Resin composition for non-conductive film with excellent high temperature properties for 3D TSV packaging

Abstract

The present disclosure relates to compositions for forming films and the use of said films in three-dimensional through silicon via (3D TSV) packages. In certain aspects, the present disclosure relates to compositions comprising one or more resins, one or more imidazoles with latent thermal activity, one or more inorganic fillers, and one or more additives, B-stage films prepared from the compositions of the present disclosure, and cured films obtained after curing the compositions of the present disclosure.

Description

[Technical field]

[0001] Aspects of the present disclosure relate to compositions for forming films and the use of said films in three-dimensional through silicon via (3D TSV) packages. In certain aspects, the present disclosure relates to compositions comprising one or more resins, one or more imidazoles with latent thermal activity, one or more inorganic fillers, and one or more additives, B-stage films prepared from the compositions of the present disclosure, and cured films obtained after curing of the compositions of the present disclosure. In certain aspects, the cured films obtained after curing of the compositions of the present disclosure have specific physical properties and / or combinations of physical properties. In certain aspects, the present disclosure relates to underfill films prepared from the compositions of the present disclosure, such as wafer level underfill films (WAUF). Film embodiments of the present disclosure are suitable for use in, for example, thermocompression bonding methods. [Background technology]

[0002] As we look towards the next generation of high performance 3D TSV packages, the materials industry is faced with the need to improve the high temperature properties of film materials (such as underfill film materials). Achieving this goal could bring benefits such as improved thermal stability and therefore improved reliability in applications across the automotive, computing, networking, and communications industries. Features that may be associated with improved high temperature properties of film materials include a relatively high Tg (glass transition temperature), a relatively low CTE (coefficient of thermal expansion), and a relatively high modulus of elasticity, for example at 250°C.

[0003] Problems have arisen when films prepared from certain conventional resin compositions containing maleimide-containing resins are used in thermocompression bonding processes. For example, in some cases, B-stage films prepared from certain conventional resin compositions containing maleimide-containing resins may have a DSC onset temperature of less than 100°C to 150°C. When such B-stage films are used in thermocompression bonding processes in which the bond head contact temperature is between 100°C and 150°C (e.g., when such processes have a bond head contact temperature between 130°C and 210°C), problems with material entrapment may occur during solder bonding. In other examples, B-stage films prepared from conventional resin compositions containing maleimide-containing resins may have a DSC onset temperature higher than the melting temperature of the solder (e.g., lead-free solder), e.g., a DSC onset temperature higher than 217°C. When such B-stage films are used in thermocompression bonding processes, problems with solder extrusion may occur in some cases. In some cases, solder extrusion problems can also occur when B-staged films prepared from conventional resin compositions that include one or more maleimide-containing resins have a ΔT from the DSC onset temperature to the DSC peak temperature that is greater than 20° C., such as about 40° C. Summary of the Invention [Problem to be solved by the invention]

[0004] In light of at least the considerations discussed above, there is interest in compositions comprising one or more resins, one or more inorganic fillers, and one or more additives, B-stage films prepared from said compositions, and cured films obtained after curing of said compositions, wherein said compositions include one or more imidazoles having latent thermal activity. As used herein, a latent thermally active imidazole is an imidazole having a latent thermal activity of 0.20 g when combined with 1.0 g of NC-3000-L epoxy resin (Nippon Kayaku). 2refers to an imidazole that produces a composition that exhibits a DSC onset temperature of at least 145° C. and a DSC peak temperature of at least 150° C. when measured in a TA Instruments DSC Q20 thermal analyzer at a ramp rate of 10° C. / min from room temperature to 300° C. For example, in some embodiments, a potentially thermally active imidazole exhibits a DSC onset temperature of at least 145° C., at least 150° C., at least 155° C., at least 160° C., at least 165° C., at least 170° C., at least 175° C., or at least 180° C. when analyzed as just described. For example, in some embodiments, the potentially thermally active imidazole, when analyzed as just described, exhibits a DSC onset temperature of 145° C. to 180° C., e.g., 145° C. to 175° C., 145° C. to 170° C., 145° C. to 160° C., 150° C. to 180° C., 150° C. to 175° C., 150° C. to 170° C., 150° C. to 160° C., 155° C. to 175° C., 155° C. to 170° C., or 155° C. to 165° C. In some embodiments, the potentially thermally active imidazole, when analyzed as just described, exhibits a DSC peak temperature of at least 150° C., at least 155° C., at least 160° C., at least 165° C., at least 170° C., at least 175° C., or at least 185° C. For example, in some embodiments, the potentially thermally active imidazole, when analyzed as just described, exhibits a DSC peak temperature of from 150°C to 185°C, e.g., from 150°C to 180°C, from 150°C to 175°C, from 150°C to 170°C, from 150°C to 165°C, from 150°C to 160°C, from 160°C to 180°C, from 165°C to 175°C, or from 160°C to 170°C.

[0005] For the avoidance of doubt, it is to be understood that the DSC onset temperature and / or DSC peak temperature exhibited by a composition prepared and measured as described (i.e., a composition comprising 0.20 g of potentially thermally active imidazole and 1.0 g of NC-3000-L epoxy resin (Nippon Kayaku)) may be the same as or different from the DSC onset temperature and / or DSC peak temperature exhibited by a composition comprising the same potentially thermally active imidazole but containing other components such as one or more resins, or more inorganic fillers, and / or one or more additives.

[0006] In some embodiments, the potentially thermally active imidazole comprises at least two electron-withdrawing groups.

[0007] In comparison, imidazoles that do not constitute potential thermally active imidazoles include N 2 and imidazoles which result in compositions which exhibit a DSC onset temperature of less than 145° C. and a DSC peak temperature of less than 150° C. when measured in a TA Instruments DSC Q20 thermal analyzer at a ramp rate of 10° C. / min from room temperature to 300° C.

[0008] As a non-limiting example, four imidazoles were analyzed as above. Specifically, four separate experiments were performed. In each experiment, 0.20 g of either Imidazole A, Imidazole B, Imidazole C, or Imidazole D was mixed with 1.0 g of NC-3000-L epoxy resin (Nippon Kayaku Co., Ltd.), and the resulting composition was subjected to 1000 mL of NC-3000-L epoxy resin (Nippon Kayaku Co., Ltd.) for 1 h. 2 The measurements were performed on a TA Instruments Thermal Analyzer DSC Q20 in a 10°C / min ramp rate from room temperature to 300°C. The DSC onset temperature and DSC peak temperature were measured. The results are shown in the table below. Imidazole A is 4-methyl-2-phenyl-1H-imidazole-5-methanol. Imidazole B is 2-phenyl-4,5-dihydroxymethylimidazole. Imidazole C is 2-phenylimidazole. Imidazole D is 2-ethyl-4-methyl-1H-imidazole-1-propanenitrile.

[0009] [Table 1]

[0010] 1 Test conditions: 0.20 g of each imidazole was mixed with 1.0 g of NC-3000-L epoxy resin (Nippon Kayaku), and each of the resulting compositions was 2The samples were analyzed using a TA Instruments thermal analyzer DSC Q20 at a ramp rate of 10°C / min from room temperature to 300°C.

[0011] Imidazole A and Imidazole B are exemplary potentially thermally active imidazoles, while Imidazole C and Imidazole D are not considered potentially thermally active imidazoles within the context of this disclosure. As shown above, when analyzed as described above, compositions containing Imidazole A or Imidazole B, respectively, exhibited a DSC onset temperature of at least 145° C. and a DSC peak temperature of at least 150° C., whereas compositions containing Imidazole C or Imidazole D, respectively, exhibited a DSC onset temperature of less than 145° C. and a DSC peak temperature of less than 150° C.

[0012] The embodiments of the compositions of the present disclosure address the problems discussed above. For example, the embodiments of the underfill films prepared from the compositions of the present disclosure are suitable for thermocompression bonding methods, such as thermocompression bonding methods for 3D TSV stacking applications. Furthermore, the embodiments of the underfill films prepared from the compositions of the present disclosure exhibit one or more of good die corner coverage, gap filling, and electrical interconnect bond formation.

[0013] In some embodiments, aspects of the present disclosure are directed to the following: 1. one or more resins selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins; one or more imidazoles having potential thermal activity, one or more inorganic fillers, and one or more additives selected from the group consisting of adhesion promoters and film formers; A composition comprising: After the composition forms a film, the film has the following physical properties: Tg>200°C as measured by dynamic mechanical analysis (DMA); Storage modulus at 25℃ < 6.5GPa, Storage modulus at 250°C > 0.1 GPa, and Coefficient of Thermal Expansion (CTE) <250ppm / ℃.

[0014] 2. The composition of embodiment 1, wherein the latent active imidazole is an imidazole containing at least two electron-withdrawing groups.

[0015] 3. The composition of any of the preceding embodiments, wherein said imidazole comprises at least two electron-withdrawing groups independently selected from hydroxymethyl and phenyl.

[0016] 4. The imidazole is

[0017] [ka]

[0018] (In the formula, R 1 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R 2 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R 3 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R 4 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl. The composition of any of the preceding embodiments, wherein provided that the imidazole contains at least two electron-withdrawing groups.

[0019] 5. The maleimide-containing resin

[0020] [ka]

[0021] (In the formula, Each R is independently selected from the group consisting of H and substituted or unsubstituted alkyl; each m is independently selected from the group consisting of 0, 1, 2, 3, or 4; n is 0, 1, 2, 3, 4 or 5. A compound represented by the formula: or

[0022] [ka]

[0023] (wherein n is 0, 1, 2, 3, 4 or 5). The compound represented by the formula: The composition of any of the preceding embodiments.

[0024] 6. The (meth)acrylic resin is

[0025] [ka]

[0026] (wherein n is 0, 1, 2, 3, 4 or 5). The composition of any of the preceding embodiments, wherein

[0027] 7. The epoxy resin is

[0028] [ka]

[0029] (In the formula, n is 0, 1, 2, 3, 4 or 5, and m is 0, 1, 2, 3, 4 or 5.) The composition of any of the preceding embodiments, wherein the compound is represented by:

[0030] 8. After the composition forms a film, the film has the following physical properties: Differential scanning calorimetry (DSC) onset temperatures between 130°C and 250°C, as measured by DSC at a ramp rate of 10°C / min, and Use a DHR2 rheometer at a ramp rate of 10 °C / min. 2 The minimum film melt viscosity measured in the range of 10 Pa·s to 10,000 Pa·s, The composition of any of the preceding embodiments, having

[0031] 9. The composition of any of the preceding embodiments, wherein after the composition forms a film, the ΔT from the DSC onset temperature to the DSC peak temperature of the film is less than 20° C. or less than 15° C.

[0032] 10. Preparing the composition of any of the preceding embodiments; casting the composition into a film; exposing the cast film to an elevated temperature to cure the film; A method for preparing a cured film comprising:

[0033] 11. One or more resins selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins; one or more imidazoles having potential thermal activity, one or more inorganic fillers, and one or more additives selected from the group consisting of adhesion promoters and film formers; preparing a composition comprising: casting the composition into a film; exposing the cast film to an elevated temperature to cure the film; A method for preparing a cured film comprising:

[0034] 12. The method of embodiment 11, wherein said potentially thermally active one or more imidazoles are one or more imidazoles comprising at least two electron-withdrawing groups.

[0035] 13. A cured film prepared according to the method of embodiment 11 or embodiment 12.

[0036] 14. A film prepared according to the method of any of embodiments 11-13, the film having the following physical properties: Tg>200°C as measured by dynamic mechanical analysis (DMA); Storage modulus at 25℃ < 6.5GPa, Storage modulus at 250°C > 0.1 GPa, and Coefficient of Thermal Expansion (CTE) <250ppm / ℃.

[0037] 15. The film of embodiment 13 or embodiment 14, wherein the film is an underfill film. [Brief description of the drawings]

[0038] [Figure 1] FIG. 1 shows DSC (differential scanning calorimetry) data for an exemplary composition of the present disclosure (Example 3). [Diagram 2] FIG. 2 shows melt viscosity data for an exemplary composition of the present disclosure (Example 3). [Diagram 3] FIG. 3 shows DMA (Dynamic Mechanical Analysis) data for an exemplary composition of the present disclosure (Example 3). [Figure 4] FIG. 4 shows TMA (thermo-mechanical analysis) data for an exemplary composition of the present disclosure (Example 3). [Diagram 5] FIG. 5 shows DSC (differential scanning calorimetry) data for an exemplary composition of the present disclosure (Example 8). [Figure 6] FIG. 6 shows melt viscosity data for an exemplary composition of the present disclosure (Example 8). [Figure 7] FIG. 7 shows DMA (Dynamic Mechanical Analysis) data for an exemplary composition of the present disclosure (Example 8). [Figure 8] FIG. 8 shows TMA (thermo-mechanical analysis) data for an exemplary composition of the present disclosure (Example 8). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0039] The compositions and methods of the present disclosure may be more readily understood by reference to the following detailed description in conjunction with the accompanying drawings, which form a part of this disclosure.

[0040] According to the present disclosure, there is provided a composition comprising one or more resins, one or more imidazoles with latent thermal activity, one or more inorganic fillers, and one or more additives. In some embodiments, the one or more resins are selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins. In some embodiments, the one or more additives are selected from the group consisting of adhesion promoters and film formers. In some embodiments, the one or more imidazoles with latent thermal activity are one or more imidazoles containing at least two electron-withdrawing groups.

[0041] In some embodiments, after the composition forms a film, the film has certain characteristics and / or properties that make the film suitable for use in a thermocompression process. For example, in some embodiments, after the composition forms a film, the film has a Tg>100° C., a storage modulus at 25° C.<4 GPa, a storage modulus at 250° C.>0.1 GPa, and a coefficient of thermal expansion (CTE)<250 ppm / ° C. as measured by dynamic mechanical analysis (DMA). In some embodiments, after the composition forms a B-stage film, the B-stage film has a Differential Scanning Calorimetry (DSC) onset temperature of 130° C. to 250° C. as measured by DSC at a ramp rate of 10° C. / min, and a N-stage using a DHR2 rheometer at a ramp rate of 10° C. / min. 2It has a minimum film melt viscosity of 10 Pa·s to 10,000 Pa·s when measured in

[0042] In some embodiments, after the composition forms a cured film, the cured film has a Tg of >100°C, >125°C, >150°C, >160°C, >165°C, >170°C, >175°C, >180°C, >185°C, >190°C, >200°C, >210°C, >220°C, >230°C, >240°C, >250°C, >260°C, >270°C, >280°C, >290°C, or >300°C as measured by dynamic mechanical analysis (DMA). In some embodiments, after the composition forms a cured film, the cured film has a Tg of 100°C to 110°C, 110°C to 120°C, 120°C to 130°C, 130°C to 140°C, 140°C to 150°C, 150°C to 160°C, 160°C to 170°C, 170°C to 180°C, 180°C to 190°C, 190°C to 200°C, 200°C to 210°C, 210°C to 220°C, 220°C to 230°C, 230°C to 240°C, 240°C to 250°C, 250°C to 260°C, 260°C to 270°C, 270°C to 280°C, 280°C to 290°C, or 290°C to 300°C, as measured by DMA.

[0043] In some embodiments, after the composition forms a cured film, the cured film has a Tg of >100°C, >125°C, >150°C, >160°C, >165°C, >170°C, >175°C, >180°C, >185°C, >190°C, >200°C, >210°C, >220°C, >230°C, >240°C, or >250°C as measured by thermomechanical analysis (TMA). In some embodiments, after the composition forms a cured film, the cured film has a Tg of 100° C. to 110° C., 110° C. to 120° C., 120° C. to 130° C., 130° C. to 140° C., 140° C. to 150° C., 150° C. to 160° C., 160° C. to 170° C., 170° C. to 180° C., 180° C. to 190° C., 190° C. to 200° C., 200° C. to 210° C., 210° C. to 220° C., 220° C. to 230° C., 230° C. to 240° C., or 240° C. to 250° C., as measured by TMA. In some embodiments, after the composition forms a cured film, the cured film has a Tg of 140° C. to 200° C., for example, 150° C. to 190° C., 160° C. to 190° C., or 160° C. to 180° C.

[0044] In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 25° C. of <3 GPa, <3.5 GPa, <4 GPa, <4.5 GPa, <5 GPa, <5.5 GPa, <6 GPa, or <6.5 GPa.

[0045] In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 25° C. of 2.0 GPa to 3.0 GPa, 3.0 GPa to 3.5 GPa, 3.5 GPa to 4.0 GPa, 4.0 GPa to 4.5 GPa, 4.5 GPa to 5.0 GPa, 5.0 GPa to 5.5 GPa, 5.5 GPa to 6.0 GPa, or 6.0 GPa to 6.5 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 25° C. of 3.0 GPa to 6.5 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 25° C. of 3.5 GPa to 6.0 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 25° C. of 4.0 GPa to 5.5 GPa.

[0046] In some embodiments, after the composition forms a B-staged film, the B-staged film has a storage modulus at 250° C. of >0.1 GPa, >0.2 GPa, >0.3 GPa, >0.4 GPa, >0.5 GPa, >0.6 GPa, >0.7 GPa, >0.8 GPa, >0.9 GPa, >1.0 GPa, or >1.1 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 250° C. of 0.1 GPa to 0.2 GPa, 0.2 GPa to 0.3 GPa, 0.3 GPa to 0.4 GPa, 0.4 GPa to 0.5 GPa, 0.5 GPa to 0.6 GPa, 0.6 GPa to 0.7 GPa, 0.7 GPa to 0.8 GPa, 0.8 GPa to 0.9 GPa, 0.9 GPa to 1.0 GPa, or 1.0 GPa to 1.1 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 250° C. of 0.4 GPa to 1.2 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 250° C. of 0.5 GPa to 1.2 GPa.

[0047] In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 230° C. of >0.1 GPa, >0.2 GPa, >0.3 GPa, or >0.4 GPa, >0.5 GPa, >0.6 GPa, >0.7 GPa, >0.8 GPa, >0.9 GPa, >1.0 GPa, >1.1 GPa, or >1.2 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 230° C. of 0.1 GPa to 0.2 GPa, 0.2 GPa to 0.3 GPa, 0.3 GPa to 0.4 GPa, 0.4 GPa to 0.5 GPa, 0.5 GPa to 0.6 GPa, 0.6 GPa to 0.7 GPa, 0.7 GPa to 0.8 GPa, 0.8 GPa to 0.9 GPa, 0.9 GPa to 1.0 GPa, 1.0 GPa to 1.1 GPa, or 1.1 GPa to 1.2 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 230° C. of 0.5 GPa to 1.2 GPa. In some embodiments, after the composition forms a B-stage film, the B-stage film has a storage modulus at 230° C. of 0.6 GPa to 1.2 GPa.

[0048] In some embodiments, after the composition forms a cured film, the cured film has a coefficient of thermal expansion (CTE) of <60 ppm / ° C., <70 ppm / ° C., <80 ppm / ° C., <90 ppm / ° C., <100 ppm / ° C., <110 ppm / ° C., <120 ppm / ° C., <130 ppm / ° C., <140 ppm / ° C., <150 ppm / ° C., <160 ppm / ° C., <170 ppm / ° C., <180 ppm / ° C., <190 ppm / ° C., <200 ppm / ° C., <210 ppm / ° C., <220 ppm / ° C., <230 ppm / ° C., <240 ppm / ° C., or <250 ppm / ° C.

[0049] In some embodiments, after the composition forms a cured film, the cured film has a coefficient of thermal expansion (CTE) above Tg of <100 ppm / °C, <110 ppm / °C, <120 ppm / °C, <130 ppm / °C, <140 ppm / °C, <150 ppm / °C, <160 ppm / °C, <170 ppm / °C, <180 ppm / °C, <190 ppm / °C, <200 ppm / °C, <210 ppm / °C, <220 ppm / °C, <230 ppm / °C, <240 ppm / °C, or <250 ppm / °C. In some embodiments, after the composition forms a cured film, the cured film has a coefficient of thermal expansion (CTE) above Tg of 50 ppm / °C to 80 ppm / °C. In some embodiments, after the composition forms a cured film, the cured film has a coefficient of thermal expansion (CTE) above Tg of 60 ppm / ° C. to 80 ppm / ° C. In some embodiments, after the composition forms a cured film, the cured film has a coefficient of thermal expansion (CTE) above Tg of 60 ppm / ° C. to 70 ppm / ° C.

[0050] In some embodiments, after the composition forms a B-stage film, the B-stage film is subjected to a N 2 In some embodiments, after the composition forms a B-stage film, the B-stage film is rheometered at 100° C. / min using a DHR2 rheometer at a ramp rate of 10° C. / min to 5,000 Pa s. 2 In some embodiments, after the composition forms a B-stage film, the B-stage film is rheologically stable at 100° C. / min using a DHR2 rheometer at a ramp rate of 10° C. / min and has a minimum film melt viscosity of 900 Pa·s to 6,500 Pa·s. 2 In some embodiments, after the composition forms a B-stage film, the B-stage film is rheologically stable at 10° C. / min using a DHR2 rheometer at a ramp rate of 10° C. / min and has a minimum film melt viscosity of 2,000 Pa·s to 6,000 Pa·s. 2In some embodiments, after the composition forms a B-stage film, the B-stage film is rheometered at 2,000 Pa·s to 4,000 Pa·s using a DHR2 rheometer at a ramp rate of 10° C. / min. 2 It has a minimum film melt viscosity of 4,000 Pa·s to 6,000 Pa·s, measured in 3000°C.

[0051] In some embodiments, after the composition forms a B-stage film, the B-stage film is subjected to a N 2Measured within the range of 500 Pa·s to 600 Pa·s, 600 Pa·s to 700 Pa·s, 700 Pa·s to 800 Pa·s, 800 Pa·s to 900 Pa·s, 900 Pa·s to 1,000 Pa·s, 1,000 Pa·s to 1,100 Pa·s, 1,100 Pa·s to 1,200 Pa·s, 1,200 Pa·s to 1,300 Pa·s, 1,300 Pa·s to 1,400 Pa·s, 1,400 Pa·s to 1,500 Pa·s, 1,500 Pa·s to 1,600 Pa·s, 1,600 Pa·s to 1,700 Pa·s, 1,700 Pa·s to 1,800 Pa·s, 1,800 Pa·s to 1,900 Pa·s, 1,900 Pa·s to 2,000 Pa·s, 2,000 Pa·s to 2,100 Pa·s, 2,100 Pa·s to 2,200 Pa·s, 2,200 Pa·s to 2,300 Pa·s, 2,300 Pa·s to 2,400 Pa·s, 2,400 Pa·s to 2,500 Pa·s, 2,500 Pa·s to 2,600 Pa·s, 2,600 Pa·s to 2,700 Pa·s, 2,700 Pa·s to 2,800 Pa·s, 2,800 Pa·s to 2,900 Pa·s, 2,900 Pa·s to 3,000 Pa·s, 3,000 Pa·s to 3,100 Pa·s, 3,100 Pa·s to 3,200 Pa·s, 3,200 Pa·s to 3,300 Pa·s, 3,300 Pa·s to 3,400 Pa·s, 3,400 Pa·s to 3,500 Pa·s, 3,500 Pa·s to 3,600 Pa·s, 3,600 Pa·s to 3,700 Pa·s, 3,700 Pa·s to 3,800 Pa·s, 3,800 Pa·s to 3,900 Pa·s, 3,900 Pa·s to 4,000 Pa·s, 4,000 Pa·s to 4,100 Pa·s, 4,100 Pa·s to 4,200 Pa·s, 4,200 Pa·s to 4,300 Pa·s, 4,300 Pa·s to 4,400 Pa·s, 4,400 Pa·s to 4,500 Pa·s, 4,500 Pa·s to 4,600 Pa·s, 4,600 Pa·s to 4,700 Pa·s, 4,700 Pa·s to 4,800 Pa·s, 4,800 Pa·s to 4,900 Pa·s, 4,900 Pa·s to 5,000 Pa·s, 5,000 Pa·s to 5,100 Pa·s, 5,100 Pa·s to 5,200 Pa·s, 5,200 Pa·s to 5,300 Pa·s, 5,300 Pa·s to 5,400 Pa·s, 5,400 Pa·s to 5,500 Pa·s, 5,500 Pa·s to 5,600Pa s, 5,600Pa s~5,700Pa s, 5,700Pa s~5,800Pa s, 5,800Pa s~5,900Pa s, 5,900Pa s~6,000Pa s, 6,000Pa s~6,100Pa s, 6,100 Pa·s~6,200Pa·s, 6,200Pa·s~6,300Pa·s, 6,300Pa·s~6,400Pa·s, 6,400Pa·s~6,500Pa·s, 6,500Pa·s~6,600Pa·s, 6,600Pa·s~6,700Pa· s, 6,700Pa s~6,800Pa s, 6,800Pa s~6,900Pa s, 6,900Pa s~7,000Pa s, 7,000Pa s~7,100Pa s, 7,100Pa s~7,200Pa s, 7,200Pa s~7 ,300Pa·s, 7,300Pa·s~7,400Pa·s, 7,400Pa·s~7,500Pa·s, 7,500Pa·s~7,600Pa·s, 7,600Pa·s~7,700Pa·s, 7,700Pa·s~7,800Pa·s, 7,800 Pa·s~7,900Pa·s, 7,900Pa·s~8,000Pa·s, 8,000Pa·s~8,100Pa·s, 8,100Pa·s~8,200Pa·s, 8,200Pa·s~8,300Pa·s, 8,300Pa·s~8,400Pa· s, 8,400Pa s~8,500Pa s, 8,500Pa s~8,600Pa s, 8,600Pa s~8,700Pa s, 8,700Pa s~8,800Pa s, 8,800Pa s~8,900Pa s, 8,900Pa s~9 ,000 Pa·s, 9,000 Pa·s to 9,100 Pa·s, 9,100 Pa·s to 9,200 Pa·s, 9,200 Pa·s to 9,300 Pa·s, 9,300 Pa·s to 9,400 Pa·s, 9,400 Pa·s to 9,500 Pa·s, 9,500 Pa·s to 9,600 Pa·s, 9,600 Pa·s to 9,700 Pa·s, 9,700 Pa·s to 9,800 Pa·s, 9,800 Pa·s to 9,900 Pa·s, or 9,900 Pa·s to 10,000 Pa·s.

[0052] In some embodiments, after the composition forms a B-stage film, the B-stage film is subjected to a N 2 In some embodiments, after the composition forms a B-stage film, the B-stage film is rheologically stable at 10° C. / min using a DHR2 rheometer at a ramp rate of 10° C. / min and has a minimum film melt viscosity of 400 Pa·s to 7,000 Pa·s. 2 It has a minimum film melt viscosity of 500 Pa·s to 8,000 Pa·s, measured in

[0053] In some embodiments, after the composition forms a B-stage film, the B-stage film is 2 and has a differential scanning calorimetry (DSC) onset temperature of 130°C to 140°C, 140°C to 150°C, 150°C to 160°C, 160°C to 170°C, 170°C to 180°C, 180°C to 190°C, 190°C to 200°C, 200°C to 210°C, 210°C to 220°C, 220°C to 230°C, 230°C to 240°C, or 240°C to 250°C, as measured by DSC at a ramp rate of 10°C / min.

[0054] In some embodiments, after the composition forms a B-stage film, the B-stage film is 2 When measured by DSC at a ramp rate of 10°C / min in a liquid medium, the liquid has a differential scanning calorimetry (DSC) onset temperature of about 130°C to about 140°C, about 140°C to about 150°C, about 150°C to about 160°C, about 160°C to about 170°C, about 170°C to about 180°C, about 180°C to about 190°C, about 190°C to about 200°C, about 200°C to about 210°C, about 210°C to about 220°C, about 220°C to about 230°C, about 230°C to about 240°C, or about 240°C to about 250°C.

[0055] In some embodiments, after the composition forms a B-stage film, the B-stage film is 2 In some embodiments, after the composition forms a B-stage film, the B-stage film is heated to 300° C. and then cooled to 300° C. for 1 hour at 2 ...2 In some embodiments, after the composition forms a B-stage film, the B-stage film is heated to 300° C. and then cooled to 300° C. for 1 hour at 2 ... 2 In some embodiments, after the composition forms a B-stage film, the B-stage film is heated to 300° C. and then cooled to 300° C. for 1 hour at 2 ... 2 In some embodiments, after the composition forms a B-stage film, the B-stage film is heated to 300° C. and then cooled to 300° C. for 1 hour. 2 In some embodiments, after the composition forms a B-stage film, the B-stage film is heated to 300° C. and then cooled to 300° C. for 1 hour. 2 It has a DSC onset temperature of 170-180°C as measured by DSC at a ramp rate of 10°C / min.

[0056] In some embodiments, after the composition forms a B-stage film, the ΔT from the DSC onset temperature to the DSC peak temperature of the B-stage film is less than 20° C., less than 15° C., less than 10° C., or less than 5° C. In some embodiments, after the composition forms a B-stage film, the ΔT from the DSC onset temperature to the DSC peak temperature of the B-stage film is 0° C. to 5° C., 5° C. to 10° C., 10° C. to 15° C., or 15° C. to 20° C. In some embodiments, after the composition forms a B-stage film, the ΔT from the DSC onset temperature to the DSC peak temperature of the B-stage film is 0° C., 1° C., 2° C., 3° ​​C., 4° C., 5° C., 6° C., 7° C., 8° C., 9° C., 10° C., 11° C., 12° C., 13° C., 14° C., 15° C., 16° C., 17° C., 18° C., 19° C., or 20° C. Without wishing to be bound by theory, it is believed that a ΔT from the DSC onset temperature to the DSC peak temperature of less than 20° C., less than 15° C., less than 10° C., or less than 5° C., or between 0° C. and 5° C., 5° C. and 10° C., 10° C. and 15° C., or between 15° C. and 20° C., represents a fast cure rate, such as preventing the occurrence of solder extrusion (a phenomenon that, in at least some embodiments, renders the composition unsuitable or unsuitable for thermocompression bonding). Conversely, without wishing to be bound by theory, it is believed that a B-stage film having a ΔT from the DSC onset temperature to the DSC peak temperature of 20° C. or greater is not suitable for thermocompression bonding methods. For example, certain B-staged films prepared from compositions including bismaleimide resin, epoxy resin, and 4,4-diaminodiphenyl sulfone, but not including one or more imidazoles with potential thermal activity (e.g., one or more imidazoles comprising at least two electron-withdrawing groups, such as an imidazole comprising at least two electron-withdrawing groups as disclosed herein), are known to have a ΔT from the DSC onset temperature to the DSC peak temperature of 20° C. or greater, and, without wishing to be bound by theory, are believed to be unsuitable for thermocompression bonding methods.

[0057] In some embodiments, the present disclosure refers to a particular organic group as being "substituted". The term "substituted" means that the subject organic group has one or more substituents, where the substituent is an atom or group of atoms that replaces a hydrogen atom on the subject organic group. When an organic group is substituted, the substituent can replace one or more hydrogen atoms, from replacing exactly one hydrogen atom to replacing all hydrogen atoms on the subject organic group. When an organic group has multiple substituents, the substituents are independently selected and can be, but do not have to be, the same.

[0058] The present disclosure, in some embodiments, refers to certain organic groups as being “unsubstituted.” The term “unsubstituted” means that the subject organic group does not bear any substituents, as that term is defined above.

[0059] As noted above, the compositions of the present disclosure include, among other components, one or more imidazoles that contain at least two electron-withdrawing groups. In some embodiments, the imidazole that contains at least two electron-withdrawing groups is a substituted imidazole that contains a substituent at the 2-position and, optionally, a substituent at the 4-position, a substituent at the 5-position, and / or a substituent on the nitrogen at the 1-position. In some embodiments, the imidazole that contains at least two electron-withdrawing groups is a substituted imidazole that contains an electron-withdrawing substituent (also referred to herein as an electron-withdrawing group) at the 2-position and, optionally, a substituent at the 4-position, a substituent at the 5-position, and / or a substituent on the nitrogen at the 1-position.

[0060] Exemplary electron-withdrawing groups include, but are not limited to, substituted or unsubstituted aryl groups (e.g., phenyl), cyano (-CN), halide (-X) (e.g., fluoro (-F), bromo (-Br), and iodo (-I)), -CHO, -COOH, and amino (-NR 1 R 2 , where R 1 and R 2are independently selected from a hydrogen atom or a substituted or unsubstituted alkyl group), cyano (-CN), halide (-X) (e.g., fluoro (-F), bromo (-Br), and iodo (-I)), -CHO, -COOH, and amino (-NR 1 R 2 , where R 1 and R 2 are independently selected from a hydrogen atom, or a substituted or unsubstituted alkyl group), and an oxygen-containing group (e.g., an alkyl group substituted with one or more groups independently selected from one or more hydroxy groups). Without wishing to be bound by theory, it is believed that the electron-withdrawing group reduces the electron density on the imidazole ring (e.g., the tertiary nitrogen of the imidazole) and / or makes the imidazole less reactive (e.g., makes the tertiary nitrogen of the imidazole less reactive).

[0061] In some embodiments, the imidazole is represented by formula (I).

[0062] [ka]

[0063] During the ceremony, R 1 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R 2 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R 3 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R 4is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; provided that the imidazole contains at least two electron-withdrawing groups.

[0064] In some embodiments, the imidazole is a substituted or unsubstituted aryl group (e.g., phenyl), cyano (-CN), halide (-X), (e.g., fluoro (-F), bromo (-Br), and iodo (-I)), -CHO, -COOH, amino (-NR 1 R 2 , where R 1 and R 2 are independently selected from a hydrogen atom or a substituted or unsubstituted alkyl group), cyano (-CN), halide (-X), (e.g., fluoro (-F), bromo (-Br), and iodo (-I)), -CHO, -COOH, and amino (-NR 1 R 2 , where R 1 and R 2 are independently selected from a hydrogen atom, or a substituted or unsubstituted alkyl group, and an alkyl group substituted with one or more groups independently selected from an oxygen-containing group.

[0065] In some embodiments, the imidazole comprises at least two electron-withdrawing groups independently selected from the group consisting of hydroxymethyl and phenyl.

[0066] In some embodiments, the imidazole comprises at least two electron-withdrawing groups independently selected from organic groups that reduce the electron density on the imidazole ring and / or reduce the reactivity of the imidazole.

[0067] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 1 is H, substituted or unsubstituted C 1 -C 6Alkyl, and substituted or unsubstituted C 6 -C 10 aryl.

[0068] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 1 is H, substituted or unsubstituted C 1 -C 6 Alkyl, substituted C 6 The alkyl group is selected from the group consisting of aryl, and phenyl.

[0069] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 1 is H, and substituted or unsubstituted C 1 -C 6 is selected from the group consisting of alkyl.

[0070] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 1 is C 1 -C 6 is selected from the group consisting of alkyl.

[0071] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 1 is H.

[0072] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 2 is H, substituted or unsubstituted C 1 -C 6 Alkyl, and substituted or unsubstituted C 6 -C 10 aryl.

[0073] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 2 is H, substituted or unsubstituted C 1 -C6 Alkyl, substituted C 6 The alkyl group is selected from the group consisting of aryl, and phenyl.

[0074] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 2 is a substituted or unsubstituted C 1 -C 6 Alkyl, substituted C 6 The alkyl group is selected from the group consisting of aryl, and phenyl.

[0075] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 2 is unsubstituted C 1 -C 6 It is selected from the group consisting of alkyl and phenyl.

[0076] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 2 is phenyl.

[0077] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is H, substituted or unsubstituted C 1 -C 6 Alkyl, and substituted or unsubstituted C 6 -C 10 aryl.

[0078] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is H, substituted or unsubstituted C 1 -C 6 Alkyl, substituted C 6 aryl, and phenyl.

[0079] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is a substituted or unsubstituted C 1 -C 6 Alkyl, substituted C 6 aryl, and phenyl.

[0080] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is a substituted or unsubstituted C 1 -C 6 alkyl.

[0081] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is a substitution C 1 -C 6 alkyl.

[0082] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is a substitution C 1 -C 6 alkyl, wherein each independently selected substituted C 1 -C 6 Alkyl is halogen, hydroxy, cyano, C 1 -C 6 Alkoxy, carboxylic acids, esters (e.g., -C(O)OR 5 , where R 5 is a substituted or unsubstituted alkyl group), ketones (e.g., -C(O)R 6 , where R 6 is a substituted or unsubstituted alkyl group), amide (e.g., -C(O)N(R 7 )(R 8 ), where R 7 and R8 is independently selected from the group consisting of H, substituted alkyl, and unsubstituted alkyl), amino (e.g., -N(R 9 )(R 10 ), where R 9 and R 10 is independently selected from the group consisting of H, substituted alkyl, and unsubstituted alkyl), and thioalkyl (e.g., -SR 11 , where R 11 is a substituted or unsubstituted alkyl group.

[0083] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is a substitution C 1 -C 6 alkyl, wherein each independently selected substituted C 1 -C 6 Alkyl is halogen, hydroxy, cyano, C 1 -C 6 It is substituted with one or more substituents independently selected from the group consisting of alkoxy and carboxylic acid.

[0084] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is a substitution C 1 -C 6 alkyl, wherein each independently selected substituted C 1 -C 6 Alkyl is substituted with halogen, hydroxy, and C 1 -C 6 and is substituted with one or more substituents selected from the group consisting of alkoxy.

[0085] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is a substitution C1 -C 6 alkyl, wherein each independently selected substituted C 1 -C 6 The alkyl is substituted with one or more hydroxy groups.

[0086] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I), wherein R 3 and R 4 is a substitution C 1 -C 6 alkyl, wherein each independently selected substituted C 1 -C 6 The alkyl is substituted with exactly one hydroxy group.

[0087] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by formula (I): - R 1 is H and substituted or unsubstituted C 1 -C 6 selected from the group consisting of alkyl; - R 2 is a substituted or unsubstituted C 1 -C 6 Alkyl, substituted C 6 aryl, and phenyl; - R 3 and R 4 is a substitution C 1 -C 6 alkyl, wherein each independently selected substituted C 1 -C 6 Alkyl is halogen, hydroxy, cyano, C 1 -C 6 It is substituted with one or more substituents selected from the group consisting of alkoxy and carboxylic acid.

[0088] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by:

[0089] [ka]

[0090] In some embodiments, the imidazole containing at least two electron withdrawing groups is represented by:

[0091] [ka]

[0092] In some embodiments, compositions according to the present disclosure comprise adducts of one or more imidazoles with one or more agents described herein, in some embodiments, these imidazole adducts thermally dissociate to release one or more imidazoles.

[0093] In some embodiments, the one or more imidazoles having latent thermal activity are included in an amount ranging from about 0.5% to about 10% by weight. In some embodiments, the one or more imidazoles having latent thermal activity are included in an amount ranging from about 1% to about 8% by weight. In some embodiments, the one or more imidazoles having latent thermal activity are included in an amount ranging from about 2% to about 7% by weight. In some embodiments, the one or more imidazoles having latent thermal activity are included in an amount ranging from about 2.5% to about 6.5% by weight. In some embodiments, the one or more imidazoles having latent thermal activity are included in an amount ranging from about 3% to about 6% by weight. In some embodiments, the one or more imidazoles having latent thermal activity are included in an amount ranging from about 2.5% to about 4.5% by weight. In some embodiments, the one or more imidazoles having latent thermal activity are included in an amount ranging from about 1% to about 4% by weight. In some embodiments, the one or more imidazoles with latent thermal activity are included in an amount ranging from about 2% to about 4% by weight. In some embodiments, the one or more imidazoles with latent thermal activity are included in an amount ranging from about 2% to about 3.5% by weight. In some embodiments, the one or more imidazoles with latent thermal activity are included in an amount ranging from about 2% to about 3% by weight. In some embodiments, the one or more imidazoles with latent thermal activity are included in an amount ranging from about 2.5% to about 3.5% by weight. In some embodiments, the one or more imidazoles with latent thermal activity referred to in this paragraph are one or more imidazoles that include at least two electron-withdrawing groups.

[0094] In some embodiments, the maleimide-containing resin, the nadimide-containing resin, or the itaconimide-containing resin may be represented as follows:

[0095] [ka]

[0096] During the ceremony, m is 1 to 15, p is 0-15, Each R 2 is halogen or C 1-6 independently selected from alkyl, J is a monovalent or polyvalent radical containing organic and / or organosiloxane groups.

[0097] In some embodiments, J is: - a hydrocarbyl or substituted hydrocarbyl species typically having in the range of from about 6 to about 500 carbon atoms, the hydrocarbyl species being selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, alkylaryl, arylalkyl, arylalkenyl, alkenylaryl, arylalkynyl or alkynylaryl, with the proviso that X can be aryl only if X comprises a combination of two or more different species; - a hydrocarbylene or hydrocarbylene species typically having a range of from about 6 to about 500 carbon atoms, the hydrocarbylene species being selected from alkylene, alkenylene, alkynylene, cycloalkylene, cycloalkenylene, arylene, alkylarylene, arylalkylene, arylalkenylene, alkenylarylene, arylalkynylene, or alkynylarylene; - Substituted or unsubstituted C 6 -C 10 Aryl, - heterocyclic or substituted heterocyclic species, typically having in the range of from about 6 to about 500 carbon atoms; - polysiloxane, - polysiloxane-polyurethane block copolymers, or - one or more of the above with a covalent bond, -O-, -S-, -NR-, -NR-C(O)-, -NR-C(O)-O-, -NR-C(O)-NR-, -SC(O)-, -SC(O)-O-, -SC(O)-NR-, -OS(O) 2 -, -OS(O) 2 -O-, -OS(O) 2-NR-, -OS(O)-, -OS(O)-O-, -OS(O)-NR-, -O-NR-C(O)-, -O-NR-C(O)-O, -O-NR-C(O)-NR, -NR-OC(O)-, -NR-OC(O)-O-, -NR-OC(O)-NR-, -O-NR-C(S)-, -O-NR-C (S)-O-, -O-NR-C(S)-NR-, -NR-OC(S)-, -NR-OC(S)-O-, -NR-OC(S)-NR-, -OC(S)-, -OC(S)-O-, -OC(S)-NR-, -NR-C(S)-, -NR-C(S)-O-, -NR-C(S)-NR-, -SS(O) 2 -, -SS(O) 2- O-, -SS(O) 2 -NR-, -NR-OS(O)-, -NR-OS(O)-O-, -NR-OS(O)-NR-, -NR-OS(O) 2 -, -NR-OS(O) 2 -O-, -NR-OS(O) 2 -NR-, -O-NR-S(O)-, -O-NR-S(O)-O-, -O-NR-S(O)-NR-, -O-NR-S(O) 2 -O-, -O-NR-S(O) 2 -NR-, -O-NR-S(O) 2 -,-OP(O)R 2 -,-SP(O)R 2 - or -NR-P(O)R 2 -; in which R is independently halogen, alkyl, or substituted alkyl; is a monovalent or polyvalent group selected from

[0098] In some embodiments, J is substituted or unsubstituted C. 6aryl, oxyalkyl, thioalkyl, aminoalkyl, carboxylalkyl, oxyalkenyl, thioalkenyl, aminoalkenyl, carboxyalkenyl, oxyalkynyl, thioalkynyl, aminoalkynyl, carboxyalkynyl, oxycycloalkyl, thiocycloalkyl, aminocycloalkyl, carboxycycloalkyl, oxychloroalkenyl, thiocycloalkenyl, aminocycloalkenyl, carboxycycloalkenyl, heterocyclic, oxyheterocyclic, thioheterocyclic, aminoheterocyclic, carboxyheterocyclic, oxyaryl, thioaryl, aminoaryl, carboxyaryl, heteroaryl, oxyheteroaryl, thioheteroaryl, aminoheteroaryl, carboxyheteroaryl, oxyalkylaryl, thioalkylaryl, aminoalkylaryl, carboxyalkylaryl, oxyarylalkyl, thioarylalkyl, aminoarylalkyl, carboxyarylalkyl, oxyarylalkenyl, thioarylalkenyl, aminoarylalkenyl, carboxyarylalkenyl, oxyalkenylaryl, thi alkenylaryl, aminoalkenylaryl, carboxyalkenylaryl, oxyarylalkynyl, thioarylalkynyl, aminoarylalkynyl, carboxyarylalkynyl, oxyalkynylaryl, thioalkynylaryl, aminoalkynylaryl or carboxyalkynylaryl, oxyalkylene, thioalkylene, aminoalkylene, carboxyalkylene, oxyalkenylene, thioalkenylene, aminoalkenylene, carboxyalkenylene, oxyalkynylene, thioalkynylene, aminoalkenylene, alkynylene, carboxyalkynylene, oxycycloalkylene, thiocycloalkylene, aminocycloalkylene, carboxycycloalkylene, oxycycloalkenylene, thiocycloalkenylene, aminocycloalkenylene, carboxycycloalkenylene, oxyarylene, thioarylene, aminoarylene, carboxyarylene, oxyalkylarylene, thioalkylarylene, aminoalkylarylene, carboxyalkylarylene, oxyarylalkylene, thioarylalkylene, aminoarylalkylene,carboxyarylalkylene, oxyarylalkenylene, thioarylalkenylene, aminoarylalkenylene, carboxyarylalkenylene, oxyalkenylarylene, thioalkenylarylene, aminoalkenylarylene, carboxyalkenylarylene, oxyarylalkynylene, thioarylalkynylene, aminoarylalkynylene, carboxyarylalkynylene, oxyalkynylarylene, thioalkynylarylene, aminoalkynylarylene, carboxyalkynylarylene, heteroarylene, oxyheteroarylene, thioheteroarylene, aminoheteroarylene, carboxyheteroarylene, heteroatom-containing divalent or polyvalent cyclic moiety, oxyheteroatom-containing divalent or polyvalent cyclic moiety, thioheteroatom-containing divalent or polyvalent cyclic moiety, aminoheteroatom-containing divalent or polyvalent cyclic moiety, or carboxyheteroatom-containing divalent or polyvalent cyclic moiety.

[0099] In some embodiments, the maleimide-containing resin is represented by the following:

[0100] [ka]

[0101] During the ceremony, Each R is independently selected from the group consisting of H and substituted or unsubstituted alkyl; each m is independently selected from the group consisting of 0, 1, 2, 3, and 4; n is 0, 1, 2, 3, 4, and 5.

[0102] In some embodiments, the composition comprises a compound represented by the following formula:

[0103] [ka]

[0104] This compound is BMI-5100 (chemical name: 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide; Daiwa Kasei, Japan), which has a number average molecular weight of about 300 as determined by gel permeation chromatography (GPC).

[0105] In some embodiments, the maleimide-containing resin is represented by the following:

[0106] [ka]

[0107] In the formula, n is 0, 1, 2, 3, 4 or 5.

[0108] In some embodiments, the maleimide-containing resin is a BMI resin having a maleimide equivalent weight of 180 to 400. Maleimide equivalent weight is the weight in grams of a resin containing one equivalent of maleimide functional groups. In some embodiments, the maleimide-containing resin is a BMI resin having a maleimide equivalent weight of 220. In some embodiments, the maleimide-containing resin is a BMI resin having a maleimide equivalent weight of 300. In some embodiments, the maleimide-containing resin is a BMI resin having a maleimide equivalent weight of about 400. In some embodiments, the maleimide-containing resin is a BMI resin having a maleimide equivalent weight of about 390 to about 400. In some embodiments, the maleimide-containing resin is a BMI resin having a maleimide equivalent weight of 390 to 400.

[0109] In some embodiments, the maleimide-containing resin is included in an amount ranging from about 1% to about 20% by weight. In some embodiments, the maleimide-containing resin is included in an amount ranging from about 1% to about 15% by weight. In some embodiments, the maleimide-containing resin is included in an amount ranging from about 3% to about 15% by weight. In some embodiments, the maleimide-containing resin is included in an amount ranging from about 1% to about 5% by weight. In some embodiments, the maleimide-containing resin is included in an amount ranging from about 5% to about 20% by weight. In some embodiments, the maleimide-containing resin is included in an amount ranging from about 5% to about 15% by weight. In some embodiments, the maleimide-containing resin is included in an amount ranging from about 10% to about 20% by weight. In some embodiments, the maleimide-containing resin is included in an amount ranging from about 10% to about 15% by weight. In some embodiments, the maleimide-containing resin is included in an amount ranging from about 12% to about 17% by weight. In some embodiments, the maleimide-containing resin is present at about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, or about 20% by weight.

[0110] In some embodiments, the itaconimide-containing resin is represented by the following:

[0111] [ka]

[0112] In the formula, Ar is a substituted or unsubstituted aryl group.

[0113] In some embodiments, the itaconimide-containing resin is:

[0114] [ka]

[0115] In some embodiments, the nadimide is represented by the following:

[0116] [ka]

[0117] During the ceremony, Ar is substituted or unsubstituted aryl; R is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.

[0118] As mentioned above, the composition of the present disclosure includes one or more epoxy resins among other components. A wide variety of epoxy-functionalized resins are contemplated for use herein, such as liquid epoxy resins based on bisphenol A, solid epoxy resins based on bisphenol A, liquid epoxy resins based on bisphenol F (e.g., Epicron EXA-835LV), multifunctional epoxy resins based on phenol novolac resins, dicyclopentadiene-type epoxy resins (e.g., Epicron HP-7200L), naphthalene-type epoxy resins, and the like, as well as mixtures of any two or more thereof.

[0119] Exemplary epoxy-functionalized resins contemplated for use herein include diepoxides of cycloaliphatic alcohols, hydrogenated bisphenol A (commercially available as Epalloy 5000), difunctional cycloaliphatic glycidyl esters of hexahydrophthalic anhydride (commercially available as Epalloy 5200), Epicron EXA-835LV, Epicron HP-7200L, and the like, as well as mixtures of any two or more thereof.

[0120] In certain embodiments, the epoxy component may include a combination of two or more different bisphenol-based epoxies. These bisphenol-based epoxies may be selected from bisphenol A, bisphenol F, or bisphenol S epoxies, or combinations thereof. Additionally, two or more different bisphenol epoxies may be used within the same type of resin (such as A, F, or S).

[0121] Commercially available examples of bisphenol epoxies contemplated for use herein include bisphenol F type epoxies (RE-404-S from Nippon Kayaku Co., Ltd. (Japan), Epicron 830 (RE1801), 830S (RE1815), 830A (REI826), and 830W from Dainippon Ink and Chemicals, Inc., and RSL1738 and YL-983U from Resolution) and bisphenol A type epoxies (YL-979 and 980 from Resolution).

[0122] The above bisphenol epoxies, available commercially from Dainippon Ink and Chemicals, are advertised as liquid undiluted epichlorohydrin-bisphenol F epoxies with much lower viscosities than conventional epoxies based on bisphenol A epoxies, and have similar physical properties to liquid bisphenol A epoxies. The bisphenol F epoxies have lower viscosities than the bisphenol A epoxies, all else being the same between the two epoxies, resulting in lower viscosities and faster flowing underfill sealant materials. The EEW of these four bisphenol F epoxies is 165-180. Viscosities at 25°C are 3,000-4,500 cps (except for RE1801, which has a viscosity upper limit of 4,000 cps). Hydrolyzable chloride content is reported to be 200 ppm for RE1815 and 830W, and 100 ppm for RE1826.

[0123] The bisphenol epoxies available from Resolution and discussed above are advertised as low chloride content liquid epoxies. The bisphenol A epoxies have an EEW (g / eq) of 180-195 and a viscosity at 25°C of 100-250 cps. The total chloride content of YL-979 is reported to be 500-700 ppm, and the total chloride content of YL-980 is reported to be 100-300 ppm. The bisphenol F epoxies have an EEW (g / eq) of 165-180 and a viscosity at 25°C of 30-60. The total chloride content of RSL-1738 is reported to be 500-700 ppm, and the total chloride content of YL-983U is reported to be 150-350 ppm.

[0124] In addition to bisphenol epoxies, other epoxy compounds are contemplated for use as the epoxy component of the compositions of the present disclosure. For example, cycloaliphatic epoxies such as 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexylcarbonate can be used. Monofunctional, difunctional or multifunctional reactive diluents may also be used to adjust the viscosity and / or reduce the Tg of the resulting resin material. Examples of reactive diluents include butyl glycidyl ether, cresyl glycidyl ether, polyethylene glycol glycidyl ether, polypropylene glycol glycidyl ether, and the like.

[0125] Epoxies suitable for use herein include polyglycidyl derivatives of phenolic compounds, such as Epon 828, Epon 1001, Epon 1009, and Epon 1031, available under the tradename Epon from Resolution, Inc.; DER 331, DER 332, DER 334, and DER 542 from The Dow Chemical Company; and Blen-S from Nippon Kayaku Co., Ltd. Other suitable epoxies include polyepoxides prepared from polyols and the like, and polyglycidyl derivatives of phenol-formaldehyde novolacs, such as DEN 431, DEN 438, and DEN 439 from The Dow Chemical Company. Cresol analogs are available under the tradename Araldite, such as Araldite ECN 1235, Araldite ECN 1273, and Araldite ECN 1299 from Ciba Specialty Chemicals, Inc. SU-8 is a bisphenol A type epoxy novolac available from Resolution. Polyglycidyl adducts of amines, aminoalcohols and polycarboxylic acids are also useful in the present invention, commercially available resins include Glyamine 135, Glyamine 125, and Glyamine 115 from FIC; Araldite MY-720, Araldite 0500, and Araldite 0510 from Chiba Specialty Chemicals; and PGA-X and PGA-C from Sherwin-Williams.

[0126] Suitable monofunctional epoxy coreactant diluents for optional use herein include those having a viscosity lower than that of the epoxy component, typically less than about 250 cps. The monofunctional epoxy coreactant diluent may have an epoxy group having an alkyl group having from about 6 to about 28 carbon atoms, examples of which include C 6~28 Alkyl glycidyl ether, C 6~28 Fatty acid glycidyl ester, C 6~28 Alkylphenol glycidyl ether and the like.

[0127] In some embodiments, the epoxy resin is novolac epoxy EEW200, novolac epoxy EEW300, or novolac epoxy EEW140.

[0128] In some embodiments, the epoxy resin is a compound represented by the following formula:

[0129] [ka]

[0130] In the formula, n is 0, 1, 2, 3, 4 or 5, and m is 0, 1, 2, 3, 4 or 5.

[0131] In some embodiments, the epoxy resin is included in an amount ranging from about 1% to about 30% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 1% to about 25% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 1% to about 20% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 1% to about 15% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 3% to about 15% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 1% to about 5% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 5% to about 20% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 5% to about 15% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 10% to about 20% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 15% to about 30% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 15% to about 25% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 10% to about 15% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 10% to about 15% by weight. In some embodiments, the epoxy resin is included in an amount ranging from about 10% to about 11% by weight, about 12% by weight, about 13% by weight, about 14% by weight, about 15% by weight, about 16% by weight, about 17% by weight, about 18% by weight, about 19% by weight, about 20% by weight, about 21% by weight, about 22% by weight, about 23% by weight, about 24% by weight, about 25% by weight, about 26% by weight, about 27% by weight, about 28% by weight, about 29% by weight, or about 30% by weight.

[0132] In some embodiments, the film-forming binder resin is included in an amount ranging from about 1% to about 25% by weight. In some embodiments, the film-forming binder resin is included in an amount ranging from about 1% to about 20% by weight. In some embodiments, the film-forming binder resin is included in an amount ranging from about 10% to about 20% by weight. In some embodiments, the film-forming binder resin is included in an amount ranging from about 13% to about 18% by weight. In some embodiments, the film-forming binder resin is included in an amount ranging from about 14% to about 16% by weight. In some embodiments, the film-forming binder resin is comprised at about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, about 20%, about 21%, about 22%, about 23%, about 24%, or about 25% by weight.

[0133] The compositions of the present disclosure include, among other components, one or more (meth)acrylate-containing resins, as described above. In some embodiments, the (meth)acrylic resin is represented by the following:

[0134] [ka]

[0135] In the formula, n is 0, 1, 2, 3, 4 or 5.

[0136] In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 1% to about 20% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 1% to about 15% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 3% to about 15% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 1% to about 5% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 5% to about 20% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 5% to about 15% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 10% to about 20% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 10% to about 15% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount ranging from about 12% to about 17% by weight. In some embodiments, the (meth)acrylate-containing resin is included in an amount of about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, or about 20% by weight.

[0137] The compositions of the present disclosure include, among other ingredients, one or more inorganic fillers, as described above. In some embodiments, the filler is an electrically non-conductive filler, such as silica. In some embodiments, the filler is silica, calcium silicate, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, aluminum oxide (Al 2 0 3 ), zinc oxide (ZnO), magnesium oxide (MgO), aluminum nitride (AlN), boron nitride (BN), carbon nanotubes, diamond, clay, aluminosilicates, etc., as well as mixtures of any two or more thereof.

[0138] In some embodiments, the inorganic filler is an inorganic non-conductive filler comprising particles having a maximum particle size of 5 μm or less than 5 μm. For example, in some embodiments, the filler has a particle size of about 0.1 μm to about 5 μm or 0.1 μm to 5 μm. In some embodiments, the loading of the filler is sufficient to meet the requirements of the underfill material. In some embodiments, the filler is included in an amount ranging from about 10% to about 70% by weight. In some embodiments, the filler is included in an amount ranging from about 20% to about 60% by weight. In some embodiments, the filler is included in an amount ranging from about 25% to about 55% by weight. In some embodiments, the filler is included in an amount ranging from about 30% to about 50% by weight. In some embodiments, the filler is included in an amount ranging from about 35% to about 45% by weight. In some embodiments, the filler is present at about 35%, about 36%, about 37%, about 38%, about 39%, about 40%, about 41%, about 42%, about 43%, about 44%, or about 45% by weight.

[0139] The compositions of the present disclosure, as described above, include one or more additives selected from the group consisting of adhesion promoters and film formers, among other ingredients.

[0140] As used herein, the term "adhesion promoter" refers to compounds that enhance the adhesive properties of the formulations into which they are introduced. Adhesion promoters can be organic or inorganic compounds and can include combinations thereof. Non-limiting examples of adhesion promoters include organozirconate compounds, organotitanate compounds, and silane coupling agents. In some embodiments, the adhesion promoter is Dow's Z6040.

[0141] In some embodiments, the adhesion promoter is included in an amount ranging from about 0.1% to about 5% by weight. In some embodiments, the adhesion promoter is included in an amount ranging from about 0.1% to about 1.0% by weight. In some embodiments, the adhesion promoter is included in an amount ranging from about 0.5% to about 1.0% by weight. In some embodiments, the adhesion promoter is included in an amount ranging from about 0.5% to about 1.5% by weight. In some embodiments, the adhesion promoter is included in an amount ranging from about 1% to about 2% by weight, about 2% to about 3% by weight, about 3% to about 4% by weight, or about 4% to about 5% by weight.

[0142] As used herein, the term "film former" refers to a compound that aids in the formation of a film, such as by increasing the viscosity of the combined materials (as a non-limiting example). Non-limiting examples of film formers, including elastomer additive components, include, but are not limited to, copolymerized ethylene acrylic elastomers, natural or synthetic rubbers such as substituted polyethylene, resins such as polyvinyl butyral resins and chlorosulfonated polyethylene synthetic rubbers (CSM), partially crosslinked butyl rubber compounds such as butyl rubber products available under the brand names Carrara®, DPR®, Isolene® and Karen® from Royal Elastomer of New Jersey, and ethylene acrylic elastomer materials such as Vamac® available from DuPont. Further non-limiting examples of film formers include, but are not limited to, acrylic polymers (e.g., polymers containing glycidyl functional groups), such as butyl acrylate-ethyl acrylate-acetonitrile copolymers and ethyl acrylate-acetonitrile copolymers, such as copolymers available from Nagase JP.

[0143] In some embodiments, the film former is included in an amount ranging from about 15 to about 40% by weight. In some embodiments, the film former is included in an amount ranging from about 15 to about 30% by weight. In some embodiments, the film former is included in an amount ranging from about 20 to about 30% by weight. In some embodiments, the film former is included in an amount ranging from about 22 to about 28% by weight. In some embodiments, the film former is included in an amount ranging from about 23 to about 26% by weight. In some embodiments, the film former is included in an amount ranging from about 23 to about 25% by weight. In some embodiments, the film former is included in an amount ranging from about 24%, about 25%, or about 26% by weight.

[0144] In some embodiments, the compositions of the present disclosure further comprise one or more fluxing agents.

[0145] As used herein, the term "fluxing agent" refers to a reducing agent that prevents oxides from forming on the surface of molten metal. Non-limiting examples of fluxing agents include compounds having at least one (meth)acrylate group and at least one carboxylic acid group, carboxylic acids (including but not limited to compounds having one or more acrylic acid functional groups, rosin gum, dodecanedioic acid (commercially available from Aldrich as Caufrey M2), adipic acid, sebacic acid, polybasic polyanhydrides, maleic acid, tartaric acid, citric acid, etc.), alcohols, hydroxyl acids and bases, polyols (including but not limited to ethylene glycol, glycerin, 3-[bis(glycidyloxymethyl)methoxy]-1,2-propanediol, D-ribose, D-cellobiose, cellulose, 3-cyclohexene-1,1-dimethanol, etc.).

[0146] In some embodiments, the fluxing agent is included in an amount ranging from about 1 to about 10% by weight. In some embodiments, the fluxing agent is included in an amount ranging from about 1 to about 5% by weight. In some embodiments, the fluxing agent is included in an amount ranging from about 5 to about 10% by weight. In some embodiments, the fluxing agent is included in an amount ranging from about 2 to about 8% by weight. In some embodiments, the fluxing agent is included in an amount ranging from about 3 to about 7% by weight. In some embodiments, the fluxing agent is included in an amount ranging from about 3 to about 5% by weight. In some embodiments, the fluxing agent is included in an amount ranging from about 3 to about 7% by weight. In some embodiments, the fluxing agent is included in an amount ranging from about 3 to about 7% by weight. In some embodiments, the fluxing agent is included in an amount of about 3%, about 4%, or about 5% by weight.

[0147] Embodiments of the present disclosure also relate to methods of preparing B-staged and / or cured films.

[0148] In some embodiments, a method of preparing a cured film includes: one or more resins selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins; one or more imidazoles having potential thermal activity, one or more inorganic fillers, and one or more additives selected from the group consisting of adhesion promoters and film formers; preparing a composition comprising: casting the composition into a film; exposing the cast film to an elevated temperature to cure the film; Includes.

[0149] In some embodiments, a method of preparing a cured film includes: one or more resins selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins; one or more imidazoles containing at least two electron withdrawing groups; one or more inorganic fillers, and one or more additives selected from the group consisting of adhesion promoters and film formers; preparing a composition comprising: casting the composition into a film; exposing the cast film to an elevated temperature to cure the film; Includes.

[0150] In some embodiments, a method of preparing a cured film includes: one or more resins selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins; one or more imidazoles having potential thermal activity, one or more inorganic fillers, one or more additives selected from the group consisting of adhesion promoters and film formers; and one or more fluxing agents; preparing a composition comprising: casting the composition into a film; exposing the cast film to an elevated temperature to cure the film; Includes.

[0151] In some embodiments, a method of preparing a cured film includes: one or more resins selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins; one or more imidazoles containing at least two electron withdrawing groups; one or more inorganic fillers, one or more additives selected from the group consisting of adhesion promoters and film formers; and One or more fluxing agents preparing a composition comprising: casting the composition into a film; exposing the cast film to an elevated temperature to cure the film; Includes.

[0152] In some embodiments of the method of preparing a cured film, the one or more resins are selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins, where the maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenolic-containing resins are as disclosed elsewhere herein, and are optionally present in the amounts disclosed elsewhere herein.

[0153] In some embodiments of the method of preparing a cured film, the one or more imidazoles are as disclosed elsewhere herein, and are optionally present in the amounts disclosed elsewhere herein.

[0154] In some embodiments of the method of preparing a cured film, the one or more imidazoles are as disclosed elsewhere herein, and are optionally present in the amounts disclosed elsewhere herein.

[0155] In some embodiments of the method of preparing a cured film, the one or more inorganic fillers are as disclosed elsewhere herein, and are optionally present in the amounts disclosed elsewhere herein.

[0156] In some embodiments of the method of preparing a cured film, one or more additives selected from the group consisting of adhesion promoters and film formers are disclosed elsewhere herein, and are optionally present in the amounts disclosed elsewhere herein.

[0157] In some embodiments of the method of preparing a cured film, the one or more fluxing agents are as disclosed elsewhere herein, and are optionally present in the amounts disclosed elsewhere herein.

[0158] In some embodiments of the method of preparing a cured film, the one or more fluxing agents are compounds having at least one (meth)acrylate group and at least one carboxylic acid group, optionally present in amounts disclosed elsewhere herein.

[0159] In some embodiments of the method of preparing a cured film, the one or more fluxing agents are one or more fluxing agents described herein, optionally present in the amounts disclosed elsewhere herein.

[0160] In some embodiments, films prepared according to the methods of preparing a cured film disclosed herein have the physical properties of the films disclosed elsewhere herein. For example, in some embodiments, films prepared according to the methods of preparing a film disclosed herein have the physical properties of the films disclosed elsewhere herein. For example, in some embodiments, films prepared according to the methods of preparing a film disclosed herein have the Tg, storage modulus at 25° C., storage modulus at 230° C., storage modulus at 250° C., CTE, DSC onset temperature, and N measured by DSC at a ramp rate of 10° C. / min, as disclosed elsewhere herein. 2 and having one or more of the lowest film melt viscosities measured using a DHR2 rheometer at a ramp rate of 10° C. / min.

[0161] In some embodiments, a film prepared according to the methods of preparing a film disclosed herein has the following physical properties: Tg>200°C as measured by dynamic mechanical analysis (DMA); Storage modulus at 25℃ < 6.5GPa, Storage modulus at 250°C > 0.1 GPa, and Coefficient of Thermal Expansion (CTE) <250ppm / ℃.

[0162] In some embodiments, a film prepared according to the methods of preparing a film disclosed herein has the following physical properties: Tg>230°C as measured by dynamic mechanical analysis (DMA); Storage modulus at 25℃ < 5GPa, Storage modulus at 230°C > 0.3 GPa, and Coefficient of Thermal Expansion (CTE) <120ppm / ℃.

[0163] In some embodiments, a film prepared according to the methods of preparing a film disclosed herein has the following physical properties: Tg>240°C as measured by dynamic mechanical analysis (DMA); Storage modulus at 25℃ < 5.5GPa, Storage modulus at 230°C > 0.6 GPa, and Coefficient of Thermal Expansion (CTE) <80ppm / ℃.

[0164] In some embodiments, a film prepared according to the methods of preparing a film disclosed herein has the following physical properties: Tg measured by dynamic mechanical analysis (DMA) is 240℃~300℃, Storage modulus at 25°C is 4.0GPa to 5.5GPa, and The storage modulus at 230℃ is 0.6GPa~1.2GPa.

[0165] In some embodiments, a film prepared according to the methods of preparing a film disclosed herein has the following physical properties: Tg measured by dynamic mechanical analysis (DMA) is 240℃~300℃, Storage modulus at 25℃ is 4.0GPa~5.5GPa, Storage modulus at 230℃ is 0.6GPa to 1.2GPa, and Use a DHR2 rheometer at a ramp rate of 10 °C / min. 2 The minimum film melt viscosity measured is 900 Pa·s to 6,500 Pa·s.

[0166] In some embodiments, a film prepared according to the methods of preparing a film disclosed herein has the following physical properties: Tg measured by dynamic mechanical analysis (DMA) is 240℃~300℃, Storage modulus at 25℃ is 4.0GPa~5.5GPa, Storage modulus at 230℃ is 0.6GPa to 1.2GPa, and Coefficient of thermal expansion (CTE) is 50ppm / ℃~80ppm / ℃.

[0167] In some embodiments, a film prepared according to the methods of preparing a film disclosed herein has the following physical properties: Tg measured by dynamic mechanical analysis (DMA) is 240℃~300℃, Storage modulus at 25℃ is 4.0GPa~5.5GPa, Storage modulus at 230℃ is 0.6GPa~1.2GPa, Coefficient of thermal expansion (CTE) is 50ppm / ℃~80ppm / ℃, and Use a DHR2 rheometer at a ramp rate of 10 °C / min. 2 The minimum film melt viscosity measured is 900 Pa·s to 6,500 Pa·s. EXAMPLES

[0168] An exemplary embodiment including components of a composition according to the present disclosure is shown in Table 1. Imidazole A is 4-methyl-2-phenyl-1H-imidazole-5-methanol. Imidazole B is 2-phenyl-4,5-dihydroxymethylimidazole.

[0169] [Table 2]

[0170] Properties of certain exemplary embodiments of compositions according to the present disclosure are shown in Table 2.

[0171] [Table 3]

[0172] The components of a further exemplary composition according to the present disclosure ("Example 8") and four comparative compositions (not within the scope of the present disclosure) (Comparative Examples 1-4) are shown in Table 3A, and the physical properties of these compositions are shown in Table 3B. Imidazole A is 4-methyl-2-phenyl-1H-imidazole-5-methanol. Imidazole C is 2-phenylimidazole. Imidazole D is 2-ethyl-4-methyl-1H-imidazole-1-propanenitrile.

[0173] [Table 4]

[0174] [Table 5]

[0175] As shown in Table 3A, the compositions of Example 8, Comparative Example 1, and Comparative Example 4 each contained an imidazole curing agent, but the compositions of Comparative Example 1 and Comparative Example 4 did not contain an imidazole having at least two electron-withdrawing groups, whereas the composition of Example 8 contained an imidazole having at least two electron-withdrawing groups. However, as shown in Table 3B, the composition of Example 8, unlike the composition of Comparative Example 1, had a ΔT from the DSC onset temperature to the DSC peak temperature of less than 20° C. (rounded to the nearest integer).

[0176] Also, as shown in Table 3B, unlike the composition of Comparative Example 4, the composition of Example 8 has a DSC onset temperature of 130° C. to 250° C. (specifically, 148.40° C.) when measured by DSC at a ramp rate of 10° C. / min. 2 The composition has a minimum film melt viscosity of 10 Pa·s to 10,000 Pa·s (specifically, 5,936 Pa·s) when measured using a DHR2 rheometer at a ramp rate of 10 °C / min in

[0177] The composition of Example 8 was demonstrated to form good solder interconnects, be free of material entrapment and voids, and also to have a higher Tg, lower CTE, and better high temperature properties compared to the comparative examples. The composition of Comparative Example 3 was also demonstrated to form good solder interconnects, be free of material entrapment and voids, but the compositions of Comparative Examples 1-4 all demonstrated inferior high temperature properties compared to Example 8. The compositions of Comparative Examples 1, 2, and 4 were deemed unsuitable for thermocompression bonding processes.

[0178] Thus, without wishing to be bound by theory, it is believed that compositions that include imidazoles that have potential thermal activity, such as imidazoles that include at least two electron-withdrawing groups, have characteristics such as, but not limited to, DSC onset temperature, melt viscosity, and ΔT from the DSC onset temperature to the DSC peak temperature that make them more suitable for thermocompression bonding processes, whereas compositions that include imidazoles that do not have potential thermal activity, such as imidazoles that have one or no electron-withdrawing groups, or compositions that do not include imidazole, are less suitable for thermocompression bonding processes.

[0179] DSC, melt viscosity, DMA and TMA data relating to the exemplary composition of Example 3 are provided in Figures 1, 2, 3 and 4, respectively. DSC, melt viscosity, DMA and TMA data relating to the exemplary composition of Example 8 are provided in Figures 5, 6, 7 and 8, respectively.

Claims

1. One or more resins selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenol-containing resins, One or more imidazoles having latent thermal activity, One or more inorganic fillers, and One or more additives selected from the group consisting of adhesion promoters and film-forming agents, A composition comprising: After the composition forms a film, the film has the following physical properties: Tg > 200 °C measured by dynamic mechanical analysis (DMA), Storage modulus at 25 °C < 6.5 GPa, Storage modulus at 250 °C > 0.1 GPa, and Coefficient of thermal expansion (CTE) < 250 ppm / °C, The composition having the above properties.

2. After the composition forms a film, the film has the following physical properties: Tg > 230 °C measured by dynamic mechanical analysis (DMA), Storage modulus at 25 °C < 5 GPa, Storage modulus at 230 °C > 0.3 GPa, and Coefficient of thermal expansion (CTE) < 120 ppm / °C, The composition according to Claim 1 having the above properties.

3. The composition according to Claim 1 or 2, wherein the imidazole having latent activity is an imidazole containing at least two electron-withdrawing groups.

4. The composition according to Claim 1 or 2, wherein the imidazole is a substituted imidazole containing an electron-withdrawing group at the 2-position and containing a substituent at the 4-position, a substituent at the 5-position, and / or a substituent on the nitrogen at the 1-position.

5. The composition according to Claim 1 or 2, wherein the imidazole contains at least two electron-withdrawing groups independently selected from organic groups that reduce the electron density of the imidazole ring and / or weaken the reactivity of the imidazole.

6. The imidazole is a substituted or unsubstituted aryl group, cyano (-CN), halide (-X), -CHO, -COOH, -NR １ R ２ (wherein R １ and R ２ are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group, cyano (-CN), halide (-X), -CHO, -COOH, and -NR １ R ２ (wherein R １ and R ２ are each independently selected from a hydrogen atom, or a substituted or unsubstituted alkyl group and an oxygen-containing group), and is an alkyl group substituted with one or more groups independently selected from the group consisting of), the composition according to claim 1 or 2, comprising at least two electron-withdrawing groups independently selected from the group.

7. The composition according to Claim 1 or 2, wherein the imidazole contains at least two electron-withdrawing groups independently selected from hydroxymethyl and phenyl.

8. The imidazole is 【Chemical 1】 (wherein R １ is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, R ２ is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, R ３ is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, R ４ is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl) represented by provided that the imidazole contains at least two electron-withdrawing groups), the composition according to Claim 1 or 2.

9. R ２ is C １－６ alkyl and C ６ The composition according to claim 8, wherein the composition is selected from the group consisting of aryl.

10. The maleimide-containing resin is [[Chemical 2]] (wherein each R is independently selected from the group consisting of H and substituted or unsubstituted alkyl; each m is independently selected from the group consisting of 0, 1, 2, 3, or 4; n is 0, 1, 2, 3, 4, or 5), a compound represented by or 【Chemical Formula 3】 (wherein n is 0, 1, 2, 3, 4, or 5) The composition according to claim 1 or 2, which is a compound represented by

11. wherein the (meth)acrylic resin is 【Chemical Formula 4】 (wherein n is 0, 1, 2, 3, 4 or 5) The composition according to claim 1 or 2, which is represented by

12. wherein the epoxy resin is 【Chemical Formula 5】 (wherein n is 0, 1, 2, 3, 4 or 5 and m is 0, 1, 2, 3, 4 or 5) The composition according to claim 1 or 2, which is a compound represented by

13. After the composition forms a film, the film has the following physical properties: The differential scanning calorimetry (DSC) onset temperature measured by DSC at a ramp rate of 10 °C / min is 130 °C to 250 °C, and Using a DHR2 rheometer at a ramp rate of 10 °C / min, the minimum film melt viscosity measured in N ２ is 10 Pa·s to 10,000 Pa·s, The composition according to claim 1 or 2, which has

14. After the composition forms a film, the film has the following physical properties: The differential scanning calorimetry (DSC) onset temperature measured by DSC at a ramp rate of 10 °C / min is 150 °C to 190 °C, and Using a DHR2 rheometer at a ramp rate of 10 °C / min, the minimum film melt viscosity measured in N ２ is 400 Pa·s to 7,000 Pa·s, The composition according to claim 1 or 2, which has

15. After the composition forms a film, ΔT from the DSC onset temperature to the DSC peak temperature of the film is less than 20 °C or less than 15 °C. The composition according to claim 1 or 2.

16. After the composition forms a film, ΔT from the DSC onset temperature to the DSC peak temperature of the film is less than 10 °C or less than 5 °C. The composition according to claim 1 or 2.

17. A step of preparing the composition according to claim 1 or 2; A step of molding the composition into a film; A step of exposing the molded film to a high temperature to cure the film; A method for preparing a cured film, which includes

18. One or more resins selected from the group consisting of maleimide-containing resins, nadimide-containing resins, itaconimide-containing resins, epoxy resins, (meth)acrylate-containing resins, and phenol-containing resins, One or more imidazoles having latent thermal activity, One or more inorganic fillers, and One or more additives selected from the group consisting of adhesion promoters and film formers, A step of preparing a composition containing A step of molding the composition into a film; A step of exposing the molded film to a high temperature to cure the film; A method for preparing a cured film, which includes

19. The method according to claim 18, wherein the one or more imidazoles having latent thermal activity are imidazoles containing one or more at least two electron-withdrawing groups.

20. wherein said one or more imidazoles are 【Chemical Formula 6】 (wherein, R １ is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, R ２ is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, R ３ is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, R ４ (wherein R is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl) represented by provided that said imidazole contains at least two electron-withdrawing groups, the method according to claim 18.

21. R ２ is C １－６ alkyl and C ６ The method according to claim 18, wherein the group is selected from the group consisting of aryl.

22. wherein said maleimide-containing resin is 【Chemical Formula 7】 wherein each R is independently selected from the group consisting of H and substituted or unsubstituted alkyl; each m is independently selected from the group consisting of 0, 1, 2, 3 or 4; n is 0, 1, 2, 3, 4 or 5 and is a compound represented by or 【Chemical 8】 wherein n is 0, 1, 2, 3, 4 or 5 and is a compound represented by, the method according to claim 18.

23. wherein said (meth)acrylic resin is 【Chemical Formula 9】 wherein n is 0, 1, 2, 3, 4 or 5 and is represented by, the method according to claim 18.

24. wherein said epoxy resin is 【Chemical Formula 10】 wherein n is 0, 1, 2, 3, 4 or 5 and m is 0, 1, 2, 3, 4 or 5 and is a compound represented by, the method according to claim 18.

25. A cured film prepared according to the method according to claim 18.

26. wherein said film has the following physical properties: Tg > 200 °C measured by dynamic mechanical analysis (DMA), storage modulus at 25 °C < 6.5 GPa, storage modulus at 250 °C > 0.1 GPa, and coefficient of thermal expansion (CTE) < 250 ppm / °C, and is a film prepared according to the method according to claim 18.

27. wherein said film has the following physical properties: Tg > 230 °C measured by dynamic mechanical analysis (DMA), storage modulus at 25 °C < 5 GPa, storage modulus at 230 °C > 0.3 GPa, and coefficient of thermal expansion (CTE) < 120 ppm / °C, and is a film prepared according to the method according to claim 18.

28. The film according to claim 25, wherein said film is an underfill film.

29. The film according to claim 25, wherein said film is a wafer-level underfill film (WAUF).

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