Resin material

Abstract

To provide a resin material which can reduce a dielectric constant and a linear expansion coefficient.SOLUTION: A resin material contains a resin component, and a covalent organic structure, wherein the covalent organic structure has a negative linear expansion coefficient or a boron atom.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a resin material. [Background technology]

[0002] Conventionally, various resin materials have been used to obtain electronic components such as semiconductor devices, laminates, and printed wiring boards. For example, resin materials are used to form insulating layers in printed wiring boards. Resin materials are also used as semiconductor encapsulation materials. As the resin materials, film-like resin materials (resin films) and paste-like resin materials (resin pastes) have been used.

[0003] As the resin material, resin materials containing a resin component and an inorganic filler, as described in Patent Documents 1 and 2 below, are widely used.

[0004] Furthermore, Patent Document 3 listed below discloses a resin film formed from a resin composition containing a resin component and a covalent organic framework in which a plurality of linker moieties and a plurality of multidentate core moieties are linked by covalent bonds. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent Publication No. 2021-119245 [Patent Document 2] Japanese Patent Application Laid-Open No. 2013-173841 [Patent Document 3] WO2023 / 203907A1 Summary of the Invention [Problem to be solved by the invention]

[0006] Devices capable of data communication in high frequency bands using 5G are being used. Furthermore, development of devices capable of data communication in even higher frequency bands is progressing. As frequencies increase, there is a demand for resin materials that can lower the dielectric constant.

[0007] Furthermore, in recent years, substrates have become larger and thinner, making them more susceptible to warping. One of the causes of substrate warping is internal stress generated by the difference in thermal expansion coefficient between the substrate and the resin material. From the viewpoint of suppressing substrate warping, it is preferable that the resin material has a small linear expansion coefficient.

[0008] However, there is generally a trade-off between lowering the dielectric constant and lowering the linear expansion coefficient. For example, when a resin material containing an inorganic filler is used, the linear expansion coefficient can be lowered to some extent, but it is difficult to lower the dielectric constant. Furthermore, it is difficult to lower the linear expansion coefficient with a resin material formulated to lower the dielectric constant. Therefore, with conventional resin materials, it is difficult to lower the dielectric constant and the linear expansion coefficient at the same time.

[0009] An object of the present invention is to provide a resin material that can reduce the dielectric constant and the linear expansion coefficient. [Means for solving the problem]

[0010] The present specification discloses the following resin materials.

[0011] Item 1. A resin material comprising a resin component and a covalent organic framework, wherein the covalent organic framework has a negative linear expansion coefficient or contains boron atoms.

[0012] Item 2. The resin material according to Item 1, wherein the covalent organic framework has a negative linear expansion coefficient.

[0013] Item 3. The resin material according to Item 1, wherein the covalent organic framework has a boron atom.

[0014] Item 4. The resin material according to Item 1, wherein the covalent organic framework has a negative linear expansion coefficient and contains boron atoms.

[0015] Item 5. The resin material according to any one of Items 1 to 4, wherein the resin component includes a thermosetting compound.

[0016] Item 6. The resin material according to any one of Items 1 to 5, wherein the resin component includes a thermosetting compound, and the glass transition temperature of a cured product of the thermosetting compound is 90°C or higher.

[0017] Item 7. The resin material according to any one of Items 1 to 6, wherein the resin component includes a thermosetting compound, and the glass transition temperature of a cured product of the thermosetting compound is 140°C or higher.

[0018] Item 8. The resin material according to any one of Items 1 to 7, wherein the resin component contains a thermosetting compound, and the glass transition temperature of a cured product of the thermosetting compound is 300°C or lower.

[0019] Item 9. The resin material according to any one of Items 1 to 8, wherein the resin component includes a thermosetting compound, and the glass transition temperature of a cured product of the thermosetting compound is 140°C or higher and 300°C or lower.

[0020] Item 10. The resin material according to any one of Items 1 to 9, wherein the resin component includes a thermoplastic resin.

[0021] Item 11. The resin material according to any one of Items 1 to 10, wherein the resin component contains a thermoplastic resin having a glass transition temperature of 90°C or higher.

[0022] Item 12. The resin material according to any one of Items 1 to 11, wherein the resin component contains a thermoplastic resin, and the thermoplastic resin has a glass transition temperature of 140° C. or higher.

[0023] Item 13. The resin material according to any one of Items 1 to 12, wherein the resin component contains a thermoplastic resin, and the thermoplastic resin has a glass transition temperature of 300° C. or lower.

[0024] Item 14. The resin material according to any one of Items 1 to 13, wherein the resin component contains a thermoplastic resin, and the thermoplastic resin has a glass transition temperature of 140°C or higher and 300°C or lower.

[0025] Item 15. The resin material according to any one of Items 1 to 14, wherein the resin component contains a thermoplastic resin, and the melting point of the thermoplastic resin is 300° C. or lower.

[0026] Item 16. The resin material according to any one of Items 1 to 15, wherein the resin component includes a thermosetting compound and a thermoplastic resin.

[0027] Item 17. The resin material according to any one of Items 1 to 16, wherein the resin component contains a thermosetting compound and a thermoplastic resin, and the melting point of the thermoplastic resin is 300°C or less.

[0028] Item 18. The resin material according to any one of Items 1 to 17, wherein the resin material has a water absorption rate of 1% by weight or less.

[0029] Item 19. The resin material according to any one of items 1 to 18, which is a resin paste.

[0030] Item 20. The resin material according to any one of items 1 to 18, which is a resin film.

[0031] Item 21. The resin material according to any one of Items 1 to 20, which is used to form an insulating layer in a printed wiring board.

[0032] Item 22. The resin material according to any one of Items 1 to 20, which is used to form a molding resin in which a semiconductor chip is embedded in a semiconductor device.

[0033] Item 23. The resin material according to any one of Items 1 to 20, which is used for joining optical components in optical communications or optical information processing devices.

[0034] Item 24. The resin material according to any one of Items 1 to 20, which is used to bond components in electronic device components. [Effects of the Invention]

[0035] The resin material according to the present invention includes a resin component and a covalent organic framework. In the resin material according to the present invention, the covalent organic framework has a negative linear expansion coefficient or contains boron atoms. Since the resin material according to the present invention has the above-described configuration, it is possible to lower the dielectric constant and reduce the linear expansion coefficient. [Brief explanation of the drawings]

[0036] [Figure 1] FIG. 1 is a cross-sectional view schematically showing a multilayer printed wiring board using a resin material according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0037] The present invention will be described in detail below.

[0038] (resin material) The resin material according to the present invention includes a resin component and a covalent organic framework. In the resin material according to the present invention, the covalent organic framework has a negative linear expansion coefficient or has boron atoms. The covalent organic framework may have a negative linear expansion coefficient or may have boron atoms. The covalent organic framework may have a negative linear expansion coefficient and may have boron atoms.

[0039] The resin material according to the present invention has the above-described structure, and therefore can have a low dielectric constant and a low linear expansion coefficient.

[0040] The resin material according to the present invention may be a resin composition or a resin film. The resin composition has fluidity. The resin composition may be in a paste form. The paste form includes a liquid form. Therefore, the resin material according to the present invention may be a resin paste.

[0041] The resin paste is in a paste state at 25°C.

[0042] The viscosity of the resin paste at 25°C is preferably 0.001 Pa·s or more, more preferably 0.01 Pa·s or more, even more preferably 0.1 Pa·s or more, and preferably 10,000 Pa·s or less, more preferably 1,000 Pa·s or less, even more preferably 200 Pa·s or less.

[0043] The viscosity of the resin paste at 25° C. can be measured using, for example, an E-type viscometer ("TVE22L" manufactured by Toki Sangyo Co., Ltd.) under conditions of 25° C. and 5 rpm.

[0044] The thickness of the resin film is preferably 1 μm or more, more preferably 10 μm or more, and is preferably 200 μm or less, more preferably 100 μm or less.

[0045] The resin material may be a thermosetting resin material or a thermoplastic resin material. When the resin material is a resin film, the resin film may be a thermosetting resin film or a thermoplastic resin film. When the resin material is a resin film, the resin film may be a B-stage film.

[0046] The B-stage film is a film in a semi-cured state, which means that the B-stage film is not completely cured and can continue to be cured.

[0047] Below, we will explain the details of each component used in the resin material according to the present invention, as well as the uses of the resin material according to the present invention. In the following explanation, "100% by weight of the components in the resin material excluding the solvent" means 100% by weight of the components in the resin material excluding the solvent if the resin material contains a solvent, and means 100% by weight of the resin material if the resin material does not contain a solvent. "100% by weight of the components in the resin material excluding the solvent" means 100% by weight of the non-volatile components in the resin material.

[0048] [Resin component] The resin material includes a resin component. The resin component is different from the covalent organic framework. The resin component is different from the resin contained in the component blended as a filler in the resin material.

[0049] Examples of the resin component include a thermosetting compound, a curing agent, a curing accelerator, a thermoplastic resin, etc. The resin component may be used alone or in combination of two or more.

[0050] The resin component preferably contains a thermosetting compound, and also preferably contains a thermoplastic resin. The resin component may be a thermosetting compound, a thermosetting compound and a curing agent, a thermosetting compound and a curing accelerator, a thermosetting compound, a curing agent and a curing accelerator, or a thermoplastic resin. The resin component preferably contains a thermosetting compound or a thermoplastic resin, and more preferably contains a thermosetting compound and a thermoplastic resin. The resin component may not contain a thermosetting compound, may not contain a curing agent, may not contain a curing accelerator, or may not contain a thermoplastic resin.

[0051] The content of the resin component in 100% by weight of the components excluding the solvent in the resin material is preferably 10% by weight or more, more preferably 20% by weight or more, and preferably 95% by weight or less, more preferably 90% by weight or less, and even more preferably 80% by weight or less. When the content of the resin component is equal to or more than the above lower limit and equal to or less than the above upper limit, the linear expansion coefficient of the resin material can be further reduced.

[0052] <Thermosetting compounds> The resin component preferably includes a thermosetting compound.The resin material preferably includes a thermosetting compound.

[0053] Examples of the thermosetting compound include epoxy compounds, imide compounds, maleimide compounds, styrene compounds, phenoxy compounds, oxetane compounds, polyarylate compounds, diallyl phthalate compounds, episulfide compounds, (meth)acrylic compounds, amino compounds, triazine compounds, unsaturated polyester compounds, phenyl ether compounds, crosslinked polyolefin compounds, crosslinked polycycloolefin compounds, and silicone compounds. The thermosetting compounds may be used alone or in combination of two or more.

[0054] The thermosetting compound preferably contains an epoxy compound, a maleimide compound, a triazine compound, or a phenyl ether compound, and more preferably contains an epoxy compound or a maleimide compound, in which case the effects of the present invention can be more effectively exhibited.

[0055] Examples of the epoxy compound include bisphenol A type epoxy compounds, bisphenol F type epoxy compounds, bisphenol S type epoxy compounds, phenol novolac type epoxy compounds, biphenyl type epoxy compounds, biphenyl novolac type epoxy compounds, biphenol type epoxy compounds, naphthalene type epoxy compounds, fluorene type epoxy compounds, phenol aralkyl type epoxy compounds, naphthol aralkyl type epoxy compounds, dicyclopentadiene type epoxy compounds, anthracene type epoxy compounds, epoxy compounds having an adamantane skeleton, epoxy compounds having a tricyclodecane skeleton, naphthylene ether type epoxy compounds, and epoxy compounds having a triazine nucleus in the skeleton. Only one of the above epoxy compounds may be used, or two or more may be used in combination.

[0056] Examples of the maleimide compound include N-phenylmaleimide and N-alkylbismaleimide. The maleimide compound may be a bismaleimide compound. The maleimide compounds may be used alone or in combination of two or more.

[0057] The thermosetting compound preferably contains a thermosetting compound that is liquid at 25°C. In this case, the mixability of the resin component and the covalent organic framework can be further improved, thereby further improving the uniformity of performance. It is also preferable that the epoxy compound contains the thermosetting compound that is liquid at 25°C, and it is also preferable that the maleimide compound contains the thermosetting compound that is liquid at 25°C.

[0058] The viscosity at 25°C of the thermosetting compound that is liquid at 25°C is preferably 10,000 mPa·s or less, and more preferably 5,000 mPa·s or less.

[0059] The viscosity of the thermosetting compound can be measured using, for example, a dynamic viscoelasticity measuring device ("VAR-100" manufactured by Rheologica Instruments).

[0060] The glass transition temperature of the cured product of the thermosetting compound is preferably 50° C. or higher, more preferably 90° C. or higher, even more preferably 100° C. or higher, particularly preferably 140° C. or higher, and preferably 300° C. or lower, more preferably 290° C. or lower, and even more preferably 280° C. or lower. When the glass transition temperature is equal to or higher than the lower limit and equal to or lower than the upper limit, residual stress is likely to be reduced, and warping and cracking of the substrate, etc. can be effectively suppressed.

[0061] The glass transition temperature of the cured product of the thermosetting compound can be determined by DSC (differential scanning calorimetry) in accordance with JIS K 7121. Specifically, it can be determined as follows.

[0062] The thermosetting compound is cured (thermosetting) to obtain a cured product of the thermosetting compound. The obtained cured product of the thermosetting compound is heated from room temperature (25°C) to a temperature approximately 30°C higher than the predicted glass transition temperature of the cured product at a temperature increase rate of 10°C / min, and maintained at that temperature for 10 minutes. The cured product of the thermosetting compound is then rapidly cooled to a temperature approximately 50°C lower than the predicted glass transition temperature of the cured product. Next, the cured product of the thermosetting compound is heated at a temperature increase rate of 10°C / min to a temperature approximately 30°C higher than the predicted glass transition temperature of the cured product. In this way, a DSC curve of the cured product of the thermosetting compound is obtained. The glass transition temperature of the cured product of the thermosetting compound is determined by the intersection of the obtained DSC curve with an imaginary horizontal line equidistant along the vertical axis from a line extending the low-temperature baseline and a line extending the high-temperature baseline.

[0063] The content of the thermosetting compound in the resin material (100% by weight, excluding the solvent) is preferably 5% by weight or more, more preferably 10% by weight or more, and preferably 95% by weight or less, more preferably 90% by weight or less, and even more preferably 80% by weight or less. When the content of the thermosetting compound is equal to or more than the lower limit and equal to or less than the upper limit, the effects of the present invention can be more effectively exhibited.

[0064] <Curing agent> The resin component may or may not contain a curing agent. The resin material may or may not contain a curing agent. When the resin component contains a thermosetting compound, it is preferable that the resin component contains a curing agent.

[0065] The curing agent is appropriately selected depending on the type of thermosetting compound. Examples of the curing agent include active ester compounds, amine compounds, phenol compounds, cyanate ester compounds, benzoxazine compounds, carbodiimide compounds, thiol compounds, phosphine compounds, dicyandiamide, and acid anhydrides. Only one type of the curing agent may be used, or two or more types may be used in combination.

[0066] The content of the curing agent in the resin material is appropriately selected depending on the type and content of the thermosetting compound. In the resin material, the content of the curing agent per 100 parts by weight of the thermosetting compound is preferably 1 part by weight or more, more preferably 10 parts by weight or more, even more preferably 30 parts by weight or more, preferably 200 parts by weight or less, more preferably 140 parts by weight or less. When the content of the curing agent is equal to or more than the lower limit and equal to or less than the upper limit, the curability can be further improved.

[0067] <Curing accelerator> The resin component may or may not contain a curing accelerator. The resin material may or may not contain a curing accelerator. When the resin component contains a thermosetting compound, it is preferable that the resin component contains a curing accelerator. The use of the curing accelerator further increases the curing rate.

[0068] The curing accelerator is appropriately selected depending on the type of thermosetting compound. Examples of the curing accelerator include anionic curing accelerators such as imidazole compounds, cationic curing accelerators such as amine compounds, curing accelerators other than anionic and cationic curing accelerators such as phosphorus compounds and organometallic compounds, and radical curing accelerators such as peroxides. Only one type of the curing accelerator may be used, or two or more types may be used in combination.

[0069] The content of the curing accelerator in the resin material is appropriately selected depending on the type and content of the thermosetting compound. In the resin material, the content of the curing accelerator per 100 parts by weight of the thermosetting compound is preferably 0.01 parts by weight or more, more preferably 0.5 parts by weight or more, preferably 5 parts by weight or less, more preferably 3 parts by weight or less. When the content of the curing accelerator is above the lower limit and below the upper limit, the resin material is cured efficiently. Furthermore, when the content of the curing accelerator is above the lower limit and below the upper limit, the storage stability of the resin material is further improved, and a better cured product is obtained.

[0070] <Thermoplastic resin> The resin component preferably includes a thermoplastic resin.The resin material preferably includes a thermoplastic resin.

[0071] Examples of the thermoplastic resin include polyvinyl acetal resin, polyimide resin, polyphenylene ether resin, cyclic polyolefin resin, polycarbonate resin, methacrylic resin, phenoxy resin, etc. The thermoplastic resin may be used alone or in combination of two or more.

[0072] From the viewpoint of effectively lowering the dielectric loss tangent and effectively increasing the adhesion of the metal wiring, the thermoplastic resin is preferably a polyimide resin or a phenoxy resin, and more preferably a phenoxy resin.

[0073] Examples of the phenoxy resin include phenoxy resins having a bisphenol A skeleton, phenoxy resins having a bisphenol F skeleton, phenoxy resins having a bisphenol S skeleton, phenoxy resins having a biphenyl skeleton, phenoxy resins having a novolac skeleton, phenoxy resins having a naphthalene skeleton, and phenoxy resins having an imide skeleton.

[0074] From the viewpoint of obtaining a resin material with even better storage stability, the weight average molecular weight of the thermoplastic resin is preferably 5,000 or more, more preferably 10,000 or more, and preferably 100,000 or less, more preferably 50,000 or less.

[0075] The weight average molecular weight of the thermoplastic resin is a weight average molecular weight measured by gel permeation chromatography (GPC) and calculated as polystyrene.

[0076] The melting point (Tm) of the thermoplastic resin is preferably 100° C. or higher, more preferably 150° C. or higher, even more preferably 200° C. or higher, and preferably 300° C. or lower, more preferably 280° C. or lower, and even more preferably 260° C. or lower. When the melting point of the thermoplastic resin is equal to or higher than the above lower limit and equal to or lower than the above upper limit, the mixability of the resin component and the covalent organic framework can be further improved, and therefore the uniformity of performance can be further improved.

[0077] The melting point (Tm) of the thermoplastic resin can be determined by DSC (differential scanning calorimetry) in accordance with JIS K 7121. Specifically, it can be determined by the following method (1) or (2). When the thermoplastic resin is a crystalline resin, the melting point of the thermoplastic resin is preferably determined by the following method (1).

[0078] (1) The thermoplastic resin is heated from room temperature (25°C) to a temperature approximately 30°C higher than the estimated melting point of the thermoplastic resin at a temperature increase rate of 10°C / min, and maintained at that temperature for 5 minutes. The thermoplastic resin is then cooled to a temperature approximately 50°C lower than the estimated melting point of the thermoplastic resin at a temperature decrease rate of 10°C / min. The thermoplastic resin is then heated to a temperature approximately 30°C higher than the estimated melting point of the thermoplastic resin at a temperature increase rate of 10°C / min. A DSC curve of the thermoplastic resin is thus obtained. The melting peak temperature of the obtained DSC curve is taken as the melting point of the thermoplastic resin.

[0079] (2) Approximately 5 mg of sample (thermoplastic resin) is placed in a dedicated aluminum container, and using a differential scanning calorimeter (e.g., PerkinElmer's "DSCPyris1" or "DSC7"), the temperature is increased from 30°C to 200°C at a rate of 320°C / min and held at 200°C for 5 minutes. The temperature is then decreased from 200°C to 30°C at a rate of 10°C / min and held at 30°C for 5 minutes. The melting point is then determined from the endothermic curve obtained when the temperature is increased at a rate of 10°C / min. If multiple peaks are detected during the measurement, the peak temperature detected at the highest temperature is defined as the melting point (Tm) of the thermoplastic resin.

[0080] The glass transition temperature of the thermoplastic resin is preferably 30°C or higher, more preferably 90°C or higher, even more preferably 100°C or higher, particularly preferably 140°C or higher, and preferably 300°C or lower, more preferably 280°C or lower. When the glass transition temperature is above the lower limit and below the upper limit, the heat resistance can be further improved and the dimensional stability can be further improved. Furthermore, when the glass transition temperature is above the lower limit and below the upper limit, warping and cracking of the substrate, etc. can be effectively suppressed.

[0081] The glass transition temperature of the thermoplastic resin can be determined by DSC (differential scanning calorimetry) in accordance with JIS K 7121. Specifically, the glass transition temperature of the thermoplastic resin can be determined in the same manner as the method for measuring the glass transition temperature of the cured product of the thermosetting compound described above.

[0082] The content of the thermoplastic resin in 100% by weight of the components excluding the solvent in the resin material is preferably 5% by weight or more, more preferably 10% by weight or more, and preferably 95% by weight or less, more preferably 90% by weight or less. When the content of the thermoplastic resin is equal to or more than the lower limit and equal to or less than the upper limit, the linear expansion coefficient of the resin material can be further reduced.

[0083] [Covalent organic structure] The resin material includes a covalent organic framework (COF). In the resin material, the COF is a filler. The COF is a porous crystalline particle in which organic structures are covalently bonded to each other to form a periodic structure. The COF is a particle, specifically a porous particle. By using the COF, which is a porous particle, the dielectric constant can be reduced. Furthermore, by using the COF, the linear expansion coefficient of the resin material can also be reduced.

[0084] Various COFs are known, as exemplified below.

[0085] COFs include COF-1, COF-5, COF-6, COF-8, COF-10, COF-102, COF-102-tolyl, COF-102-allyl, COF-102-C12, COF-103, COF-105, COF-108, COF-202, COF-11Å, COF-1 4Å, COF-16Å, COF-18Å, SCOF-1, PPy-COF, SCOF-3, BTP-COF, MCOF-1, TP-COF, DBA-3D-COF, HHTP-DPB, TPE-Ph-COF, COF-300, COF-301, SCOF-IC1, N-COF, DAAQ-TFP COF, COF-LZU1, SurfaceCOF 1+5 , RT-COF-1, NUS-15, TFPB-TAPB-COF, COF-BTA-DAB, COF-BTA-BZ, SIOC-COF-5, 3D-Py-COF, 4PE-1P-COF, HPB-COF, NTU-COF-1, DL-COF-1, sCOFB, CTF-1, BLP-2H, BBO-COF-1, and TriCF.

[0086] In addition to the above COFs, examples of the COF include those described in "Adv. Funct. Mater. (2018), 28, 1705553," "COMMUNICATIONS CHEMISTRY (2018) 1:98," "Green Energy & Environment 8 (2023) 1596," "Molecules (2017), 22, 1149," "Membranes (2023), 13, 696," and "Chem. Rev. (2020), 120, 8814." Furthermore, examples of the COF include those described in documents other than these documents.

[0087] Among various COFs, the present invention uses a COF having a negative linear expansion coefficient or containing boron atoms. Only one COF may be used, or two or more COFs may be used in combination.

[0088] The smaller the linear expansion coefficient of the COF, the better. The linear expansion coefficient of the COF is preferably 10 ppm / °C or less, more preferably 0 ppm / °C or less, even more preferably less than 0 ppm / °C, and particularly preferably -1 ppm / °C or less. When the linear expansion coefficient of the COF is equal to or less than the above upper limit (or less than the above upper limit), the linear expansion coefficient of the resin material can be further reduced. The linear expansion coefficient of the COF may be -10 ppm / °C or more.

[0089] The linear expansion coefficient of COF means the "average linear expansion coefficient at 0° C. or higher and 500° C. or lower." The linear expansion coefficient of COF can be measured as follows.

[0090] Powder X-ray diffraction measurement of the COF is performed while changing the temperature, and the lattice constant at each temperature is determined. When the change in lattice constant with respect to temperature is dL / dT and the lattice constant at the reference temperature is L, the linear expansion coefficient of the COF is calculated by the following formula (X):

[0091] Linear expansion coefficient of COF = (1 / L) × (dL / dT) (X)

[0092] In addition, when the lengths of the axes (α, β, γ) are different in the crystal structure of the COF, the linear expansion coefficient is calculated for each axis using the above formula (X), and the average value is taken as the linear expansion coefficient of the COF.

[0093] The COF may be a structure in which a plurality of linker moieties and a plurality of multidentate core moieties are linked by covalent bonds, or a structure in which compounds constituting a plurality of multidentate core moieties are linked by covalent bonds. In this case, the COF has a network-like molecular skeleton with numerous pores, thereby enabling the effects of the present invention to be exerted more effectively.

[0094] The covalent bond may be a single bond, a double bond, or a triple bond.

[0095] The COF may be a two-dimensional COF in which covalent bonds are connected in only two dimensions, or a three-dimensional COF in which covalent bonds are connected in three dimensions. From the viewpoint of isotropically reducing the thermal expansion of the resin material, the COF is preferably a three-dimensional COF.

[0096] The multidentate core moiety is an organic structural part located at a branching point of the mesh-like molecular skeleton of the COF, and the linker moiety is an organic structural part that connects the two multidentate core moieties located on both sides of the linker moiety.

[0097] Herein, the compound constituting the multidentate core portion is referred to as a "multidentate core compound." Herein, the compound constituting the linker portion is referred to as a "linker compound." Therefore, the multidentate core portion is a structural moiety derived from the multidentate core compound. The linker portion is a structural moiety derived from the linker compound.

[0098] Examples of the multidentate core compound and the linker compound include compounds represented by the following formulas (1) to (41). The multidentate core compound may be used alone or in combination of two or more. The linker compound may be used alone or in combination of two or more. Depending on the molecular skeleton of the COF, the same compound may function as both a multidentate core compound and a linker compound. In addition, a COF may be composed only of a multidentate core compound. That is, a COF may not have a linker moiety.

[0099] [ka]

[0100] In the above formula (1), n ​​represents an integer of 1 or more and 4 or less. In the above formula (1), n ​​may be 1, 2, 3, or 4.

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[0106] In the above formula (6), X represents a carbon atom or a silicon atom.

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[0108] In the above formula (7), R represents a tolyl group, an allyl group, or a group represented by the following formula (a):

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[0110] In the above formula (a), n represents an integer of 0 to 20, and * represents the bonding position to the carbon atom. When n is 0 in the above formula (a), the group represented by the above formula (a) is a methyl group.

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[0112] In the formula (8), R1 and R2 each represent a hydrogen atom or a group represented by the formula (a). In the formula (8), R1 may be a hydrogen atom and R2 may be a hydrogen atom, or R1 may be a hydrogen atom and R2 may be a group represented by the formula (a).

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[0117] In the formula (12), R1 and R2 each represent a hydrogen atom or a group represented by the formula (a). In the formula (12), R1 may be a hydrogen atom and R2 may be a hydrogen atom, or R1 may be a hydrogen atom and R2 may be a group represented by the formula (a).

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[0147] Tables 1 to 3 below show examples of combinations of types of COFs with multidentate core compounds and linker compounds.

[0148] [Table 1]

[0149] [Table 2]

[0150] [Table 3]

[0151] The COF preferably contains boron atoms. By using a COF containing boron atoms, the effects of the present invention can be more effectively achieved. Furthermore, by using a COF containing boron atoms, the flame retardancy of the resin material can be improved.

[0152] In a COF having a boron atom, the multidentate core moiety may have a boron atom, or the linker moiety may have a boron atom. In a COF having a boron atom, the multidentate core moiety may be a structural moiety derived from a multidentate core compound having a boron atom (a boron-atom-containing multidentate core compound). In a COF having a boron atom, the linker moiety may be a structural moiety derived from a linker compound having a boron atom (a boron-atom-containing linker compound).

[0153] Examples of COFs having a boron atom include COF-1, COF-5, COF-6, COF-8, COF-10, COF-102, COF-102-tolyl, COF-102-allyl, COF-102-C12, COF-103, COF-105, COF-108, COF-202, COF-11Å, COF-14Å, COF-16Å, COF-18Å, SCOF-1, PPy-COF, SCOF-3, BTP-COF, MCOF-1, TP-COF, DBA-3D-COF, HHTP-DPB, TPE-Ph-COF, NTU-COF-1, DL-COF-1, sCOFB, and BLP-2H.

[0154] The COF having a boron atom may be a boroxy-type COF, a boronate ester-type COF, or a borazine-type COF. In the COF having a boron atom, the covalent bond between the multidentate core moiety and the linker moiety does not necessarily have to be a boroxy-type, boronate ester-type, or borazine-type covalent bond. In the COF having a boron atom, for example, some of the covalent bonds may be imine-type or triazine-type covalent bonds.

[0155] COFs can be prepared by conventional methods, for example, by subjecting a multidentate core compound and a linker compound to a dehydration condensation reaction.

[0156] The COF content in the resin material, based on 100% by weight of components excluding the solvent, is preferably 5% by weight or more, more preferably 10% by weight or more, and preferably 95% by weight or less, more preferably 90% by weight or less. When the COF content is equal to or greater than the above lower limit and equal to or less than the above upper limit, the effects of the present invention can be more effectively exhibited. Furthermore, when the COF content is equal to or greater than the above lower limit and equal to or less than the above upper limit, the mixability of the resin component and the covalent organic framework can be further improved, thereby further improving the uniformity of performance.

[0157] The COF content is preferably 5% by volume or more, more preferably 10% by volume or more, and preferably 95% by volume or less, more preferably 90% by volume or less, based on 100% by volume of the components excluding the solvent in the resin material. When the COF content is equal to or greater than the above lower limit and equal to or less than the above upper limit, the effects of the present invention can be more effectively exhibited. Furthermore, when the COF content is equal to or greater than the above lower limit and equal to or less than the above upper limit, the mixability of the resin component and the covalent organic framework can be further improved, thereby further improving the uniformity of performance.

[0158] [solvent] The resin material contains or does not contain a solvent. The resin material optionally contains a solvent. The resin material may or may not contain a solvent. When the resin material is a resin paste, the resin material (resin paste) may or may not contain a solvent. When the resin material is a resin film, the resin material (resin film) may or may not contain a solvent. By using the solvent, the viscosity of the resin material can be controlled within a suitable range, and the coatability of the resin material can be improved. Only one type of the solvent may be used, or two or more types may be used in combination.

[0159] Examples of the solvent include acetone, methanol, ethanol, butanol, 2-propanol, 2-methoxyethanol, 2-ethoxyethanol, 1-methoxy-2-propanol, 2-acetoxy-1-methoxypropane, toluene, xylene, methyl ethyl ketone, N,N-dimethylformamide, methyl isobutyl ketone, N-methyl-pyrrolidone, n-hexane, cyclohexane, cyclohexanone, and naphtha, which is a mixture.

[0160] It is preferable that most of the solvent is removed before the resin material is used, and therefore the boiling point of the solvent is preferably 200°C or lower, more preferably 180°C or lower.

[0161] The content of the solvent in the resin material is not particularly limited.

[0162] When the resin material is a resin paste, the content of the solvent in 100% by weight of the resin paste is preferably 90% by weight or less, more preferably 50% by weight or less, and even more preferably 25% by weight or less. When the content of the solvent is below the upper limit, the amount of solvent remaining after curing of the resin material can be reduced, and the occurrence of voids can be effectively suppressed. Note that the content of the solvent in 100% by weight of the resin paste may be 0% by weight or more, or may be 1% by weight or more.

[0163] When the resin material is a resin film, the content of the solvent is preferably 90% by weight or less, more preferably 50% by weight or less, and even more preferably 25% by weight or less, based on 100% by weight of the resin film. When the content of the solvent is below the upper limit, the amount of solvent remaining after curing of the resin material can be reduced, and the occurrence of voids can be effectively suppressed. Note that the content of the solvent may be 0% by weight or more, or may be 1% by weight or more, based on 100% by weight of the resin film.

[0164] [Other ingredients] For the purpose of improving impact resistance, heat resistance, resin compatibility, workability, etc., the resin material may contain other components in addition to the above-mentioned components (resin component, COF, and solvent). Examples of such other components include inorganic fillers, organic fillers other than COF, leveling agents, flame retardants, coupling agents, colorants, antioxidants, UV inhibitors, antifoaming agents, thickeners, and thixotropic agents. Only one of the above other components may be used, or two or more may be used in combination.

[0165] (Other details of resin materials) When the resin component contains a thermoplastic resin, the melting point (Tm) of the resin material is preferably 100° C. or higher, more preferably 150° C. or higher, even more preferably 200° C. or higher, and preferably 300° C. or lower, more preferably 280° C. or lower, and even more preferably 260° C. or lower. When the melting point (Tm) of the resin material is above the lower limit and below the upper limit, the resin component and COF are easily mixed uniformly during production of the resin material, making it easier to obtain a resin material with highly uniform performance, such as electrical properties and mechanical properties.

[0166] If the melting point (Tm) of the resin material exceeds 300° C., the heat resistance of the resin material can be increased, making it suitable for use in high-voltage circuit boards.

[0167] The melting point (Tm) of the resin material can be determined by DSC (differential scanning calorimetry) in accordance with JIS K 7121. Specifically, it can be determined as follows.

[0168] Approximately 5 mg of sample (resin material) is placed in a dedicated aluminum container and measured using a differential scanning calorimeter (e.g., PerkinElmer's "DSCPyris1" or "DSC7"), which is heated from 30°C to 200°C at a rate of 320°C / min and held at 200°C for 5 minutes. The temperature is then lowered from 200°C to 30°C at a rate of 10°C / min and held at 30°C for 5 minutes. The melting point is then determined from the endothermic curve as the temperature is increased at 10°C / min. If multiple peaks are detected during measurement, the highest peak temperature detected is defined as the melting point (Tm) of the resin material.

[0169] The water absorption rate of the resin material is preferably 1% by weight or less, more preferably 0.5% by weight or less, and even more preferably 0.1% by weight or less. When the water absorption rate of the resin material is equal to or less than the upper limit, fluctuations in the dielectric constant due to moisture absorption can be effectively suppressed. The water absorption rate of the resin material may be 0% by weight or more, greater than 0% by weight, 0.05% by weight or more, greater than 0.1% by weight, or greater than 0.2% by weight.

[0170] The water absorption rate of the resin material means the water absorption rate when the resin material is immersed in water at 25° C. for 24 hours. Specifically, it can be measured as follows.

[0171] After drying the resin material at 80°C for 5 hours, the weight of the resin material is measured and designated as weight W1. Next, the resin material is immersed in water at 25°C for 24 hours. After immersion, the surface of the resin material is thoroughly wiped, and the weight of the resin material is measured and designated as weight W2. The water absorption rate is calculated using the following formula. If the resin material is a resin paste, the solvent is removed and the curing reaction is allowed to proceed, turning it into a solid state, before measuring the weights W1 and W2.

[0172] Water absorption rate (weight %) = (W2-W1) / W1×100

[0173] The resin material can be produced by mixing a resin component, a COF, and, if necessary, other components. A resin film can also be produced by molding a composition (resin composition) obtained by mixing a resin component, a COF, and, if necessary, other components into a film. Examples of methods for producing a resin film include: an extrusion molding method in which a resin composition is melt-kneaded and extruded using an extruder, and then molded into a film using a T-die, circular die, or the like; a casting molding method in which a resin composition containing a solvent is cast into a film; and other conventionally known film molding methods. The extrusion molding method and the casting molding method are preferred because they can be used to make thinner films. Films include sheets.

[0174] When the resin material is a resin paste, the resin paste is preferably applied to the surface of the object, and when the resin material is a resin film, the resin film is preferably laminated to the surface of the object.

[0175] The resin material can be used for various purposes. For example, the resin material is preferably used to form a molding resin in which a semiconductor chip is embedded in a semiconductor device. The resin material is preferably used as a semiconductor encapsulation material.

[0176] The resin material is suitable for use as a replacement for liquid crystal polymers (LCPs), a millimeter-wave antenna, or a rewiring layer. The resin material is not limited to these uses, but is suitable for general wiring formation applications.

[0177] The resin material is preferably used as an adhesive material. The resin material is preferably used, for example, as an adhesive material for power overlay packages, an adhesive material for printed wiring boards, an adhesive material for coverlays of flexible printed circuit boards, or an adhesive material for semiconductor bonding. The resin material is preferably an adhesive material. The resin material is preferably used, for example, in electronic device components, for bonding components and for joining components.

[0178] The resin material has a low dielectric constant and is therefore suitable for use as a low refractive index material. The resin material is suitable for use as a component bonding material in, for example, the fields of optical communications, optical information processing, and electronic devices having display devices such as virtual reality (VR), mixed reality (MR), and augmented reality (AR). The resin material is suitable for use in, for example, optical communications or optical information processing devices, for bonding optical components, and for joining optical components.

[0179] The resin material is preferably used as an insulating material. The resin material is preferably used to form an insulating layer in a printed wiring board, and more preferably to form an insulating layer in a multilayer printed wiring board. The resin material is preferably an insulating material, and more preferably an interlayer insulating material. The insulating material may also serve as an adhesive material.

[0180] The multilayer printed wiring board includes, for example, a circuit board, a plurality of insulating layers disposed on the surface of the circuit board, and a metal layer disposed between the plurality of insulating layers. In the multilayer printed wiring board, at least one of the insulating layers is formed from the resin material described above. When the resin material contains a thermosetting compound, at least one of the insulating layers is a cured product of the resin material described above.

[0181] FIG. 1 is a cross-sectional view schematically showing a multilayer printed wiring board using a resin material according to one embodiment of the present invention.

[0182] In the multilayer printed wiring board 11 shown in FIG. 1, a plurality of insulating layers 13-16 are stacked on the upper surface 12a of a circuit board 12. The insulating layers 13-16 are formed of a resin material. A metal layer 17 is formed on a partial region of the upper surface 12a of the circuit board 12. Of the plurality of insulating layers 13-16, the insulating layers 13-15 other than the insulating layer 16 located on the outer surface opposite the circuit board 12 have the metal layer 17 formed on a partial region of the upper surface. The metal layer 17 is a circuit. The metal layer 17 is disposed between the circuit board 12 and the insulating layer 13, and between each of the stacked insulating layers 13-16. The lower metal layer 17 and the upper metal layer 17 are connected to each other by at least one of via hole connection and through hole connection (not shown).

[0183] In this embodiment, the surfaces of the insulating layers 13 to 16 are roughened, so that fine holes (not shown) are formed in the surfaces of the insulating layers 13 to 16. The metal layer 17 extends into the fine holes. In the multilayer printed wiring board 11, the width dimension (L) of the metal layer 17 and the width dimension (S) of the portion where the metal layer 17 is not formed can be reduced. In the multilayer printed wiring board 11, good insulation reliability is provided between the upper and lower metal layers that are not connected by via hole connections or through hole connections (not shown). [Explanation of symbols]

[0184] 11...Multilayer printed wiring board 12...Circuit board 12a…Top surface 13~16...Insulating layer 17...Metal layer

Claims

[Claim 1] A resin component, a covalent organic framework; the covalent organic framework has a negative linear expansion coefficient or has boron atoms; the resin component includes a thermosetting compound, a curing agent, and a thermoplastic resin; the content of the curing agent relative to 100 parts by weight of the thermosetting compound is 10 parts by weight or more and 140 parts by weight or less; The resin material, wherein the thermoplastic resin is a polyimide resin or a phenoxy resin.

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