JPH06505101A - Photodefinable intermediate level dielectric - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Photodefinable intermediate level dielectric The United States government granted this invention a U.S. Air Force Contract. Rights under P33615-89-C-5603.

prior art The present invention relates to materials used to isolate dielectric layers in microelectronic circuits. do. In particular, the present invention allows the formation of dielectric layers at desired locations within a multilayer structure. It relates to polymeric materials that can be photopolymerized as described above. This type of layer is They must be insulators with good chemical resistance and, of course, if they are It must be adhered to the substrate on which it will be placed.

Polyimides have superior heat and chemical resistance compared to many other polymers. Therefore, it is used for such dielectric materials. Literature disclosing the use of polyimides and a patent in U.S. Pat. No. 4,908,096 by one of the inventors of this invention. has been extensively studied. The drawbacks of polyimides are discussed, viz. , polyimides release large amounts of volatiles during curing, absorb moisture, and cause poor adhesion. and has a relatively high coefficient of expansion. This patent has improved properties with other polymers, namely dialdehydes and phenols, as intermediate level dielectrics. Discloses and claims the use of vinylbenzyl or alkyl ether condensation products. seek

The present invention applies to other polymers that have been found to form useful interlevel dielectrics. related.

In U.S. Pat. No. 4,824,920, one of the inventors of the present invention Vinyl benzyl ether is the reaction product of phenol and Thermoset resins are disclosed that have application in manufacturing laminated boards for engineering applications. US patent No. 4.816.498 describes the condensation of dialdehydes with 3 to 4 moles of phenol Other types of oligomer condensation products that differ from the resins in that they are It is shown. Such oligomers can also be esterified to vinylbenzyl and alkyl ether. These are laminated boards for electronics. Can be used for manufacturing. As you can see from the discussion below, such resins have intermediate levels. It has been found to be useful as a precursor for polymers for Bell dielectrics.

Summary of the invention The present invention provides electronic intermediate connections from a polymer on a substrate and a dielectric layer thus produced. It includes a method of forming a predetermined pattern that can be used in a structure.

Such patterns are created by applying a prepolymer onto a substrate and then forming a shielding pattern. The exposed areas are irradiated to render the prepolymer insoluble and then the non-irradiated shielded areas of the coating layer selectively dissolve the irradiated prepolymer, leaving the insoluble irradiated prepolymer produced by curing to form an infusible glassy solid in a predetermined pattern. will be built.

This prepolymer is the first of the two oligomers listed below, or Either a mixture of both mer. One is dicyclopentadiene and phenol. The reaction product is vinylbenzyl ether, which has the following formula: do: During the ceremony, R1, R2=H or alkyl having 1 to 10 carbon atoms: R4=H.

10 cycloalkyl moieties, or benzyl, provided that at least 5 of all A 0% is vinylbenzyl moiety; L=Br or C1: a=O11 or 2; b=o or 1; m5nSs and t are 0 or an integer, but m+n0s+t=z is an integer from 1 to 10 is; R, = H, alkyl moiety having 1 to 10 carbon atoms, halogen or alkoxy moiety, Or a monovalent aromatic radical. In a preferred embodiment, 70% of A is vinylbenzene. The remaining A is propyl.

The second oligomer comprises (a) 1 molar proportion of dialdehyde and (b) about 3 to about 4 phenols. ether of oligomeric condensation products with molar proportions; in this case dialdehyde is OHC(CHz)-CHO (in the formula, n = 0 or an integer from 1 to 6), cyclopenta dialdehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde Hyde, hexahydrophthaldehyde, cyclohebutanedialdehyde, hexahyde Droisophthalaldehyde, hexahydroterephthalaldehyde, and cycloo selected from the group consisting of cutandialdehyde; in this case the phenol is of structure R0 C, H, OH (wherein R1 is hydrogen or an alkyl group having 1 to about 10 carbon atoms) Has: The phenol residue of the oligomer condensation product is vinylbenzyl, carbon number Alkyl moiety having 1 to 10 carbon atoms, cycloalkyl moiety having 5 to 10 carbon atoms, and benzyl etherified by one or more substituents randomly selected from the group consisting of to form an ether moiety, in which case the ratio of vinylbenzyl to ground moieties is 1:1. From 621 to approximately 621.

In U.S. Pat. No. 4,824.920, one of the inventors of the present invention production and use of ethers and complexes of reaction products of ntadiene and phenol; In particular, their use in laminated boards for electronics is disclosed. These compositions was combined with the oligomers of U.S. Pat. No. 4,816,498 to provide an intermediate level of It has now been found that they can be used as electrical objects, in which case they have low water absorption. , low dielectric constant, low coefficient of thermal expansion, high glass transition temperature, high thermal stability, high solids content little or no coating concentration, photochemical curability, thermal curability and curing process It has the advantage of not generating volatile substances.

The prepolymer used for patterning has the following formula: R1, R2=H or alkyl having 1 to 10 carbon atoms; R4=H.

10 cycloalkyl moieties, or benzyl, provided that at least 5 of all A 0% is vinylbenzyl moiety; L=Br or C1; a=o, 1 or 2; b=o or 1; mSn, s and t are 0 or integers, but m+n+s+t=z is an integer from 1 to 10 is; R5=H1 alkyl moiety having 1 to 10 carbon atoms, halogen or alkoxy moiety, Or a monovalent aromatic radical.

The dicyclopentadiene moiety in either ring can be substituted. R1 and R2 is typically hydrogen, i.e., in the practice of this invention, unsubstituted dicyclopentadiene. R1 and R2 are each an alkyl group having up to about 10 carbon atoms, preferably or a primary alkyl group. When dicyclopentadiene is substituted In some cases, lower alkyl groups such as methyl, ethyl, propyl and butyl are used. Particularly preferred. Substitution possible at any position on the dicyclopentadiene ring system However, R1 exists on a carbon of a 5-membered ring that is not bonded to an aryl group, and R2 is a bicyclic ring. Preferably present at the bridge or bridge head carbon of the moiety. Yes. The phenol end of our resin and the phenol part of P or Q are methyl groups. or can be substituted by a halogen atom. with dicyclopentadiene It is also possible to use mixtures of such phenols for the condensation. Methyl group is acid Exists in a meta or para position relative to a position containing an elementary atom. To carry out the invention: Such mixtures, in which rose-substituted phenols are preferred, are an advantageous embodiment. re) and tend to give amorphous resins that are susceptible to photochemical curing. Ru.

This basic resin can be easily made flame retardant by introducing halogen atoms into the aromatic ring. It can also be modified. Thus, L can be a halogen atom, especially bromine. , when the aromatic ring is halogenated, a is 0.1 or 2, and b is 0 or 1. be. As flame retardants, polyhalogenated substances are preferred, which means that a and b are the most It means that it is desirable to be large. When the aromatic ring is not substituted with halogen , both a and b are 0.

Fragments P and Q are subunits of the adduct. This adduct is oligo This may be a head-to-head arrangement, a head-to-tail arrangement, or a fully or partially It is a random arrangement. When oligomers are formed, they are relatively It has a low molecular weight. The variables m, n, s and t are each integers, and 2 is m+n+s +t, 2 is an integer from 1 to 10, usually up to about 5, and the present invention Preferably, 2 is 3 or 4 for the specific implementation.

The phenolic hydroxyl in the adduct is capped so that it is converted to an ether. capped. At least 80% of the phenolic groups are thus capped. but preferably at least 90% capped, with the phenolic groups It is even more preferred that at least 95% of the In other words, In the above formula, less than about 20% of the A moiety is hydrogen and less than 10% is hydrogen. Preferably, less than 5% is hydrogen, even more preferably.

In the ether moiety, A is the vinylbenzyl moiety, that is, the following structure: [wherein the vinyl group is is meta or para to CHt and R6 is hydrogen], usually meta- The best L1 case occurs when it is a mixture of isomers and para-isomers. R 6 is hydrogen, an alkyl moiety having 1 to about 10 carbon atoms, halogen, an alkyl moiety having 1 to about 10 carbon atoms; lukoxy moiety, the parent is an aromatic hydrocarbon. is a chemically inert substituent selected from the group consisting of

However, all phenolic hydroxyls are end-capped by vinylbenzyl moieties. It is desirable that the dielectric constant of all other groups is lower than that of the lower dielectric constant. There is a definite cost benefit in the case of vinyl benzyl with the sacrifice. main departure In light, at least 50% of the A moieties that are different from hydrogen are vinylbenzyl moieties. However, if 70 to 100% of the ether groups are vinylbenzyl gives compounds with good performance properties, with 95-100% of such groups The best products are obtained when is vinylbenzyl. In many applications, Less than complete end-capping with nylbenzyl groups is accepted, but hydroxy All of the groups should be capped.

When less than all of the ether groups are vinylbenzyl, A has 1 to 10 carbon atoms. Resins having an alkyl group, a cycloalkyl group having 5 to 10 carbon atoms, or a benzyl group are preferred. Delicious. When A is an alkyl group, a primary alkyl group is preferable, especially if the number of carbon atoms is 1 to 4 primary lower alkyl groups are preferred. Therefore, the most preferred alkyl group is From thyl, ethyl, 1-propyl, 1-butyl, and 2-methyl-1-propyl Become. Other alkyl groups are 1-pentyl, 1-hexyl, 1-hebutyl, 1-octyl, Chyl, 1-nonyl, 1-decyl, 2-methyl-1-butyl, 3-methyl-1-butyl methyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-methyl Typical examples include tyl-1-pentyl. However, in the practice of this invention, benzyl It should be emphasized that radicals also work very well. The most used in the present invention Typical cycloalkyl groups are unsubstituted or alkyl containing 5 to 10 carbon atoms. Kyl-substituted 5- and 6-membered cycloalkanes. Examples are cyclopentyl, cyclo Hexyl, methylcyclopentyl, dimethylcyclopentyl, ethylcyclopene Chyl, propylcyclopentyl, butylcyclopentyl, pentylcyclopentyl , ethylmethylcyclopentyl, methylpropylcyclopentyl, butylmethylene cyclopentyl, methylcyclopentyl, dimethylcyclohexyl, ethylcyclopentyl Chlorhexyl, propylcyclohexyl, butylcyclohexyl, etc.

The l-propyl group is a particularly desirable replacement group for the vinylbenzyl moiety, with 5% of A less than 50% is hydrogen and the remainder is vinylbenzyl or A resin in which is 1-propyl is highly desirable. In a preferred embodiment, A is less than At least 70% is vinylbenzyl, and the remaining A is propyl.

The use of mixtures increases the solubility of the resin in the solution and promotes good film formation. forming a stable non-flaking coating Both tend to form desirable amorphous resins. Desired mix of resins The compound is z=1 resin about 5 to 20% by weight, z=2 resin about 10 to about 30% by weight, 2; 3 About 5 to about 30% by weight resin, z = 4 resin about 5 to about 30% and z = 5 to 10 resin about 5 ~30% mixture.

This accompanying vinyl group is removed by thermal, chemical or radiative means. It is easily crosslinked during the curing process. Heat curing is generally about 100 to about 300℃ It was carried out in the temperature range of 150 to 200 degrees Celsius, and in fact The post-curing at about 180-300°C was carried out for about 0.0000000000000000000000000000000000000000000000000000000. Implemented for 5 to 24 hours be done. Curing can be done with e.g. azo-bis-isobutyronitrile, benzoyl peroxide, peroxide, etc. Free radical initiators such as di-t-butyl oxide and the like may also be used.

Curing can be effected by visible or ultraviolet light, especially in the presence of suitable photoinitiators or sensitizers. The same can be done by irradiation. Perform either thermal, chemical or photochemical curing However, the resin is extensively crosslinked and cured into an infusible, insoluble, glassy solid. Become.

The resins of this invention are made by any convenient method known in the art. However, these Vinylbenzyl halide is dissolved in basic solution with dicyclopentadiene-phenol adduct. It is most easily produced by reacting in liquid. Generally, vinylbenzene Mixtures of meta and para isomers of luchloride are used; Yoshito can also be used, although to a lesser extent. This reaction often involves acetone, N - Alcoholic potassium hydroxide solution containing methylpyrrolidone or other organic co-solvents It is conveniently carried out in liquid at reflux temperature. Part of A is alkyl, cycloa alkyl or benzyl moieties, these are the appropriate alkyl, cycloalkyl, Reacting kill or pendyl halides with partially vinylbenzyl end-capped adducts or by reacting the uncapped adduct with the /% lido mixture. It can be manufactured by

The second oligomer contains 1 molar proportion of certain dialdehyde and about 3 to about 4 molar proportions of phenol. It is an ether of the oligomer condensation product with a le proportion. For more information, see Ether The moiety is a vinylbenzyl moiety, an alkyl moiety having 1 to 10 carbon atoms, and a vinylbenzyl moiety having 5 to 10 carbon atoms. randomly selected from the group consisting of cycloalkyl, and benzyl, in this case , the ratio of vinylbenzyl to ground ether moieties is at least 1:1, and about 6=1 It can be of a certain size.

The phenolic oligomer contains 1 molar proportion of the selected dialdehyde and 3 to 3 phenols. It is a condensation product with 4 molar proportions. In the practice of this invention, a proportion of more than 4 moles of Fe It is also possible to use alcohol, but in this case less than 4 moles react with the dialdehyde. One type of dialdehyde that can be used in the invention has the formula: OHC (CHz), CHO (in the formula , r=o or an integer from 1 to 6). this Dialdehydes such as glyoxal, malondialdehyde, and succinidial Dehyde, glutaraldehyde, adiphaldehyde ), pimelaldehyde, and sebacaldehyde. Al such that n is 0 to 4 Dehydes are particularly preferred, and glyoxal (n=0) is particularly preferred for the practice of the invention. preferable.

Other aldehydes that can be used to make oligomeric condensation products are cyclopentane dialdehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde hexahydrophthalaldehyde (i.e., the aromatic ring is reduced to form cyclohexyl Phthalaldehyde reduced counterpart of phthalaldehyde which became San ring), to cyclo Contains butane dialdehyde and cyclooctanedialdehyde.

The oligomer contains 1 mole of the above dialdehyde and 3 to about 4 moles of the above dialdehyde. It is a condensation product with Phenol has the general structure Ra　Cs　Ha　OH (in the formula , R6 is hydrogen or alkyl having 1 to about 8 carbon atoms). The most desirable frame Phenol is phenol itself, ie when R6 is hydrogen. R6 is Al When it is a kyl group, an alkyl group having 1 to about 4 carbon atoms is most preferred, and R6 is a methyl group. Cresol is another preferred species of phenol.

This condensation product is similar to the phenol-formaldehyde condensation product. Sunawa This product results from the condensation of two molar proportions of phenol with each aldehyde group.

To illustrate this reaction, a “monomer” using phenol and glyoxal is used. ``In the simplest case that can be considered a product, the product has the structure do: In the formula, hydroxyl is almost exclusive to the condensation point of phenol and glyoxal. Usually ortho and para, mostly para. However, the above product Glyoxal groups/molecules, any of which reacts with another mole of glyoxal This glyoxal is further condensed with another 3 moles of phenol, yields the following structure: The above oligomeric product results from the molar ratio of 7-phenol and 2-glyoxal. Ru. This oligomer can then be reacted with another mole of glyoxal, The latter is further reacted with other 3 phenols to form 10 phenolic groups to 3 glyoxers. Similarly, the following higher oligomers of the following structure with a molar ratio of The higher oligomer has a phenol to glyoxal molar ratio of 13:4 and has the following: The higher oligomer has a phenol to glyoxal molar ratio of 16:5; The limiting molar ratio is 3:1. Ratio less than 3:1 without internal rationalization What can never be obtained, i.e., at least two phenolic portions of the oligomer and the reaction It should be mentioned that 1 mol of glyoxal is required to meet this requirement.

Similarly, the "monomer" condensation product is a 4:1 phenol-glyoxal Has a limited ratio.

The condensation products, as mentioned above, are themselves phenols and oligomers. It is a mixture. We have from 4 to about 60 phenol moieties/molecule, more usually 4 Of interest are condensation products having ~22 phenol moieties/molecule. this product is a mixture of oligomers, with preferred mixtures containing on average about 5 to about 8 phenolic It is characterized by having a double moiety/molecule.

More specifically, dialdehyde is glyoxal and phenol is phenol. per se, each oligomeric product has a molecular weight of about 400 to 6000, and so on. It preferably has a molecular weight of about 400 to about 2,200. Mixing of oligomeric products The material has an average molecular weight of about 500 to about 800.

The intermediate level dielectric resin of the present invention is an ether of the oligomeric condensation products described above.

In one variant of the invention, phenol is added to make the final resin more flame retardant. The condensation product is halogenated prior to ether formation. Halogen is chlorine or smells The use of brominated products is preferred, as an increase in flame retardancy occurs especially when the brominated products are brominated. Halo The gene is introduced at the ortho and para positions to the phenolic hydroxyl group.

If all ortho and para positions are available, then Up to three halogen atoms can be introduced. Maximally halogenated oligo Although it is often preferred to produce mer condensation products, sometimes less than the maximum Gen content is advantageous. However, in the latter variant, per phenolic moiety It should become apparent that at least one chlorine or bromine atom is present.

converting substantially all (greater than about 99.5%) of the hydroxyls to ether moieties; The phenol condensation product is capped in order to Each of the ether parts is vinyl The ratio of all ether moieties of rubenzyl to earth is at least 1:1 and about 6=1 Regarding the first type oligomer that grows to a certain extent, as mentioned above, vinyl vinyl alkyl moiety having 1 to 10 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, and and benzyl.

Acid-catalyzed condensation of phenol and dialdehyde followed by phenolic hydride Substantial conversion of phenolic hydroxyl by converting roxyl to ether A prepolymer can be produced by all end-capping.

To avoid the formation of terminal hydroxyl methylene groups -CH,OH, the acid-catalyzed condensation preferably. For example, phenol condensation products can be ether by suitable means, such as by reaction in a basic medium with End-capping by formation can be performed.

The resulting mesolevel dielectric oligomers are concomitantly crosslinked by various curing means. Can be polymerized. If curing is carried out by thermal means, the oligomer Heat the sesame oil in air to a temperature of about 100 to 300 degrees Celsius, especially about 120 to 200 degrees Celsius. As a result, curing is generally self-initiated. For example, azo-bis-isobutyl Free radicals such as lonitrile, benzoyl peroxide, di-t-butyl peroxide, etc. It is also carried out using cal initiators. The presence of a particularly suitable photoinitiator or sensitizer for curing Start by irradiation with visible or ultraviolet light in the absence or presence of can be carried out to produce an infusible, insoluble glassy solid.

Photodefinable (photodef 1nable) usage of these oligomers as a passivation agent, as an interlevel dielectric, and as a deep dielectric isolation region in devices. (Insulator isolation trench) It can be used as a resist or the like. Most of the following are mid-level dielectrics However, from this description the skilled researcher will be able to use the substance of the present invention in other ways. You will also recognize how to use it for this purpose.

This oligomer is applied as a coating onto a suitable substrate. Group used The board is usually a silicon wafer-1 laminated circuit silicon chip, a printed circuit board or It is a ceramic substrate. Photosensitive oligomers are applied by spin coating or spray coating. by the use of a doctor's knife or by other methods commonly known in the art. Can be applied to obtain a uniform coating. If the viscosity is too high, use a suitable solution. A solution of the resin in a solution can be used. These oligomers are polar aprotic including solvents, aromatic hydrocarbons, halogenated hydrocarbons, ketones, esters, etc. Soluble in a wide variety of solvents. Examples of solvents that can be used in the practice of this invention are Dimethylformamide (DMF), hexamethylphosphoramide (HMPA) , N-methylacetamide (NMAc), dimethyl sulfoxide (DMSO), N-methylpyrrolidone (NMP), benzene, toluene, xylene, dichloro Methane, chloroform, carbon tetrachloride, chlorobenzene, tetrachloroethane, tetrachloride Trachlorethylene, trichloroethane, gamma-butyrolactone, methylethyl ketone, diethyl ketone, hexanone, heptanone, octanone, methyl acetate , ethyl acetate, methoxyethanol, ethoxyethanol, etc. This solvent It should be non-reactive with both the substrate and the photosensitive oligomer, and should not dissolve the resin. should be able to dissolve to form a solution of at least about 10% weight-volume. Ru.

Consistent with the above considerations, since this solvent is typically removed before further processing, It is also preferred to use a solvent with the lowest possible boiling point.

Since these oligomers are directly photopolymerized, it is not possible to use a photosensitizer or photoinitiator. A photosensitizer or photoinitiator is useful for shortening irradiation time. Photosensitizer When using a photoinitiator, the photosensitizer or photoinitiator is added to the oligomer during the coating process. from about 0.001 to about 5.0% by weight based on the oligomer. Exist in quantity. Examples of photosensitizers or photoinitiators that can be used continuously in the practice of the invention is, for example, benzophenone, 4.4°-bis(dimethylamino)benzopheno xanthone, acetophenone, 4-trifluoromethyl-acetophenone, Triphenylene, thioxanthone, anthraquinone, 4-phenylbenzopheno Naphthalene, 2-acetonaphthalene, 1-acetonaphthalene, chrysene, acetonaphthalene, anthracene, 9.10-dichloroanthracene, pyrene, triphenylene, 1- Fluoronaphthalene, 1-chloronaphthalene, 1-bromonaphthalene, 1-io Donaphthalene, 1,3-dicyanobenzene, dimethyl isophthalate, diethyl Inphthalate, methyl 3-cyano-benzoate, ethyl 3-cyanobenzoate phenyl 3-cyano-benzoate, 2,2-dimethoxyacetophenone , 2,2-jethoxyacetophenone, 2. 2’-dimethoxy-2-pheny Ruacetophenone, 2. 2'-jethoxy-2-phenylacetophenone, Benzoin methyl ether, and 1-phenyl-1,2-propanedione-2- Contains substances such as 0-benzoyloxime. The preferred sensitizer is benzophenone , 4゜4“-bis(dimethylamino)benzophenone, 1,3-dicyanoben Zen, dimethyl isophthalate, diethyl isophthalate, methyl 3-cyano- Includes benzoate and phenyl 3-cyano-benzoate.

If the photosensitive oligomer is applied to the substrate as a solution, the solvent used should be removed before irradiation. must be removed. Therefore, if a solvent is present, the Heating the coated substrate for a sufficient period of time to remove substantially all of the material before irradiation This is commonly known as a “soft bake”. It is a process of knowledge. It is for this reason that the use of low boiling point solvents is preferred. especially , this oligomer starts curing at a low temperature of about 110°C, so It is acceptable to use sufficient heat to form a cured coating. This soft base Store in vacuum, in an inert atmosphere (e.g. nitrogen, helium, argon, etc.) or in air. It can be carried out inside.

A mask containing the desired turns or images is placed on or onto the painted substrate. placed adjacent to each other, and then this oligomer coating is exposed to X-rays, electron beams, Irradiation by ion beam, ultraviolet light or visible light. Economical and easy to manufacture For reasons of radiation in the range of about 200 to about s　o　nm. ) is preferably used. Lower wavelength rays tend to give better resolution. Therefore, irradiation within the range of 200 to 500 nm is preferable. Through this treatment, the coating film The irradiated portion of It becomes rather insoluble in the same solvent in which the sesame is still actually soluble.

Irradiation is carried out either in the presence or absence of oxygen. of the required solubility properties. The exposure time required for sufficient photocrosslinking to produce a difference depends on the wavelength of the light used and its intensity. , from a few seconds to a few minutes, depending on the presence or absence of the photosensitizer or sensitizer, etc. Change. For manufacturing purposes, short exposure times are highly preferred. The photosensitive film of the present invention One of the desirable properties of oligomers is that they are photochemically stable throughout the thickness of the film. cross-linking, so that the pattern has a minimal undercut shape during development. Indicates completion.

Selective patterns emerge upon development with solvents. As mentioned above, during irradiation, The photopolymer resin is extensively crosslinked, and this is followed by crosslinking or illumination of the oligomer. It shows a large solubility difference between the irradiated portion and the non-crosslinked or non-irradiated portion. used for development The solvent used is generally the same as that used to prepare the oligomer solution for the coating. be. Therefore, the types of solvents are aprotic solvents, aromatic hydrocarbons, and halogenated carbons. Contains hydrohydrides, ketones, esters, calpitol and mixtures thereof. During development A selective pattern appears, with high areas corresponding to photochemically crosslinked oligomers. next , thermosetting these relief structures makes them resistant to high temperatures, chemical decomposition, and ion transport. Highly cross-linked, highly resistant and serves as an effective protective and dielectric insulating layer , an infusible, insoluble glassy solid is obtained. Curing occurs due to crosslinking of vinyl groups. , thermally, chemically or photochemically, although thermal curing is preferred.

Heat curing is generally carried out at a temperature range of about 200 to about 300°C, often several Implemented in stages. So, for example, curing is first carried out at a temperature of about 200 to about 200°C. 0. It is carried out for 5 to 5 hours, and the temperature is about 0.5 to 180℃ to 300℃. Curing takes place after 24 hours. Curing can be done with e.g. azo-bis-isobutyronitrile, peroxide, etc. Using free radical initiators such as benzoyl oxide, di-t-butyl peroxide, etc. It will be implemented even if

The oligomers of the present invention are applied as a solution with high solids levels, and a small amount of This method is particularly useful for photodefinable applications, as the solvent only needs to be evaporated. It's clear. Additionally, no volatile by-products are generated during curing, making the film more stable. Shrinkage is minimal.

Multilayer processing Substrates (i.e. ceramic, alumina, silicon, printed wiring boards, etc.) are Cleaning solvents (e.g., methylene chloride, chloroform, Loloethylene, ethanol, methanol, sodium bisulfite, sodium sulfite um, potassium sulfite, etc.) using conventional cleaning methods known in the art. be done. Additionally, the substrate can include circuitry already deposited thereon. The board is Can be used after cleaning process or substrate and metal and/or polymer dielectric The surface can be treated to promote adhesion between the layers.

If used, an adhesion promoter between the substrate and the dielectric layer may be reacted with the polymer of the invention. The surface silylating agent can be selected from a range of surface silylating agents containing reactive groups that can be used.

Usable surface silylating agents are: vinylmethyldimethoxysilane, vinyltrimeth xysilane, vinylmethyljethoxysilane, vinyltriethoxysilane, gel Toxymethylvinylphenethylsilane, dimethoxymethylvinylphenethylsilane Triethoxyvinylphenethylsilane, Trimethoxyvinylphenethylsilane N et al. Preferred silylating agents are vinylmethyldimethoxysilane, vinylmethoxysilane, Jetoxysilane, Jetoxymethylvinylphenethylsilane and Dimethoxy It is methylvinylphenethylsilane. Surface silylation agents can be applied by dipping, spin coating or Other methods apply to the substrate from an alcohol-water solution. For example, silylation A 1-10% solution by weight of the agent in 85-98% alcohol (e.g. methanol) , ethanol, impropatul, etc.) and 1-13% by weight of water.

The substrate was immersed in this solution for 15 seconds to 5 minutes, air-dried for 1 minute to 5 hours, then convection 60-100℃ for 1 minute to 5 minutes in either a furnace, vacuum oven or hot plate Let soft bake for an hour. The cleaned and/or surface-treated substrate is then coated with the dielectric layer of the present invention. coated with a metal pattern before being coated with a metal pattern. For example, 500 to 1 of chromium 000 people layer, copper 8000~20000 people layer and chrome 500~1000 people layer Sputter onto the surface. This metal layer is then covered with a commercially available photoresist. reverse and spin according to the desired processing scheme. Processing using paint, soft bake, imaging, development and hard bake cycles do. This is done by etching the metal layer to be removed and patterning it. form. Etch the metal using standard wet methods, e.g. The layer is treated with a 1-30% hydrochloric acid solution activated by aluminum for 10 seconds to 5 minutes. Etch the copper layer with sodium persulfate solution for 10 seconds to 10 minutes. the lower chromium layer in a 1-30% hydrochloric acid solution activated by aluminum. Therefore, etching is performed for 10 seconds to 5 minutes; finally, the etched substrate is deionized. Wash with water for 10-60 seconds. Next, remove the remaining photoresist from the photoresist. The resist is peeled off from the metal pattern using a processing method that is desirable for the resist. lastly, The cleaned surface is allowed to dry before the next processing step.

A dielectric layer is applied over the substrate and its metal pattern and processed as follows: Polymer (10-80 in a suitable solvent (e.g. toluene, NMP, DMF, etc.) % by weight) onto the substrate for 30-90 seconds at a speed of 500-2500 rpm. Paint the prepolymer-coated substrate with nitrogen bleed or heat treatment. Soft bake in a vacuum oven for 15 minutes to 24 hours at a temperature of 25 to 60°C. the soft-baked coating is then exposed to a UV light source (220-320 nm range). for 15 seconds using a mask of a preferred design for bias (v i as ). Imaging for ~30 minutes: The photocured polymer is then washed with a suitable solvent system (e.g. toluene, toluene/hexane, toluene/ethanol, cyclohexane, etc.) Thus, at 25-35° C. with or without ultrasound, or at 15-12° C. Develop by spraying for 0 seconds; the developed substrate is then exposed to a stop bath or Miscible in rinse baths or with developer solvents, but poor solvent for polymer systems Solvent sprays based on solvent systems other than (e.g. hexane, pentane, ethanol, etc.) (optional step): bias is then exposed to plasma or wet Clean by etching: Finally, the dried substrate is placed under vacuum or in an inert Under an atmosphere (nitrogen, argon, etc.), a lamp 30 at 25°C to 300°C minutes to 2 hours, maintained at 300°C for 1 hour, then ramped for 30 minutes to 3 hours. Hard bake with a curing cycle including cooling from 300°C to 25°C.

This is used to form an electronic interlocking structure with the desired electrical and dielectric level. Repeat the process as necessary.

Example 1 Styrene-terminated para-cresol dicyclopentadiene (STPCDP (70V Synthesis of Bz/30Pr) Mechanical starchy, addition funnel, cooling tube, thermometer, nitrogen purge and Therm- N-Methylpyro in a 2000 m 1 triple round bottom flask equipped with an O-Watch In 700 ml of lysinone (NMP), add powder from Borden Chemical. Lacresol dicyclopentadiene (PCDP) (Mn=520.Mw=11 00, dispersion degree 2.12) 200.0g was dissolved. vinylben in this reaction mixture. Zyl chloride (60/40 para/meta isomer ratio) 123.06g (0,806 mole) and 0.30 g of 2.6-tert-butyl-p-cresol (BHT) added. The reaction mixture was heated to 60°C and dissolved in 125 ml of methanol. 52.78 g (0,941 mol) of lithium was added dropwise over a period of 30 minutes. reaction was maintained at 60° C. for 16 hours with stirring under nitrogen purge. In this reaction mixture Add 31.32 g (0,254 mol) of n-propylbromide, then add methanol Potassium hydroxide in LeSQml 15. 34g (0,273mol) in 1 hour Added across. The reaction was maintained at 60° C. for 3.5 hours before being allowed to cool to room temperature.

Transfer the reaction mixture to a separatory funnel, add 2.0 liters of toluene, then add 1 liter of water. ．． Wash 3 times with 0 liters, dry over magnesium sulfate, filter and concentrate in vacuo. A red resinous product was obtained; Mn=630. Mw=1200. Dispersion degree 1.9° Example 2 Styrene-terminated para-cresol dicyclopentadiene (STPCDP (70V Synthesis of Bz/30Pr) Mechanical starchy, addition funnel, cooling tube, thermometer, nitrogen purge and Therm- N-Methylpyro in a 5000 ml three-way round bottom flask equipped with an O-Watch. Lysinone (NMP) from Borden Chemical in 1750 ml. Vara-cresol dicyclopentadiene (PCDP) (Mn=520.Mw=1 100, dispersity 2.12) 500.0g was dissolved. Add vinyl vinyl to this reaction mixture. 307.65g (60/40 para/meta isomer ratio) (2,01 6 mol) and 2.6-tert-butyl-p-cresol (BHT) 1.43 g was added. The reaction mixture was heated to 60 °C and hydroxylated in 312 ml of methanol. 131.95 g (2.35 mol) of potassium were added dropwise over a period of 6.0 hours.

The reaction was maintained at 60° C. for 16 hours with stirring under a nitrogen purge. This reaction mixture Add 78.30 g (0,637 mol) of n-propyl bromide to the mixture, then add meth 38.35 g (0,630 mol) of potassium hydroxide in 200 ml of alcohol Added over a period of minutes. The reaction was maintained at 60°C for 3.5 hours, then cooled to room temperature. I set it.

Transfer the reaction mixture to a separatory funnel, add 2.0 liters of toluene, then add 2.0 liters of water. ．． 0 liter, one wash with saturated sodium chloride solution, and finally saturated sodium chloride solution. Wash with ammonium solution, dry over magnesium sulfate, filter and concentrate in vacuo. A red resinous product was obtained; Mn=500. Mw-960, dispersity 1.9 ゜Example 3 Styrene-terminated para-cresol dicyclopentadiene (STPCDP (70V Synthesis of Bz/30Pr) Mechanical star sea, addition funnel, cooling pipe, thermometer, Th　rm-0-Wa　 Paraculate into a 10100O Mikka round bottom flask equipped with tch and nitrogen purge. 324.0 g (2,996 mol) of resol was charged. This reaction flask was Heat to 90°C under stirring. Add fluoride trifluoride to the molten p-cresol. Add 0 ml (0,041 mol) of urinary nitrate. In this reaction mixture Dicyclopentadiene 262, Og (1,982 mol) was added over 2.2 hours. and the reaction was maintained at 90°C for 1 hour with stirring; then unreacted p-creso The mol was removed from the reaction mixture in vacuo. Vara-cresol dicyclopentadiene ( PCDP) resin was isolated by pouring it into a stainless steel pan and brought to room temperature. Cooled; Mn=650. Mw=1500. Dispersity 2.31゜Rose from above - 207.2 g of cresol dicyclopentadiene (PCDP) was added to a mechanical star Sheet, addition funnel, cooling tube, thermometer, nitrogen purge and Therm-0-Watc N-Methylpyrrolidinone (N MP) dissolved in 700 ml. Vinylbenzyl chloride (6 0/40 rose/meta isomer ratio) 127.5 g (0,835 mol) and 2.6-shi -0.20 g of tert-butyl-p-cresol (BIT) was added. reaction mixture The mixture was heated to 60°C and 54.68 g of potassium hydroxide in 130 ml of methanol (0,975 mol) was added dropwise over 2.0 hours. Run the reaction under nitrogen purge Maintained at 60° C. for 16 hours with stirring. This reaction mixture was added with n-propyl alcohol. Add 32.45 g (0,263 mol) of Lomid, then add 15.89 g (0,283 mol) of potassium hydroxide was added over 1.33 hours. I got it. The reaction was maintained at 60° C. for 8 hours before being allowed to cool to room temperature. This reaction mixture Transfer to a branch funnel, add 1.5 liters of toluene, then add 2.0 liters of water. Washed three times, dried over magnesium sulfate, filtered and concentrated in vacuo to a red resinous form. A product was obtained; Mn=770. Mw=1400. Dispersion degree 1.82゜mechanical star Sea, addition funnel, cooling pipe, thermometer, Th e rm-0-Watch and Borden C in a 2000 m 3-hole round bottom flask equipped with a nitrogen purge. Vara-cresol dicyclopentadiene (PCDP) from chemical (M n=520. Mw=1100. Dispersity 2.12) 500.0g and ortho-dichloro 420ml of lobenzene was charged. The reaction mixture was heated to 60 °C with stirring under nitrogen. After the PCDP is completely dissolved, add boron trifluoride nitrate, 0 ml (0,041 mol) was added. Dicyclopentadiene 7 was added to this reaction mixture. 1.12 g (0,538 mol) was added over 1.1 hours, during this addition: The reaction was maintained at 60°C with stirring; the reaction was then heated to 150°C for 4 hours. . Ortho-dichlorobenzene and unreacted dicyclopentadiene are removed from the reaction mixture. It was distilled off in vacuo. Stereo-cresol dicyclopentadiene (PCDP) resin Yield 33, isolated by pouring into a stainless steel pan and allowed to cool to room temperature. 2.0g; Mn=800. Mw=2500. Dispersity 3.12゜Rose from above 318.5 g of cresol dicyclopentadiene (PCDP) was -, addition funnel, cooling tube, thermometer, nitrogen purge and Therm-0-Watch N-Methylpyrrolidinone (NM P) Dissolved in 1100 ml. Vinylbenzyl chloride (6 0/40 para/meta isomer ratio) 195.0 g (1,278 mol) and 2.6-cy -0.30 g of tert-butyl-p-cresol (BIT) was added. reaction mixture Heat the mixture to 60°C and add 84.05 g of potassium hydroxide in 200 ml of methanol. (1,498 mol) was added dropwise over 3 hours. Stir the reaction under nitrogen purge The temperature was maintained at 60° C. for 16 hours. Add n-propyl bromide to this reaction mixture. 49.88 g (0,406 mol) of hydroxyl in 125 ml of methanol was added, followed by 24.43 g (0,435 mol) of potassium chloride were added over a period of 2 hours. reaction was maintained at 60° C. for 4 hours and then allowed to cool to room temperature. Transfer this reaction mixture to a separatory funnel. Add 1.5 liters of toluene, then add 4.0 liters of water once to saturate. Wash twice with sodium chloride solution, dry over magnesium sulfate, filter, and Vacuum concentration gave a red resinous product; Mn=700. Mw=1600, degree of dispersion 2.3゜ Example 5 Styrene-terminated para-cresol dicyclopentadiene (STPCDP (70V Synthesis of Bz/30Pr) Mechanical star sea, addition funnel, cooling pipe, thermometer, Th　rm-0-Wa　 10100O four-necked resin kettle equipped with tch and nitrogen purge 324.0 g (2,996 mol) of resol was charged. This reaction flask was Heat to 90°C under stirring. Add fluoride trifluoride to the molten p-cresol. Add urinary nitrate, Oml (0,041 mol). In this reaction mixture 288.2 g (2,180 mol) of dicyclopentadiene was added over 1.5 hours. and the reaction was maintained at 90°C for 1 hour with stirring; then unreacted p-creso The mol was removed from the reaction mixture in vacuo. Para-cresol dicyclopentadiene ( PCDP) resin was isolated by pouring it into a stainless steel pan and brought to room temperature. Cooled, yield 456.0g; Mn-720, Mw=1900. Dispersion degree 2.6 4° Para-cresol dicyclopentadiene (PCDP) from above 436.0 g, mechanical starch, addition funnel, cooling tube, thermometer, nitrogen purge and the N-Methi in a 2000 m 1 triple round bottom flask equipped with rm-0-Watch Dissolved in 1200 ml of lupyrrolidinone (NMP). vinyl in this reaction mixture. Benzyl chloride (60/40 bulk/meta isomer ratio) 269.0g (1,76 3 mol) and 2,6-tert-butyl-p-cresol (BHT) 0.45 g was added. The reaction mixture was heated to 60 °C and hydroxylated in 250 ml of methanol. 106.0 g (1,890 mol) of potassium was added dropwise over 2.5 hours.

The reaction was maintained at 60° C. for 16 hours with stirring under a nitrogen purge. This reaction mixture 102.0 g (0,829 mol) of n-propylbromide was added to the mixture, and the mixture was purified under purging. The mixture was heated to 60° C. with stirring. This reaction mixture was then added with 120ml of methanol. 35.4 g (0,631 mol) of potassium hydroxide in 1 was added over 1.5 hours. added. The reaction was maintained at 60° C. for 3 hours before being allowed to cool to room temperature. Next, the reaction mixture Transfer the mixture to a separating funnel, add 4 liters of toluene, then add 2.0 liters of water. Washed 4 times, once with saturated sodium chloride solution, dried over sodium sulfate and filtered. Filtration and concentration in vacuo gave a red resinous product; Mn=780. Mw=1600. Dispersion degree 2゜1゜ Mechanical star sea, addition funnel, cooling pipe, thermometer, Th　rm-0-Wa　 Parac in a 10100O three-necked bottom flask equipped with tch and nitrogen purge. 628.0 g (5,807 mol) of resol was charged. This reaction flask was Heat to 90°C under stirring. Add fluoride trifluoride to the molten p-cresol. Uron etherate12. Add Oml (0,082 mol). This reaction mixture 524.0 g (3,963 mol) of dicyclopentadiene was added over 3.0 hours to and the reaction was maintained at 90°C for 1 hour with stirring; The sol was removed from the reaction mixture in vacuo. para-cresol dicyclopentadiene (PCDP) resin was isolated by injecting it into a stainless steel pan and at room temperature. 612.2 g of resin were obtained: Mn=990. Mw=2900. Dispersity 2.9 para-cresol dicyclopentadiene (PCDP) from above 5 91.2g was added to the mechanical starchy, addition funnel, cooling tube, thermometer, nitrogen purge and in a 5000 ml three-way round bottom flask equipped with a Therm-0-Watch. Dissolved in 1200 ml of N-methylpyrrolidinone (NMP). This reaction mixture 364.6 g of vinylbenzyl chloride (60/40 para/meta isomer ratio) ( 2,389 mol) and 2,6-tert-butyl-p-cresol (BHT) 0.6g was added. The reaction mixture was heated to 60°C and dissolved in 325 ml of methanol. 147.4 g (2,627 mol) of potassium hydroxide was added dropwise over 2 hours. . The reaction was maintained at 60° C. for 6 hours with stirring under a nitrogen purge. This reaction mixture 157.0 g (1,276 mol) of n-propyl bromide was added to the mixture, and then meth 71.82 g (1,280 mol) of potassium hydroxide in 165 ml of alcohol was added at 2 hours. added over time. The reaction was maintained at 60° C. for 4 hours before being allowed to cool to room temperature.

Next, the reaction mixture was transferred to a separatory funnel, 4.0 liters of toluene was added, and then water was added. Wash three times with 2.0 liters, dry over sodium sulfate, filter, and concentrate in vacuo. Condensation gave a red resinous product; Mn=740. Mw=1500. Dispersion degree 2.0 3゜Example 7 Styrene-terminated para-cresol dicyclopentadiene (STPCDP (70V Synthesis of Bz/30Pr) Mechanical star sea, addition funnel, cooling pipe, thermometer, Th　rm-0-Wa　 Bo Para-cresol dicyclopentadiene (P) from rden Chemical CDP) (Mn=520.Mw=1100.Dispersity 2.12) 500.0g and 500 ml of dichlorobenzene was charged. The reaction mixture was stirred under nitrogen. After the PCDP is completely dissolved, add boron trifluoride ether. terate 1, Oml (6,83xlO-"mol) was added. To this reaction mixture 71.12 g (0,538 mol) of dicyclopentadiene over 45 minutes and maintained the reaction at 60° C. with stirring during this addition; Heated to 0° C. for 4 hours and then allowed to cool to ambient temperature. Reaction mixture in methanol Solidify by adding, filter and dry in a vacuum oven at 80 °C overnight. Set; Mn near 00, Mw=1500. Dispersity 2.14゜parak from above 308.0 g of resol dicyclopentadiene (PCDP) was added to mechanical starch , addition funnel, cooling tube, thermometer, nitrogen purge and Therm-0-Watch N-Methylpyrrolidinone (NMP) in a 2000 m triplicate round bottom flask equipped with ) was dissolved in 1050 ml. Vinylbenzyl chloride (60% /40 para/meta isomer ratio) 189.0 g (1,238 mol) and 2,6-cy 0.20 g of tert-butyl-p-cresol (BHT) was added. reaction mixture Heating the material to 60°C, 76.82 g of potassium hydroxide in 225 ml of methanol (1,370 mol) was added dropwise over 1.75 hours. Run the reaction under nitrogen purge Maintained at 60° C. for 4.2 hours with stirring. This reaction mixture was added with n-propyl alcohol. Add 78.83 g (0,640 mol) of Romid, then add in 125 ml of methanol. 35.91 g (0,640 mol) of potassium hydroxide was added over 2 hours. . The reaction was maintained at 60° C. for 16 hours before being allowed to cool to room temperature. This reaction mixture Transfer to a separating funnel, add 3 liters of toluene, then wash 3 times with 2.0 liters of water. Clean, dry over magnesium sulfate, filter, and concentrate in vacuo to yield a red resin. 332.0g of product was obtained; Mn=670. Mw=1300. Dispersion degree 1.9° Example 8 Styrene-terminated para-cresol dicyclopentadiene (STPCDP (70V Synthesis of Bz/30Pr) Mechanical star sea, addition funnel, cooling pipe, thermometer, Th　rm-0-Wa　 Bo Para-cresol dicyclopentadiene (P) from rden Chemical CDP) (Mn=520.Mw=1100.Dispersity 2.12) 500.0g and 500 ml of luto dichlorobenzene was charged. The reaction mixture was stirred under nitrogen. After heating to 60℃ and completely dissolving PCDP, add boron trifluoride ether. Rate 1, Oml (6,83xlO-3 mol) was added. Add dilution to this reaction mixture. 59.26 g (0,448 mol) of cyclopentadiene was added over 2 hours. , the reaction was maintained at 60°C with stirring during this addition; then the reaction was heated to 150°C. The mixture was heated for 4 hours and then allowed to cool to ambient temperature. Add reaction mixture to methanol Coagulated by washing, filtering and drying in a vacuum oven at 80°C overnight. : Mn=630, Mw=1400. Dispersity 2.22゜ Para-creso from above 146.22 g of polydicyclopentadiene (PCDP) was added to Addition funnel, cooling pipe, thermometer, nitrogen purge and Therm-0-Watc N-Methylpyrrolidinone (N MP) dissolved in 600 ml. Vinylbenzyl chloride (6 0/40 para/meta isomer ratio) 64.76 g (0,424 mol) and 2,6-cy -0.15 g of tert-butyl-p-cresol (BHT) was added. reaction mixture Heat the mixture to 60°C and add 23.81 g of potassium hydroxide in 5 Qml of methanol. (0,424 monomer was added dropwise over 1.2 hours. The reaction was stirred under a nitrogen purge. The temperature was maintained at 60° C. for 4.0 hours while stirring. Add n-propylpropylene to this reaction mixture. Add 40.14 g (0,326 mol) of amide, then water in 40 ml of methanol. 18.32 g (0.327 mol) of potassium oxide were added over a period of 1 hour. anti The reaction was maintained at 60° C. for 4 hours and then allowed to cool to room temperature. This reaction mixture is then divided into Transfer to a liquid funnel, add 1 liter of toluene, then wash 3 times with 1 liter of water, Dry over sodium sulfate, filter, and concentrate in vacuo to give a red resinous product. ;Mn=710. Mw=1400. Dispersity: 1.97° Example 9 Styrene-terminated tetraphenol ethane (70% vinylbenzyl/30% propyl ) (STTPE (70VBz/30Pr)) synthetic stirring shaft, addition funnel In a 250 m1 three-day round-bottomed flask equipped with a cooling tube, add tetraphenol ether. (TPE) (Mn=274.Mw=711) 25.0g (0,0354mol ), BHT O, 23g (0,00106 mol), and N-methylpyrroli 120 ml of Zinone (NMP) was added. When dissolving TPE, vinyl benzyl Add 26.48g (0,174mol) of Loride (VBC) and flush the container. and placed under positive nitrogen pressure with a mineral oil bubbler. This solution was washed for 60 minutes in a water bath. 11,34 g (0,177 mole) of KOH dissolved in 25 ml methanol heated to ) was added dropwise over a period of 30 minutes. Maintain this mixture at 60°C for an additional 1.3 hours. 1-bromopropane9. Oml (0,099 mol) was added. Next 4.86 g (0.0758 mol) of KOH dissolved in 11 ml of methanol was added to Additions were made 9 times over 30 minutes, and the temperature was maintained at 50'C for an additional 1.5 hours.

The mixture is cooled and added slowly to 600ml of methanol, leaving a yellow solid. I stayed. Discard the methanol and enter this solid with fresh methanol into the blender. An oily solid was formed which was collected in a Buchner funnel. remove this substance Dissolved in lolomethane and washed with 4×500 ml of water. Sodium sulfate organic phase Dry on top and filter through Celite. Remove the solvent by rotary evaporator. A 49% yield of an orange semi-solid was obtained. GPC test of resin is Mn Ni 1040, Mw=1290. It shows a dispersity of 1.24. Infrared analysis of the resin revealed some residual OH (< 5%), and ion chromatography showed 17 ppm CI-, <lppmBr -, lppm5o4-''.

2 liter three day round bottom flask equipped with stirring shaft, addition funnel and condenser tube , tetraphenolethane (TPE) (Mn=274.Mw=711) 200 ．． 0g (0,284 mol),! :, BHT 1.88g (0,00852 mo /l/)(!:, 950 ml of N-methylpyrrolidinone (NMP) was added.T When dissolving PE, 242.65 g of vinylhensyl chloride (VBC) (1,5 9 mol) and the vessel was flushed and placed under positive nitrogen pressure with a mineral oil bubbler. Ta. This solution was heated to 60 °C by water bath and dissolved in 230 ml of methanol. 95 g (1.59 mol) of KOH 101 was added dropwise over a period of 30 minutes. this The mixture was heated to 60° C. and maintained for 4.7 hours. VBC 15.17 g (0. 0994 ru) was added. Next, KOH6,37 dissolved in 15 ml of methanol g (0,0994 mol) was added dropwise. 1゜Finally after 7 hours, VBC and K OH/methanol was added and the reaction was maintained at 60° C. for over 1 hour.

The mixture was cooled and 1.2 liters of toluene was added. Mixture in 1 x 3 liters of water , washed with 2x3 liters of LM NaCl (aq). Sodium sulfate organic phase Dry on top, slurry through Celite, and filter. 3t of solvent.

rr, removal by rotary evaporator up to 40°C left a viscous brown resin. , 95% yield. GPC analysis shows Mn=778. Mw=1079. Dispersity 1.39 I actually measured it. Infrared analysis showed no residual hydroxyls (<0.5%) and ion chromatography showed no residual hydroxyls (<0.5%). Matography actually measured 45 ppm CI-.

Example 11 Example 6.7.8.4.5 corresponding to Sample 1.2.3.4.5 respectively Series of tyrene-terminated rose-cresol dicyclopentadiene (STPCDP) with the following curing cycle: 2 hours at 80°C and 16 hours at 100°C. 4 hours at 120°C, 16 hours at 160°C, 2 hours at 200°C. and cured for 1 hour at 225°C. The properties of the cured resin are shown in the table below. A Tg('C)''　＞300　＞300　＞300　＞300　＞300Ts p　(℃)　”’ 177±8 160±5 179±6 135±5 173 ±7α, p (ppm/℃)” 42f2 55±9 71±6 66110 5 7±5αtso(1)I)III/’C)”’96 Sat 7 85±12 155 ±4 125±5 86±2ε"" 2.73 2.86 2.78 2.72 2.70 tan δ" 0.0009 0.0001 0.001 0.000 4 0.003ε"" 2.75 2.89 2.80 2.74 2.74t an6i"' 0.004 0.004 0.005 0.002 0.002 Water absorption %'' 0.145 0.156 0.161 0.0g9 0.107 (a) Glass transition temperature measured by differential scanning calorimeter (b) ThermoMe Softening point due to small thermal transition (c) Coefficient of thermal expansion between 25°C and softening point (d) Coefficient of thermal expansion between 25°C and 260°C Tensile modulus (e) IMHz, dielectric constant (f) IMHz at 25°C and 0% relative humidity , dissipation factor (g) IMHz at 0% relative humidity at 25°C, phase at 25°C Dielectric constant (h) at 50% relative humidity IMHz, dielectric constant at 50% relative humidity at 25°C Dissipation tangent (i) 168 hours at 25°C and 50% relative humidity Example 12 A series of coating solutions were prepared and used for application to silicon surfaces. The solution concentration is 56% by weight of 5TPCDP from Example 6 in toluene. This solution is 950r Application was done by spin painting for 60 seconds at pm. Coated disc under vacuum , soft baked at 25°C for 18 hours. Next, add these to the quartz/water filter The specimens were exposed to UV radiation for 3 minutes using a 300 watt mercury vapor lamp with a lamp. irradiated The coated films were then exposed to various solvents and the amount of cured resin dissolved was measured. Result is Shown in the table below.

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30 2.16 2.69 0.83 0.56 0.84 0.8860 4 ．． 32 2.69 2.20 0.83 2.23 0.8890 3.51 2.44 2.20 0.56 2.23 1.46120 3.51 3.1 8 1.65 1.67 0.84 1.75180 3.24 2.69 0 ．． 00 2.78 0.84 1.75300 5.68 4.89 1.38 1.67 0.00 -0.29 (a) Coated on silicon wafer, 25 5TPCDP soft-baked for 18 hours at °C with quartz/water filter Cured for 3 minutes using a 300 watt mercury vapor lamp. (b) wt% solution Table C time (seconds) 100:0 80:20 60:40 40:60 20:80 0:100o 　oooooo.

30 2.16 -0.90 -1.50 -1.45 -1.63 -1.4 260 4.32 0.00 0.00 -0.87 0.00 -0.289 0 3.51 0.30 0.00 -1.16 0.00 -0.28120 3.51 0.60 0.60 0.29 0.27 -0.57180 3 ．． 24 0.30 1.20 0.00 0.82 0.00300 5.68 1.80 -0JO-0,290,82-0,28 (a) On silicon wafer 5TPCDP, quartz/coated and soft baked for 18 hours at 25°C Cure for 3 minutes using a 300 watt mercury vapor lamp with water filter (b) wt% solution For Tables B and C, only soft baking was performed and no curing by UV irradiation was performed. The results of E can be compared with the table below.

appearance time (seconds) 100:0 80:20 60:40 40:60 20:80 0:100o 　oo　oooo.

30 97.38 97.69 90.06 15.16 -4.02 0.0 060 101.46 100.58 100.00 41.11 -0.93 0.0090 102.33 100.00 100.28 57.73 0 ．． 00 2.35120 102.04 100.00 99.72 63.5 6 1.55 1.76180 101.46 100.29 100.57 69.68 2.79 -0.29300 100.00 100.29 10 0.57 74.34 0.93 -0.59 (a) Coated on silicon wafer 5TPCDP and soft baked at 25° C. for 18 hours.

(b) wt% solution time (seconds) too:o 80:20 60:40 40:60 20:80 0:100o 　oo　oooo.

30 97.38 101.71 -2.82 -2.82 -3.42 -0 ．． 5860 101.46 103.43 12.43 87.32 9.97 -1.1790 102.33 104.29 65.54 103.38 60.40 -0.58120 102.04 104.00 92.66 1 04.23 74.36 0.58180 101.46 104.00 96 ．． 33 102.82 83.19 -0.58 (a) Coated on silicon wafer 5TPCDP fabricated and soft baked for 18 hours at 25°C.

(b) wt% solution Example 13 Using various concentrations of 5TPCDP from Example 6 in toluene, a series of 5TPCDP A CDP solution was prepared. Apply these solutions to the silicon substrate (surface) at a concentration of 600 to 2000 Spin coat for 60 seconds using a spin coating speed of rpm at 25 °C (at λ). Soft bake for 24 hours. The sample was then tested with USAF test strips and quartz. / 3 minutes of UV irradiation with a 300 watt mercury vapor lamp using a water filter exposed to light. The photocured polymer was then developed in toluene for 1 minute at 25°C. did. The air-dried substrate was subjected to a 1-hour vacuum curing cycle at 25°C to 220°C. Hard-baked using .

Taylor-Hobson Taylor Sur Using a f10 profilometer (prof i lometer) 1. %hand analyzed. The table below shows the film thicknesses obtained.

deep red 5TPCDP viscosity film thickness μm) (s+pa s) 600 published by Rainbow State gall 4 Yo 4 Peeking concave 36.7 5.0 --- 4.4 --- 3.6 2.8 ---50.0% 15.0 8.8 8.6 7.9 7.2 6. 1 5.852.6% 22.0 --- 11.3 --- 9.8 8.0 ---(a) Dissolved solid content in toluene A series of 5TPCDP using various concentrations of 5TPCDP from Example 6 in toluene. A DP solution was prepared. Apply these solutions to the silicon substrate (surface) for 600 to 2000 r. Spin coating for 60 seconds using a spin coating speed of pm; Soft bake for 4 hours. The sample was then tested with the USAF test pattern and quartz/water. 3 minute exposure to UV irradiation with a 300 watt mercury vapor lamp using a filter. I let it happen. The photocured polymer was then developed with toluene for 1 minute at 25°C. . The air-dried substrate was cured using a 1-hour vacuum curing cycle at 25°C to 220°C. Hard baked at 220° C. for 2.5 hours, then cooled to room temperature.

The film thickness and sidewall angle of the photocurable polymer were determined by 5loan Technol.

gy Corporation Dektak3030 profilometer It was analyzed using This data is summarized in the table below.

Table G Spin speed Film thickness Sidewall angle (rpm) (μm) 600 10, 0 31 600 10, 0 22 600 11, 5 13 600 12, 0 28 700 10, 8 16 700 8, 5 9 700 9, 4 39 700 11, 3 39 800 9, 7 13 800 7, 0 5 soo 9.　O1i 800 10, 0 10 1000 5, 9 7 1000 9, 4 12 1000 8, 5 22 1000 8, 3 17 1500 6, 4 24 1500 6, 5 23 1500 8, 0 6 1500 7, 0 20 2000 7, 0 15 2000 6, 8 23 2000 6, 2 24 Example 15 A series of 5TPCDP using various concentrations of 5TPCDP from Example 6 in toluene. A DP solution was prepared. Apply these solutions to the silicon substrate (surface) for 600 to 2000 r. Spin coating for 60 seconds using a spin coating speed of Soft bake for 4 hours. The sample was then tested with the USAF test pattern and quartz/water. 3 minute exposure to UV irradiation with a 300 watt mercury vapor lamp using a filter. I let it happen. The photocured polymer was then developed with toluene for 1 minute at 25°C. . The air-dried substrate was cured using a 1-hour vacuum curing cycle at 25°C to 220°C. Hard baked at 220° C. for 2.5 hours, then cooled to room temperature.

The sample was then metallized by ion beam sputtering to a thickness of 50 mm. A metal film of 00 to 1000 people was obtained.

Adhesion by calibrated “Scotch tape adhesion test before and after thermal shock cycling” evaluated the power. The thermal shock cycle was performed by thermal cycling the sample at 55°C for 1 time. 0 minute hold; -55°C to 125°C rapid ramp: Includes 10 minute hold at 125°C. nothing. In the table below, the ratios listed are for all squares out of 25 squares of metal. This means that the material was not removed by the tape. In other words, 25/25 is 5/25 means that all of the squares remained attached to the dielectric polymer, and 5/25 is the metal This means that 20 squares have been removed.

Adhesive force measurement results Metal layer Thermal shock After 92 cycles After 184 cycles Before cycling 2.51b, IO, 01b, 2.51b, 10.01b, 2.51b, 10. 01b.

Chrome 8/25 8/8 8/8 8/8 7/8 6/7 pass Copper 0/25 Nokusu Copper O/25 bus Aluminum 0/25 25/25 25/25 25/25 bus bus bar Bus Gold 0725 7 paddles Gold 0725 No(su) Nickel 0/25 bus Nickel 0/25 bus (a) No sample evaluation (b) Tape evaluation example 16 at Ib for 1/2 inch width tape The 5TPCDP resin of Example 5 was dissolved in toluene to give 5TPCDP47.2%. A solution having a composition of 52.8% toluene was obtained. This solution is applied to an alumina or silicon substrate. (Surface) for 60 seconds using a spin speed of 11000 rpm - Nitrogen Soft bake was performed at 60° C. for 1 hour. This polymer was then heated for 25 hours for 3 hours. ℃~220℃ lamp, 2. Maintained at 220℃ for 0 hours, then 220℃ for 4 hours Hard baked using a nitrogen curing cycle including a ~25°C lamp.

Adhesion by calibrated “Scotch tape adhesion test before and after thermal shock cycling” evaluated the power. The thermal shock cycle was performed by thermal cycling the sample at 55°C for 1 time. 0 min hold; rapid ramp from -55°C to 125°C; 10 min hold at 125°C included nothing.

Adhesive force measurement results Substrate Before thermal shock cycling After 92 cycles 2.5 10.0 2.5 10 ．． 0 1b, Ib, lb, lb.

Alumina 25/25 25/25 25/25 25/25 Pass Pass Pass 　Pass Silicon 25/25 25/25 25/25 25/25 Pass Pass Pass path Example 17 The 5TPCDP resin of Example 5 was dissolved in toluene to give 5TPCDP47.2%. A solution having a composition of 52.8% toluene was obtained. Apply this solution to the alumina substrate (surface) under nitrogen for 60 seconds using a spin speed of 11,000 rpm; Soft bake for 1 hour at 0°C. This polymer was then heated at 25°C for 3 hours. 220℃ lamp, 2. Maintained at 220℃ for 0 hours, then 220℃ for 4 hours ~ 2 Hard baked using a nitrogen cure cycle including a 5° C. lamp.

Adhesion by calibrated “Scotch tape adhesion test before and after thermal shock cycling” evaluated the power. Thermal shock cycle was carried out at 55°C for 1 time. 0 min hold knee 55°C to 125°C rapid ramp; 10 min hold at 125°C included nothing.

Adhesive force measurement results Substrate Before thermal shock cycling After 92 cycles 2.5 10.0 2.5 10 ．． 0 1b, Ib, 'Ib, Ib.

Chrome 25/25 25/25 25/25 25/25 Pass Pass Pass path Nickel 25/25 25/25 25/25 25/25 Pass Pass Pass bus Copper 25/25 25/25 25/25 25/25 Pass Pass Pass Pass Aluminum 25/25 25/25 a a pass pass Fri 25/25 25/25 25/25 25/25 Pass Pass Pass Pass a) No sample evaluation Styrene-terminated para-cresol prepared as described in Examples 4 and 9, respectively. Dicyclopentadiene (STPCDP) and styrene-terminated tetraphenolethane (STTPE) with the following curing cycle: 2 hours at 80°C, 100°C: 16 hours, 4 hours at 120℃, 16 hours at 160℃, 2 hours at 2oo℃, 225 Heat curing was carried out using 1 hour at ℃. Some properties of the obtained cured mixed resin are shown in the table below. Summarize.

Table A Tg ('C)''>300>300>300T S D Lb' 1 47±3 160±4 16I±2a so (ppm/℃)” 75±37 0±974±2αzso(ppI/’C)”’167±1 11 Kano 1493 ±2ε"" 2.75 2.79 2.77tan δ" 0.0003 0. 0005 0.003ε”” 2.76 2.85 2.77janδLh’ 0.002 0.001 0.0008 Water absorption%'' 0.102 0.110 0.136 Modulus GPa)” 9.1 9.2 8.9Tg (℃) Lk'>200>200>200 (a) Gauge by differential scanning calorimeter Las transition temperature (b) Thermo Mechanical Analysis fine Softening point due to small thermal transition (c) Coefficient of thermal expansion between 25°C and softening point (d) Coefficient of thermal expansion between 25°C and 260°C tension (e) IMHz, dielectric constant (f) IMHz at 25°C and relative humidity 0%, Dissipation tangent (g) IMHz at 0% relative humidity at 25°C, relative at 25°C Dielectric constant (h) at 50% humidity IMHz, dielectric constant at 50% relative humidity at 25°C Tangent (i) 168 hours at 50% relative humidity at 25°C (168 hours at 04Hz) Modulus (k) measured from 125°C to 200°C - Scanned from 125°C to 200°C Also, the glass transition temperature due to DMA in 4H2 Example 19 A series of coating solutions were prepared and used for application to silicon surfaces. Solution concentration is torr 5TPCDP (Example 5) and 5TTPE (Example 9) (7) 50.　 It was 8 to 53.1% by weight. Spin the solution at 900-950 rpm for 60 seconds Applied by painting. The coated discs were placed under vacuum at 25°C for 18 hours. Soft baked. These were then placed in a 300 watt mercury evaporator with quartz/water filter. It was exposed to UV irradiation by a gas lamp for 3 minutes. The irradiated coating is then treated with various solvents. The amount of cured resin dissolved was measured. The results are shown in the table below.

Aodan Removal 5TPCDP/5TTPE (1)% solvent (toluene:ethanol) (11 1 hour (seconds) 100:0 80:20 60:40 40:60 20:80 0:100o 　oo　oooo.

30 3.59 6.29 11.30 9.42 26.98 0.3460 2.99 7.86 12.62 11.69 30.15 0.0090 6.29 10.38 13.95 14.94 34.60 2.03120 6.59 10.69 15.211! 16.56 35.24 2.03 180 8.08 11.32 16.28 16.56 35.24 1.6 9300 5.39 9.12 15.61 17.86 34.92 0.6 8a) Coated on silicon wafer, soft baked at 25°C for 18 hours, English/Cured for 3 minutes in a 300 watt mercury vapor lamp with water filter, 9 ゜5TPCDP/l05TTPE (weight) b) Weight% solution Table C time (seconds) 100:0 80:20 60:40 40:60 20:80 0:100o 　oo　oooo.

30 3.59 -1.71 -2.76 0!6 0.34 -0.6660 2.99 -1.71 5.17 2.87 -0.67 -2.3290 6.29 -2.05 15.17 8.24 2.69 -0.33120 6.59 -1.71 18.62 15.41 6.73 -0.66180 8.08 -2.05 21.38 23.66 14.81 0.0030 0 5.39 -3.07 24.83 28.32 25.25 1.99a ) Coated on a silicon wafer, soft-baked at 25°C for 18 hours, and coated on a quartz/ 90S cured for 3 minutes in a 300 watt mercury vapor lamp with water filter TPCDP/108TTPE (weight) b) Weight % solution For Tables B and C, only soft baking was performed and no curing by UV irradiation was performed. The results of E can be compared with the table below.

appearance time (seconds) 100:0 80:20 60:40 40:60 20:80 0:100o 　oo　oooo.

30 99.08 99J2 100.00 41.55 96.92 1.7 260 98.16 98.98 99.34 53.72 99.32 1. 0390 100.61 100.68 101.97 71.2g 100. 34 1.37120 99.69 101.36 100.99 73.31 100.00 2.06180 100.92 100.68 100.00 77.70 100.68 2.41300 99.69 100.34 1 00.33 79.05 99.32 2.41 (a) Coating on silicon wafer 90STPCDP/108 fabricated and soft baked for 18 hours at 25°C TTPE.

(b) wt% solution time (seconds) Hirokuni film thickness Enrin Chaiku Hiroki thickness o　oo　oooo.

30 99.08 102.14 13.57 -3.03 1.69 -0. 7060 98.16 101.42 91.79 30.64 -1.36 -1.7590 100.61 101.07 9g, 57 78.11 8. 81 -1.05120 99.69 102.49 98.57 95.62 29.83 0.35180 100.92 101.42 99.64 9 7.31 62.03 0.70 and) Coated on silicon wafer, 25℃ odor Soft baked for 18 hours, 90STPCDP/108TTPE (weight)b )wt% solution Solvent (toluene:ethanol) (b) time (seconds) 100:0 80:20 60:40 40:60 20:80 0:100o 　oo　oooo.

30 53.97 64.84 64.38 20.00 -2.05 0.0 060 69.21 70.33 70.21 30.36 -2.05 -1 ．． 3990 70.86 73.63 70.89 37.50 -0.68 -1.39120 71.85 71.79 71.58 42.50 -1. 02 0.69180 71.85 74.36 72.95 45.36 - 1.37 0.35300 74.83 74.73 73.29 50.71 0.34 0.35a) Coated on silicon wafer, 18 hours at 25°C Soft bake and 300 watt mercury vapor lamp with quartz/water filter 75STPCDP/25STTPE (weight) b) wt% solution cured for minutes Table G time (seconds) 100:0 80+20 60:40 40:60 20+80 0:100o 　oo　oooo.

30 53.97 69.47 0.73 -1.10 1.01 -0.70 60 69.21 73.33 18.18 8.46 -0.34 -1.7 690 70.86 77.89 42.55 30.15 0.34 -2. 821.20 71.85 7g, 25 48.73 41.54 1.35 -1.41180 71.85 78.25 52.36 51.84 3.0 3 -1.06300 74.83 81.40 54.55 60.29 6 ．． 40-1.76a) Coated on silicon wafer, soaked at 25°C for 18 hours. Bake for 3 minutes using a 300 watt mercury vapor lamp with quartz/water filter. 75STPCDP/25STTPE (weight) b) wt% solution, cured for a while In Tables F and G, only soft baking was performed and no curing by UV irradiation was performed. The results can be compared with the results in Tables H and I below.

Table H time (seconds) 100:0 80:20 60+40 40:60 20:80 0:100o 　oo　oooo.

30 96.10 98.98 89.66 28.09 0.68 2.42 60 99.29 101.36 98.62 47.16 3.74 2.4 290 99.65 99.69 99.66 57.53 5.78 1.0 4120 99.65 100.34 100.00 64.55 6.12 2.08180 99.29 99.32 99.31 69.90 9.18 2.08300 100.35 100.34 99.31 75.25 1 0.88 1.38a) Coated on silicon wafer, soaked at 25°C for 18 hours. Futobaked 75STPCDP/25STTPE (weight) b) Weight % solution time (seconds) 100:0 80:20 60:40 40:60 20:80 0:100o 　oo　oooo.

30 96.10 59.52 -2.00 -5.35 -0.33 1.0 060 99.29 98.96 54.00 10.37 -3.92 1. 0090 99.65 99.65 85.00 46.82 3.92 0. 33120 99.65 100.35 95.00 74.25 7.52 0J3180 99.29 99.65 9g, 67 87.96 16.99 0.33a) Coated on silicon wafer, softbaked for 18 hours at 25°C. 75STPCDP/25STTPE (weight) b) wt% solution time (seconds) 100:0 80:20 60:40 40:60 20:80 0:100o 　oo　oooo.

30 2.56 10.84 3.73 -2.69 -2.60 -1.86 60 3.66 15.38 10.45 -0.38 -1.49 -1.1 290 7.69 17.83 14.18 3.85 -2.97 0.00 120 12.09 18.53 18.66 3.85 -0.74 -1. 12180 13.19 20.98 1g, 66 6.54 -0.37 1 ．． 86300 14.65 23.08 27.99 11.54 10.04 0.00a) Coated on silicon wafer, softbaked for 18 hours at 25℃ Cured for 3 minutes in a 300 watt mercury vapor lamp with quartz/water filter. 50STPCDP150STTPE (weight) b) Weight % solution table time (seconds) Bu I Establishment Terukari Satoru Aiming o　oo　oooo.

30 2.56 1.13 0.00 -0.39 0.00 -0.3760 3.66 2.26 1.84 2.33 1.57 0.0090 7.6 9 3.02 1.84 -0.39 0!9 0.00120 12.09 3.40 2.94 1.95 1.18' 0.00180 13.19 7 ．． 55 2.94 1.95 0.78 0.00300 14.65 10. 94 2.94 3.11 3.14 0.00a) Coating on silicon wafer , soft baked at 25°C for 18 hours, 300 watts with quartz/water filter 50STPCDP150STTPE, cured for 3 minutes in a mercury vapor lamp. (Weight) b) Weight % solution In Tables J and K, only soft baking was performed and no curing by UV irradiation was performed. The results of M can be compared with the table below.

appearance time (seconds) 100:0 80:20 60:40 40:60 20:80 0:1003 0 97.03 102.24 95.47 37.36 -1.57 -2. 1460 100.74 99.63 98.87 65.66 3.54 0 ．． 0090 101.12 99.63 99.62 73.58 5.12 -0.71120 100.37 99.25 99.25 80.75 7. 48 -1.42180 101.12 98.88 98.11 83.40 10.24 -3.20300 101.12 98.88 101.13 87.55 15.75 -0.71a) Coated on silicon wafer, heated to 25℃ 50STPCDP150STTPE (weight ) b) wt % solution time (seconds) 100:Oso:2o 60:40 40:60 20:80 0:100o oo　oooo.

30 97.03 99.25 -3.18 -3.04 0.35 -0.7 160 100.74 103.02 39.93 -0.38 0.70 - 1.7990 101.12 101.51 91.87 14.45 5.6 1 -0.71120 100.37 102.64 9g, 94 56.27 12.98 0.00180 101.12 104.15 98.23 8 0.23 20.70 0.00300 101.12 103.77 99. 29 92.02 35.09 -0J6a) Coating on silicon wafer, 25 50STPCDP150STTPE soft-baked for 18 hours at ℃ Weight) b) Weight % solution Example 20 50% 5TPCDP (Example 6) and 50% 5TTPE (Example 6) in toluene 9) A series of solutions with seeds ranging from 46.0% solids to 58.4% solids by weight were prepared using various concentrations. These solutions are applied to the silicon substrate (surface) at a rate of 700 to 1 Spin coating for 60 seconds using a spin coating speed of 500 rpm: 25°C under vacuum. Soft bake for 24 hours. The sample is then tested with the USAF test pattern. 3 for UV irradiation with a 300 Watt mercury vapor lamp using a quartz/water filter. Exposure was made for a minute. The photocured polymer was then cured with toluene for 1 min at 25°C. Developed. The air-dried board was cured under vacuum for 1 hour at 25°C to 220°C. Hard bake using a heat exchanger and maintained at 220°C for 2.5 hours, then cooled to room temperature. did. The film thickness of the photocurable polymer was determined by Taylor-Hobson Ta1. Analysis was performed using a ysurf 10 profilometer. The table below shows the obtained results. Indicates film thickness.

Table N 505TPCDP/505TTPE Viscosity Film thickness μm) Solid content Pin painting speed (rpm) (mPa s) 700 1000 150046.0 6.0 5.3 4. 4 4.248.9 10.0 7.5 6.3 4.753.5 16.0 10.5 8.2 6.85 8.4 32.0 --- 12.9 10.9 ( a) Dissolved solids in toluene Example 21 Using 5TPCDP of Example 6 and 5TTPE of Example 9, 50 A 56 wt % solids solution of 50% 5TTPE and 50% 5TTPE was prepared. This melt The solution was applied to the silicon substrate (surface) using a spin coating speed of 600 to 200 Orpm. Spin coating for 0 seconds: soft bake at 25° C. for 24 hours under vacuum. sump 300W using the USAF test pattern and quartz/water filter. It was exposed to UV radiation from a mercury vapor lamp for 3 minutes. The light-cured polymer is then treated. Developed with luene for 1 minute at 25°C. Air-dried board at 25℃~21℃ Hard bake to 219°C using a 1 hour vacuum curing cycle with a 9°C lamp. It was maintained for 2.5 hours and then cooled to room temperature. Film thickness of photocurable polymer The side wall angle is 5loan Technology Corporation Analysis was performed using a ktak3030 profilometer. This data is shown in the table below. To summarize.

Table G Spin speed Film thickness Sidewall angle (rpm) (μm) 600 13, 5 19 600 13, 5 20 700 12, 0 35 700 12, 0 30 800 12, 3 33 800 11.2 21 800 11, 3 35 800 12, 0 18 1000 10, 3 24 1000 10, 5 28 1000 10, 0 33 1000 11, 2 26 1500 8, 5 22 1500 8, 8 30 1500 9, 2 26 1500 12, 4 18 2000 7, 5 25 2000 7゜79 2000 7, 9 37 2000 8, 0 20 Example 22 50% 5TPCDP (Example 6) and 50% 5TTPE (Example 6) in toluene 9) A series of solutions with seeds ranging from 46.0% solids to 58.4% solids by weight were prepared using various concentrations. These solutions are applied to the silicon substrate (surface) at a rate of 700 to 1 Spin coating for 60 seconds using a spin coating speed of 500 rpm; at 25°C under vacuum. Soft bake for 24 hours. The sample is then tested with the USAF test pattern. 3 for UV irradiation with a 300 Watt mercury vapor lamp using a quartz/water filter. Exposure was made for a minute. The photocured polymer was then cured with toluene for 1 min at 25°C. Developed for a while. The air-dried board was cured under vacuum for 1 hour at 25°C to 220°C. hard bake using a vacuum cleaner and maintain at 220°C for 2.5 hours, then cool to room temperature. Rejected. The sample was then metallized by ion beam sputtering. A metal film with a thickness of 5,000 to 1000 mm was obtained.

Adhesion by calibrated “Scotch tape adhesion test before and after thermal shock cycling” evaluated the power. The thermal shock cycle was performed by thermal cycling the sample at 55°C for 1 time. 0 min hold; rapid ramp from -55°C to 125°C; 10 min hold at 125°C included nothing. In the table below, the ratios listed are for all squares out of 25 squares of metal. This means that the material was not removed by the tape. In other words, 5/25 is gold This means that 20 squares of the genus have been removed.

Adhesive force measurement results Before cycling 2.51b, 10.01b, 2.51b, 10.01b, 2.51b, 10. 01b.

Chrome 0/25 bus Chrome 0/25 bus Copper 0/25 bus Copper O/25 ／＜S Aluminum 1/25 0/1 pass bus Aluminum 0/25 Nogusu Fri 6/25 6/6 a a a bus Gold 0725 Nokusu Nickel O/25 bus Nickel 0/25 bus (a) No sample evaluation (b) Tape evaluation example 23 in lb for 1/2 inch width tape The 5TPCDP resin of Example 5 and the 5TTPE resin of Example 9 were dissolved in toluene. 28.0% of 5TPCDP, 28.0% of 5TTPE, and 44% by weight of toluene. A solution having a composition of (50:50STPCDP:5TTPE) was obtained. This melt Apply the solution to an alumina or silicon substrate (surface) using a spin coating speed of 11,000 rpm. spin coated for 60 seconds; soft baked at 60° C. for 1 hour under nitrogen. this The polymer was then cured using a 3 hour 25°C to 220°C lamp nitrogen curing cycle. hard bake at 220°C for 2.0 hours, then heat to 220°C to 25°C for 4 hours. It was heated to ℃.

Adhesion by calibrated “Scotch tape adhesion test before and after thermal shock cycling” evaluated the power. The thermal shock cycle was performed by thermal cycling the sample at 55°C for 1 time. Sudden ramp from 55°C to 125°C maintained for 0 minutes; maintained substrate at 125°C for 10 minutes Before thermal shock cycling After 92 cycles 2.5 10.0 2.5 10.0 Alumina 0/25 pass -1---- Silicon 0/25 pass -1--- Example 24 The 5TPCDP resin of Example 5 and the 5TTPE resin of Example 9 were dissolved in toluene. 28.0% of 5TPCDP, 28.0% of 5TTPE, and 44% by weight of toluene. A solution having a composition of (50:50STPCDP:5TTPE) was obtained. This melt Apply the solution to an alumina or silicon substrate (surface) using a spin coating speed of 1100 Orp. spin coated for 60 seconds; soft baked at 60° C. for 1 hour under nitrogen. this The polymer was then cured using a 3 hour 25°C to 220°C lamp nitrogen curing cycle. hard bake at 220°C for 2.0 hours, then heat to 220°C to 25°C for 4 hours. It was heated to ℃.

Adhesion by calibrated “Scotch tape adhesion test before and after thermal shock cycling” evaluated the power. The thermal shock cycle was performed by thermal cycling the sample at 55°C for 1 time. Hold for 0 minutes; Rapid ramp from -55℃ to 125℃: Hold for 10 minutes at 125℃ Substrate Before thermal shock cycling After 92 cycles 2.5 10.0 2.5 10.0 1b, lb, Ib, lb.

Chrome 25/25 25/25 a a pass bus Nickel O/25 pass (b)------- Copper 0/25 pass (b)------ − Aluminum 0/25 pass (b)------ Gold 0/25 pass (b)-1 -----a) No sample evaluation b) Damage at polymer/metal interface In Examples 22-24 above, chromium adheres particularly well to the dielectric polymer and therefore serves as a suitable base for copper layers to form conductive patterns in multilevel structures. can be done.

Procedural amendment written Month 1, 1994

Claims (1)

[Claims] 1. A method of forming a polymer in a predetermined pattern on a substrate, the method comprising: (a) a structure; ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, ▲There are mathematical formulas, chemical formulas, tables, etc.▼; ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ R1, R2=H or alkyl having 1 to 10 carbon atoms; R3=methyl; R4=H; ▲There are mathematical formulas, chemical formulas, tables, etc.▼, alkyl moiety with 1 to 10 carbon atoms, 5 carbon atoms ~10 cycloalkyl moieties, or benzyl, provided that at least of all A 50% is vinylbenzyl moiety; L=Br or Cl; a=0, 1 or 2; b=0 or 1; m, n, s and t are 0 or integers, m+n+s+t=z is an integer from 1 to 10 is; R5=H, alkyl moiety having 1 to 10 carbon atoms, halogen or alkoxy moiety, or a monovalent aromatic radical] is an ether of the reaction product of dicyclopentadiene and phenol, shown as (b) applying the applied prepolymer of (a) to the substrate; - is irradiated through the shielding pattern to selectively cure the irradiated parts of the coating film. and (c) selectively dissolving the non-irradiated portions of the prepolymer coating film of (a). (d) heating the crosslinked portion of the prepolymer coating at a temperature within the range of 100°C to 300°C; temperature to further crosslink the crosslinked coating and transform the prepolymer into an infusible glassy and curing by heating for a sufficient period of time to convert it into a solid. Law. 2. In a method of forming a polymer in a predetermined pattern on a substrate, (a) the following elements ; (1) Formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, ▲There are mathematical formulas, chemical formulas, tables, etc.▼; ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ R1, R2=H or alkyl having 1 to 10 carbon atoms; R3=methyl; R4=H; ▲There are mathematical formulas, chemical formulas, tables, etc.▼, alkyl moiety with 1 to 10 carbon atoms, 5 carbon atoms ~10 cycloalkyl moieties, or benzyl; L=Br or Cl; a=0, 1 or 2; b=0 or 1; m, n, s and t are 0 or integers, m+n+s+t=z is an integer from 1 to 10 is; R5=H, alkyl moiety having 1 to 10 carbon atoms, halogen or alkoxy moiety, or a monovalent aromatic radical] The ether of the reaction product of dicyclopentadiene and phenol, shown as ( 2) (a) 1 molar proportion of dialdehyde, (b) about 3 to about 4 molar proportion of phenol; is an ether of the oligomeric condensation product of dialdehyde having the formula: OHC(CH2 ) rCHO (in the formula, r = 0 or an integer of 1 to 6), cyclopentanedialdehyde, Phthalaldehyde, isophthalaldehyde, terephthalaldehyde, hexahyde Loftaldehyde, cycloheptane dialdehyde, hexahydroisophthala hexahydroterephthalaldehyde and cyclooctanedialdehyde selected from the group consisting of, the phenol has the structure R6C6H4, and R6 is hydrogen or is an alkyl group having 1 to about 10 carbon atoms, and the phenol of the oligomer condensation product is The residue is vinylbenzyl, an alkyl moiety having 1 to 10 carbon atoms, or a cylinder having 5 to 10 carbon atoms. one or more randomly selected from the group consisting of chloroalkyl moiety and benzyl etherified by a substituent to form an ether moiety, in this case vinyl base ethers in which the ratio of ether to other moieties is from 1:1 to about 6:1. (b) applying the prepolymer mixture of (a) to the substrate; The irradiated prepolymer is irradiated through the shielding pattern to expose the irradiated coating area. selectively curing; (c) selecting non-irradiated areas of the prepolymer coating of (a); selectively dissolving; (d) the crosslinked portion of the prepolymer coating film at 100°C to 300°C; The crosslinked coating is further crosslinked at a temperature in the range of A process that hardens by heating for a sufficient time to convert it into a fusible glassy solid. A method that includes moderation. 3. The method according to claim 1 or 2, wherein R1 and R2 are hydrogen. 4. 3. The method according to claim 1 or 2, wherein z is 3 or 4. 5. 3. A method according to claim 1 or 2, wherein A is para-vinylbennzyl. 6. 3. The method according to claim 1 or 2, wherein L is Br. 7. Claim 1 or 2, wherein 70% of A is vinylbenzyl and the remainder is propyl. The method described in. 8. The dialdehyde is OHC(CH2)CHO, and r is 0 or an integer from 1 to 6. 3. The method of claim 2. 9. 3. The method according to claim 2, wherein R6 is hydrogen or methyl. 10. The ether moiety of condensation product (2) is approximately 70% vinylbenzyl and 30% 3. The method according to claim 2, wherein propyl is used. 11. The method according to claim 2, wherein the condensation product (2) has a molecular weight of 400 to 6,000. . 12. An electronic comprising a cured polymer produced by the method according to claim 1 or 2. Engineering intermediate connection structure. 13. 13. The electronic device of claim 12, wherein the cured polymer is attached to a chromium metal layer. Engineering intermediate connection structure.