Light-sensitive negative polymer composition

FIELD: physics.

SUBSTANCE: disclosed is a light-sensitive negative polymer composition comprising (a) an epoxy group-containing compound, (b) a first onium salt containing a structure of a cationic part of formula (b1) , and a structure of an anionic part of formula (b2) , and (c) a second onium salt containing a structure of a cationic part of formula (c1) , and a structure of an anionic part of formula (c2) . The invention also discloses a thin structure obtained from said composition and a method for making said thin structure, as well as a liquid ejector head in which said thin structure is used.

EFFECT: composition reduces variability and provides excellent reproducibility of a three-dimensional shape when using a photolithographic process.

11 cl, 5 dwg, 1 tbl, 12 ex

 

The technical field to which the invention relates.

The present invention relates to a negative photosensitive polymer composition and, in particular, to a light-sensitive negative resin composition suitable for the formation of the fine structure photolithographic method.

The level of technology

As the technology of micromachining there is a known photolithographic technology, in which the negative photosensitive polymer is subjected to exposure and manifestation with the formation of pattern and structure. This technology is used in a wide variety of applications, for example in the production of semiconductor circuits, in the production of templates for semiconductor exposure, and in the production of a variety of MEMS. As for the example application in the production of MEMS, such application is distributed on a variety of small sensors, microprobes, thin-film magnetic heads, crassostreae of the recording head, and so on Projection device (stepper) using i-line as the source of radiation is widely used as an apparatus for carrying out the exposure. In the field of this technology in recent years, the need to manufacture, has a more complex and miniature structure, and thus, there is a demand for the development is the negative photosensitive polymer, capable of forming a fine structure having a high accuracy to the light coming from the radiation source through the photomask.

Patent document 1 describes, as an example, a negative photosensitive polymer, a photosensitive polymer composition containing a multifunctional epoxy resin and initiator of cationic polymerization.

Patent document 2 describes, as an exemplary ink-jet head used in the production of MEMS, device containing a nozzle for ink-jet head, and the specified device ejects a drop of ink through contact with the air bubble generated by heating thermistor.

The list of references

Patent documents

Patent document 1: Japanese laid patent application No. 2008-256980

Patent document 2: Japanese laid patent application No. H04-10940

The invention

Technical problem

However, the above-described composition may in some cases have insufficient properties in the following respect. As an example, when a complex shape, for example, in a liquid ejection device with ejector hole having a narrowed shape, is formed from a negative photosensitive polymer using i-line as the source of the emission is, taper ejector holes may vary in the plate or substrate, resulting in some cases it becomes impossible to achieve the desired reproducibility.

The present invention is made to solve the above problems, and its objective is to offer a negative photosensitive polymer composition which provides less variability and the excellent reproducibility of three-dimensional form when using a photolithographic process.

Solution

To solve the above problem, the present invention offers a negative photosensitive polymer composition containing:

(a) containing an epoxy group connection

(b) first Onyewu salt containing the structure of the cation part represented by the formula (b1), and the structure of the anion portion represented by the formula (b2), and

(c) second oneway salt containing the structure of the cation part represented by formula (c1), and the structure of the anion portion represented by formula (c2),

in which R1-R3represent, independently from each other an organic group which may be substituted and has 1 to 30 carbon atoms, with the proviso that at least two atoms of oxygen contained in all make up what their atoms, R 1-R3X is selected from carbon atom, nitrogen atom, phosphorus atom, boron atom and an atom of antimony, Y is chosen from-S(=O)2-, alcelaphinae group, -OCF2-, -C(=O)-CF2-, -O-C(=O)-CF2-, -C(=O)-O-CF2- and a single bond, R4represents a hydrocarbon group which may be substituted by a fluorine atom and contains from 1 to 30 carbon atoms, and m and n are such that the sum m + n is 3, and n is an integer selected from 0, 1 and 2, when X represents a carbon atom, the sum of m + n is 2, and n is an integer selected from 0 and 1 when X is a nitrogen atom, the sum of m + n is 6 and n is an integer selected from 0 to 6 when X is an atom of phosphorus or antimony, or the sum of m + n is 4, and n represents an integer selected from 0 to 3 when X is an atom of boron,

in which R5-R7represent, independently from each other an organic group which may be substituted and has 1 to 15 carbon atoms, with the proviso that not more than one oxygen atom is contained in all components of the atoms R5-R7Z is selected from a carbon atom and sulfur atom, k is 1 when Z is a carbon atom, k is 2 when Z is an atom series is, and R8represents a hydrocarbon group which may contain a heteroatom and contains from 1 to 20 carbon atoms.

The technical result of the invention

When using the negative photosensitive polymer composition according to the present invention, fine structure, which provides less variability and the excellent reproducibility of three-dimensional form, can stably be formed by using a photolithographic process. In particular, the negative photosensitive polymer composition according to the present invention provides excellent reproducibility when using a photolithographic process using i-line.

The following distinctive features of the present invention become apparent from the following description of exemplary embodiments when considering the accompanying drawings.

Brief description of drawings

[Fig. 1] Fig. 1 is a typical perspective view illustrating the construction of an exemplary liquid ejection head.

[Fig. 2] Fig. 2 schematically illustrates the substrate containing the generating power of the elements.

[Fig. 3A, 3B, 3C, 3D, 3E and 3F] Fig. 3A, 3B, 3C, 3D, 3E and 3F are schematic process drawings illustrating an exemplary method of forming fine patterns using the receiving light-sensitive negative resin composition according to option implementation.

[Fig. 4A, 4B, 4C, 4D, 4E and 4F] Fig. 4A, 4B, 4C, 4D, 4E and 4F are schematic process drawings illustrating another exemplary method of forming fine patterns using a negative photosensitive polymer composition according to option implementation.

[Fig. 5] Fig. 5 is a schematic view of a cross section of a liquid ejection head, illustrating the taper.

Description of embodiments

Next, the negative photosensitive polymer composition according to the present invention will be described in detail.

(a) Containing an epoxy group connection

There is no particular limitation, which applies to containing an epoxy group compound (hereinafter in this document is abbreviated as "component (a)"). However, this connection is preferably a multifunctional epoxy polymer compound capable of epoxy polymerization and containing a number of epoxy groups in its molecule. Examples of such multifunctional epoxy polymer include multifunctional epoxy polymers, alicyclic type, multifunctional epoxy polymer type phenol novolacs, multifunctional epoxy polymer type orthocresol of novolaks, megafunction the global epoxy type polymers triphenylene of novolaks and multifunctional epoxy polymer type bisphenolic And novolaks. Among them, preferably used is a multifunctional epoxy polymer type bisphenola And novolak, multifunctional alicyclic epoxy polymer type or multifunctional epoxy polymer type phenol novolak. In them the number of functional groups is preferably five or more. For example, it is preferable to use EPIKOTE 157S70 (product of Japan Epoxy Polymer Co., Ltd.), EPICLON N-865 (a product of DIC Corporation), and EHPE 3150 (product of Daicel Corporation) are commercially available products.

There is no particular limitation, which applies to the softening temperature of containing an epoxy group connection. However, its softening temperature is preferably 50°C or more, preferably 60°C or more. The softening temperature is preferably 180°C or less, preferably 160°C or less.

Number containing epoxy groups of the compounds in the solid mass of the negative photosensitive resin composition is preferably 40 wt.% or more, preferably 60 wt.% or more, more preferably 65 wt.% or more. This amount is preferably about 99.9 wt.% or less, preferably of 99.2 wt.% or less. When applying such a composition to the substrate is formed of a resistive layer having a high senses the activity and the corresponding hardness.

(b) First onieva salt

first onieva salt (hereinafter in this document is abbreviated as "component (b)") is a combination of the structure of the cation part represented by the formula (b1), and the structure of the anion portion represented by the formula (b2)in a ratio of 1:1.

In the structure of the cation part represented by the formula (b1), R1-R3represent, independently from each other an organic group which may be substituted and has 1 to 30 carbon atoms, with the proviso that at least two atoms of oxygen contained in all components of the atoms R1-R3.

In the structure of the anion portion represented by the formula (b2), X is selected from carbon atom, nitrogen atom, phosphorus atom, boron atom and an atom of antimony, Y is chosen from-S(=O)2-, alcelaphinae group, -OCF2-, -C(=O)-CF2-, -O-C(=O)-CF2-, -C(=O)-O-CF2- and a single bond, R4represents a hydrocarbon group which may be substituted by a fluorine atom and contains from 1 to 30 carbon atoms, and m and n are such that the sum m + n is 3, and n is an integer selected from 0, 1 and 2, when X represents a carbon atom, the sum of m + n is 2, and n is an integer selected from 0 and 1 when X is a nitrogen atom, the sum of m + n is is 6, and n is an integer selected from 0 to 6 when X is an atom of phosphorus or antimony, or the sum of m + n is 4, and n represents an integer selected from 0 to 3 when X is a boron atom.

Examples of (b1) and (b2). A distinctive feature of the structure of the cation part represented by the formula (b1), is that the sensitivity to the i-line is high, because the absorption wavelength of the component (b) can be increased due to the fact that it contains at least two atoms of oxygen. On the other hand, the structure of the anion portion represented by the formula (b2), is decomposed component (b1) after exposure, forming acid derived from structure (b2). After that, the reaction of the cationic polymerization of epoxy groups containing an epoxy group connection, you can initiate and accelerate due to the action of the generated acid. The resulting acid is preferably an acid of such strength that contains an epoxy group compound is cured sufficiently. The strength of acid, which contains an epoxy group compound cures sufficiently, means that the acid is an acid having a strength of not lower than geksaftorpropena acid, according to theory of Lewis acids (Lewis), i.e. that the function of the acidity of Gamete (Hammett) -HO is 18 or more. According to theory of acids Branstad (Brønsted), a strong acid means that the acid is an acid having a strength of not lower than nanoformulation, i.e. that its pKa value is -3,57 or more.

Preferred specific examples of the structure of the cation part represented by the formula (b1)below.

Among them, examples containing cyclic carbonyl structure are preferred from the point of view that they have a high sensitivity to i-line, and examples R1-R3containing cyclic carbonyl structure, include the above-mentioned (b1-17)-(b1-30). R1-R3preferably containing heterocyclic group containing a cyclic carbonyl structure, and specific examples R1-R3containing heterocyclic group containing a cyclic carbonyl structure, include the above-mentioned (b1-17)-(b1-24). At least one of R1-R3preferably contains cyclic carbonyl structure, and preferably two or more groups of R1-R3contain cyclic carbonyl structure. Carbonyl group prisutstvie the em in the dual system, and this greatly increases the absorption wavelength of the first oneway salt (b), and conjugated system contains an aromatic ring, resulting in a particularly increases the sensitivity to i-line.

In the structure of the cation part represented by the formula (b1), it is necessary only the content of the at least two atoms of oxygen in all parts of the atoms R1-R3as described above, with one or two groups of R1-R3may have a structure in which is not contained in either one oxygen atom. Examples of structures that can take R1-R3described below. In the structure of the cation part represented by the formula (b1), each group of R1-R3represents, for example, the aryl group containing a total of from 6 to 30 carbon atoms, a heterocyclic group containing a total of from 4 to 30 carbon atoms, the alkyl group containing a total of from 1 to 30 carbon atoms, alkenylphenol group containing a total of from 2 to 30 carbon atoms, or alkylamino group containing a total of from 2 to 30 carbon atoms. These groups can contain, as substituents, at least one selected from the group which consists of, for example, the corresponding groups, including alkyl groups, hydroxyl group, cycloalkyl group, alkeline GRU is dust, alkyline group, CNS group, alkylcarboxylic group, arylcarbamoyl group, alkoxycarbonyl group, aryloxyalkyl group, aristoteleion group, alloctype, aristocraty, allylthiourea, aryl groups containing heteroatoms, aromatic ring group, alloctype, alkylsulfonyl group, arylsulfonyl group, alkylsulfonyl group, arylsulfonyl group, accelerometry, amino group, cyano and nitro-group, and halogen atoms. More specifically, examples of these substituents include the corresponding groups of the alkyl groups (e.g. methyl, ethyl, sawn, ISO-propyl and butylene group containing from 1 to 6 carbon atoms, hydroxyl group, cycloalkyl group (for example, cyclopropyl, cyclobutyl, cyclopentyl and tsiklogeksilnogo group)containing from 3 to 6 carbon atoms, alkeline group (for example, vinyl, 1-propylene, 2-propylene and 2-butenolide group)containing from 2 to 6 carbon atoms, alkyline group (for example, acetylenyl, 1-propenylidene, 2-propenylidene and 2-butonline group)containing from 2 to 6 carbon atoms, CNS group (for example, metaxylene, amoxilina, n-propoxy, isopropoxide, n-butoxyl and tert-butoxyl group containing from 1 to atomov carbon acylcarnitine group containing from 2 to 6 carbon atoms, arylcarbamoyl group containing from 7 to 11 carbon atoms, alkoxycarbonyl group (for example, methoxycarbonyl, ethoxycarbonyl and tert-butoxycarbonyl group)containing from 2 to 6 carbon atoms, aryloxyalkyl group containing from 7 to 11 carbon atoms, aristoteleion group containing from 7 to 11 carbon atoms, alloctype containing from 2 to 6 carbon atoms, aristocraty (for example, phenylthiourea and naphthylthiourea)containing from 6 to 10 carbon atoms, allylthiourea (for example, methylthio-ethylthio, h-propylthio, isopropylthio, h-butylthio - and tert-butylthiourea)containing from 1 to 6 carbon atoms, aryl groups (e.g. phenyl, raftiline and antarctilyne group containing from 6 to 14 carbon atoms containing heteroatoms aromatic ring group (for example, foreline and thienyl groups containing from 4 to 8 carbon atoms, azlocillin group (for example, phenoxyl and nafoxidine group containing from 6 to 10 carbon atoms, alkylsulfonyl group containing from 1 to 6 carbon atoms, arylsulfonyl group containing from 6 to 10 carbon atoms, alkylsulfonyl group containing from 1 to 6 carbon atoms, arylsulfonyl group containing from 6 to 10 carbon atoms etkilenecegini group, containing from 1 to 6 carbon atoms, amino group, ceanography and nitro and halogen atoms (for example, chlorine atoms, bromine and fluorine). R1-R3can be the same or different from each other. Two or more R groups of R1-R3can also be connected to each other directly or via-O-, -S-, -SO-, -SO2-, -NH-, -NRa-, -CO-, -C(=O)O-, -C(=O)NH-, alkylamino group containing from 1 to 3 carbon atoms or fenelonov group, forming a ring structure. Here, Ra represents an alkyl group containing from 1 to 5 carbon atoms, or aryl group containing from 6 to 10 carbon atoms. In particular, in this application the alkyl group contains a linear chain, branched chain or cyclic chain.

Preferred specific examples of the anionic structure part represented by the formula (b2), are listed below.

In the structure of the anion portion represented by the formula (b2), R4preferably represents a hydrocarbon group containing at least one fluorine atom, and when n is 0, and Y represents-S(=O)2- or a single bond. When m is 2 or more, any one carbon atom of the group R4and any carbon atom of another group, R4can also be connected to each other through a single bond, forming colorevolution. R4represents, for example, alkyl or aryl group, which contains as a substituent a fluorine atom.

In the structure of the anion portion represented by the formula (b2), X preferably represents a phosphorus atom, and specific examples of such patterns include the above-mentioned formula (b2-11)-(b2-18). In the case of Lewis acid, i.e., in the case where X is an atom of antimony or phosphorus, the resulting cured film generally has excellent thermal stability. In the case where X represents a phosphorus atom, a tendency to corrosion of the metal is lower than in the case where X is an atom of antimony.

As component (b) you can use a single component or a combination of two or more components.

The content of component (b) is preferably 0.01 mass. hours or more, preferably 0.1 mass. hours or more per 100 mass. including negative photosensitive polymer composition. This content is preferably 20 mass. hours or less, preferably 10 mass. hours or less.

(C) Second onieva salt

Second onieva salt (hereinafter in this document is abbreviated as "component (c)") is a combination of specific structures, including the structure of the cation part represented by formula (c1) and the structure of the anionic part, represented by formula (c2), in a 1:1 ratio.

In the structure of the cation part represented by formula (c1), R5-R7represent, independently from each other an organic group which may be substituted and has 1 to 15 carbon atoms, with the proviso that not more than one oxygen atom is contained in all components of the atoms R5-R7.

In the structure of the anion portion represented by formula (c2), Z is selected from a carbon atom and sulfur atom. k is 1 when Z is a carbon atom, or k is 2 when Z is a sulfur atom. R8represents a hydrocarbon group which may contain a heteroatom and contains from 1 to 20 carbon atoms.

In the present invention, it is important the content of the second oneway salt (c) in addition to the first oneway salt (b). The reason for this is as follows. As described above, the acid (b2)formed from the first oneway salt (b) after exposure to i-line, is a strong acid, which initiates and accelerates the reaction of the cationic polymerization of epoxy groups, and, thus, the component (b) is appropriate for photosensitization in this case. On the other hand, when the acid (b2) diffuses into the negative photosensitive polymer composition cures her n the exposed part, which turns into the ejector hole, and thus, in some cases, it may be difficult education ejector holes. Thus, in the present invention using the second oneway Sol (c), which constitute the structure of the cation part represented by formula (c1), and the structure of the anion portion represented by formula (c2). In particular, assuming the acid with a proton attached to the structure of the anion portion represented by formula (c2), the structure of the anion portion represented by formula (c2), this structure represents a weak acid, which cannot initiate epoxy polymerization, or has a very low acidity, to initiate polymerization. Accordingly, when the acid (b2)formed from the first oneway salt (b), reacts with the second oneway salt (c), is salt metabolism, and acid turns into a weak acid, which cannot initiate epoxy polymerization, or it difficult to initiate polymerization. In other words, the second onieva salt (c) can function as a good absorber acid, which accelerates the polymerization of epoxides in epoxy polymerization. A distinctive feature of the structure of the cation part represented by formula (c1), is that the sensitivity to the i-line is low, in the later patterns, which includes not more than one atom of oxygen contained in all components of the atoms R5-R7. In the inhibition can occur sensitization second oneway salt (c) in relation to light during an exposure. As described above, the first onieva salt and the second onieva salt act synergistically in the present invention, the result of which can stably form a thin structure, which provides less variability and the excellent reproducibility of three-dimensional forms.

The following are examples of (c1) and (c2).

In the structure of the cation part represented by formula (c1), each group of R5-R7represents, for example, the aryl group containing a total of from 6 to 15 carbon atoms, or alkyl group containing a total of from 1 to 15 carbon atoms. These groups can contain, as substituents, at least one Deputy, selected from the group which consists of, for example, the corresponding groups, including alkyl groups, alkyl fluoride group, a hydroxyl group, cycloalkyl group, CNS group, alkylcarboxylic group, arylcarbamoyl group, aristocraty, allylthiourea, aryl group and azlocillin groups, and halogen atoms. More specifically, examples of these substituents include the indicate the respective groups, including alkyl groups (e.g. methyl, ethyl, sawn, ISO-propyl and butylene group containing from 1 to 6 carbon atoms, alkyl fluoride group (for example, triptoreline and panafcortelone group containing from 1 to 6 carbon atoms, hydroxyl group, cycloalkyl group (for example, cyclopropyl, cyclobutyl, cyclopentyl and tsiklogeksilnogo group)containing from 3 to 6 carbon atoms, CNS group (for example, metaxylene, amoxilina, n-propoxyphene, isopropoxide, n-butoxyl and tert-butoxyl group containing from 1 to 6 carbon atoms, alkylcarboxylic group containing from 2 to 6 carbon atoms, arylcarbamoyl group containing from 7 to 11 carbon atoms, aristocraty (for example, phenylthiourea and naphthylthiourea)containing from 6 to 10 carbon atoms, allylthiourea (for example, methylthio, ethylthio, h-propylthio, isopropylthio, h-butylthio - and tert-butylthiourea)containing from 1 to 6 carbon atoms, aryl groups (e.g. phenyl and raftiline group containing from 6 to 10 carbon atoms and azlocillin group (for example, phenoxyl and nafoxidine group containing from 6 to 10 carbon atoms, and halogen atoms (for example, chlorine atoms, bromine and fluorine). R5-R7can be the same or different from each other. Two or more gr of the PP R of R 5-R7can also connect to each other directly or through alkylenes group containing from 1 to 3 carbon atoms, or fenelonov group, forming a ring structure.

Preferred specific examples of the structure of the cation part represented by formula (c1)shown below.

In the structure of the anion portion represented by formula (c2), R8represents, for example, alkyl group containing a total of from 1 to 20 carbon atoms, or aryl group containing a total of from 6 to 20 carbon atoms. These groups may contain substituents, including at least one Deputy, selected from the group which consists of, for example, alkyl groups, oxoprop, cycloalkyl group, CNS group and acylcarnitine group. More specifically, examples of these substituents include alkyl groups (e.g. methyl, ethyl, sawn, ISO-propyl and butylene group)containing 1 to 10 carbon atoms, cycloalkyl group (for example, cyclopropyl, cyclobutyl, cyclopentyl and tsiklogeksilnogo group)containing from 3 to 6 carbon atoms, CNS group (for example, metaxylene, amoxilina, n-propoxyphene, isopropoxide, n-butoxyl and tert-butoxyl group containing from 1 to 6 carbon atoms, the alkyl is ebonyline group, containing from 2 to 6 carbon atoms. Two or more carbon atoms, R8can also connect to each other directly or through alkylenes group containing from 1 to 3 carbon atoms forming a ring structure. The ring structure may be monocyclic or polycyclic.

Preferred specific examples of the anionic structure part represented by formula (c2)below.

In the structure of the anion portion represented by formula (c2), R8preferably represents-containing aromatic hydrocarbon or alicyclic hydrocarbon structure. When R8represents the containing aromatic hydrocarbon or alicyclic hydrocarbon structure, it is inhibited, due to their volume and carbon density, so that the acid released from the anion represented by the formula (c2), evaporates in the process of heating and goes into the surrounding atmosphere. Specific examples of the structure of anion part containing the group R8containing an aromatic hydrocarbon or alicyclic hydrocarbon, include the above-mentioned structures (c2-1)-(c2-11), (c2-17)-(c2-25), (c2-28)-(c2-40), and (c2-48)-(c2-56).

In the structure of the anion portion represented by formula (c2), Z preferably represents the volume of sulfur. When Z is a sulfur atom, the anion may be more stable as compared to the case where Z represents a carbon atom. Thus, the nucleophilicity of the anion part can be inhibited, which prevents the decomposition of the second oneway salt, called anionic part, nucleophile attacking cationic part (c1).

As component (c) you can use a single component or a combination of two or more components.

The content of component (c) is preferably 0.001 mass. hours or more per 100 mass. including negative photosensitive polymer composition. This content is preferably 5 mass. hours or less, preferably 4 mass. hours or less.

The amount of component (b) and component (c)entered in the negative photosensitive polymer composition, preferably satisfy the following ratio: the number of moles of the first oneway salt (b) > number of moles of the second oneway salt (c).

When this ratio is executed, it creates a condition in which the quantity of the component (b)constituting the acid, which initiates an epoxy polymerization is more than the amount of the component (c), functioning as a shock absorber, and as a result, it is possible to achieve high photosensitivity.

Both components are also preferably meet Aut following relationship: [the number of moles of the first oneway salt (b)] × 0,7 > the number of moles of the second oneway salt (c) > [the number of moles of the first oneway salt (b)] × 0,02.

The number of added second oneway salt (c) is increased to make the number of moles of the second oneway salt (c) in excess of [the number of moles of the first oneway salt (b)] × 0,02, and as a result, it is possible to sufficiently achieve the effect of the second oneway salt as a shock absorber.

The photosensitive negative resin composition according to the present invention may also contain third oneway salt in addition to the first oneway salt (b) and the second oneway salt (c). Examples of third oneway salt include compounds containing the structure of the cation part represented by formula (c1), and the structure of the anion portion represented by the formula (b2). In this case, the content of any third oneway salt is preferably, for example, 0.001 mass. hours or more, preferably 0.005 mass. hours or more per 100 mass. including negative photosensitive polymer composition. This content is preferably 25 mass. hours or less, preferably 15 mass. hours or less.

As described above, when using the negative photosensitive polymer composition according to the present invention can stably form a thin structure, which provides less variability and the excellent reproducibility of the three the agreement form. The photosensitive negative resin composition according to the present invention provides excellent reproducibility, in particular, when using a photolithographic process using i-line.

In some cases, as a shock absorber for acid can be used containing the nitrogen atoms of the organic compound, in particular aminosilicone. However, when such containing an epoxy group compound, which is used in the present invention, is mixed with aminoguanidinium, aminosidine functions as a hardener, and curing may occur in some cases during the dark reactions. Thus, it appears difficult storage of amino compounds in a state of mixing with such containing an epoxy group compound used in the present invention, for an extended period of time. On the other hand, component (c) according to the present invention produces extremely weak dark reactions even when it is mixed with containing an epoxy group compound, thus, it becomes possible to store the component (c) in the state of mixing with such containing an epoxy group compound used in the present invention, for an extended period of time.

A method of manufacturing

For example, the liquid ejection head can be produced using the negative photosensitive polymer composition according to the present invention. There is no particular limitation, which applies to the liquid ejection head. However, as the example mentioned Crassostrea recording head.

Fig. 1 is a typical perspective view illustrating the construction of an exemplary ink-jet recording head. Crassostrea recording head illustrated in Fig. 1 has a duct forming layer 4, which forms the ejection openings of the ink (ejection holes) 5 and the duct of the ink (liquid channels) 3c in connection with ejection holes 5 for the paint to the substrate, contains many energy producing elements 2. Applying paint hole (feed paint the hole) 6, which delivers the ink (liquid) in the duct paint 3c, is provided in the substrate 1. As is illustrated in Fig. 2, many energy producing element 2 is located at the specified step on the substrate 1.

Next, a method of manufacturing ink-jet recording head will be described with reference to Fig. 3A-3F and Fig. 4A-4F. Fig. 3A-3F and Fig. 4A-4F correspond to the sectional views along the line 3-3 in Fig. 1 and 2. In particular, methods of manufacture, illustrated in Fig. 3A-3F Fig. 4A-4F, referred to as "manufacturing method 1 and method of manufacture 2", respectively.

In particular, the input control signal electrode (not illustrated in the drawings) to control element attached to each productive energy item 2.

A method of manufacturing a 1

At first make the substrate 1 containing the generating power of the elements 2, as illustrated in Fig. 3A.

The substrate 1 is preferably a silicon substrate, particularly preferably single crystal silicon. When the substrate 1 is made a through hole by anisotropic etching, the substrate preferably is a single crystal silicon having a crystal orientation <100>. When the through hole is made in the substrate 1 by dry etching, sandblasting or laser processing, the substrate may be a silicon single crystal having a crystal orientation <110>.

There is no particular limitation, which applies to generating power elements 2, with the proviso that the energy of the electrons for the production of ink droplets can be passed to the paint for the release of ink droplets from the ejection openings. For example, when temperature resistant elements are used as the energy producing elements, temperature resistant the element is provided heats present near the paint, forcing thereby the paint to change state to produce ejection energy.

Soluble polymer composition is then applied to the substrate 1, forming soluble polymer layer 3a for drawing duct paints, as illustrated in Fig. 3B.

As a method of forming soluble polymer layer 3a, for example, a positive photosensitive polymer is properly dissolved in the solvent, and the solution is applied on a substrate 1 using the centrifuge cover.

After that, the applied solution is heated, and as a result can form soluble polymer layer 3a. There is no particular limitation, which applies to the thickness of the soluble polymer layer 3a, with the proviso that it corresponds to the desired height of the duct paint. However, this thickness is preferably, for example, from 2 to 50 microns.

Soluble polymer layer 3a is then treated with radiation and exercise, resulting in a pattern duct paint 3b, as illustrated in Fig. 3C.

Photosensitive negative polymer composition according to the present invention is then applied to the drawing duct paint 3b and the substrate 1, receiving duct forming layer 4.

The thickness of the duct forming layer 4 is preferably 2 μm or bol is e, taking into account the thickness of the duct figure paint 3b. There is no particular limitation, which applies to the upper limit of this thickness. However, this upper limit is, for example, 100 μm or less, taking into account the thickness of the duct figure paint 3b, in order to ensure the possibility of parts of the ejector holes for paint.

Forming a duct layer 4 is then irradiated with i-line and show, using methyl isobutyl ketone (MIBK)to carry out image forming processing. After this process by washing with isopropyl alcohol (IPA), resulting in ejection holes 5 for the paint (Fig. 3D).

The Central wavelength of i-line is 365 nm.

Applying paint hole 6 is then made using an appropriate method, such as etching processing, as illustrated in Fig. 3E.

Figure flow of paint 3b is then dissolved in an appropriate solvent, as illustrated in Fig. 3F.

The solvent can be used, for example, an aqueous alkali solution or an organic solvent.

After that, the substrate 1 is cut and divided into plates using a saw for cutting semiconductor wafers, and form an electrical connection for actuating the energy producing elements 2. In addition, the plate is CNY reservoir element attached to complete the ink-jet recording head.

In particular, the above-described method is also useful as an image forming method for producing hollow images, without limitation of the method of manufacturing the ink-jet recording head.

A method of manufacturing 2

First soluble polymer composition applied to the substrate 1, receiving drawing duct paint 3b, as illustrated in Fig. 4A.

Forming a duct layer 4 formed by the photosensitive negative resin composition according to the present invention, then made the figure of a duct paint 3b and the substrate 1, as illustrated in Fig. 4B.

Forming a duct layer 4 is then irradiated with i-line through a first photomask 10, as illustrated in Fig. 4C. When after the first exposure carry out the sintering of this duct forming layer formed surface of the recess 7 and the first drawings of the injection holes 8a, which are hidden image ejector holes. There is no particular limitation, which applies to the conditions of sintering after the first exposure. However, this sintering represents, for example, heat treatment for 4 minutes at 100°C.

Forming a duct layer 4 then irradiated with i-line through a second photomask 11, as illustrated in Fig. 4D. The second photomask 1 contains part of the hole, different from the first photomask 10. In this case, at least a portion of the unexposed parts after the first exposure were subjected to the second exposure. When after the second exposure carry out the sintering for a given duct forming layer, the newly formed second drawings ejector holes 8b, which are hidden image ejector holes. There is no particular limitation, which applies to the conditions of sintering after the second exposure. However, this sintering represents, for example, heat treatment for 4 minutes at 90°C.

The second photomask 11 includes a round or oval light shielding portion corresponding to the ejection hole for education ejector holes. On the other hand, the first photomask 10 includes a light shielding parts in the same positions as the light shielding part for ejecting holes of the second photomask 11, and each of these light shielding parts has an area greater than the area of the second photomask 11 to close the light shielding portion of the second photomask 11.

Forming a duct layer 4 then show, using methyl isobutyl ketone (MIBK). In addition, the process by washing with isopropyl alcohol (IPA), resulting in ejection openings 5 how about illyustrirovano in Fig. 4E.

Applying paint hole 6 is then made using an appropriate method, such as etching processing, as illustrated in Fig. 4F. After this drawing duct paint 3b is dissolved in an appropriate solvent, forming a duct paint 3c.

After that, the substrate 1 is cut and divided into plates using a saw for cutting semiconductor wafers, and form an electrical connection for actuating the energy producing elements 2. In addition, laminar reservoir element attached to complete the ink-jet recording head.

In particular, the above-described method is also useful as an image forming method for producing hollow images, without limitation of the method of manufacturing the ink-jet recording head.

EXAMPLES

Hereinafter the present invention will be described by way of examples. However, the present invention is not limited to these examples.

Example 1

Components (a), (b) and (c) were mixed according to the composition shown in table 1, and then onomatology ether of propylene glycol as a solvent were introduced into the mixture in an amount of 80 mass. including 100 mass. including the component (a), to obtain a negative photosensitive polymer composition. Units in table 1 represent the mass part.

P the following this negative photosensitive polymer composition was applied on a substrate, representing a silicon plate using the device for centrifugal coating; pre-sintering and drying was carried out for 5 minutes at 90°C to obtain a layer of photosensitive polymer composition, having a thickness of 40 μm. After the preliminary sintering was carried out by forming an image exposure through a pattern, which was produced by the desired picture, using the stepper FPA-3000 i5+ with i-line (manufacturer Canon Inc.), according to the above manufacturing method 1 and method of manufacture 2 and after exposure were processed by sintering for 4 minutes at 90°C on a hot plate.

In particular, in the manufacturing method 1, the thickness of the duct forming layer 4 obtained from the photosensitive negative resin composition was restricted to 20 μm taking into account the thickness of the duct figure paint 3b. In the manufacturing method 2, the thickness of the duct forming layer 4 obtained from the photosensitive negative resin composition, limited to 25 microns with regard to the thickness of the drawing duct paint 3b.

In the method of manufacturing 1 level of defocusing of the stepper i-line appropriately changed, and as a result it was possible to get the taper, comprising, for example, from about 0.1 to 10°. This example was carried out in such a way that the taper was 5° fashion production 1 and 10° in the manufacturing method 2. Then used a device for the display of CDS-860R+ (manufacturer Canon Inc.), to make manifest processing. Polymer pattern after development was specaly together with the substrate for 1 hour at 140°C using a furnace, to obtain a cured pattern of resist on the substrate.

Assessment

Component 90° taper 9, illustrated in Fig. 5, was calculated based on pictures of the cross section obtained by observation using a scanning electron microscope (SEM) in the direction of the section view along the line 3-3 in Fig. 1 or 2. The measurement was performed on each of the five injection holes of the same figure. The percentage is determined by calculating the difference between the average of the five obtained values of the taper, the choice of values, the most different from the average, calculated by dividing the difference by the mean and multiplying the result by 100, defined as the variability of the taper.

Examples 2-6 and 8

The photosensitive negative resin composition was produced in the same manner as in example 1, except that components (a), (b) and (c) used in accordance with their respective compositions shown in table 1, and was evaluated.

Example 7

Photosensitive negative polymer composition was produced in the same manner as in example 1, except t the th, components (a), (b), (c) and (d) used according to the composition shown in table 1, and were evaluated. Component (d) is such that the structure of the cationic part represents the following compound denoted by c1-21, and the structure of the anionic part is a b2-23.

(c1-21)

Example 9

Photosensitive negative polymer composition was produced in the same manner as in example 1 except that components (a), (b) and (c) and the sensitizer used according to the composition shown in table 1, and were evaluated. As the sensitizer (e-1 used 1-naphthol.

Comparative examples 1 and 2

The photosensitive negative resin composition was produced in the same manner as in example 1, except that components (a) and (d) used in accordance with their respective compositions shown in table 1, and was evaluated.

Comparative example 3

Photosensitive negative polymer composition was produced in the same manner as in example 1, except that components (a) and (b) used according to the composition shown in table 1, and was evaluated.

In particular, all the examples 1-9 and comparative example 3 satisfy the relation: the number of moles of the first oneway salt > number of malastare oneway salt.

Table 1
Mixed componentsExampleComparative example
123456789123
Component (a)a-1100--100100----100100100
a-2-100100--100- -----
a-3------100100100---
Component (b)b1-17/b2-1122----121--2
b1-18/b2-12--2---------
b1-25/b2-11---2--------
b1-1/b2-1----5-------
b1-17/b2-23-----3------
Component (c)c1-1/c2-10,5--- --0,5-----
c1-2/c2-2-0,5-----0.5----
c1-5/c2-7--0,5---------
c1-13/c2-8---0,5------- -
c1-2/c2-6----0,5-------
c1-1/c2-26-----0,5------
c1-19/c2-14--------0,25
Component (d)c1-21/b2-23--- ---4--33-
The sensitizere-1--------0,10---
Variability taperA method of manufacturing 13%-4%3%5%--4%6%12%-15%
A method of manufacturing 2-2%--- 4%2%-5%-10%-

(a-1): EPICLON N-865 (trade name, product of DIC Corporation)

(a-2): JER157S70 (trade name, product of Japan Epoxy Polymer Co., Ltd.)

(a-3): EHPE 3150 (trade name, product of Daicel Corporation).

In examples 1-9 corresponding photosensitive negative resin composition containing the components (b) and (c), to determine the variability taper ejector holes. As a result, the variability was 5% or less, and, therefore, was achieved with a high reproducibility.

On the other hand, in the negative photosensitive polymer compositions of comparative examples 1-3 variability taper ranged from 10% to 15%, and thus the reproducibility of the taper was insufficient.

Industrial applicability

As described above, the photosensitive negative resin composition according to the present invention is capable of producing taper with good results, and can stably form a fine structure, which provides less dispersion and excellent reproducibility of three-dimensional forms. Accordingly, the photosensitive negative resin composition according to astasia invention can appropriately be used in a variety of devices, subjected to the microprocessing for MEMS.

Although the present invention is described in relation to exemplary embodiments, it should be understood that the present invention is not limited to the described exemplary embodiments of the implementation. The volume of the following claims should be interpreted in the widest possible sense, therefore, to include all such modifications and equivalent structures and functions.

The present application claims the priority of Japanese patent application No. 2010-280474, filed December 16, 2010, which is in its entirety incorporated herein by this reference.

For a list of symbols

1 - Substrate

2 - Producing energy

3a - Soluble polymer layer

3b is a drawing duct paint

3c - Duct paint

4 - duct Forming layer

5 - Ejecting holes

6 - Feed paint hole

7 - Surface cavities

8a - First drawings ejector holes

8b - Second drawings ejector holes

9 is a taper Angle of 90°

10 - the First photomask

11 - Second photomask

1. The photosensitive negative resin composition containing:
(a) containing an epoxy group connection,
(b) first Onyewu salt containing the structure of the cation part represented by the formula (b1), and the structure of the anion of the second part, represented by the formula (b2), and
(c) second oneway salt containing the structure of the cation part represented by formula (c1), and the structure of the anion portion represented by formula (c2),

in which R1-R3represent, independently from each other an organic group which may be substituted and has 1 to 30 carbon atoms, with the proviso that at least two atoms of oxygen contained in all components of the atoms R1-R3X is selected from carbon atom, nitrogen atom, phosphorus atom, boron atom and an atom of antimony, Y is chosen from-S(=O)2-, alcelaphinae group, -OCF2-, -C(=O)-CF2-, -O-C(=O)-CF2-, -C(=O)-O-CF2- and a single bond, R4represents a hydrocarbon group which may be substituted by a fluorine atom and contains from 1 to 30 carbon atoms, and m and n are such that the sum m + n is 3, and n is an integer selected from 0, 1 and 2, when X represents a carbon atom; the sum of m + n is 2, and n is an integer selected from 0 and 1, when X represents a nitrogen atom; the sum of m + n is 6 and n is an integer selected from 0 to 6 when X is an atom of phosphorus or antimony; or the sum of m + n is 4, and n represents an integer selected from 0 to 3 when X, not only is em a boron atom;

in which R5-R7represent, independently from each other an organic group which may be substituted and has 1 to 15 carbon atoms, with the proviso that not more than one oxygen atom is contained in all components of the atoms R5-R7Z is selected from a carbon atom and sulfur atom; k is 1 when Z is a carbon atom; k is 2 when Z is a sulfur atom; and R8represents a hydrocarbon group which may contain a heteroatom and contains from 1 to 20 carbon atoms.

2. The photosensitive negative resin composition according to p. 1, which corresponds to the ratio of [the number of moles of the first oneway salt] > [the number of moles of the second oneway salt].

3. The photosensitive negative resin composition according to p. 1, in which component (b) has a density, at least to i-line.

4. The photosensitive negative resin composition according to p. 1, in which at least one R1-R3contains cyclic carbonyl structure.

5. The photosensitive negative resin composition according to p. 1, in which R8contains aromatic hydrocarbon or alicyclic hydrocarbon.

6. The photosensitive negative resin composition according to p. 1, in which Z represents the Wallpaper a sulfur atom.

7. The photosensitive negative resin composition according to p. 2, which corresponds to the ratio of [the number of moles of the first oneway salt] x 0.7 > [the number of moles of the second oneway salt] > [the number of moles of the first oneway salt] x 0,02.

8. The photosensitive negative resin composition according to p. 1, in which X represents a phosphorus atom.

9. Fine structure formed on the substrate, which is a product of curing a photosensitive negative resin composition under item 1.

10. Liquid ejection head, including forming a duct layer formed by a thin structure on p. 9.

11. Method of forming fine patterns, comprising:
(1) the stage of applying the photosensitive negative resin composition according to p. 1 on a substrate, and
(2) the stage of exposure to negative photosensitive polymer composition forming the image processing by photolithography using i-line.



 

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7 cl, 14 dwg

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