JPH10182822A - Polyester-amide-imide resin, its precursor and their production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an essentially thermoplastic polyester-amide-imide resin excellent in heat resistance and solvent solubility, desirable as a die bonding agent and capable of low temperature processing by cyclizing a precursor being a reaction product of a polyamide obtained from a specified dicarboxylic acid and a diamine with a specified tetracarbocylic acid dianhydride and a diamine into an imide. SOLUTION: This resin contains 40-90mol%, based on the total repeating units, repeating units of formula I and 5-20mol% repeating units of formula II. In the formulas, R<1> and R<2> are each an organic group; m is 2-20; and n is 4-12. The units of formula II contribute to the improvement of solvent solubility and the lowering of a glass transition temperature and improve the reflow crack resistance and adhesion of a semiconductor adhesive. This imide is obtained by cyclizing a precursor obtained by reacting a polyamide obtained from a dicarboxylic acid of formula II and a diamine with a tetracarboxylic acid dianhydride of formula IV and a diamine into an imide. In the formulas, n is 4-12; R<1> is a divalent organic group; and m is 2-20.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a polyesteramide imide resin, a precursor thereof, and a method for producing the same.

[0002]

2. Description of the Related Art In recent years, there has been an increasing demand for reliability of semiconductor devices such as ICs. On the other hand, as packages are becoming thinner and smaller, they are mounted on substrates by the so-called surface mounting method. However, since infrared reflow furnaces are used, the heat load on semiconductor devices is even more severe. It has become. From such a situation, the moisture absorbed inside the semiconductor device in the reflow furnace at the time of mounting expands, peels off the sealing material, and causes cracks in the semiconductor device (hereinafter, referred to as “the semiconductor device”).
The phenomenon is expressed as reflow crack).

In an IC manufacturing process, a semiconductor element is bonded to a so-called die pad, which is a part of a lead frame, by using an adhesive to hold and fix the semiconductor element (hereinafter, this step is referred to as die bonding). ). In a subsequent step, the semiconductor element is electrically connected to the lead frame (wire bonding step). At this time, since the semiconductor element is connected with a gold wire, the semiconductor element is generally heated to a temperature close to 300 ° C.

As an adhesive for die bonding, an adhesive (die bonding material) such as a so-called silver paste in which a thermosetting epoxy resin is filled with a filler such as silver powder is widely used. These die bonding materials are widely used because they are liquid and easy to apply, and form an adhesive layer having excellent heat resistance in a short time.

However, the epoxy resin-based die bonding material generates a large amount of volatile components and thermal decomposition gas during curing, and contaminates the periphery of the chip, deteriorating the adhesion with the sealing material, and the amount of water absorbed by the adhesive. However, there is a problem that reflow cracks are easily caused. In particular, when the size of the chip used increases, reflow cracks are more likely to occur due to an increase in water absorption and an increase in thermal stress accompanying curing shrinkage.

On the other hand, aromatic polyimides are used in various forms in semiconductor devices because of their excellent heat resistance and electrical characteristics. Have also been studied in various ways. However, conventional aromatic polyimides with high heat resistance do not dissolve in general-purpose solvents, so they are applied in the form of polyamic acid and imidized over a long period of time, or the polyimide once processed into a film is bonded to the chip. In addition, it is necessary to adhere to the lead frame, so that the process becomes complicated and the productivity is inferior.In addition, since a very high processing temperature exceeding the temperature of the wire bonding process is required, it is susceptible to oxidation deterioration such as a copper frame. There is a problem that it cannot be used with a metal frame.

[0007]

As described above, epoxy resins conventionally used as die bonding materials have problems in heat resistance, resistance to reflow cracks, and the like. There are problems such as low heat resistance and high processing temperature. The present invention provides a novel polyimide resin that solves these problems.

That is, the first aspect of the present invention is essentially thermoplastic, is suitable as an adhesive for a semiconductor device, has excellent heat resistance and solvent solubility, and can be processed at a relatively low temperature. A polyester amide imide resin is provided. According to a second aspect of the present invention, there is provided a polyester amide imide resin exhibiting more excellent solvent solubility, processing characteristics and the like in addition to the effects of the first aspect of the present invention. The invention according to claim 3 is
A polyester amide imide resin precursor capable of producing the polyester amide imide resin having excellent heat resistance according to claim 1 is provided. The invention described in claim 4 provides a polyesteramide imide resin precursor capable of producing the polyester amide imide resin having excellent heat resistance described in claim 2. The invention described in claim 5 provides a method for efficiently producing a precursor of a polyesteramideimide resin having excellent heat resistance and the like. The invention according to claim 6 provides a method for efficiently producing a polyesteramideimide resin having excellent heat resistance and the like.

[0009]

The present invention provides a compound represented by the general formula (I):

Embedded image (Wherein, R ¹ represents a divalent organic group, m represents an integer of 2 to 20) and a general formula (II)

Embedded image (Wherein, R ² represents a divalent organic group, and n represents an integer of 4 to 12).

In the present invention, the amount of the repeating unit represented by the general formula (I) is 40 to 90 mol% of the total amount of the repeating unit of the polyesteramide imide resin, and the repeating unit represented by the general formula (II) is used. Is 5 to 20 mol% of the total repeating unit of the polyesteramide imide resin.

The present invention also relates to a compound represented by the general formula (III):

Embedded image (Wherein, R ¹ represents a divalent organic group, and m represents an integer of 2 to 20) and the above-mentioned general formula (I
It relates to a polyesteramide imide resin precursor having a repeating unit represented by I).

In the present invention, the amount of the repeating unit represented by the general formula (III) is 40 to 90 mol% of the total amount of the repeating unit of the polyesteramide imide resin precursor,
The amount of the repeating unit represented by the general formula (II) is 5% of the total amount of the repeating unit of the polyesteramideimide resin precursor.
About 20 mol% of the polyesteramide imide resin precursor.

The present invention also provides a compound of the formula (IV)

Embedded image (Where n represents an integer of 4 to 12) to produce a polyamide by reacting a dicarboxylic acid and a diamine represented by the formula:
Next, this is represented by the general formula (V)

Embedded image (Wherein, R ¹ represents a divalent organic group, and m represents an integer of 2 to 20), and is reacted with a tetracarboxylic dianhydride and a diamine. It relates to the method of manufacturing the body. Furthermore, the present invention relates to a method for producing a polyesteramide imide resin, wherein the polyesteramide imide resin precursor is subjected to imide ring closure.

[0014]

BEST MODE FOR CARRYING OUT THE INVENTION The polyesteramide imide resin of the present invention has a repeating unit represented by the above general formula (I).
The tetracarboxylic dianhydride represented by the general formula (V) may be used as an acid component.

Such tetracarboxylic dianhydrides include 1,2- (ethylene) bis (trimellitate dianhydride), 1,3- (trimethylene) bis (trimellitate dianhydride), 1,4- ( Tetramethylene) bis (trimellitate dianhydride), 1,5- (pentamethylene) bis (trimellitate dianhydride), 1,6- (hexamethylene) bis (trimellitate dianhydride), 1,7- (heptamethylene ) Bis (trimellitate dianhydride), 1,
8- (octamethylene) bis (trimellitate dianhydride), 1,9- (nonamethylene) bis (trimellitate dianhydride), 1,10- (decamethylene) bis (trimellitate dianhydride), 1,12- (dodeca) Methylene) bis (trimellitate dianhydride), 1,16- (hexadecamethylene) bis (trimellitate dianhydride), 1,1
8- (octadecamethylene) bis (trimellitate dianhydride) and the like may be used in combination.

These are preferably used in an amount of from 40 to 95 mol% based on the total amount of the carboxylic acid component used in the polyesteramide imide resin, from the viewpoint of heat resistance of the resin.
It is more preferable to use 90 mol%. That is, the repeating unit represented by the general formula (I) preferably accounts for 40 to 95 mol%, more preferably 60 to 90 mol% of the total amount of the repeating units of the polyesteramideimide resin. Here, the repeating unit refers to a unit of a chain of one molecule of diamine and one molecule of tetracarboxylic acid or dicarboxylic acid in the polyimide resin.

The polyesteramide imide resin of the present invention has a repeating unit represented by the general formula (II), whereby the solvent solubility of polyimide is improved,
Further, the glass transition temperature (hereinafter referred to as Tg) can be lowered, and as a semiconductor adhesive, reflow crack resistance and adhesiveness are excellent.

In order to have a repeating unit represented by the general formula (II), the dicarboxylic acid represented by the general formula (IV) may be used as a part of the acid component.

Such dicarboxylic acids include adipic acid (n = 4), pimelic acid (n = 5), suberic acid (n = 6), azelaic acid (n = 7), and sebacic acid (n
= 8), dodecane diacid (n = 12) and the like. These may be used in combination of two or more.

These are preferably used in an amount of 5 to 20 mol% of the total carboxylic acid component used for the polyesteramide imide resin, since the adhesive for semiconductors is excellent in reflow crack resistance and the like, and more preferably 8 to 15 mol%. . The repeating unit represented by the general formula (II) preferably accounts for 5 to 20 mol%, more preferably 8 to 15 mol% of the total amount of the repeating units of the polyesteramide imide resin.

Further, carboxylic acid components other than those described above can be used in combination.
4'-tetracarboxybenzophenone, bis (3,4
-Dicarboxyphenyl) dimethylsilane, 1,2,2
3,4-butanetetracarboxylic acid, bis (exo-bicyclo [2,2,1] heptane-2,3-dicarboxylic acid)
Sulfone, 2,2-bis (3,4-dicarboxyphenoxyphenyl) hexafluoropropane, 1,3-bis (2-hydroxyhexafluoroisopropyl) benzenebis (trimellitic acid), pyromellitic acid, 3,
3 ', 4,4'-biphenyltetracarboxylic acid, 2,
3,3 ', 4'-bensophenonetetracarboxylic acid,
2,3,6,7-tetracarboxynaphthalene, 2,
2′-bis (3,4-dicarboxyphenylpropane,
3,4,9,10-perylenetetracarboxylic acid, benzene-1,2,3,4-tetracarboxylic acid, 2,6-dichloronaphthalene-1,4,5,8 tetracarboxylic acid, pyrrolidine-2, Preferred are tetracarboxylic dianhydrides such as 3,4,5, -tetracarboxylic acid. Among them, 3,3 ', 4,4'-tetracarboxybenzophenone, bis (3,4-dicarboxyphenyl) dimethylsilane, 2,2-bis (3,4-
Dicarboxyphenoxyphenyl) hexafluoropropane and the like are preferable because they have a high effect of lowering the Tg of the obtained resin.

The divalent organic group represented by R ¹ or R ² in the structure represented by the general formula (I) or (II) is a group derived from a diamine component, and is not particularly limited. It is preferable to select the polyester amide imide so as to adjust the melt viscosity and the glass transition temperature so as to satisfy the properties such as excellent heat resistance of the polyester amide imide resin.

As the diamine, 2,2-bis (3
-Aminophenyl) propane, 2,2-bis (4- (4
-Aminophenoxy) phenyl) propane, 4,4'-
(Or 3,3'-, 3,4'-, 2,4'-, 2,2 '
-) Diaminodiphenyl ether, 4,4'- (or 3,3'-, 3,4'-, 2,4'-, 2,2'-) diaminodiphenylmethane, 4,4'- (or 3,3 '
-, 3,4'-, 2,4'-, 2,2'-) diaminodiphenylsulfone, 4,4'- (or 3,3'-, 3,
4'-, 2,4'-, 2,2'-) diaminodiphenyl sulfide, 4,4'- (or 3,3'-, 3,4 '
Α, ω such as-, 2,4 '-, 2,2'-) diaminodiphenylsulfoxide, paraphenylenediamine, metaphenylenediamine, orthophenylenediamine, 1,6-diaminohexane, and 1,12-diaminododecane
-Diaminoalkane, m-xylylenediamine, 2,2
-Bis (3-aminophenyl) hexafluoropropane, 1,1-bis (4- (4-aminophenoxy) phenyl) cyclohexane, 1,3-bis (3-aminopropyl) tetramethyldisiloxane, 3,3 ′ -Diaminodiphenyldifluoromethane, 3,3'-diaminodiphenylketone and the like can be used, and among these, aromatic diamines are preferred. Of these, 1,12-diaminododecane, 3,3'-diaminodiphenyl ether, 3,3'-diaminodiphenylmethane, and the like are preferable because they have a high effect of lowering the Tg of the obtained resin.

As the raw material of the polyesteramideimide resin used in the present invention, the above-mentioned tetracarboxylic dianhydride, dicarboxylic acid and diamine are usually used. Generally, the proportions of carboxylic acid and amine are equivalent. Further, as a raw material, an acid component such as tetracarboxylic acid itself, a lower alcohol ester derived therefrom, an acid halide, an isocyanate compound capable of deriving a corresponding amine as an amine component, and a lower carboxylic acid amide can also be used. .

As a method for synthesizing the polyesteramideimide resin, a carboxylic acid anhydride and an amine are dissolved in a solvent capable of dissolving the polyesteramideimide resin of the present invention, for example, N-methylpyrrolidone having a boiling point of 150 ° C. or more. At room temperature to synthesize a polyamic acid as a precursor, and further heat this to dehydrate and close the polyamic acid. In this case, a polyesteramide imide resin precursor having a repeating unit represented by the general formula (III) and a repeating unit represented by the general formula (II) is obtained as an intermediate. In particular, the amount of the repeating unit represented by the general formula (III) is 40 to 90 mol% of the total amount of the repeating units of the polyesteramide imide resin precursor, and the amount of the repeating unit represented by the general formula (II) is It is preferable to obtain a polyesteramide imide resin precursor that is 5 to 20 mol% of the total amount of the repeating units of the resin precursor.

As a method for synthesizing the polyester amide imide resin, it is also possible to use a synthesis method such as a method of dehydrating and ring-closing using an acid anhydride such as acetic anhydride, or a method of reacting an acid anhydride with an isocyanate. As a method for producing the polyesteramide imide resin precursor of the present invention, the dicarboxylic acid and the diamine are reacted in excess of an amine to synthesize a polyamide having an amino terminal, and this is used as a part of the amine to obtain the above-mentioned general formula (V) The method of mixing with a tetracarboxylic anhydride and a diamine represented by the following formula and further promoting the reaction is preferable in that the dicarboxylic acid component can be efficiently incorporated into the resin.

The polyesteramide imide precursor obtained can be heated and subjected to ring closure by dehydration using a method of heat treatment at 120 to 250 ° C. or a chemical method.
In the case of the heat treatment method, the heat treatment can be usually performed while removing the water generated by the dehydration reaction out of the system. Examples of the chemical method include a method using a dehydrating agent such as acetic anhydride and cyclohexylcarbodiimide. In the polyester amide imide resin used in the present invention, it is preferable that all the repeating units are dehydrated and ring-closed to form imidization, but the repeating units of polyamic acid may remain in a part thereof. In this case, the content is preferably 20 mol% or less of the total amount of the repeating units of the polyesteramideimide resin. The polyesteramideimide resin of the present invention can be isolated by pouring the solution after synthesis into a poor solvent for the resin, such as methanol or water.

The obtained polyesteramide imide resin of the present invention preferably has a Tg of 80 to 200 ° C.,
Further, the melt viscosity at 300 ° C. is 200 to 10,000.
Pa · s is preferred. In the present invention, Tg
Is a heating rate of 10 ° C./min by DSC (differential scanning calorimeter)
Means the value measured in. If the Tg is lower than 80 ° C., the adhesive strength at high temperature tends to be insufficient as an adhesive, and the water absorption of the resin increases so that when used as an adhesive, the semiconductor device tends to cause reflow cracks. On the other hand, when Tg is 2
If the temperature exceeds 00 ° C, 300 ° C is required to obtain sufficient adhesive strength.
Tend to require higher bonding temperatures. From the viewpoint of these balances, Tg is more preferably adjusted to 80 to 150 ° C, and particularly preferably adjusted to 100 to 150 ° C.

The melt viscosity at 300 ° C. is 20
If the pressure is less than 0 Pa · s, the adhesive may flow out in the die bonding or wire bonding step as an adhesive for the semiconductor device, and contaminate the heating stage.
In the wire bonding process, a problem such as movement of the chip tends to occur. On the other hand, if it exceeds 10,000 Pa · s, the cohesive strength tends to be too high and sufficient adhesive strength cannot be obtained. From the viewpoint of these balances, the melt viscosity is preferably from 500 to 10,000 Pa · s,
0 to 8,000 Pa · s is more preferable.

The thus obtained polyesteramide imide resin of the present invention comprises cyclohexanone, xylene, TH
Since it can be dissolved in a general-purpose solvent such as F, it is possible to reduce the effects on the environment and workers in various applications.
Further, since the polyesteramideimide resin of the present invention is excellent in solvent solubility, the solid content concentration can be increased, and the drying time in applications such as adhesives can be shortened.

The polyesteramideimide resin of the present invention can be used, for example, as a resin solution as an adhesive suitable for bonding a semiconductor element of a semiconductor device and a metal frame. In this case, if necessary, a commonly used additive such as a silane coupling agent, a titanium coupling agent, and a metal acetylacetone complex may be added for the purpose of improving the adhesive strength of the adhesive at room temperature. Other polyimide resins, epoxy resins and the like can also be used in combination.

[0032]

The present invention will be described below in detail with reference to examples. Synthesis Example 1 Synthesis of Polyamide 180.0 g of water-free N-methylpyrrolidone and 120.0 g of xylene were put into a reactor equipped with a heating / cooling device, a stirring device, and a reflux device, and dried 2,2-
123.0 g of bis (4- (4-aminophenoxy) phenyl) propane (hereinafter referred to as BAPP) and 40.4 g of sebacic acid were added. The mixture was heated to 100 ° C. and reacted for 2 hours.
The polyamide solution was obtained by reacting at 0 ° C. for 3 hours. The solid content of the solution is 50% by weight, and the amino group equivalent of the polyamide calculated from the amino group content of the solution and the solid content is 80%.
It was 0 g / eq.

Example 1 Synthesis of polyesteramide imide precursor and polyester amide imide a 441.2 g of water-free N-methylpyrrolidone was placed in a reactor equipped with a heating and cooling device, a stirring device and a reflux device, and dried. 34.9 g of the obtained BAPP was dissolved, and 16.0 g of the polyamide solution synthesized in Synthesis Example 1 was further added. Further, 47.0 g of dried anhydrous decamethylene bistrimellitate (hereinafter referred to as DBTA) was added thereto while cooling the reactor to 20 ° C. or lower, and reacted for 4 hours to obtain a polyesteramideimide precursor solution. This is 180
The mixture was heated to ℃, the reflux device was kept at 120 ℃, and reacted for 3 hours to obtain a polyesteramideimide solution. The solution was poured into stirred water to precipitate polyesteramideimide, which was further dried at 80 ° C. under reduced pressure to obtain polyesteramideimide a. The glass transition temperature of the obtained polyester amide imide a was 118 ° C., and the melt viscosity at 300 ° C. was 1,200 Pa · s. The carboxylic acid component constituting the obtained polyimide a was measured by ¹³ C-NMR, a calibration curve was prepared and carbonyl carbon was quantified and determined (hereinafter, measured by the same method).
Mol%, sebacic acid 10 mol%. The melt viscosity was measured at a shear rate of 10 ³ sec to ¹ using a flow tester.

Example 2 Synthesis of polyester amide imide precursor and polyester amide imide b As materials, 441.2 g of N-methylpyrrolidone, BA
34.9 g of PP, polyamide solution 1 synthesized in Synthesis Example 1
6.0 g, DBTA 26.1 g and 2,3,3 ', 4'
-Polyester amide imide precursor and polyester amide imide b in the same manner as in Example 1 except that 15.5 g of tetracarboxydiphenyl ether was used as a raw material.
I got The glass transition temperature of the obtained polyesteramide imide b is 148 ° C., and the melt viscosity at 300 ° C. is 2
It was 200 Pa · s. The carboxylic acid components constituting the obtained polyester amide imide b were 50 mol% of DBTA, 10 mol% of sebacic acid, and 40 mol% of 2,3,3 ', 4'-tetracarboxydiphenyl ether.

Example 3 Synthesis of polyester amide imide precursor and polyester amide imide c As materials, 441.2 g of N-methylpyrrolidone,
12.4 g of 4'-bis (4,4'-bisaminophenoxy) acetophenone, 14.4 g of BAPP, 16.0 g of the polyamide solution synthesized in Synthesis Example 1 and 41.
Polyester amide imide c was obtained in the same manner as in Example 1 except that 8 g was used as a raw material. The glass transition temperature of the obtained polyester amide imide c is 135 ° C.,
The melt viscosity at 300 ° C. was 3000 Pa · s. The carboxylic acid component constituting the obtained polyesteramide imide c was 90 mol% of DBTA and 10 mol% of sebacic acid.

Comparative Example 1 Synthesis of polyimide d As materials, N-methylpyrrolidone 502.6 g, 3,
Polyimide d was obtained in the same manner as in Example 1 except that 24.8 g of 3'-diaminodiphenylsulfone and 31.0 g of 2,3,3 ', 4'-tetracarboxydiphenyl ether were used. The glass transition temperature of the obtained polyimide is 242 ° C., and the melt viscosity at 300 ° C. is 24.0 ° C.
It was 00 Pa · s.

Application Example A semiconductor device was manufactured by using the resin obtained in each of the above examples dissolved at a nonvolatile content shown in Table 1 as an adhesive and using the manufacturing apparatus shown in FIG. FIG. 1 is a conceptual diagram showing a part of a semiconductor device manufacturing apparatus used here. In FIG. 1, a metal frame 1 and a chip 2 are bonded. First, the metal frame 1 is moved to the position of the dispenser 4 by the transport device 3 and the adhesive 5 is applied. Adhesive 5
Is further moved, heated by the heating stage 6 and the solvent of the adhesive is evaporated to form a polyimide layer. Next, the metal frame 1 is heated in a die bonder 8 having a heating stage 7, and the chip 2 is pressed against the metal frame 1 to perform die bonding. Next, the chip 2 and the lead of the metal frame 1 are wire-bonded by the wire bonder 9. At this time, the movement of the chips can be prevented by providing the suction device 11 on the heating stage 10 and sucking the chips 2.

Specifically, first, an adhesive was applied to the metal frame 1 having the shape shown in FIG. FIG. 2 is a plan view from the metal frame side in a state where the metal frame 1 and the silicon chip 2 are bonded, and a part of the semiconductor element is exposed on the bonding surface side with the metal frame. Frame 1 by stringing when adhesive is applied
The adhesion of the adhesive to the other parts was evaluated. Table 2 shows the case where there was no adhesion, and the case where there was adhesion was x. In the heating stage 6, the solvent is evaporated by heating at 200 ° C. for 20 seconds, further moved to a die bonder 8, heated to 280 ° C. in the heating stage 7, and the metal frame 1 is heated on the heating stage.
A chip 2 of 5 mm square was placed on the substrate, and a load of 130 g was applied for 10 seconds to bond the chip 2. After performing this step 20 times, the contamination of the heating stage 7 was evaluated as ○ when no adhesion of the resin to the heating stage was visually observed, and as × when the adhesion was observed. The peel adhesion between the frame 1 and the chip 2 at room temperature was evaluated using a tension gauge, and the results are shown in Table 2. 100g adhesion at room temperature
Below the chip / chip, the chip may peel off during the movement.

Further, the metal frame 1 to which the chip 2 was bonded was wire-bonded to a heating stage 10 at a temperature of 320 ° C. in a wire bonder 9 provided with a suction device 11. At this time, the bonding state of the wire was evaluated, and as the wire bondability, those having no displacement and peeling of the wire were shown as ○, and those having displacement and peeling of the wire were shown as x in Table 2. Subsequently, the assembled product was resin-sealed with a transfer mold device to manufacture a semiconductor device. As the sealing material, CE manufactured by Hitachi Chemical Co., Ltd.
L-9200 was used.

In order to evaluate the reflow crack resistance, the manufactured semiconductor device was absorbed at 85 ° C. and a humidity of 85%, and treated at 240 ° C. for 10 seconds in an infrared reflow furnace. The time during which the semiconductor device swelled to 10% or more or cracked was measured as the anti-reflow time. The results are shown in Table 2.

[0041]

[Table 1]

[0042]

[Table 2]

[0043]

The polyesteramideimide resin according to claim 1 is thermoplastic in nature, is suitable as an adhesive for semiconductor devices, has excellent heat resistance and solvent solubility, and can be used at relatively low temperatures. Processing is possible. The polyester amide imide resin according to the second aspect exhibits the effects of the resin according to the first aspect, and further exhibits excellent solvent solubility, processing characteristics, and the like. The polyesteramide imide resin precursor according to the third aspect is capable of producing the polyesteramide imide resin having the excellent heat resistance according to the first aspect. The polyester amide imide resin precursor according to the fourth aspect is capable of producing the polyester amide imide resin having the excellent heat resistance according to the second aspect. According to the production method of the fifth aspect, it is possible to efficiently produce a precursor of a polyesteramideimide resin having excellent heat resistance and the like. According to the production method of the sixth aspect, a polyesteramideimide resin having excellent heat resistance and the like can be efficiently produced.

[Brief description of the drawings]

FIG. 1 is a conceptual diagram of a part of a manufacturing apparatus showing an example of a semiconductor device manufacturing apparatus used in an embodiment of the present invention.

FIG. 2 is a plan view showing a tab shape of a metal frame used in an application example of the present invention and a bonding state of a semiconductor element, as viewed from the metal frame side.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 ... Metal frame 2 ... Chip 3 ... Conveying device 4 ... Dispenser 5 ... Adhesive 6 ... Heating stage 7 ... Heating stage 8 ... Die bonder 9 ... Wire bonder 10 ... Heating stage 11 ... Suction device

Claims (6)

[Claims] 1. A compound of the general formula (I) (Wherein, R ¹ represents a divalent organic group, and m represents an integer of 2 to 20), and a general formula (II): (Wherein, R ² represents a divalent organic group, and n represents an integer of 4 to 12). 2. The amount of the repeating unit represented by the general formula (I) is 40 to 90 mol% of the total amount of the repeating units of the polyesteramide imide resin, and the amount of the repeating unit represented by the general formula (II) is The polyester amide imide resin according to claim 1, which is 5 to 20 mol% of the total amount of the imide resin. 3. A compound of the general formula (III) (Wherein, R ¹ represents a divalent organic group, and m represents an integer of 2 to 20), and a general formula (II): (Wherein, R ² represents a divalent organic group, and n represents an integer of 4 to 12). A polyesteramide imide resin precursor having a repeating unit represented by the following formula: 4. The amount of the repeating unit represented by the general formula (III) is 40 to 90 mol% of the total amount of the repeating unit of the polyesteramideimide resin precursor, and the amount of the repeating unit represented by the general formula (II) is The polyester amide imide resin precursor according to claim 3, which is 5 to 20 mol% of the total amount of the repeating units of the polyester amide imide resin precursor. 5. A compound of the general formula (IV) (Where n represents an integer of 4 to 12) to produce a polyamide by reacting a dicarboxylic acid and a diamine represented by the formula:
This is then converted to a compound of the general formula (V) (Wherein, R ¹ represents a divalent organic group, and m represents an integer of 2 to 20), and is reacted with a tetracarboxylic dianhydride and a diamine. How to make the body. 6. A method for producing a polyesteramide imide resin, comprising cyclizing the polyesteramide imide resin precursor according to claim 3 with imide.