Semiconductor device, manufacturing method thereof, and interlayer insulating film

Abstract

A semiconductor device having excellent adhesion between an interlayer insulating film in a rewiring layer and a sealing material, and a method for manufacturing the same. [Solution] The semiconductor device (1) comprises a semiconductor chip (2), an encapsulant (3) covering the semiconductor chip, and a redistribution layer (4) having an area larger than that of the semiconductor chip in a planar view. The absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film (6) of the redistribution layer at a wavelength of 1310 nm is less than 0.0150. The interlayer insulating film contains at least one material selected from polyimide, polybenzoxazole, and a polymer having a phenolic hydroxyl group.

Description

[Technical field]

[0001] The present invention relates to a semiconductor device and a manufacturing method thereof. [Background technology]

[0002] There are various methods for packaging semiconductor devices. For example, one of the semiconductor packaging methods is to cover a semiconductor chip with a sealing material (mold resin) to form an element sealing material, and then to form a rewiring layer that electrically connects to the semiconductor chip. Among the semiconductor packaging methods, a semiconductor packaging method called Fan-Out has become mainstream in recent years.

[0003] In a fan-out type semiconductor package, a chip sealing body larger than the chip size of the semiconductor chip is formed by covering the semiconductor chip with an encapsulant. Furthermore, a redistribution layer is formed that extends to the area of ​​the semiconductor chip and the encapsulant. The redistribution layer is formed with a thin film thickness. Furthermore, since the redistribution layer can be formed up to the area of ​​the encapsulant, the number of external connection terminals can be increased.

[0004] For example, a fan-out type semiconductor device is known from Patent Document 1 below. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2011-129767 A Summary of the Invention [Problem to be solved by the invention]

[0006] In a fan-out type semiconductor device, high adhesion is required between the interlayer insulating film in the redistribution layer and the sealing material. However, in a conventional fan-out type semiconductor device, the adhesion between the interlayer insulating film in the redistribution layer and the sealing material is insufficient.

[0007] The present invention has been made in view of the above-mentioned problems, and has an object to provide a semiconductor device having excellent adhesion between an interlayer insulating film in a rewiring layer and a sealing material, and a method for manufacturing the same. [Means for solving the problem]

[0008] One aspect of the semiconductor device of the present invention is a semiconductor chip, Contact a sealing material and a rewiring layer having an area larger than that of the semiconductor chip in a plan view; the sealing material has a portion in direct contact with the interlayer insulating film of the redistribution layer; The interlayer insulating film of the redistribution layer is characterized in that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index at a wavelength of 1310 nm is less than 0.0150.

[0009] The present invention One aspect of the interlayer insulating film is an interlayer insulating film for use in forming the redistribution layer in a semiconductor device comprising a semiconductor chip, a sealing material in contact with the semiconductor chip, and a redistribution layer having an area larger than that of the semiconductor chip in a planar view, the interlayer insulating film being in direct contact with the sealing material, and characterized in that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer at a wavelength of 1310 nm is less than 0.0150.

[0010] In one aspect of the semiconductor device of the present invention, the sealing material preferably contains an epoxy resin.

[0011] In one aspect of the semiconductor device of the present invention, the interlayer insulating film preferably contains at least one selected from the group consisting of polyimide, polybenzoxazole, and a polymer having a phenolic hydroxyl group.

[0012] In one aspect of the semiconductor device of the present invention, the interlayer insulating film preferably contains a polyimide having a structure represented by the following general formula (1):

[0013] [ka] (In general formula (1), X 1 is a tetravalent organic group, and Y 1 is a divalent organic group, and m is an integer of 1 or more.

[0014] In one embodiment of the semiconductor device of the present invention, X in the general formula (1) 1 is a tetravalent organic group containing an aromatic ring, and Y in the general formula (1) 1is preferably a divalent organic group containing an aromatic ring.

[0015] In one embodiment of the semiconductor device of the present invention, X in the general formula (1) 1 It is preferable that the compound contains at least one structure represented by the following general formula (2) to general formula (4).

[0016] [ka]

[0017] [ka]

[0018] [ka] (In general formula (4), R9 is an oxygen atom, a sulfur atom, or a divalent organic group.)

[0019] In one embodiment of the semiconductor device of the present invention, X in the general formula (1) 1 It is preferable that the compound contains a structure represented by the following general formula (5).

[0020] [ka]

[0021] In one embodiment of the semiconductor device of the present invention, Y in the general formula (1) 1 It is preferable that the compound contains at least one structure represented by the following general formula (6) to general formula (8).

[0022] [ka] (R 10 , R 11 , R 12 and R 13 are hydrogen atoms, monovalent aliphatic groups having 1 to 5 carbon atoms, or hydroxyl groups, and may be the same or different.

[0023] [ka] (R 14 ~R 21 are hydrogen atoms, halogen atoms, monovalent organic groups having 1 to 5 carbon atoms, or hydroxyl groups, and may be different from each other or the same.)

[0024] [ka] (R 22 is a divalent group, R 23 ~R 30 are hydrogen atoms, halogen atoms, monovalent aliphatic groups having 1 to 5 carbon atoms, or hydroxyl groups, and may be the same or different.

[0025] In one embodiment of the semiconductor device of the present invention, Y in the general formula (1) 1 It is preferable that the compound contains a structure represented by the following general formula (9).

[0026] [ka]

[0027] In one embodiment of the semiconductor device of the present invention, the polybenzoxazole preferably includes a polybenzoxazole having a structure represented by the following general formula (10).

[0028] [ka] (In general formula (10), U and V are divalent organic groups.)

[0029] In one embodiment of the semiconductor device of the present invention, U in the general formula (10) is preferably a divalent organic group having 1 to 30 carbon atoms.

[0030] In one embodiment of the semiconductor device of the present invention, U in the general formula (10) is preferably a chain alkylene group having 1 to 8 carbon atoms in which some or all of the hydrogen atoms have been substituted with fluorine atoms.

[0031] In one embodiment of the semiconductor device of the present invention, V in the general formula (10) is preferably a divalent organic group containing an aromatic group.

[0032] In one embodiment of the semiconductor device of the present invention, V in the general formula (10) preferably includes at least one structure represented by the following general formulas (6) to (8).

[0033] [ka] (R 10 , R 11 , R 12 and R 13 are hydrogen atoms or monovalent aliphatic groups having 1 to 5 carbon atoms, and may be the same or different.

[0034] [ka] (R 14 ~R 21 are hydrogen atoms, halogen atoms, or monovalent organic groups having 1 to 5 carbon atoms, and may be different or the same.)

[0035] [ka] (R 22 is a divalent group, R 23 ~R 30 are hydrogen atoms, halogen atoms, or monovalent aliphatic groups having 1 to 5 carbon atoms, and may be the same or different.

[0036] In one embodiment of the semiconductor device of the present invention, V in the general formula (10) preferably includes a structure represented by the following general formula (9).

[0037] [ka]

[0038] In one embodiment of the semiconductor device of the present invention, V in the general formula (10) is preferably a divalent organic group having 1 to 40 carbon atoms.

[0039] In one embodiment of the semiconductor device of the present invention, V in the general formula (10) is preferably a divalent chain aliphatic group having 1 to 20 carbon atoms.

[0040] In one aspect of the semiconductor device of the present invention, the polymer having a phenolic hydroxyl group preferably includes a novolac phenol resin.

[0041] In one aspect of the semiconductor device of the present invention, the polymer having a phenolic hydroxyl group preferably contains a phenol resin having no unsaturated hydrocarbon group and a modified phenol resin having an unsaturated hydrocarbon group.

[0042] In one embodiment of the semiconductor device of the present invention, when the redistribution layer is viewed in cross section, it is preferable that the redistribution layer includes a first interlayer insulating film layer, a second interlayer insulating film layer, and an intermediate layer that is a layer different from the first interlayer insulating film layer and the second interlayer insulating film layer and is provided between the first interlayer insulating film layer and the second interlayer insulating film layer.

[0043] In one embodiment of the semiconductor device of the present invention, it is preferable that the first interlayer insulating film layer is in contact with the sealing material, and the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the first interlayer insulating film layer is less than 0.0150.

[0044] In one embodiment of the semiconductor device of the present invention, the second interlayer insulating film layer preferably has a different composition from the first interlayer insulating film layer.

[0045] In one embodiment of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the second interlayer insulating film layer is different from the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the first interlayer insulating film layer.

[0046] In one aspect of the semiconductor device of the present invention, the semiconductor device is preferably a fan-out type wafer level chip size package type semiconductor device.

[0047] In one aspect of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0145 or less.

[0048] In one aspect of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0140 or less.

[0049] In one aspect of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0135 or less.

[0050] In one aspect of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0130 or less.

[0051] In one aspect of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0120 or less.

[0052] In one aspect of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0005 or more.

[0053] In one aspect of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0010 or more.

[0054] In one aspect of the semiconductor device of the present invention, it is preferable that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0015 or more.

[0055] One aspect of the method for manufacturing a semiconductor device of the present invention includes the steps of covering a semiconductor chip with an encapsulant and forming a redistribution layer having an area larger than that of the semiconductor chip in a planar view and including an interlayer insulating film, and is characterized in that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film is less than 0.0150.

[0056] In one embodiment of the method for producing a semiconductor device of the present invention, it is preferable to include an interlayer insulating film formation step of forming the interlayer insulating film from a photosensitive resin composition capable of forming at least one compound selected from the group consisting of polyimide, polybenzoxazole, and a polymer having a phenolic hydroxyl group.

[0057] In one aspect of the method for manufacturing a semiconductor device of the present invention, the interlayer insulating film forming step preferably includes a step of forming the interlayer insulating film from the photosensitive resin composition adjusted with an additive such that the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film is less than 0.0150. Effect of the Invention

[0058] According to the present invention, it is possible to provide a semiconductor device having excellent adhesion between an interlayer insulating film in a rewiring layer and a sealing material, and a method for manufacturing the same. [Brief description of the drawings]

[0059] [Figure 1] 1 is a schematic cross-sectional view of a semiconductor device according to an embodiment of the present invention; [Diagram 2] 1 is a schematic plan view of a semiconductor device according to an embodiment of the present invention; [Diagram 3] 1 is a diagram showing an example of a manufacturing process of the semiconductor device according to the present embodiment. [Figure 4] This is a comparison diagram between flip-chip BGA and fan-out type WLCSP. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0060] Hereinafter, an embodiment of the semiconductor device of the present invention (hereinafter, abbreviated as "embodiment") will be described in detail with reference to the drawings. Note that the present invention is not limited to the following embodiment, and various modifications can be made within the scope of the gist of the present invention.

[0061] (Semiconductor Device) Fig. 1 is a schematic cross-sectional view of the semiconductor device of the present embodiment. As shown in Fig. 1, the semiconductor device (semiconductor IC) 1 includes a semiconductor chip 2, a sealing material (mold resin) 3 that covers the semiconductor chip 2, and a rewiring layer 4 that is in close contact with the semiconductor chip 2 and the sealing material 3.

[0062] As shown in FIG. 1, the sealing material 3 covers the surface of the semiconductor chip 2 and is formed to have an area larger than the region of the semiconductor chip 2 in a plan view (as viewed from the direction of arrow A).

[0063] The redistribution layer 4 is composed of a plurality of wires 5 electrically connected to a plurality of terminals 2a provided on the semiconductor chip 2, and an interlayer insulating film 6 filling the spaces between the wires 5. The plurality of terminals 2a provided on the semiconductor chip 2 and the wires 5 in the redistribution layer 4 are electrically connected. One end of the wires 5 is connected to the terminals 2a, and the other end is connected to an external connection terminal 7. The wires 5 between the terminals 2a and the external connection terminal 7 are covered entirely with the interlayer insulating film 6.

[0064] As shown in Fig. 1, in plan view (as viewed by arrow A), the redistribution layer 4 is formed to be larger than the semiconductor chip 2. The semiconductor device 1 shown in Fig. 1 is a fan-out type wafer-level chip size package (WLCSP) type semiconductor device. In a fan-out type semiconductor device, the interlayer insulating film 6 in the redistribution layer 4 is in close contact with not only the semiconductor chip 2 but also the encapsulant 3. The semiconductor chip 2 is made of a semiconductor such as silicon, and has a circuit formed therein.

[0065] (Rewiring layer) The redistribution layer 4 is mainly composed of the wiring 5 and an interlayer insulating film 6 that covers the periphery of the wiring 5. From the viewpoint of preventing unintended electrical connection with the wiring 5, the interlayer insulating film 6 is preferably made of a material with high insulating properties.

[0066] Here, the "rewiring layer 4" in this embodiment is a thin film layer having wiring 5 and interlayer insulating film 6 as described above, and does not include an interposer or a printed wiring board. Fig. 4 is a comparison diagram between a flip-chip BGA and a fan-out type WLCSP. Since the semiconductor device (semiconductor IC) 1 (see Fig. 1) uses the rewiring layer 4, as shown in Fig. 4, it is thinner than a semiconductor device using an interposer such as a flip-chip BGA.

[0067] In this embodiment, the thickness of the redistribution layer 4 can be about 3 to 30 μm. The thickness of the redistribution layer 4 may be 1 μm or more, 5 μm or more, or 10 μm or more. The thickness of the redistribution layer 4 may be 40 μm or less, 30 μm or less, or 20 μm or less.

[0068] When the semiconductor device 1 is viewed from above (as viewed from the direction of arrow A), it appears as shown in the following Fig. 2. Fig. 2 is a schematic plan view of the semiconductor device of this embodiment. Note that the sealing material 3 is omitted.

[0069] The semiconductor device 1 shown in FIG. 2 (see FIG. 1) is configured so that the area S1 of the redistribution layer 4 is larger than the area S2 of the semiconductor chip 2. There is no particular limitation on the area S1 of the redistribution layer 4, but from the viewpoint of increasing the number of external connection terminals, the area S1 of the redistribution layer 4 is preferably 1.05 times or more, more preferably 1.1 times or more, more preferably 1.2 times or more, and particularly preferably 1.3 times or more, of the area S2 of the semiconductor chip 2. There is no particular limitation on the upper limit, but the area S1 of the redistribution layer 4 may be 50 times or less, 25 times or less, 10 times or less, or 5 times or less of the area S2 of the semiconductor chip 2. In FIG. 2, the area S1 of the redistribution layer 4 includes the area of ​​the part of the redistribution layer 4 covered by the semiconductor chip 2.

[0070] In addition, the external shapes of the semiconductor chip 2 and the redistribution layer 4 may be the same or different. In Fig. 2, the external shapes of the semiconductor chip 2 and the redistribution layer 4 are both similar rectangular shapes, but the shape may be other than rectangular.

[0071] The redistribution layer 4 may be a single layer or a multi-layer structure of two or more layers. The redistribution layer 4 includes the wiring 5 and the interlayer insulating film 6 filling the spaces between the wiring 5, but the redistribution layer 4 may include a layer composed only of the interlayer insulating film 6 or a layer composed only of the wiring 5.

[0072] The wiring 5 is not particularly limited as long as it is made of a highly conductive material, but copper is generally used.

[0073] (Sealing material) The material of the sealing material 3 is not particularly limited, but epoxy resin is preferable from the viewpoints of heat resistance and adhesion to the interlayer insulating film.

[0074] 1, it is preferable that the encapsulant 3 be in direct contact with the semiconductor chip 2 and the rewiring layer 4. This makes it possible to effectively improve the encapsulation performance from the surface of the semiconductor chip 2 to the surface of the rewiring layer 4.

[0075] The sealing material 3 may be a single layer or may have a structure in which multiple layers are laminated. When the sealing material 3 has a laminated structure, it may be a laminated structure of the same type of material or a laminated structure of different materials.

[0076] (Interlayer insulating film) This embodiment is characterized in that the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film 6 is less than 0.0150. Here, the in-plane refractive index is the average value of the refractive indexes at a wavelength of 1310 nm in the x and y directions of the interlayer insulating film 6 having a thickness z, width x, and length y. The out-of-plane refractive index is the refractive index at a wavelength of 1310 nm in the z direction. Hereinafter, the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index at a wavelength of 1310 nm is referred to as the refractive index difference.

[0077] The width x direction of the interlayer insulating film 6 is the planar direction of the interlayer insulating film 6 in FIG. 2, the length y direction is the planar direction of the interlayer insulating film 6 in FIG. 2 and a direction perpendicular to the width x direction, and the thickness z direction is the direction perpendicular to the width x direction and the length y direction.

[0078] If the refractive index difference is less than 0.0150, the adhesion during high-temperature treatment is excellent between the interlayer insulating film 6 and the sealing material 3. Although the reason for this is not clear, the present inventors speculate as follows.

[0079] In the manufacturing process of a fan-out type semiconductor device 1 (see FIG. 1), a photosensitive resin composition is applied onto a chip sealing body composed of a semiconductor chip 2 and an encapsulant 3 in order to form a rewiring layer 4. The photosensitive resin composition is then exposed to light including i-rays. The photosensitive resin composition is then developed and cured to selectively form a portion with and without the cured product of the photosensitive resin composition. The cured product of the photosensitive resin composition becomes an interlayer insulating film 6. Furthermore, wiring 5 is formed in the portion without the cured product of the photosensitive resin composition. Usually, the rewiring layer 4 is often multi-layered. That is, a photosensitive resin composition is further applied onto the interlayer insulating film 6 and the wiring 5, exposed to light, developed, and cured.

[0080] Incidentally, the process of forming the interlayer insulating film 6 and the wiring 5 may include a reflow process depending on the manufacturing method. In the reflow process, if the sealing material is heated for a long time, gas may be generated from the sealing material. If the molecular chains of the interlayer insulating film 6 are properly arranged in the in-plane direction and packed, that is, if the refractive index difference is large, the gas generated from the sealing material cannot pass through the interlayer insulating film 6 and is difficult to escape to the outside. Therefore, gas accumulates at the interface between the sealing material 3 and the interlayer insulating film 6, and the sealing material 3 and the interlayer insulating film 6 are easily peeled off. In particular, epoxy resin is prone to generating gas due to high-temperature thermal history. Therefore, it is considered that when epoxy resin is used for the sealing material 3, the adhesion between the interlayer insulating film 6 and the sealing material 3 is reduced.

[0081] The interlayer insulating film 6 of this embodiment has a small refractive index difference of less than 0.0150, and has high randomness of molecular chains in the interlayer insulating film 6. Therefore, in this embodiment, it is presumed that even under conditions in which gas is easily released from the interlayer insulating film 6 and gas is easily generated from the sealing material 3, there is little peeling between the interlayer insulating film 6 and the sealing material 3, and the adhesion is high.

[0082] From the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3 after high-temperature treatment, the refractive index difference of the interlayer insulating film 6 is preferably less than 0.0150, preferably 0.0145 or less, preferably 0.0140 or less, preferably 0.0135 or less, preferably 0.0130 or less, preferably 0.0125 or less, preferably 0.0120 or less, preferably 0.0115 or less, preferably 0.0110 or less, preferably 0.0095 or less, preferably 0.0090 or less, and preferably 0.0085 or less. , preferably 0.0080 or less, preferably 0.0075 or less, preferably 0.0070 or less, preferably 0.0065 or less, preferably 0.0060 or less, preferably 0.0055 or less, preferably 0.0050 or less, preferably 0.0045 or less, preferably 0.0040 or less, preferably 0.0035 or less, preferably 0.0030 or less, preferably 0.0025 or less, preferably 0.0020 or less, and preferably 0.0010 or less.

[0083] Furthermore, the lower limit of the refractive index difference of the interlayer insulating film 6 is not particularly limited, but may be 0.0000 or more, 0.0005 or more, 0.0010 or more, or 0.0015 or more.

[0084] The interlayer insulating film 6 in the redistribution layer 4 may be multi-layered. That is, the redistribution layer 4 may include a first interlayer insulating film layer, a second interlayer insulating film layer, and an intermediate layer that is a layer different from the first interlayer insulating film layer and the second interlayer insulating film layer and is provided between the first interlayer insulating film layer and the second interlayer insulating film layer when the redistribution layer 4 is viewed in cross section. The intermediate layer is, for example, a wiring 5.

[0085] The first interlayer insulating film layer and the second interlayer insulating film layer may have the same composition or different compositions. The first interlayer insulating film layer and the second interlayer insulating film layer may have the same refractive index difference or different refractive index differences. The first interlayer insulating film layer and the second interlayer insulating film layer may have the same film thickness or different film thicknesses. If the first interlayer insulating film layer and the second interlayer insulating film layer have different compositions, different refractive index differences, or different film thicknesses, it is possible to impart different properties to each interlayer insulating film layer, which is preferable.

[0086] When the interlayer insulating film 6 is a multi-layer film, it is sufficient that the refractive index difference of at least one of the multiple layers of the interlayer insulating film 6 is less than 0.0150, but because the sealing material 3 and the interlayer insulating film layer are easily peeled off by gas, it is preferable that the refractive index difference of the interlayer insulating film 6 of the interlayer insulating film layer in contact with the sealing material 3 is less than 0.0150. If the refractive index difference of the interlayer insulating film 6 of the interlayer insulating film layer in contact with the sealing material 3 is less than 0.0150, gas generated in the sealing material 3 can be efficiently removed.

[0087] The preferable refractive index difference between the interlayer insulating film layers is the same as the preferable refractive index difference of the interlayer insulating film 6 .

[0088] (Composition of Interlayer Insulating Film) The composition of the interlayer insulating film 6 is not particularly limited, but it is preferable that the film contains at least one compound selected from, for example, polyimide, polybenzoxazole, or a polymer having a phenolic hydroxyl group.

[0089] (Resin composition for forming interlayer insulating film) The resin composition used to form the interlayer insulating film 6 is not particularly limited as long as it is a photosensitive resin composition, but is preferably a photosensitive resin composition containing at least one compound selected from a polyimide precursor, a polybenzoxazole precursor, or a polymer having a phenolic hydroxyl group. The resin composition used to form the interlayer insulating film 6 may be in the form of a liquid or a film. In addition, the resin composition used to form the interlayer insulating film 6 may be a negative photosensitive resin composition or a positive photosensitive resin composition.

[0090] In this embodiment, the pattern obtained after exposing and developing the photosensitive resin composition is referred to as a relief pattern, and the relief pattern cured by heating is referred to as a cured relief pattern. This cured relief pattern becomes the interlayer insulating film 6.

[0091] <Polyimide precursor composition> (A) Photosensitive resin Examples of the photosensitive resin used in the polyimide precursor composition include polyamide, polyamic acid ester, etc. For example, the polyamic acid ester may be a polyamic acid ester containing a repeating unit represented by the following general formula (11).

[0092] [ka] R 1 and R 2 are each independently a hydrogen atom, a saturated aliphatic group having 1 to 30 carbon atoms, an aromatic group, a monovalent organic group having a carbon-carbon unsaturated double bond, or a monovalent ion having a carbon-carbon unsaturated double bond. 1 is a tetravalent organic group, and Y 1 is a divalent organic group, and m is an integer of 1 or greater. m is preferably 2 or greater, and more preferably 5 or greater.

[0093] In the above general formula (11), R 1 and R 2 When exists as a monovalent cation, O carries a negative charge (-O - (It exists as X. 1and Y 1 may contain a hydroxyl group.

[0094] R in general formula (11) 1 and R 2 is more preferably a structure having an ammonium ion at the terminal of a monovalent organic group represented by the following general formula (12) or a monovalent organic group represented by the following general formula (13).

[0095] [ka] (In general formula (12), R3, R4, and R5 each independently represent a hydrogen atom or an organic group having 1 to 5 carbon atoms, and m1 represents an integer of 1 to 20.)

[0096] [ka] (In general formula (13), R6, R7, and R8 each independently represent a hydrogen atom or an organic group having 1 to 5 carbon atoms, and m2 represents an integer of 1 to 20.)

[0097] A plurality of polyamic acid esters represented by the general formula (11) may be mixed, or a polyamic acid ester obtained by copolymerizing two or more polyamic acid esters represented by the general formula (11) may be used.

[0098] X 1 However, from the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3, X 1 is preferably a tetravalent organic group containing an aromatic group. 1 is preferably a tetravalent organic group containing at least one structure represented by the following general formulae (2) to (4).

[0099] [ka]

[0100] [ka]

[0101] [ka] (In general formula (4), R9 is an oxygen atom, a sulfur atom, or a divalent organic group.)

[0102] In the general formula (4), R9 is, for example, a divalent organic group having 1 to 40 carbon atoms or a halogen atom. R9 may contain a hydroxyl group.

[0103] From the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3, X 1 is particularly preferably a tetravalent organic group containing a structure represented by the following general formula (5).

[0104] [ka]

[0105] Y 1 However, from the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3, Y 1 is preferably a divalent organic group containing an aromatic group. 1 is preferably a divalent organic group containing at least one structure represented by the following general formula (6) to general formula (8).

[0106] [ka] (R 10 , R 11 , R 12 and R 13 are hydrogen atoms or monovalent aliphatic groups having 1 to 5 carbon atoms, and may be the same or different.

[0107] [ka] (R 14 ~R 21are hydrogen atoms, halogen atoms, or monovalent organic groups having 1 to 5 carbon atoms, and may be different or the same.)

[0108] [ka] (R 22 is a divalent group, R 23 ~R 30 are hydrogen atoms, halogen atoms, or monovalent aliphatic groups having 1 to 5 carbon atoms, and may be the same or different.

[0109] R in general formula (8) 22 is, for example, a divalent organic group having 1 to 40 carbon atoms or a halogen atom.

[0110] From the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3, Y 1 is particularly preferably a divalent organic group containing a structure represented by the following general formula (9).

[0111] [ka]

[0112] In the polyamic acid ester, X in the repeating unit 1 is derived from the tetracarboxylic dianhydride used as the raw material, and Y 1 is derived from the diamine used as a raw material.

[0113] Examples of tetracarboxylic dianhydrides used as raw materials include, but are not limited to, pyromellitic anhydride, diphenylether-3,3',4,4'-tetracarboxylic dianhydride, benzophenone-3,3',4,4'-tetracarboxylic dianhydride, biphenyl-3,3',4,4'-tetracarboxylic dianhydride, diphenylsulfone-3,3',4,4'-tetracarboxylic dianhydride, diphenylmethane-3,3',4,4'-tetracarboxylic dianhydride, 2,2-bis(3,4-phthalic anhydride)propane, 2,2-bis(3,4-phthalic anhydride)-1,1,1,3,3,3-hexafluoropropane, etc. These may be used alone or in combination of two or more.

[0114] Examples of diamines used as raw materials include p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 3,3'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, and 3,3'-diaminodiphenyl. sulfone, 4,4'-diaminobiphenyl, 3,4'-diaminobiphenyl, 3,3'-diaminobiphenyl, 4,4'-diaminobenzophenone, 3,4'-diaminobenzophenone, 3,3'-diaminobenzophenone, 4,4'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,3-bis(3-amino phenoxy)benzene, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]sulfone, 4,4-bis(4-aminophenoxy)biphenyl, 4,4-bis(3-aminophenoxy)biphenyl, bis[4-(4-aminophenoxy)phenyl]ether, bis[4-(3-aminophenoxy)phenyl]ether, 1,4-bis(4-aminophenyl)benzene, 1,3-bis(4-aminophenyl)benzene, 9,1 Examples of the aryl group include 0-bis(4-aminophenyl)anthracene, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-aminophenyl)hexafluoropropane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 1,4-bis(3-aminopropyldimethylsilyl)benzene, ortho-tolidine sulfone, and 9,9-bis(4-aminophenyl)fluorene. In addition, some of the hydrogen atoms on the benzene ring may be substituted. In addition, these may be used alone or in combination of two or more.

[0115] In the synthesis of the polyamic acid ester (A), a method can be preferably used in which a tetracarboxylic acid diester obtained by an esterification reaction of a tetracarboxylic acid dianhydride, which will be described later, is directly subjected to a condensation reaction with a diamine.

[0116] The alcohols used in the esterification reaction of the tetracarboxylic dianhydride are alcohols having an olefinic double bond. Specific examples include, but are not limited to, 2-hydroxyethyl methacrylate, 2-methacryloyloxyethyl alcohol, glycerin diacrylate, and glycerin dimethacrylate. These alcohols can be used alone or in combination of two or more.

[0117] A specific synthesis method for the polyamic acid ester (A) used in this embodiment can employ a conventionally known method. For example, the synthesis method can be the method shown in International Publication No. 00 / 43439. That is, a method can be mentioned in which a tetracarboxylic acid diester is first converted into a tetracarboxylic acid diester diacid chloride, and the tetracarboxylic acid diester diacid chloride and a diamine are subjected to a condensation reaction in the presence of a basic compound to produce the polyamic acid ester (A). Another example can be a method in which a tetracarboxylic acid diester and a diamine are subjected to a condensation reaction in the presence of an organic dehydrating agent to produce the polyamic acid ester (A).

[0118] Examples of organic dehydrating agents include dicyclohexylcarbodiimide (DCC), diethylcarbodiimide, diisopropylcarbodiimide, ethylcyclohexylcarbodiimide, diphenylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-cyclohexyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and the like.

[0119] The weight average molecular weight of the polyamic acid ester (A) used in the present embodiment is preferably 6,000 to 150,000, more preferably 7,000 to 50,000, and even more preferably 7,000 to 20,000.

[0120] (B1) Photoinitiator When the resin composition used to form the interlayer insulating film 6 is a negative photosensitive resin, a photoinitiator is added. Examples of photoinitiators include benzophenone, o-benzoylbenzoic acid methyl, 4-benzoyl-4'-methyldiphenyl ketone, dibenzyl ketone, fluorenone and other benzophenone derivatives, 2,2'-diethoxyacetophenone, 2-hydroxy-2-methylpropiophenone and other acetophenone derivatives, 1-hydroxycyclohexylphenyl ketone, thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, diethylthioxanthone and other thioxanthone derivatives, benzil, benzil dimethyl ketal, and benzyl-β-methoximethane. benzyl derivatives such as diethyl acetal, benzoin derivatives such as benzoin methyl ether, azides such as 2,6-di(4'-diazidobenzal)-4-methylcyclohexanone and 2,6'-di(4'-diazidobenzal)cyclohexanone, 1-phenyl-1,2-butanedione-2-(O-methoxycarbonyl)oxime, 1-phenylpropanedione-2-(O-methoxycarbonyl)oxime, 1-phenylpropanedione-2-(O-ethoxycarbonyl)oxime, 1-phenylpropanedione-2-(O-benzoyl)oxime, 1,3-diphenylpropanedione-2-(O-benzoyl)oxime, Oximes such as 1-phenyl-3-ethoxypropanetrione-2-(O-ethoxycarbonyl)oxime, 1-phenyl-3-ethoxypropanetrione-2-(O-benzoyl)oxime, N-arylglycines such as N-phenylglycine, peroxides such as benzoyl peroxide, aromatic biimidazoles, titanocenes, etc. are used. Among these, the above-mentioned oximes are preferred in terms of photosensitivity.

[0121] The amount of the photoinitiator added is preferably 1 to 40 parts by mass, more preferably 2 to 20 parts by mass, based on 100 parts by mass of the polyamic acid ester (A). By adding 1 part by mass or more of the photoinitiator based on 100 parts by mass of the polyamic acid ester (A), excellent photosensitivity is achieved. Furthermore, by adding 40 parts by mass or less, excellent thick-film curing properties are achieved.

[0122] (B2) Photoacid generator When the resin composition used to form the interlayer insulating film 6 is a positive-type photosensitive resin, a photoacid generator is added. By including a photoacid generator, acid is generated in the ultraviolet-exposed area, and the solubility of the exposed area in an alkaline aqueous solution increases. This allows the composition to be used as a positive-type photosensitive resin composition.

[0123] Examples of photoacid generators include quinone diazide compounds, sulfonium salts, phosphonium salts, diazonium salts, and iodonium salts. Among these, quinone diazide compounds are preferably used because they exhibit excellent dissolution suppression effects and can provide a highly sensitive positive-type photosensitive resin composition. In addition, two or more types of photoacid generators may be contained.

[0124] (C) Additives The difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film 6 can be adjusted by the type and amount of additive. When an additive having a bulky structure is used, the additive enters between the polymer molecular chains, and the arrangement of the polymer molecular chains is disturbed. By disturbing the arrangement of the polymer molecular chains, the intermolecular force between the polymer molecular chains is reduced, and the molecular chains tend to be arranged randomly in the in-plane direction and the out-of-plane direction, and the difference between the in-plane refractive index and the out-of-plane refractive index can be reduced. As an additive having a bulky structure, for example, an additive having a bicyclo structure can be mentioned. As an additive for reducing the refractive index difference, for example, bicyclooctane, adamantane, etc. can be used. In addition, the amount of additive may be appropriately adjusted according to the target difference between the in-plane refractive index and the out-of-plane refractive index. In addition, the difference between the in-plane refractive index and the out-of-plane refractive index can also be reduced by lowering the temperature during thermal curing of the relief pattern.

[0125] (D) Solvent There is no particular limitation as long as the solvent can dissolve or disperse each component. Examples include N-methyl-2-pyrrolidone, γ-butyrolactone, acetone, methyl ethyl ketone, dimethyl sulfoxide, etc. These solvents can be used in the range of 30 to 1500 parts by mass per 100 parts by mass of the photosensitive resin (A) depending on the coating film thickness and viscosity.

[0126] (E) Other The polyimide precursor composition may contain a crosslinking agent. As the crosslinking agent, a crosslinking agent capable of crosslinking the (A) photosensitive resin or capable of forming a crosslinked network by itself can be used when the polyimide precursor composition is exposed to light, developed, and then heat-cured. By using the crosslinking agent, the heat resistance and chemical resistance of the cured film (interlayer insulating film) can be further enhanced.

[0127] In addition, the coating layer may contain a sensitizer for improving photosensitivity, an adhesion aid for improving adhesion to a substrate, and the like.

[0128] (developing) After the polyimide precursor composition is exposed to light, unnecessary parts are washed away with a developer. There are no particular limitations on the developer used, but in the case of a polyimide precursor composition that is developed with a solvent, good solvents such as N,N-dimethylformamide, dimethylsulfoxide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, cyclopentanone, γ-butyrolactone, and acetate esters, and mixed solvents of these good solvents with poor solvents such as lower alcohols, water, and aromatic hydrocarbons are used. After development, rinse washing is performed with a poor solvent, etc., as necessary.

[0129] In the case of a polyimide precursor composition that is developed with an alkaline aqueous solution, preferred are aqueous solutions of compounds that exhibit alkalinity, such as an aqueous solution of tetramethylammonium hydroxide, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, and hexamethylenediamine.

[0130] (thermal curing) After development, the exposed polyimide precursor composition is heated to close the ring of the polyimide precursor and form a polyimide. This polyimide becomes the cured relief pattern, that is, the interlayer insulating film 6.

[0131] The heating temperature for thermal curing of the polyimide precursor composition is not particularly limited, but generally, the lower the heat curing temperature, the smaller the refractive index difference tends to be. From the viewpoint of realizing the refractive index difference of less than 0.0150 in this embodiment, the heating temperature is preferably 200°C or less, more preferably 180°C or less, and even more preferably 160°C or less.

[0132] <Polyimide> The structure of the cured relief pattern formed from the polyimide precursor composition is represented by the following general formula (1).

[0133] [ka]

[0134] X in general formula (1) 1 , Y 1 , m is X in general formula (11) 1 , Y 1 , m, and X 1 is a tetravalent organic group, and Y 1 is a divalent organic group, and m is an integer of 1 or more. 1 , Y 1For the same reason, m is also preferred in the polyimide of general formula (1).

[0135] In the case of an alkali-soluble polyimide, the polyimide may be terminated with a hydroxyl group.

[0136] <Polybenzoxazole Precursor Composition> (A) Photosensitive resin As the photosensitive resin used in the polybenzoxazole precursor composition, a poly(o-hydroxyamide) containing a repeating unit represented by the following general formula (14) can be used.

[0137] [ka] (In general formula (14), U and V are divalent organic groups.)

[0138] From the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3, U is preferably a divalent organic group having 1 to 30 carbon atoms, more preferably a chain alkylene group having 1 to 15 carbon atoms (however, the hydrogen atoms of the chain alkylene may be substituted with halogen atoms), and particularly preferably a chain alkylene group having 1 to 8 carbon atoms and some or all of the hydrogen atoms being substituted with fluorine atoms.

[0139] In addition, from the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3, V is preferably a divalent organic group containing an aromatic group, and more preferably a divalent organic group containing at least one structure represented by the following general formulas (6) to (8).

[0140] [ka] (R 10 , R 11 , R 12 and R 13 are hydrogen atoms or monovalent aliphatic groups having 1 to 5 carbon atoms, and may be the same or different.

[0141] [ka] (R 14 ~R 21 are hydrogen atoms, halogen atoms, or monovalent organic groups having 1 to 5 carbon atoms, and may be different or the same.)

[0142] [ka] (R 22 is a divalent group, R 23 ~R 30 are hydrogen atoms, halogen atoms, or monovalent aliphatic groups having 1 to 5 carbon atoms, and may be the same or different.

[0143] R in general formula (8) 22 is, for example, a divalent organic group having 1 to 40 carbon atoms or a halogen atom.

[0144] From the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3, V is particularly preferably a divalent organic group containing a structure represented by the following general formula (9).

[0145] [ka]

[0146] From the viewpoint of adhesion between the interlayer insulating film 6 and the sealing material 3, V is preferably a divalent organic group having 1 to 40 carbon atoms, more preferably a divalent chain aliphatic group having 1 to 40 carbon atoms, and particularly preferably a divalent chain aliphatic group having 1 to 20 carbon atoms.

[0147] The polybenzoxazole precursor can generally be synthesized from a dicarboxylic acid derivative and a hydroxyl group-containing diamine. Specifically, the polybenzoxazole precursor can be synthesized by converting the dicarboxylic acid derivative into a dihalide derivative and then reacting it with a diamine. As the dihalide derivative, a dichloride derivative is preferable.

[0148] The dichloride derivative can be synthesized by reacting a dicarboxylic acid derivative with a halogenating agent, such as thionyl chloride, phosphoryl chloride, phosphorus oxychloride, or phosphorus pentachloride, which are commonly used in acid chloride reactions of carboxylic acids.

[0149] The dichloride derivative can be synthesized by reacting a dicarboxylic acid derivative with the above-mentioned halogenating agent in a solvent, or by carrying out the reaction in an excess of the halogenating agent and then distilling off the excess.

[0150] Examples of dicarboxylic acids used in the dicarboxylic acid derivative include isophthalic acid, terephthalic acid, 2,2-bis(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 4,4'-dicarboxybiphenyl, 4,4'-dicarboxydiphenyl ether, 4,4'-dicarboxytetraphenylsilane, bis(4-carboxyphenyl)sulfone, 2,2-bis(p-carboxyphenyl)propane, 5-tert-butylisophthalic acid, 5-bromoisophthalic acid, 5-fluoroisophthalic acid, 5-chloroisophthalic acid, 2,6-naphthalenedicarboxylic acid, malonic acid, dimethylmalonic acid, ethylmalonic acid, isopropylmalonic acid, di-n-butylmalonic acid, succinic acid, tetrafluorosuccinic acid, methylsuccinic acid, 2,2-dimethylsuccinic acid, 2,3-dimethylsuccinic acid, dimethylmethylsuccinic acid, glutaric acid, hexafluoroglutaric acid, 2-Methylglutaric acid, 3-methylglutaric acid, 2,2-dimethylglutaric acid, 3,3-dimethylglutaric acid, 3-ethyl-3-methylglutaric acid, adipic acid, octafluoroadipic acid, 3-methyladipic acid, octafluoroadipic acid, pimelic acid, 2,2,6,6-tetramethylpimelic acid, suberic acid, dodecafluorosuberic acid, azelaic acid, sebacic acid, hexadecafluorosebacic acid, 1,9-nonanedioic acid, dodecane diacid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanediacid, heneicosanediacid, docosanediacid, tricosanediacid, tetracosanediacid, pentacosanediacid, hexacosanediacid, heptacosanediacid, octacosanediacid, nonacosanediacid, triacontanedioic acid, hentriacontanedioic acid, dotriacontanedioic acid, diglycolic acid, etc. These may be used in combination.

[0151] Examples of hydroxyl group-containing diamines include 3,3'-diamino-4,4'-dihydroxybiphenyl, 4,4'-diamino-3,3'-dihydroxybiphenyl, bis(3-amino-4-hydroxyphenyl)propane, bis(4-amino-3-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(4-amino-3-hydroxyphenyl)sulfone, 2,2-bis(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis(4-amino-3-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, etc. These may be used in combination.

[0152] (B2) Photoacid generator The photoacid generator has a function of increasing the solubility of the light-irradiated portion in an alkaline aqueous solution. Examples of the photoacid generator include diazonaphthoquinone compounds, aryl diazonium salts, diaryliodonium salts, and triaryl sulfonium salts. Among these, diazonaphthoquinone compounds are preferred because of their high sensitivity.

[0153] (C) Additives The preferred types and amounts of additives are the same as those described in the section on the polyimide precursor composition.

[0154] (D) Solvent There are no particular limitations on the solvent as long as it can dissolve or disperse each component.

[0155] (E) Other The polybenzoxazole precursor composition may contain a crosslinker, a sensitizer, an adhesion promoter, a thermal acid generator, and the like.

[0156] (developing) After the polybenzoxazole precursor composition is exposed to light, unnecessary portions are washed away with a developer. The developer to be used is not particularly limited, but examples of the developer include aqueous alkali solutions such as sodium hydroxide, potassium hydroxide, sodium silicate, ammonia, ethylamine, diethylamine, triethylamine, triethanolamine, and tetramethylammonium hydroxide.

[0157] In the above, the positive type polybenzoxazole precursor composition has been mainly described. The polybenzoxazole precursor composition may be

[0158] (thermal curing) After development, the polybenzoxazole precursor composition is heated to ring-close the polybenzoxazole precursor and form polybenzoxazole, which becomes the cured relief pattern, i.e., the interlayer insulating film 6.

[0159] The heating temperature for thermal curing of the polybenzoxazole precursor composition is not particularly limited, but from the viewpoint of the influence on other members, the heating temperature is preferably low, and the heating temperature is preferably 250° C. or less, more preferably 230° C. or less, more preferably 200° C. or less, and particularly preferably 180° C. or less.

[0160] <Polybenzoxazole> The structure of the cured relief pattern formed from the polybenzoxazole precursor composition is represented by the following general formula (10).

[0161] [ka]

[0162] U and V in the general formula (10) are the same as U and V in the general formula (14). For the same reason, the preferred U and V in the general formula (14) are also preferred in the polybenzoxazole of the general formula (10).

[0163] <Polymer having phenolic hydroxyl group> (A) Photosensitive resin It is a resin having a phenolic hydroxyl group in the molecule and is soluble in alkali. Specific examples include vinyl polymers containing monomer units having a phenolic hydroxyl group, such as poly(hydroxystyrene), phenolic resins, poly(hydroxyamide), poly(hydroxyphenylene) ether, and polynaphthol.

[0164] Among these, phenolic resins are preferred because of their low cost and small volumetric shrinkage during curing, and novolac-type phenolic resins are particularly preferred.

[0165] Phenolic resins are polycondensation products of phenol or its derivatives with aldehydes. The polycondensation is carried out in the presence of a catalyst such as an acid or a base. Phenolic resins obtained using an acid catalyst are called novolak-type phenolic resins.

[0166] Examples of phenol derivatives include phenol, cresol, ethylphenol, propylphenol, butylphenol, amylphenol, benzylphenol, adamantanephenol, benzyloxyphenol, xylenol, catechol, resorcinol, ethylresorcinol, hexylresorcinol, hydroquinone, pyrogallol, phloroglucinol, 1,2,4-trihydroxybenzene, pararosolic acid, biphenol, bisphenol A, bisphenol AF, bisphenol B, bisphenol F, and bisphenol S. , dihydroxydiphenylmethane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,4-bis(3-hydroxyphenoxybenzene), 2,2-bis(4-hydroxy-3-methylphenyl)propane, α,α'-bis(4-hydroxyphenyl)-1,4-diisopropylbenzene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 2,2-bis(3-cyclohexyl-4-hydroxyphenyl)propane, 2,2-bis(2-hydroxy-5-biphenylyl)propane, and dihydroxybenzoic acid.

[0167] Examples of aldehyde compounds include formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, pivalaldehyde, butyraldehyde, pentanal, hexanal, trioxane, glyoxal, cyclohexylaldehyde, diphenylacetaldehyde, ethylbutyraldehyde, benzaldehyde, glyoxylic acid, 5-norbornene-2-carboxaldehyde, malondialdehyde, succindialdehyde, glutaraldehyde, salicylaldehyde, naphthaldehyde, and terephthalaldehyde.

[0168] The component (A) preferably contains (a) a phenolic resin having no unsaturated hydrocarbon groups and (b) a modified phenolic resin having an unsaturated hydrocarbon group. The component (b) is more preferably further modified by reaction of the phenolic hydroxyl group with a polybasic acid anhydride.

[0169] From the viewpoint of further improving the mechanical properties (elongation at break, elastic modulus, and residual stress), it is preferable to use a phenolic resin modified with a compound having an unsaturated hydrocarbon group having 4 to 100 carbon atoms as the component (b).

[0170] (b) The modified phenolic resin having an unsaturated hydrocarbon group is generally a reaction product of phenol or a derivative thereof with a compound having an unsaturated hydrocarbon group (preferably having 4 to 100 carbon atoms) (hereinafter sometimes simply referred to as an "unsaturated hydrocarbon group-containing compound") (hereinafter referred to as an "unsaturated hydrocarbon group-modified phenol derivative") and an aldehyde, or a reaction product of a phenolic resin and an unsaturated hydrocarbon group-containing compound.

[0171] The phenol derivatives used here may be the same as those described above as the raw material for the phenol resin as component (A).

[0172] From the viewpoints of adhesion and thermal shock resistance of a resist pattern, the unsaturated hydrocarbon group of the unsaturated hydrocarbon group-containing compound preferably contains two or more unsaturated groups. From the viewpoints of compatibility when made into a resin composition and flexibility of a cured film, the unsaturated hydrocarbon group-containing compound preferably has 8 to 80 carbon atoms, more preferably has 10 to 60 carbon atoms.

[0173] Examples of the unsaturated hydrocarbon group-containing compound include unsaturated hydrocarbons having 4 to 100 carbon atoms, polybutadiene having a carboxyl group, epoxidized polybutadiene, linoleyl alcohol, oleyl alcohol, unsaturated fatty acids, and unsaturated fatty acid esters. Suitable unsaturated fatty acids include crotonic acid, myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, erucic acid, nervonic acid, linoleic acid, α-linolenic acid, eleostearic acid, stearidonic acid, arachidonic acid, eicosapentaenoic acid, sardine acid, and docosahexaenoic acid. Among these, esters of unsaturated fatty acids having 8 to 30 carbon atoms and monohydric to trihydric alcohols having 1 to 10 carbon atoms are more preferred, and esters of unsaturated fatty acids having 8 to 30 carbon atoms and glycerin, which is a trihydric alcohol, are particularly preferred.

[0174] Esters of unsaturated fatty acids having 8 to 30 carbon atoms and glycerin are commercially available as vegetable oils. Vegetable oils include non-drying oils with an iodine value of 100 or less, semi-drying oils with an iodine value of more than 100 and less than 130, and drying oils with an iodine value of 130 or more. Examples of non-drying oils include olive oil, morning glory seed oil, cashew seed oil, camellia oil, camellia oil, castor oil, and peanut oil. Examples of semi-drying oils include corn oil, cottonseed oil, and sesame oil. Examples of drying oils include tung oil, linseed oil, soybean oil, walnut oil, safflower oil, sunflower oil, perilla oil, and mustard oil. In addition, processed vegetable oils obtained by processing these vegetable oils may be used.

[0175] Among the above vegetable oils, it is preferable to use non-drying oils in order to prevent gelation caused by excessive reaction in the reaction between phenol or its derivatives or phenol resin and vegetable oil, and to improve yield.On the other hand, it is preferable to use drying oils in order to improve the adhesion, mechanical properties and thermal shock resistance of the resist pattern.Among the drying oils, tung oil, linseed oil, soybean oil, walnut oil and safflower oil are preferable, and tung oil and linseed oil are more preferable, because they can more effectively and reliably exhibit the effects of the present invention.

[0176] These unsaturated hydrocarbon group-containing compounds may be used alone or in combination of two or more.

[0177] In preparing the component (b), first, the phenol derivative and the unsaturated hydrocarbon group-containing compound are reacted to prepare an unsaturated hydrocarbon group-modified phenol derivative. The reaction is preferably carried out at 50 to 130°C. From the viewpoint of improving the flexibility of the cured film (resist pattern), the reaction ratio of the phenol derivative and the unsaturated hydrocarbon group-containing compound is preferably 1 to 100 parts by mass, more preferably 5 to 50 parts by mass, of the unsaturated hydrocarbon group-containing compound per 100 parts by mass of the phenol derivative. If the amount of the unsaturated hydrocarbon group-containing compound is less than 1 part by mass, the flexibility of the cured film tends to decrease, and if it exceeds 100 parts by mass, the heat resistance of the cured film tends to decrease. In the above reaction, p-toluenesulfonic acid, trifluoromethanesulfonic acid, or the like may be used as a catalyst as necessary.

[0178] The unsaturated hydrocarbon group-modified phenol derivative produced by the above reaction is polycondensed with aldehydes to produce a phenol resin modified with an unsaturated hydrocarbon group-containing compound. The aldehydes may be the same as those mentioned above for obtaining the phenol resin.

[0179] The reaction between the aldehydes and the unsaturated hydrocarbon group-modified phenol derivative is a polycondensation reaction, and conventionally known synthesis conditions for phenolic resins can be used. The reaction is preferably carried out in the presence of a catalyst such as an acid or a base, and more preferably an acid catalyst is used. Examples of the acid catalyst include hydrochloric acid, sulfuric acid, formic acid, acetic acid, p-toluenesulfonic acid, and oxalic acid. These acid catalysts can be used alone or in combination of two or more.

[0180] The reaction is preferably carried out at a reaction temperature of 100 to 120°C. The reaction time varies depending on the type and amount of the catalyst used, but is usually 1 to 50 hours. After the reaction is completed, the reaction product is dehydrated under reduced pressure at a temperature of 200°C or less to obtain a phenolic resin modified with an unsaturated hydrocarbon group-containing compound. In addition, a solvent such as toluene, xylene, or methanol can be used for the reaction.

[0181] The phenol resin modified with an unsaturated hydrocarbon group-containing compound can also be obtained by polycondensing the above-mentioned unsaturated hydrocarbon group-modified phenol derivative with an aldehyde together with a compound other than phenol such as m-xylene. In this case, the molar ratio of the compound other than phenol to the compound obtained by reacting the phenol derivative with the unsaturated hydrocarbon group-containing compound is preferably less than 0.5.

[0182] The component (b) can also be obtained by reacting the phenolic resin of the component (a) with a compound containing an unsaturated hydrocarbon group.

[0183] The unsaturated hydrocarbon group-containing compound to be reacted with the phenol resin may be the same as the unsaturated hydrocarbon group-containing compound described above.

[0184] The reaction between the phenolic resin and the unsaturated hydrocarbon group-containing compound is preferably carried out at 50 to 130°C. In addition, the reaction ratio between the phenolic resin and the unsaturated hydrocarbon group-containing compound is preferably 1 to 100 parts by mass of the unsaturated hydrocarbon group-containing compound relative to 100 parts by mass of the phenolic resin, more preferably 2 to 70 parts by mass, and even more preferably 5 to 50 parts by mass, from the viewpoint of improving the flexibility of the cured film (resist pattern). If the amount of the unsaturated hydrocarbon group-containing compound is less than 1 part by mass, the flexibility of the cured film tends to decrease, and if it exceeds 100 parts by mass, the possibility of gelation during the reaction tends to increase, and the heat resistance of the cured film tends to decrease. At this time, p-toluenesulfonic acid, trifluoromethanesulfonic acid, or the like may be used as a catalyst as necessary. In addition, a solvent such as toluene, xylene, methanol, or tetrahydrofuran can be used for the reaction.

[0185] The phenolic hydroxyl groups remaining in the phenolic resin modified by the unsaturated hydrocarbon group-containing compound produced by the above method are further reacted with a polybasic acid anhydride. This allows the acid-modified phenolic resin to be used as component (b). By acid-modifying with a polybasic acid anhydride, a carboxyl group is introduced, further improving the solubility of component (b) in an alkaline aqueous solution (developer).

[0186] The polybasic acid anhydride is not particularly limited as long as it has an acid anhydride group formed by dehydration condensation of the carboxyl groups of a polybasic acid having a plurality of carboxyl groups. Examples of the polybasic acid anhydride include dibasic acid anhydrides such as phthalic anhydride, succinic anhydride, octenyl succinic anhydride, pentadodecenyl succinic anhydride, maleic anhydride, itaconic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, nadic anhydride, 3,6-endomethylenetetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, tetrabromophthalic anhydride and trimellitic anhydride, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, diphenylethertetracarboxylic dianhydride, butanetetracarboxylic dianhydride, cyclopentanetetracarboxylic dianhydride, pyromellitic anhydride and benzophenonetetracarboxylic dianhydride. These may be used alone or in combination of two or more. Among these, the polybasic acid anhydride is preferably a dibasic acid anhydride, more preferably one or more selected from the group consisting of tetrahydrophthalic anhydride, succinic anhydride, and hexahydrophthalic anhydride. In this case, there is an advantage that a resist pattern having a better shape can be formed.

[0187] In addition, the alkali-soluble resin (A) having a phenolic hydroxyl group can further contain a phenolic resin that has been acid-modified by reacting it with a polybasic acid anhydride. When the component (A) contains a phenolic resin that has been acid-modified with a polybasic acid anhydride, the solubility of the component (A) in an aqueous alkali solution (developer) is further improved.

[0188] Examples of the polybasic acid anhydride include dibasic acid anhydrides such as phthalic anhydride, succinic anhydride, octenyl succinic anhydride, pentadodecenyl succinic anhydride, maleic anhydride, itaconic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, methyl hexahydrophthalic anhydride, nadic anhydride, 3,6-endo methylene tetrahydrophthalic anhydride, methyl end methylene tetrahydrophthalic anhydride, tetrabromo phthalic anhydride, and trimellitic anhydride, and aliphatic and aromatic tetrabasic acid dianhydrides such as biphenyl tetracarboxylic acid dianhydride, naphthalene tetracarboxylic acid dianhydride, diphenyl ether tetracarboxylic acid dianhydride, butane tetracarboxylic acid dianhydride, cyclopentane tetracarboxylic acid dianhydride, pyromellitic anhydride, and benzophenone tetracarboxylic acid dianhydride. These may be used alone or in combination of two or more. Among these, the polybasic acid anhydride is preferably a dibasic acid anhydride, and more preferably, for example, one or more selected from the group consisting of tetrahydrophthalic anhydride, succinic anhydride, and hexahydrophthalic anhydride.

[0189] (B2) Photoacid generator Examples of the photoacid generator include diazonaphthoquinone compounds, aryl diazonium salts, diaryliodonium salts, triarylsulfonium salts, etc. Among these, diazonaphthoquinone compounds are preferred because of their high sensitivity.

[0190] (C) Additives The preferred types and amounts of additives are the same as those described in the section on the polyimide precursor composition.

[0191] (D) Solvent There are no particular limitations on the solvent as long as it can dissolve or disperse each component.

[0192] (E) Other It may contain a thermal crosslinking agent, a sensitizer, an adhesive assistant, a dye, a surfactant, a dissolution promoter, a crosslinking promoter, etc. Among these, by containing a thermal crosslinking agent, when the photosensitive resin film after pattern formation is heated and cured, the thermal crosslinking agent component reacts with the (A) component to form a crosslinked structure. This allows curing at a low temperature, and prevents the film from becoming brittle or melting. Specifically, the thermal crosslinking agent component may preferably be a compound having a phenolic hydroxyl group, a compound having a hydroxymethylamino group, or a compound having an epoxy group.

[0193] (developing) After the polymer having a phenolic hydroxyl group is exposed to light, unnecessary portions are washed away with a developer. There are no particular limitations on the developer used, but for example, an alkaline aqueous solution of sodium hydroxide, potassium hydroxide, sodium silicate, ammonia, ethylamine, diethylamine, triethylamine, triethanolamine, tetramethylammonium hydroxide (TMAH), or the like is preferably used.

[0194] (thermal curing) After development, the polymer having a phenolic hydroxyl group is heated to thermally crosslink the polymers having a phenolic hydroxyl group. The crosslinked polymer becomes a cured relief pattern, that is, an interlayer insulating film 6.

[0195] The heating temperature for thermal curing of the polymer having a phenolic hydroxyl group is not particularly limited, but from the viewpoint of the influence on other members, the heating temperature is preferably low, and the heating temperature is preferably 250° C. or less, more preferably 230° C. or less, more preferably 200° C. or less, and particularly preferably 180° C. or less.

[0196] (Method of manufacturing a semiconductor device) The manufacturing method of the semiconductor device in this embodiment will be described with reference to FIG. 3. FIG. 3 shows an example of the manufacturing process of the semiconductor device in this embodiment. In FIG. 3A, a pre-processed wafer 10 is prepared. Then, in FIG. 3B, the pre-processed wafer 10 is diced to form a plurality of semiconductor chips 2. The semiconductor chips 2 may be purchased. The semiconductor chips 2 thus prepared are attached at predetermined intervals on a support 11 as shown in FIG. 3C.

[0197] Next, the molding resin 12 is applied from above the semiconductor chip 2 to above the support 11, and mold sealing is performed as shown in FIG. 3D. Next, the support 11 is peeled off, and the molding resin 12 is inverted (see FIG. 3E). As shown in FIG. 3E, the semiconductor chip 2 and the molding resin 12 appear on approximately the same plane. Next, in the process shown in FIG. 3F, a photosensitive resin composition 13 is applied onto the semiconductor chip 2 and the molding resin 12. Then, the applied photosensitive resin composition 13 is exposed and developed to form a relief pattern (relief pattern forming process). The photosensitive resin composition 13 may be either a positive type or a negative type. Furthermore, the relief pattern is heated to form a cured relief pattern (interlayer insulating film forming process). Furthermore, wiring is formed in the places where the cured relief pattern is not formed (wiring forming process).

[0198] In this embodiment, the above-mentioned relief pattern forming step, interlayer insulating film forming step, and wiring forming step are combined into a rewiring layer forming step for forming a rewiring layer connected to the semiconductor chip 2.

[0199] The interlayer insulating film in the rewiring layer may be multi-layered, and therefore the rewiring layer forming process may include a relief pattern forming process multiple times, an interlayer insulating film forming process multiple times, and a wiring forming process multiple times.

[0200] Then, in Fig. 3G, a plurality of external connection terminals 7 corresponding to each semiconductor chip 2 are formed (bump formation), and dicing is performed between each semiconductor chip 2. This makes it possible to obtain a semiconductor device (semiconductor IC) 1 as shown in Fig. 3H. In this embodiment, a plurality of fan-out type semiconductor devices 1 can be obtained by the manufacturing method shown in Fig. 3.

[0201] In this embodiment, the refractive index difference of the cured relief pattern (interlayer insulating film) formed through the above process can be less than 0.0150. Here, the i-line transmittance of the interlayer insulating film can be adjusted by the amount of additive.

[0202] In the present embodiment, in the above-mentioned interlayer insulating film forming step, it is preferable to form the interlayer insulating film from a photosensitive resin composition capable of forming at least one compound selected from the group consisting of polyimide, polybenzoxazole, and a polymer having a phenolic hydroxyl group. EXAMPLES

[0203] Examples performed to clarify the effects of the present invention will now be described. In the examples, the following materials and measurement methods were used.

[0204] Examples performed to clarify the effects of the present invention will now be described.

[0205] (Polymer A-1: ​​Synthesis of polyimide precursor) 4,4'-oxydiphthalic dianhydride (ODPA) was placed in a 2-liter separable flask as a tetracarboxylic dianhydride. 2-Hydroxyethyl methacrylate (HEMA) and γ-butyrolactone were then added and stirred at room temperature, and pyridine was added while stirring to obtain a reaction mixture. After the heat generated by the reaction had ceased, the mixture was allowed to cool to room temperature and left to stand for 16 hours.

[0206] Next, under ice cooling, a solution of dicyclohexylcarbodiimide (DCC) dissolved in γ-butyrolactone was added to the reaction mixture over 40 minutes while stirring. Next, a suspension of 4,4'-diaminodiphenyl ether (DADPE) as a diamine in γ-butyrolactone was added over 60 minutes while stirring. After further stirring at room temperature for 2 hours, ethyl alcohol was added and stirred for 1 hour, and then γ-butyrolactone was added. The precipitate formed in the reaction mixture was removed by filtration to obtain a reaction liquid.

[0207] The obtained reaction solution was added to ethyl alcohol to produce a precipitate consisting of a crude polymer. The produced crude polymer was filtered off and dissolved in tetrahydrofuran to obtain a crude polymer solution. The obtained crude polymer solution was dropped into water to precipitate the polymer, and the resulting precipitate was filtered off and then vacuum dried to obtain a powdered polymer (polyimide precursor (polymer A-1)). The masses of the compounds used in component A-1 are shown in Table 1 below.

[0208] (Synthesis of Polymers A-2 to A-4) The reaction was carried out in the same manner as in the above-mentioned Polymer A-1, except that the tetracarboxylic dianhydride and diamine were changed as shown in Table 1 below, to obtain polyimide precursors (Polymers A-2 to A-4).

[0209] (Polymer B-1: Synthesis of polybenzoxazole precursor) In a 0.5-liter flask equipped with a stirrer and a thermometer, 15.48 g of 4,4'-diphenyl ether dicarboxylic acid as a dicarboxylic acid and N-methylpyrrolidone were charged. After cooling the flask to 5°C, thionyl chloride was added dropwise and reacted for 30 minutes to obtain a solution of dicarboxylic acid chloride. Next, N-methylpyrrolidone was charged into a 0.5-liter flask equipped with a stirrer and a thermometer. After stirring and dissolving 18.30 g of bis(3-amino-4-hydroxyphenyl)hexafluoropropane as bisaminophenol and 2.18 g of m-aminophenol, pyridine was added. Then, while maintaining the temperature at 0 to 5°C, the solution of dicarboxylic acid chloride was added dropwise over 30 minutes, and stirring was continued for 30 minutes. The solution was poured into 3 liters of water, the precipitate was collected, washed three times with pure water, and then dried under reduced pressure to obtain a polymer (polybenzoxazole precursor (polymer B-1)). The masses of the compounds used in polymer B-1 are as shown in Table 1 below.

[0210] (Synthesis of Polymers B-2 to B-3) The reaction was carried out in the same manner as the method described for polymer B-1 above, except that the dicarboxylic acid and bisaminophenol were changed as shown in Table 1 below, to obtain polybenzoxazole precursors (polymers B-2 to B-3).

[0211] (Synthesis of Polymer C-1: Phenolic Resin) A phenolic resin containing 85 g of C1 resin shown below and 15 g of C2 resin shown below was prepared as polymer C-1. C1: Cresol novolak resin (cresol / formaldehyde novolak resin, m-cresol / p-cresol (molar ratio) = 60 / 40, polystyrene-equivalent weight average molecular weight = 12,000, manufactured by Asahi Organic Chemical Industry Co., Ltd., trade name "EP4020G")

[0212] C2: C2 was synthesized as follows. <Synthesis of Phenolic Resin Modified with a Compound Having an Unsaturated Hydrocarbon Group with 4 to 100 Carbon Atoms> 100 parts by mass of phenol, 43 parts by mass of linseed oil, and 0.1 parts by mass of trifluoromethanesulfonic acid were mixed and stirred at 120°C for 2 hours to obtain a vegetable oil-modified phenol derivative (a). Next, 130 g of the vegetable oil-modified phenol derivative (a), 16.3 g of paraformaldehyde, and 1.0 g of oxalic acid were mixed and stirred at 90°C for 3 hours. Next, the temperature was raised to 120°C and stirred under reduced pressure for 3 hours, after which 29 g of succinic anhydride and 0.3 g of triethylamine were added to the reaction liquid and stirred at 100°C under atmospheric pressure for 1 hour. The reaction liquid was cooled to room temperature to obtain a phenol resin (hereinafter referred to as "C2 resin") modified with a compound having an unsaturated hydrocarbon group having 4 to 100 carbon atoms, which is the reaction product (acid value 120 mgKOH / g).

[0213] (Synthesis of Polymer C-2) 100 g of the following C1 resin was prepared as polymer C-2.

[0214] [Table 1]

[0215] [Examples 1 to 11, Comparative Examples 1 to 2] A solution of a photosensitive resin composition was obtained by mixing the ingredients as shown in Table 2 below. The units in Table 2 are parts by mass.

[0216] Using the compounds shown in Table 2 in the amounts shown in Tables 3 and 4, photosensitive resin compositions of Examples 1 to 11 and Comparative Examples 1 and 2 were prepared.

[0217] The prepared photosensitive resin composition was subjected to (1) a refractive index difference measurement test, (2) a reflow resistance test of an encapsulant, and (3) a test of adhesion to an encapsulant. The results of each test are shown in Table 3 below.

[0218] (1) Refractive index difference measurement test A fan-out type wafer-level chip size package type semiconductor device was manufactured using the photosensitive resin composition prepared in the examples and comparative examples. An interlayer insulating film having a thickness of 10 μm was removed as cleanly as possible from the manufactured semiconductor device. The difference between the in-plane refractive index and the out-of-plane refractive index of the removed interlayer insulating film was measured using a prism coupler device (PC-2010) manufactured by METRICON at a measurement wavelength of 1310 nm.

[0219] (2) Reflow resistance test of sealing material As an epoxy-based sealing material, we prepared the R4000 series manufactured by Nagase Chemtex Co., Ltd. Next, the sealing material was spin-coated onto an aluminum-sputtered silicone wafer to a thickness of approximately 150 μm, and then thermally cured at 130° C. to harden the epoxy-based sealing material.

[0220] The photosensitive resin compositions prepared in the Examples and Comparative Examples were applied onto the above-mentioned epoxy-based cured film so that the final film thickness was 10 μm. The applied photosensitive resin compositions were applied at 200 mJ / cm for Examples 1 to 4 and 10 and Comparative Example 1. 2 , Examples 5 to 7, 11, and Comparative Example 2 are 500 mJ / cm 2 After the entire surface was exposed under the above exposure conditions, it was thermally cured at 150° C. for 4 hours to form a first cured film having a thickness of 10 μm.

[0221] The photosensitive resin composition used in forming the first cured film was applied onto the first cured film, and the entire surface was exposed to light under the same conditions as when the first cured film was formed, followed by thermal curing to form a second cured film having a thickness of 10 μm.

[0222] The test piece after the formation of the second layer of cured film was heated to a peak temperature of 260°C in a nitrogen atmosphere under simulated solder reflow conditions using a mesh belt type continuous firing furnace (Koyo Thermo Systems, model number 6841-20AMC-36). The simulated reflow conditions were standardized by assuming a high solder melting point of 220°C in accordance with the solder reflow conditions described in Section 7.6 of IPC / JEDEC J-STD-020A, the standard set by the US semiconductor industry group regarding evaluation methods for semiconductor devices.

[0223] The cured film after the above-mentioned simulated reflow treatment was cut into a cross section using a FIB device (JIB-4000, manufactured by JEOL Ltd.), and the presence or absence of voids in the epoxy part was checked to evaluate the degree of deterioration. Those with no voids were marked with ○, and those with at least one void were marked with ×.

[0224] (3) Adhesion test with sealing material A pin was placed on the photosensitive resin cured film of the sample prepared in the test (2), and an adhesion test was performed using a pull tester (Quad Group, Sebastian Model 5). Evaluation: Adhesive strength 70MPa or more.....Adhesion strength ◎ 50MPa or more - less than 70MPa...Adhesion strength: Yes 30MPa or more - less than 50MPa...Adhesion strength △ Less than 30MPa...Adhesion strength ×

[0225] [Table 2]

[0226] [Table 3]

[0227] [Table 4]

[0228] As is clear from Tables 3 and 4, the results of tests (1) to (3) performed on the photosensitive resin compositions of Examples 1 to 11 confirmed that when the refractive index difference was less than 0.0150, no voids were observed in the epoxy portion in the reflow resistance test of the encapsulant, and the adhesion strength was evaluated as ◎, ○, or △ in the adhesion test with the encapsulant.

[0229] On the other hand, as is clear from Tables 3 and 4, the results of tests (1) to (3) performed on the photosensitive resin compositions of Comparative Examples 1 and 2 showed that when the refractive index difference exceeded 0.0150, voids were observed in the epoxy portion in the reflow resistance test of the encapsulant, and the adhesion was evaluated as × in the adhesion test with the encapsulant.

[0230] Furthermore, when a fan-out type wafer-level chip size package type semiconductor device containing an epoxy resin in the molding resin was fabricated using the photosensitive resin compositions of Examples 1 to 11, it operated without any problems. [Industrial Applicability]

[0231] The present invention is preferably applied to a semiconductor device having a semiconductor chip and a rewiring layer connected to the semiconductor chip, and in particular to a fan-out type wafer level chip size package type semiconductor device. [Explanation of symbols]

[0232] 1 Semiconductor device 2. Semiconductor chips 3. Encapsulating material 4 Redistribution layer 5. Wiring 6 Interlayer insulating film 7 External connection terminal 10 Wafers 11 Support 12 Molding resin 13 Photosensitive resin composition

Claims

1. A semiconductor chip; a sealing material in contact with the semiconductor chip; a redistribution layer having an area larger than that of the semiconductor chip in a plan view; the sealing material has a portion in direct contact with the interlayer insulating film of the redistribution layer; The absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer at a wavelength of 1310 nm is less than 0.0150. A semiconductor device comprising:

2. A semiconductor chip; a sealing material in contact with the semiconductor chip; In a semiconductor device including a redistribution layer having an area larger than that of the semiconductor chip in a plan view, an interlayer insulating film used for forming the redistribution layer, in direct contact with the encapsulant; The absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the interlayer insulating film of the redistribution layer at a wavelength of 1310 nm is less than 0.0150. An interlayer insulating film characterized by:

3. 3. The semiconductor device or the interlayer insulating film according to claim 1, wherein the sealing material contains an epoxy resin.

4. 4. The semiconductor device or the interlayer insulating film according to claim 1, wherein the interlayer insulating film contains at least one selected from the group consisting of polyimide, polybenzoxazole, and a polymer having a phenolic hydroxyl group.

5. 5. The semiconductor device or the interlayer insulating film according to claim 4, wherein the interlayer insulating film contains a polyimide having a structure represented by the following general formula (1): 【Chemistry 1】 (In general formula (1), X １ is a tetravalent organic group, Y １ is a divalent organic group, and m is an integer of 1 or more.

6. X in the general formula (1) １ is a tetravalent organic group containing an aromatic ring, Y in the general formula (1) １ 6. The semiconductor device or interlayer insulating film according to claim 5, wherein: is a divalent organic group containing an aromatic ring.

7. X in the general formula (1) １ The semiconductor device or interlayer insulating film according to claim 5 or 6, characterized in that it contains at least one structure represented by the following general formula (2) to general formula (4). 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 (In general formula (4), R 9 is an oxygen atom, a sulfur atom, or a divalent organic group.

8. X in the general formula (1) １ The semiconductor device or interlayer insulating film according to claim 7, characterized in that it contains a structure represented by the following general formula (5): 【Chemistry 5】

9. Y in the general formula (1) １ The semiconductor device or interlayer insulating film according to any one of claims 5 to 8, characterized in that it contains at least one structure represented by the following general formulas (6) to (8): 【Chemistry 6】 (R １０ , R １１ , R １２ and R １３ are hydrogen atoms, monovalent aliphatic groups having 1 to 5 carbon atoms, or hydroxyl groups, and may be the same or different. 【Chemistry 7】 (R １４ ~R ２１ are hydrogen atoms, halogen atoms, monovalent organic groups having 1 to 5 carbon atoms, or hydroxyl groups, and may be different or the same. 【Chemistry 8】 (R ２２ is a divalent group, R ２３ ~R ３０ are hydrogen atoms, halogen atoms, monovalent aliphatic groups having 1 to 5 carbon atoms, or hydroxyl groups, and may be the same or different.

10. Y in the general formula (1) １ The semiconductor device or interlayer insulating film according to claim 9 , characterized in that it contains a structure represented by the following general formula (9): 【Chemistry 9】

11. 5. The semiconductor device or interlayer insulating film according to claim 4, wherein the polybenzoxazole comprises a polybenzoxazole having a structure represented by the following general formula (10): 【Chemistry 10】 (In general formula (10), U and V are divalent organic groups.)

12. 12. The semiconductor device or interlayer insulating film according to claim 11, wherein U in the general formula (10) is a divalent organic group having 1 to 30 carbon atoms.

13. 13. The semiconductor device or interlayer insulating film according to claim 12, wherein U in the general formula (10) is a chain alkylene group having 1 to 8 carbon atoms and in which some or all of the hydrogen atoms are substituted with fluorine atoms.

14. 14. The semiconductor device or interlayer insulating film according to claim 11, wherein V in the general formula (10) is a divalent organic group containing an aromatic group.

15. 15. The semiconductor device or interlayer insulating film according to claim 14, wherein V in the general formula (10) includes at least one structure represented by the following general formulas (6) to (8): 【Chemistry 11】 (R １０ , R １１ , R １２ and R １３ are hydrogen atoms or monovalent aliphatic groups having 1 to 5 carbon atoms, and may be the same or different. 【Chemistry 12】 (R １４ ~R ２１ are hydrogen atoms, halogen atoms, or monovalent organic groups having 1 to 5 carbon atoms, and may be different or the same. 【Chemistry 13】 (R ２２ is a divalent group, R ２３ ~R ３０ are hydrogen atoms, halogen atoms, or monovalent aliphatic groups having 1 to 5 carbon atoms, and may be the same or different.

16. 16. The semiconductor device or interlayer insulating film according to claim 15, wherein V in the general formula (10) includes a structure represented by the following general formula (9): 【Chemistry 14】

17. 14. The semiconductor device or interlayer insulating film according to claim 11, wherein V in the general formula (10) is a divalent organic group having 1 to 40 carbon atoms.

18. 18. The semiconductor device or interlayer insulating film according to claim 17, wherein V in the general formula (10) is a divalent chain aliphatic group having 1 to 20 carbon atoms.

19. 5. The semiconductor device or interlayer insulating film according to claim 4, wherein the polymer having a phenolic hydroxyl group includes a novolac type phenolic resin.

20. 5. The semiconductor device or interlayer insulating film according to claim 4, wherein the polymer having a phenolic hydroxyl group includes a phenol resin having no unsaturated hydrocarbon group and a modified phenol resin having an unsaturated hydrocarbon group.

21. 21. The semiconductor device or interlayer insulating film according to claim 1, wherein the redistribution layer includes, when viewed in cross section, a first interlayer insulating film layer, a second interlayer insulating film layer, and an intermediate layer that is a layer different from the first interlayer insulating film layer and the second interlayer insulating film layer and is provided between the first interlayer insulating film layer and the second interlayer insulating film layer.

22. The semiconductor device or interlayer insulating film according to claim 21, characterized in that the first interlayer insulating film layer is in contact with the sealing material, and the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the first interlayer insulating film layer is less than 0.0150.

23. 23. The semiconductor device or interlayer insulating film according to claim 21, wherein the second interlayer insulating film layer has a different composition from the first interlayer insulating film layer.

24. 24. The semiconductor device or interlayer insulating film according to claim 21, wherein the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the second interlayer insulating film layer is different from the absolute value of the difference between the in-plane refractive index and the out-of-plane refractive index of the first interlayer insulating film layer.

25. 25. The semiconductor device or interlayer insulating film according to claim 1, wherein the semiconductor device is a fan-out type wafer level chip size package type semiconductor device.

26. 26. The semiconductor device or interlayer insulating film according to claim 1, wherein an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0145 or less.

27. 27. The semiconductor device or interlayer insulating film according to claim 26, wherein an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0140 or less.

28. 27. The semiconductor device or interlayer insulating film according to claim 26, wherein an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0135 or less.

29. 27. The semiconductor device or interlayer insulating film according to claim 26, wherein an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0130 or less.

30. 27. The semiconductor device or interlayer insulating film according to claim 26, wherein an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0120 or less.

31. 31. The semiconductor device or interlayer insulating film according to claim 1, wherein an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0005 or more.

32. 32. The semiconductor device or interlayer insulating film according to claim 31, wherein an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0010 or more.

33. 32. The semiconductor device or interlayer insulating film according to claim 31, wherein an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film of the redistribution layer is 0.0015 or more.

34. forming an encapsulant on the semiconductor chip; forming a redistribution layer having an area larger than that of the semiconductor chip in a plan view and including an interlayer insulating film, and at this time, bringing the sealing material into direct contact with the interlayer insulating film of the redistribution layer; a second insulating film formed on the first insulating film and having an in-plane refractive index different from that of the first insulating film;

35. 35. The method for manufacturing a semiconductor device according to claim 34, further comprising the step of forming the interlayer insulating film from a photosensitive resin composition capable of forming at least one compound selected from the group consisting of polyimide, polybenzoxazole, and a polymer having a phenolic hydroxyl group.

36. 36. The method for manufacturing a semiconductor device according to claim 35, wherein the interlayer insulating film forming step includes a step of forming the interlayer insulating film from the photosensitive resin composition adjusted with an additive so that an absolute value of a difference between an in-plane refractive index and an out-of-plane refractive index of the interlayer insulating film is less than 0.0150.

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