Dielectric Copolymer Materials

Abstract

The present invention relates to a polymerizable mixture that can be used to form a dielectric material for preparing a passivation layer in an electronic device. The polymerizable mixture includes a first monomer and a second monomer, which react to form a copolymer that can provide excellent film-forming ability, excellent thermal properties, and excellent mechanical properties. Methods for forming the copolymer and electronic devices comprising the copolymer as a dielectric material are also provided. Furthermore, the present invention relates to manufacturing methods for preparing packaged microelectronic structures and microelectronic devices comprising packaged microelectronic structures formed by the manufacturing methods.

Description

[Technical Field]

[0001] The present invention relates to a new class of copolymers that can be used as dielectric materials for preparing passivation layers in packaged electronic devices. The copolymers are obtained from a polymerizable mixture containing a first monomer and a second monomer, where the first monomer is one or more polymerizable tri- or 3,4-disubstituted maleimide compounds having mesogenic groups, and the second monomer is one or more di- or polyfunctional compounds capable of reacting with the first monomer to form the copolymer. The first monomer is sometimes referred to as a reactive mesogen (RM). Thus, the copolymers obtained therefrom are materials with structure-preserving liquid crystal characteristics, and offer excellent film-forming ability, excellent thermal properties, excellent mechanical properties, and easy processing from conventional solvents. In particular, the copolymers are characterized by a low dielectric constant and thermomechanical properties that reduce thermally induced stress due to the mismatch in coefficient of thermal expansion (CTE) between the package and the silicon-rich (3 ppm / K) and copper-rich (16.5 ppm / K) substrate. Furthermore, the copolymers offer a good balance between stiffness and resilience so that thermal stresses can be easily compensated for.

[0002] Furthermore, the copolymers are photostructurable and are particularly suitable for various applications in electronic packaging, such as, for example, passivation of conductive or semiconductive components and die attachment, as well as for use as key components in the preparation of substrates for printed circuit boards. Further provided are methods for forming the copolymers and electronic devices comprising the copolymers as dielectric materials.Furthermore, the present invention relates to a manufacturing method for preparing a packaged microelectronic structure, wherein a dielectric copolymer layer is formed from a polymerizable mixture, and to a microelectronic device comprising a packaged microelectronic structure obtained or obtainable by said manufacturing method. The manufacturing method according to the present invention enables the production of cost-effective and reliable microelectronic devices with a significantly reduced number of defective products caused by mechanical deformation (warpage) due to undesired thermal expansion. Polymerization and / or curing can occur at significantly lower temperatures, resulting in lower thermal stresses during manufacturing and reduced waste of defective microelectronic devices, thereby enabling resource-efficient and sustainable production. [Background technology]

[0003] Reactive mesogens (RMs) produce anisotropic polymers that preserve the liquid crystalline state when polymerized at temperatures that exhibit a thermotropic liquid crystal (LC) phase (typically nematic, cholesteric, or smectic). In particular, optical anisotropy has been widely exploited in the field of optical films for compensation and brightness enhancement of flat panel displays, especially liquid crystal displays. In addition to their widespread use in liquid crystal displays and displays, liquid crystal materials are being investigated for their advantages in other types of applications due to their unique physical properties (R. Stannarius, Nat. Mat. 2009, Vol. 8, pp. 617-618; and J.P. F. Lagerwall et al., Current Appl. Phys. 2012, Vol. 12, pp. 1387-1412). In particular, highly ordered anisotropic polymer networks are an interesting class of materials with a diverse range of applications (D.J.Broer et al., Lagmuir 2014, Vol. 30, pp. 13499-13509; and R. Zentel et al., Adv. Mater. 2010, Vol. 22, pp. 3366-3387). However, in most cases, LC polymers or the corresponding monomers that make up the polymers do not have the optimal properties required for each application.

[0004] WO 2012 / 152409 relates to polymer particles with optical and shape anisotropy comprising at least one reactive mesogenic monomer unit, a method for preparing them, optical, electro-optical, electronic, electrochemical, electrophotographic, electrowetting, and electrophoretic displays and / or devices comprising the polymer particles, and security, cosmetic, decorative, and diagnostic applications, as well as the use of such particles for preparing electrophoretic fluids and displays. In particular, the polymer particles comprise at least one RM monomer unit having at least two polymerizable groups, at least one polymerizable dye as a comonomer, optionally at least one comonomer, optionally at least one crosslinking comonomer, optionally at least one ionic comonomer, and optionally at least one polymerizable stabilizer.

[0005] Various methods for preparing liquid crystal polymers from RMs and for preparing RM starting materials are known from the prior art. For example, Siemensmeyer et al. describe a method for producing a mixture of LC compounds, where at least one of the starting components consists of a mixture of at least two compounds, which mixture is reacted with at least one other starting component to form a statistical mixture (WO 96 / 04351). In addition to efficient methods for preparing LC compounds, suitable polymerization methods for forming anisotropic polymer networks are of interest. Various reactive functional groups have been investigated for their applicability in photoinitiated polymerization reactions. The most common reactive functional groups are acrylates and methacrylates, which are particularly well suited for UV-induced free-radical polymerization due to their fast polymerization rates (DJ Broer et al., Lagmuir 2014, Vol. 30, pp. 13499-13509). However, UV curing is not suitable for all types of applications.

[0006] Mixtures of polymerizable liquid crystal monomers (reactive mesogens) can be used to prepare thin films that can be cured by thermal or photoinitiated polymerization. The films prepared in this way are relatively thin and contain highly crosslinked duroplastic polymers with remarkable dimensional stability. However, these films are relatively brittle and exhibit very low elasticity. On the other hand, if the degree of crosslinking is reduced, dimensionally stable polymer films cannot be obtained.

[0007] U.S. Patent No. 6,261,481 describes an organic insulating composition that provides good thermal conductivity. The insulating composition includes a liquid crystal (LC) resin comprising the polymerization product of a resin composition containing a monomer having a mesogenic group. The composition has a thermal conductivity of ≥ 0.4 W / mK in mutually perpendicular directions. The monomer contained in the resin composition has a mesogenic group and, preferably, an epoxy group that can be thermally polymerized under an acid catalyst. Preferably, the resin composition is heated under conditions that partially align the monomer having the mesogenic group at the start of polymerization, so that the anisotropic properties based on the partial alignment are fixed in the polymer. US Patent Application Publication Nos. 2008 / 0075961 and 2017 / 0152418 relate to maleimide adhesive films prepared from thermosetting maleimide resins containing imide-extended mono-, bis-, and polymaleimide compounds. The maleimide adhesive films are photostructurable and suitable for the production of electronic devices, integrated circuits, semiconductor substrates, passive components, solar cells, solar cell modules, and / or light-emitting diodes. However, the maleimide compounds do not contain any mesogenic groups that can impart preferential orientation or partial alignment of the compounds in the film. This results in poorer properties in terms of mechanical stability and thermal conductivity. Such materials also typically exhibit relatively low glass transition temperatures, which again affects thermal expansion properties. Korean Patent Application Publication No. 20160052234 describes a photocurable insulating resin composition and a printed circuit board using the same. The photocurable insulating resin composition includes a photocurable liquid crystal oligomer, a photocurable graphene oxide, and a photocurable metal alkoxide. However, the photocurable liquid crystal oligomer does not contain multiple mesogenic groups linked together by a spacer group. This results in an unfavorable solubility profile, and the energy required for photocuring is very high.

[0008] Electronic Packaging As semiconductor transistors began to replace vacuum tube technology, it became possible to attach electronic components such as resistors, capacitors, and diodes directly to the card's printed circuit board with wire leads, thus establishing the basic building blocks or levels of packaging that are still in use today. Complex electronic functions often require more individual components than can be interconnected on a single printed circuit card. With the development of three-dimensional packaging of daughter cards onto multi-layer motherboards, multi-layer cards became possible. Integrated circuits allow many of the individual circuit elements, such as resistors and diodes, to be integrated into individual, relatively small components known as integrated circuit chips or dies. However, despite tremendous circuit integration, more than one packaging level is typically required, in part due to the integrated circuit technology itself. Integrated circuit chips are very fragile and have very small terminals. The first level of packaging performs the primary functions of providing mechanical protection, cooling, and electrical connection capability to the delicate integrated circuit. Some components (high-power resistors, mechanical switches, capacitors) are not easily integrated onto a chip, so at least one additional packaging level, such as a printed circuit card, is used. For highly complex applications such as mainframe computers, multiple packaging levels are required. As a result of Moore's Law, advanced electronic packaging strategies are playing an increasingly important role in the development of more powerful electronic products. In other words, as the demand for smaller, faster, and more capable portable and handheld electronic devices increases, so too does the demand for improved, cost-effective packaging technologies.

[0009] A wide variety of advanced packaging technologies exist to meet the demands of today's semiconductor industry. Leading advanced packaging technologies, such as wafer-level packaging (WLP), fan-out wafer-level packaging (FOWLP), 2.5D interposers, chip-on-chip stacking, package-on-package stacking, and embedded ICs, all require structuring of other components such as thin substrates, redistribution layers, and high-resolution interconnects. End-consumer markets are constantly demanding lower prices and higher functionality for ever smaller and thinner devices. This necessitates next-generation packaging with finer features and improved reliability at competitive manufacturing costs.

[0010] Wafer-level packaging (WLP) is a technology that packages integrated circuits while they are still part of a wafer, as opposed to more traditional chip-scale packaging methods in which wafers are sliced ​​into individual circuits (dice) and then packaged. WLP offers several key advantages over chip-scale packaging technologies, and since the resulting package is effectively the same size as the die, it is essentially a true chip-scale package (CSP) technology. Wafer-level packaging enables the integration of wafer fabrication, packaging, test, and burn-in at the wafer level to streamline the manufacturing process a device undergoes from silicon starting material to customer shipment. Due to size constraints, the primary application areas for WLP are smartphones and wearables. Features that WLP provides to smartphones or wearables include compass, sensors, power management, and wireless. Wafer-level chip-scale packaging (WL-CSP) is one of the smallest packages currently available on the market. WLP can be categorized as fan-in WLP and fan-out WLP (Figure 1), both of which use redistribution techniques to form connections between the chip and solder balls. Fan-out wafer-level packaging (FOWLP) is one of the latest packaging trends in microelectronics. FOWLP has high miniaturization potential in both package volume and package thickness. The technological basis of FOWLP is a reconfigured printed wafer with embedded chips and a thin-film redistribution layer, which together form a surface-mount device (SMD) compatible package. The main advantages of FOWLP are its very thinness due to the substrateless package, low thermal resistance, and good high-frequency characteristics due to short, planar electrical connections together with bumpless chip connections instead of wire bonds or solder contacts, for example.

[0011] With current materials, the WLP process is limited to medium-chip-size applications. This limitation is primarily due to the current material selection, which exhibits a thermal mismatch with the silicon die (CTE: 3 ppm / K), potentially reducing performance and generating stress in the die. New materials with better physical properties—particularly a coefficient of thermal expansion (CTE) closer to that of silicon, along with high mechanical flexibility—are highly sought after. Currently, redistribution layers (RDLs) are fabricated with copper layers (CTE: 16.5 ppm / K) electroplated onto a polymer passivation layer, such as polyimide (PI), butylcyclobutane (BCB), or polybenzoxazole (PBO). Low curing temperatures, along with photopatternability, are two additional important requirements for processing such materials. Polyimides have become the standard passivation layer for memory chips and other devices that require surface protection for handling and testing procedures. To reduce processing costs, photosensitive resins have been developed. Polyimide-ODA is the first member of a series of new high-performance polymers based on alternating aromatic homocyclic and heterocyclic rings developed by DuPont: [ka]

[0012] Polyimides are quite unique in that they have a very high decomposition temperature, which can exceed 400°C. In addition, their mechanical properties ensure high flexibility (up to 100% elongation at break) along with a very high tensile strength of over 200 MPa. PI remains the most widely used polymer for IC passivation. The modification to negatively sensitive polymeric PI was achieved using polybenzoxazole (PBO), which is sometimes also called positively sensitive PI. [ka] After exposure, the polymer film can be developed using an aqueous developer. The so-called BCB (benzocyclobutene) is an example of a siloxane-polymer group which additionally contains a vinyl and a benzocyclobutene ring system. [ka]

[0013] Its main advantage is the polymerization reaction (Diels-Alder reaction) which is atom-efficient due to the absence of by-products. This highly cross-linked thermosetting polymer has excellent electrical performance but is very brittle, with a low elongation at break (8%) and a low tensile strength of 87 MPa. Another state-of-the-art approach is the imide-extended bismaleimide resins suggested in U.S. Patent Application Publication Nos. 2008 / 0075961 and 2017 / 0152418. These have shown promising results for low-stress wafer passivation coatings. However, despite some improvement, there is still room for improvement to meet stringent industry requirements.

[0014] In conclusion, the materials known in the state of the art exhibit the following drawbacks: Polyimides and polybenzoxazoles typically require very high processing temperatures, which increases the risk of warpage, especially in multi-layer redistribution layers (RDLs). In addition, polyimides exhibit high water absorption, which is problematic for device reliability. Benzocyclobutene derivatives as well as polynorbornenes exhibit very low dielectric constants, but this advantage is compromised by very poor adhesion to metals. Imide-extended bismaleimide resins to date have not exhibited a desirable combination of advantageous mechanical and thermal properties: they are either flexible (low modulus) but have high CTE values, or brittle (high modulus) and have low CTE values. Therefore, there is a continuing need to develop new dielectric materials that do not exhibit the above-mentioned drawbacks known in the prior art.

[0015] Photolithography Photolithography has long been a key patterning technology for structuring inorganic and organic materials used in advanced packaging applications such as flip-chip wafer bumping, electroplated gold, solder bumps, copper pillar technology, and redistribution layers. Photolithography is a significant manufacturing process and cost contributor, and careful selection of the proper exposure tool is critical to achieving the best possible cost structure in today's industrial lithography applications. Current drivers and trends in the semiconductor industry clearly indicate that improved performance of microelectronic devices is necessary to meet future end-user demands. For example, consumer electronic devices such as tablets and smartphones are becoming thinner and smaller while acquiring higher computing power, increased data storage, and improved communication capabilities. In addition, cost considerations are becoming increasingly important in the competitive environment for all parties in the supply chain, from chipmakers, foundries, assembly and test suppliers to device manufacturers. Therefore, the industry is striving to find innovative ways to reduce manufacturing costs while enabling technologies that meet challenging technical demands. For decades, photolithography has been a fundamental process used in the manufacturing and packaging of microelectronic devices, and it remains so today. A key component of any photolithography process is an exposure tool, which uses light in the ultraviolet wavelength range to pattern a photosensitive resist or polymer. The exposure tool must be able to precisely create the desired features and align them with structures already fabricated in the layer below. Today, several types of exposure techniques exist: proximity or contact printing, laser direct imaging, and projection lithography. The corresponding equipment toolsets differ in terms of technical capabilities (optical resolution, overlay performance, and effective throughput) and costs associated with the exposure process. (See H. Hichri et al., SUSS Micro Tec Photonic Systems Inc., Corona, California, USA.) Summary of the Invention

[0016] Object of the invention It is an object of the present invention to overcome the deficiencies and drawbacks of the prior art and to provide a new class of materials that can be used as versatile dielectric materials in a variety of electronic packaging applications. It is a further object of the present invention to provide a new class of dielectric materials that, when used to form passivation layers in packaged electronic devices, exhibit excellent film-forming capabilities, excellent thermal properties, e.g., low coefficient of thermal expansion (CTE), and excellent mechanical properties, e.g., excellent flexibility. It is a further object of the present invention to provide a new class of dielectric materials that allow for easy processing from conventional solvents. More specifically, the objective of the present invention is to match the thermal expansion coefficient of the dielectric to that of, for example, silicon (Si: 3 ppm / K) or copper (Cu: 16.5 ppm / K) without adversely affecting mechanical properties such as, for example, elongation at break after UV or heat curing at temperatures below 200°C. It is a further object of the present invention to provide a new class of materials which are photostructurable and which are particularly suitable for various applications in electronic packaging, such as, for example, the passivation and die attachment of conductive or semiconductive components, as well as for use as a key component in the preparation of substrates for printed circuit boards. An important field of application is their use as dielectric materials for structuring the RDL of packaged microelectronic devices. It is a further object of the present invention to provide a polymerizable mixture from which the novel material is fabricated. Furthermore, it is an object of the present invention to provide a method for forming the novel material using the polymerizable mixture. Finally, it is an object of the present invention to provide an electronic device comprising the novel material as a dielectric material, a manufacturing method for preparing a packaged microelectronic structure, and a microelectronic device comprising a packaged microelectronic structure obtainable by said manufacturing method.

[0017] Summary of the Invention The present inventors have surprisingly found that the above objects are achieved by a copolymer obtainable from a polymerizable mixture comprising a first monomer and a second monomer, wherein the first monomer is one or more compounds represented by formula (1) and the second monomer is one or more di- or polyfunctional compounds capable of reacting with the first monomer to form the copolymer. P 1 -Sp 1 -(MG-Sp 1 ) m -P 1 Formula (1) During the ceremony, m is an integer from 1 to 60; P 1 teeth, [ka] wherein V 1 is H and V 2 is alkyl having 1 to 6 carbon atoms, F, Cl, or CN, or V 1 and V 2 are each independently an alkyl having 1 to 6 carbon atoms, F, Cl, or CN; Sp 1 represents, at each occurrence, a spacer group (Sp) or a single bond; MG preferably has the formula (2): -(A 21 -Z 21 ) k -A 22 -(Z 22 -A 23 ) l - Formula (2) is a rod-shaped mesogenic group selected from the formula: A 21 ~A 23 are independently, and in each occurrence independently of one another, an aryl, heteroaryl, heterocyclic, alicyclic, or cyclic imide group optionally substituted by one or more identical or different groups L; Z 21 and Z 22are independently and in each occurrence independently of one another -O-, -S-, -CO-, -COO-, -OCO-, -S-CO-, -CO-S-, -O-COO-, -CONR 01 -, -NR 01 -CO-, -NR 01 -CO-NR 02 , -NR 01 -CO-O-, -O-CO-NR 01 -, -OCH2-, -CH2O, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH2CH2-, -(CH2)4-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 01 -, -CY 01 =CY 02 -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond; R 01 and R 02 each independently represent H or alkyl having 1 to 12 C atoms, L is F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)NR xx R yy , -C(=O)OR xx , -C(=O)R xx , -NR xx R yy , -OH, -SF5, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 20 C atoms, in which one or more H atoms are optionally replaced by F, or Cl, -CN, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 6 C atoms, R xx and R yy denote, independently of one another, H or alkyl having 1 to 12 C atoms, Y 01 and Y 02each independently represent H, an alkyl having 1 to 12 carbon atoms, an aryl, F, Cl or CN, k and l are each independently 0, 1, 2, 3, or 4.

[0018] The polymerizable mixture is used as a starting material for forming a new class of copolymers that exhibit low thermal expansion and at the same time high mechanical flexibility, which copolymers can be prepared by the following process, which also forms part of the present invention: 1. A method for forming a copolymer, comprising: (i) providing a polymerizable mixture according to the present invention; and (ii) polymerizing the polymerizable mixture to obtain a copolymer. It is prepared by a method comprising: Further provided is a copolymer obtainable or obtainable by the above-described method for forming a copolymer. Additionally, there is provided an electronic device comprising a copolymer according to the present invention.

[0019] Finally, there is provided a manufacturing method for preparing a packaged microelectronic structure in which a substrate is provided with a dielectric layer, the method comprising: (1) applying a polymerizable mixture according to the present invention to the surface of a substrate; and (2) polymerizing the polymerizable composition to form a dielectric layer; A method is provided that includes: There is also provided a microelectronic device comprising a packaged microelectronic structure obtainable or obtainable by a manufacturing method according to the invention. Preferred embodiments of the invention are set out below and in the dependent claims. [Brief explanation of the drawings]

[0020] [Figure 1] FIG. 1 is a cross-sectional view of a fan-in and fan-out WLP with a die (1) and a fan-out region (2). DETAILED DESCRIPTION OF THE INVENTION

[0021] definition The terms "liquid crystal," "mesomorphic compound," or "mesogenic compound" (also called "mesogen" for short) refer to compounds that can exist as a mesophase, or in particular as an LC phase, under suitable conditions of temperature, pressure, and concentration. Non-amphiphilic mesogenic compounds contain, for example, one or more calamitic, banana-shaped, or discotic mesogenic groups. The term "calamitic" refers to a compound or group that is rod- or plate-like / lath-shaped. The term "banana-shaped" refers to a curved group in which two, usually calamitic, mesogenic groups are connected via a semi-rigid group so that they are not collinear. The term "discoidic" refers to a compound or group that is disc- or sheet-shaped. The term "mesogenic group" or its abbreviation "MG" refers to a group capable of inducing liquid crystal (LC) phase behavior. Mesogenic groups, especially non-amphiphilic types, are usually either calamitic or discotic. Compounds containing mesogenic groups do not necessarily exhibit LC phases by themselves. Such compounds may exhibit LC phase behavior only in mixtures with other compounds or when the mesogenic compound or a mixture thereof is polymerized. For simplicity, the term "liquid crystal" is used hereinafter for both mesogenic and LC materials. Calamitic mesogenic compounds typically comprise calamitic, i.e. rod- or lath-like, mesogenic groups consisting of one or more aromatic or alicyclic groups connected to one another either directly or via linking groups, optionally including terminal groups attached to the short ends of the rods, and optionally including one or more side groups attached to the long sides of the rods, where such terminal and side groups are typically selected from, for example, carbyl or hydrocarbyl groups; polar groups such as halogen, nitro, hydroxy, etc.; or polymerizable groups.

[0022] Discotic mesogenic compounds typically comprise a discotic, i.e., relatively flat, disk-like or sheet-like mesogenic group, consisting of, for example, one or more fused aromatic or alicyclic groups, such as, for example, triphenylene, optionally attached to the mesogenic group and comprising one or more terminal groups selected from the terminal and lateral groups mentioned above. The term "reactive mesogen" or its abbreviation "RM" refers to a polymerizable mesogenic or liquid crystalline compound, which is preferably a monomeric or oligomeric compound. The term "spacer" or "spacer group", hereinafter also referred to as "Sp", is known to those skilled in the art and described in the literature. Unless otherwise stated, the term "spacer" or "spacer group" above and below means a flexible organic group that connects a mesogenic group and a polymerizable group in a polymerizable mesogenic compound ("RM").

[0023] The term "polymer" includes, but is not limited to, homopolymers, copolymers, such as block, random, and alternating copolymers, terpolymers, quaterpolymers, etc., as well as blends and modifications thereof. Furthermore, unless otherwise specifically limited, the term "polymer" is intended to include all possible configurational isomers of a material. Such configurations include, but are not limited to, isotactic, syndiotactic, and atactic symmetries. Polymers are molecules of high relative molecular weight whose structure essentially comprises multiple repeats of units (i.e., repeat units) derived, actually or conceptually, from molecules of lower relative mass (i.e., monomers). In the context of the present invention, a polymer is composed of more than 60 monomers.

[0024] The term "oligomer" refers to a molecular complex consisting of a small number of monomer units, in contrast to a polymer, which in principle has an unlimited number of monomers. Dimers, trimers, and tetramers are, for example, oligomers consisting of two, three, and four monomers, respectively. In the context of the present invention, an oligomer may consist of up to 60 monomers. The term "monomer," as used herein, refers to a polymerizable compound that can undergo polymerization, thereby contributing a constitutional unit (repeat unit) to the essential structure of a polymer or oligomer. A polymerizable compound is a functionalized compound that has one or more polymerizable groups. Multiple monomers combine to form a polymer in a polymerization reaction. A monomer with one polymerizable group is also called a "monofunctional" or "monoreactive" compound, a compound with two polymerizable groups is also called a "difunctional" or "direactive" compound, and a compound with more than two polymerizable groups is also called a "multifunctional" or "multireactive" compound. A compound without a polymerizable group is also called a "non-functional" or "non-reactive" compound.

[0025] The term "homopolymer," as used herein, refers to a polymer derived from one species of monomer (real, implied, or hypothetical). The term "copolymer," as used herein, generally refers to any polymer derived from more than one type of monomer and containing more than one type of corresponding repeat unit. In one embodiment, a copolymer is the reaction product of two or more types of monomer and thus contains two or more types of corresponding repeat units. Preferably, the copolymer contains two, three, four, five, or six types of repeat units. Copolymers obtained by copolymerization of three types of monomers may also be called terpolymers. Copolymers obtained by copolymerization of four types of monomers may also be called quaterpolymers. Copolymers may exist as block, random, and / or alternating copolymers.

[0026] The term "block copolymer," as used herein, refers to a copolymer in which adjacent blocks are compositionally different, i.e., adjacent blocks contain repeat units derived from different types of monomers, or from the same type of monomers but differing in the composition or sequence distribution of the repeat units. Furthermore, the term "random copolymer," as used herein, refers to a polymer formed of macromolecules in which the probability of finding a given repeat unit at any given site in the chain is independent of the nature of adjacent repeat units. Typically, in random copolymers, the sequence distribution of repeat units follows Bernoulli statistics. The term "alternating copolymer," as used herein, refers to a copolymer consisting of macromolecules containing two types of repeat units that alternate in sequence.

[0027] "Electronic packaging" is a major area within the field of electronics and encompasses a wide variety of technologies. The term refers to the insertion of discrete components, integrated circuits, and MSI (medium-scale integration) and LSI (large-scale integration) chips (usually attached to lead frames with beam leads) into through-holes on plated multilayer circuit boards (also called cards) where they are soldered in place. Packaging of electronic devices must consider protection from mechanical damage, cooling, radio frequency noise emissions, protection from electrostatic discharge, maintenance, operator convenience, and cost. The term "microelectronic device," as used herein, refers to electronic devices and components of very small electronic designs. This usually, but not always, means on the micrometer scale or smaller. Such devices typically include one or more microelectronic components fabricated from semiconductor materials and interconnected in a packaging structure to form the microelectronic device. Many electronic components of typical electronic designs have available microelectronic equivalents. Electronic components include transistors, capacitors, inductors, resistors, and diodes, and, of course, insulators and conductors can all be found in microelectronic devices. Due to the extremely small size of components, leads, and pads in microelectronics, unique wiring techniques such as wire bonding are also frequently used.

[0028] "Nanoparticles," as used herein, are particles having an average diameter in the range of 1 to 100 nm. More preferably, nanoparticles have an average diameter in the range of 20 to 80 nm, more preferably 40 to 60 nm.

[0029] Preferred Embodiments polymerizable compound The present invention relates to a polymerizable mixture comprising a first monomer and a second monomer, wherein the first monomer is one or more compounds represented by formula (1) and the second monomer is one or more di- or polyfunctional compounds capable of reacting with the first monomer to form a copolymer. P 1 -Sp 1 -(MG-Sp 1 ) m -P 1 Formula (1) During the ceremony, m is an integer from 1 to 60; P 1 teeth, [ka] wherein V 1 is H and V 2 is alkyl having 1 to 6 carbon atoms, F, Cl, or CN, or V 1 and V 2 are each independently an alkyl having 1 to 6 carbon atoms, F, Cl, or CN; Sp 1 represents, at each occurrence, a spacer group (Sp) or a single bond; MG preferably has the formula (2): -(A 21 -Z 21 ) k -A 22 -(Z 22 -A 23 ) l - Formula (2) is a rod-shaped mesogenic group selected from the formula: A 21 ~A 23are independently, and in each occurrence independently of one another, an aryl, heteroaryl, heterocyclic, alicyclic, or cyclic imide group optionally substituted by one or more identical or different groups L; Z 21 and Z 22 are independently and in each occurrence independently of one another -O-, -S-, -CO-, -COO-, -OCO-, -S-CO-, -CO-S-, -O-COO-, -CONR 01 -, -NR 01 -CO-, -NR 01 -CO-NR 02 , -NR 01 -CO-O-, -O-CO-NR 01 -, -OCH2-, -CH2O, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH2CH2-, -(CH2)4-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 01 -, -CY 01 =CY 02 -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond; R 01 and R 02 each independently represent H or alkyl having 1 to 12 C atoms, L is F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)NR xx R yy , -C(=O)OR xx , -C(=O)R xx , -NR xx R yy, -OH, -SF5, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 20 C atoms, in which one or more H atoms are optionally replaced by F, or Cl, -CN, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 6 C atoms, R xx and R yy denote, independently of one another, H or alkyl having 1 to 12 C atoms, Y 01 and Y 02 each independently represent H, an alkyl having 1 to 12 carbon atoms, an aryl, F, Cl, or CN, k and l are each independently 0, 1, 2, 3, or 4.

[0030] The attachment points (binding sites) of the structural elements presented in this patent application are: [ka] In some cases, the formula is * represents a structural element, [ka] represents the binding site.

[0031] Polymerizable group P 1 is a 3-substituted or 3,4-disubstituted maleimide group capable of undergoing a polymerization reaction, e.g., a radical or ionic chain polymerization reaction, or a polyaddition reaction (e.g., a 2+2 cycloaddition, a 4+2 cycloaddition (Diels-Alder reaction), or a 1,3-dipolar cycloaddition, or a nucleophilic addition such as a Michael reaction), or a polymerization-like reaction, e.g., addition to a polymer backbone by one of the reaction types described above. The index m is preferably an integer of 1 to 50, more preferably 2 to 30, and most preferably 3 to 20.

[0032] V 1 and V 2 are preferably selected independently from alkyl having 1 to 6 carbon atoms, F, Cl, or CN. 1 and V 2 are more preferably selected independently from alkyl having 1 to 3 carbon atoms, F, Cl, or CN. Preferred alkyl having 1 to 3 carbon atoms are methyl, ethyl, and propyl. 1 and V 2 may be the same or different from each other. 1 and V 2 are particularly preferably the same. Or, V 1 is H and V 2 is preferably selected from alkyl having 1 to 6 carbon atoms, F, Cl, or CN, more preferably from alkyl having 1 to 3 carbon atoms, F, Cl, or CN. Preferred alkyl having 1 to 3 carbon atoms are methyl, ethyl, and propyl. Z 21 and Z 22 are independently and in each occurrence independently of one another -COO-, -OCO-, -CO-O-, -O-CO-, -OCH2-, -CHO-, -CH2CH2-, -(CH2)4-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond. Preferably, k and l are each and independently 0, 1, or 2; more preferably, k and l are 1.

[0033] A preferred spacer group Sp is the radical "P 1 -Sp 1 -" is the formula "P 1 -Sp'-X'-" In the formula, Sp' is (a) linear or branched alkylene having 1 to 40, preferably 1 to 30, C atoms, optionally mono- or polysubstituted by F, Cl, Br, I, or CN, in which one or more non-adjacent CH groups are each independently selected from -O-, -S-, -NH-, -NR ... 01 -, -SiR 01 R 02 -, -CO-, -COO-, -OCO-, -OCO-O-, -S-CO-, -CO-S-, -NR 01 -CO-O-, -O-CO-NR 01 -, -NR 01 -CO-NR 01 a straight or branched alkylene optionally replaced by -, -CH=CH-, or -C≡C-; (b)-Sp x -G-Sp y wherein Sp x and Sp y are independently an alkylene having 1 to 20 C atoms, preferably 1 to 12 C atoms, or a single bond, and G represents a cycloalkylene having 3 to 20 C atoms, preferably 5 to 12 C atoms, optionally mono- or polysubstituted with an alkyl having 1 to 20 C atoms, preferably 1 to 12 C atoms. -Sp x -G-Sp y - indicates X' is -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CONR 01 -, -NR 01 -CO-, -NR 01 -CO-NR 01 -, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=C-, -N=N-, -CH=CR 01 -, -CY 01 =CY 02-, -C≡C-, -CH═CH-COO-, -OCO-CH═CH-, or a single bond, preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, or -CO-NR 0 -, -NR 01 -CO-, -NR 01 -CO-NR 01 - or a single bond, R 01 and R 02 each independently represent H or alkyl having 1 to 12 C atoms, Y 01 and Y 02 each independently represents H, F, Cl, or CN.

[0034] Preferred groups Sp' are in each case selected from linear methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene and octadecylene, cyclohexylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene and butenylene.

[0035] A more preferred spacer group Sp is -(CH2) p1 -, -(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2-, -(SiR 01 R 02 -O) p1 -, -(CH2) p1 -(cyclo-C6H8R 01 R 02 )-(CH2) p1 - and [ka] wherein: p1 is an integer of 1 to 60, preferably 1 to 36, and more preferably 1 to 12; q1 is an integer of 1 to 12, preferably 1 to 3; R 01 and R 02 each independently of one another denotes H or alkyl having 1 to 12 C atoms.

[0036] The most preferred group Sp is -(CH2) p1 -, -O-(CH2) p1 -, -O-(CH2) p1 -O-, -OCO-(CH2) p1 - and -OCOO-(CH2) p1 In the formula, p1 is an integer of 1 to 36, preferably 1 to 12.

[0037] In a preferred embodiment of the present invention, the group A 21 ~A 23 may, independently and, if appearing multiple times, independently of one another, be any of the following groups a) to e): a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene, and 4,4′-bicyclohexylene, in which one or more non-adjacent CH groups may be replaced by —O— and / or —S— and one or more H atoms may be replaced by a group L; b) 1,4-phenylene, 1,3-phenylene, 4,4'-biphenylene, 2,5-thiophene, and 2,6-dithieno[3,2-b:2',3'-d]thiophene, in which one or two CH groups may be replaced by N and one or more H atoms may be replaced by a group L; c) tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobuta-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl, and selenophene-2,5-diyl, optionally substituted by one or more groups L; d) saturated, partially unsaturated or fully unsaturated and optionally substituted polycyclic radicals having 5 to 20 ring C atoms, one or more of which may also be replaced by heteroatoms, said polycyclic radicals being preferably bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, [ka] is selected from the group consisting of in which one or more H atoms may be replaced by a group L, and / or one or more double bonds may be replaced by a single bond, and / or one or more CH groups may be replaced by N, in which M is -O-, -S-, -CH2-, -CHY 03 - or -CY 03 Y 04 - indicates Y 03 , Y 04 are, independently of each other, R 01 denotes one of the meanings given above for F, Cl, CN, OCF3 or CF3, preferably H, F, Cl, CN, OCF3 or CF3, W 5 , W 6 are, independently of each other, -CH2CH2-, -CH=CH-, -CH2-O-, O-CH2-, -C(R c R d )- or -O-, R c , R d denote, independently of one another, H or alkyl having 1 to 6 C atoms, preferably H, methyl or ethyl, R 03 , R 04 are polycyclic radicals, independently of one another, denoting H, F, straight-chain or branched alkyl having 1 to 12 C atoms, in which one or more H atoms may be replaced by F; e) [ka] and a cyclic imide selected from the group consisting of: cyclic imides, in which one or more H atoms may be replaced by a group L, and / or one or more double bonds may be replaced by a single bond, and / or one or more CH groups may be replaced by N; Shows a selected portion from.

[0038] The first monomer contained in the polymerizable mixture according to the present invention is preferably one, two, three or four compounds represented by formula (1).

[0039] Preferred compounds according to formula (1) are [ka] TIFF0007729013000012.tif186115 JPEG0007729013000013.jpg199121 TIFF0007729013000014.tif131123 TIFF0007729013000015.tif198122 TIFF0007729013000016.tif168125 TIFF0007729013000017.tif191125 TIFF0007729013000018.tif20123, where the radicals and indices have the following meanings: L is F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)NR xx R yy , -C(=O)OR xx , -C(=O)R xx , -NR xx R yy, -OH, -SF5, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 20 C atoms, preferably 1 to 12 C atoms, in which one or more H atoms are optionally replaced by F or Cl, preferably F, -CN, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 6 C atoms, R xx and R yy denote, independently of one another, H or alkyl having 1 to 12 C atoms, r is 0, 1, 2, 3, or 4; s is 0, 1, 2, or 3; t is 0, 1, or 2; Z 21 and Z 22 are independently and in each occurrence independently of one another -O-, -S-, -CO-, -COO-, -OCO-, -S-CO-, -CO-S-, -O-COO-, -CONR 01 -, -NR 01 -CO-, -NR 01 -CO-NR 02 , -NR 01 -CO-O-, -O-CO-NR 01 -, -OCH2-, -CH2O, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CH2CH2-, -(CH2)4-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 01 -, -CY 01 =CY 02 -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond, preferably -COO-, -OCO-, -CO-O-, -O-CO-, -OCH-, -CHO-, -CHCH-, -(CH)-, -CFCH-, -CHCF-, -CFCF-, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond; R 01 and R 02 each independently represent H or alkyl having 1 to 12 C atoms, Sp 1 represents, at each occurrence, a spacer group (Sp) as defined above or a single bond; P 1 teeth, [ka] wherein V 1 is H and V 2 is alkyl having 1 to 6 carbon atoms, F, Cl, or CN, or V 1 and V 2 are each independently an alkyl having 1 to 6 carbon atoms, F, Cl, or CN; m is an integer of 1 to 60, preferably 1 to 50, more preferably 2 to 30, and most preferably 3 to 20.

[0040] More preferred compounds according to formula (1) are [ka] JPEG0007729013000021.jpg44113, where the radicals and indices have one of the meanings as defined above.

[0041] Particularly preferred compounds according to formula (1) are [ka] TIFF0007729013000023.tif133119, where the radicals and indices have one of the meanings as defined above.

[0042] The most preferred compounds according to formula (1) are [ka] TIFF0007729013000025.tif194123 JPEG0007729013000026.jpg202127 TIFF0007729013000027.tif207133 TIFF0007729013000028.tif213131, wherein: n is an integer of 1 to 60, preferably 1 to 36, and more preferably 6 to 12; m is an integer of 1 to 60, preferably 1 to 50, more preferably 2 to 30, and most preferably 3 to 20.

[0043] In the compounds of formulae M1 to M33 and corresponding subformulae, the cyclic group [ka] where: L, in each occurrence, independently, is F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)NR xx R yy , -C(=O)OR xx , -C(=O)R xx , -NR xx R yy , -OH, -SF5, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 20 C atoms, preferably 1 to 12 C atoms, in which one or more H atoms are optionally replaced by F or Cl, preferably F, -CN, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 6 C atoms, R xx and R yy is determined in accordance with the provisions given above.

[0044] The compounds of formula (1) can be prepared by any standard synthesis. Usually, the compounds are retrosynthetically cleaved into smaller units and formed stepwise from suitable precursor compounds. For this purpose, known standard reactions can be used. At a later stage of the synthesis, typically at the very end of the synthesis, a 3-substituted or 3,4-disubstituted maleimide group P 1 It has proven particularly advantageous to attach the compound to the polymerizable polymer, as this makes it possible to avoid undesired side reactions or premature polymerization of the compound.

[0045] Preferably, the compound of formula (3): X-Sp 1 -(MG-Sp 1 ) m -X formula (3) The precursor represented by [ka] reacts with the formula (1): P 1 -Sp 1 -(MG-Sp 1 ) m -P 1 Formula (1) to form a polymerizable compound represented by wherein X is NH2; P 1 teeth, [ka] and V 1 , V 2 , Sp 1 , MG, and m have one of the definitions as given above.

[0046] The second monomer contained in the polymerizable mixture according to the present invention is one or more, preferably one, two, three or four, di- or multi-functional compounds capable of reacting with the first monomer to form a copolymer. The second monomer is preferably one or more, preferably one, two, three or four, di- or polyfunctional compounds selected from organic compounds, polyhedral silsesquioxane compounds, and functionalized inorganic nanoparticles. The second monomer is preferably a P-type monomer, preferably a P-type monomer, by radical or ionic chain polymerization or 2+2 cycloaddition. 1 groups containing a C=C double bond that reacts with P in a 4+2 cycloaddition (Diels-Alder reaction); 1 groups containing two conjugated C=C double bonds that react with P 1 and preferably reacts with P in a 1,3-dipolar cycloaddition. 1 Further preferred are one or more, preferably one, two, three or four, di- or polyfunctional compounds comprising two or more polymerizable groups (P) (reactive groups) selected from 1,3-dipolar groups that react with

[0047] Preferred groups containing a C=C double bond are CH2=CW 1 -COO-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -(O) k3 -, CW 1 2=CH-CO-(O) k3 -, CW 1 2=CH-CO-NH-, CH2=CW 1 -CO-NH-, CH3-CH=CH-O-, CH2=CH-CH2-O-, (CH2=CH)2CH-O-CO-, (CH2=CH-CH2)2CH-O-CO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(CO-O) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, or Phe-CH=CH-; is selected from: W 1 denotes H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, preferably H or CH3, W 2 denotes H or alkyl having 1 to 5 C atoms, preferably H or CH3, W 3 and W 4 each independently of one another denotes H, Cl or alkyl having 1 to 5 C atoms, preferably H or CH3, Phe denotes 1,4-phenylene optionally substituted by one or more radicals L as defined above, k1, k2, and k3 each independently represent 0 or 1; k4 is an integer from 1 to 10.

[0048] Preferred groups containing two conjugated C=C double bonds are CW 1 2=CW 1 -CW 1 =CW 1 - selected from: W 1 denotes H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, preferably H or CH3.

[0049] The preferred nucleophilic group is HS-(CH2) k5 -CO-(O) k3 -, HS-(CH2) k5 -CO-, HS-(CH2) k5 -(O) k3 -, HS-(CH2) k5 -O-CO-, HS-(CH2) k5 -CO-NH-, HS-(CH2) k5 -NH-CO-, HS-Phe-(O) k2 -, H2N-(CH2) k5 -CO-(O) k3 -, H2N-(CH2) k5 -CO-, H2N-(CH2) k5 -(O) k3-, H2N-(CH2) k5 -O-CO-, H2N-(CH2) k5 -CO-NH-, H2N-(CH2) k5 -NH-CO-, or H2N-Phe-(O) k2 is selected from: k2 and k3 each independently represent 0 or 1; k5 is an integer of 0 to 10, preferably 0 to 5, and more preferably 0, 1, or 2.

[0050] Preferred 1,3-dipolar groups are [ka] JPEG0007729013000034.jpg163170, wherein: W 5 denote, independently of one another in each occurrence, H, phenyl or alkyl having 1 to 5 C atoms, preferably phenyl or CH3.

[0051] Particularly preferred polymerizable groups (P) are CH2=CW 1 -COO-, CH2=CW 1 -CO-, [ka] , CH2=CW 2 -(O) k3 -, CW 1 2=CH-CO-(O) k3 -, CH3-CH=CH-O-, CH2=CH-CH2-O-, HS-(CH2) k5 -CO-(O) k3 -, HS-(CH2) k5 -CO-, HS-(CH2) k5 -(O) k3 -, HS-(CH2) k5 -O-CO-, H2N-(CH2) k5 -CO-(O) k3 -, H2N-(CH2) k5 -CO-, H2N-(CH2) k5-(O) k3 - or H2N-(CH2) k5 -O-CO-, wherein W 1 denotes H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, preferably H or CH3, W 2 denotes H or alkyl having 1 to 5 C atoms, preferably H or CH3, W 3 and W 4 each independently of one another denotes H, Cl or alkyl having 1 to 5 C atoms, preferably H or CH3, k3 represents 0 or 1, k5 is an integer of 0 to 10, preferably 0 to 5, and more preferably 0, 1, or 2.

[0052] A preferred organic compound used as the second monomer is represented by formula (4): [ka] Formula (4) During the ceremony, Q represents a hydrocarbon group having 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, optionally substituted with one or more substituents L, where L is as defined above and optionally containing one or more heteroatoms selected from N, O and S; P 2 represents a polymerizable group (P) as defined above, x is an integer of 2 to 10, preferably 2 to 4, and more preferably x=2. As is clear from formula (4), the group Q has x bonding sites, each of which is connected to x polymerizable groups P 2 Bind to one of the

[0053] In a preferred embodiment, Q is O(Sp 2 )2, N(Sp 2 )3, NH(Sp 2 )2, C(Sp2 )4, CH(Sp 2 )3, or CH2(Sp 2 )2, wherein Sp 2 is a linear alkylene chain having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, a branched alkylene chain having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, or an aromatic or heteroaromatic moiety having 3 to 14 carbon atoms, preferably an aromatic moiety having 6 to 14 carbon atoms; 2 is a polymerizable group P 2 is bonded to. In a more preferred embodiment, Q is "Ar-Sp 3 -Ar" where Ar is an aromatic or heteroaromatic moiety having 3 to 14 carbon atoms, preferably an aromatic moiety having 6 to 14 carbon atoms, and Sp 3 is a linear alkylene chain having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, a branched alkylene chain having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, or an aromatic or heteroaromatic moiety having 3 to 14 carbon atoms, preferably an aromatic moiety having 6 to 14 carbon atoms, and each Ar is a polymerizable group P 2 is bonded to.

[0054] In a further preferred embodiment, Q is "Sp 4 -Y-Sp 4 " wherein Y is a monocyclic or polycyclic alkane moiety having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, and Sp 4 is absent or is a linear alkylene chain having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, a branched alkylene chain having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, or an aromatic or heteroaromatic moiety having 3 to 14 carbon atoms, preferably an aromatic moiety having 6 to 14 carbon atoms, and each Sp 4 is a polymerizable group P 2 is bonded to.

[0055] In particularly preferred embodiments, Q is [ka] is selected from.

[0056] Particularly preferred organic compounds are [ka] is selected from the group consisting of:

[0057] A preferred polyhedral silsesquioxane compound used as the second monomer has the following structure: [ka] (Structure 1) wherein: R is H, C1-C6-alkyl, C2-C6-alkenyl, C6-C 10 -aryl or C1-C6-alkoxy, L is C1~C 12 -Alkylene or C1-C 12 -oxyalkylene, more preferably C1-C6-alkylene or C1-C6-oxyalkylene, wherein one or more non-adjacent C atoms are independently -SiR 05 R 06 -, wherein R 05 and R 06 each independently of one another denotes H or alkyl having 1 to 6 C atoms, more preferably H, CH or CHCH, P 2 represents a polymerizable group (P) as defined above, y is an integer from 6 to 12, x is an integer from 2 to 12, and yx≧0.

[0058] Preferred C1-C6-alkyl substituents are methyl, ethyl, propyl, butyl, pentyl and hexyl. Preferred C2-C6-alkenyl substituents are ethenyl, propenyl, butenyl, pentenyl, and hexenyl. Preferred C6 to C 10 The aryl substituents are phenyl, tolyl, xylyl, and naphthyl. Preferred C1-C6-alkoxy substituents are methoxy, ethoxy, propoxy, butoxy, pentoxy and hexoxy. Preferred C1 to C 12 The alkylene substituents are methylene, ethylene, propylene, butylene, pentylene, and hexylene. Preferred C1 to C 12 The -oxyalkylene substituents are methyleneoxy, ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, and hexyleneoxy. Preferred C1-C4-alkyl substituents are methyl, ethyl, propyl and butyl.

[0059] In a particularly preferred embodiment, the group L in structure (1) is —(CH) n -, -O-(CH2) n -, -SiH2-(CH2) n -, -OSiH2-(CH2) n -, -Si(CH3)2-(CH2) n -, -OSi(CH3)2-(CH2) n -, -Si(CH2CH3)2-(CH2) n -, and -OSi(CH2CH3)2-(CH2) n -, wherein n is an integer of 1 to 6, preferably 2 to 4, and more preferably 3.

[0060] Particularly preferred polyhedral silsesquioxane compounds have the following structures 2 to 5: [ka] (Structure 2) [ka] (Structure 3) [ka] (Structure 4) [ka] (Structure 5) where x R substituents are selected from x (-LP 2 ) has been replaced by In the structure, R, L, and P 2 has the same meaning as defined above, and x is an integer from 2 to 6 in Structure 2, x is an integer from 2 to 8 in Structure 3, x is an integer from 2 to 10 in Structure 4, and x is an integer from 2 to 12 in Structure 5.

[0061] The polyhedral silsesquioxane compounds shown above can be readily prepared from available precursors and easily incorporated into polymerizable mixtures under suitable mixing conditions. For example, maleimide-substituted polyhedral silsesquioxanes and their preparation are described in U.S. Patent Application Publication No. 2006 / 0009578, the disclosure of which is incorporated herein by reference.

[0062] Preferred functionalized inorganic nanoparticles used as the second monomer have polymerizable groups P on their surface. 2 are inorganic nanoparticles containing P 2 denotes the polymerizable group (P) as defined above. Preferred polymerizable groups (P) of the functionalized inorganic nanoparticles are selected from maleimide groups, dimethylmaleimide groups, acrylate groups, methacrylate groups, allyl ether groups, and vinyl ether groups, which are attached to the surface of the inorganic nanoparticles either directly or via groups L.

[0063] Preferred functionalized inorganic nanoparticles have the following structure: [ka] (Structure 6) [ka] (Structure 7) wherein: [ka] represents inorganic nanoparticles, P 2 represents a polymerizable group (P), L is C1~C 12 -Alkylene or C1-C 12 -oxyalkylene, more preferably C1-C6-alkylene or C1-C6-oxyalkylene; x is an integer ≧2.

[0064] Preferred materials for the inorganic nanoparticles are selected from SiO2, TiO2, ZrO2, Fe2O3, MgTiO3, CaTiO3, SrTiO3, and BaTiO3. The inorganic nanoparticles may be solid or hollow.

[0065] Particularly preferred functionalized inorganic nanoparticles for use as the second monomer in the present invention are [ka] where L and x are defined as above. The above listing of functionalized inorganic nanoparticles is for illustrative purposes only and should not be construed as limiting.

[0066] The functionalized inorganic nanoparticles used as the second monomer in the present invention preferably have a degree of functionalization of 0.001 to 5 mmol / g, more preferably 0.01 to 1 mmol / g, and most preferably 0.05 to 0.5 mmol / g. The degree of functionalization is defined as the percentage of polymerizable groups P per unit mass of the functionalized inorganic nanoparticles. 2 The molar amount of The degree of functionalization can vary depending on the conditions for functionalizing inorganic nanoparticles. Those skilled in the art can select suitable conditions for functionalizing inorganic nanoparticles from known procedures in the literature, so that they can prepare individually tailored functionalized nanoparticles with different polymerizable groups and different degrees of functionalization. Suitable functionalized inorganic nanoparticles and their precursors can also be obtained from commercial sources, such as Sigma Aldrich (e.g., 3-aminopropyl-functionalized silica, 660442 Aldrich) or nanoComposix, Inc., San Diego, USA.

[0067] The present invention further provides a method for forming a copolymer comprising repeat units derived from a first monomer and repeat units derived from a second monomer, the copolymer being a dielectric copolymer which may be linear or crosslinked.

[0068] The method for forming the copolymer comprises: (i) providing a polymerizable mixture according to the present invention; and (ii) polymerizing the polymerizable mixture to obtain a copolymer. Includes: The polymerizable mixture contains the first monomer and the second monomer as defined above. The total content of the first monomer in the polymerizable mixture is preferably 50 to 99.9% by mass, more preferably 80 to 99% by mass, and most preferably 90 to 95% by mass, based on the total mass of the polymerizable monomers. The total content of the second monomer in the polymerizable mixture is preferably 0.1 to 50% by mass, more preferably 1 to 20% by mass, and most preferably 5 to 10% by mass, based on the total mass of the polymerizable monomers.

[0069] Preferably, the polymerizable mixture provided in step (i) is substantially free of solvent. By substantially free of solvent, it is meant that the total residual solvent content in the polymerizable starting material is 10% by weight or less, preferably 5% by weight or less, and more preferably 1% by weight or less, based on the total weight of the polymerizable monomers. Alternatively, the polymerizable mixture provided in step (i) preferably contains one or more solvents in an amount greater than 10% by weight, more preferably greater than 25% by weight, and most preferably greater than 50% by weight, based on the total weight of the polymerizable monomers. The polymerizable mixture is preferably polymerized in step (ii) by a radical or ionic chain polymerization reaction or a polyaddition reaction. Preferred polyaddition reactions are cycloadditions such as 2+2 cycloaddition, 4+2 cycloaddition (Diels-Alder reaction), or 1,3-dipolar cycloaddition, or nucleophilic additions such as the Michael reaction.

[0070] The above-mentioned reaction types and associated reaction conditions (eg, catalysts, solvents, temperatures, times, concentrations, etc.) are known to those skilled in the art. For example, radical or ionic polymerization can be carried out in the presence of a radical or ionic polymerization initiator that can be thermally and / or photochemically activated. Those skilled in the art are familiar with suitable radical and ionic polymerization initiators. For example, cycloaddition can be carried out photochemically or in the presence of a Lewis acid. Those skilled in the art are familiar with suitable photochemical conditions and suitable Lewis acids.

[0071] Preferably, the polymerizable mixture provided in step (i) further comprises one or more radical initiators. Preferred radical initiators are thermally activated radical initiators and / or photochemically activated radical initiators. Preferred thermally activated radical initiators are tert-amyl peroxybenzoate, 4,4-azobis(4-cyanovaleric acid), 1,1'-azobis(cyclohexanecarbonitrile), 2,2'-azobisisobutyronitrile (AIBN), benzoyl peroxide, 2,2-bis(tert-butylperoxy)butane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane, 2,5-bis(tert-butylperoxy)-2,5-dimethyl-3-hexyne, bis(1-(tert-butylperoxy)-2,5-dimethyl-3-hexyne), ... (tert-butylperoxy)-1-methylethyl)benzene, 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, tert-butyl hydroperoxide, tert-butyl peracetate, tert-butyl peroxide, tert-butyl peroxybenzoate, tert-butylperoxyisopropyl carbonate, cumene hydroperoxide (CHP), cyclohexanone peroxide, dicumyl peroxide (DCP), lauroyl peroxide, 2,4-pentanedione peroxide, peracetic acid, and potassium persulfate.

[0072] Preferred photochemically activated radical initiators are acetophenone, p-anisil, benzil, benzoin, benzophenone, 2-benzoylbenzoic acid, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone, benzoin methyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin ethyl ether, 4-benzoylbenzoic acid, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'biimidazole, methyl 2-benzoylbenzoate, 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone, (±)-camphorquinone, 2-chlorothioxanthone, 4,4'-dichlorobenzophenone, The compounds are 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,4-diethylthioxanthen-9-one, diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, 1,4-dibenzoylbenzene, 2-ethylanthraquinone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone, 2-isopropylthioxanthone, lithium phenyl(2,4,6-trimethylbenzoyl)phosphineate, 2-methyl-4'-(methylthio)-2-morpholino-propiophenone, 2-isonitrosopropiophenone, 2-phenyl-2-(p-toluenesulfonyl-oxy)acetophenone, and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide. Typically, such initiators are radical polymerization initiators that can be photochemically activated.

[0073] Further preferred photochemically activated radical initiators are [ka] JPEG0007729013000049.jpg171170 The file is TIFF0007729013000050.tif53170.

[0074] Preferably, the initiator of the radical polymerization is activated thermally by exposure to heat or photochemically by exposure to radiation such as UV and / or visible light. The exposure to heat preferably includes exposure to high temperatures in the range of 40 to 200°C, more preferably 50 to 180°C. Exposure to radiation includes exposure to visible light and / or UV light. Visible light is preferably electromagnetic radiation having a wavelength of >380-780 nm, more preferably >380-500 nm. UV light is preferably electromagnetic radiation having a wavelength of ≦380 nm, more preferably 100-380 nm. More preferably, UV light is selected from UV-A light having a wavelength of 315-380 nm, UV-B light having a wavelength of 280-315 nm, and UV-C light having a wavelength of 100-280 nm.

[0075] The UV light source can be a Hg vapor lamp or a UV laser, the IR light source can be a ceramic radiator or an IR laser diode, and for light in the visible range a laser diode. Preferred UV light sources are either a) single wavelength radiation with a maximum wavelength of <255 nm, such as 254 nm and 185 nm Hg low pressure discharge lamps, 193 nm ArF excimer lasers, and 172 nm Xe lasers, or b) broad wavelength distribution radiation with wavelength components <255 nm, such as undoped Hg low pressure discharge lamps. In a preferred embodiment of the invention, the light source is a xenon flashlight. Preferably, the xenon flashlight has a broad emission spectrum with a short wavelength component down to about 200 nm.

[0076] Preferably, the polymerization in step (ii) is carried out for a time range of at most 5 hours, more preferably at most 1 hour, most preferably at most 0.5 hours. It is further preferred that the polymerization of the polymerizable mixture in step (ii) is carried out at an elevated temperature, preferably in the range of 25 to 200°C, more preferably in the range of 25 to 150°C. There is further provided a copolymer obtainable or obtainable by the above-described method for forming a copolymer according to the present invention. The copolymer is preferably a linear copolymer or a crosslinked copolymer, more preferably a linear copolymer. Also provided is a copolymer comprising at least one repeat unit derived from a first monomer and at least one repeat unit derived from a second monomer, as defined above.

[0077] More preferably, the repeat unit derived from the first monomer of the copolymer is represented by the following formula (5): [-Sp 1 -(MG-Sp 1 ) m -] Formula (5) wherein Sp 1 , MG, and m have one of the definitions above. Preferably, the copolymers according to the invention have a molecular weight M, determined by GPC, of ​​at least 2000 g / mol, more preferably at least 4,000 g / mol, and even more preferably at least 5000 g / mol. w Preferably, the copolymer has a molecular weight M w More preferably, the molecular weight M of the copolymer is less than 50,000 g / mol. w is in the range of 5,000 to 20,000 g / mol.

[0078] Further provided is an electronic device comprising a copolymer according to the present invention, wherein the copolymer preferably forms a dielectric layer, more preferably a dielectric layer forming part of a redistribution layer, which serves to electrically isolate one or more electronic components that are part of the electronic device from each other.

[0079] Finally, there is provided a manufacturing method for preparing a packaged microelectronic structure in which a substrate is provided with a dielectric layer, the method comprising: (1) applying a polymerizable mixture according to the present invention to the surface of a substrate; and (2) curing the polymerizable mixture to form a dielectric layer. A method is provided which includes:

[0080] Preferably, the polymerizable mixture further comprises one or more inorganic filler materials. Preferred inorganic filler materials are selected from nitrides, titanates, diamonds, oxides, sulfides, sulfites, sulfates, silicates, and carbides, which may optionally be surface-modified with a capping agent. More preferably, the filler material is selected from the list consisting of AlN, Al2O3, BN, BaTiO3, BO3, Fe2O3, SiO2, TiO2, ZrO2, PbS, SiC, diamond, and glass particles. Preferably, the total content of inorganic filler materials in the polymerizable mixture is in the range of 0.001 to 90 mass %, more preferably 0.01 to 70 mass %, most preferably 0.01 to 50 mass %, based on the total mass of the polymerizable mixture.

[0081] The polymerizable mixture applied in step (1) is preferably substantially free of solvent, which means that the total residual solvent content in the polymerizable mixture is 10% by mass or less, preferably 5% by mass or less, and more preferably 1% by mass or less, based on the total mass of the polymerizable monomers. However, depending on the type of application method used to apply the polymerizable mixture in step (1), it is preferred that the polymerizable mixture comprises one or more solvents in an amount of preferably greater than 10% by weight, more preferably greater than 25% by weight, and most preferably greater than 50% by weight, based on the total weight of polymerizable monomers. The method for applying the polymerizable mixture in step (1) is not particularly limited. Preferred application methods in step (1) include dispensing, dipping, screen printing, stencil printing, roller coating, spray coating, slot coating, spin coating, stereolithography, gravure printing, flexographic printing, and inkjet printing.

[0082] The polymerizable mixture of the present invention can be provided in the form of a formulation suitable for gravure, flexographic and / or inkjet printing. For the preparation of such a formulation, ink-based formulations known in the state of the art can be used. Alternatively, the polymerizable mixture of the present invention may be provided in the form of a formulation suitable for photolithography. The photolithography process allows the creation of a photopattern by transferring a geometric pattern from a photomask to a photocurable composition using light. Typically, such photocurable compositions contain a photochemically activatable radical polymerization initiator. To prepare such a formulation, photoresist-based formulations known in the art can be used.

[0083] The layer of the polymerizable mixture applied in step (1) preferably has an average thickness of 1 to 50 μm, more preferably 2 to 30 μm, and most preferably 3 to 15 μm. The curing in step (2) is preferably carried out by a radical or ionic chain polymerization or polyaddition reaction. Preferred polyaddition reactions are cycloadditions such as 2+2 cycloaddition, 4+2 cycloaddition (Diels-Alder reaction), or 1,3-dipolar cycloaddition, or nucleophilic additions such as the Michael reaction. Preferred curing conditions correspond to the preferred polymerization conditions as given above for the method for forming the copolymer. Preferably, the polymerizable mixture applied in step (1) further comprises one or more radical initiators. Preferred radical initiators are described above. Microelectronic devices are also provided that include packaged microelectronic structures prepared according to the above-described manufacturing methods.

[0084] The present invention is further illustrated by the following examples, which should not be construed as limiting in any way. Those skilled in the art will recognize that various modifications, additions, and variations can be made to the present invention without departing from the spirit and scope of the invention, as defined in the appended claims. Another aspect of the present invention may be as follows. [1] A polymerizable mixture comprising a first monomer and a second monomer, The first monomer is one or more compounds represented by formula (1): the second monomer is one or more di- or polyfunctional compounds capable of reacting with the first monomer to form a copolymer; Equation (1) is P 1 -Sp 1 -(MG-Sp 1 ) m -P 1 Formula (1) where: m is an integer from 1 to 60; P 1 teeth, TIFF0007729013000051.tif2626 wherein V 1 is H and V 2 is alkyl having 1 to 6 carbon atoms, F, Cl, or CN, or V 1 and V 2 are each independently an alkyl having 1 to 6 carbon atoms, F, Cl, or CN; Sp 1 represents, at each occurrence, a spacer group (Sp) or a single bond; MG preferably has the formula (2): -(A 21 -Z 21 ) k -A 22-(Z 22 -A 23 ) l - Formula (2) is a rod-shaped mesogenic group selected from the formula: A 21 ~A 23 are independently, and in each occurrence independently of one another, an aryl group, a heteroaryl group, a heterocyclic group, an alicyclic group, or a cyclic imide group, which may be substituted by one or more identical or different groups L; Z 21 and Z 22 are independently and in each occurrence independently of one another -O-, -S-, -CO-, -COO-, -OCO-, -S-CO-, -CO-S-, -O-COO-, -CONR 01 -, -NR 01 -CO-, -NR 01 -CO-NR 02 , -NR 01 -CO-O-, -O-CO-NR 01 -, -OCH 2 -, -CH 2 O, -SCH 2 -, -CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CH 2 CH 2 -, -(CH 2 ) 4 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 -, -CH=N-, -N=CH-, -N=N-, -CH=CR 01 -, -CY 01 =CY 02 -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond; R 01 and R 02 each independently represent H or alkyl having 1 to 12 C atoms, L is F, Cl, Br, I, -CN, -NO 2 , -NCO, -NCS, -OCN, -SCN, -C(=O)NR xx R yy , -C(=O)OR xx , -C(=O)R xx , -NR xxR yy , -OH, -SF 5 or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy having 1 to 20 C atoms, wherein one or more H atoms may be replaced by F, or Cl, —CN, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy having 1 to 6 C atoms; R xx and R yy denote, independently of one another, H or alkyl having 1 to 12 C atoms, Y 01 and Y 02 each independently represent H, an alkyl having 1 to 12 carbon atoms, an aryl, F, Cl or CN, k and l are each and independently 0, 1, 2, 3, or 4; Polymerizable mixture. [2] The spacer group Sp is a radical "P 1 -Sp 1 -" is the formula "P 1 -Sp'-X'-" During the ceremony, Sp' is (a) a linear or branched alkylene having 1 to 40, preferably 1 to 30, carbon atoms, which is mono- or polysubstituted by F, Cl, Br, I, or CN, and in addition has one or more non-adjacent CH 2 The groups may each independently be —O—, —S—, —NH—, —NR—, so that the O atoms and / or S atoms are not directly linked to each other. 01 -, -SiR 01 R 02 -, -CO-, -COO-, -OCO-, -OCO-O-, -S-CO-, -CO-S-, -NR 01 -CO-O-, -O-CO-NR 01 -, -NR 01 -CO-NR 01 a straight or branched alkylene optionally replaced by -, -CH=CH-, or -C≡C-; (b)-Sp x -G-Sp y -wherein Sp x and Sp y are each independently an alkylene having 1 to 20 C atoms or a single bond, and G represents a cycloalkylene having 3 to 20 C atoms which may be mono- or polysubstituted by an alkyl having 1 to 20 C atoms. -Sp x -G-Sp y - indicates X' is -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CONR 01 -, -NR 01 -CO-, -NR 01 -CO-NR 01 -, -OCH 2 -, -CH 2 O-, -SCH 2 -, -CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 -, -CH=N-, -N=C-, -N=N-, -CH=CR 01 -, -CY 01 =CY 02 represents -, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, or a single bond; R 01 and R 02 each independently represent H or alkyl having 1 to 12 C atoms, Y 01 and Y 02 each independently represent H, F, Cl or CN, The polymerizable mixture according to [1] above. [3] The spacer group Sp is —(CH 2 ) p1 -, -(CH 2 CH 2 O) q1 -CH 2 CH 2 -, -CH 2 CH 2 -S-CH 2 CH 2 -, -CH 2 CH 2 -NH-CH 2 CH 2 -, -(SiR 01 R 02 -O) p1 -, -(CH 2 ) p1 -(Cyclo-C 6 H 8 R 01 R 02 )-(CH 2 ) p1 - and TIFF0007729013000052.tif2631 wherein: p1 is an integer from 1 to 60, q1 is an integer from 1 to 12, R 01 and R 02 each independently of one another denotes H or alkyl having 1 to 12 C atoms, The polymerizable mixture according to [1] or [2] above. 〔4〕A 21 ~A 23 may, independently and, if appearing multiple times, independently of one another, be any of the following groups a) to e): a) One or more non-adjacent channels 2 trans-1,4-cyclohexylene, 1,4-cyclohexenylene, and 4,4′-bicyclohexylene, in which groups may be replaced by —O— and / or —S— and in which one or more H atoms may be replaced by a group L; b) 1,4-phenylene, 1,3-phenylene, 4,4'-biphenylene, 2,5-thiophene, and 2,6-dithieno[3,2-b:2',3'-d]thiophene, in which one or two CH groups may be replaced by N and one or more H atoms may be replaced by a group L; c) tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobuta-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl, and selenophene-2,5-diyl, optionally substituted by one or more groups L; d) saturated, partially unsaturated or fully unsaturated and optionally substituted polycyclic radicals having 5 to 20 ring C atoms, one or more of which may also be replaced by heteroatoms, preferably bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, TIFF0007729013000053.tif79150 TIFF0007729013000054.tif143170 is selected from in which one or more H atoms may be replaced by a group L, and / or one or more double bonds may be replaced by a single bond, and / or one or more CH groups may be replaced by N, M is -O-, -S-, -CH 2 -, -CHY 03 - or -CY 03 Y 04 - indicates Y 03 、Y 04 are, independently of each other, R 01 One of the meanings given above for F, Cl, CN, OCF 3 , or CF 3 , preferably H, F, Cl, CN, OCF 3 , or CF 3 indicates, W 5 、W 6 are, independently of each other, -CH 2 CH 2 -, -CH=CH-, -CH 2 -O-, O-CH 2 -, -C(R c R d )- or -O-, R c 、R d denote, independently of one another, H or alkyl having 1 to 6 C atoms, preferably H, methyl or ethyl, R 03 、R 04 are polycyclic radicals, independently of one another, denoting H, F, straight-chain or branched alkyl having 1 to 12 C atoms, in which one or more H atoms may be replaced by F; e) TIFF0007729013000055.tif37150 A cyclic imide selected from the group consisting of: Cyclic imides in which one or more H atoms may be replaced by a group L, and / or one or more double bonds may be replaced by a single bond, and / or one or more CH groups may be replaced by N. The polymerizable mixture according to any one of the above items [1] to [3], wherein the polymerizable mixture represents a moiety selected from the group consisting of: [5] The polymerizable mixture according to any one of [1] to [4], wherein the second monomer is one or more bifunctional or polyfunctional compounds selected from organic compounds, polyhedral silsesquioxane compounds, and functionalized inorganic nanoparticles. [6] The second monomer is preferably a P-type monomer, preferably a P-type monomer, by radical or ionic chain polymerization or 2+2 cycloaddition. 1 groups containing a C=C double bond that reacts with P in a 4+2 cycloaddition; 1 groups containing two conjugated C=C double bonds that react with P 1 and preferably reacts with P in a 1,3-dipolar cycloaddition. 1 The polymerizable mixture according to any one of the above [1] to [5], wherein the polymerizable mixture is one or more bifunctional or polyfunctional compounds containing two or more polymerizable groups (P) selected from 1,3-dipolar groups that react with [7] The second monomer is (a) Equation (4): TIFF0007729013000056.tif1621 Formula (4) An organic compound represented by the formula: Q is a hydrocarbon group having 1 to 50 carbon atoms, which may be substituted with one or more substituents L, where L is as defined in any one of the above items [1] to [6] and optionally represents a hydrocarbon group which may contain one or more heteroatom groups selected from N, O, and S; P 2 represents the polymerizable group (P) as defined in [6] above, an organic compound, wherein x is an integer from 2 to 10; (b) the following structure: TIFF0007729013000057.tif1856 Structure (1) A polyhedral silsesquioxane compound represented by the formula: R is H, C 1 ~C 6 -Alkyl, C 2 ~C 6 -Alkenyl, C 6 ~C 10 -aryl or C 1 ~C 6 -alkoxy, L is C 1 ~C 12 -Alkylene or C 1 ~C 12 -oxyalkylene, in which one or more non-adjacent C atoms are independently -SiR 05 R 06 -, wherein R 05 or R 06 each independently represent H or alkyl having 1 to 6 C atoms, P 2 represents the polymerizable group (P) as defined in [6] above, a polyhedral silsesquioxane compound, wherein y is an integer of 6 to 12, x is an integer of 2 to 12, and yx≧0; or (c) a polymerizable group P on its surface 2 1. A functionalized inorganic nanoparticle comprising: P 2 represents a polymerizable group (P) as defined in [6] above, functionalized inorganic nanoparticles The polymerizable mixture according to [6] above, which is one or more of the following: [8] A method for forming a copolymer, comprising: (i) preparing the polymerizable mixture according to any one of the above items [1] to [7]; and (ii) polymerizing the polymerizable mixture to obtain a copolymer. A method comprising: [9] The method for forming a copolymer according to [8], wherein the polymerizable mixture further comprises one or more radical initiators.

[10] A copolymer obtainable by the method for forming a copolymer according to [8] or [9] above.

[11] A copolymer comprising at least one repeating unit derived from the first monomer and at least one repeating unit derived from the second monomer, as defined in any one of [1] to [7] above.

[12] The repeating unit derived from the first monomer is represented by formula (5): [-Sp 1 -(MG-Sp 1 ) m -] Formula (5) wherein Sp 1 The copolymer according to

[11] above, wherein , MG, and m are as defined in any one of [1] to [7] above.

[13] An electronic device comprising the copolymer according to any one of

[10] to

[12] above.

[14] The electronic device according to

[13] , wherein the copolymer forms a dielectric layer.

[15] A manufacturing method for preparing a packaged microelectronic structure in which a substrate is provided with a dielectric layer, comprising: (1) applying the polymerizable mixture according to any one of the above items [1] to [7] to the surface of a substrate; and (2) curing the polymerizable mixture to form a dielectric layer. A manufacturing method comprising:

[16] The manufacturing method for preparing a packaged microelectronic structure according to

[15] , wherein the polymerizable mixture further comprises one or more radical initiators.

[17] A microelectronic device comprising a packaged microelectronic structure obtainable by the manufacturing method according to

[15] or

[16] .

[0085] Example Synthesis of host material oligomers Synthesis of oligomer 4 [ka] Step 1: Triethylamine (49.7 g, 0.49 mol) was dissolved in 0.7 L of anhydrous toluene, followed by the addition of methanesulfonic anhydride (48.6 g, 0.5 mol). The mixture was stirred at room temperature for 10 min, after which diamine 2 (Priamine®, Croda, 77.4 g, 0.14 mol) and dianhydride 1 (50 g, 0.07 mol) were carefully added. The reaction mixture was then heated to reflux for 12 h using a Dean-Stark apparatus.

[0086] Step 2: The reaction mixture was cooled to room temperature and maleic anhydride (8.7 g, 0.09 mol) was slowly added, followed by an additional 10 g of methanesulfonic anhydride. The mixture was reheated to reflux using a Dean-Stark trap for approximately 12 hours. After cooling to room temperature, an additional 200 ml of toluene was added and stirring was stopped. The upper (toluene solution) fraction was carefully separated and the salt fraction was washed twice with toluene (2 x 500 ml). The toluene solutions were combined and filtered through a glass funnel tightly packed with silica gel. The silica gel was washed with an additional 100 ml of toluene, and the toluene was removed under reduced pressure to yield 70 g (85%) of a yellow waxy resin.

[0087] Synthesis of oligomer 5 [ka] Dimethylmaleic anhydride (ABCR, 20 g, 0.16 mol) was slowly added to the reaction mixture of compound 3 (synthesis described in Step 1), followed by an additional 10 g of methanesulfonic anhydride. The mixture was reheated to reflux using a Dean-Stark trap for approximately 12 hours. After cooling to room temperature, an additional 200 ml of toluene was added and stirring was stopped. The upper (toluene solution) fraction was carefully separated, and the salt fraction was washed twice with toluene (2 × 500 ml). The combined toluene solutions were filtered through a glass funnel tightly packed with silica gel. The silica gel was washed with an additional 100 ml of toluene, and the toluene was removed under reduced pressure to yield 87 g of a yellow waxy resin.

[0088] B) Synthesis of additives Synthesis of Tris-(2-maleimidoethyl)-amine (6) [ka] Step 1: Furan-maleic anhydride adduct (Alfa Aesar, 28.5 g, 0.17 mol) was dissolved in 750 ml of methanol. Tris(2-aminoethyl)amine (Alfa Aesar, 5 g, 0.03 mol) dissolved in 250 ml of methanol was added dropwise at 0°C. The reaction mixture was then heated at reflux for 4 hours. The methanol was removed and the concentrated solution (approximately 350 ml) was allowed to stand overnight at 4°C to crystallize. The resulting yellow crystals were filtered and washed with ethyl acetate (19.6 g, 38%).

[0089] Step 2: 7.4 g (0.013 mol) of the product from Step 1 was dissolved in 300 ml of toluene. The solution was heated to reflux. After 20 h, the solvent was removed under reduced pressure and the remaining solid was dissolved in ethyl acetate and purified by flash chromatography (DCM / ethyl acetate 60 / 40). Yield: 4 g (84%). 1 H-NMR (500MHz, CDCl3): δ=6.68(s,6H), 3.52(t,J=6.6Hz,6H), 2.71(t,J=6.6Hz,6H)ppm.

[0090] Synthesis of 1,1',1''-(nitrilotris(ethane-2,1-diyl))tris(3,4-dimethyl-1H-pyrrole-2,5-dione) (7) [ka] Tris(2-aminoethyl)amine (Alfa Aesar, 10 g, 0.066 mol) was slowly added dropwise to glacial acetic acid (75 ml) at 0°C. 2,3-Dimethylmaleic anhydride (Merck, 25.9 g, 0.199 mol) was added, and the reaction mixture was heated to reflux. After 20 h, ethyl acetate (750 ml) and water (375 ml) were added, the phases were separated, and the aqueous solution was washed twice with ethyl acetate. The combined organic phases were washed with NaOH (1N, 2 x 250 ml) and brine (250 ml) and dried over NaSO. After filtration, the solvent was removed under reduced pressure, and the residual solid was purified by chromatography (SiO, toluene / ethyl acetate (2:1, v / v)). Yield: 26 g (83%) as a white solid. 1 H-NMR (500MHz, CDCl3): δ=3.49(t, J=6.7Hz, 6H), 2.70(t, J=6.7Hz, 6H), 1.94(s, 18H)ppm.

[0091] C) Formulations & Preparation of Freestanding Films General procedure for preparation of formulations: A toluene solution (25% by weight) of oligomer 4 or 5 was mixed with various amounts of additives (dissolved in DMAc or cyclopentanone, as appropriate) and an appropriate amount of radical initiator.

[0092] Preparation of free-standing films: Free-standing polymer films were prepared on glass substrates by doctor blade method with either thermal or light-induced curing (see various examples for more specific conditions). The films could be removed from the glass substrate by rinsing the polymer with water.

[0093] Mechanical and thermal properties: Tensile strength and elongation at break (E2B) were measured using a mechanical testing machine (500N Zwicki). Young's modulus (elastic modulus) was calculated by dividing the tensile stress by the extensional strain in the elastic (initial, linear) portion of the mechanical stress-strain curve. Film dimensions were typically 25 mm long, 15 mm wide, and 25-100 μm thick. Measurements were performed according to the following set of parameters: pre-measurement: 0.1 N at an extension rate of 10 mm / min; main extension rate of 50 mm / min. All experiments were performed at room temperature (23±2°C). Thermomechanical analysis (TMA) was performed on a 402F3 TMA (Netzsch) in tension mode. The coefficient of thermal expansion (CTE) was measured in the temperature range of 20–300 °C under N2 atmosphere.

[0094] Example 1: Oligomer 4 or 5 and 1,1′-(methylenedi-4,1-phenylene)-bismaleimide (Aldrich, BMI1) [ka] (a) Curing conditions: Oligomer 4 or 5 + 10% by weight BMI1; 10 minutes at room temperature + 100°C for 10 minutes (hot plate), 10 J / cm 2 (broadband), 175°C for 30 minutes (hot plate). [Table 1] # CTE at 140-170°C. Cured films of Oligomer 5 with 10 wt% BMI1 exhibited a nearly three-fold higher Young's modulus while exhibiting higher stretchability (E2B) compared to the blend with Oligomer 4. Additionally, the CTE was dramatically reduced into the favorable region. (b) Curing conditions: Oligomer 4 or 5 + 10% by mass BMI1 + 5% by mass Irgacure OXE-02 (BASF), 10 minutes at room temperature + 100°C for 10 minutes (hot plate), 10 J / cm 2 (broadband), 175°C for 30 minutes (hot plate). [Table 2] # CTE at 140-170°C.

[0095] The cured film of Oligomer 5 with OXE-02 and 10 wt% BMI1 showed higher stretchability in addition to lower CTE values. (c) Curing conditions: Oligomer 4 or 5 + 10% by weight BMI1 + 5% by weight Irgacure OXE-02 (BASF) + 5% by weight dicumyl peroxide (Aldrich), 10 minutes at room temperature + 100°C for 10 minutes (hot plate), 10 J / cm 2 (broadband), 175°C for 30 minutes (hot plate). [Table 3] # CTE at 140-170°C.

[0096] Cured films of Oligomer 5 and 10 wt% BMI1 using a radical thermal initiator in combination with a photoinitiator (OXE-02) showed more favorable values ​​in terms of modulus, E2B, and CTE. (d) Curing conditions: Oligomer 5 + 10% by mass BMI1 + 5% by mass N1919T (Adeka), 10 minutes at room temperature + 100°C for 10 minutes (hot plate), 10 J / cm 2 (broadband), 175°C for 30 minutes (hot plate). [Table 4] # CTE at 140-170°C. (e) Curing conditions: Oligomer 5 + 10% by weight BMI1 + 5% by weight N1919T (Adeka) + 5% by weight dicumyl peroxide (Aldrich), 10 minutes at room temperature + 100°C for 10 minutes (hot plate), 10 J / cm 2 (broadband), 175°C for 30 minutes (hot plate). [Table 5] # CTE at 140-170°C.

[0097] Example 2: Oligomer 4 or 5 and Maleimide 6 [ka] Curing conditions: Oligomer 4 or 5 + 5% by weight maleimide 6, 10 minutes at room temperature, 10 minutes at 100°C (hot plate), 10 J / cm 2 (broadband), 175°C (hotplate) for 30 minutes. [Table 6] # CTE at 25-35°C. Cured films of oligomer 5 with 5 wt. % maleimide 6 showed more favorable values ​​for modulus, E2B, and CTE compared to oligomer 4.

[0098] Example 3: Oligomer 4 or 5 and Dimethylmaleimide 7 [ka] Curing conditions: Oligomer 4 or 5 + 5% by weight dimethylmaleimide 7, 10 minutes at room temperature, 10 minutes at 100°C (hot plate), 10 J / cm 2 (broadband), 175°C (hotplate) for 30 minutes. [Table 7] # CTE at 25-35°C.

[0099] Example 4: Oligomer 4 or 5 and 1,1′-(methylenedi-4,1-phenylene)-bismaleimide (Aldrich, BMI1) and dimethylmaleimide-SiO (50 nm, nanoComposix) [ka] Curing conditions: Oligomer 4 or 5 + 10% by weight BMI1 + 5% by weight DMMI-SiO2 (nanoComposix, Inc., 50 nm), 10 minutes at room temperature, 10 minutes at 100°C (hot plate), 10 J / cm 2 (broadband), 175°C (hotplate) for 30 minutes. [Table 8] # CTE at 140-170°C. Cured films of Oligomer 5 having the configuration described above exhibited significantly higher modulus values ​​in addition to favorable CTE values.

[0100] Example 5: Oligomer 4 or 5 and 1,1'-(methylenedi-4,1-phenylene)-bismaleimide (Aldrich, BMI1) and dimethylmaleimide-POSS (DMMI-POSS) [ka] Curing conditions: Oligomer 4 or 5 + 10% by weight BMI1 + 5% by weight DMMI-POSS, 10 minutes at room temperature, 10 minutes at 100°C (hot plate), 10 J / cm 2 (broadband), 175°C (hotplate) for 30 minutes. [Table 9] # CTE at 140-170°C.

Claims

1. A polymerizable mixture comprising a first monomer and a second monomer, The first monomer is one or more compounds represented by formula (1): the second monomer is one or more di- or polyfunctional compounds selected from organic compounds, polyhedral silsesquioxane compounds, and functionalized inorganic nanoparticles capable of reacting with the first monomer to form a copolymer; Equation (1) is P 1 -Sp 1 -(Mg-Sp 1 ) m -P 1 Formula (1) where: m is an integer from 1 to 60, P 1 teeth, 【Chemical 1】 wherein V 1 is H and V 2 is alkyl having 1 to 6 carbon atoms, F, Cl, or CN, or V 1 and V 2 are each independently an alkyl having 1 to 6 carbon atoms, F, Cl, or CN; Sp 1 In each occurrence, denotes a spacer group (Sp), and Sp is a radical "P 1 -Sp 1 -" is the formula "P 1 -Sp'-X'-" is selected from the formula Sp'-X', During the ceremony, Sp' is (a) a straight-chain or branched alkylene having 1 to 40 C atoms, which is mono- or polysubstituted by F, Cl, Br, I, or CN, and in addition has one or more non-adjacent CH 2 The groups may each independently be —O—, —S—, —NH—, —NR— such that the O atoms and / or S atoms are not directly linked to each other. 01 -, -SiR 01 R 02 -, -CO-, -COO-, -OCO-, -OCO-O-, -S-CO-, -CO-S-, -NR 01 -CO-O-, -O-CO-NR 01 -, -NR 01 -CO-NR 01 a straight-chain or branched alkylene optionally replaced by -, -CH=CH-, or -C≡C-; (b)-Sp x -G-Sp y - and Sp x and Sp y are each independently an alkylene having 1 to 20 carbon atoms or a single bond, and G represents a cycloalkylene having 3 to 20 carbon atoms which may be mono- or polysubstituted by an alkyl having 1 to 20 carbon atoms. -Sp x -G-Sp y - indicates X' is -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CONR 01 -, -NR 01 —CO—, —NR 01 -CO-NR 01 -, -OCH 2 -, -CH 2 O-, -SCH 2 -, -CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 -, -CH=N-, -N=C-, -N=N-, -CH=CR 01 -, -CY 01 =CY 02 represents -, -C≡C-, -CH═CH-COO-, -OCO-CH═CH-, or a single bond; R 01 and R 02 each independently of one another denotes H or alkyl having 1 to 12 C atoms, Y 01 and Y 02 each independently represents H, F, Cl, or CN, MG is expressed by the formula (2): -(A 21 -Z 21 ) k -A 22 -(Z 22 -A 23 ) l - Formula (2) is a rod-shaped mesogenic group selected from the formula: A 21 ~A 23 are independently, and in each occurrence independently of one another, an aryl group, a heteroaryl group, a heterocyclic group, an alicyclic group, or a cyclic imide group, which may be substituted by one or more identical or different groups L, Z 21 and Z 22 are independently and independently of one another in each occurrence -O-, -CO-, -COO-, -OCO-, -O-COO-, -OCH 2 -, -CH 2 O or a single bond, L is F, Cl, Br, I, -CN, or -NO 2 , -NCO, -NCS, -OCN, -SCN, -C(=O)NR xx R yy , -C(=O)OR xx , -C(=O)R xx , -NR xx R yy , —OH, —SF 5 or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 20 C atoms, in which one or more H atoms may be replaced by F, or Cl, —CN, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 6 C atoms, R xx and R yy denote, independently of one another, H or alkyl having 1 to 12 C atoms, k and l are each and independently 0, 1, 2, 3, or 4; The second monomer is (a) Formula (4): 【change】 Formula (4) The organic compound represented by the formula: Q is a hydrocarbon group having 1 to 50 carbon atoms, optionally substituted with one or more substituents L, where L optionally contains one or more heteroatoms selected from N, O, and S; P2 is 【change】 in which W 3 and W 4 each independently denote H, Cl or alkyl having 1 to 5 C atoms, the organic compound, wherein x is an integer of 2 to 10; (b) a molecule having the following structure: 【Chemistry 6】 Structure (1) The polyhedral silsesquioxane compound represented by the formula: R is H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 6 -C 10 -aryl or C 1 -C 6 -alkoxy, L is C 1 -C 12 -alkylene or C 1 -C 12 -oxyalkylene, in which one or more non-adjacent C atoms may, independently of one another, be replaced by —SiR 05 R 06 —, in which R 05 or R 06 each, independently of one another, denotes H or alkyl having 1 to 6 C atoms, P2 is 【change】 in which W 3 and W 4 each independently denote H, Cl or alkyl having 1 to 5 C atoms, The polyhedral silsesquioxane compound, wherein y is an integer of 6 to 12, x is an integer of 2 to 12, and y-x≧0; or (c) said functionalized inorganic nanoparticles comprising polymerizable groups P2 on their surface, P2 is 【change】 wherein W 3 and W 4 each independently represent H, Cl or alkyl having 1 to 5 C atoms. and one or more of: the total content of the first monomer is 80 to 99 mass% based on the total mass of the polymerizable monomers, and the total content of the second monomer is 1 to 20 mass% based on the total mass of the polymerizable monomers; Polymerizable mixture.

2. The spacer group Sp is —(CH 2 ) p1 -, -(CH 2 CH 2 O) q1 -CH 2 CH 2 -, -CH 2 CH 2 -S-CH 2 CH 2 -, -CH 2 CH 2 -NH-CH 2 CH 2 -, -(SiR 01 R 02 -O) p1 -, -(CH 2 ) p1 -(cyclo-C 6 H 8 R 01 R 02 )-(CH 2 ) p1 - and 【Chemistry 2】 wherein: p1 is an integer from 1 to 60, q1 is an integer from 1 to 12, R 01 and R 02 each independently of one another denotes H or alkyl having 1 to 12 C atoms, The polymerizable mixture of claim 1 .

3. A 21 ~A 23 independently and, if multiple, independently of one another, from the following group a) to e): a) One or more non-adjacent channels 2 trans-1,4-cyclohexylene, 1,4-cyclohexenylene, and 4,4′-bicyclohexylene, in which groups may be replaced by —O— and / or —S— and one or more H atoms may be replaced by a group L; b) 1,4-phenylene, 1,3-phenylene, 4,4′-biphenylene, 2,5-thiophene, and 2,6-dithieno[3,2-b:2′,3′-d]thiophene, in which one or two CH groups may be replaced by N and one or more H atoms may be replaced by a group L; c) tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobuta-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl, and selenophene-2,5-diyl, each optionally substituted by one or more groups L; d) saturated, partially unsaturated or fully unsaturated and optionally substituted polycyclic radicals having 5 to 20 ring C atoms, one or more of which may also be replaced by heteroatoms, such as bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, 【Chemistry 3】 【change】 is selected from in which one or more H atoms may be replaced by a group L, and / or one or more double bonds may be replaced by a single bond, and / or one or more CH groups may be replaced by N, M is -O-, -S-, or -CH 2 --, --CHY 03 - or -CY 03 Y 04 - indicates Y 03 , Y 04 are independently H, F, Cl, CN, OCF 3 , or CF 3 indicates, W 5 , W 6 are each independently —CH 2 CH 2 -, -CH=CH-, -CH 2 —O—, O—CH 2 -, -C(R c R d )- or -O-, R c , R d denote, independently of one another, H or alkyl having 1 to 6 C atoms, R 03 , R 04 are polycyclic radicals, independently of one another, denoting H, F, straight-chain or branched alkyl having 1 to 12 C atoms, in which one or more H atoms may be replaced by F; e) 【Chemistry 4】 A cyclic imide selected from the group consisting of: Cyclic imides in which one or more H atoms may be replaced by a group L, and / or one or more double bonds may be replaced by a single bond, and / or one or more CH groups may be replaced by N.

3. The polymerizable mixture of claim 1, wherein the polymerizable mixture exhibits a moiety selected from:

4. 1. A method for forming a copolymer, comprising: (i) providing a polymerizable mixture according to any one of claims 1 to 3, and (ii) polymerizing the polymerizable mixture to obtain a copolymer. A method comprising:

5. 5. The method for forming a copolymer of claim 4, wherein the polymerizable mixture further comprises one or more radical initiators.

6. A copolymer obtainable by the process for forming a copolymer according to claim 4 or 5.

7. A copolymer comprising at least one repeat unit derived from said first monomer and at least one repeat unit derived from said second monomer as defined in any one of claims 1 to 3.

8. The repeating unit derived from the first monomer is represented by formula (5): [-Sp 1 -(MG-Sp 1 ) m -] Formula (5) wherein Sp 1 8. The copolymer of claim 7, wherein , MG, and m are as defined in claim 1.

9. An electronic device comprising the copolymer of any one of claims 6 to 8.

10. The electronic device of claim 9 , wherein the copolymer forms a dielectric layer.

11. 1. A manufacturing method for preparing a packaged microelectronic structure in which a substrate is provided with a dielectric layer, comprising: (1) applying the polymerizable mixture according to any one of claims 1 to 3 to the surface of a substrate; and (2) curing the polymerizable mixture to form a dielectric layer. A manufacturing method comprising:

12. The method for preparing a packaged microelectronic structure of claim 11 , wherein the polymerizable mixture further comprises one or more radical initiators.

13. A microelectronic device comprising a packaged microelectronic structure obtainable by the manufacturing method according to claim 11 or 12.

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