JP2000212400A - Epoxy resin composition for sealing optical semiconductor and optical semiconductor device - Google Patents
Epoxy resin composition for sealing optical semiconductor and optical semiconductor deviceInfo
- Publication number
- JP2000212400A JP2000212400A JP11017726A JP1772699A JP2000212400A JP 2000212400 A JP2000212400 A JP 2000212400A JP 11017726 A JP11017726 A JP 11017726A JP 1772699 A JP1772699 A JP 1772699A JP 2000212400 A JP2000212400 A JP 2000212400A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- optical semiconductor
- group
- resin composition
- semiconductor encapsulation
- 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.)
- Granted
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 63
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 63
- 239000004065 semiconductor Substances 0.000 title claims abstract description 45
- 230000003287 optical effect Effects 0.000 title claims abstract description 43
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 238000007789 sealing Methods 0.000 title abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 49
- -1 ethoxy compound Chemical class 0.000 claims abstract description 29
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000005538 encapsulation Methods 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000000465 moulding Methods 0.000 abstract description 17
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract description 9
- 230000003578 releasing effect Effects 0.000 abstract description 6
- 238000013329 compounding Methods 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000005011 phenolic resin Substances 0.000 abstract description 3
- 229920003986 novolac Polymers 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 5
- 239000006082 mold release agent Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 3
- 238000001721 transfer moulding Methods 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- XZKLXPPYISZJCV-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole Chemical compound C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 XZKLXPPYISZJCV-UHFFFAOYSA-N 0.000 description 1
- KHTJRKQAETUUQH-UHFFFAOYSA-N 2-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCC(CO)C(N)=O KHTJRKQAETUUQH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 102100033040 Carbonic anhydrase 12 Human genes 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 101000867855 Homo sapiens Carbonic anhydrase 12 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- SWSBIGKFUOXRNJ-CVBJKYQLSA-N ethene;(z)-octadec-9-enamide Chemical compound C=C.CCCCCCCC\C=C/CCCCCCCC(N)=O.CCCCCCCC\C=C/CCCCCCCC(N)=O SWSBIGKFUOXRNJ-CVBJKYQLSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- FEEPBTVZSYQUDP-UHFFFAOYSA-N heptatriacontanediamide Chemical compound NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(N)=O FEEPBTVZSYQUDP-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- DJWFNQUDPJTSAD-UHFFFAOYSA-N n-octadecyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCCCCCCCCCCCC DJWFNQUDPJTSAD-UHFFFAOYSA-N 0.000 description 1
- HNWJSFBLWQRXIR-UHFFFAOYSA-N octadecanamide;1,3-xylene Chemical compound CC1=CC=CC(C)=C1.CCCCCCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCCCCCC(N)=O HNWJSFBLWQRXIR-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ＬＥＤ、フォトト
ランジスター、フォトダイオード、ＣＣＤ、ＥＰＲＯＭ
などの光半導体（素子）を封止するために用いられるト
ランスファーモールド用エポキシ樹脂組成物、及びこの
組成物を用いて光半導体を封止して形成される光半導体
装置に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an LED, a phototransistor, a photodiode, a CCD, and an EPROM.
The present invention relates to an epoxy resin composition for transfer molding used to seal an optical semiconductor (element) such as an optical semiconductor device, and an optical semiconductor device formed by sealing an optical semiconductor using the composition.
【０００２】[0002]
【従来の技術】発光素子や受光素子などの光半導体の封
止材料としては、透明性、密着性、耐湿性、電気絶縁
性、耐熱性などの点で優れるエポキシ樹脂組成物が主流
となっている。特に、エポキシ樹脂組成物を用いたトラ
ンスファーモールドでの樹脂封止は、作業性並びに量産
性の面で優れているが、このトランスファーモールド用
のエポキシ樹脂組成物には一般に、金型からの離型性を
向上させるために内部離型剤が添加されている。ここ
で、光半導体の封止材料は透明性が重要視されるため
に、内部離型剤としてはエポキシ樹脂組成物に相溶する
必要があり、そのため従来の内部離型剤では離型効果の
少ないものしか用いることができず、またその添加量も
少量に制限されているのが現状であった。2. Description of the Related Art As an encapsulating material for optical semiconductors such as light emitting elements and light receiving elements, epoxy resin compositions which are excellent in transparency, adhesion, moisture resistance, electrical insulation, heat resistance and the like have become mainstream. I have. In particular, resin encapsulation in a transfer mold using an epoxy resin composition is excellent in terms of workability and mass productivity, but in general, the epoxy resin composition for transfer mold is released from a mold. An internal release agent is added to improve the properties. Here, since the transparency of the encapsulating material for the optical semiconductor is regarded as important, it is necessary to be compatible with the epoxy resin composition as the internal release agent. At present, only a small amount can be used, and the amount of addition is limited to a small amount.
【０００３】このため、従来では金型からの成形体の離
型性を確保するために、フッ素系やシリコーン系の化合
物を含む離型剤を外部離型剤として予め（封止成形の前
に）金型の表面にスプレー方式等で吹き付けるようにし
ている。For this reason, conventionally, in order to ensure the releasability of a molded article from a mold, a release agent containing a fluorine-based or silicone-based compound is used in advance as an external release agent (before sealing molding). ) The surface of the mold is sprayed by a spray method or the like.
【０００４】[0004]
【発明が解決しようとする課題】しかしながら上記のよ
うな外部離型剤を使用すると、成形サイクルの悪化によ
り生産効率（成形効率）を向上させることができなかっ
たり、成形体の表面に付着する外部離型剤成分の厚みの
ばらつきにより光半導体装置の特性にばらつきが生じた
りする恐れがあり、また外部離型剤のコストもかかり、
さらには外部離型剤に含まれている溶剤が環境に及ぼす
影響も懸念されるものであった。However, when the above-mentioned external release agent is used, the production efficiency (molding efficiency) cannot be improved due to the deterioration of the molding cycle, or the external adhering to the surface of the molded article cannot be achieved. Variations in the thickness of the release agent component may cause variations in the characteristics of the optical semiconductor device, and the cost of the external release agent also increases,
Further, there is a concern that the solvent contained in the external release agent may affect the environment.
【０００５】本発明は上記の点に鑑みてなされたもので
あり、生産効率を向上させることができ、しかも透明
性、密着性、耐湿信頼性、バリ離型性にも優れる光半導
体封止用エポキシ樹脂組成物を提供することを目的とす
るものである。また金型からの離型性に優れ、透明性、
密着性、耐湿信頼性にも優れる光半導体装置を提供する
ことを目的とするものである。SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and is intended for an optical semiconductor encapsulation capable of improving production efficiency and having excellent transparency, adhesion, moisture resistance reliability, and flash release properties. It is an object to provide an epoxy resin composition. Also excellent in mold release, transparency,
It is an object of the present invention to provide an optical semiconductor device having excellent adhesion and moisture resistance reliability.
【０００６】[0006]
【課題を解決するための手段】本発明の請求項１に係る
光半導体封止用エポキシ樹脂組成物は、（ａ）エポキシ
樹脂、（ｂ）硬化剤、（ｃ）離型剤、（ｄ）一般式
（１）（２）の硬化促進剤の少なくとも一方を含有して
成ることを特徴とするものである。The epoxy resin composition for encapsulating an optical semiconductor according to claim 1 of the present invention comprises (a) an epoxy resin, (b) a curing agent, (c) a release agent, and (d). It is characterized by containing at least one of the curing accelerators of the general formulas (1) and (2).
【０００７】[0007]
【化５】 Embedded image
【０００８】[0008]
【化６】 Embedded image
【０００９】但し、Ｒ１は水素、メチル基、イソプロピ
ル基、ｔ−ブチル基、ウンデシル基、ヘプタデシル基、
フェニル基、ベンジル基、ヒドロキシメチル基などから
選ばれる一つである。Ｒ２は水素、ベンジル基、メチル
基、エチル基、シアノメチル基、シアノエチル基などか
ら選ばれる一つである。Ｒ３は安息香酸、フタル酸、フ
マル酸、トリメリット酸、塩酸、イソシアヌル酸などか
ら選ばれる一つである。Ｒ４，Ｒ５，Ｒ６，Ｒ７は水
素、メチル基、ヒドロキシメチル基、ヒドロキシエチル
基などから選ばれる一つである。Wherein R1 is hydrogen, methyl, isopropyl, t-butyl, undecyl, heptadecyl,
It is one selected from a phenyl group, a benzyl group, a hydroxymethyl group and the like. R2 is one selected from hydrogen, a benzyl group, a methyl group, an ethyl group, a cyanomethyl group, a cyanoethyl group, and the like. R3 is one selected from benzoic acid, phthalic acid, fumaric acid, trimellitic acid, hydrochloric acid, isocyanuric acid and the like. R4, R5, R6, and R7 are one selected from hydrogen, a methyl group, a hydroxymethyl group, a hydroxyethyl group, and the like.
【００１０】また本発明の請求項２に係る光半導体封止
用エポキシ樹脂組成物は、請求項１の構成に加えて、
（ｄ）硬化促進剤の含有量が全量に対して０．０５〜３
重量％であることを特徴とするものである。The epoxy resin composition for encapsulating an optical semiconductor according to claim 2 of the present invention has the following features.
(D) The content of the curing accelerator is 0.05 to 3 with respect to the total amount.
% By weight.
【００１１】また本発明の請求項３に係る光半導体封止
用エポキシ樹脂組成物は、請求項１又は２の構成に加え
て、（ｃ）離型剤として、炭素数が１８以上のエトキシ
化合物を用いて成ることを特徴とするものである。The epoxy resin composition for encapsulating an optical semiconductor according to claim 3 of the present invention, in addition to the constitution of claim 1 or 2, further comprises (c) an ethoxy compound having 18 or more carbon atoms as a release agent. Is characterized by using the following.
【００１２】また本発明の請求項４に係る光半導体封止
用エポキシ樹脂組成物は、請求項１乃至３のいずれかの
構成に加えて、（ｃ）離型剤として、（ｅ）一般式
（３）で示される炭素数が１８以上の第一級アルコール
のエトキシ化合物を用いて成ることを特徴とする請求項
１乃至３のいずれかに記載の光半導体封止用エポキシ樹
脂組成物。The epoxy resin composition for encapsulating an optical semiconductor according to claim 4 of the present invention is characterized in that, in addition to the constitution of any one of claims 1 to 3, (c) as a mold release agent, The epoxy resin composition for optical semiconductor encapsulation according to any one of claims 1 to 3, wherein an ethoxy compound of a primary alcohol having 18 or more carbon atoms represented by (3) is used.
【００１３】[0013]
【化７】 Embedded image
【００１４】但し、Ａは１７〜１００の整数、Ｂは正の
整数である。Here, A is an integer of 17 to 100, and B is a positive integer.
【００１５】また本発明の請求項５に係る光半導体封止
用エポキシ樹脂組成物は、請求項１乃至４のいずれかの
構成に加えて、（ｅ）一般式（３）で示される炭素数が
１８以上の第一級アルコールのエトキシ化合物の含有量
が全量に対して０．０５〜５重量％であることを特徴と
するものである。Further, the epoxy resin composition for encapsulating an optical semiconductor according to claim 5 of the present invention further comprises (e) a carbon number represented by the general formula (3) in addition to any one of claims 1 to 4. Is 18 or more, and the content of the ethoxy compound of the primary alcohol is 0.05 to 5% by weight based on the total amount.
【００１６】また本発明の請求項６に係る光半導体封止
用エポキシ樹脂組成物は、請求項１乃至５のいずれかの
構成に加えて、（ｃ）離型剤として、（ｆ）一般式
（４）で示される炭素数が１８以上の第一級カルボン酸
のエトキシ化合物を用いて成ることを特徴とするもので
ある。The epoxy resin composition for encapsulating an optical semiconductor according to claim 6 of the present invention is characterized in that, in addition to the constitution of any one of claims 1 to 5, (c) as a mold release agent, It is characterized by comprising using an ethoxy compound of a primary carboxylic acid having 18 or more carbon atoms represented by (4).
【００１７】[0017]
【化８】 Embedded image
【００１８】但し、Ｃは１７〜１００の整数、Ｄは正の
整数である。Here, C is an integer of 17 to 100, and D is a positive integer.
【００１９】また本発明の請求項７に係る光半導体封止
用エポキシ樹脂組成物は、請求項１乃至６のいずれかの
構成に加えて、（ｆ）一般式（４）で示される炭素数が
１８以上の第一級カルボン酸のエトキシ化合物の含有量
が全量に対して０．０５〜５重量％であることを特徴と
するものである。The epoxy resin composition for encapsulating an optical semiconductor according to claim 7 of the present invention may further comprise (f) a carbon number represented by the following general formula (4): Wherein the content of the ethoxy compound of a primary carboxylic acid having a carboxylic acid content of 18 or more is 0.05 to 5% by weight based on the total amount.
【００２０】本発明の請求項８に係る光半導体装置は、
請求項１乃至７のいずれかに記載の光半導体封止用エポ
キシ樹脂組成物で封止して成ることを特徴とするもので
ある。An optical semiconductor device according to claim 8 of the present invention is:
It is characterized by being sealed with the epoxy resin composition for optical semiconductor sealing according to any one of claims 1 to 7.
【００２１】[0021]
【発明の実施の形態】以下、本発明の実施の形態を説明
する。Embodiments of the present invention will be described below.
【００２２】（ａ）成分のエポキシ樹脂としては、一分
子中に二個以上のエポキシ基を有するものであれば、特
に制限はないが、比較的着色の少ないものを使用するの
が好ましい。具体的には、ビスフェノールＡ型エポキシ
樹脂、ビスフェノールＦ型エポキシ樹脂、ビスフェノー
ルＳ型エポキシ樹脂、オルトクレゾールノボラック型エ
ポキシ樹脂、脂環式エポキシ樹脂、トリグリシジルイソ
シアヌレート、脂肪族系エポキシ樹脂などを挙げること
ができる。これらは単独で用いたりあるいは併用しても
差し支えない。The epoxy resin as the component (a) is not particularly limited as long as it has two or more epoxy groups in one molecule, but it is preferable to use a resin having relatively little coloring. Specifically, mention may be made of bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, orthocresol novolak type epoxy resin, alicyclic epoxy resin, triglycidyl isocyanurate, aliphatic epoxy resin and the like. Can be. These may be used alone or in combination.
【００２３】（ｂ）成分の硬化剤としては（ａ）成分の
エポキシ樹脂と反応するものであれば、特に制限はない
が、比較的着色の少ないものを使用するのが好ましい。
具体的には、無水ヘキサヒドロフタル酸などの酸無水
物、フェノール、クレゾール、キシレノール、レゾール
シン等とホルムアルデヒドとを縮合反応して得られるノ
ボラック型フェノール樹脂、液状ポリメルカプタンやポ
リサルファイド樹脂などのポリメルカプタン系硬化剤な
どを挙げることができる。この他にもアミン系の硬化剤
なども用いることができるが、硬化時の変色が大きいの
で、使用する際には添加量を少なくするなどの注意を要
する。これらは単独で用いたりあるいは併用しても差し
支えない。The curing agent of the component (b) is not particularly limited as long as it reacts with the epoxy resin of the component (a), but it is preferable to use a relatively less colored one.
Specifically, acid anhydrides such as hexahydrophthalic anhydride, phenol, cresol, xylenol, novolak-type phenolic resin obtained by condensation reaction with formaldehyde and resolecin, and polymercaptan-based such as liquid polymercaptan and polysulfide resin Curing agents and the like can be mentioned. In addition, an amine-based curing agent can be used, but since the discoloration at the time of curing is large, attention must be paid to reducing the amount of addition when used. These may be used alone or in combination.
【００２４】（ｃ）成分の離型剤としては、（ｅ）成分
である一般式（３）で示される炭素数が１８以上の第一
級アルコールのエトキシ化合物（Ａは１７〜１００の整
数、Ｂは１〜１００の整数）と（ｆ）成分である一般式
（４）で示される炭素数が１８以上の第一級カルボン酸
のエトキシ化合物（Ｃは１７〜１００の整数、Ｄは１〜
１００の整数）の少なくとも一方を用いる。（ｅ）成分
と（ｆ）成分の配合量は本発明のエポキシ樹脂組成物の
全量に対してそれぞれ０．０５〜５重量％に設定するの
が好ましい。（ｅ）成分と（ｆ）成分の配合量が０．０
５重量％未満であれば、充分な離型効果を得ることがで
きなくなる恐れがあり、また（ｅ）成分と（ｆ）成分の
配合量が５重量％を超えると、成形品が白濁したり、半
導体（素子）やリードフレームなどのインナーとの密着
性が低下したり、耐湿信頼性が低下したり、成形品の強
度が低くなることにより耐クラック性が低下したりする
恐れがある。より好ましくは、（ｅ）成分と（ｆ）成分
の合計量がエポキシ樹脂組成物の全量に対してそれぞれ
０．０５〜５重量％となるように配合する。As the mold release agent of the component (c), an ethoxy compound of a primary alcohol having 18 or more carbon atoms represented by the general formula (3) as the component (e) (A is an integer of 17 to 100, B is an integer of 1 to 100) and an ethoxy compound of a primary carboxylic acid having 18 or more carbon atoms represented by the general formula (4) (C is an integer of 17 to 100;
(An integer of 100). It is preferable that the compounding amounts of the component (e) and the component (f) are each set to 0.05 to 5% by weight based on the total amount of the epoxy resin composition of the present invention. When the compounding amount of the component (e) and the component (f) is 0.0
If the amount is less than 5% by weight, a sufficient release effect may not be obtained. If the amount of the component (e) and the component (f) exceeds 5% by weight, the molded article may become cloudy. In addition, there is a possibility that the adhesiveness to an inner such as a semiconductor (element) or a lead frame is reduced, the moisture resistance reliability is reduced, and the crack resistance is reduced due to a decrease in the strength of the molded product. More preferably, they are blended so that the total amount of the components (e) and (f) is 0.05 to 5% by weight based on the total amount of the epoxy resin composition.
【００２５】これら（ｅ）成分と（ｆ）成分は離型剤と
して作用すると同時に、本発明で用いることができる他
の離型剤をエポキシ樹脂組成物中に均一に分散させる作
用も有するものである。ここでいう他の離型剤とは、特
に制限されるものではないが、ラウリン酸アマイミドな
どの飽和脂肪酸モノアマイド類、オレイン酸アマイドな
どの不飽和脂肪酸モノアマイド類、Ｎ−ステアリルステ
アリン酸アマイドなどの置換アマイド類、メチロールス
テアリン酸アマイドなどのメチロールアマイド類、メチ
レンビスステアリン酸アマイドなどの飽和脂肪酸ビスア
マイド類、エチレンビスオレイン酸アマイドなどの不飽
和脂肪酸ビスアマイド類、ｍ−キシレンビスステアリン
酸アマイドなどの芳香族系ビスアマイド類を例示するこ
とができる。特に、脂肪酸アマイド類がエポキシ樹脂組
成物への相溶性が高いので好ましい。The components (e) and (f) act as a release agent and also have the function of uniformly dispersing the other release agents usable in the present invention in the epoxy resin composition. is there. The other release agent referred to herein is not particularly limited, but may be a saturated fatty acid monoamide such as lauric acid amide, an unsaturated fatty acid monoamide such as oleic acid amide, or a substitution such as N-stearyl stearic acid amide. Amides, methylol amides such as methylol stearic acid amide, saturated fatty acid bisamides such as methylene bis stearic acid amide, unsaturated fatty acid bis amides such as ethylene bis oleic acid amide, and aromatic compounds such as m-xylene bis stearic acid amide Bisamides can be exemplified. In particular, fatty acid amides are preferred because of their high compatibility with the epoxy resin composition.
【００２６】（ｃ）成分の配合量（（ｅ）成分と（ｆ）
成分とその他の離型剤の合計量）はエポキシ樹脂組成物
の全量に対して０．０５〜５重量％となるように設定す
るのが好ましい。０．０５重量％未満であれば、充分な
離型効果を得ることができなくなる恐れがあり、また５
重量％を超えると、成形品が白濁したり、半導体（素
子）やリードフレームなどのインナーとの密着性が低下
したり、耐湿信頼性が低下したり、成形品の強度が低く
なることにより耐クラック性が低下したりする恐れがあ
る。The amount of component (c) (component (e) and component (f)
The total amount of the components and other release agents) is preferably set to be 0.05 to 5% by weight based on the total amount of the epoxy resin composition. If the content is less than 0.05% by weight, a sufficient release effect may not be obtained.
If the content is more than 10% by weight, the molded product becomes cloudy, the adhesiveness to the inner member such as a semiconductor (element) or a lead frame is reduced, the moisture resistance reliability is reduced, and the strength of the molded product is reduced. Cracking properties may be reduced.
【００２７】（ｄ）成分の硬化促進剤としては、一般式
（１）（２）で示されるものを単独で用いたり併用した
りすることができる。尚、（２）の「Ｒ２・Ｒ３」はＲ
２へＲ３を付加した構造あるいは塩構造を示すものであ
る。As the curing accelerator of the component (d), those represented by the general formulas (1) and (2) can be used alone or in combination. Note that “R2 · R3” in (2) is R
2 shows a structure in which R3 is added to 2 or a salt structure.
【００２８】Ｒ２へＲ３を付加した構造を有する（２）
の化合物（付加物）としては、次の（５）（６）のよう
な化学式で示される。Having a structure in which R3 is added to R2 (2)
Is shown by the following chemical formulas (5) and (6).
【００２９】[0029]
【化９】 Embedded image
【００３０】また塩構造を有する（２）の化合物として
は、次の（７）〜（１２）ような化学式で示される。The compound (2) having a salt structure is represented by the following chemical formulas (7) to (12).
【００３１】[0031]
【化１０】 Embedded image
【００３２】さらに一般式（１）（２）に示す硬化促進
剤の他にも硬化促進剤を併用することができる。ここで
いう他の硬化促進剤としては、エポキシ樹脂と硬化剤の
反応を促進させるものであれば、特に制限はないが、比
較的着色の少ないものを用いるのが好ましい。具体的に
は、トリフェニルフォスフィン、ジフェニルフォスフィ
ンなどの有機フォスフィン系硬化促進剤、１，８−ジア
ザビシクロ（５，４，０）ウンデセン−７、トリエタノ
ールアミン、ベンジルジメチルアミンなどの三級アミン
系硬化促進剤、テトラフェニルホスホニウム・テトラフ
ェニルボレート、テトラフェニルホスホニウム・ブロマ
イドなどの有機塩類などを例示することができる。Further, in addition to the curing accelerators represented by the general formulas (1) and (2), a curing accelerator can be used in combination. There is no particular limitation on the other curing accelerator as long as it promotes the reaction between the epoxy resin and the curing agent, but it is preferable to use a relatively less colored one. Specifically, organic phosphine-based curing accelerators such as triphenylphosphine and diphenylphosphine; tertiary amines such as 1,8-diazabicyclo (5,4,0) undecene-7, triethanolamine and benzyldimethylamine Organic hardening accelerators, and organic salts such as tetraphenylphosphonium / tetraphenylborate and tetraphenylphosphonium / bromide can be exemplified.
【００３３】（ｄ）成分の配合量（（１）（２）に示す
硬化促進剤とその他の硬化促進剤の合計量）はエポキシ
樹脂組成物の全量に対して０．０５〜３重量％となるよ
うに設定するのが好ましい。（ｄ）成分の配合量が０．
０５重量％未満であれば、充分な硬化効果を得られず、
成形サイクルが低下する恐れがあり、また（ｄ）成分の
配合量が３重量％を超えると、ゲル化時間が短くなりす
ぎてボイドや未充填などの成形性が低下する恐れがあ
る。The compounding amount of the component (d) (the total amount of the curing accelerator and other curing accelerators shown in (1) and (2)) is 0.05 to 3% by weight based on the total amount of the epoxy resin composition. It is preferable to set so that (D) The amount of the component is 0.
If it is less than 05% by weight, a sufficient curing effect cannot be obtained,
If the molding cycle is reduced, and if the amount of the component (d) exceeds 3% by weight, the gelation time is too short, and the moldability such as voids and unfilled parts may be reduced.
【００３４】本発明では上記の（ａ）〜（ｄ）成分の他
に、必要に応じて、変色防止剤、劣化防止剤、染料、シ
リカなどの無機充填剤、シラン系カップリング剤、変性
剤、可塑剤、希釈剤などの添加剤を用いることができ
る。In the present invention, in addition to the above components (a) to (d), if necessary, a discoloration inhibitor, a deterioration inhibitor, a dye, an inorganic filler such as silica, a silane coupling agent, a modifier, And additives such as a plasticizer and a diluent.
【００３５】本発明の光半導体封止用エポキシ樹脂組成
物を調製するにあたっては、上記の（ａ）〜（ｄ）成分
とその他の添加剤を室温〜１５０℃の温度で溶解混合又
は溶融混合した後、三本ロールなどの混練機で溶融混練
し、これを冷却・固化した後、粉砕し、必要であれば、
タブレット状に打錠するようにする。また、性状が室温
で液状の場合は、溶解混合又は溶融混合するまでで調製
することができる。この時、（ａ）成分のエポキシ樹脂
と（ｂ）成分の硬化剤の配合割合は、反応性や硬化性な
どを考慮して、反応基（エポキシ基と水酸基）の当量比
で０．８〜１．２の範囲になるように設定する。In preparing the epoxy resin composition for encapsulating an optical semiconductor of the present invention, the above-mentioned components (a) to (d) and other additives are melted or mixed at a temperature of room temperature to 150 ° C. After that, it is melted and kneaded with a kneading machine such as a three roll, and after cooling and solidifying, pulverized, if necessary,
Tablets should be compressed. In addition, when the properties are liquid at room temperature, it can be prepared by dissolution mixing or melt mixing. At this time, the mixing ratio of the epoxy resin of the component (a) and the curing agent of the component (b) may be 0.8 to 0.8 in terms of the equivalent ratio of the reactive group (epoxy group to hydroxyl group) in consideration of reactivity and curability. Set to be in the range of 1.2.
【００３６】本発明の光半導体装置は、上記のエポキシ
樹脂組成物で光半導体（素子）を封止することによって
形成することができる。エポキシ樹脂組成物がタブレッ
ト（固形）の場合は、タブレットをトランスファー成形
して光半導体（素子）を封止し、光半導体装置を形成す
ることができる。この時の成形条件は、金型温度を１４
０〜１８０℃、注入圧力を１〜１０ＭＰａに設定するこ
とができる。またエポキシ樹脂組成物が液状の場合はキ
ャスティングやポッティング、印刷などの方式で注型及
び硬化させることによって、光半導体（素子）を封止
し、光半導体装置を形成することができる。The optical semiconductor device of the present invention can be formed by sealing an optical semiconductor (element) with the above epoxy resin composition. When the epoxy resin composition is a tablet (solid), the tablet can be transfer-molded to seal the optical semiconductor (element) to form an optical semiconductor device. The molding conditions at this time are as follows.
The injection pressure can be set to 0 to 180 ° C and the injection pressure to 1 to 10 MPa. When the epoxy resin composition is in a liquid state, the optical semiconductor (element) can be sealed by casting and curing by a method such as casting, potting, or printing to form an optical semiconductor device.
【００３７】そして本発明では、一般式（１）（２）の
硬化促進剤を用いるので、従来の硬化促進剤に比べてエ
ポキシ樹脂と硬化剤の反応を大きく促進することがで
き、成形サイクルを高くして生産効率を向上させること
ができるものであり、さらにバリ離型性や耐湿信頼性に
も優れるものである。また一般式（３）（４）の離型剤
を用いるので、外部離型剤を用いなくても成形体及びバ
リの金型からの離型性を高くすることができ、生産効率
を向上させることができるものである。しかも一般式
（３）（４）の離型剤を用いることによって、成形時の
金型からの連続離型性と光半導体（素子）及びリードフ
レームとの密着性という互いに相反する特性を合わせ持
ち、且つ成形体（光半導体装置）の外観的にも白濁がな
く、光透過性に優れたエポキシ樹脂組成物を得、これに
よりスプレー方式の外部離型剤を使用した成形体に比
べ、特性バラツキの小さい光半導体装置を得ることがで
きるものである。In the present invention, since the curing accelerators of the general formulas (1) and (2) are used, the reaction between the epoxy resin and the curing agent can be greatly promoted as compared with conventional curing accelerators, and the molding cycle can be shortened. It is possible to improve the production efficiency by increasing the height, and it is also excellent in the deburrability of the burr and the moisture resistance reliability. Further, since the release agents represented by the general formulas (3) and (4) are used, the releasability of the molded body and the burr from the mold can be increased without using an external release agent, and the production efficiency is improved. Is what you can do. In addition, by using the release agents represented by the general formulas (3) and (4), the mold has both contradictory properties of continuous release from a mold during molding and adhesion to an optical semiconductor (element) and a lead frame. In addition, an epoxy resin composition having no light turbidity in the appearance of the molded article (optical semiconductor device) and excellent in light transmittance is obtained, and as a result, there is a variation in characteristics as compared with a molded article using an external release agent of a spray method. It is possible to obtain an optical semiconductor device having a small size.
【００３８】[0038]
【実施例】以下本発明を実施例によって具体的に説明す
る。The present invention will be described below in detail with reference to examples.
【００３９】（実施例１乃至１２及び比較例）表１の配
合割合で（ａ）エポキシ樹脂と（ｂ）硬化剤と（ｃ）離
型剤と（ｄ）硬化促進剤を、１１０℃で溶融混合した
後、三本ロール混練機で５０℃、６０分間溶融混練し、
これを冷却・固化した後、粉砕し、タブレット状に打錠
して光半導体封止用エポキシ樹脂組成物を調製した。
（ａ）〜（ｄ）成分としては以下のようなものを用い
た。(Examples 1 to 12 and Comparative Example) (a) an epoxy resin, (b) a curing agent, (c) a release agent, and (d) a curing accelerator were melted at 110 ° C. in the proportions shown in Table 1. After mixing, melt kneading at 50 ° C. for 60 minutes with a three-roll kneader,
After cooling and solidifying, this was pulverized and tableted to prepare an epoxy resin composition for encapsulating an optical semiconductor.
The following components were used as the components (a) to (d).
【００４０】エポキシ樹脂（ア）：ビスフェノールＡ型
エポキシ樹脂（油化シェルエポキシ（株）製のエピコー
ト８２８） エポキシ樹脂（イ）：ビスフェノールＡ型エポキシ樹脂
（油化シェルエポキシ（株）製のエピコート１００１） エポキシ樹脂（ウ）：ビスフェノールＳ型エポキシ樹脂
（大日本インキ化学工業（株）製のＥＸＡ１５１４） 硬化剤（エ）：テトラヒドロ無水フタル酸無水物（新日
本理化（株）製のリカシッドＴＨ） 硬化剤（オ）：ヘキサヒドロ無水フタル酸無水物（新日
本理化（株）製のリカシッドＨＨ） 硬化剤（カ）：フェノール樹脂（三井東圧社製のＶＲ９
３００） 硬化促進剤（キ）：１−ベンジル−２−フェニルイミダ
ゾール（四国化成工業（株）製で一般式（１）の構造を
有するもの。Ｒ１はフェニル基、Ｒ２はベンジル基、Ｒ
４は及びＲ５は水素） 硬化促進剤（ク）：１−ベンジル−２−フェニルイミダ
ゾリウムトリメリテイト（四国化成工業（株）製で一般
式（２）の構造を有する付加物。Ｒ１はフェニル基、Ｒ
２はベンジル基、Ｒ３はトリメリット酸、Ｒ６は及びＲ
７は水素） 硬化促進剤（ケ）：テトラフェニルホスホニウム・テト
ラフェニルボレート（北興化学工業（株）製） 離型剤（コ）：一般式（３）の構造を有する第一級アル
コールのエトキシ化物（平均でＡ＝４９、Ｂ＝３０の
（ｅ）成分である） 離型剤（サ）：一般式（４）の構造を有する第一級カル
ボン酸のエトキシ化物（平均でＣ＝４８、Ｄ＝２７の
（ｆ）成分である） 離型剤（シ）：ベヘン酸アマイド（日本化成（株）製の
ダイヤミッドＢ９０） そして実施例及び比較例を以下のような試験で評価し
た。Epoxy resin (A): Bisphenol A type epoxy resin (Epicoat 828 manufactured by Yuka Shell Epoxy Co., Ltd.) Epoxy resin (a): Bisphenol A type epoxy resin (Epicoat 1001 manufactured by Yuka Shell Epoxy Co., Ltd.) Epoxy resin (c): bisphenol S-type epoxy resin (EXA1514 manufactured by Dainippon Ink and Chemicals, Inc.) Curing agent (d): tetrahydrophthalic anhydride (Rikashid TH manufactured by Nippon Rika Co., Ltd.) Agent (e): Hexahydrophthalic anhydride (Rikashid HH manufactured by Shin Nippon Rika Co., Ltd.) Curing agent (f): Phenolic resin (VR9 manufactured by Mitsui Toatsu Co., Ltd.)
300) Curing accelerator (g): 1-benzyl-2-phenylimidazole (manufactured by Shikoku Chemicals Co., Ltd. and having the structure of general formula (1). R1 is a phenyl group, R2 is a benzyl group, R
4 and R5 are hydrogens) Curing accelerator (h): 1-benzyl-2-phenylimidazolium trimellitate (manufactured by Shikoku Chemicals Co., Ltd. and having the structure of general formula (2). R1 is phenyl Group, R
2 is a benzyl group, R3 is trimellitic acid, R6 is
7 is hydrogen) Curing accelerator (q): tetraphenylphosphonium / tetraphenylborate (manufactured by Hokuko Chemical Industry Co., Ltd.) Release agent (co): ethoxylated primary alcohol having the structure of general formula (3) (It is a component (e) with A = 49 and B = 30 on average) Release agent (sa): Ethoxylated primary carboxylic acid having a structure of the general formula (4) (C = 48 on average, D Release agent (c): amide behenic acid (Diamid B90 manufactured by Nippon Kasei Co., Ltd.) Then, Examples and Comparative Examples were evaluated by the following tests.
【００４１】（I）光透過性試験 実施例及び比較例をトランスファー成形にて成形して厚
さ１ｍｍのテストピースを作成し、分光光度計（（株）
日立製作所製）を用いてテストピースの可視光領域の光
透過率を測定した。(I) Light Transmittance Test The examples and comparative examples were molded by transfer molding to prepare test pieces having a thickness of 1 mm, and the spectrophotometer was used.
The light transmittance of the test piece in the visible light region was measured using Hitachi, Ltd.).
【００４２】（II）バリ離型性試験 下記（III）の成形を行った後において、成形金型のエ
アーベント部及びパーティング面で発生するバリの離型
性を評価した。評価は以下の通りである。 ◎：非常にバリ剥離性に優れる ○：バリ剥離性に優れる △：現状レベル程度 ×：現状レベル以下 （III）耐湿信頼性試験 回路幅１０μｍ、内側と外側の回路間隔１０μｍ、厚み
１μｍの櫛形アルミニウムパターン１（図１に平面図を
示す）を基板の表面に蒸着にて形成してテストエレメン
トグループ（ＴＥＧ）を作成し、このテストエレメント
グループを４２アロイ／銀メッキリードフレームに搭載
し、これを実施例及び比較例で１６ＤＰＩパッケージ金
型を用いてトランスファー成形し（成形条件は温度１６
０℃、注入圧力６ＭＰａ）、この後、成形品を１５０℃
で２時間の条件でアフターキュアーし、実施例及び比較
例から形成される封止樹脂で封止された性能評価用の１
６ＤＩＰパッケージを得た。(II) Burr Releasability Test After the molding of the following (III), the releasability of burrs generated on the air vent portion and parting surface of the molding die was evaluated. The evaluation is as follows. ：: Extremely excellent burr-releasing property ○: Excellent burr-releasing property △: About current level ×: Below current level (III) Moisture resistance reliability test Comb aluminum with a circuit width of 10 μm, an inner and outer circuit interval of 10 μm, and a thickness of 1 μm Pattern 1 (a plan view is shown in FIG. 1) is formed on the surface of the substrate by vapor deposition to form a test element group (TEG). The test element group is mounted on a 42 alloy / silver-plated lead frame, and In Examples and Comparative Examples, transfer molding was performed using a 16 DPI package mold (the molding condition was a temperature of 16).
0 ° C, injection pressure 6MPa).
After-curing under the condition of 2 hours, and 1 for performance evaluation sealed with the sealing resin formed from the examples and comparative examples.
A 6DIP package was obtained.
【００４３】この１６ＤＩＰパッケージを１２１℃、１
００％ＲＨの条件下で５０時間ＰＣＴ試験を行い、オー
プン不良率（アルミニウムパターンが腐食され断線が発
生したものを不良とする）から評価した。評価は以下の
通りである。 ◎：不良率０％ ○：不良率２％以下 △：不良率５％以下 ×：不良率１０％以上 （IV）密着性試験 上記（III）の１６ＤＩＰパッケージにおいて、成形直
後とアフターキュアー後の素子（ＴＥＧ）と実施例及び
比較例から形成される封止樹脂の密着性を超音波探査装
置（キャノン製）を用いて評価した。評価は以下の通り
である。 ◎：チップ面全面密着、リードフレーム全面密着 ○：チップ面全面密着、リードフレーム小剥離 △：チップ面全面密着、リードフレーム中剥離 ×：チップ面剥離及び／またはリードフレーム剥離 （V）連続離型性試験 クリーニング後の金型に三回のダミー成形を行った後、
スプレー方式の外部離型剤（ワックス）を用いないで安
定して連続成形できる成形回数（ｓｈｏｔ数）をカウン
トした。金型及び成形条件は（III）と同様である。This 16 DIP package was heated at 121 ° C., 1
A PCT test was performed for 50 hours under the condition of 00% RH, and the evaluation was made based on the open defect rate (a defect in which the aluminum pattern was corroded and the disconnection occurred was regarded as a defect). The evaluation is as follows. ：: defective rate 0% ○: defective rate 2% or less △: defective rate 5% or less ×: defective rate 10% or more (IV) Adhesion test In the 16DIP package of the above (III), the element immediately after molding and after curing. The adhesion between (TEG) and the sealing resin formed from the examples and comparative examples was evaluated using an ultrasonic probe (manufactured by Canon). The evaluation is as follows. ◎: Full contact with chip surface, full contact with lead frame ○: Full contact with chip surface, small peeling of lead frame △: Full contact with chip surface, peeling inside lead frame ×: Peeling of chip surface and / or peeling of lead frame (V) Continuous release After performing dummy molding three times on the mold after cleaning,
The number of moldings (shot number) at which stable continuous molding was possible without using a spray type external release agent (wax) was counted. The mold and molding conditions are the same as in (III).
【００４４】上記（I）〜（V）の結果を表１に示す。Table 1 shows the results of the above (I) to (V).
【００４５】[0045]
【表１】 [Table 1]
【００４６】表１から明らかなように、実施例１乃至１
２を用いると比較例を用いた場合と同様の光透過性を有
しながら、バリ離型性、連続離型性、密着性、耐湿信頼
性を向上させることができた。特に、硬化促進剤や離型
剤を好適な範囲で配合した実施例１乃至９において、バ
リ離型性、連続離型性、密着性、耐湿信頼性が比較例よ
りも高くなった。As is clear from Table 1, Examples 1 to 1
When No. 2 was used, it was possible to improve the flash release property, the continuous release property, the adhesion, and the moisture resistance reliability while having the same light transmittance as that of the comparative example. In particular, in Examples 1 to 9 in which the curing accelerator and the release agent were blended in a suitable range, the burr release properties, continuous release properties, adhesion, and moisture resistance reliability were higher than those of Comparative Examples.
【００４７】[0047]
【発明の効果】上記のように本発明の請求項１の発明
は、（ａ）エポキシ樹脂、（ｂ）硬化剤、（ｃ）離型
剤、（ｄ）一般式（１）（２）の硬化促進剤の少なくと
も一方を含有するので、従来の硬化促進剤に比べてエポ
キシ樹脂と硬化剤の反応を大きく促進することができ、
成形サイクルを高くして生産効率を向上させることがで
きるものであり、さらに透明性、密着性、耐湿信頼性、
バリ離型性にも優れるものである。As described above, the invention of claim 1 of the present invention comprises (a) an epoxy resin, (b) a curing agent, (c) a release agent, and (d) a compound represented by the general formula (1) or (2). Since it contains at least one of a curing accelerator, it is possible to greatly promote the reaction between the epoxy resin and the curing agent as compared with a conventional curing accelerator,
It can improve the production efficiency by increasing the molding cycle, and furthermore, the transparency, adhesion, moisture resistance reliability,
It also has excellent flash release properties.
【００４８】また本発明の請求項２の発明は、（ｄ）硬
化促進剤の含有量が全量に対して０．０５〜３重量％で
あるので、生産効率の向上、透明性、密着性、耐湿信頼
性、バリ離型性の効果を確実に得ることができるもので
ある。In the invention of claim 2 of the present invention, since the content of the curing accelerator (d) is 0.05 to 3% by weight based on the total amount, improvement in production efficiency, transparency, adhesion, It is possible to surely obtain the effects of the moisture resistance reliability and the flash release property.
【００４９】また本発明の請求項３の発明は、（ｃ）離
型剤として、炭素数が１８以上のエトキシ化合物を用い
るので、外部離型剤を用いなくても成形体及びバリの金
型からの離型性を高くすることができ、生産効率をさら
に向上させることができるものであり、しかも透明性、
密着性、耐湿信頼性、バリ離型性の効果もさらに向上す
るものである。Further, the invention of claim 3 of the present invention is characterized in that (c) an ethoxy compound having 18 or more carbon atoms is used as a mold release agent, so that a molded product and a burr mold can be used without using an external mold release agent. From the mold, and the production efficiency can be further improved.
The effects of adhesion, moisture resistance reliability, and flash release properties are further improved.
【００５０】また本発明の請求項４の発明は、（ｃ）離
型剤として、（ｅ）一般式（３）で示される炭素数が１
８以上の第一級アルコールのエトキシ化合物を用いるの
で、生産効率の向上、透明性、密着性、耐湿信頼性、バ
リ離型性の効果を確実に得ることができるものである。Further, the invention of claim 4 of the present invention provides (c) a releasing agent having (e) a carbon number represented by the general formula (3) of 1
Since an ethoxy compound of 8 or more primary alcohols is used, it is possible to surely obtain the effects of improving production efficiency, transparency, adhesion, moisture resistance reliability, and flash release properties.
【００５１】また本発明の請求項５の発明は、（ｅ）一
般式（３）で示される炭素数が１８以上の第一級アルコ
ールのエトキシ化合物の含有量が全量に対して０．０５
〜５重量％であるので、生産効率の向上、透明性、密着
性、耐湿信頼性、バリ離型性の効果を確実に得ることが
できるものである。Further, the invention of claim 5 of the present invention is characterized in that (e) the content of the ethoxy compound of the primary alcohol having 18 or more carbon atoms represented by the general formula (3) is 0.05 to the total amount.
Since the content is about 5% by weight, it is possible to reliably obtain the effects of improvement in production efficiency, transparency, adhesion, moisture resistance reliability, and flash release properties.
【００５２】また本発明の請求項６の発明は、（ｃ）離
型剤として、（ｆ）一般式（４）で示される炭素数が１
８以上の第一級カルボン酸のエトキシ化合物を用いるの
で、生産効率の向上、透明性、密着性、耐湿信頼性、バ
リ離型性の効果を確実に得ることができるものである。Further, according to the invention of claim 6 of the present invention, (c) a releasing agent having (f) a carbon number represented by the general formula (4) of 1
Since an ethoxy compound of 8 or more primary carboxylic acids is used, it is possible to surely obtain the effects of improving production efficiency, transparency, adhesion, moisture resistance reliability, and flash release properties.
【００５３】また本発明の請求項７の発明は、（ｆ）一
般式（４）で示される炭素数が１８以上の第一級カルボ
ン酸のエトキシ化合物の含有量が全量に対して０．０５
〜５重量％であるので、生産効率の向上、透明性、密着
性、耐湿信頼性、バリ離型性の効果を確実に得ることが
できるものである。Further, the invention of claim 7 of the present invention is characterized in that (f) the content of the ethoxy compound of a primary carboxylic acid having 18 or more carbon atoms represented by the general formula (4) is 0.05 to the total amount.
Since the content is about 5% by weight, it is possible to reliably obtain the effects of improvement in production efficiency, transparency, adhesion, moisture resistance reliability, and flash release properties.
【００５４】本発明の請求項８の発明は、請求項１乃至
７のいずれかに記載の光半導体封止用エポキシ樹脂組成
物で封止するので、生産効率の向上、透明性、密着性、
耐湿信頼性、バリ離型性の効果を確実に得ることができ
るものである。According to the invention of claim 8 of the present invention, since it is encapsulated with the epoxy resin composition for encapsulating an optical semiconductor according to any one of claims 1 to 7, it is possible to improve production efficiency, transparency and adhesion.
It is possible to surely obtain the effects of the moisture resistance reliability and the flash release property.
【図１】テストエレメントグループの回路を示す平面図
である。FIG. 1 is a plan view showing a circuit of a test element group.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｈ０１Ｌ 23/31 Ｆターム(参考） 4J002 CC042 CD021 CD051 CD061 CD101 CD141 CN022 ED027 EL136 EL146 EN068 EN108 EU118 EU188 EW148 EW178 FD142 FD146 FD158 FD167 GQ05 4M109 AA01 BA01 CA01 CA05 CA12 CA21 EA02 EA06 EB02 EB03 EB04 EB06 EB08 EB09 EB13 EB19 EC01 EC05 EC07 EC09 EC11 EC20 GA01 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) H01L 23/31 F term (Reference) 4J002 CC042 CD021 CD051 CD061 CD101 CD141 CN022 ED027 EL136 EL146 EN068 EN108 EU118 EU188 EW148 EW178 FD142 FD146 FD158 FD167 GQ05 4M109 AA01 BA01 CA01 CA05 CA12 CA21 EA02 EA06 EB02 EB03 EB04 EB06 EB08 EB09 EB13 EB19 EC01 EC05 EC07 EC09 EC11 EC20 GA01
Claims (8)
（ｃ）離型剤、（ｄ）一般式（１）（２）の硬化促進剤
の少なくとも一方を含有して成ることを特徴とする光半
導体封止用エポキシ樹脂組成物。 【化１】 【化２】 但し、Ｒ１は水素、メチル基、イソプロピル基、ｔ−ブ
チル基、ウンデシル基、ヘプタデシル基、フェニル基、
ベンジル基、ヒドロキシメチル基などから選ばれる一つ
である。Ｒ２は水素、ベンジル基、メチル基、エチル
基、シアノメチル基、シアノエチル基などから選ばれる
一つである。Ｒ３は安息香酸、フタル酸、フマル酸、ト
リメリット酸、塩酸、イソシアヌル酸などから選ばれる
一つである。Ｒ４，Ｒ５，Ｒ６，Ｒ７は水素、メチル
基、ヒドロキシメチル基、ヒドロキシエチル基などから
選ばれる一つである。(1) an epoxy resin, (b) a curing agent,
An epoxy resin composition for optical semiconductor encapsulation, comprising (c) a release agent and (d) at least one of the curing accelerators of the general formulas (1) and (2). Embedded image Embedded image However, R1 is hydrogen, methyl group, isopropyl group, t-butyl group, undecyl group, heptadecyl group, phenyl group,
It is one selected from a benzyl group, a hydroxymethyl group and the like. R2 is one selected from hydrogen, a benzyl group, a methyl group, an ethyl group, a cyanomethyl group, a cyanoethyl group, and the like. R3 is one selected from benzoic acid, phthalic acid, fumaric acid, trimellitic acid, hydrochloric acid, isocyanuric acid and the like. R4, R5, R6, and R7 are one selected from hydrogen, a methyl group, a hydroxymethyl group, a hydroxyethyl group, and the like.
て０．０５〜３重量％であることを特徴とする請求項１
に記載の光半導体封止用エポキシ樹脂組成物。2. The method according to claim 1, wherein the content of the curing accelerator is 0.05 to 3% by weight based on the total amount.
The epoxy resin composition for optical semiconductor encapsulation according to the above.
のエトキシ化合物を用いて成ることを特徴とする請求項
１又は２に記載の光半導体封止用エポキシ樹脂組成物。3. The epoxy resin composition for optical semiconductor encapsulation according to claim 1, wherein (c) an ethoxy compound having 18 or more carbon atoms is used as a release agent.
（３）で示される炭素数が１８以上の第一級アルコール
のエトキシ化合物を用いて成ることを特徴とする請求項
１乃至３のいずれかに記載の光半導体封止用エポキシ樹
脂組成物。 【化３】 但し、Ａは１７〜１００の整数、Ｂは正の整数である。4. The method according to claim 1, wherein (c) the release agent comprises (e) an ethoxy compound of a primary alcohol having 18 or more carbon atoms represented by the general formula (3). 4. The epoxy resin composition for optical semiconductor encapsulation according to any one of 3. Embedded image Here, A is an integer of 17 to 100, and B is a positive integer.
１８以上の第一級アルコールのエトキシ化合物の含有量
が全量に対して０．０５〜５重量％であることを特徴と
する請求項１乃至４のいずれかに記載の光半導体封止用
エポキシ樹脂組成物。(E) The content of the ethoxy compound of the primary alcohol having 18 or more carbon atoms represented by the general formula (3) is 0.05 to 5% by weight based on the total amount. The epoxy resin composition for optical semiconductor encapsulation according to any one of claims 1 to 4.
（４）で示される炭素数が１８以上の第一級カルボン酸
のエトキシ化合物を用いて成ることを特徴とする請求項
１乃至５のいずれかに記載の光半導体封止用エポキシ樹
脂組成物。 【化４】 但し、Ｃは１７〜１００の整数、Ｄは正の整数である。6. The method according to claim 1, wherein (c) the release agent comprises (f) an ethoxy compound of a primary carboxylic acid having 18 or more carbon atoms represented by the general formula (4). 6. The epoxy resin composition for optical semiconductor encapsulation according to any one of items 1 to 5. Embedded image Here, C is an integer of 17 to 100, and D is a positive integer.
１８以上の第一級カルボン酸のエトキシ化合物の含有量
が全量に対して０．０５〜５重量％であることを特徴と
する請求項１乃至６のいずれかに記載の光半導体封止用
エポキシ樹脂組成物。(F) The content of the ethoxy compound of a primary carboxylic acid having 18 or more carbon atoms represented by the general formula (4) is 0.05 to 5% by weight based on the total amount. The epoxy resin composition for optical semiconductor encapsulation according to any one of claims 1 to 6.
導体封止用エポキシ樹脂組成物で封止して成ることを特
徴とする光半導体装置。8. An optical semiconductor device, which is encapsulated with the epoxy resin composition for optical semiconductor encapsulation according to any one of claims 1 to 7.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP01772699A JP3392068B2 (en) | 1999-01-26 | 1999-01-26 | Epoxy resin composition for optical semiconductor encapsulation and optical semiconductor device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP01772699A JP3392068B2 (en) | 1999-01-26 | 1999-01-26 | Epoxy resin composition for optical semiconductor encapsulation and optical semiconductor device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000212400A true JP2000212400A (en) | 2000-08-02 |
| JP3392068B2 JP3392068B2 (en) | 2003-03-31 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP01772699A Expired - Lifetime JP3392068B2 (en) | 1999-01-26 | 1999-01-26 | Epoxy resin composition for optical semiconductor encapsulation and optical semiconductor device |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006228708A (en) * | 2005-01-20 | 2006-08-31 | Mitsui Chemicals Inc | Organic EL sealing material |
| JP2008509241A (en) * | 2004-08-05 | 2008-03-27 | フライズ・メタルズ・インコーポレイテッド | Low porosity non-flowing fluxing underfill for electronic devices |
| JP2010144016A (en) * | 2008-12-17 | 2010-07-01 | Nitto Denko Corp | Epoxy resin composition for sealing optical semiconductor element, and optical semiconductor device using the same |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01275625A (en) * | 1988-04-28 | 1989-11-06 | Sumitomo Bakelite Co Ltd | Epoxy resin composition for semiconductor sealing |
| JPH03166221A (en) * | 1989-11-25 | 1991-07-18 | Shikoku Chem Corp | Epoxy resin composition |
| JPH08157695A (en) * | 1994-12-02 | 1996-06-18 | Shin Etsu Chem Co Ltd | Epoxy resin composition for semiconductor encapsulation and semiconductor device |
| JPH09208805A (en) * | 1994-11-09 | 1997-08-12 | Nitto Denko Corp | Epoxy resin composition for encapsulating optical semiconductor elements |
| JPH11343395A (en) * | 1998-06-02 | 1999-12-14 | Hitachi Chem Co Ltd | Epoxy resin composition for sealing optical semiconductor element and optical semiconductor element sealed therewith |
| JP2000063635A (en) * | 1998-08-25 | 2000-02-29 | Matsushita Electric Works Ltd | Epoxy resin composition for photo-semiconductor and photo-semiconductor device |
| JP2000160063A (en) * | 1998-09-21 | 2000-06-13 | Kubota Corp | Low temperature curing type powder coating composition and method for forming coating film on inner surface of metal tube using this powder coating composition |
| JP2000169671A (en) * | 1998-12-07 | 2000-06-20 | Sumitomo Bakelite Co Ltd | Epoxy resin composition and semiconductor device |
-
1999
- 1999-01-26 JP JP01772699A patent/JP3392068B2/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01275625A (en) * | 1988-04-28 | 1989-11-06 | Sumitomo Bakelite Co Ltd | Epoxy resin composition for semiconductor sealing |
| JPH03166221A (en) * | 1989-11-25 | 1991-07-18 | Shikoku Chem Corp | Epoxy resin composition |
| JPH09208805A (en) * | 1994-11-09 | 1997-08-12 | Nitto Denko Corp | Epoxy resin composition for encapsulating optical semiconductor elements |
| JPH08157695A (en) * | 1994-12-02 | 1996-06-18 | Shin Etsu Chem Co Ltd | Epoxy resin composition for semiconductor encapsulation and semiconductor device |
| JPH11343395A (en) * | 1998-06-02 | 1999-12-14 | Hitachi Chem Co Ltd | Epoxy resin composition for sealing optical semiconductor element and optical semiconductor element sealed therewith |
| JP2000063635A (en) * | 1998-08-25 | 2000-02-29 | Matsushita Electric Works Ltd | Epoxy resin composition for photo-semiconductor and photo-semiconductor device |
| JP2000160063A (en) * | 1998-09-21 | 2000-06-13 | Kubota Corp | Low temperature curing type powder coating composition and method for forming coating film on inner surface of metal tube using this powder coating composition |
| JP2000169671A (en) * | 1998-12-07 | 2000-06-20 | Sumitomo Bakelite Co Ltd | Epoxy resin composition and semiconductor device |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008509241A (en) * | 2004-08-05 | 2008-03-27 | フライズ・メタルズ・インコーポレイテッド | Low porosity non-flowing fluxing underfill for electronic devices |
| JP2006228708A (en) * | 2005-01-20 | 2006-08-31 | Mitsui Chemicals Inc | Organic EL sealing material |
| JP2010144016A (en) * | 2008-12-17 | 2010-07-01 | Nitto Denko Corp | Epoxy resin composition for sealing optical semiconductor element, and optical semiconductor device using the same |
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| Publication number | Publication date |
|---|---|
| JP3392068B2 (en) | 2003-03-31 |
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