Adhesion promoter

Abstract

Compositions useful for improving the adhesion of coating compositions, such as dielectric film-forming compositions, include a hydrolyzed poly(alkoxysilane). These compositions are useful in methods of improving the adhesion of coating compositions to a substrate.

Claims

1. A composition comprising: an oligomer chosen from polyarylene oligomers, poly(cyclic-olefin) oligomers, arylcyclobutene oligomers, vinyl aromatic oligomers, and mixtures thereof; a poly(alkoxysilane) hydrolyzed with ≦1 mole % of water; and a solvent; wherein the composition comprises ≦1 mole % of alcohol of hydrolysis and wherein the poly(alkoxysilane) has from 2 to 6 alkoxysilane moieties.

2. The composition of claim 1 wherein the poly(alkoxysilane) is hydrolyzed with ≦0.5 mole % of water.

3. The composition of claim 1 wherein the poly(alkoxysilne) prior to being hydrolyzed has the formula: ##STR00009## wherein each R is independently chosen from (C.sub.1-C.sub.6)alkylidene, (C.sub.1-C.sub.6)alkylene, (C.sub.6-C.sub.10)arylene, and (C.sub.2-C.sub.6)alkenylene; each R.sup.1 is independently chosen from H, (C.sub.1-C.sub.6)alkyl and (C.sub.1-C.sub.6)acyl; each Z is independently chosen from (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl and —OR.sup.1; X═(C.sub.6-C.sub.10)arylene, N(Y) or a covalent bond; Y═H, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylene-N(Y.sup.1).sub.2, (C.sub.2-C.sub.6)alkenyl, (C.sub.1-C.sub.6)alkylene-Si(Z).sub.2(OR.sup.1), or aryl(meth)acryloyl; and Y.sup.1═H, (C.sub.1-C.sub.6)alkyl, or (C.sub.2-C.sub.6)alkenyl; wherein each R is optionally substituted with one or more of (C.sub.1-C.sub.6)alkylidene-Si(Z).sub.2(OR.sup.1) and (C.sub.1-C.sub.6)alkylene-Si(Z).sub.2(OR.sup.1).

4. The composition of claim 1 wherein the arylcyclobutane oligomer has the formula: ##STR00010## wherein B is a n-valent linking group; Ar is a polyvalent aryl group and the carbon atoms of the cyclobutene ring are bonded to adjacent carbon atoms on the same aromatic ring of Ar; m is an integer of 1 or more; n is an integer of 1 or more; and R.sup.5 is a monovalent group.

5. The composition of claim 1 having a mean particle size of ≦1 nm as determined by dynamic light scattering.

6. The composition of claim 1 wherein the oligomer is an arylcyclobutene oligomer.

7. A process for manufacturing a device, comprising: providing a device substrate having a surface to be coated; disposing a coating of the composition comprising: an oligomer chosen from polyarylene oligomers, poly(cyclic-olefin) oligomers, arylcyclobutene oligomers, vinyl aromatic oligomers, and mixtures thereof; a poly(alkoxysilane) hydrolyzed with ≦1 mole % of water; and a solvent; wherein the composition comprises ≦1 mole % of alcohol of hydrolysis and wherein the poly(alkoxysilane) has from 2 to 6 alkoxysilane moieties on the substrate surface; and curing the coating.

8. The process of claim 7 wherein the device substrate is an electronic device substrate.

9. The process of claim 8 wherein the electronic device substrate comprises a surface comprising one or more of silicon, glass, ceramic, and metal.

10. The process of claim 7 wherein the poly(alkoxysilane) prior to being hydrolyzed has the formula: ##STR00011## wherein each R is independently chosen from (C.sub.1-C.sub.6)alkylidene, (C.sub.1-C.sub.6)alkylene, (C.sub.6-C.sub.10)arylene, and (C.sub.2-C.sub.6)alkenylene; each R.sup.1 is independently chosen from H, (C.sub.1-C.sub.6)alkyl and (C.sub.1-C.sub.6)acyl; each Z is independently chosen from (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl and —OR.sup.1; X═(C.sub.6-C.sub.10)arylene, O, S, S—S, S—S—S, S—S—S—S, N(Y), P(Y), or a covalent bond; Y═H, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylene-N(Y.sup.1).sub.2, (C.sub.2-C.sub.6)alkenyl, (C.sub.1-C.sub.6)alkylene-Si(Z).sub.2(OR.sup.1), or aryl(meth)acryloyl; and Y.sup.1═H, (C.sub.1-C.sub.6)alkyl, or (C.sub.2-C.sub.6)alkenyl; wherein each R is optionally substituted with one or more of (C.sub.1-C.sub.6)alkylidene-Si(Z).sub.2(OR.sup.1) and (C.sub.1-C.sub.6)alkylene-Si(Z).sub.2(OR.sup.1).

11. The process of claim 7 wherein the oligomer is an arylcyclobutene oligomer.

12. The process of claim 11 wherein the arylcyclobutane oligomer has the formula: ##STR00012## wherein B is a n-valent linking group; Ar is a polyvalent aryl group and the carbon atoms of the cyclobutene ring are bonded to adjacent carbon atoms on the same aromatic ring of Ar; m is an integer of 1 or more; n is an integer of 1 or more; and R.sup.5 is a monovalent group.

13. The process of claim 7 wherein the adhesion promoting composition has a mean particle size of ≦1 nm, as determined by dynamic light scattering.

Description

EXAMPLE 1

(1) Bis[3-(trimethoxysilyl)propyl]amine (0.41 g), of [3-(2-aminoethylamino)propyl]-trimethoxysilane (0.21 g), and 99.38 g of 4-methyl-2-pentanol containing 400 ppm water were combined in a 200 mL bottle. The mixture was stirred with a magnetic stirrer at ambient temperature (23° C.) in order to effect hydrolysis. Hydrolysis proceeded such that a single phase solution is produced in 15 minutes.

COMPARATIVE EXAMPLE 1

(2) Vinyltrimethoxysilane (0.3 g) and 99.7 g of 1-methoxy-2-propanol containing 800 ppm water were combined in a 200 ml bottle. The mixture was stirred using a magnetic stirrer at ambient temperature (23° C.) in order to effect hydrolysis. Hydrolysis proceeded such that a single phase solution was produced in 15 minutes.

COMPARATIVE EXAMPLE 2

(3) 3-Aminopropyltriethoxylsilane (0.1 g) and 99.9 g of 1-Methoxy-2-propanol containing 800 ppm water were combined in a 200 mL bottle. The mixture is stirred magnetically at ambient temperature (23° C.) in order to effect hydrolysis. Hydrolysis proceeded such that a single phase solution was produced in 15 minutes.

COMPARATIVE EXAMPLE 3

(4) [3-(2-Aminoethylamino)propyl]trimethoxysilane (0.6 g) and 99.4 g of 1-methoxy-2-propanol containing 800 ppm water were combined in a 200 mL bottle. The mixture was stirred using a magnetic stirrer at ambient temperature (23° C.) in order to effect hydrolysis. Hydrolysis proceeded such that a single phase solution was produced in 15 minutes.

EXAMPLE 2

(5) Bis[3-(trimethoxysilyl)propyl]amine (0.6 g), and 99.4 g of 4-methyl-2-pentanol containing 400 ppm waterwere combined in a 200 mL bottle. The mixture was stirred using a magnetic stirrer at ambient temperature (23° C.) in order to effect hydrolysis. Hydrolysis proceeded such that a single phase solution was produced in 15 minutes.

EXAMPLE 3

(6) Bis[3-(triethoxysilyl)propyl]amine (0.5 g) and 99.5% of 4-methyl-2-pentanol containing 400 ppm water were combined in a 200 mL bottle. The mixture was stirred using a magnetic stirrer at ambient temperature (23° C.) in order to effect hydrolysis. Hydrolysis proceeded such that a single phase solution was produced in 15 minutes.

EXAMPLE 4

(7) Bis[3-(triethoxysilyl)propyl]amine (0.5 g) and 99.5% of 1-methoxy-2-propanol containing 800 ppm water were combined in a 200 mL bottle. The mixture was stirred using a magnetic stirrer at ambient temperature (23° C.) in order to effect hydrolysis. Hydrolysis proceeded such that a single phase solution was produced in 15 minutes.

EXAMPLE 5

(8) Benzocyclobutene bis(3-(triethoxylsilyl)propyl)acrylamide (0.5 g) and 99.5 g of 1-methoxy-2-propanol containing 500 ppm water were combined in a 200 mL bottle. The mixture was stirred using a magnetic stirrer at ambient temperature (23° C.) in order to effect hydrolysis. Hydrolysis proceeded such that a single phase solution was produced in 15 minutes.

EXAMPLE 6

(9) N.sup.1,N.sup.1-Bis(3-(trimethoxysilyl)propyl)ethane-1,2-diamine (0.5 g) is combined with 2-methyl-1-butanol containing 350 ppm water in a 200 mL bottle. The mixture is stirred at ambient temperature (23° C.) in order to effect hydrolysis.

EXAMPLE 7

(10) To a 200 mL bottle are combined 4 methyl-2-pentanol containing 250 ppm water and 3-(trimethoxysilyl)-N-(2-(trimethyoxysilyl)ethyl)-N-(3-(trimethoxysilyl)propyl)propan-1-amine. The mixture is stirred at ambient temperature (23° C.) in order to effect hydrolysis.

EXAMPLE 8

(11) To a 200 mL bottle are combined 4 methyl-2-pentanol containing 400 ppm water and bis(3,3,9,9-tetramethoxy-2,10-dioxa-3,9-disilaundecan-6-yl)amine. The mixture is stirred at ambient temperature (23° C.) in order to effect hydrolysis.

EXAMPLE 9

(12) The adhesion promoting compositions from Examples 1-5 and Comparative Examples 1-3 were evaluated using a lithographic printing adhesion test. Each adhesion promoter composition was coated on a 200 mm test wafer using a Site Trac TT5-XP coater at a spin speed of 2000 rpm for 40 seconds followed by a 90° C. bake for 90 seconds to ensure solvent removal. An oligomer composition comprising 40% of an aqueous developable benzocyclobutene oligomer, which is a copolymer of DVS-bisBCB and benzocyclobutene acrylic acid having a molecular weight of approximately 5000, in a mixture of PROGLYDE™ DMM, PGMEA and anisole and containing a trifunctional diazonapthoquinone photoactive compound (CYCLOTENE™ P6505, available from The Dow Chemical Company, Midland, Mich.) was coated on top of the adhesion promoter layer using a Site Trace TT6-XP coater at a spin speed around 1500 rpm to target a film thickness of approximately 6.5 μm. The oligomer composition was nexted baked at 90° C. for 90 seconds to ensure solvent removal. Next, each oligomer-coated wafer was exposed on an ASML 200 i-line stepper using a bright field reticle to print rows of variously sized posts (from 1 to 25 μm) on the wafer. After exposure, a 15 minute post exposure hold was utilized to allow moisture diffusion back into the film. Next, the exposed areas of the oligomer resin were developed on a Site Trac TTP-X5 tool using a CD-26 developer solution employing a 60 second single puddle followed by a 90 second de-ionized water rinse. The post pattern remaining on the wafer was evaluated under an optical microscope. A sample was considered to pass the lithographic adhesion test when the minimum feature size of the remaining posts after development was less than or equal to 5 μm. The data are reported in Table 1 below.

EXAMPLE 10

(13) Dynamic light scattering measurements were carried out using a Malvern Zetasizer Nano ZS instrument. A sample of an adhesion promoter solution (1.5 mL) was transferred to a quartz cuvette, and then the cuvette was inserted in the sample holder of the Zetasizer instrument. The instrument software was set up for size measurement, and 15 to 24 scans were normally required to obtain an accurate particle size distribution for each sample. The mean particle sizes determined for Examples 1-5 and Comparative Examples 1-3 are reported in Table 1 below. Each of the adhesion promoters of the invention had only a single peak (unimodal distribution) with a mean particle size of <1 nm. Each of the comparative examples had at least one peak with a mean particle size >1 nm. Comparative Example 1 had 2 peaks (bimodal distribution), with one distribution having a mean particle size of >10 nm. Such large mean particle sizes in the comparative examples indicates the formation of larger nanoparticles due to the larger amount of silane hydrolysis, as compared to the poly(alkoxysilanes) of the invention.

(14) TABLE-US-00001 TABLE 1 Lithographic Printing Adhesion to Adhesion Test - Post Mean Particle Size Formulation silicon Size Remaining (μm) (nm) Comparative Poor No posts remaining <1, >10 Example 1 bimodal Comparative Poor No posts remaining 3-5 Example 2 Comparative Poor 15  >1 Example 3 Example 1 Good 3 <1 Example 2 Good 3 <1 Example 3 Good 2 <1 Example 4 Good 2 <1 Example 5 Good 2 <1

EXAMPLE 11

(15) The adhesion promoting compositions from Examples 1-5 and Comparative Examples 1-3 were evaluated according to the Cross-Hatch/Tape Peel test (ASTM D 3359) using a PA-2000 kit from Gardco. The cross hatch was applied and excess debris removed using a steady stream of compressed dry air prior to tape peel. After tape peel, the adhesion was evaluated and each of the adhesion promoting compositions from Examples 1-5 and Comparative Examples 1-3 were found to pass with 0% removed.

EXAMPLE 12

(16) A temporary bonding coating composition was prepared by combining 83.63 g of 68.5% DVS-bisBCB oligomer (having an average molecular weight of 25,000-30,000) in Proglyde™ DMM solvent was added 8.78 g of poly(tetramethylene glycol) having a molecular weight of 2900, (available as PolyTHF 2900, from BASF), 4.17 g of BAC-45 (a diacrylate terminated butadiene rubber having a molecular weight of 3000), 0.68 g of dicumyl peroxide, 0.49 g of a commercial antioxidant, and 2.25 g of Proglyde™ DMM solvent. The composition was manually mixed with a wooden stick, heated to 50° C. for approximately 1 hour, and then rolled until homogeneous.

(17) 200 mm silicon wafers were subjected to an oxygen plasma etch for 10 seconds. Next, 2 mL of the adhesion promoter from Example 4 was spin coated on the attachment surface of a carrier wafer (2000 rpm, 30 seconds), followed by a soft bake at 120° C. for 90 seconds, followed by cooling. The temporary bonding coating composition was spin coated (2000 rpm) on a device wafer, soft baked at 120° C. for 90 seconds, cooled for 30 seconds, and soft baked at 160° C. for 120 seconds to form a layer of a temporary bonding composition on the device wafer. The carrier wafer was then vacuum laminated to the temporary bonding coating composition at 80° C. for 60 seconds, with vacuum applied for 45 seconds and pressure applied for 60 seconds. The laminated wafers were then cured by heating on a hot plate, device side down, for 120 seconds at 210° C., in a nitrogen atmosphere. The thickness of the cured temporary bonding layer was approximately 25 μm. Following curing, the wafers were successfully debonded with a razor blade inserted near a notch and guided around the wafer, with the device wafer separating from the temporary bonding composition. The temporary bonding composition remained adhered to the adhesion promoted attachment surface of the carrier wafer.

EXAMPLE 13

(18) The procedure of Example 12 was repeated except that the temporary bonding coating composition also contained 41.82 g of a 90/10 styrene:diallyl maleate oligomer. The coating composition contained DVS-bisBCB oligomer and styrene:diallyl maleate oligomer in a weight ratio of 1:1. The thickness of the cured temporary bonding layer from this composition was approximately 26 μm. Following curing, the wafers were successfully debonded with a razor blade inserted near a notch and guided around the wafer, with the device wafer separating from the temporary bonding composition. The temporary bonding composition remained adhered to the adhesion promoted attachment surface of the carrier wafer.

EXAMPLE 14

(19) The procedure of Example 12 was repeated except that the DVS-bisBCB oligomer was replaced with 83.63 g of a 90/10 styrene:diallyl maleate oligomer in Proglyde™ DMM solvent (68.5% solids). This coating composition contained no DVS-bisBCB oligomer. The thickness of the cured temporary bonding layer from this composition was approximately 36 μm. Following curing, the wafers were successfully debonded with a razor blade inserted near a notch and guided around the wafer, with the device wafer separating from the temporary bonding composition. The temporary bonding composition remained adhered to the adhesion promoted attachment surface of the carrier wafer.