Dielectric materials based on heteroaromatic extended bismaleimides.

Abstract

The present invention relates to a new class of dielectric polymer materials that are particularly suitable for the manufacture of electronic devices. The dielectric polymer materials are formed by reacting bismaleimide compounds and exhibit an advantageous balanced profile of favorable material properties. The bismaleimide compounds have an oligomeric structure with a heteroaromatic extended repeat unit in the center of the molecule and a maleimide group at each end of the molecule. A method for forming said dielectric polymer materials is further provided. Additionally, the present invention relates to dielectric polymer materials and electronic devices comprising the same.

Description

FIELD OF THEINVENTION

[0001] The present invention relates to a new class of dielectric polymer materials that are particularly suitable for the manufacture of electronic devices. The dielectric polymer materials are formed by reacting a new type of bismaleimide compounds, and exhibit an advantageous balanced profile of favorable material properties, especially in advanced electronic packaging applications, such as wafer level packaging (WLP), and with respect to the demand for low dielectric adhesive applications. The dielectric polymer materials of the present invention exhibit an advantageous balanced profile of material properties, including: (a) favorable thermomechanical properties, such as high thermal stability, high glass transition temperature (Tg), low coefficient of thermal expansion (CTE), high elongation at break and high tensile strength; (b) favorable dielectric properties, such as low dielectric constant and low dielectric loss tangent; (c) good adhesive properties, especially for copper and SiO2 passivated wafers; (d) low water absorption; and (e) good processability from solvents commonly used in the semiconductor industry.

[0002] The dielectric polymer material of the present invention is formed by reacting bismaleimide compounds. As bismaleimide compounds, certain heteroaromatic extended bismaleimide compounds are described herein. Such compounds can be photostructurized and used as starting materials for preparing repassivation layers in packaged electronic devices (including passivation of conductive or semiconducting components in redistribution layers (RDL) or die attach), in thin film formulations, and / or in adhesive formulations for various applications in electronic device manufacturing. In addition, the bismaleimide compounds have excellent film-forming ability and are easy to process to form dielectric polymers as spin-on materials.

[0003] The bismaleimide compounds of the present invention have an oligomeric structure with a heteroaromatic extended repeat unit in the center of the molecule and a maleimide group at each end of the molecule. The heteroaromatic extended repeat unit specifically includes a benzoxazole, benzothiazole and / or benzimidazole moiety.

[0004] Methods for forming said dielectric polymer material are further provided.The present invention further relates to dielectric polymer materials and electronic devices comprising said polymer material as a dielectric material.

[0005] The bismaleimide compounds and related dielectric polymer materials of the present invention enable cost-effective and reliable manufacture of microelectronic devices, significantly reducing the number of defective devices due to mechanical deformation (deflection) due to undesirable thermo-mechanical expansion. Background of the Invention

[0006] As solid-state transistors began to replace vacuum tube technology, electronic components such as resistors, capacitors, and diodes could be attached directly to the card's printed circuit board by their leads, thus establishing the basic building block or level of packaging still in use today. Complex electronic functions often require many more individual components than could be interconnected on a single printed circuit card. Multi-layer card capabilities were accompanied by the development of three-dimensional packaging of daughter cards onto multi-layer motherboards. Integrated circuits allow many of the discrete circuit elements, such as resistors and diodes, to be embedded into individual relatively small components known as integrated circuit chips or dies. However, despite the tremendous circuit integration, more than one level of packaging is typically required, due in part to the technology of the integrated circuit itself. Integrated circuit chips have extremely small terminals and are very fragile. The first level of packaging accomplishes the primary functions of providing the ability to mechanically protect, cool, and make electrical connections 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 is utilized, such as a printed circuit card. For very complex applications, such as mainframe computers, multiple hierarchies of packaging levels are required.

[0007] A wide variety of advanced packaging technologies exist to meet the requirements of today's semiconductor industry. Leading advanced packaging technologies - Wafer Level Packaging (WLP), Fan-Out Wafer Level Packaging (FOWLP), 2.5D interposer, Chip-on-Chip stacking, Package-on-Package stacking, Embedded ICs - all require structuring of thin substrates, redistribution layers and other components, e.g. high resolution interconnects. End consumer markets present a sustained demand for lower prices and higher functionality in ever smaller and thinner devices. This drives the need for next generation packaging with more sophisticated features and improved reliability at competitive manufacturing costs.

[0008] Wafer-level packaging (WLP) is one of the most promising semiconductor packaging technologies for the next generation of compact, high-performance electronic devices. Generally, WLP is the process of packaging integrated circuits while still being part of a wafer. This contrasts with the more conventional method of sawing the wafer into individual circuits and then packaging them. WLP is based on a redistribution layer (RDL), which allows for connections between the die and solder balls, resulting in improved signal propagation and smaller form factors (see Figure 1). The primary application areas for WLP are smartphones and wearables due to their size constraints.

[0009] With current materials, the WLP process is limited to medium chip size applications. The reasons for this limitation are the inadequate thermomechanical properties and non-optimized processing of these materials. The dielectric materials used in the next generation microchip RDL should meet certain requirements. In addition to low dielectric constant, several thermomechanical properties play an important role, such as high thermal stability, high glass transition temperature (Tg), low coefficient of thermal expansion (CTE), high elongation at break and high tensile strength.

[0010] An important class of materials that meets some of the above mentioned requirements are the imide-extended maleimide compounds, which have been described in various publications in the state of the art.

[0011] US2004 / 0225026A1 and US2011 / 0130485A1 relate to thermosetting (adhesive) compositions containing imide-extended mono-, bis- or polymaleimide compounds. The imide-extended maleimide compounds are prepared by condensing a suitable anhydride with a suitable diamine to produce amine-terminated compounds. These compounds are then condensed with an excess of maleic anhydride to yield the imide-extended maleimide compounds. When incorporated into thermosetting compositions, the imide-extended maleimide compounds are said to reduce brittleness and increase toughness in the compositions without sacrificing thermal stability.

[0012] US2011 / 0049731A1 and US2013 / 0228901A1 relate to materials and methods for stress reduction in semiconductor wafer passivation layers. Described are compositions containing low modulus photosensitive polyimides for use as passivation layers, and semiconductor wafers and devices containing passivation layers made therewith.

[0013] US2017 / 0152418A1 relates to maleimide adhesive films prepared from thermosetting maleimide resins containing imide-extended mono-, bis- and polymaleimide compounds. The maleimide adhesive films are said to be photostructurable and suitable for the production of electronic devices, integrated circuits, semiconductor devices, passive devices, solar cells, solar modules and / or light emitting diodes.

[0014] However, the imide-extended maleimide compounds mentioned above have poor solubility in common solvents used in industry and poor thermomechanical property profiles, such as low glass transition temperature (Tg) and high coefficient of thermal expansion (CTE). If material modifications are aimed at reducing the CTE in this material class, the material becomes too brittle and cannot be used in WLP applications.

[0015] Another trend in the semiconductor industry is related to the demand for materials with low dielectric properties (low dielectric constant, low dielectric loss tangent) in the high frequency range. The frequency of signals has increased with the increasing speed of signal transmission in printed circuit boards. In addition, the 5G era requires reliable materials with unique properties that meet specific requirements. In general, the adhesive strength to low dielectric materials is usually poor because the polarity of these insulating films is typically low. New materials that combine low-loss dielectric behavior with good adhesive properties are of great interest for the development of various future applications.

[0016] WO2019 / 141833A1 relates to dielectric polymers having excellent film-forming ability, excellent mechanical properties, low dielectric constant and low thermal expansion coefficient. The dielectric polymers are prepared from polymerizable compounds having mesogenic groups, which can be used as dielectric materials for the preparation of passivation layers in electronic devices.

[0017] Although these materials have many beneficial properties, some features, such as glass transition temperature and processability, need to be further increased or improved in order to realize the full potential of these materials. Object of the invention The object of the present invention is to overcome the shortcomings and disadvantages in the prior art and to provide a new class of dielectric polymer materials that exhibit an advantageous balanced profile of favorable material properties, especially with regard to the requirements in advanced electronic packaging applications, such as wafer level packaging (WLP), and for low dielectric adhesive applications.

[0018] It is therefore an object of the present invention to provide a dielectric polymer material that exhibits an advantageous balanced profile of material properties, including: (a) favorable thermomechanical properties, such as high thermal stability, high glass transition temperature (Tg), low coefficient of thermal expansion (CTE), high elongation at break and high tensile strength; (b) favorable dielectric properties, such as low dielectric constant and low dielectric loss tangent; (c) good adhesive properties, especially to copper and SiO2 passivated wafers; (d) low water absorption; and (e) good processability from solvents commonly used in the semiconductor industry.

[0019] A further object of the present invention is to provide bismaleimide compounds from which said dielectric polymer materials can be obtained. It is an object of the present invention that such bismaleimide compounds are photostructurable and can be used as starting materials for the preparation of repassivation layers for various applications in electronic device manufacturing, for example in packaged electronic devices (including passivation of conductive or semiconducting components in redistribution layers (RDL) or die attach), in thin film formulations and / or in adhesive formulations. In addition, said bismaleimide compounds should have good film-forming ability and be easy to process from solvents commonly used in the semiconductor industry to form dielectric polymers as spin-on materials.

[0020] Another object of the present invention is to provide a method for forming said dielectric polymer material using a bismaleimide compound.Finally, it is an object of the present invention to provide a dielectric polymer material and an electronic device comprising said polymer as a dielectric material.

[0021] It is an object of the present invention that bismaleimide compounds and related dielectric polymer materials enable cost-effective and reliable manufacturing of microelectronic devices with a significant reduction in the number of defective devices due to mechanical deformation (deflection) due to undesirable thermo-mechanical properties. Summary of the Invention

[0022] The present inventors have surprisingly found that the above objectives are achieved by dielectric polymer materials formed from a new class of bismaleimide compounds, which exhibit an advantageous balanced profile of material properties, including (a) favorable thermomechanical properties, such as high thermal stability, high glass transition temperature (Tg), low coefficient of thermal expansion (CTE), high elongation at break and high tensile strength; (b) favorable dielectric properties, such as low dielectric constant and low dielectric loss tangent; (c) good adhesive properties, especially to copper and SiO2 passivated wafers; (d) low water absorption; and (e) good processability from solvents commonly used in the semiconductor industry.

[0023] The bismaleimide compound of the present invention is represented by the formulas (1) to (4):

[0024] [ka]

[0025] [In the formula, A, in each occurrence independently of each other, is a linking unit that includes one or more of a divalent benzoxazole, a divalent benzothiazole, or a divalent benzimidazole moiety; B, in each occurrence independently, is a linking unit that includes one or more of an aliphatic, aromatic, or siloxane moiety, where B optionally contains a cardo or spiro center; R a and R b are, independently, and in each occurrence independently of each other, a linking unit that includes one or more of an aliphatic, aromatic, or siloxane moiety; R c is R a or R b and; X, in each occurrence, independently, is a functional group selected from the list consisting of an amide group, an ether group, an ester group, and a urethane group; R 1is H or alkyl having 1 to 5 carbon atoms, preferably H or CH3; R 2 is H or alkyl having 1 to 5 carbon atoms, preferably H or CH3; t is an integer of 1 to 12, preferably an integer of 1 to 8, more preferably an integer of 1 to 6; u is 0 or 1, preferably 0; n is an integer of 1 to 60, preferably an integer of 1 to 50, more preferably an integer of 2 to 30, and most preferably an integer of 3 to 20; m is an integer of 1 to 60, preferably an integer of 1 to 50, more preferably an integer of 2 to 30, and most preferably an integer of 3 to 20. is represented by one of

[0026] Said bismaleimide compounds are used as monomeric compounds to form a new class of dielectric polymer materials, which are prepared by the following method, which also forms part of the present invention.

[0027] 1. A method for forming a dielectric polymer material comprising the steps of: (i) providing a formulation comprising one or more bismaleimide compounds according to the present invention; (ii) curing the formulation; A method comprising:

[0028] Moreover, there is provided a dielectric polymer material obtainable or obtained by the above mentioned method for forming a dielectric polymer material.

[0029] Additionally, there is provided a dielectric polymer material comprising at least one repeat unit derived from a bismaleimide compound according to the present invention.

[0030] Finally, there is provided an electronic device comprising a dielectric polymer material according to the present invention.

[0031] Preferred aspects of the invention are set out hereinafter and in the dependent claims. [Brief description of the drawings]

[0032] [Figure 1] Schematic diagram of fan-out wafer-level packaging (WLP) structure. [Diagram 2] DMA of the polymeric material obtained in Example 1. [Diagram 3] DMA of the polymeric material obtained in Example 2. [Figure 4] DMA of the polymeric material obtained in Example 3. Detailed Description

[0033] definition The term "linking unit" as used herein refers to an organic structural unit that connects two or more parts of a molecule. A linking unit is typically composed of different moieties. A linking unit may be divalent or multivalent, preferably divalent.

[0034] The term "benzoxazole moiety," as used herein, refers to a structural unit of a chemical compound that contains at least one benzoxazole ring system. The benzoxazole moiety is preferably a -C(O)R v , -C(O)OR v , -NR v R w , -OR v , -R x , -CN, -F and -Cl, or may be unsubstituted or substituted with one or more substituents selected from the list consisting of: v =H, C6-C14 aryl or C1-C14 alkyl, R w =H, C6-C14 aryl or C1-C14 alkyl and R x = C6-C14 aryl or C1-C14 alkyl, preferably R v =H, methyl, ethyl, propyl or phenyl, R w =H, methyl, ethyl, propyl or phenyl and R x= methyl, ethyl, propyl or phenyl. The benzoxazole moiety is typically linked to at least two adjacent further structural units of a chemical compound.

[0035] The term "benzothiazole moiety," as used herein, refers to a structural unit of a chemical compound that contains at least one benzothiazole ring system. The benzothiazole moiety is preferably a -C(O)R v , -C(O)OR v , -NR v R w , -OR v , -R x , -CN, -F and -Cl, or may be unsubstituted or substituted with one or more substituents selected from the list consisting of: v =H, C6-C14 aryl or C1-C14 alkyl, R w =H, C6-C14 aryl or C1-C14 alkyl and R x = C6-C14 aryl or C1-C14 alkyl, preferably R v =H, methyl, ethyl, propyl or phenyl, R w =H, methyl, ethyl, propyl or phenyl and R x = methyl, ethyl, propyl or phenyl. The benzothiazole moiety is typically linked to at least two adjacent further structural units of a chemical compound.

[0036] The term "benzimidazole moiety," as used herein, refers to a structural unit of a chemical compound that contains at least one benzimidazole ring system. The benzimidazole moiety is preferably a -C(O)R v , -C(O)OR v , -NR v R w , -OR v , -R x , -CN, -F and -Cl, or may be unsubstituted or substituted with one or more substituents selected from the list consisting of: v =H, C6-C14 aryl or C1-C14 alkyl, R w=H, C6-C14 aryl or C1-C14 alkyl and R x = C6-C14 aryl or C1-C14 alkyl, preferably R v =H, methyl, ethyl, propyl or phenyl, R w =H, methyl, ethyl, propyl or phenyl and R x = methyl, ethyl, propyl or phenyl. The benzimidazole moiety is typically linked to at least two adjacent further structural units of the chemical compound.

[0037] The term "aliphatic moiety," as used herein, refers to a linear, branched, cyclic or bridged cyclic aliphatic unit that forms part of the structure of a chemical compound. The aliphatic moiety may contain one or more heteroatoms selected from N, O, S and P. The aliphatic moiety may be unsubstituted or may be preferably -C(O)R v , -C(O)OR v , -NR v R w , -OR v , -R x , -CN, -F and -Cl, where R v =H, C6-C14 aryl or C1-C14 alkyl, R w =H, C6-C14 aryl or C1-C14 alkyl and R x = C6-C14 aryl or C1-C14 alkyl, preferably R v =H, methyl, ethyl, propyl or phenyl, R w =H, methyl, ethyl, propyl or phenyl and R x = methyl, ethyl, propyl or phenyl. The aliphatic moiety may contain one or more functional groups, preferably selected from the list consisting of C=C double bond, C≡C triple bond, amide, carbamate, carbonate, ester, ether, secondary or tertiary amine and keto. The aliphatic moiety is typically linked to at least two adjacent further structural units of the chemical compound.

[0038] The term "aromatic moiety", as used herein, relates to a monocyclic or polycyclic aromatic unit that forms part of the structure of a chemical compound. A polycyclic aromatic unit contains two or more connected aromatic ring systems that are fixed in one plane. The aromatic moiety may be (i) a hydrocarbon aromatic moiety or (ii) a heteroatom-containing aromatic moiety, also referred to as a heteroaromatic moiety. A hydrocarbon aromatic moiety contains an aromatic ring structure made of carbon atoms, whereas a heteroaromatic moiety contains an aromatic ring structure that further comprises one or more heteroatoms selected from N, O, S and P. The aromatic moiety may be unsubstituted or preferably has a -C(O)R v , -C(O)OR v , -NR v R w , -OR v , -R x , -CN, -F and -Cl, where R v =H, C6-C14 aryl or C1-C14 alkyl, R w =H, C6-C14 aryl or C1-C14 alkyl and R x = C6-C14 aryl or C1-C14 alkyl, preferably R v =H, methyl, ethyl, propyl or phenyl, R w =H, methyl, ethyl, propyl or phenyl and R x = methyl, ethyl, propyl or phenyl. The aromatic moiety is typically linked to at least two adjacent further structural units of the chemical compound.

[0039] The term "siloxane moiety," as used herein, refers to a structural unit of a chemical compound that contains at least one Si-O-Si linkage. The siloxane moiety may be linear, branched, or cyclic. The siloxane moiety may be unsubstituted or preferably has a -C(O)R v , -C(O)OR v , -NR v R w , -OR v , -R x, -CN, -F and -Cl, where R v =H, C6-C14 aryl or C1-C14 alkyl, R w =H, C6-C14 aryl or C1-C14 alkyl and R x = C6-C14 aryl or C1-C14 alkyl, preferably R v =H, methyl, ethyl, propyl or phenyl, R w =H, methyl, ethyl, propyl or phenyl and R x = methyl, ethyl, propyl or phenyl. The siloxane moiety is typically linked to at least two adjacent further structural units of the chemical compound.

[0040] The term "spiro compound" as used herein describes a compound having a spiro center consisting of two rings connected orthogonally via one common quaternary bond atom. Typically, a carbon atom serves as the spiro center. The simplest spiro compounds are bicyclic or have a bicyclic moiety as part of a larger ring system, in either case the two rings connected via a common quaternary bond atom define the spiro center. The spiro center, together with the adjacent groups attached to it, forms the so-called "spiro moiety", which may be considered as the characteristic structural unit of a spiro compound. The spiro moiety is typically linked to at least two adjacent further structural units of a chemical compound. Polymeric spiro compounds are also referred to as "spiropolymers".

[0041] The term "cardo polymers", as used herein, describes a subgroup of polymers in which the carbons in the backbone of the polymer chain are also incorporated into ring structures. These backbone carbons are quaternary centers (cardo centers) and form part of the so-called "cardo moieties". Thus, the cyclic side groups are placed perpendicular to the plane of the polymer chain, creating a loop structure. Cardo structures are very similar to spiro structures, but have only one ring attached to the cardo center, while two rings are attached to the spiro center. The cardo center, together with the adjacent groups attached to it, forms the so-called "cardo moiety", which may be considered as the characteristic structural unit of a cardo polymer. The cardo moiety is typically linked to at least two adjacent further structural units of a chemical compound.

[0042] 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 specifically limited, the term "polymer" is intended to include all possible configurational isomers of a material. These configurations include, but are not limited to, isotactic, syndiotactic and atactic symmetries. Polymers are molecules of high relative molecular mass whose structure essentially comprises multiple repeats of units (i.e., repeat units) that are actually or conceptually derived from molecules of lower relative mass (i.e., monomers). Polymers are typically mixtures of molecules with different chain lengths and therefore have a molar mass distribution.

[0043] The term "oligomer" refers, in contrast to polymers, to molecular complexes consisting of a small number of monomer units, where the number of monomers is, in principle, unlimited. Dimers, trimers and tetramers are, for example, oligomers composed of two, three and four monomers, respectively. Oligomers are typically mixtures of molecules with different chain lengths and therefore have a molar mass distribution.

[0044] The term "monomer," as used herein, refers to a molecule that can undergo polymerization, thereby providing a building block (repeating unit) for the basic structure of a polymer or oligomer.

[0045] The term "homopolymer," as used herein, refers to a polymer derived from one species of monomer (actual, implied or hypothetical).

[0046] The term "copolymer" as used herein generally refers to any polymer derived from more than one type of monomer, where the polymer contains more than one type of corresponding repeat unit. In one embodiment, a copolymer is a reaction product of two or more types of monomers, and thus includes two or more types of corresponding repeat units. Preferably, the copolymer includes two, three, four, five, or six types of repeat units. A copolymer obtained by copolymerization of three monomer types can also be referred to as a terpolymer. A copolymer obtained by copolymerization of four monomer types can also be referred to as a quaterpolymer. The copolymer may exist as a block, random, and / or alternating copolymer.

[0047] 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 monomer but with different composition or sequence distribution of the repeat units.

[0048] 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 the adjacent repeat units. Typically, in random copolymers, the sequence distribution of the repeat units follows Bernoulli statistics.

[0049] The term "alternating copolymer," as used herein, refers to a copolymer consisting of a macromolecule that contains two types of repeat units in alternating sequences.

[0050] "Electronic packaging" is a major area within the electronics field and includes a wide variety of technologies. It refers to the insertion of discrete components, integrated circuits, and MSI (medium-scale integration) and LSI (large-scale integration) chips (usually attached to a lead frame by beam leads) through holes on a multilayer circuit board (also called a card) into a plate where they are soldered into place. Packaging of electronic systems must take into account protection from mechanical damage, cooling, radio frequency noise emissions, protection from sustained electrostatic discharge, operator convenience, and cost.

[0051] The term "microelectronic device" as used herein refers to electronic devices of very small electronic design and components. Usually, but not necessarily, this means micrometer scale or smaller. These devices typically contain one or more microelectronic components made from semiconductor materials and interconnected with packaged structures to form the microelectronic device. Many electronic components of common electronic designs are available in microelectronic equivalents. These include transistors, capacitors, inductors, resistors, diodes, and necessarily insulators and conductors, all of which can be found in microelectronic devices. Unique wiring techniques, such as wire bonding, are also frequently used in microelectronics due to the unusually small size of the components, leads, and pads. Preferred Aspects Bismaleimide Compounds The present invention relates to a compound represented by the formulas (1) to (4):

[0052] [ka]

[0053] [In the formula, A, in each occurrence independently of each other, is a linking unit that includes one or more of a divalent benzoxazole, a divalent benzothiazole, or a divalent benzimidazole moiety; B, in each occurrence independently, is a linking unit that includes one or more of an aliphatic, aromatic, or siloxane moiety, where B optionally contains a cardo or spiro center; R a and R b are, independently, and in each occurrence independently of each other, a linking unit that includes one or more of an aliphatic, aromatic, or siloxane moiety; R c is R a or R b and; X, in each occurrence, independently, is a functional group selected from the list consisting of an amide group, an ether group, an ester group, and a urethane group; R 1 is H or alkyl having 1 to 5 carbon atoms, preferably H or CH3; R 2 is H or alkyl having 1 to 5 carbon atoms, preferably H or CH3; t is an integer of 1 to 12, preferably an integer of 1 to 8, more preferably an integer of 1 to 6; u is 0 or 1, preferably 0; n is an integer of 1 to 60, preferably an integer of 1 to 50, more preferably an integer of 2 to 30, and most preferably an integer of 3 to 20; m is an integer of 1 to 60, preferably an integer of 1 to 50, more preferably an integer of 2 to 30, and most preferably an integer of 3 to 20. The present invention relates to a bismaleimide compound represented by one of the following:

[0054] Bismaleimide compounds according to formula (3) or (4) contain two different repeat units, which are represented by the repeat units marked by the subscripts m and n, respectively. Thus, the compounds may be considered as cooligomers, where the different repeat units may form blocks (block cooligomers), alternate (alternating cooligomers), or be randomly distributed throughout the cooligomer (random cooligomers).

[0055] In formulas (1), (2), (3) and / or (4), it is preferred that A further comprises a phenylene moiety.

[0056] In a preferred embodiment of the present invention, A is, independently of each other in each occurrence, a group of the formulae (5a) to (5c):

[0057] [ka]

[0058] [In the formula,

[0059] [ka]

[0060] represents the binding site; Q is O, NH or S, preferably O; D are, independently of each other in each occurrence, a divalent aromatic group preferably having 4 to 20 carbon atoms, a divalent aliphatic group preferably having 2 to 20 carbon atoms, or a divalent mixed aromatic aliphatic group preferably having 6 to 30 carbon atoms, which may contain one or more heteroatoms selected from N, O and S, which may be substituted with one or more substituents selected from the list consisting of halogen, alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 5 carbon atoms, phenyl and phenyloxy, preferably F, Cl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butyloxy, phenyl and phenyloxy; G is -O-, -S-, -CO-, -(CO)-O-, -O-(CO)-, -S-(CO)-, -(CO)-S-, -O-(CO)-O-, -(CO)-NR 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-(CO)-O-, -O-(CO)-CH=CH-, or a single bond, where R 01 and R 02 are each independently H or an alkyl group having 1 to 5 carbon atoms, preferably methyl, ethyl, propyl and butyl; Y 01 and Y 02 are each independently H, alkyl having 1 to 5 carbon atoms, preferably methyl, ethyl, propyl and butyl, phenyl, F, Cl or CN. is represented by one of

[0061] In formula (5a), (5b) and / or (5c), it is preferred that D is a phenylene moiety.

[0062] In formula (5a), (5b) and / or (5c), it is preferred that G is O or a single bond.

[0063] In a preferred embodiment of the invention, B is, independently from each other in each occurrence, a substituted or unsubstituted aliphatic moiety having 2 to 100 carbon atoms, preferably 2 to 80 carbon atoms, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 100 carbon atoms, preferably 6 to 80 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 100 carbon atoms, preferably 4 to 80 carbon atoms, a substituted or unsubstituted siloxane moiety having 2 to 50 silicon atoms, preferably a dimethylsiloxane, methylphenylsiloxane, diphenylsiloxane moiety, or a combination thereof, wherein B optionally contains a cardo or spiro center.

[0064] In a more preferred embodiment of the invention, B, independently of each other in each occurrence, is of formula (6a) or (6b):

[0065] [ka]

[0066] [In the formula,

[0067] [ka]

[0068] represents the binding site; x and y are each independently an integer of 0 to 10, preferably an integer of 1 to 8, more preferably an integer of 3 to 8, and most preferably an integer of 7 or 8; R I and R IIare each independently a linear alkyl group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, and more preferably 6 or 8 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms, a linear alkylene group having 2 to 10 carbon atoms, preferably 2 to 8 carbon atoms, or a branched alkylene group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms. is represented by one of

[0069] Preferably, R in formula (6a) I and R II are, independently of each other, -CH 13 , -CH 17 , -CH2CH(C2H5)C4H9 or -CH2-CH2-CH=CH-C3H7.

[0070] In a preferred embodiment of the present invention, R a and R b are, independently, and independently of each other in each occurrence, a substituted or unsubstituted aliphatic moiety having 2 to 100 carbon atoms, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 100 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 100 carbon atoms, a substituted or unsubstituted siloxane moiety having 2 to 50 silicon atoms, preferably a dimethylsiloxane, methylphenylsiloxane, diphenylsiloxane moiety, or combinations thereof; R c is R a or R b It is.

[0071] In a more preferred embodiment of the present invention, R a and R bare independently, and in each occurrence independently of each other, a substituted or unsubstituted aliphatic moiety having 2 to 100 carbon atoms, preferably 2 to 60 carbon atoms, more preferably 10 to 50 carbon atoms, and most preferably 10 to 36 carbon atoms, optionally containing one or more of a C=C double bond, a C≡C triple bond or an amide group, preferably -NH-(CO)- or -(CO)-NH-; R c is R a or R b It is.

[0072] Preferably, in formula (1), (2), (3) and / or (4), R a and R b independently and independently of each other in each occurrence, the formulas (8a) to (8d):

[0073] [ka]

[0074] [In the formula,

[0075] [ka]

[0076] represents the binding site; x and y are each independently an integer of 0 to 10, preferably an integer of 1 to 8, more preferably an integer of 3 to 8, and most preferably an integer of 7 or 8; R I and R II are each independently a linear alkyl group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, and more preferably 6 or 8 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms, a linear alkylene group having 2 to 10 carbon atoms, preferably 2 to 8 carbon atoms, or a branched alkylene group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms. is represented by one of

[0077] Preferably, R in formula (8a) I and R II are, independently of each other, -CH 13 , -CH 17 , -CH2CH(C2H5)C4H9 or -CH2-CH2-CH=CH-C3H7.

[0078] More preferably, in formula (1), (2), (3) and / or (4), R a and R b independently, and independently of each other in each occurrence, the formulas (9a) to (9e):

[0079] [ka]

[0080] [In the formula,

[0081] [ka]

[0082] represents the binding site] is represented by one of

[0083] Preferably, in formula (1), (2), (3) and / or (4), X is, independently of each other in each occurrence, -(CO)-NR 3 -, -NR 3 -(CO)-, -O-, -(CO)-O-, -O-(CO)-, -O-(CO)-NR 3 -OR-NR 3 -(CO)-O-, where R 3 is H or alkyl having 1 to 5 carbon atoms, preferably H or CH3, more preferably H.

[0084] More preferably, in formula (1), (2), (3) and / or (4), X is, independently of each other in each occurrence, -(CO)-NR 3 -OR-NR 3 -(CO)-, where R 3 is H or alkyl having 1 to 5 carbon atoms, preferably H or CH3, more preferably H.

[0085] Particularly preferred bismaleimide compounds according to formula (1), (2), (3) and / or (4) are BM1 to BM8:

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] It is.

[0091] The bismaleimide compounds of the present invention can be prepared by any standard synthesis. Usually, the compounds are retrosynthetically cleaved into smaller units, which are formed stepwise from suitable precursor compounds. For this purpose, known standard reactions can be used. It has proven particularly advantageous to attach the maleimide group at a late stage of the synthesis, typically in the very last step of the synthesis. By doing so, undesired side reactions or premature polymerization of the compounds can be avoided.

[0092] The maleimide group is a functional group capable of undergoing polymerization reactions, such as radical or ionic chain polymerization, polyaddition or polycondensation, or polymerization-like reactions, such as addition or condensation on a polymer backbone.

[0093] The present invention further provides a method for forming a dielectric polymer material comprising repeat units derived from one or more of the bismaleimide compounds according to the present invention. The dielectric polymer material may be linear or cross-linked.

[0094] A method for forming a dielectric polymer material according to the present invention comprises the steps of: (i) providing a formulation comprising one or more bismaleimide compounds according to the present invention; (ii) curing the formulation; Includes.

[0095] Preferably, the formulation provided in step (i) further comprises one or more additional compounds capable of reacting with the bismaleimide compound according to the invention to preferably form a copolymer. Using basic chemical knowledge, the skilled person can find and select, for a given bismaleimide compound of the invention, suitable additional compounds capable of reacting with the first mentioned to preferably form a copolymer.

[0096] Preferred additional compounds that can react with the bismaleimide compounds according to the invention are selected from the list consisting of acrylates, epoxides, olefins, vinyl ethers, vinyl esters, polythiols, polyamines and polymaleimides.

[0097] Preferred acrylates are acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, methyl cyanoacrylate, ethyl acrylate, ethyl methacrylate, ethyl cyanoacrylate, propyl acrylate, propyl methacrylate, propyl cyanoacrylate, butyl acrylate, butyl methacrylate, butyl cyanoacrylate, pentyl acrylate, pentyl methacrylate, pentyl cyanoacrylate, hexyl acrylate, hexyl methacrylate, hexyl cyanoacrylate, heptyl acrylate, heptyl methacrylate, heptyl cyanoacrylate, octyl acrylate, octyl methacrylate, octyl cyanoacrylate, ethylene glycol dimethacrylate, 2-ethylhexyl acrylate, glycidyl methacrylate, (hydroxyethyl)acrylate, (hydroxyethyl)methacrylate, methyl 2-chloroacrylate, and methyl 2-fluoroacrylate.

[0098] Preferred epoxides are ethylene oxide, propylene oxide, butylene oxide, pentylene oxide, hexylene oxide, heptylene oxide, octylene oxide, glycidamide, glycidol, styrene oxide, 3,4-epoxytetrahydrothiophene-1,1-dioxide, ethyl 2,3-epoxypropionate, methyl 2-methylglycidate, methyl glycidyl ether, ethyl glycidyl ether, diglycidyl ether, cyclopentene oxide, cyclohexene oxide, cycloheptene oxide, cyclooctene oxide, and stilbene oxide.

[0099] Preferred olefins are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, isoprene styrene, and vinyl ethylene.

[0100] Preferred vinyl ethers are divinyl ether, methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, pentyl vinyl ether, hexyl vinyl ether, heptyl vinyl ether, and octyl vinyl ether.

[0101] Preferred vinyl esters are vinyl formate, vinyl acetate, vinyl propionate, vinyl butanoate, vinyl pentanoate, vinyl hexanoate, vinyl heptanoate, vinyl octanoate, vinyl nonanoate, vinyl decanoate, vinyl acrylate, vinyl methacrylate, vinyl benzoate, vinyl 4-tert-butylbenzoate, vinyl cinnamate, and vinyl trifluoroacetate.

[0102] Preferred polythiols are organosulfur compounds having two or more thiol functional groups. Particularly preferred polythiols are HS-(C n H 2n )-SH (wherein n=2 to 20, preferably 2 to 12); C n H 2n-1 (SH)3 (wherein n=3 to 20, preferably 3 to 12); HS-Ar-SH (wherein Ar=substituted or unsubstituted C6 to C 20 arylene); and HS-(CH2) m -Ar-(CH2) m -SH (where Ar=substituted or unsubstituted C6-C 20 arylene, m=1-12).

[0103] Preferred polyamines are organic amine compounds having two or more amino functional groups. Particularly preferred polyamines are H2N-(C n H 2n )-NH2 (wherein n=2 to 20, preferably 2 to 12); H2N-(C n H 2n NH)-NH2 (wherein n=2 to 20, preferably 2 to 12); C n H 2n-1 (NH2)3 (wherein n=3 to 20, preferably 3 to 12); H2N-Ar-NH2 (wherein Ar=substituted or unsubstituted C6 to C20 arylene); and H2N-(CH2) m -Ar-(CH2) m -H2N (where Ar = substituted or unsubstituted C6-C 20 arylene, m=1-12).

[0104] Preferred polymaleimides are maleimide end-capped polyimides as described in US2004 / 0225026A1 and US2017 / 0152418A1, the disclosures of which are incorporated herein by reference. The polymaleimides have the following formula (A) or formula (B):

[0105] [ka]

[0106] [wherein R1 and Q1 are independently selected from the list consisting of unsubstituted or substituted aliphatic, alicyclic, alkenyl, aryl, heteroaryl, siloxane, poly(butadiene-co-acrylonitrile) and poly(alkylene oxide) derived structures; X1-X4 are each independently H or an alkyl group having 1-6 C atoms; n=0-30];

[0107] [ka]

[0108] [wherein R2 and Q2 are independently selected from the list consisting of unsubstituted or substituted aliphatic, alicyclic, alkenyl, aryl, heteroaryl, siloxane, poly(butadiene-co-acrylonitrile) and poly(alkylene oxide) derived structures; X5-X8 are each independently H or an alkyl group having 1-6 C atoms; R3 and R4 are each independently H or CH3 (wherein at least one of R3 and R4 is CH3), and n=0-30] Preferably, the bismaleimide is selected from the compounds represented by

[0109] In preferred embodiments of formulas (A) and (B), the unsubstituted or substituted aliphatic, alicyclic, alkenyl, aryl, heteroaryl, siloxane, poly(butadiene-co-acrylonitrile) and poly(alkylene oxide) derived structures are selected from the group consisting of alkyl, alkenyl, alkynyl, hydroxyl, oxo, alkoxy, mercapto, cycloalkyl, substituted cycloalkyl, heterocyclic, substituted heterocyclic, aryl, substituted aryl, heteroaryl, substituted heteroaryl, ... It is preferable that one end of the alkyl group further contains a substituent, and the alkyl group is an oxy group, a substituted aryloxy group, a halogen atom, a haloalkyl group, a cyano group, a nitro group, a nitrone group, an amino group, an amido group, -C(O)H, an acyl group, an oxyacyl group, a carboxyl group, a carbamate group, a sulfonyl group, a sulfonamide group, a sulfuryl group, or -C(O)-, -S-, -S(O)2-, -OC(O)-O-, -NA-C(O)-, -NAC(O)-NA-, -OC(O)-NA- (wherein A is H or an alkyl group having 1 to 6 carbon atoms).

[0110] Preferred substituents are an alkyl group, an alkenyl group, an alkynyl group, a hydroxyl group, an oxo group, an alkoxy group, a mercapto group, a cycloalkyl group, a substituted cycloalkyl group, a heterocyclic group, a substituted heterocyclic group, an aryl group, a substituted aryl group, a heteroaryl group, a substituted heteroaryl group, an aryloxy group, a substituted aryloxy group, a halogen, a haloalkyl group, a cyano group, a nitro group, a nitrone group, an amino group, an amido group, -C(O)H, an acyl group, an oxidase group, an aryloxy group, a cycloalkyl ... A is a cyacyl group, a carboxyl group, a carbamate group, a sulfonyl group, a sulfonamide group, a sulfuryl group, or -C(O)-, -S-, -S(O)2-, -OC(O)-O-, -NA-C(O)-, -NAC(O)-NA-, -OC(O)-NA- (wherein A is H or an alkyl group having 1 to 6 carbons), an acyl group, an oxyacyl group, a carboxyl group, a carbamate group, a sulfonyl group, a sulfonamide group, or a sulfuryl group.

[0111] In more preferred embodiments of formulas (A) and (B), R 1 and R 2 , and Q 1 and Q 2 is independently selected from the list consisting of substituted or unsubstituted aliphatic, alicyclic, alkenyl, aromatic, siloxane, poly(butadiene-co-acrylonitrile), or poly(alkylene oxide) moieties.

[0112] Preferred aliphatic moieties are straight or branched C1-C 50 Alkylene, more preferably linear or branched C1-C 36 It is alkylene.

[0113] Preferred alicyclic moieties are both aliphatic and cyclic, and contain one or more all-carbon rings, which may be either substituted or unsubstituted, and may optionally be fused and / or bridged. Preferred alicyclic moieties have 3 to 72 C atoms, more preferably 3 to 36 C atoms. Particularly preferred alicyclic moieties are -Sp 1 -Cy-Sp 2 - where Sp 1 and Sp 2 denote, independently of one another, an alkylene having 1 to 12 C atoms or a single bond; G denotes a cycloalkylene having 3 to 12 C atoms, optionally mono- or polysubstituted by alkyl having 1 to 12 C atoms.

[0114] Preferred alkenyl moieties are linear or branched hydrocarbyl moieties having at least one carbon-carbon double bond and ranging up to about 100 C atoms. More preferred alkenyl moieties are C2-C 50 Alkenylene, most preferably C2-C 36 It is alkenylene.

[0115] Preferred aromatic moieties include (i) hydrocarbon aromatic moieties, such as arylene groups, which may be either substituted or unsubstituted, having 6 to 20 C atoms, more preferably 6 to 14 C atoms, and (ii) heteroaromatic moieties, which may be either substituted or unsubstituted, having 3 to 20 C atoms, preferably 3 to 14 C atoms, and one or more heteroatoms selected from N, O, S and P in the aromatic ring structure.

[0116] Preferred siloxane moieties are -[R a R b Si-O] n -R a R b Si-, where R a and R b are independently H or C1-C6 alkyl, and n=1-1000, more preferably 1-100.

[0117] Preferred poly(alkylene oxide) moieties are poly(C1-C 12 alkylene oxide) moiety.

[0118] Preferably, the molar ratio between the bismaleimide compound of the present invention and the additional compound capable of reacting with the bismaleimide compound in the formulation is from 0.1:100 to 100:0.1.

[0119] It is further preferred that the formulation provided in step (i) comprises one or more inorganic or organic fillers. Preferred inorganic fillers are selected from the list consisting of nitrides, titanates, diamond, oxides, sulfides, sulfites, sulfates, silicates and carbides, which may be surface modified with a capping agent. More preferably, the inorganic fillers are selected from the list consisting of AlN, Al2O3, BN, BaTiO3, B2O3, Fe2O3, SiO2, TiO2, ZrO2, PbS, SiC, diamond and glass particles, which may be surface modified with a capping agent. Preferred organic fillers are diamondoids or organic polymer particles. Preferred diamondoids are adamantane (C10 H 16 ), Iceane (C 12 H 18 ), BC-8(C 14 H 20 ), Diamantane (C 14 H 20 ), triamantane (C 18 H 24 ), isotetramantane (C 22 H 28 ), Pentamantane (C 26 H 32 and C 25 H 30 ), cyclohexamantane (C 26 H 30 ) and super adamantane (C 30 H 36 ).

[0120] Preferably, the total content of the filler material in the composition is in the range of 0.001 to 90% by weight, more preferably 0.01 to 70% by weight, and most preferably 0.01 to 50% by weight, based on the total weight of the composition.

[0121] In a preferred embodiment, the formulation is provided on a surface of a substrate in step (i) and, after curing in step (ii), forms a dielectric polymer material on said surface. The substrate is preferably a substrate of an electronic or microelectronic device.

[0122] Preferably, the formulation is provided in step (i) in a single coating, as a layer having an average thickness of 0.5 to 50 μm, more preferably 2 to 30 μm, most preferably 3 to 15 μm.

[0123] The method of applying the composition in step (i) is not particularly limited.Preferred application methods include dispensing, dipping, screen printing, stencil printing, roller coating, spray coating, slot coating, slit coating, spin coating, gravure printing, flexographic printing, or inkjet printing.

[0124] The bismaleimide compounds of the present invention may be provided in the form of formulations suitable for gravure, flexographic and / or inkjet printing. For the preparation of such formulations, ink base formulations as known from the prior art can be used.

[0125] Alternatively, the bismaleimide compounds of the present invention may be provided in the form of a formulation suitable for photolithography. Photolithography allows photopatterning by using light to transfer a geometric pattern from a photomask to a photocurable composition. Typically, such photocurable compositions contain a photochemically activatable polymerization initiator. For the preparation of such formulations, photoresist-based formulations as known from the state of the art can be used.

[0126] Without wishing to be bound by theory, curing of the bismaleimide compounds according to the present invention may occur via various types of reactions, such as radical polymerization, ionic polymerization, Michael addition and / or cycloaddition reactions.

[0127] The formulation is preferably cured in step (ii) by exposure to heat, preferably at a temperature in the range of 25-200° C., more preferably at a temperature in the range of 25-150° C., and / or by exposure to radiation. Preferred conditions for exposure to radiation are further described below.

[0128] It is further preferred that the formulation contains an initiator for free radical polymerization or an initiator for ionic polymerization.

[0129] Preferably, the initiators for radical polymerization are activated thermally by exposure to heat or photochemically by exposure to radiation, such as UV and / or visible light.

[0130] Preferred initiators for radical polymerization 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)-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-butyl peroxy isopropyl carbonate, cumene hydroperoxide, cyclohexanone peroxide, dicumyl peroxide, lauroyl peroxide, 2,4-pentanedione peroxide, peracetic acid, and potassium persulfate. Typically, such initiators are radical polymerization initiators that may be thermally activated.

[0131] Further preferred initiators for the radical polymerization 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, These 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)phosphinate, 2-methyl-4'-(methylthio)-2-morpholinopropiophenone, 2-isonitrosopropiophenone, 2-phenyl-2-(p-toluenesulfonyloxy)acetophenone, and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide. Typically such initiators are radical polymerization initiators which may be photochemically activated.

[0132] Preferred initiators for ionic polymerization are alkyllithium compounds, alkylaminelithium compounds, and pentamethylcyclopentadienyl (Cp*) complexes of titanium, zirconium, and hafnium.

[0133] Further preferred initiators for ionic polymerization are bis(4-tert-butylphenyl)iodonium hexafluorophosphate, bis(4-fluorophenyl)iodonium trifluoromethanesulfonate, cyclopropyldiphenylsulfonium tetrafluoroborate, dimethylphenacylsulfonium tetrafluoroborate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroarsenate, diphenyliodonium trifluoromethanesulfonate, 2-(3,4-diphenyliodonium hexafluorophosphate, bis(4-fluorophenyl) ... methoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(furan-2-yl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, 2-[2-(5-methylfuran-2-yl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(4 -Methoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine, (2-methylphenyl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate, (3-methylphenyl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate, (4-methylphenyl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate, 4-nitrobenzenediazonium tetrafluoroborate, (4-nitrophenyl)(phenyl)iodonium Examples of suitable initiators include trifluoromethanesulfonate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium bromide, tri-p-tolylsulfonium hexafluorophosphate, tri-p-tolylsulfonium trifluoromethanesulfonate, [3-(trifluoromethyl)phenyl](2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate, and [4-(trifluoromethyl)phenyl](2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate. Typically, such initiators are cationic polymerization initiators which may be photochemically activated.

[0134] Further preferred initiators for ionic polymerization are acetophenone O-benzoyloxime, 1,2-bis(4-methoxyphenyl)-2-oxoethylcyclohexylcarbamate, nifedipine, 2-nitrobenzylcyclohexylcarbamate, 2-(9-oxoxanthen-2-yl)propionic acid 1,5,7-triazabicyclo[4.4.0]dec-5-ene salt, 2-(9-oxoxanthen-2-yl)propionic acid 1,5-diazabicyclo[4.3.0]non-5-ene salt, and 2-(9-oxoxanthen-2-yl)propionic acid 1,8-diazabicyclo[5.4.0]undec-7-ene salt. Typically, such initiators are anionic polymerization initiators that may be photochemically activated.

[0135] The exposure to radiation includes exposure to visible light and / or UV light. Visible light is preferably electromagnetic radiation having a wavelength of more than 380 to 780 nm, more preferably more than 380 to 500 nm. UV light is preferably electromagnetic radiation having a wavelength of 380 nm or less, more preferably 100 to 380 nm. More preferably, UV light is selected from UV-A light having a wavelength of 315 to 380 nm, UV-B light having a wavelength of 280 to 315 nm, and UV-C light having a wavelength of 100 to 280 nm. The exposure to radiation preferably includes wavelengths according to g, h, i rays, and / or broadband.

[0136] The UV light source can be a Hg vapour lamp or a UV laser, the IR light source can be a ceramic emitter or an IR laser diode, and for light in the visible range a laser diode.

[0137] Preferred UV sources are sources having a) a single wavelength radiation with a maximum below 255 nm, such as Hg low pressure discharge lamps at 254 nm and 185 nm, ArF excimer lasers at 193 nm and Xe2 layers at 172 nm, or b) a broad wavelength distribution radiation with wavelength components below 255 nm, such as non-doped Hg low pressure discharge lamps.

[0138] In a preferred embodiment of the invention, the light source is a xenon flashlight. Preferably, the xenon flashlight has a broad emission spectrum with short wavelength components down to about 200 nm.

[0139] There is further provided a dielectric polymer material, obtainable or obtained by the above mentioned method for forming a dielectric polymer material according to the present invention. The polymer material is preferably a linear or cross-linked polymer, more preferably a linear polymer.

[0140] There is further provided a dielectric polymer material comprising at least one repeat unit derived from a bismaleimide compound of any one of formulas (1), (2), (3) or (4) as defined above.

[0141] In a preferred embodiment, the dielectric polymer material comprises at least one repeat unit having the formula (10)-(13):

[0142] [ka]

[0143] [In the formula, A, B, R a , R b , X, n and m have one of the definitions mentioned above for formulae (1), (2), (3) and (4) or the related preferred, more preferred, particularly preferred or most preferred embodiments. It includes a structural unit represented by one of:

[0144] In a preferred embodiment, the dielectric polymer material further contains additional repeat units derived from additional compounds capable of reacting with the bismaleimide compounds as defined above.

[0145] Moreover, there is provided an electronic device comprising a dielectric polymer material according to the invention, in which the polymer material preferably forms a dielectric layer, which serves to electrically isolate one or more electronic components that are part of the electronic device from one another.

[0146] Preferably, the electronic device is a microelectronic device and the dielectric polymer material is included as a repassivation material in a redistribution layer of the microelectronic device.

[0147] 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 substitutions may be made to the present invention without departing from the spirit and scope of the invention as defined in the appended claims.

[0148] [example] Synthesis of A building block A-1 Synthesis of 4,4'-((1r,3r)-adamantane-2,2-diyl)diphenol (1)

[0149] [ka]

[0150] 2-Adamantanone (CAS: 700-58-3, Sigma Aldrich, 40 mmol, 6.0 g) was added to a mixture of 25 mL toluene and molten phenol (100 mmol, 9.4 g) at 50° C. under nitrogen atmosphere and stirred until it became homogeneous. 3-Mercaptopropionic acid (3.4 mmol, 0.3 mL), methanesulfonic acid (3 mL) and trifluoromethanesulfonic acid (0.3 mL) were added dropwise and the reaction mixture was kept at 50° C. for 12 hours during which a white solid precipitated. The solid was filtered, washed with hot water and recrystallized from ethanol to give colorless needles. 47% yield.

[0151] analysis: 1 H NMR (500 MHz, DMSO-d6): δ = 9.02 (s, 2H), 7.20 - 7.15 (m, 4H), 6.60 (d, J = 7.6 Hz, 4H), 3.17 (s, 2H), 1.91 (d, J = 12.3 Hz, 4H), 1.74 (s, 2H), 1.68 - 1.62 (m, 6H) ppm. A-2 Synthesis of 7,7'-((((1r,3r)-adamantane-2,2-diyl)bis(4,1-phenylene))-bis(oxy))bis(heptan-1-amine) hydrochloride (2)

[0152] [ka]

[0153] tert-Butyl (7-hydroxyheptyl)carbamate (Merck, CAS: 173436-02-7, 31 mmol, 7.2 g) was dissolved in THF (30 mL) together with compound (1) (31 mmol, 9.9 g) at 0° C. Then, a solution of DEAD (40 wt% solution in toluene; 21.1 mL, 46.5 mmol) and triphenylphosphine (12.2 g, 46.5 mmol) in THF (50 mL) was added at 0° C. The reaction mixture was stirred at room temperature. After 24 h, the solvent was evaporated and the crude product was purified by column chromatography on silica gel (AcOEt / hexane=1:8). The boc-protected intermediate was dissolved in 100 mL of 4N HCl in dioxane and stirred at room temperature for 2 h. The solvent was evaporated and the crude product was recrystallized in ethanol to give 16.8 g (88%) as a colorless solid.

[0154] analysis: 1 H NMR (500 MHz, DMSO-d6): δ = 7.99 (wide s), 7.30 (d, J = 7.6 Hz, 4H), 6.75 (d, J = 7.6 Hz, 4H), 3.86 - 3.83 (m, 4H), 3.22 (s, 2H), 2.73 (m, 4H), 1.90 - 1.87 (m, 4H), 1.73 (s, 2H), 1.68 - 1.65 (m, 12H), 1.55 - 1.52 (m, 4H), 1.36 - 1.29 (m, 12H) ppm. A-3 Synthesis of Pripol acid chloride (3)

[0155] [ka]

[0156] Pripol™ 1009 (Croda, 20 mmol, 11.3 g) was dissolved in 40 mL of dry toluene and a catalytic amount of DMF. Thionyl chloride (Merck, 40 mmol, 4.8 g) was added at 0° C. and the reaction mixture was heated at 80° C. for 4 h. After cooling to room temperature, the solvent was evaporated and the crude product was dissolved in toluene and evaporated again to azeotropically remove any unreacted thionyl chloride. The crude product (3) (20 mmol, 12 g, 100% yield) was dried and used without further purification.

[0157] Synthesis of B oligomer B-1 Synthesis of BM2

[0158] [ka]

[0159] Pripol acid chloride (3) (20 mmol, 12 g) was dissolved in 50 mL of dry DMAc and triethylamine (60 mmol, 6 g). Diaminobenzoxazole (4) (Biosynth Carbosynth Limited, CAS: 16363-53-4, 40 mmol, 9 g) was added at 0 °C and the reaction mixture was stirred at room temperature for 6 h. After precipitation in acetonitrile, the intermediate oligomer was obtained. The amino-terminated molecule was then dissolved in p-xylene (150 mL). Triethylamine (140 mmol, 14 g), methanesulfonic acid (144 mmol, 14) and maleic anhydride (40 mmol, 4 g) were then carefully added. Using a Dean-Stark apparatus, the reaction mixture was heated to reflux (12 h). After cooling to room temperature, 9.5 g (41%) of benzoxazole-extended bismaleimide (BM2) was obtained after precipitation in acetonitrile.

[0160] Analysis: GPC: M n : 5.6 kDa, M w : 10.1 kDa, PDI: 1.8. 11H NMR (500 MHz, THF-d8): δ = 9.27 (s), 9.22 (s), 8.41 (s), 8.35 (s), 8.27 (d, J = 8.3 Hz), 8.10 (d, J = 8.4 Hz), 7.80 (d, J = 8.3 Hz), 7.62 (d, J = 8.5 Hz), 7.57 (d, J = 8.4 Hz), 7.51 (d, J = 8.5 Hz), 7.28 (d, J = 8.5 Hz), 7.26 (d, J = 8.5 Hz), 6.98 (s), 6.91 (s), 3.64 - 3.59 (m), 2.86 (s), 2.77 (s), 2.53 (s), 2.33 (td, J = 9.0, 8.3, 4.6 Hz), 1.86 (s), 1.77 (h, J = 3.2, 2.6 Hz), 1.70 (d, J = 8.4 Hz), 1.58 (s), 1.57 - 1.53 (m), 1.37 (s), 1.36 (s), 1.32 - 1.24 (m), 1.12 (d, J = 7.0 Hz), 0.91 - 0.86 (m), 0.87 - 0.83 (m) ppm. Synthesis of B-2 BM4

[0161] [Chemical formula]

[0162] Pripol™ (Croda, 13.8 g, 25 mmol) was dissolved in NMP (80 mL) together with 2-(4-aminophenyl)-1,3-benzoxazol-6-amine (4) (Biosynth AG, 2.25 g, 10 mmol), CaCl2 (3.6 g, 32 mmol), pyridine (8.7 g, 110 mmol) and triphenyl phosphite (10.9 g, 35 mmol). The reaction mixture was stirred at 120° C. for 2 h, cooled to room temperature, treated with 1-(6-aminohexyl)-2,5-dihydro-1H-pyrrole, 2,5-dione trifluoroacetate (CAS: 222159-87-7, 4.7 g, 15 mmol) and stirred again at 120° C. for 2 h. After cooling to room temperature, 400 mL of acetonitrile was added to precipitate the crude polymer. The solid was washed several times with ethanol, warm water and again with ethanol, and dried under vacuum to give 14 g of a brown waxy solid (BM4).

[0163] Analysis: GPC: M n : 3.9 kDa, M w : 7.6 kDa, PDI: 2.0. 1 H NMR (500 MHz, THF-d8) δ = 9.38 - 9.27 (m), 8.36 (s), 8.10 (d, J = 8.5 Hz), 7.81 (d, J = 8.5 Hz), 7.51 (d, J = 8.4 Hz), 7.37 - 7.11 (m), 7.05 (d, J = 8.0 Hz), 6.93 (s), 3.29 (t, J = 7.0 Hz), 3.22 (s), 3.14 (q, J = 6.9 Hz), 2.53 (q, J = 7.4 Hz), 2.33 (t, J = 7.8 Hz), 2.20 (t, J = 7.7 Hz), 2.15 - 2.06 (m), 1.92 (p, J = 7.5 Hz), 1.69 (t, J = 7.1 Hz), 1.57 (s), 1.52 (s), 1.44 (s), 1.40 (s), 1.35 (s), 1.29 (s), 0.88 (q, J = 9.7, 8.1 Hz) ppm. B-3 Synthesis of BM5

[0164] [ka]

[0165] Pripol acid chloride (3) (20 mmol, 12 g) was dissolved in 50 mL of dry DMAc and triethylamine (60 mmol, 6 g). Diaminobenzoxazole (4) (Biosynth Carbosynth Limited, CAS: 16363-53-4, 20 mmol, 4.5 g) and diamine (2) (20 mmol, 10.9 g) were added at 0 °C and the reaction mixture was stirred at room temperature for 6 h. After precipitation in acetonitrile, the intermediate oligomer was obtained. The amino-terminated molecule was then dissolved in p-xylene (150 mL). Triethylamine (140 mmol, 14 g), methanesulfonic acid (144 mmol, 14) and maleic anhydride (40 mmol, 4 g) were then carefully added. The reaction mixture was heated to reflux (12 h) using a Dean-Stark apparatus. After cooling to room temperature, 9.4 g (63%) of the benzoxazole-extended bismaleimide (BM5) was obtained after precipitation in acetonitrile.

[0166] Analysis: GPC: M n : 6.7 kDa, M w : 14.0 kDa, PDI: 2.1. 1H NMR (500 MHz, THF-d8): δ = 10.60 (s), 9.41 - 9.37 (m), 8.44 (d, J = 4.9 Hz), 8.38 (d, J = 7.3 Hz), 8.28 (d, J = 8.3 Hz), 8.10 (d, J = 8.4 Hz), 7.83 (d, J = 8.4 Hz), 7.31 (t, J = 6.8 Hz), 7.25 (d, J = 8.7 Hz), 6.94 (s), 6.74 (s), 6.69 (d, J = 8.3 Hz), 3.83 (t, J = 6.3 Hz), 3.43 (t, J = 7.1 Hz), 3.20 (s), 3.11 (pd, J = 7.5, 4.9 Hz), 2.35 (q, J = 6.7, 6.2 Hz), 2.07 (d, J = 12.6 Hz), 1.71 (d, J = 15.3 Hz), 1.60 - 1.49 (m), 1.49 - 1.38 (m), 1.37 - 1.22 (m), 1.14 - 1.08 (m), 0.89 (t, J = 7.2 Hz) ppm. B-4 Synthesis of BM6 BM6 was prepared in a similar manner to BM5 according to B-2, except that Priamine™ was used instead of diamine (2).

[0167] [ka]

[0168] B-5 Synthesis of BM7

[0169] [ka]

[0170] Pripol acid chloride (3) (12 mmol, 7.2 g) was dissolved in 50 mL of dry DMAc and triethylamine (60 mmol, 6 g). Diaminobenzoxazole (4) (Biosynth Carbosynth Limited, CAS: 16363-53-4, 6 mmol, 1.35 g) was added at 0° C. and the reaction mixture was stirred at room temperature for 2 h. Then, 2-maleimidoethylamine hydrochloride (CAS: 134272-64-3, AstaTech, 12 mmol, 2.1 g) was added and the mixture was stirred again at room temperature for 2 h. Benzoxazole-extended bismaleimide (BM7) was obtained after precipitation in acetonitrile (6.9 g, 64%).

[0171] Analysis: GPC: M n : 2.9 kDa, M w : 4.4 kDa, PDI: 1.5. 1 H NMR (500 MHz, THF-d8): δ = 10.60 (wide s), 9.29 (s), 8.14 (d, J = 8.3 Hz), 7.84 (d, J = 8.4 Hz), 7.55 (d, J = 8.6 Hz), 7.29 (d, J = 8.8 Hz), 6.94 (s), 6.78 (s), 3.68 - 3.56 (m), 3.38 - 3.14 (m), 2.64 - 2.59 (m), 2.37 (q, J = 6.5 Hz), 2.26 (dt, J = 22.6, 7.0 Hz), 1.75 (d, J = 16.7 Hz), 1.61 (dt, J = 14.2, 6.8 Hz), 1.44 (s), 1.40 (s), 1.33 (s), 0.92 (q, J = 9.6, 8.1 Hz) ppm. B-6 Synthesis of BM8

[0172] [ka]

[0173] Adamantane-1,3-dicarboxylic acid (Accela, 4.5 g, 20 mmol) was dissolved in NMP (80 mL) together with CaCl2 (4.9 g, 44 mmol), pyridine (12.7 g, 160 mmol) and triphenyl phosphite (15.5 g, 50 mmol). Priamine™ (12.5 g, 24 mmol) and diaminobenzoxazole (4) (Biosynth Carbosynth Limited, CAS: 16363-53-4, 16 mmol, 3.6 g) were added and the reaction mixture was stirred at 120°C for 3 h, cooled to room temperature and precipitated by adding 500 mL of ethanol. The solid was washed several times with ethanol, warm water and again with ethanol and dried in vacuum. The intermediate was suspended in p-xylene (100 mL), carefully mixed with methanesulfonic acid (13.9 g, 144 mmol), triethylamine (14 g, 140 mmol) and maleic anhydride (4.9 g, 50 mmol) and refluxed for 5 h using a Dean-Stark apparatus. After cooling to room temperature, the product was precipitated by the addition of ethanol (300 mL). After drying in vacuum, a brown resin was obtained (BM8) (18 g, 69%).

[0174] Analysis: GPC: M n : 4.4 kDa, M w : 9.7 kDa, PDI: 2.2. 1 H NMR (500 MHz, THF-d8) δ = 10.26 (s), 9.14 - 8.89 (m), 8.54 - 8.24 (m), 8.19 - 7.82 (m), 7.72 - 7.40 (m), 6.91 (s), 6.76 (s), 6.71 (s), 3.44 (t, J = 7.2 Hz), 3.27 - 3.00 (m), 2.95 (dt, J = 14.8, 5.1 Hz), 2.53 (septet, J = 9.9, 7.5 Hz), 2.30 - 2.04 (m), 2.02 - 1.76 (m), 1.59 - 1.07 (m), 0.88 (q, J = 11.3, 8.7 Hz) ppm. C. Dynamic Mechanical Testing dynamic mechanical analysis Free-standing films were prepared as follows: A concentrated solution of oligomer in anisole was mixed with photoinitiator and structural additives and slit-coated onto a glass substrate. The resulting film was first dried at room temperature and then on a hotplate at 100° C. for 30 min. The film was cured via thermal curing at 230° C. for 60 min and finally removed from the substrate after immersion in water. The free-standing film was allowed to air dry for 20 h. Dynamic mechanical analysis (DMA) was performed on a Netzsch DMA242E instrument in air at a heating rate of 3 K / min.

[0175] C-1 Example 1 A blend of structural additive BMI-689 (10%) from Designer Molecules with BM4 and 5% Irgacure OXE2 as initiator resulted in soft films with a Tg around 50°C (see Figure 2).

[0176] C-2 Example 2 A blend of structural additive BMI-689 (10%) from Designer Molecules with BM6 and 5% Irgacure OXE2 as an initiator resulted in a soft film with a Tg of 67° C. (see FIG. 3).

[0177] C-3 Example 3 A blend of structural additive BMI-689 (10%) from Designer Molecules with BM8 and 5% Irgacure OXE2 as an initiator resulted in a soft film with a Tg of 106° C. (see FIG. 4).

[0178] D Conclusion Despite having a large structural proportion of aliphatic chain segments, the introduction of benzoxazole units into the extended bismaleimides significantly increases the Tg of these systems.

[0179] The membrane containing the polymer BMI-3000 from Designer Molecules, which has a lower ratio between the rigid aromatic units and the aliphatic chain segments, exhibits a Tg of 41° C., which is significantly lower than the Tg of the membrane obtained from the bismaleimide compound according to the invention. The same is true for the polymer membrane obtained only from the structural additive BMI-689 from Designer Molecules, which exhibits a Tg of 42° C.

[0180] BMI-3000:

[0181] [ka]

[0182] BMI-689:

[0183] [ka]

Claims

1. Formulas (1) to (4): 【Chemistry 1】 [In the formula, A, in each occurrence independently, is a linking unit that includes one or more divalent benzoxazole, divalent benzothiazole, or divalent benzimidazole moieties; B, in each occurrence independently, is a linking unit that includes one or more of an aliphatic, aromatic, or siloxane moiety; R ａ and R ｂ are, independently, and in each occurrence independently of each other, a linking unit that includes one or more of an aliphatic, aromatic, or siloxane moiety; R ｃ is R ａ or R ｂ and X, in each occurrence independently, is a functional group selected from the list consisting of an amide group, an ether group, an ester group, and a urethane group; R １ is H or alkyl having 1 to 5 carbon atoms; R ２ is H or alkyl having 1 to 5 carbon atoms; t is an integer from 1 to 12; u is 0 or 1; n is an integer from 1 to 60; m is an integer from 1 to 60. Bismaleimide compounds represented by one of the following:

2. A is, in each occurrence independently of one another, a group represented by formula (5a) to (5c): 【Chemistry 2】 [In the formula, 【Transformation 3】 represents the binding site; Q is O, NH or S; D are, independently in each occurrence, a divalent aromatic group preferably having 4 to 20 carbon atoms, a divalent aliphatic group preferably having 2 to 20 carbon atoms, or a divalent mixed aromatic aliphatic group preferably having 6 to 30 carbon atoms, which may contain one or more heteroatoms selected from N, O and S, and which may be substituted with one or more substituents selected from the list consisting of halogen, alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 5 carbon atoms, phenyl and phenyloxy; G is -O-, -S-, -CO-, -(CO)-O-, -O-(CO)-, -S-(CO)-, -(CO)-S-, -O-(CO)-O-, -(CO)-NR 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-(CO)-O-, -O-(CO)-CH=CH-, or a single bond, wherein R ０１ and R ０２ are, independently of each other, H or alkyl having 1 to 5 carbon atoms; Y ０１ and Y ０２ are each independently H, alkyl having 1 to 5 carbon atoms, phenyl, F, Cl or CN.

2. The bismaleimide compound of claim 1, wherein the bismaleimide compound is represented by one of the following:

3. 3. The bismaleimide compound of claim 2, wherein D is a phenylene moiety.

4. 4. The bismaleimide compound according to claim 2 or 3, wherein G is O or a single bond.

5. 4. The bismaleimide compound according to claim 1, wherein B is, independently in each occurrence, a substituted or unsubstituted aliphatic moiety having 2 to 100 carbon atoms, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 100 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 100 carbon atoms, a substituted or unsubstituted siloxane moiety having 2 to 50 silicon atoms, or a combination thereof.

6. B is, in each occurrence independently of each other, a group of formula (6a) or (6b): 【Chemistry 4】 [In the formula, 【Transformation 5】 represents the binding site; x and y are, independently of each other, integers from 0 to 10; R Ｉ and R ＩＩ are each independently a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, a linear alkylene group having 2 to 10 carbon atoms, or a branched alkylene group having 3 to 10 carbon atoms. The bismaleimide compound according to any one of claims 1 to 3, which is represented by one of the following formulas:

7. R ａ and R ｂ are independently, and in each occurrence independently of each other, a substituted or unsubstituted aliphatic moiety having 2 to 100 carbon atoms, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 100 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 100 carbon atoms, a substituted or unsubstituted siloxane moiety having 2 to 50 silicon atoms, or a combination thereof; R ｃ But, R ａ or R ｂ That is, The bismaleimide compound according to any one of claims 1 to 3.

8. R ａ and R ｂ are independently, and in each occurrence independently of each other, a substituted or unsubstituted aliphatic moiety having 2 to 100 carbon atoms, which optionally contains one or more of a C═C double bond, a C≡C triple bond, or an amide group; R ｃ But, R ａ or R ｂ That is, The bismaleimide compound according to any one of claims 1 to 3.

9. R ａ and R ｂ independently, and in each occurrence independently of one another, represent the formulas (8a) to (8d): 【Transformation 6】 [In the formula, 【Transformation 7】 represents the binding site; x and y are, independently of each other, integers from 0 to 10; R Ｉ and R ＩＩ are each independently a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, a linear alkylene group having 2 to 10 carbon atoms, or a branched alkylene group having 3 to 10 carbon atoms. The bismaleimide compound according to any one of claims 1 to 3, which is represented by one of the following formulas:

10. X is, in each occurrence, independently of each other, —(CO)—NR ３ -, -NR ３ -(CO)-, -O-, -(CO)-O-, -O-(CO)-, -O-(CO)-NR ３ -or-NR ３ -(CO)-O-, where R ３ The bismaleimide compound according to any one of claims 1 to 3, wherein is H or alkyl having 1 to 5 carbon atoms.

11. 1. A method for forming a dielectric polymer material, comprising the steps of: (i) providing a formulation comprising one or more bismaleimide compounds according to any one of claims 1 to 3; (ii) curing the formulation; 1. A method for forming a dielectric polymer material, comprising:

12. 12. The method for forming a dielectric polymer material of claim 11, wherein the formulation further comprises one or more additional compounds capable of reacting with the bismaleimide compound.

13. 12. The method for forming a dielectric polymer material of claim 11, wherein the formulation includes one or more inorganic or organic fillers.

14. A dielectric polymer material obtainable by the method of claim 11.

15. A dielectric polymer material comprising at least one repeating unit derived from the bismaleimide compound according to any one of claims 1 to 3.

16. The repeating units are represented by the formulas (10) to (13): 【Transformation 8】 [In the formula, A, B, R ａ , R ｂ , X, n and m are defined as in claim 1.

16. The dielectric polymer material of claim 15, comprising a structural unit represented by one of:

17. 15. An electronic device comprising the dielectric polymer material of claim 14.

18. 20. The electronic device of claim 17, wherein the electronic device is a microelectronic device and the dielectric polymer material is included as a repassivation material in a redistribution layer of the microelectronic device.

19. An electronic device comprising the dielectric polymer material of claim 15.

20. The electronic device described in claim 19, wherein the electronic device is a microelectronic device and the dielectric polymer material is included as a repassivation material in a redistribution layer of the microelectronic device.

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