Oligoamide-extended bismaleimide based dielectric materials

Abstract

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

Description

[Technical field]

[0001] FIELD OF THEINVENTION The present invention relates to a novel class of dielectric polymer materials that are particularly suitable for the manufacture of electronic devices. The dielectric polymer materials are formed by reacting new types of bismaleimide compounds and exhibit a balanced and advantageous profile of favorable material properties, especially with respect to the requirements in advanced electronic packaging applications, such as, for example, wafer level packaging (WLP) and low dielectric adhesive applications. The dielectric polymer materials of the present invention exhibit a balanced and advantageous 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, high tensile strength; (b) favorable dielectric properties, such as low dielectric constant and low dissipation factor; (c) good adhesion properties, especially high adhesion strength to copper and SiO2 passivated wafers; and (d) 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 oligoamide-extended bismaleimide compounds are described herein. Such compounds are photostructurable and can be used as starting materials for various applications in electronic device manufacturing, such as packaged electronic devices (including passivation of conductive or semiconducting components of redistribution layers (RDL) or die attach), for preparing repassivation layers in thin film formulations and / or adhesive formulations. Moreover, the bismaleimide compounds have excellent film-forming ability and are easy to form dielectric polymers as spin-on materials.

[0003] The bismaleimide compounds of the present invention have an oligomeric structure having an oligoamide extended repeat unit in the middle portion of the molecule and a maleimide group at each end of the molecule. Additionally, a method for forming said dielectric polymer material is provided.Furthermore, the present invention relates to a dielectric polymer material and an electronic device comprising said polymer material as a dielectric material. The bismaleimide compounds and related dielectric polymer materials of the present invention enable cost-effective and reliable production of microelectronic devices with a significantly reduced number of defective devices caused by mechanical deformation (warpage) due to undesirable thermo-mechanical expansion. [Background technology]

[0004] 2. Background of the Invention As solid-state transistors began to replace vacuum tube technology, it became possible to attach electronic components such as resistors, capacitors, and diodes directly to the printed substrate of the card with wire leads, establishing the basic building block or level of packaging still in use today. Complex electronic functions often require many more individual components than can be interconnected on a single printed circuit card. The capability of multi-layer cards was accompanied by the development of three-dimensional packaging of daughter cards onto multi-layer motherboards. Integrated circuits allow many individual circuit elements such as resistors and diodes to be embedded into separate, relatively small components known as integrated circuit chips or dies. However, despite the incredible degree of circuit integration, multiple packaging levels are usually required, in part due to the technology of the integrated circuit itself. Integrated circuit chips are very fragile and have very small terminals. The first level of packaging fulfills the primary functions of providing mechanical protection, cooling, and electrical connection to the delicate integrated circuit. Some components (high power resistors, mechanical switches, capacitors) cannot be easily integrated onto the chip, so at least one additional packaging level, such as a printed circuit card, is utilized. For very complex applications such as mainframe computers, a hierarchy of multiple packaging levels is required.

[0005] A variety of advanced packaging technologies exist to meet the requirements of today's semiconductor industry. 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 thin substrates, redistribution layers, and other components such as high-resolution interconnects. End consumer markets are constantly pushing for smaller and thinner devices with lower cost and higher functionality. This is driving the need for next-generation packaging with finer features and improved reliability at competitive manufacturing costs.

[0006] Wafer-level packaging (WLP) is one of the most promising semiconductor packaging technologies for the next generation of small, high-performance electronic devices. In general, WLP is the process of packaging integrated circuits while they are still part of a wafer. This contrasts with the more traditional method of cutting the wafer into individual circuits and then packaging them. WLP is based on redistribution layers (RDLs), which allow connections between the die and solder balls, improving signal propagation and enabling smaller form factors (see Figure 1). The main application areas for WLP are smartphones and wearables due to size constraints.

[0007] With current materials, the WLP process is limited to applications with moderate chip sizes. The reason for this limitation is based on inadequate thermomechanical properties and non-optimized processing of these materials. Dielectric materials used for next-generation microchip RDLs must meet certain requirements. In addition to a low dielectric constant, several thermomechanical properties play an important role, such as, for example, high thermal stability, high glass transition temperature (Tg), low coefficient of thermal expansion (CTE), high elongation at break, and high tensile strength.

[0008] An important class of materials that meets some of the above requirements are imide-extended maleimide compounds, which have been described in various state-of-the-art publications. US2004 / 0225026A1 and US2011 / 0130485A1 relate to thermosetting (adhesive) compositions comprising imide-extended mono-, bis-, or polymeric imide compounds. The imide-extended maleimide compounds are prepared by condensing a suitable anhydride with a suitable diamine to obtain amine-terminated compounds. These compounds are then condensed with an excess of maleic anhydride to obtain the imide-extended maleimide compounds. The imide-extended maleimide compounds, when incorporated into thermosetting compositions, are said to reduce the brittleness and increase the toughness of the compositions without sacrificing thermal stability. US2011 / 0049731A1 and US2013 / 0228901A1 relate to materials and methods for reducing stress in semiconductor wafer passivation layers. Compositions containing low modulus photoimageable polyimides for use as passivation layers, and semiconductor wafers and devices made therefrom that include the passivation layers are described.

[0009] US 2017 / 0152418 A1 relates to maleimide adhesive films made from thermosetting maleimide resins containing imide-extended monomeric maleimides, bismaleimide compounds, and polymeric maleimide compounds. The maleimide adhesive films are said to be photostructurable and suitable for the manufacture of electronic devices, integrated circuits, semiconductor devices, passive devices, solar cells, solar cell modules, and / or light emitting diodes.

[0010] However, the imide-extended maleimide compounds described above have poor solubility in common solvents used in industry and also have poor thermomechanical properties such as low glass transition temperature (Tg) and coefficient of thermal expansion (CTE), etc. Material modifications aimed at reducing the CTE of this material class make the material very brittle and reduce the elongation at break, so it cannot be used in WLP applications. Another trend in the semiconductor industry concerns the demand for materials with low dielectric properties (low dielectric constant, low dielectric tangent) in the high frequency range. With the increase in signal transmission speed on printed circuit boards, the frequency of the signals has also increased. In addition, the 5G era requires reliable materials with unique properties that meet specific requirements. In general, for low dielectric constant materials, the polarity of these insulating films is usually low, resulting in poor adhesion strength. New materials that combine low-loss dielectric behavior with good adhesion properties are of great interest for the development of various future applications.

[0011] WO2019 / 141833A1 relates to a dielectric polymer having excellent film-forming ability, excellent mechanical properties, low dielectric constant, and low thermal expansion coefficient. The dielectric polymer is prepared from a polymerizable compound having a mesogenic group, and can be used as a dielectric material for preparing a passivation layer of an electronic device. Although these materials have many beneficial properties, some properties, such as glass transition temperature and processability, need to be further enhanced or improved in order to realize the full potential of these materials. Polyamide materials for electrical and electronics applications are described by R. Rulkens et al. in Polymer Science: A Comprehensive Reference, Volume 5, 2012, 431―467. However, such materials have poor adhesive strength and, from a material property standpoint, the above mentioned compounds and materials do not meet all the requirements for a dielectric suitable for modern packaging applications, especially photoimageable dielectrics.

[0012] Objective of the invention The object of the present invention is to overcome the shortcomings and disadvantages of the prior art and to provide a new class of dielectric polymer materials that exhibit a balanced and advantageous profile of favorable material properties, in particular with regard to the requirements in advanced electronic packaging applications, such as, for example, Wafer Level Packaging (WLP), as well as for low dielectric adhesive applications.

[0013] It is therefore an object of the present invention to provide a crystalline silicon-based composite material that exhibits a balanced and advantageous profile of material properties including, by way of example, (a) favorable thermo-mechanical properties such as, by way of example, 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, by way of example, low dielectric constant and low dissipation factor; (c) good adhesion properties, especially high adhesion strength to copper and SiO2 passivated wafers; and (d) good processability from solvents commonly used in the semiconductor industry. The present invention provides a dielectric polymer material. It is a further object of the present invention 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 various applications in electronic device manufacturing, such as for example for the preparation of repassivation layers in packaged electronic devices (including passivation of conductive or semiconducting components in redistribution layers (RDL) or die attach), thin film formulations and / or adhesive formulations. Furthermore, said bismaleimide compounds should have good film forming capabilities and be easy to process from solvents commonly used to form dielectric polymers as spin-on materials in the semiconductor industry.

[0014] It is further an object of the present invention 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.

[0015] It is an object of the present invention that bismaleimide compounds and related dielectric polymer materials enable cost-effective and highly reliable manufacturing of microelectronic devices with a significantly reduced number of defective devices caused by mechanical deformation (warpage) due to undesirable thermo-mechanical properties. Summary of the Invention

[0016] SUMMARY OF THE PRESENT APPLICATION The present inventors have surprisingly found that the above objectives are achieved by dielectric polymer materials formed from new types of bismaleimide compounds that exhibit a balanced and advantageous profile of material properties including (a) favorable thermomechanical properties such as, for example, 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, for example, low dielectric constant and low dissipation factor, (c) good adhesion properties, especially to copper and SiO2 passivated wafers, and (d) good processability from solvents commonly used in the semiconductor industry.

[0017] The bismaleimide compound of the present invention is represented by one of the formulas (1) to (4): [ka] [ka] During the ceremony, A and B are, independently and at each occurrence independently of one another, a linking unit comprising one or more aliphatic, aromatic, or siloxane moieties, where optionally A, B, or A and B contain a cardo or spiro center; R a and R b are, independently and at each occurrence independently of each other, a linking unit that contains one or more aliphatic, aromatic, or siloxane moieties; R c is R a or Rb and X is, independently of each other, an amide 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; n is an integer from 1 to 60, preferably 1 to 50, more preferably 2 to 30, and most preferably 3 to 20; and m is an integer from 1 to 60, preferably 1-50, more preferably 2-30, and most preferably 3-20.

[0018] Said bismaleimide compounds are used as monomer 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.

[0019] below: (i) providing a formulation comprising one or more bismaleimide compounds of the present invention; and (ii) curing the formulation A method for forming a dielectric polymer material comprising the steps of:

[0020] Further provided is a dielectric polymer material obtainable or obtainable by the method for forming a dielectric polymer material described above. Further provided is a dielectric polymeric material comprising at least one repeat unit derived from a bismaleimide compound according to the present invention. Finally, there is provided an electronic device comprising a dielectric polymer material according to the present invention. Preferred aspects of the invention are set out below and in the dependent claims. [Brief description of the drawings]

[0021] [Figure 1]Schematic diagram of a fan-out wafer-level packaging (WLP) structure. [Diagram 2] DMA of the polymeric material obtained from oligomer (3) cured with 5 wt.-% Irgacure OXE-02. [Diagram 3] DMA of polymeric material obtained from oligomer (3) cured with 10 wt.-% bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS RN: 105391-33-1, TCI) and 5 phr of Irgacure OXE-02 as structural additive. [Figure 4] DMA of a polymeric material obtained from oligomer (3) cured with 10 wt.-% pentaerythritol tetraacrylate (CAS RN: 4986-89-4 Sigma-Aldrich (Merck)) and 5 phr Irgacure OXE-02 as structural additives. [Diagram 5] DMA of polymeric material obtained from oligomer (4) cured with 5 wt.-% Irgacure OXE-02. [Figure 6] DMA of polymeric material obtained from oligomer (4) cured with 10 wt.-% bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS RN: 105391-33-1, TCI) and 5 phr Irgacure OXE-02 as structural additives. [Figure 7] DMA of polymeric material obtained from oligomer (5) cured with 5 wt.-% Irgacure OXE-02. [Figure 8] DMA of polymeric material obtained from oligomer (5) cured with 10 wt.-% bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS RN: 105391-33-1, TCI) and 5 phr Irgacure OXE-02 as structural additives. [Figure 9] DMA of polymeric material obtained from oligomer (6) cured with 5 wt.-% Irgacure OXE-02. [Figure 10]DMA of a polymeric material obtained from oligomer (6) cured together with 20 wt.-% tetra(ethylene glycol) diacrylate (CAS RN: 17831-71-9, Merck Sigma-Aldrich) and 5 phr Irgacure OXE-02 as structural additives. [Figure 11] DMA of polymeric material obtained from oligomer (7) cured with 5 wt.-% Irgacure OXE-02. [Figure 12] DMA of polymeric material obtained from oligomer (7) cured with 30 wt.-% tetra(ethylene glycol) diacrylate (CAS RN: 17831-71-9, Merck SigmaAldricj) and 5 phr Irgacure OXE-02 as structural additives. [Figure 13] DMA of polymeric material obtained from oligomer (8) cured with 5 wt.-% Irgacure OXE-02. [Figure 14] DMA of polymeric material obtained from oligomer (9) cured with 5 wt.-% Irgacure OXE-02. [Figure 15] DMA of polymeric material obtained from oligomer (9) cured with 10 wt.-% bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS RN: 105391-33-1, TCI) and 5 phr Irgacure OXE-02 as structural additives. [Figure 16] DMA of polymeric material obtained from reference material BMI3000 (commercial grade, Designer Molecules Inc.) cured with 5 wt.-% Irgacure OXE-02. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0022] Detailed Description definition The term "linking unit" as used herein refers to an organic structural unit that links two or more parts of a molecule. A linking unit is usually composed of different moieties. A linking unit may be divalent or polyvalent, preferably divalent. The term "spiro compound" as used herein refers to a compound having a spiro center consisting of two rings connected at right angles through one common quaternary bond atom. Usually, 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 are connected through a common quaternary bond atom that defines the spiro center. The spiro center, together with the adjacent groups attached to it, forms the so-called "spiro moiety" and can be considered as the characteristic structural unit of the spiro compound. The spiro moiety is typically attached to at least two adjacent further structural units of the chemical compound. Polymeric spiro compounds are also called "spiropolymers".

[0023] The term "cardo polymers" as used herein describes a subgroup of polymers in which 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 positioned perpendicular to the plane of the polymer chain and form a loop structure. Cardo structures are very similar to spiro structures, but only one ring is attached to the cardo center, whereas 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 can be considered as the characteristic structural unit of cardo polymers. The cardo moiety is typically attached to at least two adjacent further structural units of a chemical compound.

[0024] The term "aliphatic moiety" as used herein refers to a straight-chain, branched-chain, 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, preferably, -C(O)Rv ,-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 a C=C double bond, a C≡C triple bond, an amide, a carbamate, a carbonate, an ester, an ether, a secondary or tertiary amine, and a keto. The aliphatic moiety is typically attached to at least two adjacent further structural units of the chemical compound.

[0025] The term "aromatic moiety" as used herein refers to a monocyclic or polycyclic aromatic that forms part of the structure of a chemical compound. A polycyclic aromatic unit encompasses two or more connected aromatic ring systems fixed in one plane. The aromatic moiety can be (i) a hydrocarbon aromatic moiety or (ii) a heteroatom-containing aromatic moiety, also called a heteroaromatic moiety. A hydrocarbon aromatic moiety contains an aromatic ring structure composed of carbon atoms, whereas a heteroaromatic moiety contains an aromatic ring structure and furthermore a heteroaromatic unit contains one or more heteroatoms selected from N, O, S, and P. The aromatic moiety can be unsubstituted or 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 aromatic moiety is typically attached to at least two adjacent further structural units of the chemical compound.

[0026] The term "siloxane moiety" as used herein refers to a structural unit of a chemical compound that contains at least one Si-O-Si bond. The siloxane moiety may be linear, branched, or cyclic. The siloxane moiety may be unsubstituted or 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 siloxane moiety is typically attached to at least two adjacent further structural units of the chemical compound.

[0027] The term "polymer" includes, but is not limited to, homopolymers, copolymers, such as block, random, and alternating copolymers, terpolymers, quaternary polymers, etc., and blends and modifications thereof. Furthermore, unless otherwise specified, 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 weight, whose structure essentially comprises multiple repeats of units (i.e., repeat units) derived from molecules of actual or conceptually lower relative mass (i.e., monomers). Polymers are usually mixtures of molecules with different chain lengths, and therefore have a molar mass distribution. The term "oligomer" refers to a molecular complex composed of a small number of monomer units, in contrast to a polymer, 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 usually mixtures of molecules with different chain lengths and therefore have a molar mass distribution.

[0028] The term "monomer" as used herein refers to a molecule that can undergo polymerization, thereby providing a building block (repeating unit) to the essential structure of a polymer or oligomer. The term "homopolymer" as used herein refers to a polymer derived from one type of monomer (real, implicit or hypothetical).

[0029] The term "copolymer" as used herein generally refers to any polymer derived from two or more monomers and containing two or more corresponding repeat units. In one embodiment, a copolymer is the reaction product of two or more monomers and thus contains two or more corresponding repeat units. Preferably, the copolymer contains two, three, four, five or six repeat units. Copolymers obtained by copolymerization of three monomer types are also called terpolymers. Copolymers obtained by copolymerization of four monomer types are also called quaterpolymers. Copolymers can exist as block, random and / or alternating copolymers.

[0030] As used herein, the term "block copolymer" refers to polymers in which adjacent blocks are structurally different, i.e., adjacent blocks are derived from different types of monomers, or from the same type of monomers but contain repeat units having different compositions or sequence distributions of the repeat units. Furthermore, as used herein, the term "random copolymer" refers to a polymer formed of macromolecules in which the probability of finding a given repeat unit at any site in the chain does not depend on the nature of the adjacent repeat units. Typically, in random copolymers, the sequence distribution of the repeat units follows Bernoulli statistics.

[0031] The term "alternating copolymer" as used herein refers to a copolymer consisting of macromolecules that contain two types of repeat units in alternating order.

[0032] "Electronic packaging" is a major area of ​​electronics engineering and encompasses a wide variety of technologies. It refers to the insertion of discrete components, integrated circuits, MSI (medium-scale integrated circuit) and LSI (large-scale integrated circuit) chips (usually attached to a lead frame by beam leads) through holes in a multilayer circuit board (also called a card) into a plate, where they are soldered into place. Packaging of electronic systems must consider protection from mechanical damage, cooling, high frequency noise emissions, protection from maintenance due to electrostatic discharge, operator convenience, and cost.

[0033] The term "microelectronic device" as used herein refers to electronic devices of very small electronic designs and components. Usually, but not always, this means micrometer scale or smaller. These devices are typically made from semiconductor materials and contain one or more microelectronic components that are interconnected in a packaged structure to form the microelectronic device. Many of the electronic components of typical electronic designs are available as microelectronic equivalents. These include transistors, capacitors, inductors, resistors, diodes, and of course insulators and conductors can all be found within a microelectronic device. Due to the unusually small size of the components, leads, and pads in microelectronics, proprietary wiring techniques such as wire bonding are also often used.

[0034] Preferred Aspects Bismaleimide Compounds The present invention relates to a bismaleimide compound represented by one of the formulas (1) to (4): [ka] [ka] During the ceremony A and B are, independently and at each occurrence independently of one another, a linking unit comprising one or more aliphatic, aromatic, or siloxane moieties, where optionally A, B, or A and B contain a cardo or spiro center; R a and R b are, independently and at each occurrence independently of each other, a linking unit that contains one or more aliphatic, aromatic, or siloxane moieties; R c is R a or R b and X is, independently of each other, an amide 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; n is an integer from 1 to 60, preferably 1 to 50, more preferably 2 to 30, and most preferably 3 to 20; and m is an integer from 1 to 60, preferably 1-50, more preferably 2-30, and most preferably 3-20. The bismaleimide compounds according to formula (3) or (4) contain two different repeat units, represented by the repeat units marked with the indices m and n, respectively. The compounds can therefore be considered as cooligomers, where the different repeat units may form blocks (block cooligomers), vary (alternating cooligomers), or be randomly distributed throughout the cooligomer (random cooligomers).

[0035] Preferably, in formula (1), (2), (3) and / or (4), A and B are independently, in each occurrence independently of the other, a linking unit which contains one or more aliphatic or aromatic moieties, and optionally A, B, or A and B contain a cardo or spiro center. More preferably, in formula (1), (2), (3) and / or (4), A is, in each case independently of one another, a linking unit comprising one or more cyclic aliphatic moieties, which may be optionally bridged, or an aromatic moiety, A optionally comprising a cardo or spiro center, and B is, in each case independently of one another, a linking unit comprising one or more cyclic aliphatic moieties, which may be optionally bridged, or an aromatic moiety, B optionally containing a cardo or spiro center.

[0036] In a preferred embodiment of the invention, A and B are independently and independently of each other at 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, wherein optionally A, B, or A and B contain a cardo center or a spiro center. In a more preferred embodiment of the invention, A is, at each occurrence, independently of each other, a substituted or unsubstituted cycloaliphatic moiety having 3 to 80 carbon atoms, which may be optionally bridged, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 80 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 80 carbon atoms, or a combination thereof, wherein A optionally contains a cardo center or a spiro center.

[0037] In a particularly preferred embodiment of the invention, A is, independently of each other occurrence, a substituted or unsubstituted cycloaliphatic moiety having 3 to 80 carbon atoms, which may be optionally bridged, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 80 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 80 carbon atoms, or a combination thereof, where A optionally contains a cardo or spiro center, and B, at each occurrence, independently of each other, is a substituted or unsubstituted cycloaliphatic moiety having 3 to 80 carbon atoms, which may be optionally bridged, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 80 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 80 carbon atoms, or a combination thereof, where B optionally contains a cardo center or a spiro center. It is preferred that A is different from B.

[0038] Preferably, in formula (1), (2), (3) and / or (4), A is, independently of each other at each occurrence, represented by formula (5): [ka] During the ceremony: A 21 , A 22 and A 23 are independently and independently of each other at each occurrence a divalent aromatic group, preferably having 4 to 30 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, optionally containing one or more heteroatoms selected from N, O and S, and optionally substituted with one or more substituents selected from the list consisting of halogen, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, and aryloxy having 6 to 10 carbon atoms, wherein one or more A 21 , A 22 and A 23 optionally containing a cardo center or a spiro center;

[0039] G 21 , G 22 , G 23 and G 24 are independently and independently of each other at each occurrence -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; Y 01 and Y 02 are each independently H, an alkyl having 1 to 5 carbon atoms, phenyl, F, Cl, or CN; and k and l are each independently 0, 1, 2, 3 or 4, preferably 0 or 1, more preferably k=0 and l=0, or k=1 and l=0.

[0040] Preferably, A 21 , A 22 and A 23 are independently and independently of each other at each occurrence represented by one of the formulas (5a) to (5x): [ka] [ka] [ka] During the ceremony [ka] represents the binding site, L is an alkyl having 1 to 5 carbon atoms, halogenyl, Ph or CN, preferably methyl, F, Cl, Ph or CN; R Alk is alkyl having 1 to 5 carbon atoms, Q is O, S or CH2; z is an integer from 1 to 20, preferably from 2 to 15, more preferably from 5 to 10, and most preferably 7; and q is an integer from 0 to 4, preferably from 0 to 2, more preferably 0 or 1, and most preferably 0.

[0041] Preferably, in formula (3) and / or (4), B is represented, independently of each other at each occurrence, by one of the formulae (6a) to (6d): [ka] During the ceremony [ka] represents the binding site, L is, independently of each other at each occurrence, an alkyl having 1 to 5 carbon atoms, halogenyl, Ph or CN, preferably methyl, F, Cl, Ph or CN, q is an integer from 0 to 4, preferably from 0 to 2, more preferably 0 or 1, and most preferably 0; and v is an integer from 0 to 12, preferably from 2 to 10, more preferably from 4 to 8, and most preferably 7.

[0042] In a preferred embodiment of the present invention, R a and R b are independently and independently of each other at 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 a combination thereof; and R c is R a or R b It is.

[0043] In a more preferred embodiment of the present invention, R a and R bare, independently and at 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, which optionally contains one or more C=C double bonds, C≡C triple bonds or amide groups, preferably -NH-(CO)- or -(CO)-NH-, and R c is R a or R b It is. R a is R b It is preferable that it is different from.

[0044] Preferably, in formula (1), (2), (3) and / or (4), R a and R b are represented independently and independently of each other at each occurrence by one of the formulas (7a) to (7d): [ka] During the ceremony [ka] represents the binding site, x and y are each independently an integer from 0 to 12, preferably from 1 to 10, more preferably from 3 to 9; and R I and R II are each independently a linear alkyl group having 1 to 12 carbon atoms, preferably 1 to 9 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, preferably 3 to 9 carbon atoms, a linear alkylene group having 2 to 12 carbon atoms, preferably 2 to 9 carbon atoms, or a branched alkylene group having 3 to 12 carbon atoms, preferably 3 to 9 carbon atoms, more preferably -CH 13 , C7H 15 ,-C8H 17, —CH2CH(C2H5)C4H9, —CH2—CH2—CH=CH—C3H7 or —CH2—CH2—CH=CH—C5H 11 It is.

[0045] More preferably, in formula (1), (2), (3) and / or (4), R a and R b are represented independently and independently of each other at each occurrence by one of the formulas (8a) to (8d), [ka] During the ceremony [ka] represents the binding site. Preferably, in formula (1), (2), (3) and / or (4), X is, independently of each other at 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.

[0046] Particularly preferred bismaleimide compounds according to formula (1), (2), (3) and / or (4) are [ka] [ka] [ka] [ka] [ka] It is.

[0047] The bismaleimide compounds of the present invention can be prepared by any standard synthesis. Usually, the compounds are retrosynthetically cut into smaller units and formed stepwise from suitable precursor compounds. For this purpose, known standard reactions can be used. It has proven to be particularly advantageous to attach the maleimide group at a later stage of the synthesis, typically at the very end of the synthesis. In this way, undesired side reactions and premature polymerization of the compounds can be avoided.

[0048] The maleimide group is a functional group capable of polymerization reactions, such as radical polymerization, ionic chain polymerization, polyaddition, polycondensation, or capable of undergoing polymerization-like reactions, such as addition or condensation, for example, on a polymer backbone. The present invention further provides a method of forming a dielectric polymer material comprising repeat units derived from one or more bismaleimide compounds according to the present invention. The dielectric polymer material may be linear or crosslinked. The 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; and (ii) curing the formulation Includes steps.

[0049] 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, preferably to form a copolymer. Using basic chemical knowledge, a person skilled in the art may find and select, for a given bismaleimide compound of the invention, suitable additional compounds capable of reacting with the first one, preferably to form a copolymer.

[0050] Additional compounds that can react with the preferred bismaleimide compounds according to the present invention are selected from the list consisting of acrylates, epoxides, olefins, vinyl ethers, vinyl esters, polythiols, polyamines, and polymerimides.

[0051] 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 meth ... 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.

[0052] 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.

[0053] Preferred olefins are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, isoprene styrene, and vinyl ethylene. 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.

[0054] Preferred vinyl esters are vinyl formate, vinyl acetate, vinyl propanoate, 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.

[0055] A preferred polythiol is an organosulfur compound having two or more thiol functional groups. A particularly preferred polythiol is HS-(C n H 2n )—SH, where n=2 to 20, preferably 2 to 12; C n H 2n―1 (SH)3, where n=3-20, preferably 3-12; HS-Ar-SH, where Ar=substituted or unsubstituted C6-C 20 arylene, and HS—(CH2) m -Ar-(CH2) m -SH, where Ar = substituted or unsubstituted C6-C 20 arylene, and m=1-12.

[0056] Preferred polyamines are organic amine compounds having two or more amino functional groups. Specifically preferred polyamines are H2N-(C n H 2n )—NH2, where n=2-20, preferably 2-12; H2N—(C n H 2n NH)—NH2, where n=2 to 20, preferably 2 to 12; C n H 2n―1 (NH2)3, where n=3-20, preferably 3-12; H2N-Ar-NH2, where Ar=substituted or unsubstituted C6-C 20 Arylene; and H2N—(CH2) m -Ar-(CH2) m -H2N, where Ar = substituted or unsubstituted C6 -C 20Selected from the list consisting of arylene and m=1-12.

[0057] A preferred polyimide is a maleimide end-capped polyimide as described in US2004 / 0225026A1 and US2017 / 0152418A1, the disclosures of which are incorporated herein by reference. The polyimide is preferably a bismaleimide selected from compounds represented by the following formula (A) or formula (B): [ka] where R1 and Q1 are independently selected from the list consisting of structures derived from unsubstituted or substituted aliphatic, alicyclic, alkenyl, aryl, heteroaryl, siloxane, poly(butadiene-co-acrylonitrile) and poly(alkylene oxide); X1-X4 are each independently H or an alkyl group having 1-6 C atoms; and n=0-30; [ka] wherein R2 and Q2 are independently selected from the list consisting of structures derived from unsubstituted or substituted aliphatic, alicyclic, alkenyl, aryl, heteroaryl, siloxane, poly(butadiene-co-acrylonitrile) and poly(alkylene oxide); X5-X8 are each independently H or an alkyl group having 1-6 C atoms; R3 and R4 are each independently H or CH3, where at least one of R3 and R4 is CH3; and n=0-30. 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, aryloxy ... groups, substituted aryloxy groups, halogens, haloalkyl groups, cyano groups, nitro groups, nitrone groups, amino groups, amido groups, —C(O)H, acyl groups, oxyacyl groups, carboxyl groups, carbamate groups, sulfonyl groups, sulfonamide groups, sulfuryl groups, 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), which preferably contain a further terminal substituent.

[0058] Preferred substituents include 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 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 carbons), an acyl group, an oxyacyl group, a carboxyl group, a carbamate group, a sulfonyl group, a sulfonamide group, or a sulfuryl group.

[0059] In a more preferred embodiment of formulas (A) and (B), R1 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. Preferred aliphatic moieties are linear or branched chain C-C 50 Alkylene, more preferably a linear or branched chain C-C 36 It is alkylene.

[0060] Preferred alicyclic moieties are both aliphatic and cyclic, and contain one or more all-carbon rings, which may be substituted or unsubstituted and optionally 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 and Sp 1 and Sp 2 represent, independently of one another, an alkylene having 1 to 12 C atoms or a single bond. G represents a cycloalkylene having 3 to 12 C atoms, optionally mono- or polysubstituted by alkyl having 1 to 12 C atoms.

[0061] 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 preferably, the alkenyl moiety is a C-C 50 Alkenylene, most preferably C-C 36 It is alkenylene.

[0062] Preferred aromatic moieties include (i) hydrocarbon aromatic moieties such as arylene groups having 6 to 20 carbon atoms, more preferably 6 to 14 carbon atoms, which may be substituted or unsubstituted, and (ii) heteroaromatic moieties having 3 to 20 carbon atoms, preferably having 3 to 14 C atoms and one or more heteroatoms selected from N, O, S and P in the aromatic ring structure, which may be substituted or unsubstituted.

[0063] 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. Preferred poly(alkylene oxide) moieties are poly(C1-C 12 alkylene oxide) moiety.

[0064] 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. 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, and 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, and may be surface modified with a capping agent. Preferred organic fillers are diamondoids or organic polymer particles. Preferred diamondoids are adamantane (C 10 H 16 ), Icean (C 12 H 18 ), BC-8(C14 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 ). Preferably, the total content of the filler 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. In a preferred embodiment, the formulation is provided on a surface of a substrate in step (i) and forms a dielectric polymeric material on said surface after curing in step (ii).The substrate is preferably a substrate of an electronic or microelectronic device.

[0065] Preferably, the formulation is provided in step (i) 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 in a single coating. The method of applying the composition in step (i) is not particularly limited.Preferred application methods are dispensing, dipping, screen printing, stencil printing, roller coating, spray coating, slot coating, slit coating, spin coating, gravure printing, flexographic printing or inkjet printing.

[0066] The bismaleimide compounds of the present invention can be provided in the form of formulations which are suitable for gravure, flexographic and / or inkjet printing. For the preparation of such formulations, ink base formulations as known from the state of the art can be used. Alternatively, the bismaleimide compounds of the present invention may be provided in the form of a formulation suitable for photolithography. In the photolithography process, light is used to transfer a geometric pattern from a photomask to a photocurable composition, thereby allowing the creation of a photopattern. Typically, such photocurable compositions contain a photochemically activatable polymerization initiator. For the preparation of such formulations, photoresist-based formulations known from the state of the art can be used.

[0067] 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, for example, radical polymerization, ionic polymerization, Michael addition reactions and / or cycloaddition reactions. The formulation is 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 described further below. It is further preferred that the formulation comprises an initiator for free radical polymerization or an initiator for ionic polymerization. Preferably, initiators for radical polymerization are thermally activated by exposure to heat or photochemically activated by exposure to radiation such as UV and / or visible light.

[0068] 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 peroxyacetate, tert-butyl peroxide, tert-butyl peroxybenzoate, tert-butyl peroxyisopropyl carbonate, cumene hydroperoxide, cyclohexanone peroxide, dicumyl peroxide, lauroyl peroxide, 2,4-pentanedione peroxide, peracetic acid, and potassium peroxysulfate. Typically, such initiators are radical polymerization initiators that can be thermally activated.

[0069] Further preferred initiators for radical polymerization are acetophenone, p-anisyl, 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. , 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-morpholinopropiophenone, 2-isonitrosopropiophenone, 2-phenyl-2-(p-toluenesulfonyloxy)acetophenone, and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide.

[0070] Typically such initiators are radical polymerization initiators that can be photochemically activated. Preferred initiators for ionic polymerization are alkyllithium compounds, alkylaminelithium compounds, and pentamethylcyclopentadienyls of titanium, zirconium, and hafnium (Cp * ) complex.

[0071] 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, 2-(3,4-diphenyliodonium hexafluoroarsenate ... 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 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 that can be photochemically activated.

[0072] 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 can be photochemically activated.

[0073] Exposure to radiation includes exposure to visible light and / or ultraviolet 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 or less, more preferably having a wavelength of 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. Exposure to radiation preferably includes wavelengths according to g, h, i rays and / or broadband. As a UV light source a mercury vapor lamp or a UV laser is viable, as an IR light source a ceramic emitter or an IR laser diode is viable, and for light in the visible range a laser diode is viable.

[0074] Preferred UV light sources are a) single wavelength radiation with a maximum wavelength less than 255 nm, such as, for example, 254 nm and 185 nm Hg low pressure discharge lamps, 193 nm ArF excimer lasers and 172 nm Xe2 layers, or b) sources having a broad wavelength distribution radiation with wavelength components less than 255 nm, such as, for example, non-doped mercury low pressure discharge lamps.

[0075] In a preferred embodiment of the invention, the light source is a xenon flashlight, which preferably has a broad emission spectrum with a short wavelength component down to about 200 nm.

[0076] Further provided is a dielectric polymeric material obtainable or obtainable by the above-mentioned method for forming a dielectric polymeric material according to the present invention. The polymeric material is preferably a linear or crosslinked polymer, more preferably a linear polymer. Further provided is a dielectric polymeric material comprising at least one repeat unit derived from a bismaleimide compound of any one of formulas (1), (2), (3) or (4) defined above. In a preferred embodiment, the dielectric polymer material comprises at least one repeat unit comprising a structural unit represented by one of formulas (9)-(12). [ka] In the formula, A, B, R a , R b , X, n and m have one of the definitions given above for formulas (1), (2), (3) and (4) or for the related preferred, more preferred, particularly preferred or most preferred embodiments. In a preferred embodiment, the dielectric polymeric material further contains additional repeat units derived from additional compounds capable of reacting with the bismaleimide compounds defined above.

[0077] Furthermore, there is provided an electronic device comprising a dielectric polymer material according to the invention, for 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 each other.

[0078] 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. 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.

[0079] example Synthesis of A building block [ka] 2-Adamantanone (40 mmol, 6.0 g) was added to a mixture of 25 mL of toluene and molten phenol (100 mmol, 9.4 g) at 50°C under nitrogen atmosphere and stirred until 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 maintained at 50°C for 12 hours during which time a white solid precipitated. The solid was filtered, washed with hot water and recrystallized from ethanol to give colorless needles. Yield 47%.

[0080] Analytics: 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.

[0081] [ka] tert-Butyl (7-hydroxyheptyl)carbamate (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 resulting 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.

[0082] Analytics: 1 H NMR (500 MHz, DMSO—d6): δ = 7.99 (broad 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.

[0083] Synthesis of B oligomer [ka] PriAmine™ (26 g, 49 mmol) was dissolved in 100 mL of DMAc together with triethylamine (TEA, 7.4 g, 73 mmol) and treated with isophthaloyl chloride (5 g, 24.4 mmol, dissolved in 50 mL of DMAc) at 0 °C. The reaction mixture was stirred at room temperature for 18 h, precipitated by adding 350 mL of MeOH, washed several times with MeOH, and dried under vacuum. The intermediate diamine was suspended in 200 mL of p-xylene, treated with TEA (17.3 g, 171 mmol), methanesulfonic acid (16.9 g, 176 mmol), and maleic anhydride (4.8 g, 49 mmol), and refluxed for 5 h using a Dean-Stark apparatus. After cooling to room temperature, ethanol (350 mL) was added to precipitate the product. After drying under vacuum, a brown resin was obtained (22 g, 68%).

[0084] Analytics: GPC: M n : 7.3 kDa, M w : 12.5 kDa, PDI: 1.7. 1 H NMR (500 MHz, THF—d8): δ = 8.46 (s), 8.29 (s), 7.82 (broad s), 7.29 (d, J = 7.7 Hz), 7.40 (t, J = 7.8 Hz), 6.76 (s), 3.35 (q, J = 6.6 Hz), 1.57 (dp, J = 14.5, 7.2, 6.7 Hz), 1.31 (broad s), 0.87 (dt, J = 21.2, 8.4 Hz) ppm.

[0085] [ka] PriAmine™ (10.7 g, 20 mmol) was dissolved in 50 mL DMAc together with triethylamine (TEA, 3.0 g, 30 mmol) and treated with 4,4'-oxybisbenzoyl chloride (3 g, 10 mmol, dissolved in 10 ml) at 0°C. The reaction mixture was stirred at room temperature for 18 h, precipitated by adding 200 mL MeOH, washed several times with MeOH, and dried under vacuum. The intermediate diamine was suspended in 100 mL p-xylene, treated with TEA (7.1 g, 70 mmol), methanesulfonic acid (6.9 g, 72 mmol), and maleic anhydride (2.0 g, 20 mmol), and refluxed for 5 h using a Dean-Stark apparatus. After cooling to room temperature, ethanol (150 mL) was added to precipitate the product. After drying under vacuum, a brown resin was obtained (11 g, 75%).

[0086] Analytics: GPC: M n : 5.4 kDa, M w : 13.1 kDa, PDI: 1.7. 1 H NMR (500 MHz, THF—d8): δ = 7.86 (d, J = 8.4 Hz), 7.62 (broad s), 7.00 (d, J = 7.8 Hz), 6.76 (s), 3.35 (q, J = 6.7 Hz), 1.58 (p, J = 11.1, 9.2 Hz), 1.42 ― 1.33 (m), 0.88 (q, J = 9.7, 7.9 Hz) ppm.

[0087] [ka]

[0088] Adamantane-1,3-dicarboxylic acid (Accela, 4.5 g, 20 mmol) was dissolved in NMP (80 mL) along with CaCl2 (4.9 g, 44 mmol), pyridine (12.7 g, 160 mmol) and triphenyl phosphite (15.5 g, 50 mmol). Priamine™ (21.4 g, 40 mmol) was 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, hot water and again with ethanol and dried under vacuum. The intermediate was suspended in p-xylene (100 mL) and 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, ethanol (300 mL) was added to precipitate the product, which was dried in vacuum to give a brown resin (18 g, 69%).

[0089] Analytics: GPC: M n : 4.3 kDa, M w : 8.3 kDa, PDI: 1.9. 1 H NMR (500 MHz, THF—d8): δ = 6.76 (s), 3.62 ― 3.60 (m), 3.44 (t, J = 7.2 Hz), 3.13 (q, J = 6.5 Hz), 2.08 (s), 1.88 (s), 1.79 (d, J = 8.3 Hz), 1.66 (s), 1.61 ― 1.51 (m), 1.44 (t, J = 7.0 Hz), 1.32 (s), 1.29 (s), 1.26 (s), 0.87 (dt, J = 22.2, 8.5 Hz) ppm.

[0090] [ka] Pripol™ 1009 (Croda, 7.5 g, 13.3 mmol) was dissolved in NMP (75 mL) together with CaCl2 (3.2 g, 29.2 mmol), pyridine (8.4 g, 106 mmol) and triphenyl phosphite (10.3 g, 33 mmol). Diamine (2) (14.8 g, 24 mmol) was added and the reaction mixture was stirred at 120 °C for 3 h, cooled to room temperature and precipitated by adding 400 mL of ethanol. The solid was washed several times with ethanol, hot water and again with ethanol and dried under vacuum. The intermediate was suspended in p-xylene (75 mL) and carefully mixed with methanesulfonic acid (9.2 g, 96 mmol), triethylamine (9.4 g, 93 mmol) and maleic anhydride (2.6 g, 26.6 mmol) and refluxed for 5 h using a Dean-Stark apparatus. After cooling to room temperature, ethanol (300 mL) was added to precipitate the product, which was dried in vacuum to give a brown resin (10.2 g, 43%).

[0091] Analytics: GPC: M n : 5.1 kDa, M w : 9.8 kDa, PDI: 1.9. 1 H NMR (500 MHz, THF―d8): δ = 7.26 (d, J = 8.5 Hz), 6.90 (broad s), 6.72 (s), 6.70 (d, J = 8.5 Hz), 3.83 (t, J = 6.4 Hz), 3.67 ― 3.60 (m), 3.43 (t, J = 7.1 Hz), 3.21 (s), 3.12 (q, J = 6.6 Hz), 2.07 (t, J = 10.7 Hz), 1.79 - 1.64 (m), 1.56 (dd, J = 14.3, 7.2 Hz), 1.48 - 1.38 (m), 1.38 - 1.18 (m), 0.89 (t, J = 6.6 Hz) ppm.

[0092] [ka] Pripol™ 1009 (Croda, 10 g, 17.7 mmol) was dissolved in NMP (100 mL) along with CaCl2 (4.3 g, 38.9 mmol), pyridine (11.2 g, 141 mmol) and triphenyl phosphite (13.7 g, 44 mmol). The reaction mixture was stirred at 120 °C for 5 h, cooled to room temperature and precipitated by adding 400 mL of acetonitrile. The solid was washed several times with acetonitrile, hot water and again with acetonitrile and dried under vacuum. The intermediate was suspended in p-xylene (75 mL) and carefully mixed with methanesulfonic acid (12.2 g, 127 mmol), triethylamine (12.5 g, 124 mmol) and maleic anhydride (3.4 g, 35 mmol) and refluxed for 5 h using a Dean-Stark apparatus. After cooling to room temperature, acetonitrile (300 mL) was added to precipitate the product. After drying under vacuum, an amber resin was obtained (13 g, 67%).

[0093] Analytics: GPC: M n : 3.8 kDa, M w : 7.0 kDa, PDI: 1.8. 1 H NMR (500 MHz, THF―d8): δ = 6.77 (s), 3.07 ― 2.92 (m), 2.47 ― 2.35 (m), 2.21 ― 2.04 (m), 2.01 ― 1.85 (m), 1.69 ― 1.54 (m), 1.40 (d, J = 17.6 Hz), 1.29 (s), 1.16 (s), 0.88 (dt, J = 11.3, 6.2 Hz) ppm.

[0094] [ka] Octadecadienoic acid dipolymer (BocSciences, CAS: 61788-89-4, 5 g, 9.6 mmol) was dissolved in NMP (75 mL) together with CaCl2 (2.3 g, 21 mmol), pyridine (6 g, 76.5 mmol) and triphenyl phosphite (7.4 g, 23.9 mmol). Diamine (2) (10.7 g, 17 mmol) was added and the reaction mixture was stirred at 120 °C for 5 h, cooled to room temperature and precipitated by adding 400 mL of acetonitrile. The solid was washed several times with acetonitrile, hot water and again with acetonitrile and dried under vacuum. The intermediate was suspended in p-xylene (50 mL) and carefully mixed with methanesulfonic acid (6.6 g, 69 mmol), triethylamine (6.8 g, 67 mmol) and maleic anhydride (1.9 g, 19 mmol) and refluxed for 5 h using a Dean-Stark apparatus. After cooling to room temperature, acetonitrile (300 mL) was added to precipitate the product, which was dried in vacuum to give a yellow resin (11 g, 70%).

[0095] Analytics: GPC: M n : 3.8 kDa, M w : 7.2 kDa, PDI: 1.9. 1 H NMR (500 MHz, THF—d8): δ = 7.26 (d, J = 8.5 Hz), 6.72 (s), 6.70 (d, J = 8.7 Hz), 3.83 (t, J = 6.3 Hz), 3.64 ― 3.59 (m), 3.43 (t, J = 7.1 Hz) 3.21 (s), 3.13 (q, J = 6.6 Hz), 2.08 (d, J = 12.7 Hz), 1.78 - 1.74 (m), 1.73 - 1.66 (m), 1.62 - 1.52 (m), 1.43 (d, J = 12.9 Hz), 1.38 - 1.23 (m), 0.95 - 0.84 (m) ppm.

[0096] [ka] Pripol™ 1009 (Croda, 10 g, 17.7 mmol) was dissolved in NMP (100 mL) together with CaCl2 (4.3 g, 38.9 mmol), pyridine (11.2 g, 142 mmol) and triphenyl phosphite (13.7 g, 44 mmol). Diamine (2) (hydrobromide salt, 11.3 g, 15.9 mmol) and bis(aminomethyl)tricyclo[5.2.1.0]decane (J&K Scientific GmbH, CAS: 76364-76-6, 3.1 g, 15.9 mmol) were added successively 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, hot water and again with ethanol and dried in vacuum. The intermediate was suspended in p-xylene (100 mL), carefully mixed with methanesulfonic acid (12.2 g, 127 mmol), triethylamine (12.5 g, 124 mmol) and maleic anhydride (3.5 g, 35.4 mmol) and refluxed for 5 h using a Dean-Stark apparatus. After cooling to room temperature, ethanol (400 mL) was added to precipitate the product. After drying in vacuum, a yellow resin was obtained (15.2 g, 65%).

[0097] Analytics: GPC: M n : 4.8 kDa, M w : 8.7 kDa, PDI: 1.8. 1 H NMR (500 MHz, THF—d8): δ = 7.26 (d, J = 8.5 Hz), 6.72 (s), 6.70 (d, J = 8.5 Hz), 3.83 (t, J = 6.3 Hz), 3.43 (t, J = 7.1 Hz), 3.21 (s), 3.12 (q, J = 6.6 Hz), 3.06 ― 2.88 (m), 2.62 ― 2.49 (m), 2.47 ― 2.31 (m), 2.06 (q, J = 9.7, 7.1 Hz), 1.81 ― 1.64 (m), 1.62 ― 1.48 (m), 1.47 ― 1.38 (m), 1.31 (d, J = 16.6 Hz), 0.88 (q, J = 8.1, 7.1 Hz) ppm.

[0098] Mechanical Test Dynamic Mechanical Analysis Free-standing films were prepared as follows: A concentrated solution of the oligomer in cyclopentanone is mixed with photoinitiator and structural additives and slit-coated onto a glass substrate. The resulting film is first dried at room temperature and then dried on a hotplate at 100 °C for 30 min. The film is cured by broadband UV exposure (UVACUBE 2000, Honle, mercury lamp, dose: 10 J / cm2) and finally removed from the substrate after immersion in water. The free-standing film is dried in air for 20 h. Dynamic mechanical analysis (DMA) was performed using a Netzsch DMA 242 E instrument with a heating rate of 3 K / min in air.

[0099] DMA:Result (1) Oligomer (3) is cured with 5 wt.-% of Irgacure OXE-02. See Figure 2: Tg(tan δ): 47.8°C. (2) The oligomer (3) is cured with 10 wt.-% bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS RN: 105391-33-1, TCI) as a structural additive and 5 phr of Irgacure OXE-02. See Figure 3: Tg(tan δ): 53.3°C. (3) Oligomer (3) is cured with 10 wt. % pentaerythritol tetraacrylate (CAS RN: 4986-89-4, Sigma-Aldrich (Merck)) as a structural additive and 5 phr of Irgacure OXE-02. See Figure 4: Tg (tan δ): 53.3°C. (4) Oligomer (4) is cured with 5 wt% of Irgacure OXE-02. See Figure 5: Tg(tan δ): 60.2°C. (5) Oligomer (4) is cured with 10 wt.-% bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS RN: 105391-33-1, TCI) as a structural additive and 5 phr Irgacure OXE-02. See Figure 6: Tg(tan δ): 68.2°C. (6) Oligomer (5) is cured with 5 wt% Irgacure OXE-02. See Figure 7: Tg(tan δ): 48.8°C. (7) Oligomer (5) is cured with 10 wt.-% bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS RN: 105391-33-1, TCI) as a structural additive and 5 phr Irgacure OXE-02. See Figure 8: Tg(tan δ): 50.1°C. (8) Oligomer (6) is cured with 5 wt% Irgacure OXE-02. See Figure 9: Tg(tan δ): 67.8°C. (9) Oligomer (6) is cured with 20 wt. % tetra(ethylene glycol) diacrylate (CAS RN: 17831-71-9, Merck Sigma-Aldrich) and 5 phr Irgacure OXE-02 as structural additives. See Figure 10: Tg(tan δ): 67.1°C. (10) Oligomer (7) is cured with 5 wt% Irgacure OXE-02. See Figure 11: Tg(tan δ): 74.9°C. (11) Oligomer (7) is cured with 30 wt. % tetra(ethylene glycol) diacrylate (CAS RN: 17831-71-9, Merck Sigma-Aldrich) and 5 phr Irgacure OXE-02 as structural additives. See Figure 12: Tg(tan δ): 72.1°C. (12) Oligomer (8) is cured with 5 wt% Irgacure OXE-02. See Figure 13: Tg(tan δ): 77.0°C. (13) Oligomer (9) is cured with 5 wt% Irgacure OXE-02. See Figure 14: Tg(tan δ): 74.2°C. (14) Oligomer (9) is cured with 10 wt.-% bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS RN: 105391-33-1, TCI) as a structural additive and 5 phr Irgacure OXE-02. See Figure 15: Tg(tan δ): 80.8°C. (15) Reference material BMI3000 (commercial grade, Designer Molecules Inc.) BMI3000 is cured with 5 wt% Irgacure OXE-02. See Figure 16: Tg(tan δ): 43.5°C.

[0100] Young's modulus and elongation at break Young's modulus and elongation at break were measured on a mechanical testing machine (500 NZwicki) using the following parameters: Pre-measurement: 0.1 N at an elongation rate of 10 mm / min; Main elongation rate 50 mm / min. All experiments were carried out at room temperature using free-standing films prepared by the method described above. The film dimensions were 25 mm in length and 15 mm in width, with typical film thicknesses ranging from 40 to 60 μm.

[0101] result: [Table 1] DConclusion Direct comparison of prior art imide-extended bismaleimide resins, such as Designer Molecules Inc.’s BMI3000 (commercial grade), with the closely related amide-based bismaleimide oligomer (3) surprisingly showed improved mechanical properties for the amide derivative. The glass transition temperature increases. A further unexpected effect is that the polymer networks formed with oligomer (3) are characterized by higher flexibility, as shown by an almost doubling of the elongation at break. The specific resin design allows the material properties to be tailored in different directions, making this class of materials highly suitable for the development of advanced packaging solutions.

Claims

1. Formulas (1) to (4) 【Chemistry 1】 During the ceremony, A and B are, independently and at each occurrence independently of one another, a linking unit comprising one or more aliphatic, aromatic, or siloxane moieties, where optionally A, B, or A and B contain a cardo or spiro center; R ａ and R ｂ are, independently and at each occurrence independently of each other, a linking unit that contains one or more aliphatic, aromatic, or siloxane moieties; R ｃ is R ａ Or R ｂ and X is, independently of each other, an amide 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; n is an integer from 1 to 60, and m is an integer from 1 to 60 The bismaleimide compound is represented by any one of the following formulas:

2. A, at each occurrence, independently of one another, is a linking unit containing one or more cycloaliphatic moieties, which may optionally be bridged, or aromatic moieties, where A optionally contains a cardo or spiro center; and 2. The bismaleimide compound of claim 1, wherein B at each occurrence is independently one or more cycloaliphatic moieties, which may be optionally bridged, or a linking unit comprising an aromatic moiety, and wherein B optionally contains a cardo center or a spiro center.

3. 2. The bismaleimide compound of claim 1, wherein A and B are, independently and at each occurrence independently of one another, a substituted or unsubstituted aliphatic moiety having from 2 to 100 carbon atoms, a substituted or unsubstituted hydrocarbon aromatic moiety having from 6 to 100 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having from 4 to 100 carbon atoms, a substituted or unsubstituted siloxane moiety having from 2 to 50 silicon atoms, or combinations thereof, wherein optionally A, B, or A and B contain a cardo center or a spiro center.

4. A are, independently of each other occurrence, a substituted or unsubstituted cycloaliphatic moiety having 3 to 80 carbon atoms, which may be optionally bridged, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 80 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 80 carbon atoms, or a combination thereof, where A optionally contains a cardo or spiro center; and 2. The bismaleimide compound of claim 1, wherein B is, at each occurrence, independently of each other, a substituted or unsubstituted cycloaliphatic moiety having 3 to 80 carbon atoms, which may be optionally bridged, a substituted or unsubstituted hydrocarbon aromatic moiety having 6 to 80 carbon atoms, a substituted or unsubstituted heteroaromatic moiety having 4 to 80 carbon atoms, or a combination thereof, where B optionally contains a cardo center or a spiro center.

5. Each occurrence of A is independently represented by formula (5): 【Chemistry 2】 During the ceremony A ２１ , A ２２ and A ２３ are independently and independently of each other at each occurrence a divalent aromatic group, a divalent aliphatic group, or a divalent mixed aromatic aliphatic group, 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 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, aryl having 6 to 10 carbon atoms and aryloxy having 6 to 10 carbon atoms, wherein one or more A ２１ , A ２２ and A ２３ optionally containing a cardo or spiro center, G ２１ , G ２２ , G ２３ and G ２４ are independently and independently of each other at each occurrence -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 = C.Y. 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; Y ０１ and Y ０２ are each independently H, an alkyl having 1 to 5 carbon atoms, phenyl, F, Cl, or CN, and 2. The bismaleimide compound according to claim 1, wherein k and l are each independently 0, 1, 2, 3 or 4.

6. A ２１ , A ２２ and A ２３ are independently and independently of each other at each occurrence represented by any one of formulas (5a) to (5x), 【Chemistry 3-1】 【Chemistry 3-2】 【Chemistry 3-3】 During the ceremony 【Chemistry 4】 represents the binding site, L is an alkyl having 1 to 5 carbon atoms, halogenyl, Ph or CN; R Ａｌｋ is alkyl having 1 to 5 carbon atoms; Q is O, S or CH ２ and z is an integer from 1 to 20, and 2. The bismaleimide compound according to claim 1, wherein q is an integer from 0 to 4.

7. B is represented by any one of formulas (6a) to (6d) independently at each occurrence; 【Chemistry 5】 During the ceremony 【Chemistry 6】 represents the binding site, L is, independently of each other at each occurrence, an alkyl having 1 to 5 carbon atoms, halogenyl, Ph or CN; q is an integer from 0 to 4, and 2. The bismaleimide compound according to claim 1, wherein v is an integer from 0 to 12.

8. R ａ and R ｂ are independently and independently of each other at 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; and R ｃ is R ａ Or R ｂ The bismaleimide compound according to claim 1 ,

9. R ａ and R ｂ are independently and independently of each other at each occurrence a substituted or unsubstituted aliphatic moiety having 2 to 100 carbon atoms, which optionally contains one or more C═C double bonds, C≡C triple bonds or amide groups; and R ｃ is R ａ Or R ｂ The bismaleimide compound according to claim 1 ,

10. R ａ and R ｂ are independently and independently of each other at each occurrence represented by any one of formulas (7a) to (7d), 【Chemistry 7-1】 【Chemistry 7-2】 During the ceremony 【Chemistry 8】 represents the binding site; x and y are each independently an integer from 0 to 12; and R Ｉ and R ＩＩ are each independently a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 3 to 12 carbon atoms, a linear alkylene group having 2 to 12 carbon atoms, or a branched alkylene group having 3 to 12 carbon atoms.

11. R ａ and R ｂ are independently and independently of each other at each occurrence represented by any one of formulas (8a) to (8d), 【Chemistry 9-1】 【Chemistry 9-2】 During the ceremony 【Chemistry 10】 The bismaleimide compound according to claim 1 , wherein

12. X is independently each occurrence -(CO)-NR ３ --or-- ３ -(CO)-, where R ３ is H or alkyl having 1 to 5 carbon atoms.

13. below (i) providing a formulation comprising one or more bismaleimide compounds according to any one of claims 1 to 12, and (ii) Curing the formulation A method for forming a dielectric polymer material comprising the steps of:

14. 14. The method for forming a dielectric polymer material of claim 13, wherein the formulation further comprises one or more additional compounds capable of reacting with the bismaleimide compound.

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

16. A dielectric polymer material obtainable by the method according to claim 13.

17. A dielectric polymer material comprising at least one repeat unit derived from a bismaleimide compound as defined in any one of claims 1 to 12.

18. The repeating unit contains a structural unit represented by one of formulas (9) to (12): 【Chemistry 11】 In the formula, A, B, R ａ , R ｂ , X, n and m are as defined in any one of claims 1 to 12.

20. The dielectric polymer material of claim 17.

19. 20. An electronic device comprising the dielectric polymer material of claim 16.

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

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

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