WO2014168107A1 - Wavelength dispersion adjustment agent, resin composition, and method for adjusting wavelength dispersion of resin - Google Patents
Wavelength dispersion adjustment agent, resin composition, and method for adjusting wavelength dispersion of resin Download PDFInfo
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- WO2014168107A1 WO2014168107A1 PCT/JP2014/060080 JP2014060080W WO2014168107A1 WO 2014168107 A1 WO2014168107 A1 WO 2014168107A1 JP 2014060080 W JP2014060080 W JP 2014060080W WO 2014168107 A1 WO2014168107 A1 WO 2014168107A1
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- wavelength dispersion
- fluorene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Definitions
- the present invention provides an additive for imparting (or developing) reverse wavelength dispersibility to a resin or reducing the wavelength dispersibility of a resin, a resin composition containing the additive, and a wavelength of a resin using the additive.
- the present invention relates to a dispersion adjustment method.
- a compound having a fluorene skeleton (such as a 9,9-bisphenylfluorene skeleton) is known to have excellent functions such as a high refractive index and high heat resistance.
- fluorene compounds having a reactive group such as bisphenol fluorene (BPF), biscresol fluorene
- BPF bisphenol fluorene
- BCF bisphenoxyethanol fluorene
- BPEF bisphenoxyethanol fluorene
- Patent Document 1 discloses a molding material composed of a polyester resin having a 9,9-bisphenylfluorene skeleton.
- Patent Document 2 discloses a polyurethane resin having a 9,9-bisphenylfluorene skeleton and crosslinked with a crosslinking agent.
- 9,9-bis (4-hydroxyphenyl) fluorene or 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene (bisphenoxyethanol) is used as a part of the diol component constituting the resin. Fluorene skeleton is introduced into the resin.
- Patent Document 3 discloses a resin composition comprising a compound having a 9,9-bisphenylfluorene skeleton and a thermoplastic resin. This document describes that a compound having a 9,9-bisphenylfluorene skeleton can be added to a thermoplastic resin to impart a high refractive index to the thermoplastic resin.
- a transparent resin film is prepared by mixing 30 to 40 parts by weight of a specific compound (bisphenol fluorenediglycidyl ether, bisphenoxyethanol fluorene or bisphenoxyethanol fluoredenyl acrylate) with 100 parts by weight of a polycarbonate resin. And that the refractive index has increased.
- a specific compound bisphenol fluorenediglycidyl ether, bisphenoxyethanol fluorene or bisphenoxyethanol fluoredenyl acrylate
- Patent Document 4 discloses an optical resin composition composed of a transparent resin and a fluorene compound having a 9,9-bisarylfluorene skeleton. And this document describes that the birefringence can be reduced without impairing the mechanical properties and heat resistance of the transparent resin, and in a specific example, the fluorene-containing polyester resin is compared with the polycarbonate resin.
- Patent Document 5 discloses that a phenol compound functions as a nucleating agent ( ⁇ crystal nucleating agent) for forming a ⁇ crystal structure in a crystalline resin such as polylactic acid.
- ⁇ crystal nucleating agent a nucleating agent for forming a ⁇ crystal structure in a crystalline resin such as polylactic acid.
- ⁇ crystal nucleating agent a nucleating agent for forming a ⁇ crystal structure in a crystalline resin such as polylactic acid.
- 1 to 5% by weight of 9,9-bis (4-hydroxy-3-methylphenyl) fluorene was added to the ⁇ -crystal (melting point: 168 ° C.) poly-L lactic acid and melted. Kneading to obtain poly L-lactic acid in which ⁇ crystals (melting point: 163 ° C.) were formed, and Tg was changed from 56.5 ° C. to 60.9-62.1 ° C. as the crystal structure was changed. It is described that changed.
- JP 2012-211252 A discloses a film containing a cellulose derivative (such as cellulose triacetate) and a fluorene compound having a 9,9-bisarylfluorene skeleton (such as bisphenoxyethanol fluorene). ing. And in the Example of this document, it is described that the retardation value of the stretched film containing cellulose triacetate and bisphenoxyethanol fluorene was 0 or a negative value.
- the retardation film is an optical member having a function of converting transmitted light into circularly polarized light or elliptically polarized light by having birefringence.
- a retardation plate is used for display devices such as a liquid crystal display device for the purpose of color compensation, viewing angle expansion, antireflection, and the like.
- cellulose acetate, polycarbonate resin, annular Olefin resins are used as a material of the retardation plate.
- Such a retardation plate has flat chromatic dispersion characteristics (low wavelength dispersion), reverse wavelength dispersion or negative wavelength dispersion (phase difference (or birefringence) as the wavelength increases) from the viewpoint of display performance and the like. In some cases, it may be preferable to have a characteristic of increasing. However, the resin used as the material of the retardation plate as described above generally has a positive wavelength dispersion (a characteristic that the retardation (or birefringence) decreases as the wavelength increases). .
- Patent Document 7 describes a dicarboxylic acid component mainly composed of an alicyclic dicarboxylic acid component, a specific bisphenylfluorene-based compound (such as bisphenoxyethanol), and a fatty acid.
- a retardation film comprising a polyester resin obtained by reacting a diol component containing a cyclic diol compound and having a larger retardation at a wavelength of 450 to 630 nm on the longer wavelength side is disclosed.
- the raw material resin is limited to a specific polyester resin obtained using a very limited monomer component.
- JP 2002-284864 A (Claims, Examples) JP 2002-284834 A (Claims, Examples) Japanese Patent Laying-Open No. 2005-162785 (Claims and Examples) JP 2011-8017 A (Claims, Examples) Japanese Patent Laying-Open No. 2011-21083 (Claims and Examples) JP 2012-211252 A (Claims, Examples) JP 2007-213043 A (Claims, Examples)
- An object of the present invention includes an additive (or modifier) that can impart (or develop) reverse wavelength dispersion (negative wavelength dispersion) to a resin, or that can reduce the wavelength dispersion of a resin, and the additive. It is providing the wavelength dispersion adjustment method of resin using the resin composition and the said additive.
- the present inventors have intensively studied to solve the above problems, and as a result, the compound having a 9,9-bisarylfluorene skeleton is unexpectedly reversed wavelength dispersible in the resin.
- Has a function of adjusting the wavelength dispersion such that the wavelength dispersion of the resin can be reduced (or expressed), and such a compound has an excellent affinity for a wide range of resins.
- the inventors have found that wavelength dispersion can be easily adjusted for a wide range of resins, and completed the present invention.
- the additive of the present invention is an additive for imparting (or expressing) reverse wavelength dispersion (or negative wavelength dispersion) to the resin or reducing the wavelength dispersion of the resin, It is an additive composed of a compound having a 9-bisarylfluorene skeleton (reverse wavelength dispersion imparting agent, reverse wavelength dispersion improver, reverse wavelength dispersion control agent, wavelength dispersion adjusting agent, wavelength dispersion adjusting agent). .
- the additive of the present invention is an additive for bringing the wavelength dispersion of the resin close to the inverse wavelength dispersion (or negative wavelength dispersion) or reducing the wavelength dispersion of the resin, for example, It can be used as an additive for imparting (or expressing) the reverse wavelength dispersion (negative wavelength dispersion) to the resin, or improving the reverse wavelength dispersion of the resin.
- the compound having a 9,9-bisarylfluorene skeleton may be, for example, a compound represented by the following formula (1).
- ring Z is an aromatic hydrocarbon ring, R 1 and R 2 are substituents
- X is a group — [(OR 3 ) nY] (wherein Y is a hydroxyl group, mercapto group, glycidyl An oxy group or a (meth) acryloyloxy group, R 3 is an alkylene group, n is an integer of 0 or more) or an amino group, k is an integer of 0 to 4, m is an integer of 0 or more, and p is 1 or more Indicates an integer].
- the compound having a 9,9-bisarylfluorene skeleton may be a compound represented by the following formula (1A).
- the ring Z may be a benzene ring or a naphthalene ring
- R 1 may be an alkyl group
- k may be 0 to 1
- R 2 May be an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkoxy group
- m may be 0-2
- R 3 may be a C 2-4 alkylene group
- n is It may be 0-2
- p may be 1-3.
- Compounds having a 9,9-bisarylfluorene skeleton typically include 9,9-bis (hydroxyphenyl) fluorene, 9,9-bis (alkyl-hydroxyphenyl) fluorene, 9,9-bis (aryl- Hydroxyphenyl) fluorene, 9,9-bis (di or trihydroxyphenyl) fluorene, 9,9-bis (hydroxynaphthyl) fluorene, 9,9-bis (hydroxyalkoxyphenyl) fluorene, 9,9-bis (alkyl-) It may be at least one selected from hydroxyalkoxyphenyl) fluorene, 9,9-bis (aryl-hydroxyalkoxyphenyl) fluorene, and 9,9-bis (hydroxyalkoxynaphthyl) fluorene.
- the resin may be a thermoplastic resin, and particularly may be at least one selected from a cyclic olefin resin, a methacrylic resin, an aromatic polycarbonate resin, an aromatic polyester resin, and a cellulose derivative.
- the present invention includes a resin composition containing a resin (particularly a cyclic olefin resin) and the wavelength dispersion adjusting agent (fluorene compound).
- the resin composition of the present invention may not contain an epoxy compound.
- the molded object formed with the said resin composition is also contained in this invention.
- Such a molded article may be an optical molded article [such as an optical film (such as a retardation film)].
- the molded body of the present invention may be a film (film-shaped molded body), and such a molded body may be a stretched film.
- the wavelength dispersion adjusting agent fluorene compound
- the resin is added (or mixed) to the resin to impart (or develop) reverse wavelength dispersion to the resin or to reduce the wavelength dispersion of the resin.
- a resin wavelength dispersion adjusting method is also included.
- 9,9-bis (hydroxyaryl) fluorenes and “9,9-bis (hydroxy (poly) alkoxyaryl) fluorenes” mean “9,9-bis (hydroxyaryl)”. As long as it has “) fluorene skeleton” or “9,9-bis (hydroxy (poly) alkoxyaryl) fluorene skeleton”, it includes compounds having substituents on aryl groups and fluorene skeletons (specifically, positions 2 to 7 of fluorene) Use for meaning.
- 9,9-bis (hydroxy (poly) alkoxyaryl) fluorene means 9,9-bis (hydroxyalkoxyaryl) fluorene and 9,9-bis (hydroxypolyalkoxyaryl) fluorene. Used to mean including
- the additive of the present invention can impart (or develop) reverse wavelength dispersion to the resin or reduce the wavelength dispersion of the resin. Since the additive of the present invention does not need to be used as a polymerization component, the wavelength dispersibility can be easily adjusted to the resin. Moreover, the additive of the present invention can be added or mixed with high affinity to a wide range of resins. Furthermore, according to the additive of the present invention, resin properties such as a high refractive index are not impaired or can be maintained. Therefore, the additive of the present invention is very useful or practical.
- the additive of the present invention is an additive for imparting (or expressing) reverse wavelength dispersion (negative wavelength dispersion) to the resin or reducing the wavelength dispersion of the resin (reverse wavelength dispersion imparting agent, reverse Wavelength dispersing agent, wavelength dispersion adjusting agent).
- the additive (wavelength dispersion adjusting agent) is composed of a compound having a 9,9-bisarylfluorene skeleton (hereinafter sometimes referred to as a fluorene compound).
- the fluorene compound only needs to have a 9,9-bisarylfluorene skeleton, such as a compound having no reactive group [for example, 9,9-bisarylfluorene (for example, 9,9-bisphenylfluorene), etc.
- a compound having no reactive group for example, 9,9-bisarylfluorene (for example, 9,9-bisphenylfluorene), etc.
- a compound in which p is 0 in formula (1) described later] may be used, but usually has a reactive group.
- Examples of the reactive group include hydroxyl group, mercapto group, carboxyl group, amino group, (meth) acryloyloxy group, epoxy group (for example, glycidyloxy group) and the like.
- the fluorene compound may have these reactive groups singly or in combination of two or more.
- the reactive group may be directly bonded to 9,9-bisarylfluorene, or may be bonded via an appropriate linking group (for example, a (poly) oxyalkylene group).
- fluorene compound examples include a compound represented by the following formula (1).
- ring Z is an aromatic hydrocarbon ring, R 1 and R 2 are substituents, X is a group — [(OR 3 ) nY] (wherein Y is a hydroxyl group, mercapto group, glycidyl An oxy group or a (meth) acryloyloxy group, R 3 is an alkylene group, n is an integer of 0 or more, or an amino group, k is an integer of 0 to 4, m is an integer of 0 or more, and p is an integer of 1 or more Is shown].
- examples of the aromatic hydrocarbon ring represented by the ring Z include a benzene ring, a condensed polycyclic aromatic hydrocarbon ring [for example, a condensed bicyclic hydrocarbon (for example, indene, naphthalene, etc. Condensed bicyclic to tetracyclic hydrocarbons such as C 8-20 condensed bicyclic hydrocarbons, preferably C 10-16 condensed bicyclic hydrocarbons), condensed tricyclic hydrocarbons (eg anthracene, phenanthrene, etc.), etc.
- a condensed polycyclic aromatic hydrocarbon ring for example, a condensed bicyclic hydrocarbon (for example, indene, naphthalene, etc. Condensed bicyclic to tetracyclic hydrocarbons such as C 8-20 condensed bicyclic hydrocarbons, preferably C 10-16 condensed bicyclic hydrocarbons), condensed tricyclic hydrocarbons (eg anthracene, phen
- a ring assembly hydrocarbon ring (bi or ter C 6-10 arene ring such as biphenyl ring, terphenyl ring or binaphthyl ring).
- the two rings Z may be the same or different rings, and may usually be the same ring.
- Preferred rings Z include a benzene ring, a naphthalene ring, and a biphenyl ring, and may be a benzene ring.
- examples of the group R 1 include a cyano group, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, etc.), a hydrocarbon group [eg, an alkyl group, an aryl group (C 6 such as a phenyl group). -10 aryl group) and the like] and acyl groups (for example, alkylcarbonyl groups such as methylcarbonyl, ethylcarbonyl, pentylcarbonyl, etc.) and the like, and in particular, alkyl groups are often used.
- a cyano group e.g, an alkyl group, an aryl group (C 6 such as a phenyl group). -10 aryl group) and the like
- acyl groups for example, alkylcarbonyl groups such as methylcarbonyl, ethylcarbonyl, pentylcarbonyl, etc.
- alkyl group examples include C 1-12 alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and a t-butyl group (for example, a C 1-8 alkyl group, particularly a C 1-1 such as a methyl group). 4 alkyl group) and the like.
- k is plural (2 to 4)
- the types of the plural groups R 1 may be the same or different from each other.
- the kind of group R ⁇ 1 > substituted by the different benzene ring may be the same or different.
- the bonding position (substitution position) of the group R 1 is not particularly limited, and examples thereof include the 2nd, 7th, 2nd and 7th positions of the fluorene ring.
- the preferred substitution number k is 0 to 1, in particular 0.
- the two substitution numbers k may be the same or different.
- the substituent R 2 substituted on the ring Z is usually a non-reactive substituent, for example, an alkyl group (eg, a C 1-12 alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, C 1-8 alkyl group etc.), cycloalkyl group (C 5-8 cycloalkyl group such as cyclohexyl group), aryl group (eg phenyl group, tolyl group, xylyl group, naphthyl group etc.) Hydrocarbon groups such as 6-10 aryl groups), aralkyl groups (C 6-10 aryl-C 1-4 alkyl groups such as benzyl and phenethyl groups); alkoxy groups (C 1 such as methoxy groups and ethoxy groups) -8 an alkoxy group), such as C 5-10 cycloalkyl group such as a cycloalkoxy group
- a group such as an alkylthio group such as a C 1-8 alkylthio group such as a methylthio group) —SR (wherein R is as defined above); an acyl group (such as a C 1-6 acyl group such as an acetyl group); Alkoxycarbonyl group (C 1-4 alkoxy-carbonyl group such as methoxycarbonyl group); halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom etc.); nitro group; cyano group; substituted amino group (for example, dimethyl group) And a dialkylamino group such as an amino group).
- R is as defined above
- an acyl group such as a C 1-6 acyl group such as an acetyl group
- Alkoxycarbonyl group C 1-4 alkoxy-carbonyl group such as methoxycarbonyl group
- halogen atom fluorine atom, chlorine atom, bromine atom,
- Preferred groups R 2 include hydrocarbon groups [eg, alkyl groups (eg, C 1-6 alkyl groups), cycloalkyl groups (eg, C 5-8 cycloalkyl groups), aryl groups (eg, C 6-10 Aryl group), aralkyl group (for example, C 6-8 aryl-C 1-2 alkyl group and the like), alkoxy group (C 1-4 alkoxy group and the like) and the like.
- Further preferred groups R 2 include an alkyl group [C 1-4 alkyl group (particularly methyl group) and the like], an aryl group [eg C 6-10 aryl group (particularly phenyl group) and the like] and the like.
- the group R 2 may form the ring assembly hydrocarbon ring together with the ring Z.
- the types of the groups R 2 may be the same or different from each other.
- the type of the group R 2 may be the same or different.
- the number of substitutions m can be selected according to the type of the ring Z, and may be, for example, 0 to 8, preferably 0 to 4 (eg, 0 to 3), and more preferably 0 to 2.
- the number of substitutions m may be the same or different from each other, and may usually be the same.
- examples of the alkylene group represented by the group R 3 include C 2-6 alkylene such as ethylene group, propylene group, trimethylene group, 1,2-butanediyl group, and tetramethylene group.
- a group preferably a C 2-4 alkylene group, and more preferably a C 2-3 alkylene group.
- the type of alkylene group may be composed of different alkylene groups, and may be generally composed of the same alkylene group.
- the types of the groups R 3 may be the same or different, and may be usually the same.
- the number (addition mole number) n of oxyalkylene groups (OR 3 ) may be 0 or more (for example, 0 to 20), for example, 0 to 15 (for example, 1 to 12), preferably 0 to 10 ( For example, it may be 1 to 6), more preferably 0 to 4 (eg 1 to 4), particularly 0 to 2 (eg 0 to 1). Further, depending on the type of resin, there may be a case where a remarkable improvement effect is obtained when n is 0 or when n is 1 or more. Therefore, either a compound in which n is 0 or a compound in which n is 1 or more may be selected depending on the type of resin. The number of substitutions n may be the same or different for different rings Z.
- Preferred X is a group — [(OR 3 ) nY], and particularly Y is preferably a hydroxyl group.
- the compound whose Y is a hydroxyl group is represented by following formula (1A).
- the substitution number p of the group X may be 1 or more (for example, 1 to 6), for example, 1 to 4, preferably 1 to 3, more preferably 1 to 2, particularly 1.
- the substitution number p may be the same or different in each ring Z, and is usually the same in many cases.
- the substitution position of the group X is not particularly limited, and it may be substituted at an appropriate substitution position on the ring Z.
- the group X may be substituted at the 2-6 position of the phenyl group, and may preferably be substituted at the 4 position.
- the group X is a hydrocarbon ring different from the hydrocarbon ring bonded to the 9-position of fluorene in the condensed polycyclic hydrocarbon ring (for example, naphthalene
- the ring is substituted at least on the 5th and 6th positions of the ring.
- Specific fluorene compounds include 9,9-bis (hydroxyaryl) fluorenes [or 9,9-bis (hydroxyaryl) fluorene skeletons.
- X is a group in the formula (1), such as - [(OR 3) n- OH] , compound; this In al compounds, hydroxyl group, mercapto group, and the like
- the 9,9-bis (hydroxyphenyl) fluorenes include, for example, 9,9-bis (hydroxyphenyl) fluorene [for example, 9,9-bis (4-hydroxyphenyl) fluorene], 9,9-bis (alkyl 9,9-bis such as 9,9-bis (4-hydroxy-3-methylphenyl) fluorene, 9,9-bis (4-hydroxy-3,5-dimethylphenyl) fluorene (Mono or di C 1-4 alkyl-hydroxyphenyl) fluorene], 9,9-bis (aryl-hydroxyphenyl) fluorene [eg, 9,9-bis (4-hydroxy-3-phenylphenyl) fluorene, etc.
- the 9,9-bis (hydroxynaphthyl) fluorenes correspond to the 9,9-bis (hydroxyphenyl) fluorenes, and are compounds in which the phenyl group is substituted with a naphthyl group, for example, 9,9-bis ( Hydroxynaphthyl) fluorene [eg, 9,9-bis (6-hydroxy-2-naphthyl) fluorene, 9,9-bis (5-hydroxy-1-naphthyl) fluorene] and the like.
- 9,9-bis ( Hydroxynaphthyl) fluorene eg, 9,9-bis (6-hydroxy-2-naphthyl) fluorene, 9,9-bis (5-hydroxy-1-naphthyl) fluorene
- 9,9-bis (hydroxy (poly) alkoxyphenyl) fluorenes include, for example, 9,9-bis (hydroxyalkoxyphenyl) fluorene ⁇ eg, 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, 9,9-bis [4- (2-hydroxypropoxy) phenyl] fluorene such as 9,9-bis (hydroxy C 2-4 alkoxyphenyl) fluorene ⁇ , 9,9-bis (alkyl - hydroxy alkoxyphenyl) Fluorene ⁇ eg, 9,9-bis [4- (2-hydroxyethoxy) -3-methylphenyl] fluorene, 9,9-bis [4- (2-hydroxypropoxy) -3-methylphenyl] fluorene, Such as 9-bis [4- (2-hydroxyethoxy) -3,5-dimethylphenyl] fluorene 9,9-bis (mono or di C 1-4 alkyl-hydroxy C 2-4 alkoxy
- 9,9-bis (hydroxy (poly) alkoxynaphthyl) fluorenes compounds corresponding to the 9,9-bis (hydroxy (poly) alkoxyphenyl) fluorenes, wherein a phenyl group is substituted with a naphthyl group
- 9,9-bis (hydroxyalkoxynaphthyl) fluorene ⁇ eg, 9,9-bis [6- (2-hydroxyethoxy) -2-naphthyl] fluorene, 9,9-bis [6- (2-hydroxypropoxy) 9,9-bis (hydroxyalkoxynaphthyl) fluorenes such as 9,9-bis (hydroxyC 2-4 alkoxynaphthyl) fluorene ⁇ such as) -2-naphthyl] fluorene.
- 9,9-bis (hydroxyphenyl) fluorene 9,9-bis (alkyl-hydroxyphenyl) fluorene [for example, 9,9-bis (mono or di C 1-4 alkyl- Hydroxyphenyl) fluorene], 9,9-bis (aryl-hydroxyphenyl) fluorene [eg, 9,9-bis (mono or diC 6-10 aryl-hydroxyphenyl) fluorene], 9,9-bis (di or A compound in which n is 0 in the above formula (1A) such as trihydroxyphenyl) fluorene and 9,9-bis (hydroxynaphthyl) fluorene; 9,9-bis (hydroxyalkoxyphenyl) fluorene ⁇ eg, 9,9-bis (hydroxy C 2-4 alkoxyphenyl) fluorene ⁇ , 9,9-bis (alkyl - hydroxy alkoxyphenyl) fluorene ⁇ e.g., 9,9-bis (hydroxyphenyl) fluorene
- n is 1 or more (for example, 1 to 4, preferably 1 to 2, more preferably 1) in the above formula (1A) such as -4alkoxynaphthyl) fluorene ⁇ is preferable.
- 9,9-bis (hydroxyalkoxyphenyl) fluorene such as 9,9-bis (hydroxyethoxyphenyl) fluorene may be used from the viewpoint of imparting reverse wavelength dispersion to the resin.
- Fluorene compounds may be used alone or in combination of two or more.
- the additive (fluorene compound) of the present invention is an additive for imparting (or developing) reverse wavelength dispersibility to the resin (or improving the reverse wavelength dispersibility of the resin) (providing reverse wavelength dispersibility).
- the reverse wavelength dispersibility (or the degree thereof) of the resin composition containing the resin and the fluorene compound is the reverse of the resin (the resin to which the fluorene compound is not added or mixed). It becomes higher than the wavelength dispersion (or its degree).
- the wavelength dispersion (or the degree thereof) of the resin composition containing the resin and the fluorene compound is such that the wavelength dispersion of the resin (the resin to which no fluorene compound is added or mixed). Smaller than sex (or its degree).
- the additive of the present invention can often bring the wavelength dispersion of the resin closer to the reverse wavelength dispersion (negative wavelength dispersion) side (the wavelength dispersion of the resin is in the negative direction), It is not always necessary to change the wavelength dispersion of the resin to reverse wavelength dispersion (negative wavelength dispersion) (for example, the wavelength dispersion of a resin having positive wavelength dispersion may be reduced). Moreover, it can also be used for resin which has reverse wavelength dispersion for the purpose of improving reverse wavelength dispersion (negative wavelength dispersion) more.
- the phase difference (or birefringence) at the wavelength ⁇ 0 of the resin A is N 0A
- the phase difference at the wavelength ⁇ 1 (where the wavelength is shorter than ⁇ 0 ) is N 1A
- the wavelength ⁇ 2 (where N 2A the phase difference also in the long-wavelength) from 0
- the phase difference at the wavelength lambda 0 of the resin composition B containing a resin a and fluorene compounds N 0B phase difference N 1B of wavelength lambda 1, position at the wavelength lambda 2
- the phase difference is N 2B
- at least one of the following expressions is often established.
- the wavelength range is not particularly limited, but may be a visible light region of, for example, about 300 to 800 nm (for example, 350 to 770 nm), preferably about 400 to 750 nm (for example, 400 to 700 nm).
- ⁇ 0 , ⁇ 1 , and ⁇ 2 arbitrary values can be selected from the above ranges.
- an arbitrary wavelength in the range of 500 to 650 nm for example, 550 nm, 589 nm, 590 nm, 600 nm, 630 nm, etc. may be selected.
- lambda 1 for example, any one or two or more wavelengths in the range of 300 ⁇ 600 nm (e.g., 350 nm, 400 nm, 450 nm, 500 nm, 550 nm, etc.) may be selected from, lambda 2, for example It may be selected from any one or more wavelengths in the range of 550-800 nm (eg, 630 nm, 650 nm, 700 nm, 750 nm, etc.).
- thermoplastic resin a wide range of resins can be used (or applied), and any of a thermoplastic resin and a curable resin (thermal or photo-curable resin) may be used.
- curable resin thermo or photo-curable resin
- thermoplastic resin examples include olefin resin ⁇ eg, chain olefin resin [ethylene resin (eg, polyethylene), propylene resin (eg, polypropylene), polymethylpentene, etc.], cyclic olefin resin, etc. ⁇ , halogen-containing resin) Vinyl resins (polyvinyl chloride, fluororesins, etc.), vinyl resins (eg, polyvinyl alcohol, acrylonitrile resins), acrylic resins (eg, methacrylic resins such as polymethyl methacrylate), styrene resins [eg, styrene Monomers or copolymers of polystyrene monomers (polystyrene, styrene- ⁇ -methylstyrene copolymer, etc.), copolymers of styrene monomers and copolymerizable monomers (styrene-acrylonitrile copolymers ( AS resin), styrene
- polylactic acid, etc. aromatic polyester resin, etc.] polyacetal resin, polyamide resin (for example, aliphatic polyamide resin such as polyamide 6, polyamide 66, polyamide 610, polyamide 11, polyamide 12, polyamide 612, polyamide 6/66; Aromatic polyamide resins such as polyamide MXD), polyphenylene ether resins, polysulfone resins, polyphenylene sulfide resins, polyimide resins, polyether ketone resins, cellulose derivatives, and thermoplastic elastomers. And so on.
- polyamide resin for example, aliphatic polyamide resin such as polyamide 6, polyamide 66, polyamide 610, polyamide 11, polyamide 12, polyamide 612, polyamide 6/66; Aromatic polyamide resins such as polyamide MXD), polyphenylene ether resins, polysulfone resins, polyphenylene sulfide resins, polyimide resins, polyether ketone resins, cellulose derivatives, and thermoplastic elast
- thermoplastic resins may be used alone or in combination of two or more.
- the molecular weight of the thermoplastic resin can be selected according to the type of the resin.
- the number average molecular weight can be selected from a range of 2000 or more (for example, 3000 or more), 5000 or more (for example, 8000 to 1000000), preferably May be 10,000 or more (for example, 12,000 to 800,000), more preferably 15,000 or more (for example, 20,000 to 500,000).
- the molecular weight can be measured in terms of polystyrene by a conventional method such as gel permeation chromatography (GPC).
- curable resin examples include acrylic resin (heat or photo-curable acrylic resin), phenol resin, amino resin (urea resin, melamine resin, etc.), furan resin, and unsaturated polyester. Resin, epoxy resin, thermosetting urethane resin, silicone resin, thermosetting polyimide resin, diallyl phthalate resin, vinyl ester resin and the like.
- the curable resins may be used alone or in combination of two or more.
- the curable resin may contain a curing agent, a curing accelerator, or the like depending on the type.
- thermoplastic resin thermoplastic resin, curable resin
- thermoplastic resin curable resin
- the resin may be either a crystalline resin or an amorphous resin.
- the resin may be a resin having a positive wavelength dispersion or a resin having a negative wavelength dispersion (reverse wavelength dispersion).
- the additive of the present invention may be suitably used for a thermoplastic resin.
- the additive of the present invention may be suitably used for a resin having excellent transparency, such as a cyclic olefin resin, a methacrylic resin, an aromatic polycarbonate resin, an aromatic polyester resin, and a cellulose derivative.
- a resin having excellent transparency such as a cyclic olefin resin, a methacrylic resin, an aromatic polycarbonate resin, an aromatic polyester resin, and a cellulose derivative.
- Cyclic olefin resin is resin which uses cyclic olefin as a polymerization component at least.
- the cyclic olefin may be a monocyclic olefin or a polycyclic olefin.
- the cyclic olefin includes a substituent such as a hydrocarbon group [eg, an alkyl group (eg, a C 1-10 alkyl group such as a methyl group, preferably a C 1-5 alkyl group), a cycloalkyl group (eg, cyclohexyl group).
- a C 5-10 cycloalkyl group such as a group), an aryl group (eg, a C 6-10 aryl group such as a phenyl group), an alkenyl group (eg, a C 2-10 alkenyl group such as a propenyl group), a cycloalkenyl group (For example, C 5-10 cycloalkenyl group such as cyclopentenyl group, cyclohexenyl group, etc.), alkylidene group (eg, C 2-10 alkylidene group such as ethylidene group, preferably C 2-5 alkylidene group, etc.) , polar group [e.g., alkoxy groups (e.g., C 1-10 alkoxy group such as methoxy group, preferred Ku is C 1-6 alkoxy group), an acyl group (e.g., a C 2-5 alkanoyl group such as acetyl group), an acyloxy group [e.
- cyclic olefins include monocyclic olefins [eg, cycloalkenes (eg, cycloC 3-10 alkenes such as cyclobutene, cyclopentene, cycloheptene, cyclooctene, etc.), cycloalkadienes (eg, cyclopentadiene, etc.
- cycloalkenes eg, cycloC 3-10 alkenes such as cyclobutene, cyclopentene, cycloheptene, cyclooctene, etc.
- cycloalkadienes eg, cyclopentadiene, etc.
- bicyclic olefins ⁇ eg norbornenes [eg norbornene (eg 2-norbornene), alkyl norbornene (eg 5-methyl-2-norbornene, 5, 5 or 5,6-dimethyl-2-norbornene, 5-ethylidene-2-norbornene), aryl norbornene (eg, 5-phenyl-2-norbornene), norbornene having a polar group (eg, 5-cyano-2-norbornene, etc.) Cyanonorbornene Acyloxynorbornene such as 5-methoxycarbonyl-2-norbornene, 5-methyl-5-methoxycarbonyl-2-norbornene, 5,6-dimethoxycarbonyl-2-norbornene, 5-methyl-5-cyclohexyloxycarbonyl-2-norbornene (Alkoxycarbonyl norbornene,
- Acyloxynorbornadiene (such as alkoxycarbonylnorbornadiene); haloalkylnorbornadiene such as 5,6-di (trifluoromethyl) -2,5-norbornadiene; oxonorbornadiene such as 7-oxo-2-norbornadiene)], tricyclic olefin ⁇
- tricycloalkenes eg, C 6-25 tricycloalkenes such as dihydrodicyclopentadienes (such as dihydrodicyclopentadiene)]
- tricycloalkadienes eg, Dicyclopentadiene (dicyclopentadiene, methyldicyclopentadiene, etc.), tricyclo [4.4.0.1 2,5 ] undeca-3,7-diene, tricyclo [4.4.0.1 2,5 ]
- a C 6-25 tricycloalkadiene such as undeca-3,8-diene, etc.]
- cyclic olefins e.g., hexa cycloalkenes (e.g., hexacyclo [6.6.1.1 3,6 .0 2,7 .0 9,14] -4- heptadecene C such as 12-40 Hexacycloalkene) and the like ⁇ and the like.
- the cyclic olefin resin may be a cyclic olefin homopolymer or a copolymer (for example, a copolymer of a monocyclic olefin and a polycyclic olefin, a copolymer of a plurality of polycyclic olefins, etc.), or cyclic.
- a copolymer of an olefin and a copolymerizable monomer may be used.
- Examples of the copolymerizable monomer include a chain olefin [alkene (eg, ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, 2-methyl-1-pentene).
- alkene eg, ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, 2-methyl-1-pentene.
- 3-ethyl-1-pentene 4-methyl-1-pentene, 4-methyl-1-hexene, 4,4-dimethyl-1-hexene, 4,4-dimethyl-1-pentene, 4-ethyl-1 C 2-20 alkenes such as -hexene, 3-ethyl-1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicocene), alkadienes (for example , 1,4-hexadiene, 4-methyl-1,4-hexadiene, 5-methyl-1,4-hexadiene, 1,7-nonconjugated C 5-20 a such octadiene Cadien etc.), polymerizable nitrile compounds (eg (meth) acrylonitrile etc.), (meth) acrylic monomers (eg (meth) acrylic acid such as methyl
- the ratio of cyclic olefin is, for example, 10 mol% or more (for example, 20 mol) with respect to the total amount of cyclic olefin and copolymerizable monomer. % Or more), preferably 30 mol% or more, more preferably 40 mol% or more.
- Preferred cyclic olefin resins include cyclic olefin copolymers ⁇ eg, cyclic olefins (eg, cyclic olefins containing at least norbornenes) and copolymerizable monomers [eg, chain olefins (eg, C 2 ⁇ Copolymer) with a copolymerizable monomer containing at least 6 alkene).
- cyclic olefin copolymers eg, cyclic olefins (eg, cyclic olefins containing at least norbornenes) and copolymerizable monomers [eg, chain olefins (eg, C 2 ⁇ Copolymer) with a copolymerizable monomer containing at least 6 alkene).
- a cyclic olefin copolymer having a polar group for example, a cyclic olefin having a polar group ⁇ eg, norbornene having a polar group [eg, acyloxynorbornene (eg, 5-methoxycarbonyl-2 An alkoxycarbonyl group such as norbornene or 5-methyl-5-methoxycarbonyl-2-norbornene (eg, norbornene substituted with a C 1-10 alkoxycarbonyl group, preferably a C 1-4 alkoxycarbonyl group), etc.]
- a copolymerizable monomer for example, a copolymerizable monomer [for example, a copolymerizable monomer containing at least a chain olefin (eg, C 2-6 alkene such as ethylene)] is preferable. .
- the ratio of the cyclic olefin having a polar group to the whole cyclic olefin is, for example, 10 mol% or more, preferably 20 mol% or more, more preferably 30 mol% or more. May be.
- the cyclic olefin resins may be used alone or in combination of two or more.
- the methacrylic resin examples include resins having at least a methacrylic acid ester as a polymerization component.
- the methacrylic resin is an alkyl methacrylate [for example, an alkyl methacrylate ester (for example, a C 1-20 alkyl methacrylate such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate,
- the alkyl methacrylates may be used alone or in combination of two or more.
- Specific methacrylic resins include alkyl methacrylates (especially alkyl methacrylates containing at least methyl methacrylate) homopolymers or copolymers, alkyl methacrylates (particularly alkyl methacrylates containing at least methyl methacrylate) and copolymers. And a copolymer with a functional monomer.
- the copolymerizable monomer is not particularly limited as long as it is copolymerizable.
- a (meth) acrylic monomer ⁇ for example, (meth) acrylic acid, alkyl acrylate (for example, methyl acrylate, ethyl acrylate) C 1-10 alkyl acrylates such as propyl acrylate and butyl acrylate), alicyclic (meth) acrylates (eg, (meth) acrylic acid C 5-10 cycloalkyl esters such as cyclohexyl (meth) acrylate; Decalinyl (meth) acrylate, norbornyl (meth) acrylate, bornyl (meth) acrylate, bi to tetracycloalkyl (meth) acrylate such as adamantyl (meth) acrylate, etc.], hydroxyalkyl (meth) acrylate [for example, (meth) acrylic Acid hydroxyethyl etc.
- an alkane diol di (meth) acrylate e.g., ethylene glycol di (meth) acrylate, diethylene glycol di ( (Meth) acrylate, tetraethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, etc.
- alkanetriol di to tri (meth) acrylate for example, trimethylolethane tri (meth) acrylate, trimethylolpropane tri ( Meth) acrylates
- polyols such as alkanetetraol di to tetra (meth) acrylates (pentaerythritol tetra (meth) acrylate etc.), poly (meth) acrylates, polyols Alkylene oxide (e.g., C 2-4 alkylene
- Preferred methacrylic resins include resins having methyl methacrylate as a polymerization component, such as polymethyl methacrylate, copolymers having methyl methacrylate as a polymerization component [for example, copolymers of methyl methacrylate and alkyl methacrylate esters. (For example, methyl methacrylate-methacrylic acid C 2-8 alkyl ester copolymer) and the like].
- the proportion of methyl methacrylate is determined based on the total amount of monomers [methyl methacrylate and other monomers (methacrylic acid C 2-8 alkyl ester, copolymerizable monomer). Body etc.)], for example, about 55 to 99.9% by weight, preferably 60% or more (for example, about 65 to 99% by weight), more preferably 70% or more (for example, 75%). Or about 95% by weight).
- Aromaatic polycarbonate resin examples include resins having an aromatic diol and a carbonate-forming compound as polymerization components.
- aromatic diol examples include bisphenols and dihydroxyarene (hydroquinone, resorcinol, etc.).
- bisphenols include dihydroxyarenes [eg, di ( hydroxyC 6-10 arenes) such as 4,4′-dihydroxybiphenyl], bis (hydroxyphenyl) alkanes [eg, bis (4-hydroxyphenyl) methane 1,1-bis (4-hydroxyphenyl) ethane, 1,1-bis (4-hydroxyphenyl) -1-phenylethane, 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis ( 4-hydroxy-3-methylphenyl) propane, 2,2-bis (4-hydroxy-3-isopropylphenyl) propane, 2,2-bis (3-tert-butyl-4-hydroxyphenyl) propane, 2,2 -Bis (4-hydroxyphenyl) butane, 2,2-bis (4-hydroxyphenyl) octane, 2,2 Bis (3-bromo-4-hydroxyphenyl) propane, 2,2-bis
- aromatic diols in particular, bis (hydroxyphenyl) alkanes [especially bis (hydroxyphenyl) C 1-4 alkanes such as 2,2-bis (4-hydroxyphenyl) propane], bis (hydroxyphenyl) Bisphenols such as -alkyl) arenes [bis (hydroxyphenyl-C 1-4 alkyl) benzene etc.] are preferred.
- Aromatic diols may be used alone or in combination of two or more.
- Examples of the carbonate-forming compound include carbonates such as phosgene (phosgene, diphosgene, triphosgene, etc.), carbonates [eg, dialkyl carbonate (dimethyl carbonate, diethyl carbonate, etc.), diaryl carbonate (diphenyl carbonate, dinaphthyl carbonate, etc.). Diesters] and the like. Among these, phosgene, diphenyl carbonate and the like may be preferably used.
- the carbonate-forming compounds may be used alone or in combination of two or more.
- the aromatic polycarbonate resin may be used alone or in combination of two or more.
- aromatic polyester resins include polyalkylene arylate resins, polyarylate resins [for example, aromatic dicarboxylic acids (such as terephthalic acid) and aromatic diols (biphenol, bisphenol A, xylylene glycol, alkylene oxide adducts thereof, etc.) And the like)], and liquid crystalline polyester resins.
- polyalkylene arylate resin examples include polyalkylene terephthalate resin [for example, polyalkylene terephthalate (eg, poly C 2-4 alkylene terephthalate such as polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate), alkylene terephthalate unit (polyalkylene terephthalate unit) ), Polyalkylene naphthalate resin [for example, polyalkylene naphthalate (for example, poly C 2-4 alkylene naphthalate such as polyethylene naphthalate), alkylene naphthalate unit (polyalkylene naphthalate unit) Having a copolyester], polycycloalkane dialkylene terephthalate resin [for example, polycycloalkanedia Sharp emission terephthalate (e.g., poly cyclohexane dimethylene terephthalate), such as a copolyester having cycloalkan
- the copolymer component includes, for example, a diol component [eg, alkane diol (eg, C 2-6 alkane diol such as ethylene glycol, propylene glycol, butane diol, hexane diol), polyalkane diol (eg, diethylene glycol).
- alkane diol eg, C 2-6 alkane diol such as ethylene glycol, propylene glycol, butane diol, hexane diol
- polyalkane diol eg, diethylene glycol
- Di-hexaC 2-4 alkanediols such as polytetramethylene glycol), alicyclic diols (eg 1,4-cyclohexanedimethanol etc.), aromatic diols (eg C 2-4 alkylenes of bisphenols) Oxide adducts, etc.)], dicarboxylic acid components ⁇ eg aliphatic dicarboxylic acids (eg C 4-12 alkane dicarboxylic acids such as glutaric acid, adipic acid, sebacic acid), aromatic dicarboxylic acids [eg asymmetric aromatics] Zika Rubonic acid (eg phthalic acid, isophthalic acid etc.), diphenyldicarboxylic acid etc.] ⁇ , hydroxycarboxylic acid component (eg hydroxybenzoic acid etc.) and the like.
- the copolymerization components may be used alone or in combination of two or more.
- the proportion of alkylene arylate units may be, for example, 40% by weight or more, preferably 50% by weight or more.
- the aromatic polyester resin may be crystalline or non-crystalline.
- the aromatic polyester resin may have a linear structure or a branched structure.
- Aromatic polyester resins may be used alone or in combination of two or more.
- the cellulose derivative is not particularly limited, and various cellulose derivatives such as cellulose ester, cellulose carbamate (for example, cellulose phenyl carbamate), cellulose ether and the like can be used.
- cellulose ester examples include cellulose acetate such as cellulose diacetate (DAC) and cellulose triacetate (TAC); cellulose C 3-5 acylate such as cellulose propionate and cellulose butyrate; cellulose acetate propionate (CAP), And cellulose acylate such as cellulose acetate C 3-5 acylate such as cellulose acetate butyrate (CAB).
- DAC cellulose diacetate
- TAC cellulose triacetate
- cellulose C 3-5 acylate such as cellulose propionate and cellulose butyrate
- CAP cellulose acetate propionate
- CAB cellulose acetate butyrate
- cellulose ether examples include alkyl celluloses (eg, C 1-4 alkyl celluloses such as methyl cellulose and ethyl cellulose), hydroxyalkyl celluloses (eg, hydroxy C 2 ⁇ such as hydroxyethyl cellulose (HEC) and hydroxypropyl cellulose (HPC)).
- alkyl celluloses eg, C 1-4 alkyl celluloses such as methyl cellulose and ethyl cellulose
- hydroxyalkyl celluloses eg, hydroxy C 2 ⁇ such as hydroxyethyl cellulose (HEC) and hydroxypropyl cellulose (HPC)
- hydroxyalkylalkyl cellulose eg, hydroxy C 2-4 alkyl C 1-4 alkyl cellulose such as hydroxypropylmethyl cellulose
- carboxyalkyl cellulose such as carboxymethyl cellulose (CMC)
- alkyl-carboxyalkyl cellulose Such as methyl carboxymethyl cellulose
- carboxymethyl cellulose sodium CMC salts such as alkali metal salts
- cellulose esters and cellulose ethers are preferable, and cellulose esters (cellulose acylates) such as cellulose acetate and cellulose acetate C 3-4 acylate are particularly preferable. More specifically, cellulose esters such as cellulose diacetate, cellulose triacetate, cellulose acetate propionate, and cellulose acetate butyrate may be suitably used as the cellulose derivative.
- the cellulose derivatives may be used alone or in combination of two or more.
- the use ratio of the additive can be selected, for example, from the range of about 0.1 parts by weight or more (for example, 0.2 to 200 parts by weight) with respect to 100 parts by weight of the resin.
- Parts by weight preferably 0.5 to 80 parts by weight, more preferably about 1 to 50 parts by weight, usually 0.5 to 50 parts by weight (for example, 0.5 to 40 parts by weight, preferably 0 7 to 30 parts by weight, more preferably 1 to 20 parts by weight, particularly 2 to 18 parts by weight, particularly preferably 3 to 15 parts by weight).
- the ratio of the additive may be about 5 to 15 parts by weight (particularly 8 to 13 parts by weight) with respect to 100 parts by weight of the resin from the viewpoint of easily imparting reverse wavelength dispersion to the resin.
- the additive (wavelength dispersion adjusting agent) of the present invention depends on the type of resin, a sufficient wavelength dispersion adjusting effect can be obtained even with a small amount.
- the use ratio of the additive (fluorene compound) is reduced. , 10 parts by weight or less (for example, 0.1 to 9 parts by weight), preferably 8 parts by weight or less (for example, 0.2 to 7 parts by weight), more preferably 6 parts by weight or less based on 100 parts by weight of the resin. (For example, 0.3 to 5.5 parts by weight), in particular, 5 parts by weight or less (for example, 0.5 to 3 parts by weight) can also be used.
- the additive of the present invention is excellent in affinity to the resin, and even when added in a relatively large proportion, the resin properties can often be maintained or improved at a high level. Therefore, when the degree of positive wavelength dispersion of the resin is large, the use ratio of the additive is 10 parts by weight or more (for example, 10 to 100 parts by weight), preferably 15 parts by weight with respect to 100 parts by weight of the resin. Part or more (for example, 18 to 80 parts by weight), more preferably 20 parts by weight or more (for example, 25 to 70 parts by weight). Furthermore, the phase difference of the resin can be greatly adjusted by relatively increasing the proportion of the additive.
- the additive (wavelength dispersion adjusting agent) of the present invention a resin (resin composition) having improved (or imparted or expressed) reverse wavelength dispersion or a resin having low wavelength dispersion can be obtained.
- the present invention also includes such a resin composition, that is, a resin composition containing a resin and a wavelength dispersion adjusting agent (fluorene compound).
- the resin composition may contain other additives ⁇ additives that are not fluorene compounds, such as fillers or reinforcing agents, colorants (dye pigments), conductive agents, flame retardants, plasticizers, lubricants, as necessary.
- Stabilizers antioxidants (hindered phenol antioxidants, phosphorus antioxidants, etc.), UV absorbers, heat stabilizers, etc.], mold release agents, antistatic agents, dispersants, flow regulators, leveling agents , An antifoaming agent, a surface modifier, a stress reducing agent, a carbon material, etc. ⁇ .
- additives may be used alone or in combination of two or more.
- the resin composition does not need to contain an epoxy compound.
- the ratio of another additive can be suitably selected according to the kind.
- the proportion of the stabilizer may be about 0.001 to 10 parts by weight, preferably 0.01 to 7 parts by weight, and more preferably about 0.05 to 5 parts by weight with respect to 100 parts by weight of the resin. .
- the resin composition can be obtained by mixing a resin and a fluorene compound (wavelength dispersion adjusting agent) [and other components (other additives, etc. as necessary)].
- the mixing method is not particularly limited, and may be mixed by, for example, melt kneading or may be mixed by dissolving each component in a solvent.
- the present invention also includes a molded body formed of such a resin composition.
- the shape of such a molded body is not particularly limited, and can be appropriately selected depending on the application. For example, a two-dimensional structure (film shape, sheet shape, plate shape, etc.), a three-dimensional structure (tubular, rod shape, tube) Shape, hollow shape, etc.).
- the resin composition of the present invention is often excellent in optical properties, and an optical material or an optical molded body (in particular, an optical film, an optical lens, etc.) may be suitably formed.
- the molded body can be manufactured using, for example, an injection molding method, an injection compression molding method, an extrusion molding method, a transfer molding method, a blow molding method, a pressure molding method, a casting molding method, and the like.
- the resin composition of the present invention is often excellent in various optical properties and is useful for forming a film (particularly an optical film). Therefore, the present invention also includes a film (such as an optical film) formed from the resin composition.
- the thickness of the film can be selected from the range of about 1 to 1000 ⁇ m according to the application, and may be, for example, 1 to 200 ⁇ m, preferably 5 to 150 ⁇ m, and more preferably about 10 to 120 ⁇ m.
- Such a film (such as an optical film) is formed (or molded) from the resin composition using a conventional film formation method, for example, a casting method (solvent casting method), a melt extrusion method, a calendar method, or the like. Can be manufactured.
- a conventional film formation method for example, a casting method (solvent casting method), a melt extrusion method, a calendar method, or the like.
- the film may be a stretched film.
- a stretched film may be either a uniaxially stretched film or a biaxially stretched film.
- the stretching ratio may be about 1.05 to 10 times (for example, 1.1 to 5 times) in each direction in uniaxial stretching or biaxial stretching, and is usually 1.1 to 3 times (for example, 1. 2 to 2.5 times).
- biaxial stretching it may be equal stretching or partial stretching.
- uniaxial stretching longitudinal stretching or lateral stretching may be used.
- the thickness of the stretched film may be, for example, about 1 to 150 ⁇ m, preferably 3 to 120 ⁇ m, and more preferably about 5 to 100 ⁇ m.
- Such a stretched film can be obtained by subjecting a film after film formation (or an unstretched film) to a stretching treatment.
- the stretching method is not particularly limited. In the case of uniaxial stretching, a wet stretching method or a dry stretching method may be used. In the case of biaxial stretching, a tenter method (also referred to as a flat method), a tube method, or the like may be used. Good.
- phase difference The retardation (phase difference) of the film was measured with a high-speed retardation measuring device RE-100 manufactured by Otsuka Electronics Co., Ltd. Moreover, (the retardation value at each wavelength and N 400, N 589, N 700 ) in evaluating the wavelength dispersion, the 400 nm, 589 nm, measurement of retardation values of 700 nm.
- Example 1 100 parts by weight of cellulose triacetate (manufactured by Daicel Corporation, LT55, hereinafter referred to as TAC), 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene (manufactured by Osaka Gas Chemical Co., Ltd., hereinafter referred to as BPEF) ) 11 parts by weight, stabilizer [hindered phenol antioxidant (BASF Japan, IRGANOX1010) and phosphorus antioxidant (Sumitomo Chemical Co., Ltd., SUMILIZER GP)] Using KZW15 / 30 MG) manufactured by Technobel, melt-kneading was performed at a cylinder temperature of 210 to 290 ° C.
- TAC cellulose triacetate
- BPEF 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene
- BPEF 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene
- the ratio of hindered phenolic antioxidant was 2000 ppm with respect to the total amount of TAC and BPEF, and the ratio of phosphorus antioxidant was 1000 ppm with respect to the total amount of TAC and BPEF.
- the resin composition was transparent and was mixed uniformly.
- the obtained resin composition was melt-pressed (hot pressed) using a press molding machine to obtain a film (unstretched film).
- the phase difference (N 400 ) at a wavelength of 400 nm is 0.12 nm
- the phase difference (N 589 ) at a wavelength 589 nm is 0.21 nm
- the phase difference (N 700 ) at a wavelength 700 nm is 0.24 nm
- Example 2 A film (unstretched film) was obtained in the same manner as in Example 1 except that the amount of BPEF used was changed from 11 parts by weight to 18 parts by weight in Example 1.
- the cylinder temperature was 210 to 280 ° C.
- a phase difference at a wavelength of 400 nm (N 400) is 2.36Nm
- the phase difference at a wavelength of 589 nm (N 589) is 3.05Nm
- Example 3 In Example 1, the obtained film was uniaxially stretched from 40 mm to 80 mm at 185 ° C. and 120 mm / min using a film stretching machine (manufactured by Imoto Seisakusho, 11A9 type improved product). A double uniaxially stretched film was obtained.
- the retardation of the obtained film was measured, the retardation at a wavelength of 400 nm (N 400 ) was 336.77 nm, the retardation at a wavelength of 589 nm (N 589 ) was 585.4 nm, and the retardation at a wavelength of 700 nm (N 700 ).
- N 400 the retardation at a wavelength of 400 nm
- N 589 the retardation at a wavelength of 589 nm
- Example 4 In Example 2, the obtained film was uniaxially stretched from 40 mm to 80 mm at 185 ° C. and 120 mm / min using a film stretching machine (manufactured by Imoto Seisakusho, 11A9) and doubled A uniaxially stretched film was obtained.
- the retardation of the obtained film was measured, the retardation at a wavelength of 400 nm (N 400 ) was 76.34 nm, the retardation at a wavelength of 589 nm (N 589 ) was 90.29 nm, and the retardation at a wavelength of 700 nm (N 700 ).
- N 400 the retardation at a wavelength of 400 nm
- N 589 the retardation at a wavelength of 589 nm
- Example 5 In Example 1, instead of using 100 parts by weight of TAC and using 100 parts by weight of a cyclic olefin resin (manufactured by JSR Corporation, ARTONF4520), and not using a hindered phenol antioxidant and a phosphorus antioxidant, A film (unstretched film) was obtained in the same manner as Example 1. The cylinder temperature was 150 to 280 ° C.
- a phase difference at a wavelength of 400 nm (N 400) is 0.34 nm
- the retardation at a wavelength of 589 nm (N 589) is 0.70 nm
- the retardation at a wavelength of 700 nm (N 700 ) was 0.79 nm
- Example 6 Example 5 was the same as Example 2 except that BPEF was replaced with 6,6-bis (9-fluorenylidene) -di (2-naphthol) (Osaka Gas Chemical Co., Ltd., hereinafter referred to as BNF). Thus, a film (unstretched film) was obtained.
- the cylinder temperature was 210 to 280 ° C.
- a phase difference at a wavelength of 400 nm (N 400) is 4.70Nm
- the phase difference at a wavelength of 589 nm (N 589) is 5.08Nm
- the phase difference at a wavelength 700 nm (N 700 ) was 5.18 nm
- Example 7 In Example 5, except that BPEF was replaced with 9,9-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] fluorene (Osaka Gas Chemical Co., Ltd., hereinafter referred to as BOPPEF) In the same manner as in Example 2, a film (unstretched film) was obtained. The cylinder temperature was 210 to 280 ° C.
- a phase difference at a wavelength of 400 nm (N 400) is 4.98Nm
- the phase difference at a wavelength of 589 nm (N 589) is 6.05Nm
- the phase difference at a wavelength 700 nm (N 700 ) was 6.32 nm
- Example 5 (Reference Example 1) In Example 5, a film (unstretched film) was obtained in the same manner as in Example 1 except that BPEF was not used.
- the cylinder temperature was 150 to 280 ° C.
- a phase difference at a wavelength of 400 nm (N 400) is 1.64Nm
- the phase difference at a wavelength of 589 nm (N 589) is 1.24 nm
- the retardation at a wavelength of 700 nm (N 700 ) was 1.14 nm
- the additive of the present invention imparts or develops reverse wavelength dispersibility to the resin (or brings the resin wavelength dispersibility close to negative wavelength dispersibility) or as an additive for reducing the wavelength dispersibility of the resin. Can be used. Moreover, such an additive can also obtain an effect derived from a fluorene compound, and is very useful.
- a resin or a resin composition containing a resin and an additive (fluorene compound) modified by the additive of the present invention (for example, wavelength dispersion is adjusted or reduced in a negative direction) is combined.
- a resin or a resin composition containing a resin and an additive (fluorene compound) modified by the additive of the present invention (for example, wavelength dispersion is adjusted or reduced in a negative direction) is combined.
- the type of resin it has excellent characteristics such as high refractive index, high heat resistance, high transparency, and excellent moldability (such as high melt fluidity).
- Such a resin composition is particularly useful for constructing (or forming) a molded product for optical use (optical molded product) because it is often excellent in optical properties.
- Examples of the optical molded body formed (configured) with such a resin composition include optical films and optical lenses.
- an optical film in addition to a phase film (or a retardation plate), a polarizing film (and a polarizing element and a polarizing plate protective film constituting the polarizing film), an alignment film (alignment film), a viewing angle expansion (compensation) film, a diffusion plate (Film), prism sheet, light guide plate, brightness enhancement film, near infrared absorption film, reflection film, antireflection (AR) film, reflection reduction (LR) film, antiglare (AG) film, transparent conductive (ITO) film, Anisotropic conductive film (ACF), electromagnetic wave shielding (EMI) film, electrode substrate film, color filter substrate film, barrier film, color filter layer, black matrix layer, adhesive layer or release layer between optical films, etc.
- a phase film or a retardation plate
- a polarizing film and a polarizing element and a polarizing plate protective film constituting the polarizing film
- an alignment film alignment film
- a viewing angle expansion (compensation) film a
- the film of the present invention is useful as an optical film for use in an apparatus display.
- the display member (or display) including the optical film of the present invention include FPD devices such as personal computer monitors, televisions, mobile phones, car navigation systems, and touch panels (for example, , LCD, PDP, etc.).
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Abstract
Description
フルオレン化合物は、9,9-ビスアリールフルオレン骨格を有していればよく、反応性基を有しない化合物[例えば、9,9-ビスアリールフルオレン(例えば、9,9-ビスフェニルフルオレン)などの後述の式(1)においてpが0である化合物など]であってもよいが、通常、反応性基を有している。 [Fluorene compound]
The fluorene compound only needs to have a 9,9-bisarylfluorene skeleton, such as a compound having no reactive group [for example, 9,9-bisarylfluorene (for example, 9,9-bisphenylfluorene), etc. A compound in which p is 0 in formula (1) described later] may be used, but usually has a reactive group.
本発明の添加剤(フルオレン化合物)は、前記の通り、樹脂に逆波長分散性を付与(又は発現)させる(又は樹脂の逆波長分散性を向上させる)ための添加剤(逆波長分散性付与剤、逆波長分散性向上剤)又は樹脂の波長分散性を低減するための添加剤(波長分散調整剤)として使用できる。 [Additives and resin composition]
As described above, the additive (fluorene compound) of the present invention is an additive for imparting (or developing) reverse wavelength dispersibility to the resin (or improving the reverse wavelength dispersibility of the resin) (providing reverse wavelength dispersibility). Agent, reverse wavelength dispersion improver) or an additive (wavelength dispersion adjusting agent) for reducing the wavelength dispersion of the resin.
N2A/N0A<N2B/N0B
なお、波長の範囲は、特に限定されないが、例えば、300~800nm(例えば、350~770nm)、好ましくは400~750nm(例えば、400~700nm)程度の可視光域であってもよい。 N 1A / N 0A > N 1B / N 0B
N 2A / N 0A <N 2B / N 0B
The wavelength range is not particularly limited, but may be a visible light region of, for example, about 300 to 800 nm (for example, 350 to 770 nm), preferably about 400 to 750 nm (for example, 400 to 700 nm).
環状オレフィン系樹脂は、環状オレフィンを少なくとも重合成分とする樹脂である。 (Cyclic olefin resin)
Cyclic olefin resin is resin which uses cyclic olefin as a polymerization component at least.
メタクリル樹脂(メタクリル系樹脂、メタクリレート樹脂)としては、少なくともメタクリル酸エステルを重合成分とする樹脂などが挙げられる。通常、メタクリル樹脂は、メタクリル酸アルキル[例えば、メタクリル酸アルキルエステル(例えば、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸プロピル、メタクリル酸ブチル、メタクリル酸2-エチルヘキシルなどのメタクリル酸C1-20アルキル、好ましくはメタクリル酸C1-12アルキル、さらに好ましくはメタクリル酸C1-6アルキル、特にメタクリル酸C1-4アルキル)など]を重合成分とする樹脂であってもよい。メタクリル酸アルキルは、単独で又は2種以上組みあわせてもよい。 (Methacrylic resin)
Examples of the methacrylic resin (methacrylic resin or methacrylate resin) include resins having at least a methacrylic acid ester as a polymerization component. Usually, the methacrylic resin is an alkyl methacrylate [for example, an alkyl methacrylate ester (for example, a C 1-20 alkyl methacrylate such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, Preferably, a resin having a polymerization component of C 1-12 alkyl methacrylate, more preferably C 1-6 alkyl methacrylate, particularly C 1-4 alkyl methacrylate) and the like. The alkyl methacrylates may be used alone or in combination of two or more.
芳香族ポリカーボネート樹脂としては、芳香族ジオールとカーボネート形成性化合物とを重合成分とする樹脂が挙げられる。 (Aromatic polycarbonate resin)
Examples of the aromatic polycarbonate resin include resins having an aromatic diol and a carbonate-forming compound as polymerization components.
芳香族ポリエステル樹脂としては、例えば、ポリアルキレンアリレート樹脂、ポリアリレート樹脂[例えば、芳香族ジカルボン酸(テレフタル酸など)と芳香族ジオール(ビフェノール、ビスフェノールA、キシリレングリコール、これらのアルキレンオキサイド付加体など)を重合成分として用いたポリアリレート樹脂など)など]、液晶性ポリエステル樹脂などが挙げられる。 (Aromatic polyester resin)
Examples of aromatic polyester resins include polyalkylene arylate resins, polyarylate resins [for example, aromatic dicarboxylic acids (such as terephthalic acid) and aromatic diols (biphenol, bisphenol A, xylylene glycol, alkylene oxide adducts thereof, etc.) And the like)], and liquid crystalline polyester resins.
セルロース誘導体としては、特に制限されず、種々のセルロース誘導体、例えば、セルロースエステル、セルロースカーバメート(例えば、セルロースフェニルカーバメートなど)、セルロースエーテルなどが使用できる。 (Cellulose derivative)
The cellulose derivative is not particularly limited, and various cellulose derivatives such as cellulose ester, cellulose carbamate (for example, cellulose phenyl carbamate), cellulose ether and the like can be used.
フィルムのレタデーション(位相差)については、大塚電子(株)製、高速レタデーション測定装置RE-100にて測定を行った。また、波長分散性を評価する上で、400nm、589nm、700nmのレタデーション値を測定した(各波長でのレタデーション値をN400、N589、N700とする)。 (Phase difference, wavelength dispersion)
The retardation (phase difference) of the film was measured with a high-speed retardation measuring device RE-100 manufactured by Otsuka Electronics Co., Ltd. Moreover, (the retardation value at each wavelength and N 400, N 589, N 700 ) in evaluating the wavelength dispersion, the 400 nm, 589 nm, measurement of retardation values of 700 nm.
セルローストリアセテート((株)ダイセル製、LT55、以下、TACという)100重量部、9,9-ビス[4-(2-ヒドロキシエトキシ)フェニル]フルオレン(大阪ガスケミカル(株)製、以下、BPEFという)11重量部、安定剤[ヒンダードフェノール系酸化防止剤(BASFジャパン(株)製、IRGANOX1010)およびリン系酸化防止剤(住友化学(株)製、SUMILIZER GP)]を、二軸押出機(テクノベル社製 KZW15/30 MG)を用いて210~290℃のシリンダー温度にて溶融混練し、ペレット状の樹脂組成物を得た。なお、ヒンダードフェノール系酸化防止剤の割合は、TACとBPEFの総量に対して2000ppm、リン系酸化防止剤の割合はTACとBPEFの総量に対して1000ppmとした。なお、樹脂組成物は、透明であり、均一に混合されていた。 (Example 1)
100 parts by weight of cellulose triacetate (manufactured by Daicel Corporation, LT55, hereinafter referred to as TAC), 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene (manufactured by Osaka Gas Chemical Co., Ltd., hereinafter referred to as BPEF) ) 11 parts by weight, stabilizer [hindered phenol antioxidant (BASF Japan, IRGANOX1010) and phosphorus antioxidant (Sumitomo Chemical Co., Ltd., SUMILIZER GP)] Using KZW15 / 30 MG) manufactured by Technobel, melt-kneading was performed at a cylinder temperature of 210 to 290 ° C. to obtain a pellet-shaped resin composition. In addition, the ratio of hindered phenolic antioxidant was 2000 ppm with respect to the total amount of TAC and BPEF, and the ratio of phosphorus antioxidant was 1000 ppm with respect to the total amount of TAC and BPEF. In addition, the resin composition was transparent and was mixed uniformly.
実施例1において、BPEFの使用量を11重量部から18重量部に代えた以外は、実施例1と同様にして、フィルム(未延伸フィルム)を得た。なお、シリンダー温度は210~280℃とした。 (Example 2)
A film (unstretched film) was obtained in the same manner as in Example 1 except that the amount of BPEF used was changed from 11 parts by weight to 18 parts by weight in Example 1. The cylinder temperature was 210 to 280 ° C.
実施例1において、得られたフィルムを、フィルム延伸機((株)井元製作所製、11A9型改良品)を用いて、185℃、120mm/分で40mmから80mmまで1軸延伸を実施し、2倍1軸延伸フィルムを得た。得られたフィルムについて、位相差を測定したところ、波長400nmにおける位相差(N400)は336.77nm、波長589nmにおける位相差(N589)は585.4nm、波長700nmにおける位相差(N700)は647.54nmであり、逆波長分散性を示した(N400/N589=0.58、N700/N589=1.11)。 (Example 3)
In Example 1, the obtained film was uniaxially stretched from 40 mm to 80 mm at 185 ° C. and 120 mm / min using a film stretching machine (manufactured by Imoto Seisakusho, 11A9 type improved product). A double uniaxially stretched film was obtained. When the retardation of the obtained film was measured, the retardation at a wavelength of 400 nm (N 400 ) was 336.77 nm, the retardation at a wavelength of 589 nm (N 589 ) was 585.4 nm, and the retardation at a wavelength of 700 nm (N 700 ). Was 647.54 nm and exhibited inverse wavelength dispersion (N 400 / N 589 = 0.58, N 700 / N 589 = 1.11).
実施例2において、得られたフィルムを、フィルム延伸機((株)井元製作所製、11A9型改)を用いて、185℃、120mm/分で40mmから80mmまで1軸延伸を実施し、2倍1軸延伸フィルムを得た。得られたフィルムについて、位相差を測定したところ、波長400nmにおける位相差(N400)は76.34nm、波長589nmにおける位相差(N589)は90.29nm、波長700nmにおける位相差(N700)は93.78nmであり、逆波長分散性を示した(N400/N589=0.85、N700/N589=1.04)。 Example 4
In Example 2, the obtained film was uniaxially stretched from 40 mm to 80 mm at 185 ° C. and 120 mm / min using a film stretching machine (manufactured by Imoto Seisakusho, 11A9) and doubled A uniaxially stretched film was obtained. When the retardation of the obtained film was measured, the retardation at a wavelength of 400 nm (N 400 ) was 76.34 nm, the retardation at a wavelength of 589 nm (N 589 ) was 90.29 nm, and the retardation at a wavelength of 700 nm (N 700 ). Was 93.78 nm and exhibited reverse wavelength dispersion (N 400 / N 589 = 0.85, N 700 / N 589 = 1.04).
実施例1において、TAC100重量部に代えて環状オレフィン樹脂(JSR(株)製、ARTONF4520)100重量部を用い、ヒンダードフェノール系酸化防止剤およびリン系酸化防止剤を用いなかったこと以外は、実施例1と同様にして、フィルム(未延伸フィルム)を得た。なお、シリンダー温度は150~280℃とした。 (Example 5)
In Example 1, instead of using 100 parts by weight of TAC and using 100 parts by weight of a cyclic olefin resin (manufactured by JSR Corporation, ARTONF4520), and not using a hindered phenol antioxidant and a phosphorus antioxidant, A film (unstretched film) was obtained in the same manner as Example 1. The cylinder temperature was 150 to 280 ° C.
実施例5において、BPEFを6,6-ビス(9-フルオレニリデン)―ジ(2-ナフトール)(大阪ガスケミカル(株)製、以下、BNFという)に代えた以外は、実施例2と同様にして、フィルム(未延伸フィルム)を得た。なお、シリンダー温度は210~280℃とした。 (Example 6)
Example 5 was the same as Example 2 except that BPEF was replaced with 6,6-bis (9-fluorenylidene) -di (2-naphthol) (Osaka Gas Chemical Co., Ltd., hereinafter referred to as BNF). Thus, a film (unstretched film) was obtained. The cylinder temperature was 210 to 280 ° C.
実施例5において、BPEFを9,9-ビス[4-(2-ヒドロキシエトキシ)-3-フェニルフェニル]フルオレン(大阪ガスケミカル(株)製、以下、BOPPEFという)に代えた以外は、実施例2と同様にして、フィルム(未延伸フィルム)を得た。なお、シリンダー温度は210~280℃とした。 (Example 7)
In Example 5, except that BPEF was replaced with 9,9-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] fluorene (Osaka Gas Chemical Co., Ltd., hereinafter referred to as BOPPEF) In the same manner as in Example 2, a film (unstretched film) was obtained. The cylinder temperature was 210 to 280 ° C.
実施例5において、BPEFを利用しなかった以外は、実施例1と同様にして、フィルム(未延伸フィルム)を得た。なお、シリンダー温度は150~280℃とした。 (Reference Example 1)
In Example 5, a film (unstretched film) was obtained in the same manner as in Example 1 except that BPEF was not used. The cylinder temperature was 150 to 280 ° C.
Claims (9)
- 樹脂に逆波長分散性を付与するか又は樹脂の波長分散性を低減するための添加剤であって、9,9-ビスアリールフルオレン骨格を有する化合物で構成された波長分散調整剤。 A wavelength dispersion adjusting agent composed of a compound having a 9,9-bisarylfluorene skeleton, which is an additive for imparting reverse wavelength dispersion to a resin or reducing the wavelength dispersion of a resin.
- 9,9-ビスアリールフルオレン骨格を有する化合物が、下記式(1)で表される化合物である請求項1記載の波長分散調整剤。
- 9,9-ビスアリールフルオレン骨格を有する化合物が、下記式(1A)で表される化合物である請求項1又は2記載の波長分散調整剤。
- 環Zがベンゼン環又はナフタレン環、R1がアルキル基、kが0~1、R2がアルキル基、シクロアルキル基、アリール基、アラルキル基又はアルコキシ基、mが0~2、R3がC2-4アルキレン基、nが0~2、pが1~3である請求項2又は3記載の波長分散調整剤。 Ring Z is a benzene ring or naphthalene ring, R 1 is an alkyl group, k is 0 to 1, R 2 is an alkyl group, cycloalkyl group, aryl group, aralkyl group or alkoxy group, m is 0 to 2, and R 3 is C The wavelength dispersion adjusting agent according to claim 2 or 3, wherein 2-4 alkylene group, n is 0 to 2, and p is 1 to 3.
- 9,9-ビスアリールフルオレン骨格を有する化合物が、9,9-ビス(ヒドロキシフェニル)フルオレン、9,9-ビス(アルキル-ヒドロキシフェニル)フルオレン、9,9-ビス(アリール-ヒドロキシフェニル)フルオレン、9,9-ビス(ジ又はトリヒドロキシフェニル)フルオレン、9,9-ビス(ヒドロキシナフチル)フルオレン、9,9-ビス(ヒドロキシアルコキシフェニル)フルオレン、9,9-ビス(アルキル-ヒドロキシアルコキシフェニル)フルオレン、9,9-ビス(アリール-ヒドロキシアルコキシフェニル)フルオレン、9,9-ビス(ヒドロキシアルコキシナフチル)フルオレンから選択された少なくとも1種である請求項1~4のいずれかに記載の波長分散調整剤。 Compounds having a 9,9-bisarylfluorene skeleton include 9,9-bis (hydroxyphenyl) fluorene, 9,9-bis (alkyl-hydroxyphenyl) fluorene, 9,9-bis (aryl-hydroxyphenyl) fluorene, 9,9-bis (di or trihydroxyphenyl) fluorene, 9,9-bis (hydroxynaphthyl) fluorene, 9,9-bis (hydroxyalkoxyphenyl) fluorene, 9,9-bis (alkyl-hydroxyalkoxyphenyl) fluorene The wavelength dispersion adjusting agent according to any one of claims 1 to 4, which is at least one selected from 1,9,9-bis (aryl-hydroxyalkoxyphenyl) fluorene and 9,9-bis (hydroxyalkoxynaphthyl) fluorene. .
- 樹脂が、熱可塑性樹脂である請求項1~5のいずれかに記載の波長分散調整剤。 6. The wavelength dispersion adjusting agent according to claim 1, wherein the resin is a thermoplastic resin.
- 樹脂が、環状オレフィン樹脂、メタクリル樹脂、芳香族ポリカーボネート樹脂、芳香族ポリエステル樹脂およびセルロース誘導体から選択された少なくとも1種である請求項1~6のいずれかに記載の波長分散調整剤。 The wavelength dispersion adjusting agent according to any one of claims 1 to 6, wherein the resin is at least one selected from a cyclic olefin resin, a methacrylic resin, an aromatic polycarbonate resin, an aromatic polyester resin, and a cellulose derivative.
- 環状オレフィン樹脂および請求項1~7のいずれかに記載の波長分散調整剤を含む樹脂組成物。 A resin composition comprising a cyclic olefin resin and a wavelength dispersion adjusting agent according to any one of claims 1 to 7.
- 請求項1~7のいずれかに記載の波長分散調整剤を樹脂に添加し、樹脂に逆波長分散性を付与するか又は樹脂の波長分散性を低減する樹脂の波長分散調整方法。 A method for adjusting the wavelength dispersion of a resin, wherein the wavelength dispersion adjusting agent according to any one of claims 1 to 7 is added to the resin to impart reverse wavelength dispersion to the resin or to reduce the wavelength dispersion of the resin.
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CN201480018529.4A CN105377970A (en) | 2013-04-10 | 2014-04-07 | Wavelength dispersion adjustment agent, resin composition, and method for adjusting wavelength dispersion of resin |
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JP7099440B2 (en) | 2017-03-15 | 2022-07-12 | コニカミノルタ株式会社 | A polarizing plate and a display device equipped with the polarizing plate. |
JP2018024630A (en) * | 2017-05-11 | 2018-02-15 | 大神薬化株式会社 | 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystal |
JP2018197848A (en) * | 2017-05-24 | 2018-12-13 | 大阪ガスケミカル株式会社 | Polarizing plate protective film, manufacturing method therefor, and polarizing plate |
Also Published As
Publication number | Publication date |
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CN105377970A (en) | 2016-03-02 |
JPWO2014168107A1 (en) | 2017-02-16 |
KR20150142681A (en) | 2015-12-22 |
TW201500428A (en) | 2015-01-01 |
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