CN104559882B - A kind of liquid crystal type epoxy underfill and preparation method thereof - Google Patents
A kind of liquid crystal type epoxy underfill and preparation method thereof Download PDFInfo
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- CN104559882B CN104559882B CN201410317522.4A CN201410317522A CN104559882B CN 104559882 B CN104559882 B CN 104559882B CN 201410317522 A CN201410317522 A CN 201410317522A CN 104559882 B CN104559882 B CN 104559882B
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Abstract
The invention discloses a kind of liquid crystal type epoxy underfill and preparation method thereof, the filling glue is made up of following component：Epoxy resin composition, diluent, coupling agent, firming agent, curing accelerator, toughener, stabilizer and filler；There is the epoxy bottom filler for obtaining relatively low viscosity and quick fluid ability, low-temperature fast-curing ability, higher vitrification point and suitable heat decomposition temperature, adhesive strength and Tg to be greatly reduced rapidly after weathering, therefore can meet modern microelectronic encapsulation technology to filling the characteristic requirements of flowing fillibility, reliability and the reworkable property of glue etc..
Description
【Technical field】
The present invention relates to integrated antenna package field, and in particular to a kind of liquid crystal type epoxy underfill and its preparation side
Method.
【Background technology】
21 century, due to wireless telecommunications, portable computer, broadband internet network product and auto navigation electronic product
Demand, electronic device integrated level more and more higher, chip area constantly expand, and integrated circuit pinnumber is on the increase, at the same time
The further miniaturization of chip package size and miniaturization are required, integrated circuit more develops to light, thin, little direction.This development is answered to become
Gesture occurs in that many new encapsulation technologies and packing forms.Flip-chip (flip chip) interconnection technique is wherein topmost
One of encapsulation technology, flip chip technology (fct) particular content are that chip faces down to interconnect with substrate, make salient point become chip electrode
With the solder joint of substrate wiring layer, firmly welded, it provide higher packaging density, shorter interconnection distance, more preferably
Electrical property and Geng Gao reliability, and meet the trend of current microelectronics Packaging high density and miniaturization, therefore in multi-chip
It is widely applied in component and three-dimension packaging.Epoxy underfill (underfill) is a kind of suitable for flip-chip
The material of circuit, it is that liquid epoxies is filled in the slit between IC chip and organic substrate, and connection is welded
Dot encapsulation is protected.
After filled thermoset epoxy resin between chip and substrate, due to the cementation of resin, stress will be by again
Distribution so that the thermal coefficient of expansion between chip, substrate and pad mismatches degree and is preferably minimized, package reliability is improved
10-100 times.As current technology cannot ensure that supplied chip is necessarily intact so that some defective chips are falling
After dress, just tested discovery, is at this moment accomplished by being done over again.But the thermoset epoxy underfill material (ratio for generally using now
Such as ERL-4221) with extraordinary heat stability, and it is insoluble do not melt, this causes carrying out to ensure which when chip is replaced
Its components and parts is not damaged by, and causes whole multi-chip module failure, and manufacturer has to abandon monoblock circuit board.At present, more
Put in the middle of the new exploitation for repairing underfill come more research worker, common way is, by with
Some weak chemical bonds are introduced in the epoxy resin for making underfill so as to can still reheat or additionization after solidification
Decompose after learning reagent, having enable components and parts electric does over again and recycle.Repair process includes following six step：By heating or changing
Learning processing method reduces rapidly the adhesion strength of underfill；Bad chip is removed with chip pickup apparatus；Set with high speed outwash
It is standby to remove resin residue thing；Substrate is detected；The chip for more renewing；Re-start underfill.
For further reduces cost, the reliability for encapsulating is improved, to grinding for the underfill for flip-chip
Study carefully, be increasingly becoming a hot issue in microelectronic packaging technology field, related patent research is quite a few, such as：United States Patent (USP)
US11275080 discloses a kind of hot melt Underfill adhesive composition and its painting method, can underfill be carried out appointing
The staged process of B- of choosing, any excessive underfill can be removed from wafer bump block and chip is cut into individually
Tube core；Chinese patent CN101880514A is disclosed and a kind of is reprocessed the good one-component underfill of performance and its preparation side
Method；Chinese patent CN101880515A discloses a kind of high reliability, low-viscosity underfill, with biphenol type epoxy tree
Fat, electrodeless packing material and silane coupler for must material, with good mobility and heat-resisting cyclicity and highly reliable
Property；Chinese patent CN102504743A discloses one kind can single-component underfill capable of being stored at room temperature and preparation method thereof；In
State's patent CN102492263A discloses one kind can epoxy under-fill adhesive capable of quickly curing at low temperature and preparation method thereof；It is Chinese special
Sharp CN102559115A discloses a kind of chip-level bottom filling adhesive and preparation method thereof, with cure shrinkage is low, reliability
High the features such as, while meeting the requirement of low-activity, it is adaptable to the one-level high-density packages of Memorability chip；Chinese patent
A kind of Underfill adhesive composition is disclosed in CN103361016A, its viscosity is low, fast without the need for preheating, curing rate when using；
A kind of Rapid permeation bottom underfill and preparation method thereof is disclosed in Chinese patent CN102732199A, the filling glue is high viscous
Rapid osmotic is remained in the case of degree, noresidue at complete and applying glue is permeated；One kind is disclosed in Chinese patent CN103436211A
Good underfill of compatibility and preparation method thereof, the glue is excellent with scaling powder compatibility, reduces in flowing solidification process
The defect of middle formation；…….
It can be seen that, in the manufacture of underfill, the selection of material and proportioning or even process conditions be all it is very important,
It is to need constantly to grind excellent performance, with low cost underfill product to be made by optimal proportioning such as how optimal material
The big focus studied carefully.
【The content of the invention】
In order to overcome the deficiencies in the prior art, the invention provides a kind of liquid crystal type epoxy underfill and its preparation side
Method, to obtain the liquid crystal type epoxy bottom for having large-area flowing fillibility, high reliability and reworkable property in close gap
Fill glue in portion.
A kind of liquid crystal type epoxy underfill, is made up of following component：Epoxy resin composition, diluent, coupling agent,
Firming agent, curing accelerator, toughener, stabilizer and filler；
The epoxy resin composition is by epoxy resin by using liquid crystal, low viscosity epoxy resin and can repair epoxy resin three
Plant different types of epoxy resin to mix, wherein, the viscosity of the low viscosity epoxy resin is 200-1000mPa.s；
The diluent is epoxy type reactive diluent, including：Butyl glycidyl ether, phenyl glycidyl ether, allyl
Base glycidyl ether, methyl propenoic acid glycidyl ether or Ethylene glycol diglycidyl ether；
The coupling agent is silane coupling agent, including：Propyl methacrylate trimethoxy silane, three ethoxy of vinyl
Base silane, gamma-aminopropyl-triethoxy-silane, 3- glycydoxies trimethoxy silane or γ-mercapto propyl group front three
TMOS；
The firming agent is hexahydro -4- methyl nadic anhydrides or polymercaptan；
Acetylacetonate complex or 2-methylimidazole or 2- phenyl -4,5- dihydroxy first of the curing accelerator for Fe (III)
Base imidazoles or 2 phenyl 4 methyl 5 hydroxy methylimidazole；
The toughener be nitrile rubber class toughener, the nitrile rubber class toughener be end carboxyl nitrile (HTBN) -22,
Random carboxyl nitrile (HTBN) -1002 or nitrile (HTBN) -40；
The stabilizer is N- Phenyl beta naphthylamine or DBPC 2,6 ditertiary butyl p cresol；
Described filler is particle diameter in 0.5-1.5 μm of ball-shaped silicon micro powder；
The epoxy resin by using liquid crystal is phenylethylene epoxy resin by using liquid crystal or methylene amine epoxy resin by using liquid crystal, and structure is such as
Under：
Wherein：
The low viscosity epoxy resin is bisphenol f type epoxy resin or epoxidized phenol resin；
It is described repair epoxy resin for double (the 2,3- 7-oxa-bicyclo[4.1.0 epoxides) propane of 1,2- or 2- methyl -2,3- it is double (2,
3- 7-oxa-bicyclo[4.1.0 epoxides) butane or double【2- (2,3- 7-oxa-bicyclo[4.1.0 bases)】Phenylene dimethyl ether between isopropyl.
Preferably, the diluent is Ethylene glycol diglycidyl ether.
Preferably, the coupling agent is KH-550.
Preferably, acetylacetonate complex of the curing accelerator for Fe (III).
Preferably, the toughener is end carboxyl nitrile (HTBN) -22.
The usage ratio parts by weight of each component are：
Wherein, epoxy resin by using liquid crystal, low viscosity epoxy resin and can repair epoxy resin total mass fraction be 90-
110 parts.
Present invention also offers a kind of preparation method of described liquid crystal type epoxy underfill, comprises the steps：
S1：A certain amount of ball-shaped silicon micro powder is dried, the ball-shaped silicon micro powder after drying is added to into ethanol and is matched somebody with somebody
In the middle of the coupling agent solution put, the coupling agent solution is stirred with Glass rod, until solvent ethanol volatilizees, then to being coupled
Ball-shaped silicon micro powder dried；Meanwhile, the accelerator and the part epoxy resin by using liquid crystal are mixed into into paste, and it is right
The paste is ground；
S2：By the low viscosity epoxy resin, can repair in epoxy resin, toughener, diluent, filler, step S1 and dry
The ball-shaped silicon micro powder being coupled, epoxy resin by using liquid crystal described in remaining part after dry is mixed, and is carried out under 80-85 DEG C of environment
Evacuation, and make that the component of mixing is at a high speed dispersed to filler and resin is completely dissolved, then make the component temperature of mixing be down to 35
Below DEG C；
S3, adds the paste in the firming agent, stabilizer, step S1 to be stirred to the mixed composition in step S2
After uniform, and disperse at a high speed under vacuum conditions, temperature is less than 40 DEG C.
Preferably, the mixture in step S3 is solidified as follows：First at 130 DEG C, precuring 0.5 is little
When, then solidify 4 hours at 150 DEG C to being fully cured.
Preferably, in step S1, it is 110 DEG C to the temperature of ball-shaped silicon micro powder drying, drying time is 2h；
The temperature of the ball-shaped silicon micro powder drying to being coupled is 110 DEG C, and drying time is 1h；
Preferably, in step S3, a length of 1 hour when disperseing at a high speed.
After using such scheme, it is demonstrated experimentally that the epoxy bottom filler for obtaining have relatively low viscosity and quick fluid ability,
Low-temperature fast-curing ability, higher vitrification point and suitable heat decomposition temperature, adhesive strength and Tg are rapid after weathering
It is greatly reduced, therefore modern microelectronic encapsulation technology can be met to filling the flowing fillibility of glue, reliability and reworkable
The characteristic requirements of property etc..
【Specific embodiment】
Preferred embodiment to inventing below is described in further detail.
Embodiment 1
Formula is as follows：(mass fraction)
Step is as follows：
S1：The ball-shaped silicon micro powder of 50g is weighed first, 110 DEG C of drying baker is put into, and dries 2h；Take out the spherical silicon after drying
Micropowder is added in the middle of ethanol is configured 5% solution of the KH550 of coupling agent containing 5g, uses Glass rod agitating solution, Zhi Daorong
Agent ethanol volatilizees；Then the ball-shaped silicon micro powder being coupled is dried into 1h at 110 DEG C；Meanwhile, by the acetylacetone,2,4-pentanedione of 3g Fe (III)
Complex accelerator is mixed into paste with 10g epoxy resin by using liquid crystal LCEP-1, and Jing three-roll grinders grind twice, standby；
S2：40g LCEP-1,25g YDF-8170C are added in planet power mixer, Jing tables in 25g RWEP-1, S1
The modified silicon powder (50g) in face, 28g end carboxyls nitrile (HTBN) -22,33g Ethylene glycol diglycidyl ethers, control material temperature is
80-85 DEG C, after evacuation is dispersed at a high speed filler and resin is completely dissolved, toward the logical cooling water of stirred tank chuck, make temperature of charge
It is reduced to less than 35 DEG C；
S3：Accelerator in the resin compound in S2 in addition 55g HMPA, 5g N- Phenyl beta naphthylamine and S1
Paste etc. opens vacuum system after stirring, disperse 1 hour at a high speed under vacuum conditions, whole process control material temperature
Less than 40 DEG C, finally with swager filtering and discharging subpackage.
Performance test：
Low-temperature fast-curing criterion：120 DEG C × 120s, curing degree reaches more than 90%；
It is fully cured condition：First 130 DEG C × 0.5h, afterwards 150 DEG C × 4h；
Do over again high temperature ageing condition：225℃×5min.
The mobile performance (viscosity, flowing velocity) of product and low-temperature fast-curing performance (curing degree) are before curing
Test under glue state；And hot property (initial heat decomposition temperature IDT, thermal coefficient of expansion CTE, glass transition temperature Tg, reliability
Property test (thermal shock with hot and humid)) and mechanical property (shear strength of the chip to wiring board), then be completely solid
Test in the state of change, which part can embody the index whether with reworkable property, such as：Tg and shear strength, in addition it is also necessary to
Cured article is carried out after high temperature ageing process, the corresponding numerical value of re-test is contrasted.
Embodiment 2
This example is the difference is that only with embodiment 1：The epoxy resin repaired RWEP-1 in embodiment 1 is replaced with
RWEP-2, other are constant.
Embodiment 3
This example is the difference is that only with embodiment 1：The epoxy resin repaired RWEP-1 in embodiment 1 is replaced with
RWEP-3, other are constant.
The test result of 3 embodiments of the above is as shown in table 1 below：
The test result of 13 embodiments of table
As can be seen from Table 1, epoxy underfill of the invention has preferable mobile performance (viscosity ＜
10000mPa.s/25 DEG C, flowing velocity ＜ 20s), it is ensured that its filling capacity between small gaps；Can low temperature it is quickly solid
(after 120 DEG C × 120s, curing degree is more than 90%), it is ensured that workability and production efficiency for change；Higher glass transition temperature
Tg (115 DEG C of Tg ＞) and initial heat decomposition temperature IDT (210-230 DEG C) are conducive to the reliability after device encapsulation, and due to IDT
Do over again near 220 DEG C of temperature in best safety, it is possible to carry out localization heating at this temperature to defective device and return
Repair；Relatively low thermal coefficient of expansion (CTE ＜ 43ppm/ DEG C) is conducive to eliminating the internal residual thermal stress of encapsulation to greatest extent；And
Before and after aging Tg and shear strength significant difference (Tg and shear strength after aging is significantly lower than aging front numerical value, it is aging after
Chip and substrate between the adhesive strength range of decrease more than 50%), then showing that product of the present invention has preferable reworkable property, work as device
When part needs to do over again, localization heating several minutes are only needed, it is possible to easily bad chip is taken off, is met current microelectronics and is fallen
Requirement of the cartridge chip to reworkable technique.
Comparative example 1
This example with the difference of embodiment 1 is：It is not added with epoxy resin by using liquid crystal component, low viscosity epoxy resin and Ke Xiu
The dosage of multiple epoxy resin component is all respectively increased to 50 parts, and 100 parts of the total dosage holding of hybrid resin is constant.
Test result：Heat decomposition temperature too low (195 DEG C), thermal coefficient of expansion CTE too high (71.6ppm/ DEG C), reliability are surveyed
Examination (hot and humid) does not pass through.Its thermostability, dimensional stability and reliability obviously can not meet use requirement.
As can be seen here, used as important component indispensable in the filler of bottom, it is orderly that it has merged liquid crystal to epoxy resin by using liquid crystal
With the advantage of network cross-linked, compared with ordinary epoxy resin, its thermostability, resistance to water and resistance to impact are all greatly improved, especially
It is that in the orientation direction, dimensional stability and dielectric properties are excellent.Thus can be used for the Electronic Packaging material high to performance requirement
Material and high-performance composite materials, are a kind of functional materials hveing great potential.
Comparative example 2
This example with the difference of embodiment 1 is：Low viscosity epoxy resin component is not added with, epoxy resin component can be repaired
Dosage improve to 50 parts, the total dosage of hybrid resin keep 100 parts it is constant.
Test result：Viscosity (18750mPa.s/25 DEG C) ＞ 10000mPa.s/25 DEG C, flowing velocity (56s) ＞ 15s, no
The characteristic requirements that underfill low temperature quickly flows can be met.
Comparative example 3
This example with the difference of embodiment 1 is：It is not added with repairing epoxy resin component, low viscosity epoxy resin component
Dosage improve to 50 parts, the total dosage of hybrid resin keep 100 parts it is constant.
Test result：Heat decomposition temperature too high (325 DEG C), does over again temperature range (210-230 DEG C) beyond best safety；Always
Before and after change, Tg and change of sheer strength are little：Tg：237 DEG C of (before aging)/229 DEG C (after aging), shear strengths：18.3MPa it is (old
Before change)/18.1MPa (after aging), it is clear that do not possess reworkable property.
Above content is with reference to specific preferred implementation further description made for the present invention, it is impossible to assert
The present invention be embodied as be confined to these explanations.For general technical staff of the technical field of the invention,
On the premise of without departing from present inventive concept, some simple deduction or replace can also be made, should all be considered as belonging to the present invention by
The scope of patent protection that the claims submitted to determine.
Claims (9)
1. a kind of liquid crystal type epoxy underfill, is characterized in that, is made up of following component：Epoxy resin composition, diluent,
Coupling agent, firming agent, curing accelerator, toughener, stabilizer and filler；
The epoxy resin composition is by epoxy resin by using liquid crystal, low viscosity epoxy resin and can repair three kinds of epoxy resin not
The epoxy resin of same type is mixed, wherein, the viscosity of the low viscosity epoxy resin is 200-1000mPa.s；
The diluent is epoxy type reactive diluent, including：Butyl glycidyl ether, phenyl glycidyl ether, pi-allyl contracting
Water glycerin ether, methyl propenoic acid glycidyl ether or Ethylene glycol diglycidyl ether；
The coupling agent is silane coupling agent, including：Propyl methacrylate trimethoxy silane, vinyl triethoxyl silicon
Alkane, gamma-aminopropyl-triethoxy-silane, 3- glycydoxies trimethoxy silane or γ-mercapto propyl trimethoxy
Silane；
The firming agent is hexahydro -4- methyl nadic anhydrides or polymercaptan；
Acetylacetonate complex or 2-methylimidazole or 2- phenyl -4,5- dihydroxymethyl miaow of the curing accelerator for Fe (III)
Azoles or 2 phenyl 4 methyl 5 hydroxy methylimidazole；
The toughener is nitrile rubber class toughener, and the nitrile rubber class toughener is end carboxyl nitrile (HTBN) -22, random
Carboxyl nitrile (HTBN) -1002 or nitrile (HTBN) -40；
The stabilizer is N- Phenyl beta naphthylamine or DBPC 2,6 ditertiary butyl p cresol；
Described filler is particle diameter in 0.5-1.5 μm of ball-shaped silicon micro powder；
The epoxy resin by using liquid crystal is phenylethylene epoxy resin by using liquid crystal or methylene amine epoxy resin by using liquid crystal, and structure is as follows：
Wherein：
The low viscosity epoxy resin is bisphenol f type epoxy resin or epoxidized phenol resin；
It is described to repair epoxy resin for double (the 2,3- 7-oxa-bicyclo[4.1.0 epoxides) propane of 1,2- or double (the 2,3- rings of 2- methyl -2,3-
Oxygen hexamethylene alkoxyl) butane or double【2- (2,3- 7-oxa-bicyclo[4.1.0 bases)】Phenylene dimethyl ether between isopropyl.
2. liquid crystal type epoxy underfill as described in claim 1, is characterized in that：
The diluent is Ethylene glycol diglycidyl ether.
3. liquid crystal type epoxy underfill as described in claim 1, is characterized in that：
The coupling agent is KH-550.
4. liquid crystal type epoxy underfill as described in claim 1, is characterized in that：The curing accelerator is Fe (III)
Acetylacetonate complex.
5. liquid crystal type epoxy underfill as described in claim 1, is characterized in that：The toughener is end carboxyl liquid
Butyronitrile -22.
6. liquid crystal type epoxy underfill as claimed in claim 1, is characterized in that, the usage ratio parts by weight of each component
For：
Wherein, epoxy resin by using liquid crystal, low viscosity epoxy resin and can repair epoxy resin total mass fraction be 90-110 parts.
7. a kind of preparation method of liquid crystal type epoxy underfill as claimed in claim 1, is characterized in that, including following step
Suddenly：
S1：A certain amount of ball-shaped silicon micro powder is dried, the ball-shaped silicon micro powder after drying is added to into ethanol and is configured
Coupling agent solution in the middle of, stir the coupling agent solution with Glass rod, until solvent ethanol volatilizees, the then ball to being coupled
Shape silicon powder is dried；Meanwhile, the accelerator and the part epoxy resin by using liquid crystal are mixed into into paste, and to described
Paste is ground；
S2：By the low viscosity epoxy resin, can repair in epoxy resin, toughener, diluent, filler, step S1 after drying
The ball-shaped silicon micro powder being coupled, epoxy resin by using liquid crystal described in remaining part mixed, carry out taking out true under 80-85 DEG C of environment
Sky, and make that the component of mixing is at a high speed dispersed to filler and resin is completely dissolved, then make the component temperature of mixing be down to 35 DEG C with
Under；
S3, adds the paste in the firming agent, stabilizer, step S1 to be stirred uniformly to the mixed composition in step S2
Afterwards, and under vacuum conditions disperse at a high speed, temperature is less than 40 DEG C.
8. the preparation method of liquid crystal type epoxy underfill as claimed in claim 7, is characterized in that：Will be mixed in step S3
Compound is solidified as follows：First precuring 0.5 hour at 130 DEG C, then solidify 4 hours at 150 DEG C to complete
Solidification.
9. the preparation method of liquid crystal type epoxy underfill as claimed in claim 7, is characterized in that：
In step S1, it is 110 DEG C to the temperature of ball-shaped silicon micro powder drying, drying time is 2h；To what is be coupled
The temperature of ball-shaped silicon micro powder drying is 110 DEG C, and drying time is 1h；
In step S3, a length of 1 hour when disperseing at a high speed.
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| CN111349414A (en) * | 2018-12-21 | 2020-06-30 | 上海得荣电子材料有限公司 | Low-stress insulating glue and preparation method thereof |
| CN113088230A (en) * | 2021-05-12 | 2021-07-09 | 东莞精旺电子有限公司 | Underfill adhesive and preparation process and application thereof |
| CN113388350B (en) * | 2021-06-30 | 2022-08-30 | 顺德职业技术学院 | Epoxy structural adhesive capable of being heated for repair and preparation method thereof |
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| CN103184023A (en) * | 2013-03-01 | 2013-07-03 | 广东丹邦科技有限公司 | Conductive silver adhesive for micropore filling and preparation method thereof |
| CN103184017A (en) * | 2013-03-01 | 2013-07-03 | 广东丹邦科技有限公司 | Additive for anisotropic conductive adhesives and preparation method thereof |
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| US20070293603A1 (en) * | 2006-06-19 | 2007-12-20 | Ashland Licensing And Intellectual Property Llc | Epoxy adhesive composition and use thereof |
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|---|---|---|---|---|
| CN103184023A (en) * | 2013-03-01 | 2013-07-03 | 广东丹邦科技有限公司 | Conductive silver adhesive for micropore filling and preparation method thereof |
| CN103184017A (en) * | 2013-03-01 | 2013-07-03 | 广东丹邦科技有限公司 | Additive for anisotropic conductive adhesives and preparation method thereof |
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