JP7259220B2 - Photosensitive resin composition, wiring layer and semiconductor device - Google Patents

Description

TECHNICAL FIELD The present disclosure relates to a photosensitive resin composition, a wiring layer and a semiconductor device.

From the viewpoint of high-speed transmission required for next-generation mobile communication systems or servers, there is a trend toward higher-frequency electrical signals and higher-density wiring. Package technology using organic substrates with high-density wiring (organic interposers) and fan-out package technology (TMV: Through Mold Via) are used to mount multiple chips at high density. FO-WLP: Fan Out-Wafer Level Package), package technology using silicon or glass interposer, package technology using through-silicon via (TSV: Through Silicon Via), chips embedded in substrates are used for chip-to-chip transmission Package technology and the like have been proposed.

In particular, when semiconductor chips are mounted on an organic interposer and an FO-WLP, fine wiring is required for high-density conduction between the semiconductor chips (see, for example, Patent Document 1 below).

A material with a low dielectric loss tangent is desired as an organic material that is applied to suppress transmission loss when used in a high frequency region. Conventionally, thermosetting materials have been developed as materials having a low dielectric loss tangent (see, for example, Patent Documents 2 to 4 below).

Furthermore, materials that allow fine via processing to form high-density wiring are desired, and photosensitive materials have been developed as organic materials that can form small-diameter vias (see, for example, Patent Document 5 below). ).

U.S. Patent Application Publication No. 2011/0221071 JP 2007-87982 A JP 2009-280758 A JP-A-2005-39247 JP 2016-188985 A

In a semiconductor device (organic interposer, FO-WLP, etc.) having a wiring layer having an insulating part having an opening and wiring arranged inside the opening, a plurality of chips are connected at high density using a high-frequency electric signal. In order to do so, a material that is excellent in electrical characteristics in a high-frequency electric signal region and in fine workability is required as a material for forming the insulating portion. However, when using a conventional thermosetting material, which is a material with excellent electrical properties, the laser diameter used for via processing is limited to, for example, 20 μm. On the other hand, conventional photosensitive materials capable of fine via processing tend to have poor electrical properties.

An object of the present disclosure is to provide a photosensitive resin composition that is excellent in electrical properties in a high-frequency electrical signal region and fine workability, and a wiring layer and a semiconductor device using the same.

A photosensitive resin composition according to the present disclosure is a photosensitive resin composition for forming the insulating portion in a wiring layer including an insulating portion having an opening and wiring disposed inside the opening, , a polyimide that is a reaction product of a tetracarboxylic dianhydride and a diamine, wherein the diamine is 1,6-hexamethylenediamine, 1,7-heptamethylenediamine, 1,8-octamethylenediamine, 1, 9-nonamethylenediamine, 2-methyl-1,8-octamethylenediamine, 1,10-decamethylenediamine, 1,11-undecamethylenediamine, 1,12-dodecamethylenediamine, 1,13-tridecamethylene At least selected from the group consisting of diamine, 1,16-hexadecamethylenediamine, 1,18-octadecamethylenediamine, 2,2,4-trimethylhexamethylenediamine, and 2,4,4-trimethylhexamethylenediamine Contains 10 to 80 mol % of one kind.

The photosensitive resin composition according to the present disclosure is excellent in electrical properties in a high frequency electrical signal region (eg, 1 to 60 GHz) and fine workability. In particular, the photosensitive resin composition according to the present disclosure can obtain a low dielectric loss tangent as excellent electrical properties. In addition, although a short-wavelength laser may be required to form a small-diameter via using a thermosetting material, the photosensitive resin composition according to the present disclosure can form a via without using a laser. Since it can be formed, it is excellent in cost and productivity in manufacturing the wiring layer.

By the way, materials for connecting a plurality of chips at high density using high-frequency electrical signals are sometimes required to have excellent insulation reliability in addition to electrical properties and fine workability. On the other hand, the photosensitive resin composition according to the present disclosure is excellent in electrical properties, fine workability, and insulation reliability in a high-frequency electrical signal region.

A wiring layer according to the present disclosure includes an insulating portion having an opening, and wiring arranged inside the opening, and the insulating portion contains the above-described photosensitive resin composition or a cured product thereof. A semiconductor device according to the present disclosure includes the wiring layer described above.

According to the present disclosure, it is possible to provide a photosensitive resin composition that is excellent in electrical properties in a high-frequency electrical signal region and fine workability, and a wiring layer and a semiconductor device using the same. Further, according to the present disclosure, it is possible to provide a photosensitive resin composition excellent in electrical properties in a high-frequency electric signal region, fine workability, and insulation reliability, and a wiring layer and a semiconductor device using the same.

FIG. 1 is a schematic cross-sectional view of a semiconductor package having an organic interposer. FIG. 2 is a schematic cross-sectional view of an organic interposer. FIGS. 3(a) to 3(c) are diagrams for explaining the manufacturing method of the organic interposer. 4(a) and 4(b) are diagrams illustrating a method for manufacturing an organic interposer. 5(a) and 5(b) are diagrams for explaining a method for manufacturing an organic interposer. 6(a) and 6(b) are diagrams for explaining the method of manufacturing the organic interposer. 7(a) and 7(b) are diagrams for explaining a method for manufacturing an organic interposer. 8(a) and 8(b) are diagrams for explaining a method for manufacturing an organic interposer. 9(a) and 9(b) are diagrams for explaining a method for manufacturing an organic interposer. FIG. 10(a) is a plan view showing the measurement evaluation sample of the example, and FIG. 10(b) is a cross-sectional view taken along line XIb-XIb of FIG. 10(a).

In this specification, a numerical range indicated using "to" indicates a range including the numerical values before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described stepwise in this specification, the upper limit value or lower limit value of the numerical range in one step can be arbitrarily combined with the upper limit value or lower limit of the numerical range in another step. In the numerical ranges described herein, the upper or lower limits of the numerical ranges may be replaced with the values shown in the examples. "A or B" may include either A or B, or may include both. The materials exemplified in this specification can be used singly or in combination of two or more unless otherwise specified. The content of each component in the composition means the total amount of the plurality of substances present in the composition unless otherwise specified when there are multiple substances corresponding to each component in the composition. "Layer" and "film" include not only a shape structure formed over the entire surface but also a shape structure formed partially when viewed as a plan view. The term "process" is included in the term not only as an independent process, but also as long as the intended purpose of the process is achieved, even if the process is not clearly distinguishable from other processes.

Hereinafter, embodiments of the present disclosure will be described in detail. However, the present disclosure is not limited to the following embodiments, and various modifications can be made within the scope of the gist of the present disclosure. In the following description, the same or corresponding parts are denoted by the same reference numerals, and overlapping descriptions are omitted. In addition, unless otherwise specified, positional relationships such as up, down, left, and right are based on the positional relationships shown in the drawings. Furthermore, the dimensional ratios of the drawings are not limited to the illustrated ratios.

The wiring layer according to the present embodiment includes an insulating portion having an opening and wiring arranged inside the opening, and the insulating portion contains the photosensitive resin composition according to the present embodiment or a cured product thereof. . That is, the wiring layer according to this embodiment includes wiring and an insulating portion having an opening in which the wiring is arranged. The wiring layer according to this embodiment may include a plurality of wirings. The insulator may have a plurality of openings. The wiring layer according to this embodiment may include a metal layer (for example, a barrier layer) arranged along the inner wall of the opening.

The wiring layer according to the present embodiment includes an insulating portion having an opening, a first layer including wiring arranged inside the opening, and an insulating portion arranged above and/or below the first layer. and a second layer comprising The insulating portion of the second layer may contain the photosensitive resin composition according to the present embodiment or a cured product thereof. When the insulating portion of the second layer is arranged below the first layer, a bottomed concave portion (for example, a groove portion) may be formed in the laminate of the first layer and the second layer. .

A semiconductor device according to this embodiment includes the wiring layer according to this embodiment. Examples of semiconductor devices include organic interposers and FO-WLPs. A semiconductor package according to this embodiment includes the semiconductor device according to this embodiment and a semiconductor chip mounted on the semiconductor device.

The method for producing a wiring layer according to this embodiment includes a wiring layer forming step of forming wirings in openings of an insulating portion containing the photosensitive resin composition according to this embodiment or a cured product thereof to obtain a wiring layer. The wiring layer manufacturing method according to the present embodiment may include an insulating portion forming step of forming an insulating portion having an opening before the wiring layer forming step. In the insulating part forming step, for example, by exposing and developing a photosensitive resin composition layer containing the photosensitive resin composition according to the present embodiment, an insulation containing a cured product of the photosensitive resin composition and having an opening is formed. get the part

The photosensitive resin composition according to this embodiment is a photosensitive resin composition for forming an insulating portion in a wiring layer including an insulating portion having an opening and wiring arranged inside the opening. The photosensitive resin composition according to the present embodiment contains polyimide (A) (polyimide resin, hereinafter sometimes referred to as "(A) component"), which is a reaction product of tetracarboxylic dianhydride and diamine. and the diamines are 1,6-hexamethylenediamine, 1,7-heptamethylenediamine, 1,8-octamethylenediamine, 1,9-nonamethylenediamine, 2-methyl-1,8-octamethylenediamine, 1 , 10-decamethylenediamine, 1,11-undecamethylenediamine, 1,12-dodecamethylenediamine, 1,13-tridecamethylenediamine, 1,16-hexadecamethylenediamine, 1,18-octadecamethylenediamine , 2,2,4-trimethylhexamethylenediamine, and 10 to 80 mol of at least one diamine selected from the group consisting of 2,4,4-trimethylhexamethylenediamine (hereinafter sometimes referred to as "specific diamine") %include. That is, component (A) is a polyimide obtained by reacting a tetracarboxylic dianhydride with a diamine containing 10 to 80 mol % of a specific diamine. The photosensitive resin composition according to the present embodiment is excellent in electrical properties (for example, dielectric loss tangent) in a high-frequency electrical signal region, fine workability, and insulation reliability. According to the photosensitive resin composition according to the present embodiment, it is possible to obtain a cured product that is excellent in electrical properties (for example, dielectric loss tangent) in a high-frequency electrical signal region, fine workability, and insulation reliability. The cured product according to this embodiment is a cured product of the photosensitive resin composition according to this embodiment.

Polyimide can be obtained, for example, by condensation reaction of tetracarboxylic dianhydride and diamine by a known method. For example, a tetracarboxylic dianhydride and a diamine are mixed in an organic solvent (addition order of each component is arbitrary), and addition reaction is carried out at a reaction temperature of 80° C. or less (preferably 0 to 60° C.). As the reaction progresses, the viscosity of the reaction solution gradually increases, and polyamic acid, which is a precursor of polyimide, can be produced.

The tetracarboxylic dianhydride is not particularly limited, and may be a tetracarboxylic dianhydride represented by the following general formula (1), a tetracarboxylic dianhydride represented by the following formula (2), or the following formula ( 3) Tetracarboxylic dianhydride, pyromellitic dianhydride, 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 2,2′,3,3′-biphenyltetracarboxylic dianhydride Carboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 1,1-bis ( 2,3-dicarboxyphenyl)ethane dianhydride, 1,1-bis(3,4-dicarboxyphenyl)ethane dianhydride, bis(2,3-dicarboxyphenyl)methane dianhydride, bis(3 ,4-dicarboxyphenyl)methane dianhydride, bis(3,4-dicarboxyphenyl)sulfone dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, bis(3,4-di carboxyphenyl)ether dianhydride, benzene-1,2,3,4-tetracarboxylic dianhydride, 3,4,3',4'-benzophenonetetracarboxylic dianhydride, 2,3,2', 3'-benzophenonetetracarboxylic dianhydride, 3,3,3',4'-benzophenonetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 1,4,5 ,8-naphthalenetetracarboxylic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 1,2,4,5-naphthalenetetracarboxylic dianhydride, 2,6-dichloronaphthalene- 1,4,5,8-tetracarboxylic dianhydride, 2,7-dichloronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 2,3,6,7-tetrachloronaphthalene-1 ,4,5,8-tetracarboxylic dianhydride, phenanthrene-1,8,9,10-tetracarboxylic dianhydride, pyrazine-2,3,5,6-tetracarboxylic dianhydride, thiophene- 2,3,5,6-tetracarboxylic dianhydride, 2,3,3',4'-biphenyltetracarboxylic dianhydride, 3,4,3',4'-biphenyltetracarboxylic dianhydride , 2,3,2′,3′-biphenyltetracarboxylic dianhydride, bis(3,4-dicarboxyphenyl)dimethylsilane dianhydride, bis(3,4-dicarboxyphenyl)methylphenylsilane dianhydride bis(3,4-dicarboxyphenyl)diphenylsilane dianhydride, 1,4-bis(3,4-dicarboxyphenyldimethylsilyl)benzene dianhydride, 1,3-bis(3,4-di Carboxyphenyl)-1,1,3,3-tetramethyldicyclohexane dianhydride, p-phenylenebis(trimellitate anhydride), ethylenetetracarboxylic dianhydride, 1,2,3,4-butanetetracarboxylic acid dianhydride, decahydronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7-hexahydronaphthalene-1,2,5 ,6-tetracarboxylic dianhydride, cyclopentane-1,2,3,4-tetracarboxylic dianhydride, pyrrolidine-2,3,4,5-tetracarboxylic dianhydride, 1,2,3 ,4-cyclobutanetetracarboxylic dianhydride, bis(exo-bicyclo[2,2,1]heptane-2,3-dicarboxylic dianhydride, bicyclo-[2,2,2]-oct-7-ene -2,3,5,6-tetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis[4-(3,4-dicarboxy Phenyl)phenyl]propane dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, 2,2-bis[4-(3,4-dicarboxyphenyl)phenyl]hexa fluoropropane dianhydride, 4,4′-bis(3,4-dicarboxyphenoxy)diphenylsulfide dianhydride, 1,4-bis(2-hydroxyhexafluoroisopropyl)benzenebis(trimellitic anhydride), 1,3-bis(2-hydroxyhexafluoroisopropyl)benzenebis(trimellitic anhydride), 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid dianhydride, tetrahydrofuran-2,3,4,5-tetracarboxylic dianhydride, and the like. From the viewpoint of further improving various properties of the photosensitive resin composition, it is preferable that the tetracarboxylic dianhydride is recrystallized and purified with acetic anhydride. A tetracarboxylic dianhydride can be used individually by 1 type or in combination of 2 or more types.

［式中、ａは２～２０の整数を示す。］

[In the formula, a represents an integer of 2 to 20. ]

The tetracarboxylic dianhydride represented by the general formula (1) can be synthesized, for example, from trimellitic anhydride monochloride and a corresponding diol, and specific examples include 1,2-(ethylene ) bis(trimellitate anhydride), 1,3-(trimethylene)bis(trimellitate anhydride), 1,4-(tetramethylene)bis(trimellitate anhydride), 1,5-(pentamethylene)bis(trimellitate anhydride) ), 1,6-(hexamethylene)bis(trimellitate anhydride), 1,7-(heptamethylene)bis(trimellitate anhydride), 1,8-(octamethylene)bis(trimellitate anhydride), 1,9 -(nonamethylene)bis(trimellitate anhydride), 1,10-(decamethylene)bis(trimellitate anhydride), 1,12-(dodecamethylene)bis(trimellitate anhydride), 1,16-(hexadecamethylene)bis (trimellitate anhydride), 1,18-(octadecamethylene)bis(trimellitate anhydride) and the like.

In addition, the tetracarboxylic dianhydride is a tetracarboxylic dianhydride represented by the above formula (2) from the viewpoint of easily imparting good solubility in a solvent and moisture resistance reliability, and the above formula (3 ) represented by tetracarboxylic dianhydride (4,4'-(4,4'-isopropylidenediphenoxy)bis(phthalic dianhydride)) can contain at least one selected from the group consisting of .

Diamines for obtaining component (A) include 1,6-hexamethylenediamine, 1,7-heptamethylenediamine, 1,8-octamethylenediamine, 1,9-nonamethylenediamine, 2-methyl-1,8 -octamethylenediamine, 1,10-decamethylenediamine, 1,11-undecamethylenediamine, 1,12-dodecamethylenediamine, 1,13-tridecamethylenediamine, 1,16-hexadecamethylenediamine, 1, It contains at least one specific diamine selected from the group consisting of 18-octadecamethylenediamine, 2,2,4-trimethylhexamethylenediamine, and 2,4,4-trimethylhexamethylenediamine. The diamine preferably contains 1,12-dodecamethylenediamine from the viewpoint of easily obtaining excellent electrical properties, fine workability and insulation reliability. The diamine preferably contains 1,6-hexamethylenediamine from the viewpoint of easily obtaining excellent electrical properties, fine workability and insulation reliability.

The diamine preferably further contains siloxane diamine from the viewpoint of excellent compatibility between the polyimide and other components. That is, the polyimide is preferably a polyimide obtained by reacting a tetracarboxylic dianhydride, a specific diamine, and a siloxane diamine (a reaction product of a tetracarboxylic dianhydride, a specific diamine, and a siloxane diamine).

The siloxane diamine preferably contains a compound represented by the following general formula (4) from the viewpoint of better compatibility between the polyimide and other components.

［式中、Ｑ^１及びＱ^６は、各々独立に、炭素数１～５のアルキレン基、又は、置換基を有してもよいフェニレン基を示し、Ｑ^２、Ｑ^３、Ｑ^４及びＱ^５は、各々独立に、炭素数１～５のアルキル基、フェニル基又はフェノキシ基を示し、ｂは１～５の整数を示す。］

[In the formula, Q ¹ and Q ⁶ each independently represents an alkylene group having 1 to 5 carbon atoms or a phenylene group which may have a substituent, and Q ² , Q ³ , Q ⁴ and Q ⁵ Each independently represents an alkyl group having 1 to 5 carbon atoms, a phenyl group or a phenoxy group, and b represents an integer of 1 to 5. ]

Specific examples of siloxane diamines include 1,1,3,3-tetramethyl-1,3-bis(4-aminophenyl)disiloxane, 1,1, 3,3-tetraphenoxy-1,3-bis(4-aminoethyl)disiloxane, 1,1,3,3-tetraphenyl-1,3-bis(2-aminoethyl)disiloxane, 1,1, 3,3-tetraphenyl-1,3-bis(3-aminopropyl)disiloxane, 1,1,3,3-tetramethyl-1,3-bis(2-aminoethyl)disiloxane, 1,1, 3,3-tetramethyl-1,3-bis(3-aminopropyl)disiloxane, 1,1,3,3-tetramethyl-1,3-bis(3-aminobutyl)disiloxane, 1,3- Dimethyl-1,3-dimethoxy-1,3-bis(4-aminobutyl)disiloxane and the like, and compounds in which b is 2 include 1,1,3,3,5,5-hexamethyl-1, 5-bis(4-aminophenyl)trisiloxane, 1,1,5,5-tetraphenyl-3,3-dimethyl-1,5-bis(3-aminopropyl)trisiloxane, 1,1,5,5 -tetraphenyl-3,3-dimethoxy-1,5-bis(4-aminobutyl)trisiloxane, 1,1,5,5-tetraphenyl-3,3-dimethoxy-1,5-bis(5-amino pentyl)trisiloxane, 1,1,5,5-tetramethyl-3,3-dimethoxy-1,5-bis(2-aminoethyl)trisiloxane, 1,1,5,5-tetramethyl-3,3 -dimethoxy-1,5-bis(4-aminobutyl)trisiloxane, 1,1,5,5-tetramethyl-3,3-dimethoxy-1,5-bis(5-aminopentyl)trisiloxane, 1, 1,3,3,5,5-hexamethyl-1,5-bis(3-aminopropyl)trisiloxane, 1,1,3,3,5,5-hexaethyl-1,5-bis(3-aminopropyl) ) trisiloxane, 1,1,3,3,5,5-hexapropyl-1,5-bis(3-aminopropyl)trisiloxane, and the like. Siloxanediamine can be used individually by 1 type or in combination of 2 or more types.

Commercial products of siloxane diamine include "PAM-E" (amino group equivalent weight 130 g/mol), "KF-8010" (amino group equivalent weight 430 g/mol), and "X-22-161A" having amino groups at both ends. (amino group equivalent weight 800 g / mol), "X-22-161B" (amino group equivalent weight 1500 g / mol), "KF-8012" (amino group equivalent weight 2200 g / mol), "KF-8008" (amino group equivalent weight 5700 g / mol), “X-22-9409” (amino group equivalent weight 700 g / mol, side chain phenyl type), “X-22-1660B-3” (amino group equivalent weight 2200 g / mol, side chain phenyl type) (above, Shin-Etsu Chemical Industry Co., Ltd.), "BY-16-853U" (amino group equivalent 460 g / mol), "BY-16-853" (amino group equivalent 650 g / mol), "BY-16-853B" (amino group equivalent 2200 g/mol) (manufactured by Dow Corning Toray Co., Ltd.). Among these, "PAM-E", "KF-8010", "X-22-161A", "BY-16-853U" and "BY-16-853" are preferable from the viewpoint of easily excellent dielectric properties. On the other hand, "KF-8010", "X-22-161A" and "BY-16-853" are preferable from the viewpoint of easily excellent varnish compatibility.

Other diamines used as raw materials for polyimide are not particularly limited, and o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, 3,3′-diaminodiphenyl ether, 3,4′-diaminodiphenyl ether, 4, 4'-diaminodiphenyl ether, 3,3'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether methane, bis(4-amino-3,5-dimethylphenyl)methane, bis(4- amino-3,5-diisopropylphenyl)methane, 3,3′-diaminodiphenyldifluoromethane, 3,4′-diaminodiphenyldifluoromethane, 4,4′-diaminodiphenyldifluoromethane, 3,3′-diaminodiphenylsulfone, 3,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 3,3'- Diaminodiphenyl ketone, 3,4'-diaminodiphenyl ketone, 4,4'-diaminodiphenyl ketone, 2,2-bis(3-aminophenyl)propane, 2,2'-(3,4'-diaminodiphenyl)propane , 2,2-bis(4-aminophenyl)propane, 2,2-bis(3-aminophenyl)hexafluoropropane, 2,2-(3,4′-diaminodiphenyl)hexafluoropropane, 2,2- bis(4-aminophenyl)hexafluoropropane, 1,3-bis(3-aminophenoxy)benzene, 1,4-bis(3-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 3,3′-(1,4-phenylenebis(1-methylethylidene))bisaniline, 3,4′-(1,4-phenylenebis(1-methylethylidene))bisaniline, 4,4′-(1, 4-Phenylenebis(1-methylethylidene))bisaniline, 2,2-bis(4-(3-aminophenoxy)phenyl)propane, 2,2-bis(4-(3-aminophenoxy)phenyl)hexafluoropropane , 2,2-bis(4-(4-aminophenoxy)phenyl)hexafluoropropane, bis(4-(3-aminoethoxy)phenyl)sulfide, bis(4-(4-aminoethoxy)phenyl)sulfide, bis (4-(3-aminoethoxy)phenyl)sulfone, bis(4-(4-aminoethoxy)phenyl)sulfone, 3,3'-dihydroxy-4,4'-diaminobiphenyl, 3,5-diaminobenzoic acid, etc. aromatic diamines, 1,3-bis(aminomethyl)cyclohexane, 2,2-bis(4-aminophenoxyphenyl)propane, aliphatic ether diamines represented by the following general formula (5), the following general formula (6 ), diamines having carboxyl groups and/or hydroxyl groups in the molecule, and the like. These diamines can be used singly or in combination of two or more.

［式中、Ｑ^７、Ｑ^８及びＱ^９は、各々独立に炭素数１～１０のアルキレン基を示し、ｃは、２～８０の整数を示す。］

[In the formula, Q ⁷ , Q ⁸ and Q ⁹ each independently represents an alkylene group having 1 to 10 carbon atoms, and c represents an integer of 2 to 80. ]

［式中、ｄは５～２０の整数を示す。］

[In the formula, d represents an integer of 5 to 20. ]

The diamine contains 10 to 80 mol% of the specific diamine based on the total amount of diamines for obtaining the component (A) (all diamines. The total amount of the specific diamine and diamines other than the specific diamine. The same shall apply hereinafter.). The ratio of the specific diamine is preferably 30 mol % or more, more preferably 40 mol % or more, and even more preferably 45 mol % or more, from the viewpoint of reducing moisture absorption and easily obtaining excellent electrical properties (low dielectric loss tangent). The ratio of the specific diamine is preferably 75 mol % or less, more preferably 70 mol % or less, and even more preferably 60 mol % or less, from the viewpoint of increasing the glass transition temperature and easily increasing the compatibility with other components of the polyimide. When multiple diamines are used as the specific diamines, the ratio of the specific diamines mentioned above is the ratio of the total amount of the multiple specific diamines.

The diamine preferably contains siloxane diamine in the following proportions based on the total amount of diamine (total diamine). The ratio of siloxane diamine is preferably 5 mol % or more, more preferably 10 mol % or more, still more preferably 15 mol % or more, and particularly preferably 20 mol % or more, from the viewpoint of easily having excellent compatibility with other components of the polyimide. The proportion of siloxane diamine is preferably 50 mol % or less, more preferably less than 50 mol %, still more preferably 40 mol % or less, and particularly preferably 30 mol % or less, from the viewpoint of easily improving adhesion to metal. From these points of view, the ratio of siloxane diamine is preferably 5 to 50 mol %.

The ratio of the specific diamine is preferably within the following ranges per 1.0 mol of the tetracarboxylic dianhydride. The ratio of the specific diamine is preferably 0.1 mol or more, more preferably 0.3 mol or more, still more preferably 0.4 mol or more, and particularly preferably 0.5 mol or more, from the viewpoint of easily having excellent compatibility with other components of the polyimide. The ratio of the specific diamine is preferably 1.0 mol or less, more preferably less than 1.0 mol, still more preferably 0.9 mol or less, and particularly preferably 0.8 mol or less, from the viewpoint of easily improving adhesion to metal.

The proportion of diamines (total diamines) is preferably in the following ranges per 1.0 mol of tetracarboxylic dianhydride. The ratio of diamine is preferably 0.5 mol or more, more preferably 0.7 mol or more, still more preferably 0.8 mol or more, and particularly preferably 0.9 mol or more, from the viewpoint of easily increasing the molecular weight of the polyimide. The ratio of diamine is preferably 1.0 mol or less, particularly preferably less than 1.0 mol, from the viewpoint of easily suppressing the reaction between the polyimide terminal and other components.

Acid anhydrides other than tetracarboxylic dianhydride can be used as raw materials for polyimide. For example, when synthesizing polyimide, monofunctional acid anhydrides such as compounds represented by the following formulas (7), (8) or (9), monofunctional amines such as m-aminophenol, etc. are added to the condensation reaction solution. A functional group other than an acid anhydride or a diamine can be introduced into the terminal of the polymer by the injection. In addition, this makes it possible to lower the molecular weight of the polymer and improve the developability at the time of pattern formation. As the monofunctional acid anhydride, the compound represented by the formula (9) is preferable from the viewpoint of excellent dielectric properties.

The weight average molecular weight of the polyimide is preferably 20,000 or more, more preferably 25,000 or more, and even more preferably 30,000 or more, from the viewpoint of easily obtaining excellent coating film formability. When the weight average molecular weight is 25,000 or more, it is easy to suppress pinholes after coating. When the weight average molecular weight is 30,000 or more, the toughness of the cured product is excellent. The weight average molecular weight of polyimide is preferably 80,000 or less, more preferably 70,000 or less, from the viewpoint of easily obtaining excellent resolution. From these points of view, the polyimide preferably has a weight average molecular weight of 20,000 to 80,000. The weight-average molecular weight can be obtained as a weight-average molecular weight measured in terms of polystyrene using high-performance liquid chromatography (manufactured by Shimadzu Corporation, trade name “C-R4A”). For the measurement, for example, the following conditions can be used.
Detector: LV4000 UV Detector (manufactured by Hitachi, Ltd., trade name)
Pump: L6000 Pump (manufactured by Hitachi, Ltd., trade name)
Column: Gelpack GL-S300MDT-5 (2 in total) (manufactured by Hitachi Chemical Co., Ltd., trade name)
Eluent: THF/DMF = 1/1 ₍ volume ratio) + LiBr (0.03 mol/L) + _H3PO4 (0.06 mol/L)
Flow rate: 1 mL/min

The glass transition temperature of the polyimide is preferably 220° C. or less from the viewpoint of easily suppressing a decrease in the storage stability of the varnish, and from the viewpoint of easily suppressing an increase in the dielectric loss tangent due to an increase in the imide group concentration. , 200° C. or less is more preferable. If the glass transition temperature is 200° C. or lower, the dielectric loss tangent is likely to be reduced. The glass transition temperature of polyimide is preferably 60° C. or higher, more preferably 80° C. or higher, and even more preferably 100° C. or higher, from the viewpoint of easily suppressing an excessive increase in tack after coating. When the glass transition temperature is 80°C or higher, it is easy to improve the toughness of the cured product after curing. When the glass transition temperature is 100°C or higher, the coefficient of linear expansion can be easily lowered. From these points of view, the glass transition temperature of polyimide is preferably 60 to 220.degree. C., more preferably 60 to 200.degree.

The glass transition temperature can be measured by the following procedure. A sample is prepared by cutting a piece of polyimide having a thickness of 300 μm into a length of 30 mm and a width of 4 mm. Using a dynamic viscoelasticity measuring device manufactured by UBM Co., Ltd., the distance between chucks is 20 mm, the frequency is 10 Hz, and the temperature is measured at a temperature range of 40 to 260 ° C. at a temperature increase rate of 5 ° C./min. You can get the temperature that shows the value.

The photosensitive resin composition according to the present embodiment includes a compound (B) having two or more carbon-carbon double bonds in the molecule (hereinafter sometimes referred to as "(B) component"), and photopolymerization It is preferable to contain an initiator (C) (hereinafter sometimes referred to as "component (C)"). In this case, excellent electrical properties, fine workability and insulation reliability are likely to be obtained.

［式中、Ｒ^１は、芳香環を含む２価の有機基、又は、直鎖、分岐若しくは環状の脂肪族炭化水素を含む２価の有機基を示す。］ Component (B) excludes compounds corresponding to component (A) or component (C). As component (B), bisallylnadiimide represented by the following general formula (10) can be used. R ¹ in formula (10) includes a phenylene group (benzene residue), tolylene (toluene residue), xylylene group (xylene residue), naphthylene (naphthalene residue), a linear, branched or cyclic alkylene group, Alternatively, a mixed group thereof is preferable, and a divalent organic group represented by the following formulas (11-1) to (11-25) is more preferable. e in formula (11-1) represents an integer of 1-10.

[In the formula, R ¹ represents a divalent organic group containing an aromatic ring or a divalent organic group containing a linear, branched or cyclic aliphatic hydrocarbon. ]

As the component (B), a bifunctional or higher functional acrylate compound is preferable from the viewpoint of easily obtaining excellent electrical properties, fine workability and insulation reliability. The bifunctional or higher acrylate compound is not particularly limited as long as it is a compound having two or more acrylic functional groups per molecule, and specific examples thereof include diethylene glycol diacrylate, triethylene glycol diacrylate, and tetraethylene glycol. diacrylate, trimethylolpropane diacrylate, trimethylolpropane triacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, polyethylene glycol diacrylate, ethylene oxide-modified neopentyl glycol acrylate, polypropylene glycol diacrylate, Phenoxyethyl acrylate, tricyclodecane dimethanol diacrylate, ditrimethylolpropane tetraacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, tris(β-hydroxyethyl)isocyanurate triacrylate, the following general formula Bifunctional acrylate represented by (12) and the like can be mentioned, and among them, tricyclodecane dimethanol diacrylate is preferable from the viewpoint of easily having excellent heat resistance and dielectric properties.

［式中、Ｒ^２は、有機基を示し、Ｒ^３及びＲ^４は、それぞれ独立に水素原子又はメチル基を示し、ｍ及びｎは、それぞれ独立に１以上の整数を示す。］

[In the formula, R ² represents an organic group, R ³ and R ⁴ each independently represent a hydrogen atom or a methyl group, and m and n each independently represent an integer of 1 or more. ]

A maleimide compound can be used as the component (B). Maleimide compounds include o-, m- or p-bismaleimidobenzene, 4-bis(p-maleimidocumyl)benzene, 1,4-bis(m-maleimidocumyl)benzene, 4,4-bismaleimidodiphenyl ether. , 4,4-bismaleimidodiphenylmethane, 4,4-bismaleimido-3,3′-dimethyl-diphenylmethane, 4,4-bismaleimidodiphenylsulfone, 4,4-bismaleimidodiphenyl sulfide, 4,4-bismaleimidodiphenyl Ketones, 2'-bis(4-maleimidophenyl)propane, 4-bismaleimidodiphenylfluoromethane, 1,1,1,3,3,3-hexafluoro-2,2-bis(4-maleimidophenyl)propane, etc. is mentioned. A maleimide compound can be used individually by 1 type or in combination of 2 or more types.

The content of component (B) is preferably within the following ranges per 100 parts by mass of component (A). The content of component (B) is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, still more preferably 15 parts by mass or more, and particularly 20 parts by mass or more, from the viewpoint of easily obtaining excellent resolution. preferable. The content of component (B) is preferably 70 parts by mass or less, more preferably 50 parts by mass or less, still more preferably 40 parts by mass or less, and particularly preferably 30 parts by mass or less, from the viewpoint of easily obtaining excellent dielectric properties. . From these points of view, the content of component (B) is preferably 5 to 70 parts by mass.

Component (C) is not particularly limited, but examples include 1,2-octanedione, 1-[4-(phenylthio)-phenyl, 2-(O-benzoyloxime)], ethanone, 1-[9- Oxime ester compounds such as ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime); 2-benzyl-2-dimethylamino-1-(4-morpholino Phenyl)-butanone-1,2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-methyl-1-(4-(methylthio)phenyl)-2 - morpholinopropanone - aromatic ketones such as 1,2,4-diethylthioxanthone, 2-ethylanthraquinone, phenanthrenequinone; benzyl derivatives such as benzyl dimethyl ketal; 2-(o-chlorophenyl)-4,5-diphenylimidazole 2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl)imidazole dimer, 2-(o-fluorophenyl)-4,5-phenylimidazole dimer, 2-(o -Methoxyphenyl)-4,5-diphenylimidazole dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer, 2,4-di(p-methoxyphenyl)-5-phenylimidazole dimers, 2,4,5-triarylimidazole dimers such as 2-(2,4-dimethoxyphenyl)-4,5-diphenylimidazole dimers; 9-phenylacridine, 1,7-bis( 9,9′-acridinyl)heptane and other acridine derivatives; bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, bis(2,4,6,-trimethylbenzoyl)-phenyl Among bisacylphosphine oxides such as phosphine oxides, compounds that are photofaded by UV irradiation can be used. (C) Component can be used individually by 1 type or in combination of 2 or more types.

Component (C) is an oxime ester group represented by the following general formula (13), a compound having a morpholine ring represented by the following general formula (14), and a compound having a morpholine ring represented by the following general formula (14). It preferably contains at least one selected from the group consisting of compounds having a morpholine ring represented by general formula (15).

［式中、Ｒ^５１及びＲ^５２は、それぞれ独立に、水素原子、炭素数１～７のアルキル基、又は、芳香族系炭化水素基を含む有機基を示し、Ｒ^５３は、炭素数１～７のアルキル基、又は、芳香族系炭化水素基を含む有機基を示し、Ｒ^５４及びＲ^５５は、芳香族系炭化水素基を含む有機基を示す。］

[In the formula, R ⁵¹ and R ⁵² each independently represent a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, or an organic group containing an aromatic hydrocarbon group, and R ⁵³ represents a 7 represents an alkyl group or an organic group containing an aromatic hydrocarbon group, and R ⁵⁴ and R ⁵⁵ represent an organic group containing an aromatic hydrocarbon group. ]

The molecular extinction coefficient of component (C) with respect to light with a wavelength of 365 nm is preferably 1000 mL/g·cm or more, more preferably 2000 mL/g·cm or more, from the viewpoint of easily improving sensitivity. The molecular extinction coefficient is obtained by preparing an acetonitrile solution containing 0.001% by mass of a photopolymerization initiator, and measuring this solution with a spectrophotometer (manufactured by Hitachi High-Technologies Corporation, "U-3310" (trade name)). It is obtained by measuring the absorbance using

The content of component (C) is preferably within the following ranges per 100 parts by mass of component (A). The content of component (C) is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, still more preferably 1 part by mass or more, from the viewpoint of easily obtaining excellent resolution, and 3 parts by mass. Part or more is particularly preferred. The content of component (C) is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, still more preferably 7 parts by mass or less, and particularly preferably 5 parts by mass or less, from the viewpoint of easily obtaining excellent heat resistance. . From these points of view, the content of component (C) is preferably 0.1 to 10 parts by mass.

The photosensitive resin composition according to this embodiment may contain a compound having a phenolic hydroxyl group. Examples of compounds having a phenolic hydroxyl group include phenol/formaldehyde condensed novolak resins, cresol/formaldehyde condensed novolac resins, phenol-naphthol/formaldehyde condensed novolak resins, polyhydroxystyrene and polymers thereof, phenol-xylylene glycol condensed resins, cresol- Examples include xylylene glycol condensed resins, phenol-dicyclopentadiene condensed resins, and the like.

The photosensitive resin composition according to this embodiment may contain an adhesion aid. Adhesion aids include silane coupling agents, triazole compounds, tetrazole compounds, and the like. Adhesion aids can be used singly or in combination of two or more.

As the silane coupling agent, a compound having a nitrogen atom is preferable from the viewpoint of easily improving adhesion to metal. Specific examples of silane coupling agents include N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane. Silane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, tris-(trimethoxysilylpropyl ) isocyanurate, 3-ureidopropyltrialkoxysilane, 3-isocyanatopropyltriethoxysilane and the like. The content of the silane coupling agent is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the polyimide, from the viewpoint of the effect of addition, heat resistance, production cost, and the like.

Triazole compounds include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2′-hydroxy-3′,5′-di-tert-amylphenyl)benzotriazole, 2-(2′-hydroxy-5′-tert-octylphenyl)benzotriazole, 2,2′-methylenebis[ 6-(2H-benzotriazol-2-yl)-4-tert-octylphenol], 6-(2-benzotriazolyl)-4-tert-octyl-6′-tert-butyl-4′-methyl-2 , 2′-methylenebisphenol, 1,2,3-benzotriazole, 1-[N,N-bis(2-ethylhexyl)aminomethyl]benzotriazole, carboxybenzotriazole, 1-[N,N-bis(2- ethylhexyl)aminomethyl]methylbenzotriazole, 2,2′-[[(methyl-1H-benzotriazol-1-yl)methyl]imino]bisethanol and the like. Tetrazole compounds include 1H-tetrazole, 5-amino-1H-tetrazole, 5-methyl-1H-tetrazole, 5-phenyl-1H-tetrazole, 1-methyl-5-ethyl-1H-tetrazole, 1-methyl-5 -mercapto-1H-tetrazole, 1-phenyl-5-mercapto-1H-tetrazole, 1-(2-dimethylaminoethyl)-5-mercapto-1H-tetrazole, 2-methoxy-5-(5-trifluoromethyl- 1H-tetrazol-1-yl)-benzaldehyde, 4,5-di(5-tetrazolyl)-[1,2,3]triazole, 1-methyl-5-benzoyl-1H-tetrazole and the like. The content of the triazole compound and/or the tetrazole compound is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the polyimide, from the viewpoint of the effect of addition, heat resistance, and excellent production cost.

The photosensitive resin composition according to this embodiment may contain a radical polymerization agent as a curing agent. Radical polymerization agents include acetylcyclohexylsulfonyl peroxide, isobutyryl peroxide, benzoyl peroxide, octanoyl peroxide, acetyl peroxide, dicumyl peroxide, cumene hydroperoxide, azobisisobutyronitrile and the like. . The content of the radical polymerization agent is preferably 0.01 to 1.0 parts by weight per 100 parts by weight of component (A).

The photosensitive resin composition according to this embodiment may contain an ion scavenger. By adsorbing ionic impurities in the insulating portion with the ion scavenger, it is easy to improve insulation reliability during moisture absorption. Examples of ion scavengers include triazine thiol compounds, phenol-based reducing agents, and other compounds known as copper damage inhibitors for preventing ionization and leaching of copper; bismuth-based, antimony-based, magnesium-based, and aluminum-based compounds. , zirconium-based, calcium-based, titanium-based, tin-based, and powdery inorganic compounds such as mixtures thereof.

As the ion scavenger, inorganic ion scavenger manufactured by Toagosei Co., Ltd. (trade name: IXE-300 (antimony system), IXE-500 (bismuth system), IXE-600 (antimony, bismuth system), IXE-700 (magnesium and aluminum mixed system), IXE-800 (zirconium system), IXE-1100 (calcium system), etc.). An ion trapping agent can be used individually by 1 type or in combination of 2 or more types. The content of the ion trapping agent is preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the polyimide, from the viewpoint of the effect of addition, heat resistance, production cost, and the like.

The photosensitive resin composition according to the present embodiment may contain a filler in order to impart low hygroscopicity and/or low moisture permeability. Filler constituent materials include alumina, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, aluminum nitride, crystalline silica, and amorphous Inorganic fillers such as silica, boron nitride, titania, glass, iron oxide and ceramics; and organic fillers such as carbon and rubber fillers.

The above fillers can be used properly according to the desired function. An inorganic filler, an organic filler, or the like can be used as the filler. The inorganic filler can be added for the purpose of imparting thermal conductivity, low thermal expansion, low hygroscopicity, etc. to the insulating portion. The organic filler can be added for the purpose of imparting toughness or the like to the insulating portion. A filler can be used individually by 1 type or in combination of 2 or more types. Among them, inorganic fillers are preferable from the viewpoint of being able to impart the thermal conductivity, low moisture absorption characteristics, insulating properties, etc. required for the insulating part. At least one filler selected from the group consisting of silica filler and alumina filler is more preferable from the viewpoint of easily imparting high adhesive strength.

The filler preferably has an average particle size of 5 µm or less and a maximum particle size of 20 µm or less, more preferably an average particle size of 1 µm or less and a maximum particle size of 5 µm or less. When the average particle size is 5 µm or less and the maximum particle size is 20 µm or less, excellent resolution is likely to be obtained. The lower limits of the average particle size and the maximum particle size are not particularly limited, but may be 0.001 μm or more.

Examples of the method for measuring the average particle size and maximum particle size of the filler include a method of measuring the particle size of any number of fillers using a scanning electron microscope (SEM). As a measuring method using SEM, for example, a method of preparing a sample by curing a photosensitive resin composition, cutting the central portion of the sample, and observing the cross section with SEM can be mentioned. At this time, it is preferable that the existence probability of the filler having a particle diameter of 10 μm or less is 80% or more of all the fillers.

The photosensitive resin composition according to the present embodiment can contain an antioxidant for imparting storage stability, preventing electromigration, preventing corrosion of metal conductor circuits, and the like. Examples of antioxidants include benzophenone-based, benzoate-based, hindered amine-based, benzotriazole-based, and phenol-based antioxidants. The content of the antioxidant is preferably from 0.01 to 10 parts by mass per 100 parts by mass of the component (A) from the viewpoints of the effects of addition, heat resistance, cost and the like.

The dielectric constant of the insulating portion at 10 GHz is preferably 3.0 or less from the viewpoint of suppressing crosstalk between wirings, and is 2.8 or less from the viewpoint of further improving the reliability of electrical signals. is more preferable. Further, the dielectric loss tangent at 10 GHz is preferably 0.01 or less, more preferably 0.008 or less, still more preferably 0.007 or less, and particularly preferably 0.005 or less. preferable. In the measurement of the dielectric constant and dielectric loss tangent, the photosensitive resin composition was exposed under the conditions of 200 mJ/cm ² , then heated under the conditions of 100 ° C. for 2 minutes, and further heated under the conditions of 220 ° C. for 1 hour. A test piece obtained by cutting a cured product of a photosensitive resin composition having a thickness of 300 μm obtained by curing to a length of 60 mm and a width of 2 mm and then vacuum drying at 30 ° C. for 6 hours can be used. . The dielectric loss tangent can be calculated from the resonance frequency obtained at 10 GHz and the unloaded Q value. Measurement of dielectric loss tangent can be performed at a temperature of 25°C using a vector-type network analyzer E8364B manufactured by Keysight Technologies, CP531 (10 GHz resonator) and CPMA-V2 (program) manufactured by Kanto Denshi Applied Development Co., Ltd. .

A semiconductor package having an organic interposer, which is an example of a semiconductor device, and a method for manufacturing the same will be described below with reference to FIGS.

FIG. 1 is a schematic cross-sectional view of a semiconductor package having an organic interposer. The organic interposer is preferably used in a package form that requires an interposer in which different types of chips are mixed.

As shown in FIG. 1, in a semiconductor package 100, semiconductor chips 2A and 2B are mounted on an organic interposer (semiconductor device) 10 provided on a substrate 1. As shown in FIG. The semiconductor chips 2A and 2B are fixed on the organic interposer 10 by corresponding underfills 3A and 3B, respectively, and are electrically connected to each other via surface wiring 16 provided inside the organic interposer 10. As shown in FIG. The substrate 1 is a sealing body formed by sealing semiconductor chips 2C, 2D and electrodes 5A, 5B with an insulating material 4. As shown in FIG. The semiconductor chips 2C and 2D in the substrate 1 can be connected to an external device through electrodes exposed from the insulating material 4. FIG. The electrodes 5A and 5B function, for example, as conductive paths for electrically connecting the organic interposer 10 and an external device to each other.

Each of the semiconductor chips 2A to 2D includes a graphic processing unit (GPU), a volatile memory such as a DRAM (Dynamic Random Access Memory) or an SRAM (Static Random Access Memory), a nonvolatile memory such as a flash memory, Examples include RF chips, silicon photonics chips, MEMS (Micro Electro Mechanical Systems), and sensor chips. The semiconductor chips 2A-2D may have TSVs. As each of the semiconductor chips 2A to 2D, for example, a stack of semiconductor elements can be used. In this case, semiconductor elements stacked using TSV can be used. The thickness of the semiconductor chips 2A, 2B is, for example, 200 μm or less. From the viewpoint of thinning the semiconductor package 100, the thickness of the semiconductor chips 2A and 2B is preferably 100 μm or less. Moreover, the thickness of the semiconductor chips 2A and 2B is preferably 30 μm or more from the viewpoint of handling.

The underfills 3A, 3B are, for example, capillary underfills (CUF), mold underfills (MUF), paste underfills (NCP), film underfills (NCF), or photosensitive underfills. Each of the underfills 3A and 3B is mainly composed of liquid curable resin (for example, epoxy resin). Moreover, the insulating material 4 is, for example, a curable resin having insulating properties.

Next, the details of the organic interposer 10 will be described with reference to FIG. The organic interposer 10 is an organic substrate that supports a semiconductor element or the like. A substrate manufactured by thermally curing a sealing material, a substrate in which a chip is sealed or embedded, and the like. The shape of the organic interposer 10 corresponds to the shape of the substrate 11, which will be described later, and may be wafer-like (substantially circular in plan view) or panel-like (substantially rectangular in plan view).

In FIG. 2, an organic interposer 10 provided on a substrate 11 (corresponding to the substrate 1 in FIG. 1) is an insulating laminate (for example, an organic insulating laminate) 12 including a plurality of insulating layers (for example, organic insulating layers). , a plurality of wirings 13 arranged in the insulating laminate 12 , a barrier metal film 14 covering the sides and bottom of the wirings 13 , a through wiring 15 penetrating the insulating laminate 12 , and the surface of the insulating laminate 12 . and a surface wiring 16 formed in the vicinity thereof.

The substrate 11 is a support that supports the organic interposer 10 . The shape of the substrate 11 in plan view is, for example, circular or rectangular. If circular, the substrate 11 has a diameter of, for example, 200-450 mm. In the case of a rectangular shape, the length of one side of the substrate 11 is, for example, 300 to 700 mm.

The substrate 11 is, for example, a silicon substrate, a glass substrate, or a peelable copper foil. The substrate 11 may be, for example, a build-up substrate, a substrate for wafer level packaging, a coreless substrate, a substrate made by thermally curing a sealing material, or a substrate with chips sealed or embedded. When a silicon substrate, a glass substrate, or the like is used as the substrate 11, a temporary fixing layer (not shown) for temporarily fixing the organic interposer 10 and the substrate 11 may be provided. In this case, the substrate 11 can be easily separated from the organic interposer 10 by removing the temporary fixing layer. The peelable copper foil is a laminate in which a support, a peeling layer and a copper foil are layered in order. In the peelable copper foil, the support corresponds to the substrate 11 , and the copper foil corresponds to the material of some copper wiring included in the through wiring 15 .

The insulating laminate 12 includes an insulating layer (first insulating layer) 21 having a plurality of grooves 21a in which corresponding wirings 13 are arranged, and an insulating layer (second insulating layer) laminated on the insulating layer 21 so as to embed the wirings 13 therein. insulating layer) 22. Further, the insulating laminate 12 is provided with a plurality of openings 12a in which the through wirings 15 are provided.

The plurality of grooves 21 a are provided on the surface of the insulating layer 21 opposite to the substrate 11 . Each of the grooves 21a has a substantially rectangular shape in a cross section along a direction perpendicular to the extending direction of the grooves 21a. The inner surface of the groove portion 21a has a side surface and a bottom surface. Also, the plurality of grooves 21a have a predetermined line width L and a predetermined space width S. As shown in FIG. Each of the line width L and the space width S is, for example, 0.5-10 μm, preferably 0.5-5 μm, more preferably 2-5 μm. From the viewpoint of realizing high-density transmission of the organic interposer 10, the line width L is preferably 1 to 5 μm. The line width L and the space width S may be set to be the same as each other, or may be set to be different from each other. The line width L corresponds to the width of the groove portion 21a in the direction orthogonal to the extending direction of the groove portion 21a in plan view. The space width S corresponds to the distance between adjacent grooves 21a. The depth of the groove portion 21a corresponds to, for example, the thickness of the insulating layer 24, which will be described later.

The insulating layer 21 is provided between the substrate 11 and the insulating layer 22 . The insulating layer 21 includes an insulating layer (third insulating layer) 23 located on the substrate 11 side and an insulating layer (fourth insulating layer, insulating section) 24 located on the insulating layer 22 side. A portion of the insulating layer 24 is provided with a plurality of openings (through holes) corresponding to the groove portions 21a. The surface of the insulating layer 23 exposed through these openings constitutes the bottom surface of the inner surface of the groove portion 21a. Further, each side surface of the inner surface of the groove portion 21a is constituted by an insulating layer 24. As shown in FIG. The wiring 13 , the barrier metal film 14 and the insulating layer 24 constitute a wiring layer 25 .

The thicknesses of the insulating layers 23 and 24 are, for example, 0.5 to 10 μm, respectively. Therefore, the thickness of the insulating layer 21 is, for example, 1 to 20 μm. When the thickness of the insulating layer 21 is 1 μm or more, the insulating layer 21 contributes to stress relaxation of the insulating laminate 12 and the temperature cycle resistance of the insulating laminate 12 can be improved. By setting the thickness of the insulating layer 21 to 20 μm or less, warping of the insulating laminate 12 can be suppressed, and, for example, wiring and the like can be easily exposed when the insulating laminate 12 is ground. The thickness of the insulating layer 21 is preferably 15 μm or less, more preferably 10 μm or less, from the viewpoint of forming the wiring 13 with a width of 3 μm or less by performing exposure and development.

Each of the insulating layer 21 and the insulating layer 22 in the insulating laminate 12 is liquid or film-like, for example. A film-like material (insulating material) is preferable from the viewpoint of the flatness of the insulating layer and the manufacturing cost. In this case, for example, even if the surface roughness of the substrate 11 is 300 μm or more, the surface roughness of the insulating laminate 12 can be reduced. Moreover, it is preferable that the film-like insulating material can be laminated at 40 to 120.degree. When the temperature at which lamination is possible is 40° C. or higher, it is possible to prevent the insulating material from becoming too tacky (adhesive) at room temperature and to maintain good handleability. Since the temperature at which lamination is possible is 120° C. or less, the occurrence of warping in the insulating laminate 12 can be suppressed.

Each of the insulating layer 21 and the insulating layer 22 in the insulating laminate 12 contains a curable insulating material. A photosensitive insulating material (photosensitive insulating resin) can be used as the insulating material from the viewpoint of ease of processing and processing accuracy. The insulating layer 24 contains the photosensitive resin composition according to this embodiment or a cured product thereof. The insulating layer 22 and/or the insulating layer 23 may contain the photosensitive resin composition according to this embodiment or a cured product thereof. The photosensitive resin composition is preferably a negative photosensitive resin composition from the viewpoint of heat resistance and ease of handling. The photosensitive resin composition is preferably soluble in cyclopentanone or a 2.38% by mass tetramethylammonium aqueous solution.

The plurality of wirings 13 are provided in the corresponding grooves 21a and function as conductive paths inside the organic interposer 10, as described above. Therefore, the width of the wiring 13 substantially matches the line width L of the groove 21a, and the interval between adjacent wirings 13 substantially matches the space width S of the groove 21a. The wiring 13 preferably contains a metal material having high conductivity from the viewpoint of satisfactorily functioning as a conductive path. Examples of highly conductive metal materials include copper, aluminum, and silver. These metal materials tend to diffuse into the insulating laminate 12 when heated. The metal material contained in the wiring 13 is preferably copper from the viewpoint of conductivity and cost.

The barrier metal film 14 is a metal film provided so as to partition the wiring 13 and the insulating layer 21, and is provided between the wiring 13 and the inner surface of the groove portion 21a. For this reason, the barrier metal film 14 is provided so as to partition the wiring 13 and the inner surface of the groove portion 21a (that is, the insulating layer 21).

The barrier metal film 14 is a conductive film for preventing the metal material in the wiring 13 from diffusing into the insulating layer 21, and is formed along the inner surface of the trench 21a. The barrier metal film 14 contains, for example, at least one of titanium, nickel, palladium, chromium, tantalum, tungsten, and gold as a metal material that is difficult to diffuse into the insulating layer. The barrier metal film 14 is preferably a titanium film or an alloy film containing titanium from the viewpoint of adhesion to the inner surface of the groove 21a. From the viewpoint of forming the barrier metal film 14 by sputtering, the barrier metal film 14 is a titanium film, a tantalum film, a tungsten film, a chromium film, or an alloy film containing at least one of titanium, tantalum, tungsten and chromium. Preferably.

The thickness of the barrier metal film 14 is less than half the width of the groove 21a and less than the depth of the groove 21a, eg, 0.001 to 0.5 μm. The thickness of the barrier metal film 14 is preferably 0.01 to 0.5 μm from the viewpoint of preventing the metal material from diffusing in the wiring 13 . The thickness of the barrier metal film 14 is preferably 0.001 to 0.3 μm from the viewpoint of flatness of the barrier metal film 14 and increasing the amount of current flowing through the wiring 13 . From the above, it is particularly preferable that the thickness of the barrier metal film 14 is 0.01 to 0.3 μm.

The through wiring 15 is wiring embedded in the opening 12a of the insulating laminate 12 and functions as a connection terminal to an external device. The through wiring 15 is composed of a plurality of wirings 15a to 15c that are stacked together. The wiring 15b includes a wiring formed at the same time as the wiring 13 and a metal film formed at the same time as the barrier metal film 14. FIG.

The surface wiring 16 is wiring for electrically connecting the semiconductor chips mounted on the organic interposer 10 . Therefore, both ends of the surface wiring 16 are exposed from the organic interposer 10, and the surface wiring 16 other than the both ends is embedded in the organic interposer 10 (more specifically, the insulating layer 22). Thus, insulating layer 22 includes at least two insulating layers.

Next, a method for manufacturing the organic interposer 10 will be described with reference to FIGS. 3 to 9. FIG. The organic interposer 10 formed by the manufacturing method described below is particularly suitable for, for example, forms that require miniaturization and an increase in the number of pins. In addition, FIG.4(b) is a one part enlarged view of Fig.4 (a). Similarly, each of FIGS. 5(b), 6(b), 7(b) and 8(b) is an enlarged view of a portion of the corresponding drawing.

First, as a first step, the wiring 15a is formed on the substrate 11 as shown in FIG. 3(a). The wiring 15 a is formed by patterning a metal film formed on the substrate 11 . In the first step, for example, the metal film is formed by a coating method, a vacuum deposition method, a physical vapor deposition method (PVD method) such as sputtering, a printing method or a spray method using a metal paste, or various plating methods. . In this embodiment, a copper foil can be used as the metal film.

When a temporary fixing layer (not shown) is provided between the substrate 11 and the wiring 15a, the temporary fixing layer may be, for example, polyimide, polybenzoxazole, silicon, a resin containing a non-polar component such as fluorine, It contains a resin containing a component that expands or foams by heating or UV (ultraviolet rays), a resin containing a component that undergoes a cross-linking reaction by heating or by UV, or a resin that generates heat when irradiated with light. Methods for forming the temporary fixing layer include, for example, spin coating, spray coating, and lamination. It is preferable that the temporary fixing layer be easily peeled off by an external stimulus such as light or heat, from the viewpoint of achieving a high degree of compatibility between handleability and carrier peelability. From the viewpoint that the temporary fixing layer can be peeled off so that the temporary fixing layer does not remain on the organic interposer 10 to be manufactured later, it is particularly preferable that the temporary fixing layer contains a resin that expands in volume by heat treatment.

When a temporary fixing layer is provided between the substrate 11 and the wiring 15a, the wiring 15a may be made of peelable copper foil. In this case, the substrate 11 corresponds to the support of the peelable copper foil, and the temporary fixing layer corresponds to the release layer of the peelable copper foil.

Next, as a second step, as shown in FIG. 3B, an insulating layer 23 is formed on the substrate 11 so as to cover the wiring 15a. In the second step, a film-like insulating layer 23 containing a negative photosensitive resin is attached to the substrate 11 to cover the wiring 15a. Then, if necessary, the insulating layer 23 is subjected to exposure processing, development processing, hardening processing, and the like.

Next, as a third step, the insulating layer 21 is formed by forming the insulating layer 24 on the insulating layer 23, as shown in FIG. 3(c). In the third step, similarly to the second step, a film-like insulating layer 24 containing a negative photosensitive resin is attached to the insulating layer 23 . Then, if necessary, the insulating layer 24 is subjected to exposure processing, development processing, hardening processing, and the like.

Next, as a fourth step, as shown in FIGS. 4A and 4B, a plurality of grooves 21a and openings 21b are formed in the insulating layer 21 (also referred to as the first step). In the fourth step, for example, a plurality of grooves 21a and openings 21b are formed by laser ablation, photolithography or imprinting. From the viewpoint of miniaturization of the groove 21a and formation cost, it is preferable to apply photolithography. Therefore, the insulating layer 21 is exposed and developed to form a plurality of grooves 21a. Also, the opening 21b is formed to expose the wiring 15a. By using a photosensitive resin for the insulating layer 21, the pattern of the grooves 21a can be formed smoothly in a short period of time. Therefore, the wiring described later can be made excellent in high-frequency characteristics.

As a method for exposing the photosensitive resin in the photolithography, a known projection exposure method, contact exposure method, direct drawing exposure method, or the like can be used. Moreover, in order to develop the photosensitive resin, for example, an alkaline aqueous solution such as sodium carbonate or TMAH may be used.

In the fourth step, after forming the plurality of grooves 21a and the openings 21b, the insulating layer 21 may be further cured by heating. In this case, for example, the heating temperature is set to 100 to 200.degree.

Next, as a fifth step, as shown in FIGS. 5A and 5B, a barrier metal film 14 is formed on the insulating layer 21 so as to cover the inner surface of the trench 21a (also referred to as a second step). ). In the fifth step, the barrier metal film 14 is formed by, for example, a coating method, a PVD method, a printing method or a spray method using a metal paste, or various plating methods. In the coating method, the barrier metal film 14 is formed by coating a palladium or nickel complex on the insulating layer 21 and then heating it. When a metal paste is used, the barrier metal film 14 is formed by applying a paste containing metal particles such as nickel or palladium on the insulating layer 21 and then sintering the paste. In this embodiment, the barrier metal film 14 is formed by sputtering, which is one of the PVD methods. The barrier metal film 14 is formed so as to also cover the inner surface of the opening 21b.

Next, as a sixth step, as shown in FIGS. 6A and 6B, a wiring material layer 13A is formed on the barrier metal film 14 so as to fill the trench 21a (also referred to as a third step). . In the sixth step, the wiring material layer 13A is formed by, for example, a method using a metal paste or a plating method using the barrier metal film 14 as a seed layer. The thickness of the wiring material layer 13A is preferably 0.5 to 3 times the thickness of the insulating layer . When the thickness of the wiring material layer 13A is 0.5 times or more, it tends to be possible to suppress an increase in the surface roughness Ra of the wiring 13 formed in a post-process. Moreover, when the thickness of the wiring material layer 13A is three times or less, the warping of the wiring material layer 13A is suppressed, and the wiring material layer 13A tends to adhere well to the insulating layer 21 . The wiring material layer 13A is formed so as to fill the opening 21b as well.

Next, as a seventh step, as shown in FIGS. 7A and 7B, the wiring material layer 13A is thinned so that the insulating layer 21 is exposed (also referred to as a fourth step). In the seventh step, a portion of the wiring material layer 13A outside the trench 21a and the opening 21b and a portion of the barrier metal film 14 which does not cover the trench 21a or the opening 21b are removed, thereby exposing the insulating layer 21 and removing the wiring material. thin layer 13A; Thereby, the wiring 13 embedded in the groove portion 21a is formed. This thinning treatment may be a flattening treatment for the combined surface of the insulating layer 21 and the wiring 13 . In this case, the target portions of the wiring material layer 13A and the barrier metal film 14 are removed by CMP or fly-cutting, and the surface of the insulating layer 21 is polished or ground to be planarized. Thus, the wiring layer 25 composed of the wiring 13, the barrier metal film 14, and the insulating layer 24 is formed.

When CMP is used in the seventh step, the slurries include, for example, a slurry containing alumina, which is generally used for polishing resin, and a slurry containing hydrogen peroxide and silica, which are used for polishing the barrier metal film 14. and a slurry containing hydrogen peroxide and ammonium persulfate, which is used for polishing the wiring material layer 13A. From the viewpoint of reducing the cost and controlling the surface roughness Ra to 0.01 to 1 μm, the insulating layer 21, the barrier metal film 14 and the wiring material layer 13A (wiring 13) are ground using a slurry containing alumina. is preferred. The use of CMP tends to be costly. Further, when the insulating layer 21, the barrier metal film 14 and the wiring material layer 13A (wiring 13) are planarized at the same time, dishing occurs in the wiring 13 due to the difference in polishing rate, and as a result, the insulating layer 21 and the wiring 13 are combined. The flatness of the surface tends to be greatly impaired. Therefore, from the viewpoint of making the surface roughness Ra of the above surface 0.03 to 0.1 μm, the insulating layer 21, the barrier metal film 14 and the wiring material layer 13A (wiring 13) are formed by a fly-cut method using a surface planer. Grinding is more preferred.

Next, as an eighth step, as shown in FIGS. 8A and 8B, an insulating layer 22 is formed on the insulating layer 21 (also called sixth step). In the eighth step, a film-like insulating layer 22 containing a negative photosensitive resin is attached to the insulating layer 21 . The insulating layer 22 may be the same film as the insulating layer 21, or may be formed using a different photosensitive resin. From the viewpoint of preventing diffusion of the metal forming the wiring 13, it is preferable not to apply a developing treatment to the insulating layer 22. FIG.

Next, as a ninth step, an opening 22a is formed in the insulating layer 22, as shown in FIG. 9(a). In the ninth step, an opening 22a is formed to expose the wiring 15b. The opening 22a is formed by photolithography or the like, for example.

Next, as a tenth step, as shown in FIG. 9B, the through wiring 15 is formed by filling the opening 22a with a metal material to form the wiring 15c. In the tenth step, the wiring 15c is formed by PVD or various plating methods, for example. Metal materials include copper, nickel, tin, and the like. After the tenth step, the organic interposer 10 shown in FIG. 2 is obtained by forming the surface wiring 16 and the like. Note that the organic interposer 10 may be separated from the substrate 11 when a temporary fixing layer is provided.

According to the organic interposer 10 having the configuration described above, the wiring 13 and the insulating layers 21 and 22 are partitioned by the barrier metal film 14 . Therefore, diffusion of the metal material in the wiring 13 into the insulating laminate is suppressed by the barrier metal film 14 . Therefore, short-circuiting between the plurality of wirings 13 via the diffused metal material can be suppressed, so that the insulation reliability of the organic interposer 10 can be improved.

The insulating laminated body 12 includes an insulating layer 21 having a plurality of grooves 21a in which the wirings 13 are arranged, and an insulating layer 22 laminated on the insulating layer 21 so as to embed the wirings 13 therein. Therefore, each of the plurality of wirings 13 has a shape along the groove 21 a of the insulating layer 21 . Therefore, fine wiring 13 can be easily formed by forming a plurality of grooves 21a having fine widths and intervals.

The barrier metal film 14 is provided between the wiring 13 and the inner surface of the trench 21a. Therefore, diffusion of the metal material in the wiring 13 into the insulating layer 21 is well suppressed by the barrier metal film 14 .

The barrier metal film 14 contains at least one of titanium, nickel, palladium, chromium, tantalum, tungsten and gold. Titanium, nickel, palladium, chromium, tantalum, tungsten, and gold do not easily diffuse into the insulating layers 21 and 22, so that the insulation reliability of the organic interposer 10 can be further improved.

The thickness of the insulating layer 21 may be 1-10 μm. In this case, the insulating layer 21 can be used to form a plurality of grooves 21a having widths and intervals of 10 μm or less.

According to the manufacturing method of the organic interposer 10 according to the present embodiment, the barrier metal film 14 can be formed between the inner surface of each groove 21a and the wiring material layer 13A through the fourth to sixth steps. Therefore, diffusion of the metal material in the wiring 13 into the insulating layer 21 is suppressed by the barrier metal film 14 . Therefore, short-circuiting between the plurality of wirings 13 via the diffused metal material can be suppressed, so that the insulation reliability of the organic interposer 10 can be improved.

In the sixth step, the wiring material layer 13A may be formed by plating using the barrier metal film 14 as a seed layer. In this case, the wiring material layer 13A can be formed so that the barrier metal film 14 is sandwiched between the insulating layer 21 and the wiring material layer 13A. As a result, diffusion of the metal material in the wiring material layer 13A into the insulating layer 21 is suppressed satisfactorily.

Note that the wiring 13 in the organic interposer 10 may be formed by, for example, a semi-additive method. In the semi-additive method, a seed layer is formed, a resist having a desired pattern is formed on the seed layer, the exposed portion of the seed layer is thickened by electroplating or the like, and after removing the resist, a thin seed layer is formed. This is a method of etching a layer to obtain desired wiring. However, when the semi-additive method is applied, the wiring is greatly damaged when etching the thin seed layer. In addition, it is difficult to ensure the adhesion strength of the wiring to the insulating layer. Therefore, when fine wiring having a line width and a space width of, for example, 5 μm or less is formed using a semi-additive method, the yield of the organic interposer tends to be greatly reduced. Therefore, in the present embodiment, in order to suppress this decrease in yield, a trench method is adopted in which a groove portion 21a is provided in the insulating layer 21 in the fourth step and the wiring 13 is formed in the groove portion 21a.

Although the organic interposer according to one embodiment of the present disclosure and the method for manufacturing the same have been described above, the present disclosure is not limited to the above-described embodiments, and may be appropriately modified without departing from the scope of the present disclosure. . For example, the cross-sectional shape of the groove portion 21a formed in the insulating layer 21 is not limited to a substantially rectangular shape, and may be a substantially trapezoidal shape, a substantially semicircular shape, or other shape.

In the above embodiment, the wiring 13, the barrier metal film 14, the wirings 15a to 15c, the surface wiring 16, etc. may each have a single-layer structure, or may have a multi-layer structure consisting of a plurality of conductive layers.

Although the insulating layer 21 includes both the insulating layer 23 and the insulating layer 24 in the above embodiment, it is not limited to this. For example, the insulating layer 21 may have a single layer structure. In this case, the second step and the third step in the above manufacturing method can be integrated into one step, and the manufacturing process of the organic interposer 10 can be simplified.

EXAMPLES The present disclosure will be specifically described below with reference to Examples. However, the present disclosure is not limited to the following examples.

<Synthesis of polyimide>
(PI-1)
9.0 g (0.045 mol) of 1,12-dodecamethylenediamine (also known as 1,12-diaminododecane), 1,3-bis( 3-aminopropyl)tetramethyldisiloxane (alias: 1,1,3,3-tetramethyl-1,3-bis(3-aminopropyl)disiloxane) 2.5 g (0.010 mol), 2,2- 16.4 g (0.040 mol) of bis(4-aminophenoxyphenyl)propane and 100 g of N-methyl-2-pyrrolidone were added and then stirred to dissolve each component to obtain a solution. After that, 52.2 g (0.10 mol) of decamethylene bis trimellitate dianhydride (1,10-(decamethylene) bis(trimellitate anhydride)) was added portionwise to this solution. After reacting at room temperature for 1 hour, the solution was heated at 180° C. for 2 hours while blowing nitrogen gas to obtain a solution of polyimide (PI-1). When the weight average molecular weight Mw of the obtained polyimide was measured by GPC, it was 55000 in terms of polystyrene. Moreover, Tg of the obtained polyimide was 120°C.

(PI-2)
15.0 g (0.075 mol) of 1,12-dodecamethylenediamine, 1,3-bis(3-aminopropyl)tetramethyldisiloxane ( Also known as: 1,1,3,3-tetramethyl-1,3-bis(3-aminopropyl)disiloxane) 5.0 g (0.020 mol) and after adding 100 g of N-methyl-2-pyrrolidone Each component was dissolved by stirring to obtain a solution. Then, 41.6 g (0.080 mol) of 4,4′-(4,4′-isopropylidenediphenoxy)bis(phthalic dianhydride) and decamethylene bistrimellitate dianhydride (1, 10.4 g (0.020 mol) of 10-(decamethylene)bis(trimellitate anhydride)) were added in portions. After reacting at room temperature for 1 hour, the solution was heated at 180° C. for 2 hours while blowing nitrogen gas to obtain a solution of polyimide (PI-2). When the weight average molecular weight Mw of the obtained polyimide was measured by GPC, it was 45000 in terms of polystyrene. Moreover, Tg of the obtained polyimide was 80°C.

(PI-3)
15.0 g (0.075 mol) of 1,12-dodecamethylenediamine, 1,3-bis(3-aminopropyl)tetramethyldisiloxane ( Also known as: 1,1,3,3-tetramethyl-1,3-bis(3-aminopropyl)disiloxane) 5.0 g (0.020 mol) and after adding 100 g of N-methyl-2-pyrrolidone Each component was dissolved by stirring to obtain a solution. After that, 52.0 g (0.10 mol) of 4,4'-(4,4'-isopropylidenediphenoxy)bis(phthalic dianhydride) was added little by little to this solution. After reacting at room temperature for 1 hour, the solution was heated at 180° C. for 2 hours while blowing nitrogen gas to obtain a solution of polyimide (PI-3). When the weight average molecular weight Mw of the obtained polyimide was measured by GPC, it was 42000 in terms of polystyrene. Moreover, Tg of the obtained polyimide was 100°C.

(PI-4)
5.22 g (0.045 mol) of 1,6-hexamethylenediamine, 1,3-bis(3-aminopropyl)tetramethyldisiloxane ( Also known as: 1,1,3,3-tetramethyl-1,3-bis(3-aminopropyl)disiloxane) 2.5 g (0.010 mol), 2,2-bis(4-aminophenoxyphenyl)propane 16 After adding .4 g (0.040 mol) and 100 g of N-methyl-2-pyrrolidone, each component was dissolved by stirring to obtain a solution. After that, 52.2 g (0.10 mol) of decamethylene bis trimellitate dianhydride (1,10-(decamethylene) bis(trimellitate anhydride)) was added portionwise to this solution. After reacting at room temperature for 1 hour, the solution was heated at 180° C. for 2 hours while blowing nitrogen gas to obtain a solution of polyimide (PI-4). When the weight average molecular weight Mw of the obtained polyimide was measured by GPC, it was 58000 in terms of polystyrene. Moreover, Tg of the obtained polyimide was 150°C.

(PI-5)
18.0 g (0.045 mol) of polyoxypropylene diamine (manufactured by Mitsui Chemicals Fine Co., Ltd., trade name "D-400") is placed in a 300 mL flask equipped with a thermometer, a stirrer, a condenser, and a nitrogen inlet tube. -bis(3-aminopropyl)tetramethyldisiloxane (also known as 1,1,3,3-tetramethyl-1,3-bis(3-aminopropyl)disiloxane) 2.5 g (0.010 mol), 2 , 2-bis(4-aminophenoxyphenyl)propane 16.4 g (0.040 mol) and N-methyl-2-pyrrolidone 100 g were added and stirred to dissolve each component to obtain a solution. After that, 52.0 g (0.10 mol) of 4,4'-(4,4'-isopropylidenediphenoxy)bis(phthalic dianhydride) was added little by little to this solution. After reacting at room temperature for 1 hour, the solution was heated at 180° C. for 2 hours while blowing nitrogen gas to obtain a solution of polyimide (PI-5). When the weight average molecular weight Mw of the obtained polyimide was measured by GPC, it was 45000 in terms of polystyrene. Moreover, Tg of the obtained polyimide was 80°C.

<Preparation of photosensitive resin composition>
(Example 1)
Polyimide PI-1 (100 parts by mass, solid content), tricyclodecanedimethanol diacrylate (20 parts by mass), ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole- 3-yl]-, 1-(O-acetyloxime) (manufactured by BASF, trade name “I-OXE02”, 5 parts by mass) and cyclopentanone (100 parts by mass) are blended to form a photosensitive resin composition. got stuff

(Example 2)
A photosensitive resin composition was obtained in the same manner as in Example 1, except that PI-2 was used as the polyimide.

(Example 3)
A photosensitive resin composition was obtained in the same manner as in Example 1, except that PI-3 was used as the polyimide.

(Example 4)
A photosensitive resin composition was obtained in the same manner as in Example 1, except that PI-4 was used as the polyimide.

(Comparative example 1)
A photosensitive resin composition was obtained in the same manner as in Example 1, except that PI-5 was used as the polyimide.

<Evaluation>
(Electrical properties (dielectric loss tangent))
After exposing the above-mentioned photosensitive resin composition with a high-precision parallel exposure machine (manufactured by Oak Manufacturing Co., Ltd., trade name “EXM-1172-B-∞”) under the conditions of 200 mJ/cm ² , 100 on a hot plate. C. for 2 minutes, and then heated in an oven for 1 hour at 220.degree. A test piece was prepared by cutting the cured product into a length of 60 mm and a width of 2 mm, followed by vacuum drying at 30° C. for 6 hours. The dielectric loss tangent was calculated from the resonance frequency obtained at 10 GHz and the unloaded Q value. The measurement was performed at a temperature of 25° C. using a vector-type network analyzer E8364B manufactured by Keysight Technologies, CP531 (10 GHz resonator) and CPMA-V2 (program) manufactured by Kanto Denshi Applied Development Co., Ltd.

(Microfabrication (resolution))
After forming a 2 μm-thick layer of the photosensitive resin composition described above on a silicon wafer, a high-precision parallel exposure machine (manufactured by Oak Manufacturing Co., Ltd., trade name “EXM-1172-B-∞”) was used. After exposure treatment under the condition of 200 mJ/cm ² , it was heated under the condition of 100° C. for 2 minutes and further heat cured under the condition of 220° C. for 1 hour to form the first insulating layer. After that, after further forming a 2 μm-thick layer made of the above-mentioned photosensitive resin composition, a projection exposure machine “UX-74101SC” (trade name) manufactured by Ushio Inc. was used to obtain a focus of ±0 μm and an exposure amount. Exposure was performed under the condition of 1000 mJ/cm ² . After that, puddle development was performed using cyclopentanone as a developer at 25° C. for 20 seconds to form a second insulating layer having vias (openings) with diameters of 5 μm and 10 μm on the first insulating layer. formed. The resolution of 5 μm and 10 μm diameter vias was evaluated by microscopy. The minimum diameter at which a via was formed well was evaluated.

(insulation reliability)
For evaluation of insulation reliability, a measurement evaluation sample 50 shown in FIG. 10 was produced as follows. First, 1,3,4,6-tetrakis(methoxymethyl)glycoluril (30 parts by mass), tri An insulating material was obtained by blending methylolpropane triglycidyl ether (40 parts by mass), a triarylsulfonium salt (San-Apro Co., Ltd., trade name "CPI-310B", 8 parts by mass), and methyl ethyl ketone (100 parts by mass). . The resulting insulating material was applied to a polyethylene terephthalate film "A-53" (trade name) manufactured by Teijin DuPont Films Ltd. and dried in an oven at 90°C for 10 minutes to obtain a photosensitive material 52 having a thickness of 3 µm. rice field.

After the above-described photosensitive material 52 having a thickness of 3 μm was attached to a silicon wafer 51 having a thickness of 150 mm, the photosensitive material 52 was subjected to exposure processing and heat curing. Next, a photosensitive material having a thickness of 10 μm containing the above photosensitive resin composition was attached. After exposing the photosensitive material using a photomask, the insulating layer 53 was formed by developing and thermally curing the material. As a result, the insulating layer 53 is patterned to form a groove (first groove) 53a and a groove (second groove) 53b that are comb-shaped so as to mesh with each other, and a connection portion (first groove) connecting the grooves 53a. connection portion) 53c and a connection portion (second connection portion) 53d connecting the groove portions 53b. The width of the groove portion 53a and the width of the groove portion 53b were each set to 2 μm. These widths correspond to the line width L of the wiring. Further, the distance (space width S) between adjacent grooves 53a and 53b was set to 2 μm, and the length of each groove was set to 1 mm.

Next, a barrier metal film 54 containing titanium and having a thickness of 0.05 μm was formed on the surface of the insulating layer 53 and the inner wall of each groove by sputtering. Next, a copper layer was formed by electroplating using the barrier metal film 54 as a seed layer so as to fill the grooves 53a, 53b, connecting portions 53c, and connecting portions 53d. Next, a portion of the copper layer and portions of the barrier metal film 54 that do not cover the inner surfaces of the grooves 53a, 53b, connecting portions 53c and 53d were ground by a fly-cut method using a surface planer. Thus, a wiring (first wiring) 55a buried in the groove 53a, a wiring (second wiring) 55b buried in the groove 53b, and a connection wiring (first connection wiring) 55c buried in the connection portion 53c are formed. , and a connection wiring (second connection wiring) 55d embedded in the connection portion 53d. As the surface planer, an automatic surface planer (manufactured by Disco Co., Ltd., trade name "DAS8930") was used. In the fly-cut grinding, the feed rate was set to 1 mm/s and the spindle rotation speed was set to 2000 min ⁻¹ .

Next, a photosensitive material having a thickness of 5 μm containing the above-described photosensitive resin composition was attached so as to expose part of the connection wiring 55c and part of the connection wiring 55d. Then, after exposing the photosensitive material under conditions of 200 mJ/cm ² using a high-precision parallel exposure machine (manufactured by Oak Manufacturing Co., Ltd., product name “EXM-1172-B-∞”), 100 ° C., 2 The cured product layer 56 was obtained by heating under conditions of 1 minute and further heat curing under conditions of 220° C. and 1 hour. Thus, a measurement evaluation sample 50 shown in FIGS. 10(a) and 10(b) was formed. In this measurement evaluation sample 50 , the wiring 55 a and the connection wiring 55 c are connected to each other and covered with the barrier metal film 54 and the hardened material layer 56 . As a result, a wiring layer 57 composed of the insulating layer 53, the barrier metal film 54, the wiring 55a, and the wiring 55b was obtained.

Next, in order to confirm the insulation reliability of the measurement evaluation sample 50, a highly accelerated stress test (HAST) described below was performed. In this test, a voltage of 3.3 V was applied to the connection wiring 55c and the connection wiring 55d under conditions of humidity of 85% and 130° C., and the devices were allowed to stand still for a predetermined time. In this way, changes in insulation between the wiring 55a and the wiring 55b over time were measured. In this test, if the resistance value between the wiring 55a and the wiring 55b is 1×10 ⁶ Ω or more after 200 hours from the start of the test, it is evaluated as “A”. If it was less than 10 ⁶ Ω, it was evaluated as “B”.

(Evaluation results)
The dielectric loss tangent of Example 1 was 0.005, the resolution was 10 μm, and the insulation reliability was "A". In Example 2, the dielectric loss tangent was 0.008, the resolution was 5 μm, and the insulation reliability was "A". The dielectric loss tangent of Example 3 was 0.008, the resolution was 10 μm, and the insulation reliability was "A". The dielectric loss tangent of Example 4 was 0.01, the resolution was 5 μm, and the insulation reliability was "A". The dielectric loss tangent of Comparative Example 1 was 0.03, the resolution was 5 μm, and the insulation reliability was "B".

10... Organic interposer (semiconductor device), 13, 55a, 55b... Wiring, 24, 53... Insulating layer, 25, 57... Wiring layer.

Claims (8)

A photosensitive resin composition for forming the insulating portion in a wiring layer comprising an insulating portion having an opening and wiring disposed inside the opening,
A polyimide (A) which is a reaction product of a tetracarboxylic dianhydride and a diamine, and two or more carbon-carbon double bonds containing a compound (B),
The diamine is 1,6-hexamethylenediamine, 1,7-heptamethylenediamine, 1,8-octamethylenediamine, 1,9-nonamethylenediamine, 2-methyl-1,8-octamethylenediamine, 1, 10-decamethylenediamine, 1,11-undecamethylenediamine, 1,12-dodecamethylenediamine, 1,13-tridecamethylenediamine, 1,16-hexadecamethylenediamine, 1,18-octadecamethylenediamine, 2,2,4-trimethylhexamethylenediamine and 10 to 80 mol% of at least one selected from the group consisting of 2,4,4-trimethylhexamethylenediamine ,
A photosensitive resin composition in which the content of the component (B) is 5 to 70 parts by mass with respect to 100 parts by mass of the component (A) (provided, however, that (I) an alicyclic tetracarboxylic dianhydride , (II) 20 to 200 parts by mass of a polyfunctional photopolymerizable monomer having a functionality of 3 or more per 100 parts by mass of a polyimide having a structure obtained by condensing a cyclic aliphatic diamine and a chain aliphatic diamine, and (III) photopolymerization initiation. excluding photosensitive resin compositions characterized by containing 0.02 to 40 parts by mass of an agent) . The photosensitive resin composition of claim 1, wherein said diamine comprises 1,12-dodecamethylenediamine. 3. The photosensitive resin composition according to claim 1, wherein the diamine comprises 1,6-hexamethylenediamine. The photosensitive resin composition according to any one of claims 1 to 3, wherein the diamine further comprises 5 to 50 mol% of siloxane diamine. The photosensitive resin composition according to any one of claims 1 to 4, wherein the polyimide has a glass transition temperature of 60 to 220°C. The photosensitive resin composition according to any one of claims 1 to 5, further comprising a photopolymerization initiator . An insulating part having an opening, and wiring arranged inside the opening,
A wiring layer, wherein the insulating part comprises the photosensitive resin composition according to any one of claims 1 to 6 or a cured product thereof. A semiconductor device comprising the wiring layer according to claim 7 .

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