CN105922126A - Detection window for CMP (chemical mechanical polishing) pad and preparation method of detection window - Google Patents
Detection window for CMP (chemical mechanical polishing) pad and preparation method of detection window Download PDFInfo
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- CN105922126A CN105922126A CN201610390615.9A CN201610390615A CN105922126A CN 105922126 A CN105922126 A CN 105922126A CN 201610390615 A CN201610390615 A CN 201610390615A CN 105922126 A CN105922126 A CN 105922126A
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- Prior art keywords
- detection window
- raw material
- mechanical polishing
- chemical mechanical
- preparation
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
- B24B37/00—Lapping machines or devices; Accessories
- B24B37/11—Lapping tools
- B24B37/20—Lapping pads for working plane surfaces
- B24B37/205—Lapping pads for working plane surfaces provided with a window for inspecting the surface of the work being lapped
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Mechanical Treatment Of Semiconductor (AREA)
- Finish Polishing, Edge Sharpening, And Grinding By Specific Grinding Devices (AREA)
Abstract
The invention relates to a detection window for a CMP (chemical mechanical polishing) pad and a preparation method of the detection window. According to the technical scheme, an isocyanate-terminated prepolymer and a curing agent are evenly mixed and cured, and the CMP pad is prepared, wherein the isocyanate-terminated prepolymer is prepared from three following raw materials through mixing reactions: a raw material A is isocyanate with an isocyanate radical not directly connected with a benzene ring, a raw material B is polyol with the molecular weight being 500-1,500, a raw material C is a difunctional thiol compound, and the raw material C accounts for 1wt%-99wt% while the raw material B and the raw material C amount to 100wt%. The technology is simple, the production cost is low, and the prepared detection window is good in light transmission, stable in performance and long in service life.
Description
Technical field
The present invention relates to CMP art, the inspection of a kind of chemical mechanical polishing pads
Survey window and preparation method thereof.
Background technology
In the manufacture of integrated circuit and other electronic device, need on the surface of semiconductor wafer
Deposit or remove multiple conduction, semiconductive and dielectric material layer from it.Can be by such as thing
Physical vapor deposition (PVD), chemical gaseous phase deposition (CVD), plasma reinforced chemical vapour deposition
(PECVD), and electrochemistry is electroplated many deposition techniques such as (ECP) and is deposited conduction, semiconductive,
Thin layer with dielectric substance.
When being sequentially depositing or remove material layer, the uppermost top layer of wafer can become uneven.
Owing to semiconductor machining (such as metal lining) subsequently requires that this wafer has smooth surface, because of
This needs wafer is carried out planarization process, removes unwanted surface topography and surface defect,
Such as rough surface, the material of reunion, lattice damage, cut, and contaminated layer or material
Material.
Chemical-mechanical planarization, or chemically mechanical polishing (CMP) be for substrate such as quasiconductor
Wafer carries out the common technique planarized.In traditional CMP, wafer is placed in bracket group
The position contacted with the polishing pad in CMP instrument it is placed on part.This carriage assembly can be to crystalline substance
Sheet provides controlled pressure, thus is pressed against on polishing pad.Can be made by external motivating force
This pad moves (such as rotating) relative to wafer.Meanwhile, carry between wafer and polishing pad
For polishing medium.Thus, by polishing pad surface and the chemistry of polishing medium and mechanism
Wafer surface is polished and makes it smooth.
A difficult point in chemically mechanical polishing wafer is to measure when substrate is polished to anticipation
Degree.Therefore, polishing end point in situ detection method is developed.This optical polish terminal inspection in situ
Survey method can be divided into two fundamental types: 1) monitoring is with the optical signal of single wavelength reflection, such as the U.S.
Patent 5433651, or 2) monitoring is from the optical signal of multiple wavelength reflection, such as United States Patent (USP)
6106662.In order to the optical end point technology with these matches, have been developed for band window
Chemical mechanical polishing pads.Such as United States Patent (USP) 5605760, disclose a kind of polishing pad, Qi Zhongzhi
A few part is transparent for the laser of certain limit wavelength.Discloseder enforcement
In mode, transparent detection window embeds in opaque bearing sheet, and these forms can be to embed to be molded onto throwing
In light pad (that is, integral window), it is also possible to be loaded into after molding in the otch of polishing pad (i.e.,
Insert window).Regrettably, traditional polymer base endpoint detection window is exposed in visible ray logical
Often can have less desirable degraded and a variable color, and in use, due to dresser or slurry
The fricative abrasion of liquid is fuzzy and affects the judgement of terminal.
Summary of the invention
The invention aims to solve above-mentioned technical problem, it is provided that a kind of light transmission is good, resistance to
Wait property and wearability is good, the detection window of the chemical mechanical polishing pads of length in service life.
The present invention also provides for the inspection of the chemical mechanical polishing pads that a kind of technique is simple, production cost is low
Survey window preparation method.
The preparation method of the detection window of chemical mechanical polishing pads of the present invention is will to seal with isocyano
End prepolymer mix homogeneously with firming agent solidification form, wherein, described with isocyano end-blocking
Prepolymer formed by following three kinds of raw material hybrid reactions, raw material A be isocyano not with phenyl ring
The isocyanates being joined directly together；Raw material B be molecular weight be the polyhydric alcohol of 500-1000；Raw material
C is bifunctionality mercaptan compound, and wherein raw material B and C adds up to 100wt% meter, and raw material C accounts for
1-99wt%.
Solidification of being mixed homogeneously with firming agent by the prepolymer blocked with isocyano forms, wherein,
The prepolymer of described isocyano end-blocking is formed by following three kinds of raw material hybrid reactions: A) isocyanide
The isocyanates that acid group is not joined directly together with phenyl ring；B) molecular weight is the polyhydric alcohol of 500-1500；
C) bifunctionality mercaptan compound, wherein, raw material B and C adds up to 100wt% meter, raw material C
Account for 1-99wt%.
Described raw material C accounts for 9-99wt%.
After controlling reaction, in the prepolymer of described isocyano end-blocking, the content of NCO is
2-15wt%.
The isocyanates that described isocyano is not joined directly together with phenyl ring is that phenylenedimethylidyne two is different
Cyanate (XDI).
Described bifunctionality mercaptan compound has following general structure: HS-[R]-SH, its
Middle R be in saturated hydrocarbon chains, unsaturated hydrocarbon chain, substituted or unsubstituted aromatic group extremely
Few one.
Described firming agent for for 4,4 '-methylene-bis--(2-chloroaniline) (MOCA), control
Content 5-36wt%.
The detection window of chemical mechanical polishing pads of the present invention, is prepared by above-mentioned preparation method.
Described detection window has under the wavelength of 635 nanometers >=light transmittance of 90%.
For problem present in background technology, inventor is to the detection window on existing polishing pad
Raw material improves, and the particularly raw material of the prepolymer of isocyano end-blocking is improved: 1)
Raw material A uses the isocyanates that isocyano is not joined directly together with phenyl ring, mainly prevents isocyanide
The appearance of acid esters group and phenyl ring covibration, makes material good light stability, and non yellowing is described
The addition of raw material A rationally can be adjusted according to NCO content in the prepolymer of isocyano end-blocking
Whole, with control in prepolymer the content of NCO as 2-15wt% preferably；Concrete isocyano is not
The isocyanates being joined directly together with phenyl ring can list XDI
(XDI), benzene two (1,2-ethylidene) diisocyanate, benzene diisopropyl diisocyanate etc..
2) raw material C have selected especially never detection window manufacture in used bifunctionality Thiolation
Compound, this compounds has the advantages that reaction rate is slow, is used for reacting generation isocyano envelope
During the prepolymer held, it is possible to control extent of reaction, the compound of generating structure stable uniform, from
And it is uniform to control strong mechanical property；Further, bifunctionality mercaptan compound also has control light
The technique effect of refractive index, it is ensured that material is to the adaptability of various light and stability.With raw material B
Adding up to 100wt% meter with C, raw material C accounts for 1-99wt%, is more highly preferred to 9-99wt%, too much can
Cause that the response time is long and energy consumption increases, cross that I haven't seen you for ages and lower the transmitance of light；Described double
Degree of functionality mercaptan compound preferably has following general structure: HS-[R]-SH, wherein R
For saturated hydrocarbon chains such as-[CH2]n-, n=(1-150)；Unsaturated hydrocarbon chain is such as
-[CH=CH]n-, n=(1-50) ,-[C (CH3)=CH]n-, n=(1-30) ,-[C (CH3)=C
(CH3)]n-, n=(1-20) etc.；Substituted or unsubstituted aromatic group such as-[C6H4]-,(C6H4
Disubstituted for phenyl ring) at least one.Being more highly preferred to R is saturated hydrocarbon chains, as
-[CH2]n-, n=(50-80), this compound can pass through with vinyl monomer and two mercaptan as raw material
Addition polymerization methods is prepared from；Described firming agent is preferably 4,4 '-methylene-bis--(2-
Chloroaniline), control 5-36wt%, too low meeting causes material to be difficult to molding, too high, can cause
Material stiffness is excessive, and complexion changed is bigger.
Beneficial effect:
Present invention process is simple, production cost is low, prepares prepolymer former of isocyano end-blocking
Material adds bifunctionality mercaptan compound, coordinate firming agent can obtain light transmission good,
There is >=the excellent light transmittance of 90%, weatherability and wearability is good, make under the wavelength of 635 nanometers
With the detection window of life-span length, described detection window, when chemical mechanical polishing pads, has good saturating
Photosensitiveness, is difficult to be worn, acid and alkali-resistance environment, service life length, be highly suitable for polishing end point
In situ detection method.
Detailed description of the invention
The term " polishing medium " used in this specification covers the polishing fluid containing granule and not
Polishing fluid containing granule.
About there is the term " light transmittance " of high transmission rate detection window by following public affairs in this specification
Formula defines:
Laser power during laser power during light transmittance=put into detection window/do not put into detection window
Use instrument is 635nm, the laser power meter of power 20mW.
Embodiment 1
25.85g XDI (XDI) is put in there-necked flask,
Rising high reaction temperature in 30 minutes to 75 DEG C, start agitator, mixing speed is 300 turns/
Minute.By PTMEG (polytetramethylene ether diol) that 90g molecular weight is 1000 and 10g
Mercaptan compound HS-[CH2]n-SH, the mixture of (n=50-80, molecular weight 1000-1200) drips
Being added in XDI, time for adding controlled at 0.5 hour.After dropping, continue dropping and exist
Insulation reaction 2 hours under the conditions of 80 DEG C, then will carry out deaeration process to reactant, control de-
The vacuum of bubble is-0.096MPa, 80 DEG C, 30 minutes, obtains prepolymer 1, NCO%=
2.5wt%.
Same method can obtain prepolymer embodiment 2-8.(being shown in Table one)
Table one
| Numbering | XDI(g) | PTMEG, g | Mercaptan compound C (g) | NCO%, Wt% |
| Embodiment 1 | 25.85 | 90 | 10 | 2.5 |
| Embodiment 2 | 32.9 | 50 | 50 | 4.7 |
| Embodiment 3 | 39.95 | 10 | 90 | 6.7 |
| Embodiment 4 | 47 | 5 | 95 | 8.5 |
| Embodiment 5 | 54.05 | 1 | 99 | 10.2 |
| Embodiment 6 | 61.1 | 91 | 9 | 11.7 |
| Embodiment 7 | 68.15 | 95 | 5 | 13.1 |
| Embodiment 8 | 75.2 | 99 | 1 | 14.3 |
The preparation method of high transmission rate detection window
Embodiment 9
Weigh the prepolymer in 100g embodiment 1 and 6.36g MOCA (4,4 '-methylene-bis--(2-chlorine
Aniline)), put in beaker and be warmed up to 110 DEG C, after MOCA melts and start stirring so that it is mixing is all
Even, final mixture is poured in mould, and is placed in together in curing oven with mould,
90 DEG C keep 16 hours, were then down to room temperature, the demoulding in 0.5 hour, obtain high printing opacity
Rate detection window embodiment 9.
Transmitance detects: output the diameter hole not less than 5cm in rigid planar, in hole
Top place one piece of microscope slide, then by 635nm, the light source of the laser power meter of 20mW is sent out
Emitter is placed in below hole at 10cm, is placed in below hole by power receiver.
Light source emitter is opened, reads laser power when not putting into high transmission rate detection window
W0, then detects high transmission rate window embodiment 9 and is put on microscope slide, reads and puts into high printing opacity
Laser power W1 during rate detection window, (W1/W0, with percent then to calculate light transmittance TI
Represent) 95.2%.
Detection window in embodiment is installed to IC1000 detection window position and is polished machine test,
Use the polishing slurries of Celexis CX2000, use Diagrid AD3BG-150855 to repair
Whole dish, carries out diamond conditioning 5 hours by conditioning technique in situ to polishing pad, then will inspection
Survey window takes off, and cleans, dries, be put on microscope slide, reads laser power W2, then counts
Calculate light transmittance T2 (W2/W0 is expressed as a percentage) 90.8%.
Use same method to prepare high transmission rate detection window embodiment 10-16, and detect meter
Calculate TI and T2 transmitance (being shown in Table two).
Table two
| Numbering | Prepolymer, 100g | MOCA, g | TI, % | T2, % |
| Embodiment 9 | Embodiment 1 | 6.36 | 95.2 | 90.8 |
| Embodiment 10 | Embodiment 2 | 12.8 | 96.7 | 91.6 |
| Embodiment 11 | Embodiment 3 | 19.3 | 97.2 | 92.8 |
| Embodiment 12 | Embodiment 4 | 25.8 | 97.8 | 93.3 |
| Embodiment 13 | Embodiment 5 | 32.4 | 98.1 | 95.7 |
| Embodiment 14 | Embodiment 6 | 39.1 | 94.2 | 92.1 |
| Embodiment 15 | Embodiment 7 | 47.9 | 68.3 | 65.4 |
| Embodiment 16 | Embodiment 8 | 54.8 | 46.6 | 43.5 |
| Comparative example 1 | 42 | 38 |
Remarks: comparative example is the detection window of the Tao Shi polishing pad IC1000 of main flow on market.
As can be seen from the table, in the present invention detection window have under the wavelength of 635 nanometers >=
The light transmittance of 90%, will be far longer than current main product.This is mainly possibly due to Thiolation
Compound introduces, and reduces W-response speed, decreases the rate of release of heat in reaction, from
And reduce rearrangement and the crystallization of macromolecular chain in polyreaction, add the light transmission of material.
Claims (9)
1. the preparation method of the detection window of a chemical mechanical polishing pads, it is characterised in that will
Isocyano end-blocking prepolymer mix homogeneously with firming agent solidify form, wherein, described different
The prepolymer of cyanate radical end-blocking is formed by following three kinds of raw material hybrid reactions, and raw material A is isocyanide
The isocyanates that acid group is not joined directly together with phenyl ring；Raw material B be molecular weight be 500-1500
Polyhydric alcohol；Raw material C is bifunctionality mercaptan compound, and wherein raw material B and C adds up to
100wt% counts, and raw material C accounts for 1-99wt%.
2. the preparation method of the detection window of chemical mechanical polishing pads as claimed in claim 1,
It is characterized in that, described raw material C accounts for 9-99wt%.
3. the preparation method of the detection window of chemical mechanical polishing pads as claimed in claim 1,
It is characterized in that, the content of NCO in the prepolymer that after controlling reaction, described isocyano blocks
For 2-15wt%.
4. the system of the detection window of the chemical mechanical polishing pads as described in any one of claim 1-3
Preparation Method, it is characterised in that the isocyanates that described isocyano is not joined directly together with phenyl ring
For XDI.
5. the system of the detection window of the chemical mechanical polishing pads as described in any one of claim 1-3
Preparation Method, it is characterised in that described bifunctionality mercaptan compound has a following general structure:
HS-[R]-SH, wherein R is saturated hydrocarbon chains, unsaturated hydrocarbon chain, replacement or unsubstituted
Aromatic group at least one.
6. the preparation side of the detection window of the chemical mechanical polishing pads as described in claim 1-3
Method, it is characterised in that described firming agent is 4,4 '-methylene-bis--(2-chloroaniline).
7. the preparation method of the detection window of chemical mechanical polishing pads as claimed in claim 6,
It is characterized in that, control curing agent content 5-36wt%.
8. the detection window of a chemical mechanical polishing pads, it is characterised in that by claim
1-8 any one preparation method prepares.
9. the detection window of chemical mechanical polishing pads as claimed in claim 8, it is characterised in that
Described detection window has under the wavelength of 635 nanometers >=light transmittance of 90%.
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Cited By (5)
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| CN108047420A (en) * | 2017-11-28 | 2018-05-18 | 湖北鼎龙控股股份有限公司 | A kind of polyurethane polishing layer and preparation method thereof |
| CN108747870A (en) * | 2018-05-28 | 2018-11-06 | 湖北鼎龙控股股份有限公司 | The preparation method of polishing pad |
| US10207388B2 (en) | 2017-04-19 | 2019-02-19 | Rohm And Haas Electronic Materials Cmp Holdings, Inc. | Aliphatic polyurethane optical endpoint detection windows and CMP polishing pads containing them |
| US10465097B2 (en) | 2017-11-16 | 2019-11-05 | Rohm And Haas Electronic Materials Cmp Holdings, Inc. | Aliphatic UV cured polyurethane optical endpoint detection windows with high UV transparency for CMP polishing pads |
| CN113478382A (en) * | 2021-07-20 | 2021-10-08 | 湖北鼎汇微电子材料有限公司 | Detection window, chemical mechanical polishing pad and polishing system |
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| CN113478382A (en) * | 2021-07-20 | 2021-10-08 | 湖北鼎汇微电子材料有限公司 | Detection window, chemical mechanical polishing pad and polishing system |
| CN113478382B (en) * | 2021-07-20 | 2022-11-04 | 湖北鼎汇微电子材料有限公司 | Detection window, chemical mechanical polishing pad and polishing system |
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| CN105922126B (en) | 2018-05-11 |
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