JPH0643301A - Optical parts - Google Patents

Abstract

(57) [Summary] [Purpose] Has low birefringence and excellent heat resistance.
Moreover, it is to provide an optical component having high adhesion of the photosensitive resin layer. An optical component in which a photosensitive resin tank is provided on the surface of a base material made of polycarbonate, polyester carbonate or polyester having a norbornane skeleton, a dimethanoperhydronaphthalene skeleton or a trimetanoperhydroanthracene skeleton.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION This invention relates to optical components.

[0002]

2. Description of the Related Art In recent years, optical components such as a diffraction grating and a flat plate microlens array having fine irregularities on the surface of a transparent substrate have been widely used. For example, a diffraction grating is used for a laser beam splitting element in an optical disk pickup, an optical low-pass filter for an image display device, and the like, in addition to conventional spectral applications. As the flat plate microlens array, there is an array formed on each pixel of a CCD or a liquid crystal panel.

Currently, as a method of manufacturing an optical component having an uneven surface, (1) a photoresist is applied on a glass substrate to form a resist pattern, and then the glass is etched to form a surface uneven pattern on the glass surface. (2) Injection molding using a transparent resin such as polymethylmethacrylate (PMMA), (3) Glass, PM
MA, bisphenol A type polycarbonate (P
C), there is a method in which a photosensitive resin film is formed on a transparent resin substrate such as an amorphous polyolefin, and unevenness is formed by photolithography.

[0004]

Each of the above methods for producing an optical component having surface irregularities has the following problems. (1) In the method of forming a concavo-convex pattern by etching a glass substrate, good optical characteristics and durability can be obtained by using a glass substrate that has been precisely polished, but the photolithography process and etching process are complicated, Productivity is low. (2) The injection molding method using PMMA or the like is excellent in productivity, but it is difficult and time-consuming to produce a highly accurate die, and the die production cost is also high. (3) Among the methods of forming irregularities on the surface by photolithography, when glass is used as the substrate, the optical performance and durability are excellent, but the precision-polished glass substrate is expensive. When a transparent resin substrate is used as the substrate,
Although the cost is low, there are the following problems depending on the substrate material used.

Since PMMA has a large saturated water absorption rate of about 2%, the dimensional change due to water absorption is large, and the performance deteriorates when used under high humidity. Also, the glass transition temperature is 100
Since it is below ℃, there is a limit to use at high temperature. P
In C, the saturated water absorption is 0.4% and the glass transition temperature is 14%.
At 0 ° C., it is superior to PMMA in terms of water absorption and heat resistance, but it has a large birefringence and cannot be used particularly in applications using polarized light. There is also a problem that the surface hardness is low and scratches are likely to occur. Amorphous polyolefin does not have a polar group, and thus has a problem of low adhesion to a photosensitive resin.

An object of the present invention is to provide an optical component having a small birefringence, excellent heat resistance, and high adhesiveness of a photosensitive resin layer.

[0007]

The above object of the present invention is to:
This is achieved by an optical component in which a photosensitive resin layer is provided on the surface of a substrate made of a polycarbonate, a polyester carbonate or a polyester having a norbornane skeleton, a dimethanoperhydronaphthalene skeleton or a trimetanoperhydroanthracene skeleton.

That is, the present invention is represented by the following general formulas (I) to (III)

[Chemical 4] Of the structural units (I) to (III), and the molar fraction (x) of the structural unit (I) is the structural unit (I).
A base material made of a resin substantially equal to the total mole fraction (y + z) of the mole fraction (y) of I) and the mole fraction (z) of the structural unit (III), the above structural units (I) and ( II) and the mole fraction (x) of the structural unit (I) is the structural unit (II)
A substrate consisting of a resin substantially equal to the mole fraction (y) of
Alternatively, a substrate comprising a resin comprising the above structural units (I) and (III), the molar fraction (x) of the structural unit (I) being substantially equal to the molar fraction (z) of the structural unit (III). An optical component having a photosensitive resin layer provided on the surface thereof.

In the resin of the present invention, the molar fraction (x) of the structural unit (I) represented by the general formula (I) is about 50 mol%.
Is. The molar fraction (y) of the structural unit (II) represented by the general formula (II) is in the range of 50 mol% or less, preferably 40 mol% or more and 50 mol% or less.
If the content is less than 20 mol%, the water absorption may not be sufficiently low, which is not preferable. Further, the base material obtained from the polyester carbonate containing a small amount of the structural unit (III) represented by the general formula (III) is superior to the base material obtained from the polycarbonate containing no structural unit (III). Excellent mechanical properties. The preferable mole fraction (z) of the structural unit (III) is 1 mol% or more and 20 mol% or less.
It should be noted that a small amount of any other structural unit may be contained within a range in accordance with the object of the present invention. The polymerization rate is usually 10 mol% or less.

The n in the structural unit (I) is preferably 1 or 2 from the viewpoint that a base material having high heat resistance and a low absorptivity can be obtained, and 1 from the viewpoint of easy production of the raw material compound. Is more preferable. Specific examples of the structural unit (I) include the following.

[Chemical 5] Further, as A in the structural unit (III), a divalent saturated alicyclic hydrocarbon group having 20 or less carbon atoms is preferable from the viewpoint that a base material having low birefringence and water absorption and high heat resistance can be obtained. Specific examples of the structural unit (III) include the following.

[Chemical 6]

The resin used in the present invention can be produced by a known appropriate method. That is, the corresponding acid, its ester, acid chloride (phosgene for the structural unit (II)), acid anhydride, diol, its ester or alkoxide, etc. is used as a raw material, and the interface method, solution method, melting method, etc. The resin of the present invention can be obtained by the above method. During the reaction, a catalyst can be used if necessary. Examples of the catalyst include (1) various alkoxides, (2) alkali metal, (3) alkali metal hydride, (4) alkali metal hydroxide, and (5) metal halide.
Although the amount of the catalyst used is not particularly limited, it is usually in the range of 0.0001 to 1 mol% with respect to the entire raw material.

The reaction conditions vary depending on the starting material and the manufacturing method used. For example, when the corresponding ester and diol are manufactured by the melting method, the starting material and the catalyst are inert such as nitrogen, argon, carbon dioxide, etc. The reaction can be advanced by heating and stirring in a gas atmosphere and distilling phenol when the generated alcohol or phenyl ester is used. The reaction temperature varies depending on the raw material used, the boiling point of the alcohol or phenol produced, and the like, but is usually in the range of 150 to 300 ° C. The reaction time is usually selected from the range of 30 minutes to 10 hours.
In the latter half of the reaction, the system is depressurized as necessary to drive the reaction, but the pressure at this time is usually 0.001 to 100 mmHg.
Is the range. The produced resin can be taken out of the reaction tank in any state such as powder, lump or pellet, and can be used for molding by the same method as that for general transparent resin for molding.

Regarding the molecular weight of the resin in the present invention,
The average molecular weight (converted to polystyrene) by gel permeation chromatography (GPC) is preferably 10,000 or more and 100,000 or less, and 20,0.
It is more preferably from 00 to 80,000.
A resin having a number average molecular weight of 10,000 or less is brittle and sufficient strength cannot be obtained, and it is difficult to synthesize a resin having a number average molecular weight of 100,000 or more.

As the photosensitive resin in the present invention, various resins can be used as long as they are exposed to visible light or deep ultraviolet light and unevenness is formed by a developing process. Examples of the method for forming the photosensitive resin layer on the base material include a spin coating method and a dipping method.

The base material forming the optical component of the present invention is formed by a melt molding method such as a press molding method, an extrusion molding method, an injection molding method, an injection compression molding method, or a casting method.

[0016]

EXAMPLES The present invention will be described below with reference to examples. The methods for measuring physical properties and test conditions are as follows. Birefringence value: A single-pass value was measured by vertically injecting 633 nm laser light using an ellipsometer. Adhesion of the photosensitive resin film: The adhesiveness of the photosensitive resin film was confirmed by sticking cellophane tape on the surface having the irregularities and then peeling it off. Heat resistance: It was left in an oven at 100 ° C. for 24 hours, and it was confirmed whether or not there was a change in appearance and diffraction efficiency.

(Example 1) 2,3-represented by the following formula
Di (hydroxymethyl) -perhydro-1,4: 5,8
-Dimethanonaphthalene

[Chemical 7] And diphenyl carbonate represented by the following formula

[Chemical 8] It is composed of a colorless transparent resin (number average molecular weight (GPC conversion): 37,000) having a structure as shown in the following formula by a melt polycondensation reaction using tetrabutylammonium tetraphenylborate as a catalyst, using and as starting materials. A long cylindrical chip was obtained.

[Chemical 9] The chip was dried, a resin plate having a thickness of 1 mm was molded by an extrusion molding machine, and cut into a disk having a diameter of 150 mm to prepare a disk-shaped transparent resin base material. Commercially available positive photoresist is coated on the above base material so as to have a thickness of 0.2 μm,
After drying, it was exposed to ultraviolet light through a photomask having a one-dimensional linear opening having a pitch of 30 μm. After developing with an alkaline aqueous solution, it was dried, and the entire surface was irradiated with ultraviolet rays to remove the coloring of the resist, and a diffraction grating was produced.

Example 2 As a raw material, 2,3-di (hydroxymethyl) -perhydro-1,4: 5,8-
Instead of dimethanonaphthalene, the following formula

[Chemical 10] A chip made of a colorless transparent resin (number average molecular weight: 33000) having a structure represented by the following formula was obtained in the same manner as in Example 1 except that the compound represented by To produce a diffraction grating.

[Chemical 11]

(Example 3) As a raw material, 2,3-di (hydroxymethyl) -perhydro-1,4: 5,8-
Dimethanonaphthalene and the following formula

[Chemical 12] A chip made of a colorless transparent resin (number average molecular weight: 39000) having a structure represented by the following formula was prepared in the same manner as in Example 1 except that a mixture with the compound represented by (molar ratio: 1: 1) was used. Then, a diffraction grating was produced from this in the same manner as in Example 1.

[Chemical 13]

(Example 4) 2,3-di (hydroxy) -perhydro-1,4 used in Example 1 as a starting material:
5,8-Dimethanonaphthalene and diphenyl carbonate and the following formula (IV)

[Chemical 14] A mixture with a compound represented by (molar ratio: 10: 9: 1)
A colorless and transparent resin having a structure represented by the following formula (average molecular weight: 29000) in the same manner as in Example 1 except that
A chip made of was obtained, and a diffraction grating was produced in the same manner as in Example 1.

[Chemical 15]

Example 5 As a raw material, 2,3-di (hydroxy) -perhydro-1, used in Example 1, was used.
A structure represented by the following formula was obtained in the same manner as in Example 1 except that a mixture (molar ratio: 1: 1) of 4: 5,8-dimethanonaphthalene and the compound represented by the above formula (IV) was used. A chip made of the colorless transparent resin (number average molecular weight: 32000) was obtained, and a diffraction grating was prepared in the same manner as in Example 1.

[Chemical 16]

Comparative Example 1 PMMA as a base material
(Using Kuraray Co., Ltd. Parapet H-1000),
A diffraction grating was produced in the same manner as in Example 1. (Comparative Example 2) A diffraction grating was produced in the same manner as in Example 1 by using PC (Panlite AD-5503 manufactured by Teijin Chemicals Ltd.) as a base material. (Comparative Example 3) A diffractive grating was produced in the same manner as in Example 1, using an alicyclic polyolefin (Zeonex 280 manufactured by Nippon Zeon Co., Ltd.) as a base material.

Table 1 shows the results of measurement of birefringence, film adhesion and heat resistance of the diffraction gratings produced in Examples 1 to 5 and Comparative Examples 1 to 3 above.

[Table 1]

[0024]

According to the present invention, there is provided an optical component having a small birefringence, excellent heat resistance, and high adhesiveness to a photosensitive resin layer.

Claims (3)

[Claims] 1. The following general formulas (I) to (III): Of the structural units (I) to (III), and the molar fraction (x) of the structural unit (I) is the structural unit (I).
A photosensitive resin layer is provided on the surface of a substrate made of a resin that is substantially equal to the total mole fraction (y + z) of the mole fraction (y) of I) and the mole fraction (z) of the structural unit (III). An optical component characterized in that 2. The following general formulas (I) and (II): The structural unit (I) and the structural unit (II) are represented respectively, and the molar fraction (x) of the structural unit (I) is the structural unit (II).
The optical component is characterized in that a photosensitive resin layer is provided on the surface of a base material made of a resin that is substantially equal to the molar fraction (y). 3. The following general formulas (I) and (III): The structural unit (I) and the structural unit (III) are respectively represented, and the mole fraction (x) of the structural unit (I) is the structural unit (II
An optical component, wherein a photosensitive resin layer is provided on the surface of a base material made of a resin substantially equal to the molar fraction (z) of I).