JP6513455B2 - Polishing pad - Google Patents

Polishing pad Download PDF

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JP6513455B2
JP6513455B2 JP2015076928A JP2015076928A JP6513455B2 JP 6513455 B2 JP6513455 B2 JP 6513455B2 JP 2015076928 A JP2015076928 A JP 2015076928A JP 2015076928 A JP2015076928 A JP 2015076928A JP 6513455 B2 JP6513455 B2 JP 6513455B2
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polishing
polishing pad
layer
polishing layer
hardness
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JP2016196066A (en
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博仁 宮坂
博仁 宮坂
哲平 立野
哲平 立野
香枝 喜樂
香枝 喜樂
立馬 松岡
立馬 松岡
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富士紡ホールディングス株式会社
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Description

  The present invention relates to a polishing sheet or pad for polishing materials requiring high surface flatness such as optical materials, substrates for semiconductors, semiconductor wafers, hard disk substrates, glass substrates for liquid crystals, semiconductor devices and the like.

  Optical materials, semiconductor substrates, semiconductor wafers, hard disk substrates, glass substrates for liquid crystals, and semiconductor devices are required to have extremely precise flatness. In addition, on the surface of the semiconductor material, various materials having different hardness such as metal, organic and inorganic insulating materials are exposed. In order to flatly polish the surface of such a material, it is necessary that the surface of the polishing pad is always flat. If the stiffness of the surface of the polishing pad changes during the polishing operation, the desired flatness can not be achieved. For example, due to the surface of the polishing pad which is locally lowered in rigidity, precise flatness can not be achieved, and a phenomenon (dishing) in which only the metal portion is preferentially polished occurs.

  On the other hand, considerable polishing debris is generated at the end of one polishing operation from the start of polishing to replacement of the polishing pad and the polishing liquid. The surface temperature of the material to be polished during one polishing operation is from the beginning to the end of the polishing operation, since the accumulation of polishing debris causes the opening to be clogged, resulting in deterioration of the retention of the slurry and generation of frictional heat. It rises and changes in a wide temperature range including 30 ° C-90 ° C. Therefore, a change in local stiffness of the surface of the polishing pad may occur in response to this temperature change. In addition, since the polishing liquid used for chemical mechanical polishing has a strong chemical action (corrosion of the surface of the non-polished material) as the temperature rises, it tends to be susceptible to larger scratches.

In paragraph 0072 of Patent Document 1 (Japanese Patent Laid-Open No. 2008-207324), the D hardness [D (23 ° C., wet)] of the polishing pad at 23 ° C. when saturated swelling with warm water at 50 ° C. The ratio [[D (23 ° C., wet)] / [D (23 ° C., dry)] of the D hardness [D (23 ° C., dry)] of the polishing pad is about 0.9 to 1.1, It is described that a polishing pad having this ratio of 0.9 or more can be obtained by a polishing pad having an [E ′ (50 ° C., dry)] / [E ′ (50 ° C., wet)] of about 2.5 or less. There is.
On the other hand, in the same paragraph 0068, although the polyurethane elastic body has a large temperature dependence of the storage elastic modulus, and the temperature dependence thereof changes by absorbing water, generally, the polyurethane elastic body [E '( 23 ° C., wet) / E ′ (50 ° C., wet)] is large (eg, about 2.5 to 20), and in the polishing pad of Patent Document 1, for example, the glass transition temperature is 50 ° C. or more, and the water absorption rate [E '(23 ° C., wet) / E' (50 ° C., wet)] of the polishing pad can be lowered by highly packing ultrafine single fibers composed of a thermoplastic resin such as 4% by mass or less It describes what can be done.
Patent Document 1 proposes to further reduce the difference in hardness between dry and wet states, but discloses that this problem is difficult only with a polyurethane elastic body.

  Patent Document 2 (Japanese Patent Laid-Open No. 2006-144156) discloses a polishing pad capable of stably providing a high level of flatness by suppressing the difference in Shore A hardness at room temperature and 60 ° C. heating to 14 or less. It is done. However, Patent Document 2 does not describe the difference in hardness between the surface of the polishing layer and the inside.

JP, 2008-207324, A JP, 2006-144156, A

  The present invention provides a polishing pad in which the surface of the polishing layer is softened during polishing.

That is, the present invention provides the following.
[1]
A polishing pad having a polishing layer made of polyurethane resin, comprising:
The polishing layer is formed by curing a polyurethane resin curable composition including a polyisocyanate compound, a polyol compound, a curing agent, and micro hollow spheres.
Following formula:
{(D hardness at 20 ° C. of the polishing layer in a dry state) - (D hardness of 40 ° C. abrasive layer warm water saturation swelling of)} / (D hardness at 20 ° C. of the polishing layer in the dry state)
The value of is 0.1 to 0.3,
Following formula:
{(Storage modulus of dry polishing layer at 40 ° C. ) − (Storage modulus of polishing layer saturated swollen with warm water of 40 ° C.)} / (Storage modulus of dry polishing layer at 40 ° C. ) )
The value of is 0.4 to 0.9 ,
A polishing pad characterized by
[2]
The polishing pad according to [1], wherein the polyisocyanate compound and the polyol compound comprise a prepolymer prepared by the reaction of the polyisocyanate compound and the polyol compound.
[3]
The curing agent has a total amount of curing agent of 100% by weight and the following formula:
The polishing pad in any one of [1]-[2] which contains 3-8 weight% of tetramers represented by these.
[4]
A method of polishing a surface of an optical material or a semiconductor material, characterized by using the polishing pad according to any one of [1] to [3] .
[5]
The method to reduce the scratch at the time of grinding | polishing the surface of an optical material or a semiconductor material using the polishing pad in any one of [1]- [3] .

  According to the present invention, defects such as scratches on the object to be polished can be suppressed by softening the surface of the polishing layer at the time of polishing (about 40 ° C.). Moreover, a high polishing rate can be maintained by providing an appropriate hardness inside the polishing layer.

(Polishing pad)
The polishing pad of the present invention has a polishing layer made of a foamed polyurethane resin. The polishing layer is disposed in direct contact with the material to be polished, and the other part of the polishing pad may be made of a material for supporting the polishing pad, for example, an elastic material such as rubber. Depending on the rigidity of the polishing pad, the entire polishing pad can be one polishing layer.

  The polishing pad according to the present invention is similar to the general polishing pad in the shape except for the fact that defects such as scratches are less likely to occur in the material to be polished during the accumulation of polishing debris, and it is used like the general polishing pad. For example, the polishing layer can be pressed against the material to be polished for polishing while rotating the polishing pad, or the material to be polished can be pressed against the polishing layer for polishing.

A feature of the polishing pad of the present invention is that the polishing layer is formed by curing a polyurethane resin curable composition containing a polyisocyanate compound, a polyol compound, a curing agent, and micro hollow spheres.
The following formula (I):
{(D hardness at 20 ° C. of the polishing layer in a dry state) - (D hardness of 40 ° C. abrasive layer warm water saturation swelling of)} / (D hardness at 20 ° C. of the polishing layer in the dry state)
The value of is 0.1 to 0.3, more preferably 0.15 to 0.25,
The following formula (II):
{(Storage modulus of dry polishing layer at 40 ° C. ) − (Storage modulus of polishing layer saturated swollen with warm water of 40 ° C.)} / (Storage modulus of dry polishing layer at 40 ° C. ) )
The value of is 0.4 to 0.9, more preferably 0.6 to 0.85.
The present inventors have found that the polishing characteristics of the polishing pad can be improved by limiting the values of the above formulas (I) and (II) to a specific range. The numerical range of the above formula (I) means that the D hardness of the polishing layer in the wet state is reduced by 10 to 30% as compared to that in the drying, and the numerical range of the above formula (II) is the storage elasticity of the polishing layer in the wet state It means that the rate is reduced by 40 to 90% compared to that at the time of drying. That is, by the time the polishing temperature reaches 40 ° C., the hardness and elastic modulus of the surface of the polishing layer of the polishing pad of the present invention decrease, and the surface is deformed so as not to cause conditions such as scratches. Since the deformation is limited to the surface of the polishing pad, the hardness and elastic modulus of the entire polishing pad are not lowered so much that desired flatness and polishing rate can not be obtained.
Further, since the bubbles of the polishing layer of the present invention are closed bubbles and the bubbles do not communicate with each other, even if the surface of the polishing layer is exposed to water, the water does not penetrate into the polishing layer through the bubbles. , The internal dryness is maintained.

(Method of manufacturing polishing pad)
The polishing pad of the present invention can be produced by generally known production methods such as molding and slab molding. First, a block of polyurethane is formed by these manufacturing methods, the block is formed into a sheet by slicing or the like, an abrasive layer formed of a polyurethane resin is formed, and the block is laminated to a support or the like. Alternatively, the polishing layer can be formed directly on the support.

  More specifically, the polishing layer has a double-sided tape attached to the side opposite to the polishing surface of the polishing layer, and is cut into a predetermined shape to become the polishing pad of the present invention. There is no particular limitation on the double-sided tape, and any double-sided tape known in the art can be selected and used. The polishing pad of the present invention may have a single layer structure consisting only of the polishing layer, and a multilayer in which another layer (lower layer, support layer) is bonded to the surface opposite to the polishing surface of the polishing layer. It may be composed of

  The polishing layer is formed by preparing a polyurethane resin curable composition containing a polyisocyanate compound and a polyol compound, and curing the polyurethane resin curable composition.

  The polishing layer is composed of a foamed polyurethane resin, but the foaming can be carried out by dispersing a foaming agent containing micro hollow spheres in the polyurethane resin, in which case a polyurethane comprising a polyisocyanate compound, a polyol compound and a foaming agent It is molded by preparing a resin foam curable composition and subjecting the polyurethane resin foam curable composition to foam curing.

  The polyurethane resin curable composition can also be, for example, a two-component composition prepared by mixing solution A containing a polyisocyanate compound and solution B containing other components. The liquid B containing other components can be further divided into a plurality of liquids to form a composition constituted by mixing three or more liquids.

  The polyisocyanate compound may comprise a prepolymer prepared by the reaction of a polyisocyanate compound and a polyol compound as commonly used in the art. As prepolymers, those generally used in the art containing unreacted isocyanate groups can also be used in the present invention.

(Isocyanate component)
As an isocyanate component, for example,
m-phenylene diisocyanate,
p-phenylene diisocyanate,
2,6-Tolylene diisocyanate (2,6-TDI),
2,4-tolylene diisocyanate (2,4-TDI),
Naphthalene-1,4-diisocyanate,
Diphenylmethane-4,4'-diisocyanate (MDI),
4,4'-Methylene-bis (cyclohexyl isocyanate) (hydrogenated MDI),
3,3'-dimethoxy-4,4'-biphenyl diisocyanate,
3,3'-Dimethyldiphenylmethane-4,4'-diisocyanate,
Xylylene-1,4-diisocyanate,
4,4'-diphenylpropane diisocyanate,
Trimethylene diisocyanate,
Hexamethylene diisocyanate,
Propylene-1,2-diisocyanate,
Butylene-1,2-diisocyanate,
Cyclohexylene-1,2-diisocyanate,
Cyclohexylene-1,4-diisocyanate,
p-phenylene diisothiocyanate,
Xylylene-1,4-diisothiocyanate,
Ethylidine diisothiocyanate and the like can be mentioned.

(Polyol component)
As a polyol component, for example,
Ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, pentanediol, 3-methyl-1, Diols such as 5-pentanediol, 1,6-hexanediol;
Polyether polyols such as polytetramethylene glycol (PTMG), polyethylene glycol, polypropylene glycol;
Polyester polyols such as a reaction product of ethylene glycol and adipic acid or a reaction product of butylene glycol and adipic acid;
Polycarbonate polyol;
Polycaprolactone polyol;
Etc.

(Hardening agent)
The curing agent is a compound which is reacted with the isocyanate group in the prepolymer to complete the polyurethane resin when the prepolymer is used as a polyisocyanate compound. In the present invention, for example, the curing agent described below can be exemplified.

  The polyol used as the curing agent is the same as the polyol component described above. In addition, triols such as trifunctional glycerin and polyols having four or more functional groups can also be used.

Examples of polyamines include diamines, which are alkylene diamines such as ethylene diamine, propylene diamine and hexamethylene diamine; diamines having an aliphatic ring such as isophorone diamine and dicyclohexylmethane-4,4'-diamine; , A diamine having an aromatic ring such as 3'-dichloro-4,4'-diaminodiphenylmethane (alias: methylene bis-o-chloroaniline) (hereinafter abbreviated as MOCA);
Diamine having a hydroxyl group such as 2-hydroxyethylethylenediamine, 2-hydroxyethylpropylenediamine, di-2-hydroxyethylethylenediamine, di-2-hydroxyethylpropylenediamine, 2-hydroxypropylethylenediamine, di-2-hydroxypropylethylenediamine, etc. In particular hydroxyalkyl alkylene diamines;
Etc. Further, trifunctional triamine compounds and tetrafunctional or higher functional polyamine compounds can also be used.
A particularly preferred curing agent is the above mentioned MOCA, and the chemical structure of this MOCA is
It is. MOCA contains tetramer as a by-product, and the chemical structure of tetramer is
It is. It is preferable that the total amount of the curing agent is 100% by weight and that the tetramer is 3 to 10% by weight, preferably 4 to 8% by weight, more preferably 5 to 7% by weight.

(Foaming agent)
Foams can be formed by mixing micro hollow spheres with a polyurethane resin. Micro hollow spheres refer to those obtained by heating and expanding unexpanded heat expandable microspheres comprising an outer shell (polymer shell) made of a thermoplastic resin and a low boiling point hydrocarbon contained in the outer shell. . As said polymer shell, thermoplastic resins, such as an acrylonitrile vinylidene chloride copolymer, an acrylonitrile methyl methacrylate copolymer, a vinyl chloride ethylene copolymer, etc. can be used, for example. Similarly, as low boiling point hydrocarbons contained in the polymer shell, for example, isobutane, pentane, isopentane, petroleum ether and the like can be used.

(Other ingredients)
In addition, catalysts commonly used in the art may be added to the foam curable composition.

  The invention will be described experimentally by means of the following examples, which are not intended to be construed as limiting the scope of the invention to the following examples.

(material)
The materials used in the following examples are listed.
-Name of urethane prepolymer:
Uniroyal made ADIPRENE L325
DIC Corporation Pandex C730
Novaretan UP-127 manufactured by Mitsubishi Plastics
-Product name of MOCA:
DIC Corporation Pandex E, Pandex E 50
Brand name of LM-52 amine and hollow particles manufactured by Ihara Chemical Co .:
Nippon Fillite Ltd. EXPANCEL 551DE40d42
Matsumoto Oil & Fats Co. Matsumoto Microsphere F-80 DE

Example 1
Component A 100 g (parts) of urethane prepolymer (Pandex C 730) of NCO equivalent 460 having tolylene diisocyanate as main component, component B: curing agent Pandex E and Pandex E 50 in a weight ratio of 1: 1 30.75 g (parts) of a mixture (containing 100% by weight of curing agent and 6.0% by weight of tetramer), 2.25 g (parts) of hollow fine particles to component C (EXPANCEL 551 DE 40d 42 and Matsumoto Micro Prepare spheres F-80DE 4: 1) respectively. In addition, in order to show a ratio, it describes as g indication, and prepares a required weight (part) according to the size of a block. The same applies to g (parts) notation.
The components A and B were previously degassed under reduced pressure, respectively, and then the components A, B and C were supplied to the mixer.
The obtained mixed solution was cast in a mold (890 mm × 890 mm square) heated to 80 ° C., heated and cured for 5 hours, and then the formed resin foam was removed from the mold. The foam was sliced to a thickness of 1.3 mm to prepare a urethane sheet, to obtain a polishing pad.

(Example 2)
Component A: 100 g (parts) of a urethane prepolymer (Novaletan UP-127) having an NCO equivalent of 400 containing tolylene diisocyanate as a main component, and B: Pandex E as a curing agent and LM-52 amine in a weight ratio of 7: 30.5 g (parts) of a mixture of 3 (containing 0.5 wt% of the curing agent and 100 wt% of the curing agent), 2.0 g (parts) of hollow fine particles in the C component (EXPANCEL 551 DE 40 d 42) Prepare Matsumoto Microsphere F-80DE 4: 1) respectively.
Thereafter, a urethane sheet was prepared in the same manner as in Example 1 to obtain a polishing pad.

(Comparative example 1)
As a comparative example, IC1000 which is a polishing pad manufactured by Nitta Haas was used.

(Hardness, storage modulus E ', scratch)
D hardness was measured according to JIS K6253-1997 / ISO 7619.
Storage modulus E '(MPa) is calculated by TA Instruments Japan RSAII
According to I, according to JIS K7244-4, the initial load was 10 g, the strain range was 0.01 to 4%, and the measurement frequency was measured at 40 ° C. at 0.2 Hz. The temperature was measured at 40 ° C. for both drying and wetting.
The dry state of the polishing pad is defined as a state of being left under conditions of 20 ± 2 ° C., humidity 65 ± 5% for 2 hours or more, and the wet state of the polishing pad is immersed in 40 ° C. ± 2 deionized water for 1 hour Defined as a swollen state.
For evaluation of defects such as scratches, 25 substrates are polished, and 21 to 2 after polishing processing
Wafer surface inspection system (Surfsc manufactured by KLA Tencor Co., Ltd.) for five fifth substrates
The number of defects such as scratches on the surface of the substrate was evaluated in the high sensitivity measurement mode of an. In the evaluation of defects such as scratch, 12 inches (
Less than 200 defects with a diameter of 0.16 μm or more on the wafer of 300 mmφ) were marked with ○, and 200 or more with x.

(Polishing rate)
The conditions of the polishing test are as follows.
・ Used polisher: F-REX 300 manufactured by Ebara Corporation
Disk: 3M A188 (# 60)
・ Number of rotations: (plate) 70 rpm, (top ring) 71 rpm
Polishing pressure: 3.5 psi
-Abrasive: Made by Cabot, part number: SS25 (Use a mixed solution of SS25 stock solution: pure water = 1: 1)
・ Abrasive temperature: 20 ° C
・ Abrasive discharge amount: 200 ml / min
Workpiece (object to be polished): Substrate formed by PE-CVD to have a thickness of 1 μm of insulating film of tetraethoxysilane on a 12-inch diameter silicon wafer. Initial temperature of polishing is from 20 ° C to pad surface during polishing The temperature rises to 40-50 ° C.

(Analytical conditions of tetramer)
・ Use analyzer: Gel Permeation Chromatography L-7200 (Hitachi)
-Column: Two hpap KB-802.5 (exclusion limit 10000) in series-Mobile phase: DMF
・ Flow rate: 0.4 mL / min
-Oven: 60 ° C
・ Detector: RI 60 ° C
Sample volume: 90 μL

The above results are shown in Table 1.

  As shown in Table 1, the surface of the polishing pad of the present invention is softened during the polishing operation using the slurry by setting the D hardness and storage elastic modulus in a wet condition at 40 ° C. in a specific range, It was found that this softening greatly contributes to the polishing performance (the reduction of the incidence of scratches and the improvement of the polishing rate).

Claims (5)

  1. A polishing pad having a polishing layer made of polyurethane resin, comprising:
    The polishing layer is formed by curing a polyurethane resin curable composition including a polyisocyanate compound, a polyol compound, a curing agent, and micro hollow spheres.
    Following formula:
    {(D hardness at 20 ° C. of the polishing layer in a dry state) - (D hardness of 40 ° C. abrasive layer warm water saturation swelling of)} / (D hardness at 20 ° C. of the polishing layer in the dry state)
    The value of is 0.1 to 0.3,
    Following formula:
    {(Storage modulus of dry polishing layer at 40 ° C. ) − (Storage modulus of polishing layer saturated swollen with warm water of 40 ° C.)} / (Storage modulus of dry polishing layer at 40 ° C. ) )
    The value of is 0.4 to 0.9 ,
    A polishing pad characterized by
  2.   The polishing pad according to claim 1, wherein the polyisocyanate compound and the polyol compound comprise a prepolymer prepared by the reaction of the polyisocyanate compound and the polyol compound.
  3. The curing agent has a total amount of curing agent of 100% by weight and the following formula:
    The polishing pad in any one of Claims 1-2 containing 3-8 weight% of tetramers represented by these.
  4. A method of polishing a surface of an optical material or a semiconductor material, comprising using the polishing pad according to any one of claims 1 to 3 .
  5. A method for reducing scratches when polishing the surface of an optical material or a semiconductor material using the polishing pad according to any one of claims 1 to 3 .
JP2015076928A 2015-04-03 2015-04-03 Polishing pad Active JP6513455B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
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Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015076928A JP6513455B2 (en) 2015-04-03 2015-04-03 Polishing pad
TW105100600A TWI669360B (en) 2015-04-03 2016-01-08 Abrasive pad

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Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100770852B1 (en) * 2000-05-27 2007-10-26 롬 앤드 하스 일렉트로닉 머티리얼스 씨엠피 홀딩스 인코포레이티드 Grooved polishing pads for chemical mechanical planarization
JP5289787B2 (en) * 2007-02-01 2013-09-11 株式会社クラレ Polishing pad and polishing pad manufacturing method

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