula (L-6.8) or (L-6.9), and these are preferably suitably combined. Among these, the compounds represented by formula (L-6.1), formula (L-6.3), formula (L-6.4), formula (L-6.6), and formula (L-6.9) are preferably included.
The compound represented by general formula (L-6) is, for example, preferably a compound represented by formula (L-6.10) to formula (L-6.17), and is preferably a compound represented by formula (L-6.11) among those.
The preferable lower limit value of the content of these compounds with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, or equal to or greater than 7% by mass. The preferable upper limit value of the content of these compounds is equal to or smaller than 20% by mass, equal to or smaller than 15% by mass, equal to or smaller than 13% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 9% by mass.
The compound represented by general formula (L-7) is the following compound.
In the formula, RL71 and RL72 each independently represent the same meaning as RL1 and RL2 in general formula (L), AL71 and AL72 each independently represent the same meaning as AL2 and AL3 in general formula (L), hydrogen atoms on AL71 and AL72 each may be independently substituted with fluorine atoms, ZL71 represents the same meaning as ZL2 in general formula (L), and XL71 and XL72 each independently represent a fluorine atom or a hydrogen atom.
In the formula, RL71 and RL72 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, AL71 and AL72 are each independently preferably a 1,4-cyclohexylene group or a 1,4-phenylene group, hydrogen atoms on AL71 and AL72 each may be independently substituted with fluorine atoms, ZL71 is preferably a single bond or COO— and preferably a single bond, and XL71 and XL72 are preferably a hydrogen atom.
The kind of the compound which can be used in combination is not particularly limited, and compounds are combined, in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, or a birefringence. The number of kind of the compound used is one, two, three, or four, in one embodiment, for example.
In the composition of the embodiment, it is necessary that the content of the compound represented by general formula (L-7) is suitably adjusted in accordance with required performance such as solubility at a low temperature, a transition temperature, electrical reliability, a birefringence, process suitability, dropping marks, burning, or dielectric anisotropy.
The preferable lower limit value of the content of the compound represented by formula (L-7) with respect to a total amount of the composition of the embodiment is equal to or greater than 1% by mass, equal to or greater than 2% by mass, equal to or greater than 3% by mass, equal to or greater than 5% by mass, equal to or greater than 7% by mass, equal to or greater than 10% by mass, equal to or greater than 14% by mass, equal to or greater than 16% by mass, or equal to or greater than 20% by mass. The preferable upper limit value of the content of the compound represented by formula (L-7) with respect to a total amount of the composition of the embodiment is equal to or smaller than 30% by mass, equal to or smaller than 25% by mass, equal to or smaller than 23% by mass, equal to or smaller than 20% by mass, equal to or smaller than 18% by mass, equal to or smaller than 15% by mass, equal to or smaller than 10% by mass, or equal to or smaller than 5% by mass.
In a case where the embodiment of the composition of the embodiment having a high Tni is desired, it is preferable to increase the content of the compound represented by formula (L-7), and in a case where the embodiment thereof having a low viscosity is desired, it is preferable to decrease the content thereof.
The compound represented by general formula (L-7) is preferably a compound represented by formula (L-7.1) to formula (L-7.4) and preferably a compound represented by formula (L-7.2).
The compound represented by general formula (L-7) is preferably a compound represented by formula (L-7.11) to formula (L-7.13), and preferably a compound represented by formula (L-7.11).
The compound represented by general formula (L-7) is a compound represented by formula (L-7.21) to formula (L-7.23). The compound is preferably a compound represented by formula (L-7.21).
The compound represented by general formula (L-7) is preferably a compound represented by formula (L-7.31) to formula (L-7.34), and preferably a compound represented by formula (L-7.31) and/or formula (L-7.32).
The compound represented by general formula (L-7) is preferably a compound represented by formula (L-7.41) to formula (L-7.44), and preferably a compound represented by formula (L-7.41) and/or formula (L-7.42).
The compound represented by general formula (L-7) is preferably a compound represented by formula (L-7.51) to formula (L-7.53).
The liquid crystal composition further includes a polymerizable compound. The polymerizable compound may be a well-known polymerizable compound used for the liquid crystal composition. As an example of the polymerizable compound, a compound represented by general formula (P):
is used.
In the formula (P), Zp1 represents a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, in which a hydrogen atom may be substituted with a halogen atom, an alkoxy group having 1 to 15 carbon atoms, in which a hydrogen atom may be substituted with a halogen atom, an alkenyl group having 1 to 15 carbon atoms, in which a hydrogen atom may be substituted with a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms, in which a hydrogen atom may be substituted with a halogen atom, or —SPp2-RP2, RP1 and RP2 represent any of formula (R-I) to formula (R-IX):
In the formulae, bonding to SpP1 is performed at *, R2 to R6 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, W represents a single bond, —O—, or a methylene group, T represents a single bond or —COO—, p, t, and q each independently represent 0, 1, or 2), SpP1 and SpP2 represent a spacer group, LP1 and LP2 each independently represent a single bond, —O—, —S—, —CH2—, —OCH2—, —CH2O—, —CO—, —C2H4—, —COO—, —OCO—, —OCOOCH2—, —CH2OCOO—, —OCH2CH2O—, —CO—NR—, —NRa—CO—, —SCH2—, —CH2S—, —CH═CRa—COO—, —CH═CRa—OCO—, —COO—CRa═CH—, —OCO—CRa═CH—, —COO—CRa═CH—COO—, —COO—CRa═CH—OCO—, —OCO—CRa═CH—COO—, —OCO—CRa═CH—OCO—, —(CH2)z—C(═O)—O—, —(CH2)z—O— (C═O)—, —O— (C═O)—(CH2)z—, —(C═O)—O—(CH2)z—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF2—, —CF2O—, —OCF2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, or —C≡C— (in the formulae, Ra's each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z represents an integer of 1 to 4), MP2 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, an indane-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 1,3-dioxane-2,5-diyl group, or a single bond, MP2 may be unsubstituted or substituted with an alkyl group having 1 to 12 carbon atoms, a halrogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or —RP1, MP1 represents any of the following formulae (i-11) to (ix-11):
In the formulae, bonding to SPP1 is performed at * and bonding to LP1, LP2, or ZP1 is performed at **), any hydrogen atom on MP1 may be substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or —RP1, MP3 represents any of formulae (i-13) to (ix-13):
In the formulae, bonding to ZP1 is performed at * and bonding to LP2 is performed at **), any hydrogen atom on MP3 may be substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or —RP1, mP2 to mP4 each independently represent 0, 1, 2, or 3, mP1 and mP5 each independently represent 1, 2, or 3, when a plurality of ZP1's are present, these may be the same or different, when a plurality of RP1's are present, these may be the same or different, when a plurality of RP2's are present, these may be the same or different, when a plurality of SpP1's are present, these may be the same or different, when a plurality of SpP2's are present, these may be the same or different, when a plurality of LP1's are present, these may be the same or different, and when a plurality of MP2's are present, these may be the same or different.
In a case where the liquid crystal composition of the embodiment further includes the polymerizable compound, in addition to the compound (i), a pretilt angle of the liquid crystal molecule can be suitably formed.
It is preferable that the composition of the embodiment does not include a compound having a structure in which oxygen atoms are not bonded to each other, such as a peroxy acid (—CO—OO—) structure in a molecule.
In a case where the reliability and long-term stability of the composition are important, the content of the compound having a carbonyl group with respect to a total mass of the composition is preferably equal to or smaller than 5% by mass, more preferably equal to or smaller than 3% by mass, even more preferably equal to or smaller than 1% by mass, and most preferably substantially no compound is included.
In a case where stability due to UV irradiation is important, the content of the compound in which a chlorine atom is substituted, with respect to a total mass of the composition is preferably equal to or smaller than 15% by mass, preferably equal to or smaller than 10% by mass, preferably equal to or smaller than 8% by mass, preferably equal to or smaller than 5% by mass, preferably equal to or smaller than 3% by mass, and preferably substantially no compound is included.
An increase in content of the compound in which all ring structures in the molecule are 6-membered rings, is preferable, and the content of the compound in which all ring structures in the molecule are 6-membered rings, with respect to a total mass of the composition is preferably equal to or greater than 80% by mass, more preferably equal to or greater than 90% by mass, even more preferably equal to or greater than 95% by mass, and most preferably the composition is substantially configured with only the compound in which all ring structures in the molecule are 6-membered rings.
In order to prevent a deterioration due to oxidation of the composition, a decrease in content of the compound having a cyclohexenylene group as the ring structure is preferable, and the content of the compound having a cyclohexenylene group with respect to a total mass of the composition is preferably equal to or smaller than 10% by mass, preferably equal to or smaller than 8% by mass, preferably equal to or smaller than 5% by mass, preferably equal to or smaller than 3% by mass, and more preferably substantially no compound is included.
In a case where the improvement of viscosity and the improvement of Tni are important, a decrease in content of the compound having a 2-methylbenzene-1,4-diyl group, in which a hydrogen atom may be substituted with halogen, in a molecule is preferable, and the content of the compound having a 2-methylbenzene-1,4-diyl group in a molecule with respect to a total mass of the composition is preferably equal to or smaller than 10% by mass, preferably equal to or smaller than 8% by mass, preferably equal to or smaller than 5% by mass, preferably equal to or smaller than 3% by mass, and more preferably substantially no compound is included.
The expression that substantially no compound is included in the specification means that no compound is included excluding substances which are unintentionally included (inevitable impurities).
A lower limit value of an average elastic coefficient (KAVG) of the liquid crystal composition is preferably equal to or greater than 10, preferably equal to or greater than 10.5, preferably equal to or greater than 11, preferably equal to or greater than 11.5, preferably equal to or greater than 12, preferably equal to or greater than 12.3, preferably equal to or greater than 12.5, preferably equal to or greater than 12.8, preferably equal to or greater than 13 preferably equal to or greater than 13.3, preferably equal to or greater than 13.5, preferably equal to or greater than 13.8, preferably equal to or greater than 14, preferably equal to or greater than 14.3, preferably equal to or greater than 14.5, preferably equal to or greater than 14.8, preferably equal to or greater than 15, preferably equal to or greater than 15.3, preferably equal to or greater than 15.5, preferably equal to or greater than 15.8, preferably equal to or greater than 16, preferably equal to or greater than 16.3, preferably equal to or greater than 16.5, preferably equal to or greater than 16.8, preferably equal to or greater than 17, preferably equal to or greater than 17.3, preferably equal to or greater than 17.5, preferably equal to or greater than 17.8, or preferably equal to or greater than 18. The upper limit value of the average elastic coefficient (KAVG) of the liquid crystal composition is preferably equal to or smaller than 25, preferably equal to or smaller than 24.5, preferably equal to or smaller than 24, preferably equal to or smaller than 23.5, preferably equal to or smaller than 23, preferably equal to or smaller than 22.8, preferably equal to or smaller than 22.5, preferably equal to or smaller than 22.3, preferably equal to or smaller than 22, preferably equal to or smaller than 21.8, preferably equal to or smaller than 21.5, preferably equal to or smaller than 21.3, preferably equal to or smaller than 21, preferably equal to or smaller than 20.8, preferably equal to or smaller than 20.5, preferably equal to or smaller than 20.3, preferably equal to or smaller than 20, preferably equal to or smaller than 19.8, preferably equal to or smaller than 19.5, preferably equal to or smaller than 19.3, preferably equal to or smaller than 19, preferably equal to or smaller than 18.8, preferably equal to or smaller than 18.5, preferably equal to or smaller than 18.3, preferably equal to or smaller than 18, preferably equal to or smaller than 17.8, preferably equal to or smaller than 17.5, preferably equal to or smaller than 17.3, or preferably equal to or smaller than 17. In a case where power consumption reduction is important, it is effective to prevent a light intensity of a backlight, and it is preferable to improve transmittance of light of the liquid crystal display element. Accordingly, a value of KAVG is preferably set to be low. In a case where the improvement of response speed is important, the value of KAVG is preferably set to be high.
(Liquid Crystal Display Element)
The liquid crystal composition of the embodiment is applied to the liquid crystal display element. Hereinafter, an example of the liquid crystal display element according to the embodiment will be described suitably with reference to
A pixel electrode layer 5 is formed on a surface of the first substrate 2 on a side of the liquid crystal layer 4. A common electrode layer 6 is provided on the second substrate 3 on a side of the liquid crystal layer 4. The first substrate 2 and the second substrate 3 may be interposed between a pair of polarizing plates 7 and 8. A color filter 9 may be further provided on the second substrate 3 on a side of the liquid crystal layer 4.
That is, the liquid crystal display element 1 according to the embodiment has a configuration in which the first polarizing plate 7, the first substrate 2, the pixel electrode layer 5, the liquid crystal layer 4 including the liquid crystal composition, the common electrode layer 6, the color filter 9, the second substrate 3, and the second polarizing plate 8 are laminated in this order.
The first substrate 2 and the second substrate 3 are formed of, for example, a material having flexibility such as glass or plastic. At least one of the first substrate 2 and the second substrate 3 is formed of a transparent material, and the other one thereof may be formed of a transparent material or may be formed of an opaque material such as metal or silicon. The first substrate 2 and the second substrate 3 are bonded to each other with a sealing material such as an epoxy-based thermosetting composition disposed in a peripheral region, and in order to maintain a distance between the substrates, for example, a particulate spacer such as glass particles, plastic particles, or alumina particles, or a spacer column formed of a resin formed by a photolithographic method may be disposed therebetween.
Regarding the first polarizing plate 7 and the second polarizing plate 8, a polarizing axis of each polarizing plate can be adjusted to adjust a viewing angle or contrast to be excellent, and the polarizing plates preferably have transmission axes orthogonal to each other, so that the transmission axes are operated in a normally black mode. Particularly, any one of the first polarizing plate 7 and the second polarizing plate 8 is preferably disposed so as to have a transmission axis parallel to an alignment direction of liquid crystal molecules, in a case where no voltage is applied.
Regarding the color filter 9, from a viewpoint of preventing leakage of light, a black matrix is preferably formed, and a black matrix (not shown) is preferably formed on a portion corresponding to a thin film transistor.
The black matrix may be installed on a substrate on a side opposite to an array substrate with the color filter, may be installed on the array substrate side with the color filter, or the black matrix may be installed on the array substrate and the color filter may be provided the other substrate, separately. In addition, the black matrix may be installed separately from the color filter, and transmittance may be decreased by overlapping each color of the color filter.
A unit pixel of the liquid crystal display element is formed by the region surrounded by the plurality of gate bus lines 11 and the plurality of data bus lines 12, and a pixel electrode 13 is formed in the unit pixel. The pixel electrode 13 has a so-called fishbone structure including two stem portions orthogonal to each other to form a cross shape, and a plurality of branch portions extending from each stem portion. A Cs electrode 14 is provided substantially in parallel to the gate bus line 11 between the pair of the gate bus lines 11 and 11. In addition, a thin film transistor including a source electrode 15 and a drain electrode 16 is provided in the vicinity of an intersection where the gate bus line 11 and the data bus line 12 intersect each other. In the drain electrode 16, a contact hole 17 is provided.
Each of the gate bus line 11 and the data bus line 12 is preferably formed of a metal film, more preferably formed of Al, Cu, Au, Ag, Cr, Ta, Ti, Mo, W, Ni, or an alloy thereof, and even more preferably formed of Mo, Al, or an alloy thereof.
The pixel electrode 13 is preferably a transparent electrode, in order to improve transmittance. The transparent electrode is formed of an oxide semiconductor (ZnO, InGaZnO, SiGe, GaAs, IZO (Indium Zinc Oxide), ITO (Indium Tin Oxide), SnO, TiO, AZTO (AlZnSnO), or the like) by sputtering or the like. In this case, a film thickness of the transparent electrode may be 10 to 200 nm. In addition, in order to decrease electrical resistance, the transparent electrode can also be formed as a polycrystal ITO film, by firing an amorphous ITO film.
In the liquid crystal display element of the embodiment, for example, a wiring can be formed on the first substrate 2 and the second substrate 3 by sputtering a metal material such as Al or an alloy thereof, and the pixel electrode layer 5 and the common electrode layer 6 can be respectively formed. In addition, the color filter 9 can be formed, for example, by a pigment dispersion method, a printing method, an electrodeposition method, or a dyeing method. As an example of a forming method of the color filter by the pigment dispersion method, a curable colored composition for a color filter is applied on the transparent substrate, subjected to a patterning treatment, and cured by heating or light irradiation. By performing this step with respect to each of three colors of red, green, blue, a pixel portion for the color filter can be formed. In addition, the color filter 9 may be installed on a side of a substrate including a TFT or the like.
The first substrate 2 and the second substrate 3 face each other so that the pixel electrode layer 5 and the common electrode layer 6 respectively become the inner side thereof, and in this case, the interval between the first substrate 2 and the second substrate 3 may be adjusted through a spacer. In this case, a thickness of the liquid crystal layer 4 is preferably adjusted, for example, to be 1 to 100 μm.
In a case of using the polarizing plates 7 and 8, the sum of a refractive index anisotropy Δn of the liquid crystal layer 4 and the thickness of the liquid crystal layer 4 are preferably adjusted so that the contrast becomes the maximum. In addition, in a case where two polarizing plates 7 and 8 are present, the polarizing axis of each polarizing plate can be adjusted so as to adjust a viewing angle or contrast to be excellent. Further, a retardation film for increasing the viewing angle can also be used. After that, a sealing agent such as an epoxy-based thermosetting composition is screen-printed on the substrates, in a state where a liquid crystal injection port is provided, the substrates are bonded to each other and heated for heat curing of the sealing agent.
As the method for interposing the composition between the two substrates 2 and 3, a typical vacuum injection method or a one drop fill (ODF) method can be used. In the vacuum injection method, dropping marks are not generated, but marks of injection remain. In the embodiment, a display element manufactured by the ODF method can be suitably used. In the manufacturing step of the liquid crystal display element of the ODF method, a sealing agent such as an epoxy-based thermosetting composition is drawn on any one substrate of a back plane and a front plane in a closed loop back shape, a predetermined amount of the composition is added dropwise therein under deaeration, and the front plane and the back plane are bonded to each other, and accordingly, the liquid crystal display element can be manufactured. In the embodiment, the generation of dropping marks in a case where the liquid crystal composition is added dropwise on the substrate can be prevented in the ODF method. The dropping mark is defined as a phenomenon in which a white mark of the dropped liquid crystal composition is generated in a case of black display.
In the manufacturing step of the liquid crystal display element by the ODF method, it is necessary that the optimal liquid crystal injection amount is added dropwise in accordance with a size of the liquid crystal display element, but regarding the liquid crystal composition of the embodiment, the liquid crystal can be can be continuously stably added dropwise for a long period of time, without an effect with respect to rapid pressure change or impact in a dropping device occurring in a case of liquid crystal dropping, for example, and accordingly, it is also possible to maintain a high yield of the liquid crystal display element. Particularly, a small liquid crystal display element widely used for a smart phone which is the latest trend has a small degree of optimal liquid crystal injection amount, and accordingly, it is difficult to prevent a shift from the optimal value in a certain range. However, by using the liquid crystal composition of the embodiment, a stable discharge amount of a liquid crystal material can be realized even in the small liquid crystal display element.
In a case where the liquid crystal composition of the embodiment includes the polymerizable compound, as a method of polymerizing the polymerizable compound, a method of performing the polymerization by emitting an active energy ray such as an ultraviolet ray or an electron ray singly, in combination, or in order is preferable, because a suitable polymerization speed is desired for obtaining excellent alignment performance of the liquid crystal. In a case of using an ultraviolet ray, a polarizing light source may be used or a non-polarizing light source may be used. In a case of performing the polarization in a state where the polymerizable compound-containing composition is interposed between the two substrates, it is necessary that at least the substrate on the irradiated surface side applies suitable transparency to the active energy ray. A method of polymerizing only a specific portion using a mask in a case of the light irradiation, changing the alignment state of the non-polymerized portion by changing the conditions such as an electric field, a magnetic field, or a temperature, and further emitting the active energy ray for the polymerization may be used. Particularly, in a case of the ultraviolet light exposure, the ultraviolet light exposure is preferably performed while applying an AC electric field to the polymerizable compound-containing composition. Regarding the AC electric field to be applied, AC is preferable at a frequency of 10 Hz to 10 kHz and more preferable at a frequency of 60 Hz to 10 kHz, and a voltage is selected depending on a desired pretilt angle of the liquid crystal display element. That is, it is possible to control the pretilt angle of the liquid crystal display element by the voltage to be applied. In a horizontal field type MVA mode liquid crystal display element, the pretilt angle is preferably controlled to be 80 degrees to 89.9 degrees, from viewpoints of alignment stability and contrast.
A temperature of the irradiation is preferably in a temperature range in which the liquid crystal state of the composition of the embodiment is maintained. The polymerization is preferably performed at a temperature close to the room temperature, that is, typically a temperature of 15° C. to 35° C. As a lamp for generating the ultraviolet ray, a metal halide lamp, a high pressure mercury lamp, or a super high pressure mercury lamp can be used. In addition, regarding the wavelength of the ultraviolet ray to be emitted, the ultraviolet ray in a wavelength region which is not in an absorption wavelength region of the composition is preferably emitted, and the ultraviolet ray is preferably cut and used, if necessary. An intensity of the ultraviolet ray to be emitted is preferably 0.1 mW/cm2 to 100 mW/cm2, and more preferably 2 mW/cm2 to 50 mW/cm2. The energy amount of the ultraviolet ray to be emitted can be suitably adjusted, and is preferably 10 mJ/cm2 to 500 J/cm2, and more preferably 100 mJ/cm2 to 200 J/cm2. In a case of emitting the ultraviolet ray, the intensity may be changed. The time for emitting the ultraviolet ray is suitably selected in accordance with the intensity of the ultraviolet ray, and is preferably 10 seconds to 3,600 seconds and more preferably 10 seconds to 600 seconds.
In the liquid crystal composition of the embodiment, the compound (i) does not inhibit the polymerization reaction of the polymerizable compound, and accordingly, the polymerizable compounds can be suitably polymerized and the generation of the unreacted polymerizable compound remaining in the liquid crystal composition can be prevented.
In a case where the compound (ii) is used as the polymerizable compound, the liquid crystal display element 1 to be obtained includes the two substrate 2 and 3, and the liquid crystal layer 4 including the liquid crystal composition provided between the two substrates 2 and 3 and the polymer of the compound represented by general formula (ii). In this case, the polymer of the compound represented by general formula (ii) is considered to be unevenly distributed on the sides of the substrates 2 and 3 in the liquid crystal layer 4.
The liquid crystal display element 1 may be a liquid crystal display element for active matrix driving. The liquid crystal display element 1 may be a PSA type, PSVA type, VA type, IPS type, FFS type, or ECB type liquid crystal display element, and is preferably a PSA type liquid crystal display element.
In the liquid crystal display element of the embodiment, the liquid crystal composition including the compound (i) is used, and accordingly, it is not necessary to provide an alignment film such as a polyimide alignment film on the liquid crystal layer 4 side of the first substrate 2 and the second substrate 3. That is, the liquid crystal display element of the embodiment can have a configuration in which at least one of the two substrates is not provided with any alignment film such as a polyimide alignment film.
Hereinafter, the invention is further described in detail with reference to examples, but the invention is not limited to the examples.
50 g of 5-bromosalicylaldehyde, 75 g of (2,2-dimethyl ethyl-1,3-dioxane-5-yl) methyl mesylate, 35 g of potassium carbonate, and 500 ml of N, N-dimethylformamide were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and a reaction was carried out at 90° C. for 5 hours. After completing the reaction, the resultant material was cooled, 1 L of ethyl acetate was added, an organic layer was washed with water or a saturated saline solution, a solvent was distilled, and 67 g of a compound represented by (1) was obtained.
Next, 59 g of 4-(8-octyloxy)-3-fluorophenylboronic acid, 60 g of the compound (1), 42 g of potassium carbonate, 1.8 g of tetrakistriphenyl phosphine palladium, 200 mL of tetrahydrofuran, and 100 ml of water were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and a reaction was carried out at 70° C. for 5 hours. After completing the reaction, the resultant material was cooled, a 10% hydrochloric acid was added, and a target material was extracted by ethyl acetate. The organic layer was washed with water or a saturated saline solution, and the solvent was distilled. After that, dispersion washing with toluene and purification with an alumina column were performed, and 74 g of a compound represented by formula (2) was obtained.
2 g of sodium borohydride and 20 ml of ethanol were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled approximately at 10° C. After that, a THF solution (200 ml) of 47 g of the compound (2) was slowly added dropwise. After completing the reaction, a saturated aqueous ammonium chloride solution was slowly added, and washing was performed with 400 ml of ethyl acetate, water, or a saturated saline solution. By distilling the solvent and performing the purification with an alumina column, 42 g of a compound represented by (3) was obtained.
Next, 42 g of the compound (3), 12 g of triethylamine, and 300 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled to 10° C. or lower. After that, 12 g of methacryloyl chloride was slowly added dropwise. After completing the dropwise addition, the temperature of the reaction vessel was returned to room temperature, and the reaction was carried out for 3 hours. After completing the reaction, water was slowly added, and washing was carried out with 400 ml of dichloromethane, water, or a saturated saline solution. By distilling the solvent and performing the purification with an alumina column, 38 g of a compound represented by (4) was obtained.
After that, the compound (4) and 100 ml of THF were added to a reaction vessel including a stirring device and a thermometer, and 20 ml of a 10% hydrochloric acid was slowly added dropwise. After completing the reaction, the resultant material was cooled and a target material was extracted by ethyl acetate. The organic layer was washed with water or a saturated saline solution, and the solvent was distilled. After that, dispersion washing with toluene and purification with an alumina column were performed, and 31 g of a compound represented by formula (5) was obtained.
31 g of the compound (5) and 400 ml of dichloromethane were added to a reaction vessel including a stirring device and a thermometer, and the reaction vessel was cooled to 10° C. or lower. Next, 14 g of ethyl chloroformate was slowly added dropwise. After completing the dropwise addition, the resultant material was stirred for 30 minutes. Then, 18 g of triethylamine was added dropwise. After completing the reaction, the organiclayer was washedwithwater or a saturated saline solution, and the solvent was distilled. Then, the purification with a silica column was performed, 26 g of a target compound represented by a compound (6) was obtained.
(Physical Properties)
Melting point: 81° C.
1H-NMR (solvent: heavy chloroform): δ: 0.88 (t, 3H), 1.29-1.31 (m, 6H), 1.44-1.49 (m, 2H), 1.56 (s, 3H), 1.83 (q, 2H), 1.97 (s, 2H), 2.69-2.76 (m, 1H), 4.05 (t, 2H), 4.16 (d, 2H), 4.35-4.38 (m, 2H), 4.59-4.62 (m, 2H), 5.28 (s, 2H), 5.60 (s, 1H), 6.14 (s, 1H), 6.90 (d, 1H), 7.01 (t, 1H), 7.21-7.29 (m, 2H), 7.46 (dd, 1H), 7.53 (d, 1H)
13C-NMR (solvent: heavy chloroform): δ: 14.9, 17.3, 22.7, 25.9, 27.9, 29.6, 31.8, 64.0, 68.7, 68.8, 72.8, 114.7, 122.3, 125.6, 128.4, 135.5, 138.6, 151.0, 158.3, 166.0
16 g of 3-(3,4-bis (methacryloyloxy) phenyl) propionic acid, 15 g of 4′-((2,2-dimethyl-1,3-dioxane-5-yl) methoxy)-[1,1′-biphenyl]-4-ol, 500 mg of dimethylaminopyridine, and 200 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled to 10° C. or lower. After that, 8 g of diisopropylcarbodiimide was slowly added dropwise. After completing the dropwise addition, the reaction was carried out at room temperature for 5 hours. After completing the reaction, the organic layer was washed with water or a saturated saline solution, and the solvent was distilled. Then, 150 ml of tetrahydrofuran (THF) was added, and 20 ml of a 10% hydrochloric acid was slowly added dropwise. After completing the reaction, the resultant material was cooled and a target material was extracted by ethyl acetate. The organic layer was washed with water or a saturated saline solution, and the solvent was distilled. After that, dispersion washing with toluene and purification with an alumina column were performed, and 21 g of a compound represented by formula (7) was obtained.
(Physical Properties)
Melting point: 121° C.
10 g of the compound (7) and 300 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled to 10° C. or lower. Then, 5.6 g of ethyl chloroformate was slowly added dropwise. After completing the dropwise addition, the resultant material was stirred for 30 minutes. Then, 5.7 g of triethylamine was added dropwise. After completing the reaction, the organic layer was washed with water or a saturated saline solution, and the solvent was distilled. After that, the purification with a silica column was performed, 8.5 g of a target compound represented by a compound (8) was obtained.
(Physical Properties)
Melting point: 102° C.
1H-NMR (solvent: heavy chloroform): δ: 1.56 (s, 3H), 1.95 (t, 2H), 2.20 (t, 2H), 2.69-2.76 (m, 1H), 4.05 (m, 2H), 4.16 (m, 4H), 5.60 (s, 2H), 6.14 (s, 2H), 6.87-6.99 (m, 3H), 7.05 (s, 1H), 7.21-7.29 (m, 3H), 7.43 (d, 2H), 7.55 (d, 2H)
13C-NMR (solvent: heavy chloroform): δ: 17.3, 27.9, 29.6, 68.7, 68.8, 72.8, 109.5, 114.7, 122.3, 125.6, 128.4, 128.3, 129.4, 135.5, 138.6, 151.0, 158.3, 159.7, 166.0
10 g of 5-bromosalicylaldehyde, 1 g of pyridinium paratoluenesulfonate, and 100 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, 20 ml of a dichloromethane solution of 10 g of 3,4-dihydro-2H pyran was added dropwise at room temperature, and a reaction was carried out for 5 hours. After completing the reaction, the organic layer was washed with water or a saturated saline solution, the solvent was distilled, and 12 g of a compound represented by formula (9) was obtained.
Then, a compound represented by Compound formula (10) shown below was obtained by the same method as in Example 1.
10 g of the compound (10) and 100 ml of THF were added to a reaction vessel including a stirring device and a thermometer, and 5 ml of a 10% hydrochloric acid/5 ml of methanol was slowly added dropwise. After completing the reaction, a target material was extracted by ethyl acetate. The organic layer was washed with water or a saturated saline solution, and the solvent was distilled. After that, dispersion washing with toluene and purification with an alumina column were performed, and 8 g of a compound represented by formula (11) was obtained.
15 g of sesamol, 14 g of 2-chloroethanol, 28 g of triphenylphosphine, and 200 ml of THF were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled to 10° C. or lower. 22 g of diisopropylazodicarboxylate was slowly added dropwise. After completing the dropwise addition, the temperature of the reaction vessel was returned to room temperature, and the reaction was carried out for 5 hours. After completing the reaction, the resultant material was cooled, 200 ml of ethyl acetate was added, the organic layer was washed with water or a saturated saline solution, the solvent was distilled, and 17 g of a compound represented by formula (12) was obtained.
17 g of the compound (12), 57 g of gallic acid tertiary butyl ester, 50 g of potassium carbonate, and 500 ml of N, N-dimethylformamide were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and a reaction was carried out at 90° C. for 5 hours. After completing the reaction, the resultant material was cooled, 400 ml of ethyl acetate was added, the organic layer was washed with water or a saturated saline solution, and the solvent was distilled. The obtained compound was dissolved with 200 ml of dichloromethane and 200 ml of formic acid, and a reaction was carried out with heating and refluxing for 5 hours. The reaction vessel was cooled to room temperature, 300 ml of pure water was added, and crystals were precipitated. The precipitated crystal was dissolved in 200 ml of THF and 400 ml of ethyl acetate, the organic layer water or a saturated saline solution, the solvent was distilled, and 42 g of a compound represented by formula (13) was obtained.
8 g of the compound (11), 12.8 g of the compound (13), 200 mg of dimethylaminopyridine, and 200 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled approximately at 10° C. After that, 2.6 g of diisopropylcarbodiimide was slowly added dropwise. After completing the dropwise addition, the reaction was carried out at room temperature for 5 hours. After completing the reaction, the organic layer was washed with water or a saturated saline solution, and the solvent was distilled. After that, the purification with a silica gel column was performed, and 16 g of a target compound represented by Compound (14) was obtained.
(Physical Properties)
Oily Compound
1H-NMR (solvent: heavy chloroform): δ: 1.76 (s, 6H), 4.12 (t, 12H), 4.84 (s, 2H), 5.47 (s, 3H), 5.60 (s, 1H), 6.14 (s, 1H), 6.90-7.02 (m, 9H), 7.15-7.29 (m, 4H), 7.35 (s, 1H), 7.65-7.82 (m, 4H)
13C-NMR (solvent: heavy chloroform): δ: 17.3, 62.9, 68.7, 68.8, 72.8, 101.4, 109.5, 114.7, 122.3, 125.6, 128.4, 128.3, 135.5, 138.6, 158.3, 159.7, 166.0
20 g of 3-bromo-4′-(dodecyloxy)-3′-fluoro-(1,1′-biphenyl)-4-ol, 0.5 g of pyridinium paratoluenesulfonate, and 100 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, 20 ml of a dichloromethane solution of 8 g of 3,4-dihydro-2H pyran were added dropwise at room temperature, and the reaction was carried out for 5 hours. After completing the reaction, the organic layer was washed with water or a saturated saline solution, the solvent was distilled, and 28 g of a compound represented by formula (15) was obtained.
Then, 28 g of the compound (15), 1 g of copper iodide, 3 g of tetrakistriphenylphosphine palladium, 200 ml of tetrahydrofuran, and 100 ml of pure water were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the resultant material was stirred at room temperature. After that, 33 g of 2-ethanolamine was added dropwise, the reaction vessel was heated to 60° C., and 5 g of propargyl alcohol was slowly added dropwise. After completing the reaction, the resultant material was cooled, 300 ml of toluene was added to the reaction solution, washing was performed with a saturated aqueous ammonium chloride solution or a saturated saline solution, and the solvent was distilled. Then, the resultant material was dissolved in dichloromethane, the purification with an alumina column and recrystallization with methanol were performed, and 21 g of a compound represented by formula (16) was obtained.
21 g of the compound (16), 1 g of 5% palladium carbon, 100 ml of tetrahydrofuran, and 20 ml of ethanol were added to an autoclave vessel including a stirring device, a reduction reaction (room temperature, 8 hours) was carried out with hydrogen of 0.3 MPa. After filtering the reaction solution, the reaction solvent was distilled, and 20 g of a compound represented by formula (17) was obtained.
Then, 20 g of the compound represented by formula (17), 4.6 g of triethylamine, and 100 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled to 5° C. or lower under a nitrogen gas atmosphere. Then, 5 g of methacrylic acid chloride was slowly added dropwise. After completing the dropwise addition, the reaction was carried out at a temperature of 20° C. or lower for 3 hours. After completing the reaction, dichloromethane was added, and the organic layer was washed with pure water or a saturated saline solution. After distilling the solvent, the resultant material was dissolved in 100 ml of tetrahydrofuran. The tetrahydrofuran solution was moved to the reaction vessel including a stirring device, 10 ml of a methanol solution to which 0.5 ml of hydrochloric acid was slowly added, and the reaction was carried out for 2 hours. After completing the reaction, the resultant material was washed with 400 ml of ethyl acetate, water, or a saturated saline solution. After distilling the solvent, 16 g of a compound represented by formula (18) was obtained by the purification with a silica gel column.
16 g of the compound represented by formula (18), 11 g of triphenylphosphine, 5 g of 5-(hydroxymethyl)-1, 3-dioxane-2-one, and 100 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled to 5° C. or lower. After that, 8.2 g of diisopropyl diazocarboxylate (DIAD) was added dropwise. After completing the dropwise addition, the resultant material was stirred at room temperature for 5 hours, and the reaction was completed. After completing the reaction, 200 ml of dichloromethane was added, and the organic layer was washed with pure water or a saturated saline solution. After distilling the solvent, 13 g of a target compound represented by Compound (19) was obtained by the purification with a silica gel column and the recrystallization with methanol.
(Physical Properties)
Melting point: 55° C.
1H-NMR (solvent: heavy chloroform): δ: 0.88 (t, 3H), 1.44-1.49 (m, 2H), 1.51-1.56 (m, 2H), 1.81-1.85 (m, 2H), 1.98 (s, 3H), 2.02-2.03 (m, 2H), 2.73-2.78 (m, 3H), 4.05 (t, 2H), 4.12 (d, 2H), 4.21 (t, 2H), 4.47 (m, 2H), 4.59 (m, 2H), 5.56 (s, 1H), 6.09 (s, 1H), 6.83 (d, 1H), 7.02 (t, 1H), 7.19-7.27 (m, 4H), 7.32 (d, 1H), 7.34 (m, 1H)
13C-NMR (solvent: heavy chloroform): δ: 14.1, 18.3, 22.6, 25.9, 27.0, 28.9, 29.2, 29.3, 31.8, 64.2, 64.4, 69.0, 69.5, 111.2, 114.5, 115.1, 122.1, 125.4, 128.7, 130.4, 136.4, 138.6, 147.0, 149.5, 155.0, 167.0
18.5 g of 4-octylphenol, 12 g of ethylene glycol mono-tertiary butyl ether, 35 g of triphenylphosphine, and 300 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled to 5° C. or lower. After that, 22 g of DIAD was added dropwise. After completing the dropwise addition, the resultant material was stirred at room temperature for 5 hours, and the reaction was completed. After completing the reaction, 200 ml of dichloromethane was added, and the organic layer was washed with pure water or a saturated saline solution. After distilling the solvent, 23 g of a compound represented by formula (20) was obtained by the purification with a silica gel column.
23 g of the compound represented by formula (20) and 100 ml of methylene chloride were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, the reaction vessel was maintained at a temperature of 5° C. or lower in a cooling bath, and 50 ml of trifluoroacetic acid was slowly added dropwise. After completing the dropwise addition, the temperature of the reaction vessel was returned to room temperature, and the reaction was carried out for 1 hour. After completing the reaction, the reaction solution was cooled to 10° C. or lower, and 50 ml of pure water was slowly added. 150 ml of methylene chloride was added, the organic layer was washed with pure water, or a saturated sodium hydrogen carbonate 5% aqueous hydrochloric acid solution, further washed with a saturated saline solution, and the organic layer was dried with anhydrous sodium sulfate. The solvent was distilled, and 18 g of a compound represented by formula (21) was obtained.
Then, 9 g of the compound represented by formula (21), 18 g of 3,5-Difluoro-3′-iodo-4′-((2,2,5-trimethyl-1,3-dioxane-5-yl)-(1,1′-biphenyl)-4-ol, 12 g of triphenylphosphine, and 200 ml of dichloromethane were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was cooled to 5° C. After that, 9 g of DIAD was added dropwise. After completing the dropwise addition, the resultant material was stirred at room temperature for 5 hours, the reaction was completed. After completing the reaction, 200 ml of dichloromethane was added, and the organic layer was washed with pure water or a saturated saline solution. After distilling the solvent, 22 g of a compound represented by formula (22) was obtained by the purification with an alumina column.
Then, 22 g of the compound (22), 0.5 g of copper iodide, 1.5 g of tetrakistriphenylphosphine palladium, 200 ml of tetrahydrofuran, and 100 ml of pure water were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the resultant material was stirred at room temperature. After that, 18 g of 2-ethanolamine was added dropwise, the reaction vessel was heated to 60° C., and 2 g of propargyl alcohol was slowly added dropwise. After completing the reaction, the resultant material was cooled, 300 ml of toluene was added to a reaction solution, washed with a saturated aqueous ammonium chloride solution or a saturated saline solution, and the solvent was distilled. After that, the resultant material was dissolved in dichloromethane, and the purification with an alumina column and the recrystallization with methanol were performed. 1 g of 5% palladium carbon, 200 ml of tetrahydrofuran, and 40 ml of ethanol were added to an autoclave vessel including a stirring device, and a reduction reaction (40° C., 8 hours) was carried out with hydrogen of 0.3 MPa. After filtering the reaction solution, the reaction solvent was distilled, and 15.7 g of a compound represented by formula (23) was obtained.
15.7 g of the compound represented by formula (23), 3 g of methacrylic acid, 150 mg of dimethylaminopyridine, 150 mg of dimethylaminopyridine, and 100 ml of methylene chloride were added to a reaction vessel including a stirring device, a cooling device, and a thermometer, and the reaction vessel was maintained at a temperature of 5° C. or lower in a cooling bath, and 3.8 g of diisopropylcarbodiimide was slowly added dropwise under the nitrogen gas atmosphere. After completing the dropwise addition, the temperature of the reaction vessel was returned to room temperature, and the reaction was carried out for 5 hours. After filtering the reaction solution, the filtrate was concentrated, dissolved by adding 100 ml of tetrahydrofuran, and added to a reaction vessel including a stirring device, and 15 ml of 10% aqueous hydrochloric acid was added and stirred for 30 minutes. After that, the resultant material was washed with 400 ml of ethyl acetate, water, or a saturated saline solution, the solvent was distilled, and 12.5 g of a target compound represented by Compound (24) was obtained by the purification with a silica gel column.
(Physical Properties)
Oily Compound
1H-NMR (solvent: heavy chloroform): δ: 0.88 (t, 6H), 1.26-1.49 (m, 10H), 1.63 (m, 2H), 1.98 (s, 3H), 2.02-2.03 (m, 2H), 2.63-2.70 (m, 4H), 3.38-3.41 (m, 4H), 3.80 (s, 2H), 4.21 (t, 2H), 4.22 (m, 2H), 4.47-4.50 (m, 4H), 5.56 (s, 1H), 6.09 (s, 1H), 6.83 (d, 2H), 7.02 (t, 1H), 7.19-7.27 (m, 4H), 7.62 (m, 2H)
13C-NMR (solvent: heavy chloroform): δ: 14.1, 14.8, 18.3, 22.7, 26.3, 28.9, 29.3, 31.8, 34.2, 35.7, 41.4, 65.5, 67.4, 69.0, 70.2, 111.2, 114.5, 115.0, 124.9, 127.0, 129.6, 133.4, 136.0, 147.0, 149.5, 155.0, 167.0
Adjustment of Liquid Crystal Composition
In a case where the content of the composition configured with the following compounds at a mixing ratio:
was set as 100% by weight, a composition, to which 0.3% by weight of the following polymerizable compound (R-1-0) was added, was set as LC-1.
A nematic phase-isotropic liquid phase transition temperature (TNI) of LC-1 was set as 75° C., a solid phase-nematic phase transition temperature (TCN) was 33° C., a refractive index anisotropy (Δn) was 0.11, a dielectric anisotropy (Δε) was −2.8, and a rotational viscosity (γ1) was 98 mPa-s. All of the refractive index anisotropy (Δn), the dielectric anisotropy (Δε), and the rotational viscosity (γ1) are measurement results obtained at 25° C. (the same applies hereinafter).
0.3% by weight of a compound (P-J-1) corresponding to the compound (i)
was added to 100% by weight of LC-1100, and a liquid crystal composition was prepared.
A liquid crystal composition was prepared in the same manner as in Example 7, except that the following compounds were added to LC-1 with the added amount shown in Table 1, instead of the compound (P-J-1) with the added amount of 0.3% by weight.
A liquid crystal composition was prepared in the same manner as in Example 7, except that a composition LC-2, to which 0.3% by weight of the polymerizable compound (R-1-0) was added, in a case where the content of the composition configured with the following compounds at a mixing ratio:
was set as 100% by weight, was used, instead of the composition LC-1.
TNI of LC-2 was 81° C., TCN was −54° C., Δn was 0.11, Δε was −3.0, and γ1 was 95 mPa·s.
A liquid crystal composition was prepared in the same manner as in Example 25, except that additive compounds shown in Table 1 or Table 3 shown below were added to LC-2 with the added amount shown in Table 1 or Table 3, instead of the compound (P-J-1) with the added amount of 0.3% by weight in Example 25.
A liquid crystal composition was prepared in the same manner as in Example 7, except that additive compounds shown in Table 3, Table 5, Table 7, or Table 9 shown below were respectively added with the added amount corresponding to Table 3, Table 5, Table 7, or Table 9, instead of the compound (P-J-1) with the added amount of 0.3% by weight in Example 7.
A liquid crystal composition was prepared in the same manner as in Example 8, except that the amount of the additive compound 1 was set as the added amount shown in Table 12 and amount of the additive compound 2 shown in Table 12 was set as the added amount shown in Table 12, instead of the compound (P-J-1) with the added amount of 0.3% by weight in Example 8.
A liquid crystal composition was prepared in the same manner as in Example 7, except that the compound (P-J-1) was not used.
A liquid crystal composition was prepared in the same manner as in Example 7, except that the following compound was added to LC-1 or LC-2 with the added amount shown in Table 13, instead that 0.3% by weight of the compound (P-J-1) was added in Example 7.
Regarding each liquid crystal composition of the examples and the comparative examples, the following evaluation tests were performed. The result of each evaluation test of each liquid crystal composition was shown in Table 2, Table 4, Table 6, Table8, Table 10, and Table 12.
(Evaluation Test of Low-Temperature Stability)
The liquid crystal composition was filtered with a membrane filter (PTFE 13 mm-0.2 μm manufactured by Agilent Technologies), and left for 15 minutes under vacuum reduced pressure condition, and the removal of dissolved air was performed. This was washed with acetone, and 0.5 g thereof was weighed on a sufficiently dried vial, and left under a low temperature environment at −25° C. for 10 days. After that, the precipitate was visually observed and determined with two levels shown below.
A: Precipitate cannot be observed.
B: Precipitate can be observed.
(Evaluation Test 1 of Vertical Alignment)
A first substrate (common electrode substrate) which includes a transparent electrode layer formed of a transparent common electrode and a color filter and does not include an alignment film, and a second substrate (pixel electrode substrate) which includes a pixel electrode layer including a transparent pixel electrode driven with an active element and does not include an alignment film were prepared. The liquid crystal composition was added dropwise on the first substrate, and interposed on the second substrate, the sealing material was cured at normal pressure under condition at 110° C. for 2 hours, and a liquid crystal cell having a cell gap 3.2 μm was obtained. The vertical alignment and alignment unevenness such as dropping marks in this case were observed with a polarization microscope, and evaluated with four levels shown below.
A: Evenly vertically aligned over the entire surface including the end portions and the like.
B: Extremely slight alignment defect is obtained, but in an acceptable level.
C: A large number of alignment defect including the end portions and the like, and in an unacceptable level.
D: Alignment defect is significantly deteriorated.
(Evaluation Test of Pretilt Angle Formation)
While applying a rectangular AC wave at 10 V and 100 Hz to a liquid crystal cell used in the section of (Evaluation Test of Vertical Alignment), a UV light having illuminance of 100 m/cm2 at 365 nm was emitted for 200 seconds using a high pressure mercury lamp. After that, regarding the stability of white display, a physical external force was applied to the cell while applying the rectangular AC wave at 10 V and 100 Hz, the observation was performed in a crossed Nichol prism state, and evaluation was performed with four levels shown below.
A: Evenly vertically aligned over the entire surface including the end portions and the like.
B: Extremely slight alignment defect is obtained, but in an acceptable level.
C: A large number of alignment defect including the end portions and the like, and in an unacceptable level.
D: Alignment defect is significantly deteriorated.
(Evaluation Test of Remaining Monomer Amount)
The amount of the polymerizable compound (R1-1-1), after irradiating the cell used in the section of (Evaluation Test of Pretilt Angle Formation) with light of a UV fluorescent lamp manufactured by Toshiba Lighting and Technology Corporation for 60 minutes (illuminance of 1.7 mW/cm2 at 313 nm), was determined with HPLC, and the amount of the remaining monomer was determined. The evaluation was performed with four levels shown below, in accordance with the amount of the remaining monomer.
A: less than 300 ppm
B: equal to or greater than 300 ppm and less than 500 ppm
C: equal to or greater than 500 ppm and less than 1,500 ppm
D: equal to or greater than 1,500 ppm
(Evaluation Test of Response Properties)
The cell having a cell gap of 3.2 μm used in the section of (Evaluation Test of Pretilt Angle Formation) was irradiated with light of a UV fluorescent lamp manufactured by Toshiba Lighting and Technology Corporation for 60 minutes (illuminance of 1.7 mW/cm2 at 313 nm). The response speed was measured with respect to the cell obtained as described above. Regarding the response speed, Voff at 6 V was measured using DMS 703 manufactured by AUTRONIC-MELCHERS under the temperature condition of 25° C. The response properties were evaluated with four levels shown below.
A: less than 5 ms
B: equal to or greater than 5 ms and less than 15 ms
C: equal to or greater than 15 ms and less than 25 ms
D: equal to or greater than 25 ms
The above results show that the invention brings about advantageous effects.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2016-209592 | Oct 2016 | JP | national |
| 2017-109171 | Jun 2017 | JP | national |
This application is a continuation of U.S. application Ser. No. 16/340,798, filed on Apr. 10, 2019, which is a 371 of International Application No. PCT/JP2017/037481, filed on Oct. 17, 2017, which is based upon and claims the benefit of priority from the prior Japanese Patent Application No. 2016-209592, filed on Oct. 26, 2016 and No. 2017-109171, filed on Jun. 1, 2017.
| Number | Name | Date | Kind |
|---|---|---|---|
| 20140138581 | Archetti et al. | May 2014 | A1 |
| 20150252265 | Archetti et al. | Sep 2015 | A1 |
| 20170210994 | Lim et al. | Jul 2017 | A1 |
| Number | Date | Country |
|---|---|---|
| 106281363 | Jan 2017 | CN |
| 106281364 | Jan 2017 | CN |
| 2014-524951 | Sep 2014 | JP |
| 2015-168826 | Sep 2015 | JP |
| 6 447784 | Jan 2019 | JP |
| 201536898 | Oct 2015 | TW |
| 2016114093 | Jul 2016 | WO |
| 2017041893 | Mar 2017 | WO |
| Entry |
|---|
| International Search Report dated Jan. 16, 2018, issued in counterpart International Application No. PCT/JP2017/037481. |
| Non-Final Office Action dated Aug. 7, 2020, issued in U.S. Appl. No. 16/340,798. |
| Number | Date | Country | |
|---|---|---|---|
| 20210071084 A1 | Mar 2021 | US |
| Number | Date | Country | |
|---|---|---|---|
| Parent | 16340798 | US | |
| Child | 16950139 | US |
