EP1196485A1 - Compositions de resine epoxy hautes performances au cyanate bismaleinimide pour circuits imprimes et agents d'encapsulation - Google Patents

Compositions de resine epoxy hautes performances au cyanate bismaleinimide pour circuits imprimes et agents d'encapsulation

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Publication number
EP1196485A1
EP1196485A1 EP00936140A EP00936140A EP1196485A1 EP 1196485 A1 EP1196485 A1 EP 1196485A1 EP 00936140 A EP00936140 A EP 00936140A EP 00936140 A EP00936140 A EP 00936140A EP 1196485 A1 EP1196485 A1 EP 1196485A1
Authority
EP
European Patent Office
Prior art keywords
composition
cyanate ester
resin
curing agent
resin composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00936140A
Other languages
German (de)
English (en)
Other versions
EP1196485A4 (fr
Inventor
Miguel Albert Capote
Edward Smiley Harrison
Yong-Joon Lee
Howard Arthur Lenos
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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Publication date
Application filed by Individual filed Critical Individual
Priority claimed from PCT/US2000/013943 external-priority patent/WO2000071614A1/fr
Publication of EP1196485A1 publication Critical patent/EP1196485A1/fr
Publication of EP1196485A4 publication Critical patent/EP1196485A4/fr
Withdrawn legal-status Critical Current

Links

Definitions

  • This invention relates generally to printed circuits or encapsulated electronics devices, such a silicon chips, coated with curable resin compositions comprising epoxy resins, cyanate esters, bismaleimides, and a co-curing agent.
  • Epoxy resins which represent some of the most widely used resins, are characterized by easy processability, good adhesion to various substrates, high chemical and corrosion resistance, and excellent mechanical properties.
  • epoxy resins have relatively poor performance at high temperatures, have high dielectric constants, and exhibit significant water absorption.
  • Epoxy resins are generally cured by amines and anhydrides. The cured materials typically contain relatively large proportions of hydrophilic groups such as hydroxyl groups which increase water absorption. Epoxy resins thus are sensitive to hydrolysis at high temperature and high humidity.
  • the chemical resistance of epoxy resin is not as good as that of cyanate esters and bismaleimides.
  • Cyanate ester resins have improved performance relative to conventionally cured epoxy resins.
  • Polyfunctional cyanate esters are normally needed to achieve high crosslinking densities and high glass transition temperatures (Tg).
  • Tg glass transition temperatures
  • polyfunctional cyanate esters are typically solid or semi-solid at ambient temperatures and thus the formulated resin systems have relatively high viscosities. These resin systems often require significant amounts of solvents.
  • thermosetting resin Another leading thermosetting resin is bismaleimide which is characterized by excellent physical property retention at high temperatures and high humidities and stable (non-fluctuating) electrical properties over a wide temperature range.
  • bismaleimide particularly suitable for advanced composites and electronics.
  • Bismaleimides are capable of good performance at temperatures of up to about 230 °C to 250 °C with good hot- wet performance.
  • bismaleimide homopolymers are brittle and as a result are susceptible to microcracking.
  • the chemical resistance of bismaleimides is poor in the presence of base compounds.
  • bismaleimide is combined with cyanate ester to create a resin class generally known as BT resins. These resins provide improved glass transition temperature performance and other improved properties as compared to epoxy resins. They are also less expensive than cyanate ester resins.
  • the mixture of cyanate esters and bismaleimides exhibits little co-polymerization, therefore, the combination has inferior properties compared to pure cyanate ester or bismaleimide resins.
  • thermosetting resins demonstrating both high temperature performance and improved physical toughness, especially for microvia and encapsulated electrical interconnect electronics applications, such as printed circuits, flip chips, BGAs and chip scale packages.
  • This invention relates to a resin system comprising a mixture of epoxy resins, bismaleimides, cyanate esters and low viscosity co-curing agents that can be applied to a printed circuit, a silicon chip or wafer, or other electronic component, encapsulating it with a dielectric. Openings can be created in the encapsulating resin by conventional methods such as laser drilling, photoimaging, plasma, or other techniques known in the art. These openings can be metallized to form highly reliable electrical interconnections.
  • the inventive resin system demonstrates the excellent processability, adhesion, chemical and corrosion resistances, and mechanical qualities normally associated with epoxy resins; the system also exhibits superior physical and chemical properties as well as the stable electrical properties associated with bismaleimides and cyanate esters. All of these are highly desirable characteristics for encapsulants, microvia and interconnection applications.
  • the invention is directed to a curable composition that includes: (a) a cyanate ester;
  • a co-curing agent having the structure R ⁇ Ar-R 2 wherein Ar is at least one unsaturated aromatic carbox lic moiety, R 1 is at least one unsaturated aliphatic moiety and R 2 is at least one epoxide moiety with the proviso that when two or more unsaturated aromatic carboxylic moieties are present, at least one of the unsaturated aromatic carboxylic moieties has an unsaturated aliphatic moiety and an epoxide moiety attached thereto;
  • Preferred curing agents are 2-allylphenyl glycidyl ether and 2,2'-bis (3- ally-4-glycidoxy phenyl) isopropylidene, hereinafter referred to as 2,2' - diallylbisphenol A diglycidyl ether.
  • the co-curing agent reacts with the cyanate ester, epoxy resin and bismaleimide.
  • the viscosity of the co-curing agent is low enough at room temperature so that no solvent is generally necessary.
  • the crosslinking density of the cured composition can be varied over a wide range by adjusting the relative proportions of each component in the resin mixture.
  • the invention is based in part on the integration of (i) a glycidyl group, which is reactive with cyanate ester, and (ii) an unsaturated aliphatic group such as an allyl group, which is reactive to bismaleimide, into a co-curing agent molecule.
  • this co-curing agent in the inventive resin system not only makes it possible to co-cure cyanate ester and bismaleimide, in addition, it reduces the viscosity of the resin system because of the low viscosity of the co- curing agent. Furthermore, the combination of epoxy resin with the cyanate ester by means of well-established curing reactions produces a cured composition with the before mentioned desirable properties. For example, the thermal stability, high temperature performance and hot-wet resistance of the cured inventive resin system are superior to those of conventional amine and anhydride cured epoxy resins. In addition, the uncured resin exhibits excellent processability while the cured resin system demonstrates toughness and chemical resistance that are superior to those from bismaleimide or cyanate ester homopolymers.
  • Figure 1 are tan delta dynamic mechanical analyzer (DMA) scans from two resin mixtures showing the glass transition temperatures of two test resin mixes, one with and one without the co-curing agent APGE;
  • Figure 2 is the thermogravimetric scans for a cyanate ester-bismaleimide- epoxy resin mixture with APGE;
  • Figure 3 are thermal decomposition weight loss scans for (i) resins having APGE (ii) resins having DADE, and (iii) FR-4 epoxy laminate;
  • Figure 4 is the DMA scan of an inventive resin composition
  • Figure 5 is the DMA scan of an inventive resin composition
  • Figure 6 is the thermal mechanical analyzer scan of same inventive resin composition of Figure 5;
  • Figure 7 are differential scanning calorimetry scans of bismaleimide-co- curing agent mixtures with and without a free-radical initiator;
  • Figures 8, 9, and 10 illustrate encapsulation of an electronic device with a resin composition;
  • Figures 11, 12, and 13 illustrate encapsulation of a printed circuit board with a resin composition.
  • the present invention is based in part on the development of a resin system comprising cyanate ester resins, bismaleimides, co-curing agents and epoxy resins.
  • the co-curing agent comprises two different reactive groups: (i) a moiety having an unsaturated aliphatic group capable of reacting with bismaleimides, e.g. , an allyl group, and (ii) a glycidyl ether, that is capable of reacting with cyanate esters.
  • the physical properties of the pre and post cured inventive resin system can be varied by employing different proportions of cyanate esters, epoxy resins, bismaleimides, and co-curing agents.
  • Advantageous characteristics of the inventive resin system include, for example:
  • the hot- wet performance of the cured composition is much better than that of conventionally cured epoxy resins.
  • the co-curing agent has the structure R 1 -Ar-R 2 where Ar comprises is at least one aryl moiety, R 1 is at least one unsaturated aliphatic moiety and R 2 is at least one glycidyl ether moiety.
  • Ar preferably has one aryl moiety but it is understood that it can comprise multiple aromatic moieties linked linearly (e.g. a novolac), or by branching (e.g. triphenyl, tetraphenyl).
  • each aryl moiety has at least one of (i) an unsaturated aliphatic moiety and (ii) a glycidyl moiety attached thereto, with the proviso that the co-curing has at least one of each moiety.
  • the number of aromatic moieties in Ar is typically less about than
  • aryl refers to an unsaturated aromatic carbocyclic group of 6 to 14 carbon atoms having a single ring (e.g., phenyl) or multiple condensed rings (e.g. , naphthyl or anthryl).
  • Preferred aryls include phenyl, naphthyl and the like.
  • Preferred co-curing agents have structure I or II:
  • each of R 1 and R 2 is preferably H, CH 3 or CF 3 .
  • Both structures can be further substituted with, for example, lower alkyls having preferably 1-6 carbons more, preferably 1-3 carbons and halides CI, Br or F.
  • Particularly preferred co- curing agents are 2-allylphenyl glycidyl ether (APGE), and 2,2' -diallylbisphenol A diglycidyl ether (DADE) which have the following structures III and IN, respectively:
  • APGE and DADE can be synthesized in accordance with the following well-established reaction mechanism:
  • Suitable cyanate esters are polyfunctional molecules or oligomers having at least two -OCN groups. Cyanate esters are self reactive and also cure in the presence of epoxy resin or bismaleimide. Suitable polyfunctional cyanate esters are described, for example, in U.S. Patents 4,831,086, 5,464,726, 4,195,132, 3,681,292, 4,740,584, 4,745,215, 4,776,629 and 4,546,131, which are incorporated herein. Preferred polyfunctional cyanate esters include the following:
  • x is any suitable divalent moiety, such as -O-, a lower alkylene -(CH ⁇ ) m - where m is 1-6, preferably 1-3, and most preferably 1, -CH 3 CH 2 -, -CH 3 CH 3 CH 2 - ,or other functional divalent group.
  • a preferred polyfunctional cyanate ester used for its superior dielectric properties is:
  • n is an integer from 0 to 200 and preferably from 0 to 1.
  • n has an average value of about 0.4.
  • the polyfunctional cyanate serves to increase the density of cured resin composition.
  • the polyfunctional cyanates react with the epoxy resin and the epoxide group in the co-curing agent thereby forming crosslinked polymeric networks.
  • Polyfunctional cyanate esters are typically solid at ambient temperatures ( 25 °C) but dissolve readily in the co-curing agent and the epoxy resin, although some warming may be needed to bring about solution.
  • Suitable epoxy resins include any of a variety of polyfunctional epoxy resins that are known or commercially available. Suitable epoxy resins are described, for example, in U.S. Patent 5,464,726, which is incorporated herein. Preferred commercially available epoxy resins include, for example, bisphenol A epoxy resins, e.g. Shell EPON 800 series, bisphenol F, epoxy novolac, epoxy cresol novolac, N,N-diglycydyl-4-glycidoxy aniline, and 4,4'-methylenebis(N,N- diglycidylaniline).
  • bisphenol A epoxy resins e.g. Shell EPON 800 series
  • bisphenol F epoxy novolac
  • epoxy cresol novolac epoxy cresol novolac
  • N,N-diglycydyl-4-glycidoxy aniline and 4,4'-methylenebis(N,N- diglycidylaniline).
  • exemplary commercially available epoxy resins are available as Dow Tactix 742, Shell RSL-1107, EPON 825, EPON 828, EPON 1031 , SU-3, SU-8, and Ciba-Geigy Araldite LT8011 , LT8052, LT8047,
  • R is any suitable divalent functional moiety such as, e.g., a lower alkylene -(CHi),..-, where m is 1-6, preferably 1-3, and most preferably 1.
  • a preferred divalent functional moiety is:
  • Suitable bismaleimides are further described, for example, in U.S. Patents 5,464,726 and 4,978,727, which are incorporated herein.
  • a preferred bismaleimide is MDA Bismaleimide Resin 5292A from Ciba Geigy.
  • the newly formed free radical continues the chain reation.
  • the free radical initiator agent when employed, comprises about 0.1 % to 3 % , preferably 0.1 % to 2% and more preferably 0.5% to 1.5% by weight of the curable composition.
  • Ar groups are aryl groups.
  • Cyanate esters and epoxides co-polymerize through a complex series of rearrangement and substitution reactions, forming heterocyclic 5- or 6-membered rings.
  • Specific examples include oxazoline rings and oxazolidinone rings:
  • the photoinitiator induces a chain reaction or chain growth polymerization of unsaturated carbon-carbon bonds. This type of curing is effective for achieving a first stage crosslinking for photoimaging.
  • the mask can be made of any suitable UN blocking/absorbing material with openings through which UN radiation can be transmitted.
  • the non-exposed portions of the resin composition will form the microvias which typically have a diameter of about 20 ⁇ m to 200 ⁇ m. Any unexposed resin composition can then be dissolved away, leaving the image of the mask. Then the image can be completely hardened with heat.
  • the polymer can be applied in thin coats or layers that can be instantly UN-cured to a gel-set by the UN light initiated reaction.
  • the unexposed resin composition can then be washed away with a suitable solvent. Finally heat is applied to effect a deep and complete cure of the polymer resin.
  • cyanate ester and bismaleimide are each capable of self- polymerization.
  • concentrations of cyanate ester and bismaleimide can each vary from 1 to 99% of the molar concentration of the resin composition and still achieve complete polymerization.
  • the epoxy resin which does not self-polymerize needs the cyanate ester for the reaction to occur.
  • it is necessary to account for the epoxide in the co-curing agent as this reactive group also will consume cyanate esters during polymerization.
  • the components are mixed and heated in order to melt the bismaleimide and the polyfunctional cyanate ester which are solids.
  • the mixture is heated to a temperature range of about 70°C to 115°C until the mixture is a liquid.
  • a solvent such as methyl ethyl ketone or acetone can be added to the formulation to facilitate processability.
  • the system is initially cured at a lower temperature of about 120°C to 140°C for about 2 hours and is followed by post curing treatment (at 210° C to 230 °C) for another hour.
  • the cured resins have high glass transition temperatures ranging from 200°C to 250°C, depending on the component ratios; and the cured resins also exhibit thermal stability against decomposition to a temperature of at least between 350°C and 400°C.
  • the effectively tailored properties from epoxy and bismaleimide include the good adhesion properties, chemical resistance, low water absorption and high heat distortion temperature.
  • a catalyst for trimerization of the cyanate ester is required.
  • Acetylacetonates of various transition metals e.g., Cu, Co, Zn, can be employed at very low concentrations, e.g., a few hundred parts per million.
  • APGE was synthesized from 2-allyl phenol (AP) and epichlorohydrin (EPH) in the presence of aqueous sodium hydroxide at 115° C under nitrogen.
  • the reaction was optimized by using 10 times excess (molar ratio) of EPH and minimizing water in the reaction.
  • water was produced by the reaction between 2-AP and EPH. Since water and EPH form an azeotrope, water was removed from the reaction by azeotropic distillation, which also drives the reaction forward. Collected EPH was returned as needed to the mixture to prevent undesirable side reactions. After 4 hours, the resultant salts were separated from the product.
  • the non-optimized curing cycle for the two mixtures was: 2 hour at 125°C, 2 hours at 150°C, 1 hour at 175°C, 2 hours at 200°C.
  • DMA scans of tan delta for the APGE mixture are shown in Figure 2, indicating this mixture had a glass transition at 220 °C.
  • the DMA scans of the DADE mixture were very similar.
  • Figure 3 shows the thermogravimetric scans for the two resins, compared with epoxy FR-4 glass laminate. As is apparent, the glass transition of the FR-4 occurs at less than 150°C.
  • the resins clearly deliver superior thermal properties compared to conventional epoxy resin.
  • Example 5 (cured resin composition 3) To demonstrate thermal characteristics of high epoxy-content resin compositions, a resin mixture was made with the following components:
  • the curing cycle for the mixture was: 2 hours at 125°C, 2 hours at 150°C, 1 hour at 175°C and 2 hrs at 200°C.
  • dynamic mechanical analyzer scans of the cured composition indicate that the glass transition temperature is 242°C.
  • Example 6 (cured resin composition 4)
  • the paste produced in this example was screen printed onto a silicon wafer with a 100 mesh screen and cured per the above cure cycle.
  • the resultant encapsulant was observed to encapsulate the wafer uniformly and without voids or bubbles.
  • Example 7 (cured resin composition 5)
  • FIG. 6 illustrates the effect of the free radical.
  • the top DSC scan is for the mixture without the free radical initiator while the bottom scan is for the mixture with the initiator. Comparing the two scans, the second exotherm that peaks at about 370 °C in the top scan is observed to be unaffected by the free radical by appearing in both scans. However, the two exotherms that peak at about 250 °C in the upper scan have disappeared and have been replaced with a new exotherm at 102° C in the bottom scan.
  • Example 8 (cured resin composition 6)
  • the photoinitiator absorbs UN radiation followed by a subsequent reaction to give a free-radical initiator.
  • a thin layer of the photosensitive resin composition from a chloroform solution (i.e. , 2 ml/2 g concentration) was applied to an epoxy printed circuit boards. The thickness of the layer was not carefully controlled, but was about 0.001 in thick.
  • the "image” was developed by using either an acetone/water mixture (5 volume parts acetone to 1 volume part water) or a saturated aqueous solution of sodium carbonate. The edge of the exposed to unexposed region was readily discernable in the resin.
  • the developed resin was dried and post cured at 125 °C for 2 hours followed by 175 °C for 2 hours. The curing was monitored by Fourier Transform
  • FTIR Infrared
  • Figure 8 shows a flip chip or ball grid array device 1 which has electrical interconnection pads 2 on its surface.
  • the pads are encapsulated with a layer of the inventive resin 3.
  • Microvias 4 are created in the encapsulating resin layer 3 to expose the electrical interconnection pads 2 as shown in Figure 9 and Figure 10 shows that the microvias have been filled with electrically conductive interconnect material 5 e.g., solder.
  • Figure 11 shows a printed circuit board 6 having electrical interconnections pads 7 where the board 6 is encapsulated with a layer of the inventive resin composition 8.
  • Figure 12 the presence of microvia openings 9 in the encapsulating resin layer to expose the electrical interconnection pads 6.
  • Figure 13 shows the printed circuit board 6 wherein the microvias 9 and surface of the encapsulant 8 have been plated with electrically conductive interconnect material 10 e.g., copper.
  • electrically conductive interconnect material 10 e.g., copper.
  • the device has a patterned of the electrically conductive interconnect material that produces selected electrical interconnections between various microvias 11.

Landscapes

  • Epoxy Resins (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Cette invention concerne une composition utile comme agent d'encapsulation pour composants électroniques et comme couches diélectriques avec voies d'interconnexion microscopiques pour circuits imprimés. Cette composition réunit les avantages de chaque composant et compense la faiblesse d'autres composants grâce au mélange d'un cyanate ester, d'un bismaléimide, d'un agent co-durcisseur avec des fractions aliphatiques et glycidyliques insaturées, une résine époxy et, en option, un initiateur de radicaux libres.
EP00936140A 1999-05-21 2000-05-22 Compositions de resine epoxy hautes performances au cyanate bismaleinimide pour circuits imprimes et agents d'encapsulation Withdrawn EP1196485A4 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US346001 1982-02-08
US13535699P 1999-05-21 1999-05-21
US135356P 1999-05-21
US34600199A 1999-06-30 1999-06-30
PCT/US2000/013943 WO2000071614A1 (fr) 1999-05-21 2000-05-22 Compositions de resine epoxy hautes performances au cyanate bismaleinimide pour circuits imprimes et agents d'encapsulation

Publications (2)

Publication Number Publication Date
EP1196485A1 true EP1196485A1 (fr) 2002-04-17
EP1196485A4 EP1196485A4 (fr) 2002-10-30

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EP00936140A Withdrawn EP1196485A4 (fr) 1999-05-21 2000-05-22 Compositions de resine epoxy hautes performances au cyanate bismaleinimide pour circuits imprimes et agents d'encapsulation

Country Status (3)

Country Link
EP (1) EP1196485A4 (fr)
JP (1) JP2003500509A (fr)
AU (1) AU5150100A (fr)

Cited By (1)

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CN117690902A (zh) * 2024-02-03 2024-03-12 江门市和美精艺电子有限公司 一种含改性胶膜的封装基板

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SG172201A1 (en) * 2008-12-16 2011-07-28 Dow Global Technologies Llc Homogeneous bismaleimide - triazine - epoxy compositions useful for the manufacture of electrical laminates
JP6761572B2 (ja) * 2015-11-11 2020-09-30 三菱瓦斯化学株式会社 樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板
JP6618036B2 (ja) * 2015-11-25 2019-12-11 三菱瓦斯化学株式会社 樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117690902A (zh) * 2024-02-03 2024-03-12 江门市和美精艺电子有限公司 一种含改性胶膜的封装基板
CN117690902B (zh) * 2024-02-03 2024-04-12 江门市和美精艺电子有限公司 一种含改性胶膜的封装基板

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JP2003500509A (ja) 2003-01-07
AU5150100A (en) 2000-12-12
EP1196485A4 (fr) 2002-10-30

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