TECHNICAL FIELD
[0001]
The present invention relates to a compound, a resin
obtained from the compound or a polycarbonate resin, and an
optical molded article containing the resin or the polycarbonate
10 resin.
BACKGROUND ART
[0002]
Optical glass or an optical resin is used as a material for
15 an optical lens used in an optical system of various kinds of
cameras such as a camera, a film-integrated camera, and a video
camera. The optical glass is excellent in heat resistance,
transparency, dimensional stability, chemical resistance, and
the like, and there are various kinds of materials having
20 various refractive indices and Abbe numbers. However, there are
problems that the material cost is high, the molding
processability is poor, and the productivity is low.
[0003]
On the other hand, an optical lens formed of an optical
25 resin has an advantage that mass production can be achieved by
injection molding. For example, a polycarbonate resin or the
like is used in camera lenses. However, in recent years, there
2
has been a demand for the development of resins having a high
refractive index due to lightness, thinness, shortness, and
miniaturization of products. In general, since in a case where
the refractive index of an optical material is high, lens
elements having the same refractive index can 5 be realized with a
surface having a smaller curvature, the aberration amount
generated on this surface can be reduced. As a result, it is
possible to reduce the number of lenses, reduce the eccentricity
sensitivity of a lens, and reduce the thickness and weight of a
10 lens.
[0004]
Examples of techniques related to the optical resin include
those described in Patent Documents 1 and 2.
[0005]
15 In Patent Document 1 (Japanese Unexamined Patent
Publication No. 2005-241962), an optical lens that is formed of
a polycarbonate resin having a fluorene structure is described.
[0006]
In Patent Document 2 (Japanese Unexamined Patent
20 Publication No. 2005-187661), a method for easily improving a
refractive index by blending (mixing and adding) a sulfurcontaining
compound with a fluorene-containing polyester is
described.
25 RELATED DOCUMENT
PATENT DOCUMENTS
[0007]
3
[Patent Document 1] Japanese Unexamined Patent Publication
No. 2005-241962
[Patent Document 2] Japanese Unexamined Patent Publication
No. 2005-187661
5
SUMMARY OF THE INVENTION
TECHNICAL PROBLEM
[0008]
However, the polycarbonate resin as described in Patent
10 Document 1 has a low refractive index and is not a sufficiently
satisfactory resin.
In addition, as described in Patent Document 2, in a case
where the sulfur-containing compound is blended with the
fluorene-containing polyester, the refractive index is improved.
15 However, in a case where the heat stability is lowered due to
the addition of a low molecular weight component, and the
compatibility of the two components to be blended is poor, the
transparency may decrease.
[0009]
20 The present invention has been made in view of the above
circumstances, and an object of the present invention is to
provide a resin and a polycarbonate resin capable of realizing
an optical molded article having a high refractive index and
excellent transparency.
25 SOLUTION TO PROBLEM
[0010]
The present inventors have diligently studied to provide a
4
polycarbonate resin capable of realizing an optical molded
article having a high refractive index and excellent
transparency. As a result, the present inventors have found
that an optical molded article having a high refractive index
and excellent transparency can be realized by 5 a resin obtained
by polymerization of a compound represented by the following
Formula (1), and have reached the present invention.
[0011]
According to the present invention, a compound represented
10 by the following General Formula (1), a resin obtained from the
compound, a polycarbonate resin derived from the compound, and
an optical molded article are provided.
[0012]
[1] A compound represented by General Formula (1),
15
in which in General Formula (1), Ar1 and Ar2 independently
represent a group selected from the following Formulae,
5
where, R1 to R6 each represent a hydrogen atom, a
hydrocarbon group, or a heteroatom-containing hydrocarbon group,
A1 to A5 and B1 to B5 each represent a hydrogen atom, a
hydrocarbon group, or a heteroatom-containing 5 hydrocarbon group,
at least one of A1 to A5 is a -Y1-Ar3 group,
at least one of B1 to B5 is a -Y2-Ar4 group,
Y1 and Y2 each represent a single bond or a linking group,
Ar3 and Ar4 each represent an aromatic group,
10 X1 to X4 each are -O-, -S-, -NR'-, or -C(Me)2-,
Z1 to Z4 each represent a hydrocarbon atom, a hydrocarbon
group, or a heteroatom-containing hydrocarbon group,
6
R' represents a hydrogen atom, a hydrocarbon group, or a
heteroatom-containing hydrocarbon group, and
o and p each represent an integer of 1 to 4.
[2] The compound according to [1], in which in General
Formula (1), o 5 and p each are 2.
[3] The compound according to [1] or [2], in which in
General Formula (1), Ar1 and Ar2 independently represent a group
selected from the following formulae,
10 R1 to R6 each represent a hydrogen atom, a hydrocarbon
group, or a heteroatom-containing hydrocarbon group, and
o and p each represent an integer of 1 to 4.
[4] A resin obtained by polymerization of the compound
represented by General Formula (1) according to any one of [1]
15 to [3].
[5] A polycarbonate resin derived from the compound
represented by General Formula (1) according to any one of [1]
to [3].
[6] An optical molded article containing the resin
20 according to [4] or [5].
[7] The optical molded article according to [6], in which
the optical molded article is an optical lens.
[8] The optical molded article according to [6], in which
the optical molded article is an optical film.
7
ADVANTAGEOUS EFFECTS OF INVENTION
[0013]
According to the present invention, it is possible to
provide the resin and the polycarbonate 5 resin capable of
realizing the optical molded article having the high refractive
index and excellent transparency.
DESCRIPTION OF EMBODIMENTS
10 [0014]
Hereinafter, embodiments of the present invention will be
described. Unless otherwise specified, the term "to" between
the numerical values in the text indicates a range of equal to
or more than a numerical value and equal to or less than a
15 numerical value.
[0015]
[Compound]
A compound according to the present embodiment will be
described. The compound according to the present embodiment is
20 a compound represented by General Formula (1).
In General Formula (1), Ar1 and Ar2 independently represent
a group selected from the following formulae,
8
[0016]
where, R1 to R6 each represent a hydrogen atom, a
hydrocarbon group, or a heteroatom-containing hydrocarbon group,
A1 to A5 and B1 to B5 each represent 5 a hydrogen atom, a
hydrocarbon group, or a heteroatom-containing hydrocarbon group,
at least one of A1 to A5 is a -Y1-Ar3 group,
at least one of B1 to B5 is a -Y2-Ar4 group,
Y1 and Y2 each represent a single bond or a linking group,
10 Ar3 and Ar4 each represent an aromatic group, X1 to X4 each are -
O-, -S-, -NR'-, or -C(Me)2-,
Z1 to Z4 each represent a hydrogen atom, a hydrocarbon
9
group, or a heteroatom-containing hydrocarbon group,
R' represents a hydrogen atom, a hydrocarbon group, or a
heteroatom-containing hydrocarbon group, and
o and p each represent an integer of 1 to 4.
5 [0017]
In General Formula (1), R1 to R6 each are preferably
independently selected from a hydrogen atom and an alkyl group
having 1 to 3 carbon atoms or an aryl group having 6 to 20
carbon atoms, R1 to R6 each are more preferably independently
10 selected from a hydrogen atom, a methyl group, a phenyl group, a
biphenyl group, a naphthyl group, and R1 to R6 each are even more
preferably a hydrogen atom.
[0018]
In General Formula (1), o and p each are an integer of 1 to
15 4, preferably an integer of 1 or 2, and more preferably an
integer of 2. By setting o and p to the above range, a
polycarbonate resin obtained from the compound of General
Formula (1) has excellent heat resistance.
[0019]
20 In one embodiment, Ar1 and Ar2 in General Formula (1)
independently represent a group selected from the following
formulae,
R1 to R6 each represent a hydrogen atom, a hydrocarbon
10
group, or a heteroatom-containing hydrocarbon group, and
o and p each represent an integer of 1 to 4.
[0020]
Examples of preferred aspects of Ar1 and Ar2 in General
Formula (1) each include the following 5 formulae.
[0021]
[0022]
11
[0023]
5 [0024]
Examples of the compound represented by General Formula (1)
12
include 9,9-bis(1'-hydroxymethyl)-2,7-dinaphthalen-2"-yl-9Hfluorene,
9,9-bis(1'-hydroxymethyl)-2,7-dinaphthalen-1"-yl-9Hfluorene,
9,9-bis(1'-hydroxymethyl)-3,6-dinaphthalen-2"-yl-9Hfluorene,
9,9-bis(1'-hydroxymethyl)-3,6-dinaphthalen-1"-yl-9Hfluorene,
9,9-bis(1'-hydroxymethyl)-5 2,7-di-p-biphenyl-9Hfluorene,
9,9-bis(1'-hydroxymethyl)-2,7-di-m-biphenyl-9Hfluorene,
9,9-bis(1'-hydroxymethyl)-2,7-bis(3",5"-
diphenylphenyl)-9H-fluorene, 9,9-bis(1'-hydroxymethyl)-2,7-
bis[dibenzo[b,d]furan-4"-yl]-9H-fluorene, 9,9-bis(1'-
10 hydroxymethyl)-2,7-bis[dibenzo[b,d]thiophen-4"-yl]-9H-fluorene,
9,9-bis(1'-hydroxymethyl)-2,7-bis(4"-phenoxyphenyl)-9H-fluorene,
9,9-bis(1'-hydroxymethyl)-2,7-bis(4"-phenylnaphthalen-1"-yl)-9Hfluorene,
9,9-bis(1'-hydroxymethyl)-2,7-bis[4-(naphthalen-2-
yl)phenyl]-9H-fluorene, 9,9-bis(1'-hydroxymethyl)-2,7-bis[3-
15 (naphthalen-2-yl)phenyl]-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-
2,7-dinaphthalen-2"-yl-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-
2,7-dinaphthalen-1"-yl-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-
3,6-dinaphthalen-2"-yl-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-
3,6-dinaphthalen-1"-yl-9H-naphthalene, 9,9-bis(2'-hydroxyethyl)-
20 2,7-di-p-biphenyl-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-2,7-dim-
biphenyl-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-2,7-di-obiphenyl-
9H-fluorene, 9,9-bis(2'-hydroxyethyl)-2,7-bis(3",5"-
diphenylphenyl)-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-2,7-
bis[dibenzo[b,d]]furan-4"-yl]-9H-fluorene, 9,9-bis(2'-
25 hydroxyethyl)-2,7-bis[dibenzo[b,d]thiophen-4"-yl]-9H-fluorene,
9,9-bis(2'-hydroxyethyl)-2,7-bis(4"-phenoxyphenyl)-9H-fluorene,
9,9-bis(2'-hydroxyethyl)-2,7-bis(3",5"-diphenoxyphenyl)-9H13
fluorene, 9,9-bis(2'-hydroxyethyl)-2,7-bis(4"-phenylnaphthalen-
1"-yl)-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-2,7-bis[4-
(naphthalen-2-yl)phenyl]-9H-fluorene, 9,9-bis(2'-hydroxyethyl)-
2,7-bis[3-(naphthalen-2-yl)phenyl]-9H-fluorene, 9,9-bis(2'-
hydroxyethyl)-2,7-bis[3-(naphthalen-1-yl)5 phenyl]-9H-fluorene,
9,9-bis(2'-hydroxyethyl)-2,7-bis[4-(naphthalen-1-yl)phenyl]-9Hfluorene,
9,9-bis(2'-hydroxyethyl)-2,7-diphenanthryl-9"-yl-9Hfluorene,
9,9-bis(2'-hydroxyethyl)-2,7-bis[9",9"-dimethyl-9"-
fluoren-2"-yl]-9H-fluorene, 9,9-bis(3'-hydroxypropyl)-2,7-
10 dinaphthalen-2"-yl-9H-fluorene, 9,9-bis(3'-hydroxypropyl)-2,7-
dinaphthalen-1"-yl-9H-fluorene, 9,9-bis(3'-hydroxypropyl)-3,6-
dinaphthalen-2"-yl-9H-fluorene, 9,9-bis(3'-hydroxypropyl)-3,6-
dinaphthalen-1"-yl-9H-naphthalene, 9,9-bis(4'-hydroxybutyl)-2,7-
dinaphthalen-2"-yl-9H-fluorene, 9,9-bis(4'-hydroxybutyl)-2,7-
15 dinaphthalen-1"-yl-9H-fluorene, 9,9-bis(4'-hydroxybutyl)-3,6-
dinaphthalen-2"-yl-9H-fluorene, 9,9-bis(4'-hydroxybutyl)-3,6-
dinaphthalen-1"-yl-9H-naphthalene, 9,9-bis(4'-hydroxybutyl)-3,6-
bis[4-(naphthalen-2-yl)phenyl]-9H-fluorene, and the like.
[0025]
20 Among these, preferred examples thereof can include 9,9-
bis(2'-hydroxyethyl)-2,7-dinaphthalen-2"-yl-9H-fluorene, and
9,9-bis(2'-hydroxyethyl)-2,7-dinaphthalen-1"-yl-9H-fluorene.
Such a compound may be used alone or two or more compounds may
be used in combination.
25 [0026]
[Method for Producing Compound Represented by General
Formula (1)]
14
The compound represented by General Formula (1) according
to the present embodiment can be synthesized by the following
steps (i) and (ii).
Step (i): Dihalogeno-9H-fluorene such as 2,7-dibromo-9Hfluorene
or 3,6-dibromo-9H-fluorene is treated 5 with a base (for
example, sodium hydroxide, potassium hydroxide, sodium
carbonate, potassium carbonate, sodium hydride, potassium
hydride, methoxy sodium, ethoxy sodium, t-butoxy sodium, tbutoxy
potassium, and n-butyllithium) in a solvent (for example,
10 tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide, N,Ndimethylacetamide,
dimethylsulfoxide, and sulfolane) to extract
9th hydrogen of dihalogeno-9H-fluorene, and thereafter, reacts
with hydroxyalkyl having a leaving group (here, examples of a
leaving group can include halogen such as chlorine, bromine,
15 iodine, a p-toluenesulfonyloxy group, a methylsulfonyloxy group,
a trifluoromethylsulfonyloxy group, and the like) to produce
9,9-bis(hydroxyalkyl)-dihalogeno-9H-fluorene such as 9,9-
bis(hydroxyalkyl)-2,7-dibromo-9H-fluorene or 9,9-
bis(hydroxyalkyl-3,6-9H-fluorene.
20 [0027]
Step (ii): 9,9-bis(hydroxyalkyl)-dihalogeno-9H-fluorene
such as 9,9-bis(hydroxyalkyl)-2,7-dibromo-9H-fluorene or 9,9-
bis(hydroxyalkyl)-3,6-9H-fluorene, which is obtained in Step
(i), reacts with naphthyl boric acid in a solvent (for example,
25 toluene and water, tetrahydrofuran and water, and dimethyl
sulfoxide and water) in the presence of a base (for example,
sodium carbonate, potassium carbonate, sodium acetate, potassium
15
acetate, sodium phosphate, and potassium phosphate) and a
palladium-based catalyst such as and tetrakis palladium
(triphenylphosphine) to produce the compound represented by
General Formula (1) of purpose under a condition of so-called
Suzuki-5 Miyaura Coupling.
[0028]
Here, the reaction of step (i) can be carried out at any
temperature between −78°C and the boiling point of the solvent.
In addition, as reaction conditions, general alkylation reaction
10 conditions can be applied. As desired, a hydroxy group of
hydroxyalkyl having a leaving group is protected with any
protecting group (for example, an ester group such as an acetyl
group), an ether group such as a tetrahydropyranyl group, a
carbonic acid ester group such as a t-butoxycarbonyl group, and
15 then may be deprotected at the end.
[0029]
The reaction of step (ii) can be carried out at any
temperature between room temperature and the boiling point of
the solvent. As reaction conditions, the reaction conditions
20 generally used in the so-called Suzuki-Miyaura coupling can be
applied.
[0030]
[Resin]
One aspect of the present invention is a resin obtained by
25 polymerization of a compound represented by General Formula (1).
Here, examples of the resin obtained by polymerization of
the compound represented by General Formula (1) include a
16
polyester resin, a polyurethane resin, a polycarbonate resin,
and a polyether resin.
[0031]
The polyester resin can be obtained by reacting the
compound represented by General Formula (5 1) with an aromatic
dicarboxylic acid (for example, terephthalic acid, isophthalic
acid, or 2,6-naphthalenedicarboxylic acid), or an aliphatic
dicarboxylic acid (for example, oxalic acid, malonic acid, or
succinic acid).
10 [0032]
The polyurethane resin can be obtained by reacting the
compound represented by General Formula (1) with an aromatic
diisocyanate (for example, toluene diisocyanate or xylylene
diisocyanate) or an aliphatic diisocyanate (for example,
15 pentamethylene diisocyanate, hexamethylene diisocyanate, or
cyclohexanedimethylene diisocyanate).
[0033]
As will be described later, the polycarbonate resin can be
obtained by reacting the compound represented by General Formula
20 (1) with a carbonate precursor such as a carbonic acid diester.
[0034]
The polyether resin can be obtained by reacting the
compound represented by General Formula (1) with an aliphatic
dihalogen compound (for example, dibromoethane or
25 dibromopropane) in presence of a base.
[0035]
In these resins, a reactant other than the compound
17
represented by General Formula (1) of the present application
may be used alone or a plurality of reactants may be used in
combination. In addition, it is also possible to polymerize a
resin by using a dihydroxy compound other than the compound
represented by General Formula (1) of the present 5 application,
in combination.
[0036]
In a case where the dihydroxy compound other than the
compound represented by General Formula (1) of the present
10 application is used in combination, a ratio of the compound
represented by General Formula (1) to the total amount of the
compound represented by General Formula (1) of the present
application and the dihydroxy compound other than the compound
represented by General Formula (1) is preferably equal to or
15 more than 5 mol% and equal to or less than 99 mol%, more
preferably equal to or more than 10 mol% and equal to or less
than 99 mol%, and even more preferably equal to or more than 15
mol% and equal to or less than 99 mol%.
[0037]
20 Here, examples of the dihydroxy compound other than the
compound represented by General Formula (1) include bis(4-
hydroxyaryl)alkanes such as 9,9-bis[4-(2-
hydroxyethoxy)phenyl]fluorene,9,9-bis[4-(2-hydroxyethoxy)-3-
methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-
25 ethylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-npropylphenyl]
fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-
isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-n18
butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-secbutylphenyl]
fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-tertbutylphenyl]
fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-
cyclohexylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-2-
phenylphenyl]fluorene, 9,9-bis[4-(2 5 -hydroxyethoxy)-3-
phenylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-(3-
methylphenyl)phenyl]fluorene, bis[4-(2'-
hydroxyethoxy)phenyl]sulfide, bis[4-(2'-hydroxyethoxy)-3-
methylphenyl]sulfide, bis[4-(2'-hydroxyethoxy)phenyl]sulfone,
10 bis[4-(2'-hydroxyethoxy)-3-methylphenyl]sulfone, bis[4-(2'-
hydroxyethoxy)phenyl]sulfoxide, bis[4-(2'-
hydroxyethoxy)phenyl]sulfoxide, bis(4-hydroxyphenyl)methane,
2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)ethane,
1,1-bis(4-hydroxyphenyl)phenylethane, 2,2-bis(4-hydroxy-3-
15 methylphenyl)propane, 2,2-bis(4-hydroxyphenyl)heptane, 2,2-
bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis(4-hydroxy-3,5-
dibromophenyl)propane, and 4,4-dihydroxyphenyl-1,1-mdiisopropylbenzene;
bis(hydroxyaryl)cycloalkanes such as 1,1-
bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-
20 hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-
trimethylcyclohexane, and 2,2,2,2-tetrahydro-3,3,3,3-
tetramethyl-1,1-spirobis[1H inden]-6,6-diol; dihydroxyaryl
ethers such as bis(4-hydroxyphenyl)ether, and bis(4-hydroxy-3,5-
dichlorophenyl)ether; 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-
25 bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-tertbutylphenyl)
fluorene, 9,9-bis(4-hydroxy-3-
isopropylphenyl)fluorene, 9,9-bis(4-hydroxy-3-
19
cyclohexylphenyl)fluorene, and 9,9-bis(4-hydroxy-3-
phenylphenyl)fluorene; ethylene glycol, 1,3-propanediol, 1,4-
butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,4-
cyclohexanedimethanol, 2,2-dimethyl-1,3-propanediol, 1,10-
decanediol, diethylene glycol, tetraethylene 5 glycol, norbornane
dimethanol, decahydronaphthalenedimethanol,
tricyclo[5.2.1.02,6]decandimethanol,
pentacyclopentadecanedimethanol, cyclopentane-1,3-dimethanol,
spiroglycol, and the like.
10 [0038]
[Polycarbonate Resin]
The polycarbonate resin according to the present embodiment
is produced by using the compound represented by General Formula
(1) according to the present embodiment. The polycarbonate
15 resin according to the present embodiment has a structural unit
represented by Formula (1p) and derived from the compound
represented by General Formula (1). Such a polycarbonate resin
can realize an optical molded article having a high refractive
index and excellent transparency. As a result, the
20 polycarbonate resin can be suitably used as a material for an
optical lens.
[0039]
20
[0040]
In Formula (1p), Ar1 and Ar2, R1 and R2, and o and p each are
synonymous with those in Formula (1). The same applies to the
preferred aspects.
5 [0041]
A preferred weight average molecular weight in terms of
polystyrene (Mw) of the polycarbonate resin according to the
present embodiment is preferably equal to or greater than 1.5 ×
103 and equal to or smaller than 2.0 × 105, and more preferably
10 equal to or greater than 2.0 × 103 and equal to or smaller than
1.2 × 105.
[0042]
In a case where Mw is equal to or greater than the above
lower limit value, it is preferable that the obtained molded
15 article can be suppressed from being fragile. In a case where
Mw is equal to or smaller than the above upper limit value, the
melt viscosity becomes more appropriate, so that the resin can
be easily taken out after production, fluidity further becomes
better, and injection molding becomes easier in a molten state,
20 which are preferable.
[0043]
A refractive index (nD) of the polycarbonate resin
according to the present embodiment at 23°C and a wavelength of
633 nm is preferably equal to or greater than 1.70 and equal to
25 or smaller than 1.85, more preferably equal to or greater than
1.70 and equal to or smaller than 1.82, even more preferably
equal to or greater than 1.71 and equal to or smaller than 1.81,
21
and particularly preferably equal to or greater than 1.72 and
equal to or smaller than 1.81.
[0044]
The polycarbonate resin according to the present embodiment
can be blended with another resin and used 5 for producing a
molded article. Examples of other resins include polyamide,
polyacetal, polycarbonate, modified polyphenylene ether,
polyethylene terephthalate, polybutylene terephthalate, and the
like.
10 [0045]
Furthermore, an antioxidant, a mold release agent, an
ultraviolet absorber, a fluidity modifier, a crystal nucleating
agent, a strengthening agent, a dye, an antistatic agent, an
antibacterial agent, and the like can be added to the
15 polycarbonate resin according to the present embodiment.
[0046]
Examples of a molding method include compression molding,
casting, roll processing, extrusion molding, stretching, and the
like, in addition to injection molding, but the molding method
20 is not limited thereto.
[0047]
In a case where the polycarbonate resin according to the
present embodiment is used for injection molding, the glass
transition temperature (Tg) is preferably equal to or higher
25 than 80°C and equal to or lower than 190°C, more preferably
equal to or higher than 85°C and equal to or lower than 180°C,
and even more preferably equal to or higher than 90°C and equal
22
to or lower than 170°C. In a case where Tg is equal to or
higher than the above lower limit value, a range of temperature
in use is wider, which is preferable. In a case where Tg is
equal to or lower than the above upper limit value, the melting
temperature of the resin decreases, and 5 decomposition and
coloring of the resin are less likely to occur, which is
preferable. In addition, in a case where Tg is equal to or
lower than the above upper limit value, the difference between
the mold temperature and the resin glass transition temperature
10 can be reduced even with a general-purpose mold temperature
controller. Therefore, it is easy to use and preferable in
applications in which strict surface accuracy is required for a
product.
[0048]
15 The optical molded article obtained by using the
polycarbonate resin according to the present embodiment
preferably has a total transmittance of equal to or greater than
82%, more preferably has a total transmittance of equal to or
greater than 85%, in which each total transmittance is measured
20 in accordance with JIS K-7361-1 (1997), and is by no means
inferior to a bisphenol A-type polycarbonate resin and the like.
[0049]
[Method for Producing Polycarbonate Resin]
The polycarbonate resin according to the embodiment can be
25 produced by using the compound represented by General Formula
(1) as a raw material. Specifically, the compound represented
by General Formula (1) reacts with a carbonate precursor such as
23
a carbonic acid diester by a melt polycondensation method, in
presence of a basic compound catalyst, a transesterification
catalyst, or a mixed catalyst constituted of both, or in absence
of a catalyst, to produce the polycarbonate resin.
5 [0050]
Examples of the carbonic acid diester used to produce the
polycarbonate resin according to the present embodiment include
diphenyl carbonate, di-p-tolyl carbonate, di-m-tolyl carbonate,
di-o-tolyl carbonate, bis(p-chlorophenyl)carbonate, bis(m10
chlorophenyl)carbonate, bis(o-chlorophenyl)carbonate, m-cresyl
carbonate, dimethyl carbonate, diethyl carbonate, di-n-butyl
carbonate, dicyclohexyl carbonate, and the like. Among these,
diphenyl carbonate is preferred. Diphenyl carbonate is
preferably used in a ratio of 0.97 to 1.20 mol and more
15 preferably used in a ratio of 0.98 to 1.10 mol, with respect to
1 mol of the compound represented by General Formula (1).
[0051]
Examples of the basic compound catalyst used in the
production of the polycarbonate resin according to the present
20 embodiment include alkali metal compounds, alkaline earth metal
compounds, nitrogen-containing compounds, and the like. As such
compounds, organic acid salts, inorganic salts, oxides,
hydroxides, hydrides or alkoxides, or quaternary ammonium
hydroxides and salts thereof, amines, or the like of alkali
25 metals, alkaline earth metal compounds, or the like are
preferably used, and these compounds can be used alone or in
combination.
24
[0052]
Examples of the alkali metal compounds include organic acid
salts, inorganic salts, oxides, hydroxides, hydrides, alkoxides,
and the like of alkali metals. Specific examples thereof for
use include sodium hydroxide, potassium 5 hydroxide, cesium
hydroxide, lithium hydroxide, sodium hydrogencarbonate, sodium
carbonate, potassium hydrogencarbonate, potassium carbonate,
cesium carbonate, lithium carbonate, sodium acetate, potassium
acetate, cesium acetate, lithium acetate, sodium stearate,
10 potassium stearate, cesium stearate, lithium stearate, sodium
borohydride, sodium borophenylate, sodium benzoate, potassium
benzoate, cesium benzoate, lithium benzoate, disodium
hydrogenphosphate, dipotassium hydrogenphosphate, dilithium
hydrogenphosphate, disodium phenylphosphate, a disodium salt, a
15 dipotassium salt, a dicesium salt, or a dilithium salt of
bisphenol A, a sodium salt, a potassium salt, a cesium salt, or
a lithium salt of phenol, and the like.
[0053]
Examples of the alkaline earth metal compounds include
20 organic acid salts, inorganic salts, oxides, hydroxides,
hydrides, alkoxides, or the like of alkaline earth metal
compounds. Specific examples thereof for use include magnesium
hydroxide, calcium hydroxide, strontium hydroxide, barium
hydroxide, magnesium hydrogencarbonate, calcium
25 hydrogencarbonate, strontium hydrogencarbonate, barium
hydrogencarbonate, magnesium carbonate, calcium carbonate,
strontium carbonate, barium carbonate, magnesium acetate,
25
calcium acetate, strontium acetate, barium acetate, magnesium
stearate, calcium stearate, calcium benzoate, magnesium
phenylphosphate, and the like.
[0054]
Examples of the nitrogen-containing 5 compounds include
quaternary ammonium hydroxides and salts thereof, amines, and
the like. Specific examples thereof for use include quaternary
ammonium hydroxides having an alkyl group such as
tetramethylammonium hydroxide, tetraethylammonium hydroxide,
10 tetra n-propylammonium hydroxide, tetra n-butylammonium
hydroxide, trimethylbenzylammonium hydroxide, or an aryl group;
tertiary amines such as triethylamine, dimethylbenzylamine,
triphenylamine; secondary amines such as diethylamine and
dibutylamine; primary amines such as n-propylamine and n15
butylamine; imidazoles such as 2-methylimidazole, 2-
phenylimidazole, and benzoimidazole; or bases such as ammonia,
tetramethylammonium borohydride, tetra n-butylammonium
borohydride, tetra n-butylammonium tetraphenylborate,
tetraphenylammonium tetraphenylborate, or basic salts, and the
20 like.

CLAIMS
1. A compound represented by General Formula (1),
wherein in General Formula (1), Ar1 and 5 Ar2 independently
represent a group selected from the following formulae,
where, R1 to R6 each represent a hydrogen atom, a
66
hydrocarbon group, or a heteroatom-containing hydrocarbon group,
A1 to A5 and B1 to B5 each represent a hydrogen atom, a
hydrocarbon group, or a heteroatom-containing hydrocarbon group,
at least one of A1 to A5 is a -Y1-Ar3 group,
at least one of B1 to B5 5 is a -Y2-Ar4 group,
Y1 and Y2 each represent a single bond or a linking group,
Ar3 and Ar4 each represent an aromatic group,
X1 to X4 each are -O-, -S-, -NR'-, or -C(Me)2-,
Z1 to Z4 each represent a hydrocarbon atom, a hydrocarbon
10 group, or a heteroatom-containing hydrocarbon group,
R' represents a hydrogen atom, a hydrocarbon group, or a
heteroatom-containing hydrocarbon group, and
o and p each represent an integer of 1 to 4.
15 2. The compound according to claim 1, wherein in General
Formula (1), o and p each are 2.
3. The compound according to claim 1 or 2, wherein in General
Formula (1), Ar1 and Ar2 independently represent a group selected
20 from the following formulae,
where, R1 to R6 each represent a hydrogen atom, a
hydrocarbon group, or a heteroatom-containing hydrocarbon group,
and
67
o and p each represent an integer of 1 to 4.
4. A resin obtained by polymerization of the compound
represented by General Formula (1) according to any one of
5 claims 1 to 3.
5. A polycarbonate resin derived from the compound represented
by General Formula (1) according to any one of claims 1 to 3.
10 6. An optical molded article containing the resin according to
claim 4 or 5.
7. The optical molded article according to claim 6, wherein the
optical molded article is an optical lens.
15
8. The optical molded article according to claim 6, wherein the
optical molded article is an optical film.